Easy Agile Podcast Ep.5 Andrew Malak, Chief Product Officer at Spaceship

TL;DR

Jeff Gothelf, renowned author of "Lean UX" and "Who Does What By How Much," discusses the evolution from output-based work to outcome-focused goal setting with OKRs. Key insights: Teams need to shift from "we're building a thing" to defining success as "who does what by how much" – meaningful changes in human behaviour that drive business results; the biggest barrier to agile ways of working is that people get paid to ship features, not deliver value; leaders should change their questions from "what are you building?" to "what are you learning?"; psychological safety is critical – teams need to feel safe admitting when something isn't working; start small by simply asking "what will people be doing differently when we ship this?"; rename teams around outcomes (mobile revenue team) rather than outputs (iPhone app team); proactive transparency through weekly three-bullet-point updates builds trust with leadership. Bottom line: OKRs, when done right, are the "Trojan horse" that enables all other agile practices to succeed.

Introduction

For years, agile practitioners have championed better ways of working – Lean UX, design thinking, continuous discovery, customer centricity. Yet despite widespread adoption of these practices, many teams still struggle with the same fundamental problem: they're rewarded for shipping features, not delivering value.

In this episode, our CEO Mat Lawrence sits down with Jeff Gothelf to explore how this misalignment of incentives undermines even the best agile practices, and why customer-centric OKRs might be the missing piece that makes everything else click into place.

Jeff Gothelf is a renowned author, speaker, and consultant whose work has shaped how product teams approach collaboration and customer-centricity. Along with co-author Josh Seiden, Jeff wrote "Lean UX," which revolutionised how designers work in agile environments. Their follow-up book, "Sense and Respond," helped leaders understand how to manage in software-based businesses. Their latest book, "Who Does What By How Much," tackles the thorniest problem yet: how to align incentives and goals with customer outcomes.

This conversation traces Jeff's journey from helping designers work better in agile teams, to helping leaders create the conditions for success, to finally addressing the root cause – the goals and incentives that determine what gets celebrated, rewarded, and promoted in organisations. It's a masterclass in shifting from output thinking to outcome thinking, with practical advice for both team members and leaders navigating this transformation.

About Our Guest

Jeff Gothelf is an author, speaker, and organisational consultant who has spent over 15 years helping companies build better products through collaboration, learning, and customer-centricity. His work focuses on the intersection of agile software development, user experience design, and modern management practices.

Jeff is best known as the co-author (with Josh Seiden) of three influential books that have shaped modern product development practices. "Lean UX" (now in its third edition) began as a guide for designers working in agile environments but has evolved into a comprehensive framework for cross-functional collaboration and risk mitigation in product development. The book's core principle – moving from deliverables to outcomes – has influenced how thousands of teams approach their work.

Following "Lean UX," Jeff and Josh wrote "Sense and Respond," a book aimed at leaders and aspiring leaders. It makes the case that the overwhelming majority of businesses today are software businesses, and that managing software-based businesses requires fundamentally different approaches to team structure, management, and leadership. The book provides a roadmap for creating organisations where teams can actually practise the collaborative, customer-centric approaches described in "Lean UX."

Jeff's latest book, "Who Does What By How Much," represents the natural evolution of this work. After years of helping teams work better and leaders manage differently, Jeff and Josh identified that the real barrier to change was incentives and goals. Teams kept saying, "That's great, Jeff, but I get paid to ship features." This book tackles that problem head-on, showing how to use objectives and key results (OKRs) to create customer-centric goals that align with – rather than undermine – modern ways of working.

Beyond his books, Jeff has also authored "Forever Employable" and "Lean vs Agile vs Design Thinking," and he regularly speaks at conferences and consults with organisations on product strategy, team effectiveness, and organisational transformation. His approach is characteristically practical and rooted in real-world experience, making complex concepts accessible through clear frameworks and relatable examples.

Jeff's work continues to evolve as he helps organisations navigate the challenges of building products that customers actually want and need, whilst creating work environments where teams can thrive.

Transcript

Transcript

Note: This transcript has been lightly edited for clarity and readability.

Why Write Another Book? The Journey from Lean UX to OKRs

Mat Lawrence: Well, Jeff, welcome. I'm Mat Lawrence for our audience. I'm COO at Easy Agile, and today I'm talking with Jeff Gothelf, who is the renowned author, speaker, and consultant. You've written a good few books, Jeff. I've been looking through the list – Lean versus Agile versus Design Thinking, Forever Employable, and co-authored a few. The latest one being "Who Does What By How Much," and I was just telling Jeff in the intro here how you've managed to get across a lot of the things that I care about when trying to build teams and get them to understand OKRs. I've already given it to a few people and I'm definitely going to be giving it around. So, Jeff, welcome.

Jeff Gothelf: Thank you so much, Mat. That's very kind of you on all of that stuff. I appreciate it. Thanks for having me.

Mat: I'd love to cover a little bit around the book and the concept you're trying to get across. So I suppose the first question I have is what problem are you hoping to solve with the book? Why did you write it?

Jeff: It's really interesting. I wrote a blog post about this a while back because somebody challenged me on LinkedIn – and I appreciate a good challenge. They said, "How can you write about all this stuff? There's no way you know enough about each one of these topics to write a book. You're spreading yourself way too thin."

I thought that was a really interesting challenge. No one had ever asked that question, and it got me thinking. The answer that I came up with is that this book, "Who Does What By How Much," and it's a conversation about customer-centric objectives and key results, is the natural evolution of the work that Josh Seiden and I have been doing together for more than 15 years.

"We started with Lean UX, and Lean UX was a solution for designers helping them work more effectively in agile software development environments. The response to that book was, 'That's great, Jeff and Josh. We'd love to work this way. My company won't let me work this way.'"

So we wrote "Sense and Respond," which was a book for leaders and aspiring leaders to inspire them to manage differently, to recognise that the overwhelming majority of businesses today are software businesses, and that managing software-based businesses is different.

As we began to work with that material and talk about that, we kept bumping up against the same ceiling, and that ceiling was incentives and goals. No matter how hard we tried to convince people to be customer-centric, to learn continuously, to improve continuously, to work in short cycles, they said, "That's great, Jeff. But I get paid to ship features."

The goal, the measure of success, was shipped – preferably on time and on budget. That's what got celebrated and rewarded, incentivised and promoted. It was in the job descriptions and all that stuff. So it felt like we were really fighting a losing battle.

Objectives and key results has been gaining momentum for the last decade or so. To us, that felt like the perfect Trojan horse – and I know Trojan horse has a negative connotation, but I don't think of it in this case as a negative thing. It was the perfect way to have a conversation about goals in a customer-centric fashion that, if applied in the way that we describe in the book, would enable everything else that we've done to happen more easily.

"What Will People Be Doing Differently?" – The Question That Changes Everything

Mat: I love the evolution of it, Jeff. I've been working in tech now for about 15 years. Prior to that, I used to work in the arts and special effects, which in itself is a very agile industry where you're constantly building prototypes and figuring out what things need to do before they go on stage or be filmed.

When I entered into the tech world as an inexperienced founder and product developer, I was designing to solve problems, and I found the teams I was working with responded really well to that. "What are we trying to do? What are we trying to get here?" They used to give me feedback all the time on whether I was helping them see far enough ahead with the value we're actually trying to deliver.

When I joined Atlassian in 2014, when we were introducing OKRs there, I think we were facing a problem that you described really well in the book, which is around people focusing on shipping their to-do list. They have a backlog that is predefined, full of great ideas, and they really want to get it out the door. Trying to change that conversation to be around "how do we know if this is any good?" – the answer was we just don't know.

I'd love to touch on how have you guided teams to move from that more traditional output-based metrics and shipping into that outcome approach? Maybe you could give an example of where that shift has led to some significant success.

Jeff: Sure. The title of the book is "Who Does What By How Much?" Overwhelmingly, the teams that we've worked on and with over the years have focused on delivering output, making stuff. The question that we tried to get them to understand is: if you do a great job – let's say when – when you do a great job with this feature, how will you know? What will people be doing differently?

That's the question that starts the mindset shift from outputs to outcomes. Outcomes, the way that we describe them, is a meaningful change in human behaviour that drives business results. The human that we're talking about is the human that consumes the thing that you create.

"The question is how will you know you delivered value to that human? Traditionally, it's been like, 'Well, we made the thing for them. There it is.' We made the Sharpie. Terrific. Did anybody need a Sharpie? Anybody looking for a Sharpie? How do we know? What are people doing now that the Sharpie is out there?"

The mindset shift starts with that question. Even in an organisation that just doesn't get this yet, it's a really safe question. I think it's a safe question to say, "Okay, we're gonna build the thing. What do we expect people to be doing differently once we ship this thing?" And when I say people, let's get specific about who. Which people? Who?

This is the evolution of the book title and how we teach this stuff. So what would people be doing differently before we start? Which people? Who? Okay, it's accountants in large accounting firms. Great. When we ship this new system to them, what are they gonna be doing differently than they're doing today? Well, they'll be entering their data more successfully and finishing their work in half the time.

Terrific. What are they doing? Who does what? And how much of that do we need to see to tell us that this was actually valuable? Well, today they're seeing at least a 30% error rate in data entry. Okay, great. What's meaningful? What's a meaningful improvement? If we cut that in half, that's a meaningful improvement. By how much?

All of a sudden, we've constructed the success criteria that has moved the team away from "we're building a thing" to "accountants in large accounting firms reduce their data entry errors by 50%." Who does what by how much. That begins the mindset shift in that conversation in a safe way because we're not saying let's set new goals, let's rewrite our incentives. We're just saying, "Look, I'm just asking a question."

Then once we start to build stuff, and especially once we start to ship stuff, you remember that conversation we had three months ago? We talked about who does what by how much. Is it happening? Do we know? Can we find out? And if it isn't, let's figure it out.

The Non-Profit That Changed Their Approach - From One Million Buses to Ten Iterations

Jeff: I'll give you an example. There was an organisation I worked with – I really loved working with them. They were a non-profit organisation that was looking to address major diseases in the developing world. They had three or four very specific diseases that they were targeting in very specific locations around the world, and I was thrilled to be working with them and helping them.

They managed everything with a task list. They were like, "We're gonna create this campaign and we're gonna put it on buses in China." And I was like, "Okay. How do you know that? So what? If the campaign works, what will people be doing differently?"

"Well, they'll scan the QR code that's on the bus."

"Okay, alright. And then what?"

"They'll sign up for an appointment to get a cardiovascular check."

"And then what?"

"For those who need actual care, they'll sign up for care."

"All of a sudden, we've taken 'put an ad campaign on a bus' to 'who does what by how much.' When we started to think about it that way, they fundamentally were rethinking the level of effort."

Because you might imagine, it was going to be one million buses and hope that it works. Instead, they decided, "Hey, we're gonna do 100 of these in one locality, and we're gonna give it a week, and we're gonna not only see what happens, but find out if people saw the ad, if it speaks to them, if they understood what it said. Then based on that learning, we're gonna iterate on the campaign."

So instead of getting one giant shot at this advertising campaign to drive people to take better care of themselves, now they're gonna get ten iterations. I think that was massively impactful in helping that organisation do better work and help more people.

Mat: I love how you're bringing that back to the experimental and iterative approach that people so often want but really struggle to get to. I've seen so many occasions where OKRs end up describing something that takes three, four, five months to build and ship, and they're only trying to measure the big outcome at the end, whereas what you're talking about there is breaking it down, making it far more iterative and experimental.

Jeff: Reducing your risk. Imagine this organisation had, let's say, £100,000 for this campaign. Traditionally, they would spend that whole hundred grand and hope. The reality is there's no need to do that. They could spend 10 and learn and do a better job with the next 10 and a better job with the next 10, and if they've de-risked it enough, take the last 50 and dump it on the thing that you've actually validated.

It's a de-risking strategy as well. You're increasing the value you're delivering and reducing the risk of spending money on stuff that isn't gonna work. Feels like a no-brainer, doesn't it?

The Reverse Five Whys - Asking "So What?" to Find Your Outcome

Mat: You make it sound like everyone should be doing it, which I agree with. There was something that you did in the middle of that conversation which I really like, and it's kind of like the opposite of the five whys. You know, where you see the problem and you ask why, why, why and you go back to the root cause. Whereas you took that in the other direction there.

Jeff: Right. We were moving forward in time for the desired outcome.

Mat: Yeah, exactly. You said, "Okay, you want to put this thing on a bus. So what?" And you took that three or four steps forward to get to that ultimate outcome. I love that, and that's probably a tactical, practical approach that our audience can take.

I think some of the stuff that I've struggled with over the years is getting teams who are new to OKRs to understand how to move from writing their to-do list, writing their backlog, turning that into their key results, and actually getting it into the outcome base. I think that's one of the things that a lot of teams find hardest to grasp.

Jeff: And as I kicked off with, if your entire career you've been rewarded for shipping and producing and ticking off a to-do list, then it's really hard to break away from that without some form of leadership buy-in. That's coming back to that incentives and performance management criteria side of things. That's really hard because that's what people optimise for.

We can preach outcome-based work until we're blue in the face, as they say in America at least. But if you're paid to ship product, you're gonna optimise in most cases for what gets you paid. That's an important component of this that I think gets ignored a lot.

Two Audiences, Two Approaches - What Should Teams and Leaders Do Differently?

Mat: Let's talk practically around this. We're probably going to have different people listening to this. We could probably give two bits of advice. One is somebody who's in a team and they really want to try this, or maybe they've been trying this and struggling because the incentives don't match. The other group may be someone who's in leadership who is trying to change their organisation to move into this more outcome-based approach. What advice would you give to each of those people?

Jeff: Great question. Let's start with the folks trying to make this happen initially. In my opinion, one of the easiest ways to move this conversation forward in your organisation is to ask that question I mentioned: What will people be doing differently when we ship this?

Have that conversation. Position it any way you'd like, word it any way you'd like. But ultimately, you're not challenging the work. You're not saying "I'm not gonna do the work." You're not pushing back yet.

"All you're saying is, 'Look, we're gonna build this thing, and we're gonna do a great job. What do we hope people will do with this once we have it out there? What are we trying to see? Are we trying to see them increase average order value? Do we want them to abandon their shopping carts less? Are we trying to get them to sign up for a medical check-up at least once a year?'"

That starts it. That starts getting people to think about more than just "I am making a thing."

Mat: If you took that to leadership and said, "Yeah, we're gonna get this stuff out the door, but I want to check with you that you're happy that this is the outcome we're trying to get to, that this is the result if we get it right."

Jeff: I think that's great, and I think that you should come back to them after you ship and say, "Look, remember we met three, six, nine months ago and I said we're building this and we're hoping people will do this? Well, we built it as designed, on time, on budget, and so far we're not seeing the results that we anticipated. We talked to some customers, and here's why we think that is. What we'd like to do next..."

To me, that should be a safe conversation inside your organisation.

Mat: I can imagine people listening to this and getting some cold sweats at the concept of going to someone and saying, "I did everything that you expected from me, but it wasn't good enough."

Jeff: It's not that. What tends to happen in these situations is a lot of upfront planning and commitments, and then we execute. Regardless of all the work that people have done to convince people that there are better ways of working, that's generally speaking how people are doing work still. We did the thing, and guess what? It didn't work. It didn't work as we had hoped. It's not because we built it poorly. It works as designed. We did usability testing on it. People can use it, they can get through the workflow.

What we think is it's not solving a meaningful problem, or we decided to put it somewhere in the workflow that didn't make sense, or whatever the case is. I understand it's not a risk-free conversation. I'm not encouraging people to do things that are career-limiting per se, but at some point we've got to talk about this kind of stuff. Otherwise, we're just a factory. I don't think anybody wants to work in a factory.

It's Not About the Quality of Your Code, It's About Learning

Mat: I couldn't agree more, and I think that the heart of what I spend a lot of my time doing is helping people understand how to get the benefits out of being agile, that agility piece. What we've been discussing there is that key part of learning. You can plan and you can build, you can have alignment on those things, you can improve how you're building all the time and reach quality standards and pass usability testing. But ultimately, if you don't learn, you're never gonna get the insight that you need to adapt what you do next.

"Where a lot of people fall down with agility is they go through all of the motions up to that point, and then through fear, self-preservation, or they've just not seen anybody else around them do it before, they hesitate to say, 'This thing that we've all invested all this time and effort into isn't working as expected.' It does take some courage to do that."

Jeff: It does. I agree. But it's an evidence-based conversation. It's not "we did a crap job." We didn't. It's bug-free, it's high performance, it's scalable, it's usable. But you can build products like that – there are infinite stories of products that were amazingly executed that didn't meet a need, didn't solve a problem.

Mat: Yeah, I built one of those and had to close a business for it, so I know that all too well. If there's a lesson I learned through the years of doing that, which you touched on earlier, it's around by focusing on the outcomes that you want to see, those behaviours you want to change, and bringing the work down, de-scoping the work to start to experiment and iterate, you de-risk all of that. You'll learn a lot earlier whether you're on the right track or not rather than getting that big bang at the end.

Jeff: Yeah. Again, you're reducing the risk of building something that people don't want. Let's just use round numbers because they're easy. If you have a million-pound budget to build something – a new product, a new feature, a new service – and you spend 100 of that million and find out that this isn't the right thing to make, it's not a real problem, for whatever reason, you've just saved the company £900,000.

They should hoist you up on their shoulders and sing your praises, parade you around the halls. That's how it should be. You're a hero, and now we can take that £900 and do something that actually will deliver value with it.

If You're a Leader: Stop Asking "When Will It Be Ready?" and Start Asking "What Are You Learning?"

Mat: The second half of that question was around if you're a senior leader in an organisation and you want to move to an outcome-based approach, maybe you start with celebrating the people who are trying to do that and positively reinforcing it in that way. But what advice would you give that person?

Jeff: Absolutely. Celebrate anybody – literally hoist them up on your shoulders and parade them around the halls and say, "Look, this team tried this, figured out it wasn't going to work, and pivoted, and saved the company a million pounds." That should be a regular conversation and a regular thing that the company celebrates.

What's interesting is that you can find yourself on a team with resistant leadership, and you can also find yourself in leadership with resistant teams. And for a variety of reasons, not the least of which is that they've never actually been allowed to work this way and don't believe you that you're gonna let them work this way.

"Without getting caught up in too much process or training or dogma, I think as a leader you start to soften the conversations around this stuff by changing the questions that you ask."

Normally, it's like, "Hey, what are you guys working on? When will it be ready? How much is it gonna cost me? What do you predict the ROI is gonna be?" That's a typical line of questioning for a product team.

Conversely, you can say, "Hey, folks. What are you learning this week? This sprint? This quarter? What did you learn?" You might get a bunch of blank stares initially. They'll say, "What do you mean, what did we learn? We're building what you told us to build."

"Okay, well, cool. Next quarter when we meet, I'd love for you folks – I'm gonna ask you this question again. What did you learn this quarter about the product, about the customer, about the value of the thing that we're delivering? If you don't know how to answer those questions, I can help. I can get training for you. I can get some folks who've done this in other parts of the company to show you how they're doing this work."

To me, you're not enforcing. One of the issues of organisations just mashing process on top of organisations is folks don't understand why. Why are we doing this, and how is this supposed to make anything better? One of the ways to ease folks into a different way of working is to change your expectations of them and make that clear to them.

Instead of saying "What are you building? When will it be ready? What's the ROI?" say "What are you learning? Are we doing the right thing? How will we know?" And then if they don't know how to get the answers to that, don't make them feel stupid. Say, "Look, I'm gonna help you with that. I'll show you how the other teams are doing it. I'll get you some training. We'll work on this."

That's super powerful because you're changing the expectations that you have for your team, and you're making it explicit to them.

Navigating Conflicting Forces - Outcomes vs. Predictability

Mat: I've got this image in my head of people in a large organisation where they're on this journey that you've described with their team. Maybe they're a leader somewhere in the middle of the organisation, working with multiple teams, and they're starting to see some progress. The teams are on board, they trust that the questions you're asking are genuine and authentic, and they really want to understand the outcomes.

They're starting to come back with great questions themselves around who does what, what's the behaviour we're trying to change, how are we trying to change it, are we successfully doing that or not. Whilst that starts to get some traction and momentum, at the same time this leader's got other people in the organisation – maybe some more traditional executives who are getting investors on their boards asking for their KPIs to be met and the efficiency and the predictability they expect so they can forecast.

They have jobs to do themselves, and they seek some predictability. How do you help guide that person to navigate those two conflicting forces?

Jeff: It's hard. I've seen it multiple times. I think there are a couple of ways to navigate those political challenges in an organisation. One is you have to model the behaviour that you want to see both in your teams and in your colleagues as well.

Every interaction that you have with your peers at leadership level should contain these types of conversations around the customer, around learning, around value, around risk mitigation, and continuing to model the behaviour you want to see.

Someone says, "Well, we just have to build the iPhone app."

"Okay, great. But why? Why do we have to build the iPhone app?"

"Because we have to increase mobile revenue."

"Why? What is it today? What are we hoping to get?"

The Power of Renaming Teams

There's a super simple trick I wrote about probably a decade ago. If you're in a leadership position to get the organisation to start to think differently about how to do work, it's simply changing the names of the teams.

For example, let's say you and I work on the iPhone app team. What's our mission? Build an iPhone app. Exactly. So that's the iPhone app team, and that's the CRM team and that's the Android app team, whatever.

"What if we change the name of that team? Same team, same people. But it's the mobile revenue team. All of a sudden, the purpose of the team has fundamentally changed. It's no longer 'build iPhone app.' It's 'increase revenue through the mobile channel.'"

That might be an iPhone app, might be an Android app, might be a better website, might be a million different things. But from a leadership perspective, one of the things that you can influence is the name of these teams, and how you name them determines what work they do. That's really powerful.

Prove the Model

The other thing that you can do as a leader is prove the model. There's a lot of "my idea is better than your idea" type of conversations at work. Instead of saying, "I think we should work this way," say, "Look, I've got a pilot team in my group that's been doing this for the last three months. Here's what the team looks like. Here's the work that they're doing. Here's how they work. Here's what they're producing. Here's their happiness score. Here's their productivity. Here's their efficiency. Here's the impact of the work that they're doing with the customer."

If you've got one or two of those teams working that way, that's a compelling argument for saying, "Look, let's give it a shot." You've got the evidence that says this is a better way of working. Proving the model is always a good way to go.

Team Autonomy and Empowerment

Mat: One of the things that I'm picking up on in what you're saying leads to an outcome within teams that I've seen – around autonomy and empowerment within teams. Something I'm always trying to do in my role in organisations is make myself redundant. If the team don't need me anymore, I've done my job.

I'm at work where I've been very clear with the rest of the leadership team: I'm getting involved in way too many decisions, and I need to remove myself from those decisions because I'm slowing us down. If I have to have all of the context to be able to get involved with that and help move us forward, then we're gonna go slower than we should.

We're very quickly removing me from decisions, and it's been a great journey. Terrifying for me because I don't know as much about what's going on. But I'm seeing the teams themselves equipped with questions like "who does what by how much?" – that's one tool around the OKRs. Also equipped with other tools and ways of working, and usually it comes down to: are they asking the right questions? Are they applying the level of critical thinking to achieve those outcomes?

"Ultimately, if we can get teams to be more autonomous, leaders have a much better time of scaling themselves without burnout, without having to get really drawn in. When teams make decisions when you're not in the room that are fighting to achieve the outcome that you also want to achieve, that's when you really start to move quicker. That's when you start to really see the benefits of agility."

Have you got any thoughts on that that you'd like to share?

Jeff: It's a really tough sell. I see it all the time because I think that leaders have defined themselves – I don't want to speak in absolutes, so the majority of leaders have defined themselves in a way that says, "I tell people what to do." That's my job.

If you ask any kid – 10 years old, 12 years old, 9 years old – "What's a boss?" they'll say "A boss is someone who tells people what to do." I think we grow up with that, and I think leadership canon for the last hundred years has roughly said that, with the exception of the last 20 to 30 years where we've seen a lot of agile-themed, agility-themed leadership books and materials come out.

Still, I think the overwhelming majority of people believe that it's their job when they're in a leadership role to tell their teams what to do and to be keenly aware of every little detail. Because what if my boss comes to me and says, "Hey, what are your teams doing?" If the answer is "I don't know," that's probably a bad answer.

I agree with you. Day-to-day decision stuff – who better to make that decision than the teams doing the work day to day? They know far more about it than I do. They're with the work every day, they're with the customer every day, they're getting the feedback.

There's no reason for you to run these tiny things past the leader every day. It's exhausting for the leader, as you said, and the team knows more about it. Big strategic shifts, invalidated hypotheses, radical shifts in the market, new competitive threats – absolutely, let's talk about that.

The Two-Way Solution

I think there's a two-way solution here. Number one, leaders need to let go a little bit and understand that the most qualified people to make decisions about the day-to-day trivial stuff are the team doing the work.

David Marquet said this in "Turn the Ship Around." He ran the worst-performing nuclear submarine crew in the American Navy and turned it around to the best-performing crew. Basically, what he said was he pushed decision-making down as close to the work as possible. The only decision he kept for himself was whether or not to launch a nuclear missile, because people are gonna die and he didn't want that on anybody. That's his job as the leader.

Same thing here. You're gonna push decisions all the way down, and we've got to get folks to think about that.

Demand Proactive Transparency

To make that easier for people to swallow, people who are not used to this way of working, I think we have to demand greater proactive transparency from the teams.

Teams love to play the victim. "They don't let me work this way. My boss won't let me work this way. My boss doesn't get agility, doesn't get customer-centricity. She just comes down here and yells at us."

"What if on a weekly basis, without being asked for it, you sent your leader three bullet points in an email every week? Here's what we did this week. Here's what we learned. Here's what we're planning on doing next week."

If there's anything significant, you're gonna put that in there as well. But otherwise, just those three things. You're not even asking for a response. Weekly update, three bullet points, 15 minutes max of effort on your part.

In my opinion and in my experience, what happens is leaders chill out. Because all of a sudden they know what's going on. They see that you're doing work, that you're making objective decisions, and that you're taking the time to keep them informed. When their boss comes to them and says, "Hey, what are your teams doing?" they can just look at that email and be like, "This is what Mat's team is doing, this is what Jeff's team is doing."

To me, if there's a role here – and it's not an insignificant one – for the teams to play to improve their ways of working or to improve the comfort level that leaders have with new ways of working, this is it.

Mat: I have had the privilege of being someone on the recipient of those equivalent three-bullet-point emails running 12 different product teams, trying to understand what was going on. You're right – the stress levels go down when you understand proactively what's going on. It became the first thing I would do on a Monday morning knowing I had all that information.

It was something that teams were doing as part of their own weekly reviews as a team, and they just captured it and shared it. So there's no extra work for them. But it made this huge difference of suddenly I could understand where did I need to actually spend my time to help, rather than trying to chase and get information or get too close into managing people who didn't need it because they had it in hand.

I was able to prioritise and think, "Oh, that team looks like they're struggling, so we're gonna go and ask them some questions, see how I can remove some blockers for them."

Jeff: And if there is a blocker, add it in there. "We've been trying for three months to get access to customers. The sales team keeps blocking us. Can really use your help here."

The Shift from Being Rewarded for Knowing to Being Rewarded for Learning

Mat: There's a thing I've observed over the years – it takes a while to get there before you actually start getting rewarded for it in most organisations. In forward-thinking, very agile organisations, it starts a lot earlier, and I think that's something I'd like to try and shift left, try and get it earlier in people's careers.

It's this shift between: spend your entire career being rewarded for being knowledgeable, for being the expert, and knowing how to do something. You get promoted for that, you'll get a bonus for that, you'll get rewarded for it time after time. The more you learn, the more capable you become, the more experienced you are, you've got the answers for everything, you get promoted. You work your way up the career ladder.

Then you hit this tipping point where you hit a level where you realise there aren't many people around you at that point who are seeing the problems. Everyone's busy, everyone's focused on their thing. Then you realise that actually it's your job to call out that this thing isn't working. It becomes your responsibility to say, "There's a problem here we need to address as a company, as an organisation."

As an exec – Nick Muldoon is our CEO – we have an exec weekly, and the majority of that conversation is each of us saying what we don't understand, what we don't know, what we haven't figured out yet. We trust each other that all the rest of it's in hand and working beautifully. The things we really want to talk about is what don't we understand and what are we learning or what are we seeing that we need to try and figure out what to do with.

I see people struggle with that transition if they've not started it earlier in their career. Going back to the basics around sharing the learnings and are we actually achieving what we wanted to, are we seeing the behaviour shift, are we seeing it measured – if we're saying no, having the freedom to be able to call that out earlier, I think it makes that transition in life a lot more straightforward.

Jeff: Look, there's a level of seniority, and the subtheme here that we are dancing around but haven't yet named is psychological safety. It's this feeling that I'm comfortable calling things out that are against the grain, that contradict the plan, that are not working, and I keep seeing and nobody's addressing.

"I think there's a level of seniority that brings some psychological safety. But ultimately, organisational culture has to make it safe."

In other words, if leaders like you and your leadership team are consistently curious – "What do we not know? What are we not aware of? What's not working?" – your teams are going to feel comfortable calling those things out to you because you're asking those questions.

When they change the questions that they ask, it models psychological safety. It models the kinds of questions they want their teams to ask, and that's how change starts.

Building Psychological Safety - "If You Don't Know How, I'll Help You"

Mat: I couldn't agree more, Jeff. I think we've covered a lot of ground today, and psychological safety is one of those really hard intangible things for some people, particularly if they've never experienced it. We see it when we get new people joining our team. We're in a privileged environment where we have a lot of psychological safety.

When new people join from organisations that haven't had that, their behaviour is almost fighting against it. They hold on to their protected ways of working where they get a little bit territorial and they don't want to be vulnerable. It can take a good few months for people to settle in and relax into it.

There was a piece that I want to go back to, and maybe we wrap up on this. You talked earlier around a leader talking to their team and asking them questions to help them understand that it's okay to come back and say, "This thing that we've been developing, this product that we've been getting out the door, isn't having the desired impact." To look at it, question it, be curious, and come back to it.

The thing that you touched on there which I really love was that supportive nature of it. It's okay to do this, and if you don't know how to do it, I'll help you. If you were to give one last tip to our audience – how would you encourage people, leaders specifically, to move more into that space?

Jeff: I think it's a question of asking the right questions. I've been married a long time – half my life, it turns out. I did the maths the other day. If I've learned nothing in my 20-plus years of being married, I've learned that you don't start out immediately solving the problem. You listen and you ask questions. I've learned that. It took a long time.

I think that's our nature as leaders as well. The tendency is "let me solve that for you." Well, hang on. Before you jump to solutions, dig into the problem. What's the issue here? What's the problem? How can I best help you?

"Well, listen, we've set these customer-centric goals now. We've got great OKRs. Thanks for teaching us how to do that. Normally though, we're told what to do, and no one's telling us what to do now, and we don't know what to do. We have no idea how to figure that out. In the past, people have told us. Now I don't know what to do. Can you help us? How do we figure that out?"

To me, those are the kinds of answers you want to elicit from your teams. What's actually going on here?

This is where five whys comes in. "Well, you know, we keep hearing that we should be talking to customers. The reality is it's really difficult to get to our customers."

"Why is it difficult?"

"Well, because we're in a B2B space and we sell aeroplane engines."

"Okay, great. And why does that make it difficult to reach customers?"

"Well, because we have a sales team."

"Why does that make it difficult?"

"Well, because they guard their contacts and they don't want us messing with it."

"Okay, now I understand."

"I think if it's about asking the right questions as a leader, and then when you get to the root cause, you say, 'Well, listen, I can try to unblock it in this way. Do you think that would be helpful? Yes or no?' That becomes far more of a partnership than a hierarchical relationship."

Then you trust me to be honest with you about how well things are working and where things need help, and that's tremendous.

I run a very, very tiny business in the sense of number of people – it's three and a half people total. Even in a three-and-a-half-person business, people try to do good work and people don't want to bother you with what's going on. Sometimes people get overwhelmed, whether it's with work or personal stuff or a combination of the two, and then things start to slip.

The more you can foster that kind of transparency and trust, psychological safety, the less you find out that something is broken with the consequences of it being broken. You find out well in advance of anything actually happening.

Mat: I love that, Jeff. I think that's a great place to wrap up. I'm really grateful for your time, really enjoyed the conversation, and thank you for sharing your wisdom.

Jeff: My pleasure, Mat. Thanks so much for having me. This was fun.

---

‍

Thank you to Jeff Gothelf for joining us on this episode of the Easy Agile Podcast. To learn more about Jeff's work and get your copy of "Who Does What By How Much," visit jeffgothelf.com. You can also find his other books, including "Lean UX" and "Sense and Respond," which provide the foundation for the customer-centric approach to OKRs discussed in this episode.

‍

Subscribe to the Easy Agile Podcast on your favourite platform, and join us for more conversations about agile, product development, and building better teams.

What a great conversation this was with Chris Stone, The Virtual Agile Coach!

Chris shared some insights into the importance of sharing and de-stigmatising failures, looking after your own mental health, and why work shouldn't be stale.

Some other areas we discussed were, why you should spend time in self reflection - consider a solospective? and asking "how did that feel?" when working as a team.

"I really enjoyed our chat. Plenty to ponder over the silly season, and set yourself up with a fresh perspective for 2021. Enjoy and Merry Christmas!"

‍

‍

‍

Transcript

Sean Blake:

Hello, and welcome to another episode of the Easy Agile Podcast. It's Sean Blake here, your host today, and we're joined by Chris stone. Chris is going to be a really interesting guest. I really enjoyed recording this episode. Chris is the Virtual Agile Coach. He's an agility lead. People First champion blogger, speaker and trainer, who always seeks to gamify content and create immersive Agile experiences. An Agile convert all the way from back in 2012, Chris has since sought to broaden his experiences, escape his echo chamber and to fearlessly challenge dysfunction and ask the difficult questions. My key takeaways from this episode were; it's okay to share your failures, the importance of recognizing our mental health, why it's important that work doesn't become stale, how to de-stigmatize failure, the importance of selfreflection and holding many self retrospectives, and the origins of the word deadline. You'll be really interested to find out where that word came from and why it's a little bit troubling. So here we go. We're about to jump in. Here's the episode with Chris stone on the Easy Agile Podcast. Chris, thanks so much for joining us and spending some time with us.

Chris Stone:

Hey there Sean, thank you for having me. It's a pleasure.

Sean Blake:

I have to mention you've got a really funky Christmas sweater on today. And for those people listening on the audio, they might have to jump over to YouTube just for a section to check out this sweater. Can you tell us a bit about where that came from?

Chris Stone:

So this sweater was a gift. It's a Green Bay Packers, Chris, Ugly Christmas Jumpers, what they call it. And I'm a fan of the Green Bay Packers, I've been out there a few times to Wisconsin, Green Bay, Wisconsin. It's so cold out there in fact. When you're holding a beer and minus 13 degrees, the beer starts turning to slush just from being outside in the cold air. It's a great place, very friendly, and the jumper was just a gift one Christmas from someone.

Sean Blake:

Love it. There's nothing better than warm beer is there? Okay. So Chris, I first came across you because of the content that you put out on LinkedIn. And the way that you go about it, it's so much fun and so different to really anything else I've seen in the corporate space, in the enterprise space, in the Agile space even, why have you decided to go down this track of calling yourself the virtual Agile coach, building a personal brand and really putting yourself out there?

Chris Stone:

Well, for me, it was an interesting one because COVID, this year has forced a lot of people to convert to being virtual workers, remote workers, virtual coaches themselves. Now, what I realized this year is that, the aspiration for many is those co-located teams, it's always what people desired. They say, "Oh, you have to work harder, Katie, that's the best way." And I realized that in my whole Agile working life, I'd never really had that co-located team. There was always some element of distributed working and the past two years prior to where I'm currently, my current company, I was doing distributed scaled Agile with time zones, including Trinidad and Tobago, Alaska, Houston, the UK, India, and it was all remote.

Chris Stone:

And I thought, all right, this is an opportunity to recognize the fact that I was a virtual Agile coach already, but to share with others, my learnings, my experiences, the challenges I've faced, the failures I've had with the wider community so they can benefit from it because obviously, everyone, or more many have had to make that transition very quickly. And there's lots of learnings there that I'm sure people would benefit from. And this year in particular, I guess the honest answer, the reason for me being, I guess out there and working more on that side of things, being creative is because it's an outlet for my mental health.

Chris Stone:

I suffer from depression and one of my ways of coping with that is being creative and creating new content and sharing it. So I guess it's a reason of... it's linked to that also, but also the stories that people tell me afterwards, they motivate me to keep doing it. So when someone comes to me and says, "Hey, I did the Queen retrospective, the Queen Rock Band retrospective, and this program manager who never smiles connected to the content and admitted he liked Queen and smiled." And this was a first and when people come to me and say, "Hey, we did the Home Alone retrospective, the one of your Christmas themed ones and people loved it. It was great." It was the most engaging retrospective we've had so far because the problem is work can become stale if you let it be so.

Chris Stone:

Retrospectives can become this, what did we do last time? What are we going to do next time? What actions can we do? Et cetera, et cetera. And unless you refresh it and try new things, people will get bored and they'll disconnect and they'll disengage, and you're less likely to get a good outcome that way. So for me, there's no reason you can't make work a little bit fun, with a little bit of creativity and a little bit of energy and passionate about it.

Sean Blake:

I love that. And do you think a lot of people come to work even when they're working in Agile co-located teams and it's just not fun, I mean what do you think the key reasons are that work isn't fun?

Chris Stone:

I think because it can become stale. All right. So let's reflect on where we are today. Today, we're in a situation where we're not face-to-face with one another. We don't have time for those water cooler chats. We don't connect over a coffee or a lunch. We don't have a chat about idle banter and things of that on the way to a meeting room, we didn't have any of that. And that forces people to look at each other and see themselves as an avatar behind a screen, just a name. Often in particular, people aren't even on video camera.

Chris Stone:

It forces them to think of people as a name on a screen, rather than a beating heart on a laptop. And it can abstract people into just these entities, these names you talk to each day and day out, and that can force it to be this professional non-personal interaction. And I'm a firm believer that we need to change that. We need to make things more fun because it can, and in my experience, does result in much better outcomes. I'm very, very people first. We need to focus on people being people. People aren't resources. This is a common phrase I like to refer to you.

Sean Blake:

I love that, people aren't resources. You spoke a little bit about mental health and your struggle with depression. Something that I hear come up time and time again, is people that talk about imposter syndrome. And I wonder, firstly, if you think that might be exasperated through working remotely now. People are not so sure how they fit in, where their role is still the same role that it was 12 months ago. And do you have any tips for people when they're dealing with imposter syndrome, especially in a virtual environment?

Chris Stone:

Well, yeah I think this current environment, this virtual environment, the pandemic in particular, has led to a number of unhelpful behaviors. That there's a lot more challenges with people's mental health and negativity, and that can only lead to, I guess, less desire, less confidence in doing things, maybe doubting yourself. There's some great visuals I've shared on this recently, and it's all about reframing those imposter thoughts you have, the unhelpful thinking, that thing that goes through your mind that says, Oh, they're all going to think I'm a total fraud because maybe I don't have enough years of experience, or I should already know this. I must get more training. There's lots of “shoulding” and “musting” in that. There's lots of jumping to conclusions in this.

Chris Stone:

And a couple of ways of getting around that is, so if you're thinking of the scenario where I'm a fraud think, "Oh, well I'm doing my best, but I can't predict what they might think." When you're trying to think about the scenario of do I need to get more training? Well, understand and acknowledge the reality that you can't possibly know everything. You continue to learn every single day and that's great, but it's unrealistic to know it all. There's a great quote I often refer to and it's, true knowledge is knowing that you know nothing. I believe it's a quote from Socrates.

Chris Stone:

And it's something that very much resonates with me. Over the years I've gone through this learning journey where, when I first finished university, for example, I thought I knew everything. I thought I've got it all. And I'd go out to clients and speak and I'm like, "Oh yeah, I know this. I've got this guys." And then the more involved I've become and the more deeper I've gone into the topic, the more I realized, actually there's so much that I don't know. And to me, true knowledge is knowing that you know nothing tells me there's so much out there that I must continuously learn, I must continuously seek to challenge myself each and every day.

Chris Stone:

Other people who approach me and say, "How do you, or you produce a lot of content. How would you put yourself out there?" And I say, "Well, I just do it." Let's de-stigmatize failure. If you put a post out there and it bombs, it doesn't matter, put another one out there. It's as simple as that, learn from failure, Chuck something out there, try it, if it doesn't work, try something else. We coach Agile teams to do this all the time, to experiment. Have a hypothesis to test against that. Verify the outcomes and do retrospectives. I do weekly solospectives. I reflect on my week, what works, what hasn't worked, what I'm going to try differently. And there's no reason you can't do that also.

Sean Blake:

Okay. So weekly solospectives. What does that look like? And how do you be honest with yourself about what's working, what's not working and areas for yourself to improve? How do you actually start to have that time for self-reflection?

Chris Stone:

Unfortunately you got to make time for some reflection. One thing I've learned with mental health is you have to make time for your health before you have to make time for your illness or before you're forced to make time for your illness. And it can become all too easy in this busy working world to not make time for your health, to not make time and focus on you. So you do just have to carve out that time, whether that's blocking some time in the diary on a Friday afternoon, just to sit down and reflect, whether that's making time to go out for a walk, setting up a time on your Alexa to have a five minute stretching break, whatever it is, there's things you can do, and you have things you have to do to make time for yourself.

Chris Stone:

With regards to a solospective, the way I tend to do things is I tend to journal on a daily basis. That's almost like my own daily standard with myself, it's like, what have I observed? What have I... what challenges do I face in the past day? And then that sums up in the weekly solospective, which is basically a retro for one, where I reflect on, what did I try it? What do I want to achieve this week? What's gone well? What hasn't gone well. It's the same as a retrospective just one and allows me to aggregate my thoughts across the week, rather than them being single events. So that I'm focusing more on the trajectory as opposed to any single outlier. Does that make sense?

Sean Blake:

It does. It does. So you've got this trajectory with your career. You're checking in each week to see whether you're heading in the right direction. I assume that you set personal goals as well along the way. I also noticed that you have personal values that you've published and you've actually published those publicly for other people to look at and to see. How important are those personal values in informing your life and personal and career goals?

Chris Stone:

So I'd say that are hugely important, for me, what I thought was we see companies sharing their values all the time. You look on company websites and you can see their values quite prominently. And you could probably think do they often live up to their values? You have so many companies have customer centricity as their value, but how many of them actually focus on engaging with their customers regularly? How many have a metric where they track, how often they engage with customers? Most of them are focusing on velocity and lead time. So I always challenge, are you really customer centric or is that lip service? But moving aside, I digress. I thought companies have values, and obviously we do as well, but why don't we share them? So I created this visual, showing what mine were and challenged a few others to share it also. And I had some good feedback from others which was great.

Chris Stone:

But they hugely influence who I am and how I interact on a day-to-day basis. And I'll give you an example, one of my values is being open source always. And what that means is nothing I create, no content I create, nothing I produce would ever be behind a payroll. And that's me being community driven. That's me sharing what I've learned with others. And how that's come to fruition, how I've lived that is I've had lots of people come to me say, "Hey, we love the things you do. You gave me flying things. Would you mind, or would you like to collaborate and create this course that people would pay for?" So often I've said, "If it's free, yes. But if it's going to be monetized, then no."

Chris Stone:

And I've had multiple people reach out to me for that purpose. And I've had to decline respectfully and say, "Look, I think what you're doing is great. You've got a great app and I can see how having this Agile coaching gamification course on that would be of great value. But if it's behind the payroll, then I'm not interested because it's in direct conflict with my own values, and therefore, I wouldn't be interested in proceeding with it. But keep doing what you're doing, being people first, #people first." This is about me embodying the focus on people being beating hearts behind a laptop, rather than just this avatar on a screen. And I have this little... the audio listeners, won't be able to see this, but I'm holding up a baby Groot here. And he's like my people first totem.

Chris Stone:

And the reason for that is I have a group called the Guardians of Agility, and we are people first. That's our emblem. And these are my transformation champions in my current company. I like to have Guardians of Agility, and I've got this totem reminding me to be people first in every interaction I have. So when, for example, I hear the term resources and I'm saying, well... As soon as I hear it, it almost triggers me. I almost hear like, "Oh, what do they mean by that?" And I'll wait a little moment and I'll say, "Hey, can you tell me what you mean by that?" And you tease it out a little bit. And often they meant, "Oh, it's people, isn't it?" If you're talking about people, can we refer to them as people?

Chris Stone:

Because people aren't resources. They're not objects or things you mine out the ground. They're not pens, paper or desks. They're not chairs in an office. They are people. And every time you refer to them as a resource, you abstract them. You make it easier to dehumanize them and think of them as lesser, you make it easier to make those decisions like, oh, we can just get rid of those resources or we can just move that resource from here to there and to this team and that team, whether they want to or not. So I don't personally like the language.

Chris Stone:

And the problem is it goes all the way back to how it's trained. You go to university and you take a business degree and you learn about human resources. You take a course, Agile HR, Agile human resources, right, and it's so prevalent out there. And unless we challenge it, it won't change. So I will happily sit there and a meeting with a CTO and he'll start talking about resource and I'll say, "Hey, what do you mean by that?" And I'll challenge it and he'll go, "Yeah, I've done it again, have I not?" "Yes. Yes, you have." And it's gotten to the point now where I'll be on this big group call for example, and someone will say it, and I'll just start doing this on a screen waving, and they'll go, "Did it again, didn't I?" "Yes, you did."

Sean Blake:

So some of these habits are so ingrained from our past experiences our education, and when you're working with teams for the first time, who's never worked in Agile before, they're using phrases like resources, they're doing things that sometimes we call anti-patents, how do you start to even have that conversation and introduce them to some of these concepts that are totally foreign to people who've never thought the way that you or I might think about our teams and our work?

Chris Stone:

Sure. So I guess that the first response to that is with empathy. I'm not going to blame someone or make out that they're a bad person for using words that are ingrained, that are normal. And this is part of the problem that that term, resource is so ingrained in that working language nowadays, same as deadlines. Deadlines is so ingrained, even though deadlines came from a civil war scenario where it referred to, if you went past the line, you were shot. How did that land in the business language? I don't know. But resources, it's so ingrained, it's so entrenched into this language, so people do it without intending to. They often do it without meaning it in a negative way. And to be honest, the word itself isn't the issue, it's how people actually behave and how they treat people.

Chris Stone:

I said my first approach is empathy. Let's talk about this. Let's understand, "Hey, why did you use term?" "Oh, I use it to mean this." "Okay. Well." Yeah, and not to do it or call them out publicly or things like that. It's doing things with empathy. Now, I also often use obviously gamification and training approaches, and Agile games to introduce concepts. If someone's unfamiliar to a certain way of working, I'll often gamify. I'll create something, a virtual Agile game to demonstrate. The way I do say, is I'm always looking to help people understand how it feels, not just to talk theory. And I'll give you an example. I'm a big fan of a game called the Virtual Name Game. It's a game about multitasking and context switching.

Chris Stone:

And I always begin, I'll ask group of people, "Hey guys, can you multitask?" And often they go, "Yeah, we can do that." And there'll be those stereotypical things like, "Oh yeah, I'm a woman. I can do that." It happens. Trust me. But one of the first things I do, if I'm face-to-face with them, I'll say, "Hey, hold your hands out like this. And in your left hand..." And people on the audio can't see me, I'm holding out like my hands in front of me. In my left hand, we're going to play an endless game of rock, paper, scissors. And in my right hand, we're going to play a game of, we have a thumb war with each other. And you can try, you can challenge them, can they do those concurrently? No, they can't. They will fail because you just can't focus on both at the same time.

Chris Stone:

Now the Virtual Name Game, the way it works is you divide a group of people up into primarily customers and one developer. And I love to make the most senior person in the room, that developer. I want them to see how it feels to be constantly context switching. So if you were the developer, you're the senior person to review the hippo in this scenario, the highest paid person. I would say Sean, in this game, these customers, they are trying to get their name written first on this virtual whiteboard. And we're going to time how long it takes for you to write everyone's name in totality. The problem is that they're all going to shouting at you continuously, endlessly trying to get your attention. So it's going to be Sean, Sean, write my name, write my...

Chris Stone:

And it's just going to be wow, wow, wow, who do I focus on? You won't know. And this replicates a scenario that I'm sure many people have experienced. He who shouts loudest gets what they want. Prioritization is often done by he who's... or the person who shouts loudest not necessarily he. We then go into another rounds where you say, I'm this round, Sean, people are to be shouting their name at you. But in this round, you're going to pay a little bit attention to everyone. So the way you're going to do that is you're going to read the first letter of one person's name, then you move on to the first letter of the next person's name, and you're going to keep going around. The consequence of that is everyone gets a little bit of attention, but the result is it's really slow.

Chris Stone:

You're starting lots of things but not finishing them. And again, in each round, we're exploring how it feels. How did it feel to be in that round? Sean, you were being shouted at, how did that feel? Everyone else, you were shouting to get your attention. You had to shout louder than other people, how did that feel? And it's frustrating, it's demotivating, it's not enjoyable. In the final around, I would say, "Hey, Sean, in this round, I'm going to empower you to decide whose name you write first. And you can write the whole thing in order. And the guys actually they're going to help you this time, there are no shouts over each other, they are going to help you." And in this scenario, as I'm sure you can imagine, it feels far better. The result is people finish things, and you can measure the output, the number of brand names written on a timeframe.

Chris Stone:

It's a very quick and easy way of demonstrating how it feels to be constantly context switching and the damage you can have, if, for example, you've prioritized things into a sprint and you got lots of trying to reorder things and so on and so forth, and lots of pressure from external people that ideally should be shielded from influencing this and that, and how that feels and what the result is, because you may start something, get changed into something else. You got to take your mindset of this, back into something else, and then the person who picks up the original thing might not have even been the same person, they've got to learn that over again. There's just lots of waste and efficiency costs through that. And that's just an example of a game I use, to bring that sort of things to life.

Sean Blake:

That's great. That's fantastic. I love that. And I think we need to, at Easy Agile, start playing some of those games because there's a lot of lessons to be learned from going through those exercises. And then when you see it play out in real life, in the work that you're doing, it's easier to recognize it then. If you've done the training, you've done the exercise, that all seems like fun and games at the time, but when it actually rears its head in the work that you're doing, it's much easier to call it out and say, "Oh wait, we're doing that thing that we had fun playing, but now we realize it's occurring in real life and let's go a different direction." So I can see how that would be really powerful for teams to go through that so Chris [crosstalk 00:22:26].

Chris Stone:

I'd also add that every game that I do, I construct it using the four Cs approach. So I'm looking to connect people... firstly, connect people to each other, and then to the subject matter. So in this game is about multitasking. To contextualize why that matters, why does context switching and multitasking matter in the world of work? Because it causes inefficiencies, because it causes frustration, de-motivation, et cetera. Then we do some concrete practice. We play a game that emphasizes how it feels. And at the end we draw conclusions, and the idea is that with the conclusion side of things, it's almost like a retrospective on the game. We say, "Hey, what did we learn? What challenges we face? And what can we do differently in our working world?" And that hopefully leaves people with actionable takeaways. A lot of the content I share is aiming to leave it with actionable takeaways, not just talking about something, but reflecting on what you could do differently, what you could try, what experiment you might like to employ with your working life, your team that might help improve a situation you're facing.

Sean Blake:

Okay. Yeah, that's really helpful. And you've spoken about this concept of Agile sins, and we know that a lot of companies have these values, they might've committed to an Agile transformation. They might've even gone and trained hundreds or thousands of people at accompany using similar tactics and coaching and educational experiences that you provide. But we still see sometimes things go terribly wrong. And I wonder, what's this concept of Agile sins that you talk about and how can we start to identify some of these sins that pop up in our day-to-day work with each other?

Chris Stone:

I guess, so the first thing I would emphasize about this is that using sin, it's a very dogmatic religious language and it's more being used satirically than with any real intent. So I just like to get that across. I'm not a dogmatic person, I don't believe there is any utopian solution. I certainly don't believe there's any one size fit to all situation for anyone. So the idea that there's really any actual sins is... yeah, take that with a pinch of salt. The reason the Agile sins came up is because I was part of... I'd done a podcast recently with a guy called Charles Lindsey, and he does this Agile confessional. And it's about one coach confessing to another, their mistakes, their sins, the things they've done wrong.

Chris Stone:

And I loved it because I'm all about de-stigmatizing failure. I'm all about sharing with one another, these war stories from one coach to another, because I've been a proponent of this in the past. I've shouted, "Hey there, I failed on this. I made this mistake. I learned from it." And I challenge others to do so as well and there's still this reluctance by many to share what went wrong. And it's because failure is this dirty word. It's got this stigma attached to it. No one wants to fail, leaders in particular. So the podcast was a great experience.

Chris Stone:

And it was interesting for me because that was the first time I'd given a confession, because I'll be honest with you, I'm someone who is used to taking confession myself. I go to this hockey festival every year and I got given years ago, this Archbishop outfit, and I kind of made that role my own way. I was drunk, and I said, "You're going to confess your sins to me." And if they haven't sinned enough, I tell them to go and do more. And I give them penicillin with alcohol shots and things like that. And I've actually baptized people in this paddling pool whilst drunk. Anyway, again, I digress, but I wasn't used to confessing myself, usually, I was taking confession, but I did so and it was a good experience to share some of my failures and my patterns was to create... and it was my own idea, to create my videos, seven videos of my seven Agile sins. And again, this was just me sharing my mistakes, what I've learned from that, with the intent of benefiting others to avoid those similar sins.

Sean Blake:

So you've spoken to a lot of other Agile coaches, you've heard about their failures, you confessed your own failures, is it possible for you to summarize down what are those ingredients that make someone a great coach?

Chris Stone: And that is a question, what makes someone a great coach? I think it's going to be entirely subjective, to be honest. And my personal view is that a great coach listens more than they speak. I guess that would be a huge starting point. When they listen more than they speak, because I've... and this is one of the things I've been guilty of in the past, is I've allowed my own biases to influence the team's direction. An approach I'd taken in the past was, "Hey, I'm working with this team and this has worked well in the past. We're going to do that." Rather than, "So guys, what have you done so far? What have you tried? What's worked well? What hasn't worked well? What can we create or what can we try next? That works for you guys. Let's have you make that decision and I'm here to guide you through that process to facilitate it, rather than to direct it myself."

Chris Stone:

Again, I find ... it's an approach that resonates more with people. They like feel that they own that decision as opposed to it being forced upon them. And there's far less, I guess, cognitive dissonance as a consequence. So listening more than speaking is a huge for me, a point an Agile coach should do. Another thing I think for me nowadays, is that there's too much copying and pasting. And what I mean by that is, the Spotify, the Spotify model came out years ago and everyone went, "Oh, this is amazing. We're going to adopt it. We're going to have tribes and chapters and guilds and squads, and it's going to work for us. That's that's our culture now."

Chris Stone:

I was like, "Well, let's just take a moment here. Spotify never intended for that to happen. They don't even follow that model themselves anymore. What you've done there is you've just tried to copy and paste another model." And people do it with SAFe as well. They just say, "Hey, we're going to take the whole SAFe framework and Chuck it into our system in this blueprint style cookie cutter." And the problem is that it doesn't take into account for me, the most important variable in any sort of transformation initiative, the people, what they want, and the culture there. So this is where another one of my values is, innovate, don't replicate. Work with people to experiment and find that Agile, what works for them rather than just copying and pasting things.

Chris Stone:

So tailor it to their needs rather than just coming in with some or seen dancing framework, and then the way I do it is I say, "Hey, well, SAFe is great. Well, it's got lots of values, and lots of great things about it. Lots of benefits to it, but maybe not all of it works for us. Let's borrow a few tenent of that." Same with LeSS, same with Scrum At Scale, same with Scrum, similar to Kanban. There's lots of little things you can borrow from various frameworks, but there's also lots of things you can inject yourself, lot's of things you can try that work for you guys, and ultimately come up with your own tailor-made solutions. So innovate, don't replicate would be another one for me.

Chris Stone:

Learning, learning fast and learning often, and living and breathing that yourself. Another mistake I and other coaches I think have made is not making time for your own personal development to allowing, day in, day out to just be busy, busy, busy, but at the same time you're going out there, coaching teams, "Hey, you've got to learn all the time. You got to try new things." But not making that time for yourself. So I always carve out time to do that, to attend conferences, to read books, to challenge myself and escape my echo chamber. Not just to speak to the same people I do all the time, but perhaps to go on a podcast with people I've never spoken to. To a different audience, maybe to connect with people that actually disagree with me, because I want that.

Chris Stone:

I don't want that homophilous thinking where everyone thinks exactly like I do, because then I don't get exposed to the perspectives that make me think differently. So I'm often doing that. How can I tend to conference that I know nothing about, maybe it's a project management focus one. Project management and waterfall isn't a dirty word either. There is no utopian system, project management and... sure traditional project management and waterfall has its benefits in certain environments. Environments with less footing, less flexible scope or less frequently changing requirements works very well.

Chris Stone:

I always say GDPR, which is an EU legislation around data protection, that was a two year thing in the making and everyone knew exactly what was happening and when they had to do it by. That was a great example of something that can be done very well with a waterfall style, because the requirements weren't changing. But if you are trying to develop something for a customer base that changes all the time, and you've got lots of new things and lots of competitors and things like that, then it varies, and probably the ability to iterate frequently and learn from it is going to be more beneficial and this is where Agile comes in. So I guess to sum up there, there's a few things, learning fast learning often. I can't even remember the ones I've mentioned now, I've gone off on many tangents and this is what I do.

Sean Blake:

I love it. It's great advice, Chris. It's really important and timely. And you mentioned, earlier on that the customer base that's always changing and we know that technology is always changing and things are only going to change more quickly, and disruptions are only going to be more severe going forward. Can you look into the future, or do you ever look into the future and say, what are those trends that are emerging in the Agile space or even in work places that are going to disrupt us in the way that we do our work? What does Agile look like in five or 10 years?

Chris Stone:

Now that again is a very big question. I can sit here and postulate and talk about what it might look like. I'm going to draw upon what I think is a great example of what will shape the next five or 10 years. In February, 2021, there's a festival called Agile 20 Reflect, I'm not sure if you've heard of it, and it's built as a festival, not conference, it's really important. So it's modeled on the Edinburgh festival and what it intends to be is a celebration of the past, the present and the future of Agile. Now what it is, it's a month long series of events on Agile, and anyone can create an event and speak and share, and it will create this huge community driven load of content that will be freely accessible and available.

Chris Stone:

Now, there are three of the original Agile manifestor signatories that are involved in this. Lisa Adkins is involved in this as is lots of big name speakers that are attached to this festival. And I myself, I'm running a series of retrospectives on the Agile manifesto. I've interviewed Arie van Bennekum, one of the original Agile manifesto signatories. They're going to be lots of events out there. And I think that festival will begin to shape in some way, what Agile might look like because there's lots of events, lots of speakers, lots of panel discussions that are coming up, coming together with lots of professionals out there, lots of practitioners out there that will begin to shape what that looks like. So whilst I could sit here and postulate on it, I'm not the expert to be honest, and there are far greater minds than I. And actually I'd rather leverage the power of the wider community and come into that than suggesting mine at this time.

Sean Blake:

Nice. I like it. And what you've done there, you've made it impossible for us to click this video and prove you wrong in the future when you predict something that doesn't end up happening. So that's very wise if you.

Chris Stone: Future proof myself.

Sean Blake: Exactly. Chris, I think we're coming almost to the end now, but I wanted to ask, given the quality of your Christmas sweater, do you have any tips for teams who are working over the holiday period, they're most likely burnt out after a really difficult 2020? What are some of the things you'd say to coaches on Agile teams as they come into this time where hopefully people are able to take some time off, spend some time with their family. Do you have any tips or recommendations for how people can look after their mental health look after their peers and spend that time in self-reflection?

Chris Stone:

Sure. So a number of things that I definitely would recommend. I'm currently producing and sharing this Agile advent calendar. And the idea is that every day you get a new bite-size piece of Agile knowledge or a template or something working in zany or a video, whatever it may be. There's lots of little things getting in there. And there's been retro templates, Christmas and festive themes. So there's a Home Alone one, a Diehard one, an elf movie one, there's all sorts. Perhaps try one of those as a fun immersive way with your team to just reflect on the recent times as a squad and perhaps come up with some things in the next year.

Chris Stone:

And there's for example, the Diehard one, it's based on the quotes from the movie Diehard so it's what you'd be doing in there, celebrate your... to send them to your team. Or there's one in there about, if this is how you celebrate Christmas, I can't wait for new year. And that question was saying, what do we want to try next year? Like this year has been great, what do we want to try differently next year? So there's opportunities through those templates to reflect in a fun way so give one of those a go. I shared some Christmas eve festive Zoom backgrounds, or Team backgrounds, give those a go and make a bit fun, make it a bit immersive. There's Christmas or festive icebreakers that you can use. What I tend to do is any meeting I facilitate, the first five minutes is just unadulterated chat about non-work things, and I often use icebreakers to do so. And whether that's a question, like if you could have the legs of any animal, what would you have and why, Sean, what would that be?

Sean Blake:

Probably a giraffe, because just thought the height advantage, it's got to be something that's useful in everyday life.

Chris Stone: Hard to take you on the ground maybe.

Sean Blake:

Yes. Yes, you would definitely need that. Although, I don't think I would fit in the lift on the way to work, so that would be a problem.

Chris Stone:

Yeah. That's just how I start. But yeah, that's just a question, because it's interesting to see what could people come up with, but there's some festive ones too, what's your favorite Christmas flick? What would put you on the naughty list this year? Yeah, does your family have any weird or quirky Christmas traditions? Because I love hearing about this. Everyone's got their own little thing, whether it's we have one Christmas present on Christmas Eve or every Christmas day we get a pizza together. There's some really random ones that come out. I love hearing about those and making time for that person interaction, but in a festive way can help as well.

Chris Stone:

And then on the mental health side of things, I very much subscribed to the Pomodoro effect from a productivity side of things. So I will use that. I'll set myself a timer, I'll focus without distractions, do something. And then in that five minute break, I'll just get up and move away from my desk and stretch and get a coffee or whatever it may be. But then I'll also block out time, and I know some companies in this remote working world at the moment are saying, "Hey, every one to 2:00 PM is blocked out time for you guys to go and have a walk." Some companies are doing that. I always make time to get out and away from my desk because that... and a little bit more productive and it breaks up my day a little bit. So I definitely recommend that. Getting some fresh air can do wonders for your mental health.

Sean Blake:

Awesome. Well, Chris, I've learnt so much from this episode and I really appreciate you spending some time with us today. We've talked about a lot of things from around the importance of sharing your failures, the importance of looking after your mental health, checking in on yourself and your own development, but also how you tracking, how you feeling. I love that quote that you shared from, we think it Socrates, that true knowledge is knowing that you know nothing. I think that's really important, every day is starting from day one, isn't it? De-stigmatizing failure. The origins of the word deadline. I did not know that. That's really interesting. And just asking that simple question, how did that feel? How did that feel working in this way? People were screaming your name, walk up work, when work's too busy, how does that feel? And is that a healthy feeling that everyone should have? So that's really important questions for me to reflect on and I know our audience will really appreciate those questions as well. So thanks so much Chris, for joining us on the Easy Agile Podcast.

Chris Stone:

Not a problem. Thank you for listening and a Merry Christmas, everyone.

Sean Blake:

Merry Christmas.

In this insightful episode, we dive deep into one of the most common frustrations in engineering and dev teams: retrospectives that fail to drive meaningful change. Join Jaclyn Smith, Senior Product Manager at Easy Agile, and Shane Raubenheimer, Agile Technical Consultant at Adaptavist, as they unpack why retrospectives often become checkbox exercises and share practical strategies for transforming them into powerful engines of continuous improvement.

Want to put these insights into practice? We hosted a live, hands-on retro action workshop to show you exactly how to transform your retrospectives with practical tools and techniques you can implement immediately.

Key topics covered:

• Common retrospective anti-patterns and why teams become disengaged
• The critical importance of treating action items as "first-class citizens"
• How to surface recurring themes and environmental issues beyond team control
• Practical strategies for breaking down overwhelming improvement initiatives
• The need for leadership buy-in and organizational support for retrospective outcomes
• Moving from "doing agile" to "being agile" through effective reflection and action

This conversation is packed with insights for making your retrospectives more impactful and driving real organizational change.

About our guests

Jaclyn Smith is a Senior Product Manager at Easy Agile, where she leads the Easy Agile TeamRhythm product that helps teams realize the full benefits of their practices. With over five years of experience as both an in-house and consulting agile coach, Jaclyn has worked across diverse industries helping teams improve their ways of working. At Easy Agile, she focuses on empowering teams to break down work effectively, estimate accurately, and most importantly, take meaningful action to continuously improve their delivery and collaboration.

Shane Raubenheimer is an Agile Technical Consultant at Adaptavist, a global family of companies that combines teamwork, technology, and processes to help businesses excel. Adaptavist specializes in agile consulting, helping organizations deliver customer value through agile health checks, coaching, assessments, and implementing agile at scale. Shane brings extensive experience working across multiple industries—from petrochemical to IT, digital television, and food industries—applying agile philosophy to solve complex organizational challenges. His expertise spans both the technical and cultural aspects of agile transformation.

Transcript

This transcript has been lightly edited for clarity and readability while maintaining the authentic conversation flow.

Opening and introductions

Jaclyn Smith: Hi everyone, and welcome back to the Easy Agile Podcast. Today I'm talking to Shane Raubenheimer, who's with us from Adaptavist. Today we're talking about why your retrospectives keep failing and how to finally fix them. Shane, you and I have spent a fair amount of time together exploring the topic of retros, haven't we? Do you want to tell us a little bit about yourself first?

Shane Raubenheimer: Yeah, hello everyone. I'm Shane Raubenheimer from Adaptavist. I am an agile coach and technical consultant, and along with Jaclyn, we've had loads of conversations around why retros don't work and how they just become tick-box exercises. Hopefully we're going to demystify some of that today.

Jaclyn Smith: Excellent. What's your background, Shane? What kind of companies have you worked with?

Shane Raubenheimer: I've been privileged enough to work across multiple industries—everything from petrochemical to IT, to digital television, food industry. All different types of applied work, but with the agile philosophy.

Jaclyn Smith: Excellent, a big broad range. I should introduce myself as well. My name is Jaclyn. I am a Senior Product Manager here at Easy Agile, and I look after our Team Rhythm product, which helps teams realize the benefits of being agile. I stumbled there because our whole purpose at Easy Agile is to enable our customers to realize the benefits of being agile.

My product focuses on team and teamwork, and teamwork happens at every level as we know. So helping our customers break down work and estimate work, reflect—which is what we're talking about today—and most importantly, take action to improve their ways of working. I am an agile coach by trade as well as a product manager, and spent about five years in a heap of different industries, both as a consultant like you Shane, and as an in-house coach as well.

The core problem: When retrospectives become checkbox exercises

Jaclyn Smith: All right, let's jump in. My first question for you Shane—I hear a lot that teams get a bit bored with retros, or they face recurring issues in their retrospectives. Is that your experience? Tell me about what you've seen.

Shane Raubenheimer: Absolutely. I think often what should be a positive rollup and action of a sequence of work turns out to normally become a checkbox exercise. There's a lot of latency in the things that get uncovered and discussed, and they just tend to perpetually roll over. It almost becomes a checkbox exercise from what I've seen, rather than the mechanism to actively change what is happening within the team—but more importantly, from influences outside the team.

I think that's where retros fail, because often the team does not have the capability to do any kind of upward or downstream problem solving. They tend to just mull about different ways to ease the issues within the team by pivoting the issues rather than solving them.

I think that's where retros fail, because often the team does not have the capability to do any kind of upward or downstream problem solving. They tend to just mull about different ways to ease the issues within the team by pivoting the issues rather than solving them.

Jaclyn Smith: Yeah, I would agree. Something that I see regularly too is because they become that checkbox, teams get really bored of them. They do them because they're part of their sprint, part of their work, but they're not engaged in them anymore. It's just this thing that they have to do.

It also can promote a tendency to just look at what's recently happened and within their sphere of influence to solve. Whereas I think a lot of the issues that sometimes pop up are things that leadership need to help teams resolve, or they need help to solve. It can end up with them really focusing on "Oh well, there's this one bit in how we do our code reviews, we've got control over that, we'll try to fix that." Or as you say, the same recurring issues come up and they don't seem to get fixed—they're just the same complaints every time.

Shane Raubenheimer: Absolutely. You find ways that you put a band-aid on them just so you can get through to the next phase. I think the problem with that is the impact that broader issues have on teams is never completely solvable within that space, and it's no one else's mandate necessarily to do it. When an issue is relatable to a team, exposing why it's not a team-specific issue and it's more environmental or potentially process-driven—that's the bit that I feel keeps getting missed.

When an issue is relatable to a team, exposing why it's not a team-specific issue and it's more environmental or potentially process-driven—that's the bit that I feel keeps getting missed.

The pressure problem and overwhelming solutions

Jaclyn Smith: Yeah, I think so too. The other thing you just sparked for me—the recurring issue—I think that also happens when the team are under pressure and they don't feel like they have the time to solve the problems. They just need to get into the next sprint, they need to get the next bit of work done. Or maybe that thing that they need to solve is actually a larger thing—it's not something small that they can just change.

They need to rethink things like testing strategies. If that's not working for you, and it's not just about fixing a few flaky tests, but you need to re-look at how you're approaching testing—it seems overwhelming and a bit too big.

Shane Raubenheimer: Absolutely. Often environmental issues are ignored in favor of what you've been mandated to do. You almost retrofit the thing as best you can because it's an environmental issue. But finding ways to expose that as a broader-based issue—I think that should be the only output, especially if it's environmental and not team-based.

The problem of forgotten action items

Jaclyn Smith: Something I've also seen recently is that teams will come up with great ideas of things that they could do. As I said before, sometimes they're under pressure and they don't feel they have the capacity to make those changes. Sometimes those actions get talked about, everyone thinks it's a wonderful idea, and then they just get forgotten about. Teams end up with this big long backlog of wonderful experiments and things that they could have tried that have just been out of sight, out of mind. Have you seen much of that yourself?

Shane Raubenheimer: Plenty. Yes, and often teams err on the side of what's expected of them rather than innovate or optimize. I think that's really where explaining the retrospective concept to people outside fully-stacked or insular teams is the point here. You need, very much like in change management, somebody outside the constructs of teams to almost champion that directive—the same way as you would do lobbying for money or transformation. It needs to be taken more seriously and incorporated into not just teams being mini-factories supporting a whole.

You transform at a company level, you change-manage at a company level. So you should action retrospective influences in the same way. Naturally you get team-level ones, and that's normally where retrospectives do go well because it's the art of the possible and what you're mandated to do. I think bridging the gap between what we can fix ourselves and who can help us expose it is a big thing.

I see so much great work going to waste because it simply isn't part of the day job, or should be but isn't.

You transform at a company level, you change-manage at a company level. So you should action retrospective influences in the same way.

Making action items first-class citizens

Jaclyn Smith: Yeah, absolutely. I know particularly in the pre-Covid times when we were doing a lot of retros in person, or mostly in person with stickies on walls, I also found even if we took a snapshot of the action column, it would still end up on a Confluence board or something somewhere and get forgotten about. Then the next retro comes around and you sort of feel like you're starting fresh and just looking at the last sprint again. You're like, "Oh yeah, someone raised that last retro, but we still didn't do anything about that."

Shane Raubenheimer: I think Product Owners, Scrum Masters, or any versions of those kinds of roles need to treat environmental change or anti-pattern change as seriously as they treat grooming work—the actual work itself. Because it doesn't matter how good you are if the impediments that are outside of your control are not managed or treated with the same kind of importance as the actual work you're doing. That'll never change, it'll just perpetuate. Sooner or later you hit critical mass. There's no scenario where your predictability or velocity gets better if these things are inherent to an environment you can't control.

Product Owners, Scrum Masters, or any versions of those kinds of roles need to treat environmental change or anti-pattern change as seriously as they treat grooming work—the actual work itself.

Jaclyn Smith: Yeah, that's true. We've talked about action items being first-class citizens and how we help teams do that for that exact reason. Because a retro is helpful to build relationships and empathy amongst the team for what's happening for each of them and feel a sense of community within their team. But the real change comes from these incremental changes that are made—the conversations that spark the important things to do to make those changes to improve how the team works.

That action component is really the critical part, or maybe one of two critical parts of a retro. I feel like sometimes it's the forgotten child of the retro. Everyone focuses a lot on engaging people in getting their ideas out, and there's not as much time spent on the action items and what's going to be done or changed as a result.

Beyond team-level retrospectives

Shane Raubenheimer: Absolutely, consistently. I think it's symptomatic potentially of how retros are perceived. They're perceived as an inward-facing, insular reevaluation of what a team is doing. But I've always thought, in the same way you have the concept of team of teams, or if you're in a scaled environment like PI planning, I feel retrospectives need the same treatment or need to be invited to the VIP section to become part of that.

Because retrospectives—yes, they're insular or introspective—but they need to be exposed at the same kind of level as things like managing your releases or training or QA, and they're not.

Jaclyn Smith: Yeah, I think like a lot of things, they've fallen foul of the sometimes contentious "agile" word. People tend to think, "Oh retros, it's just one of those agile ceremonies or agile things that you do." The purpose of them can get really lost in that, and how useful they can be in creating change. At the end of the day, it's about improving the business outcomes. That's why all of these things are in place—you want to improve how well you work together so that you can get to the outcome quicker.

At the end of the day, it's about improving the business outcomes. That's why all of these things are in place—you want to improve how well you work together so that you can get to the outcome quicker.

Shane Raubenheimer: Absolutely. Outcome being the operative word, not successfully deploying code or...

Jaclyn Smith: Or ticking the retro box, successfully having a retro.

Shane Raubenheimer: Yeah, exactly. Being doing agile instead of being agile, right?

Expanding the scope of retrospectives

Jaclyn Smith: One hundred percent. It also strikes me that there is still a tendency for retros to be only at a team level and only a reflection of the most recent period of time. So particularly if a team are doing Scrum or some version of Scrum with sprints, to look back over just the most recent period. I think sometimes the two things—the intent of a retro but also the prime directive of the retro—gets lost.

In terms of intent, you can run a retro about anything. Think about a post-mortem when you have an incident and everyone gets together to discuss what happened and how we prevent that in the future. I think people forget that you can have a retro and look at your system of work, and even hone in on something like "How are we estimating? Are we doing that well? Do we need to improve how we're doing that?" Take one portion of what you're working on and interrogate it.

You can run a retro about anything. I think people forget that you can have a retro and look at your system of work, and even hone in on something like "How are we estimating? Are we doing that well? Do we need to improve how we're doing that?" Take one portion of what you're working on and interrogate it.

Understanding anti-patterns

Shane Raubenheimer: Absolutely. You just default to "what looks good, what can we change, what did we do, what should we stop or start doing?" That's great and all, but without some kind of trended analysis over a period of time, you might just be resurfacing issues that have been there all along. I think that's where the concept or the lack of understanding of anti-patterns comes in, because you're measuring something that's happened again rather than measuring or quantifying why is it happening at all.

I think that's the big mistake of retros—it's almost like an iterative band-aid.

I think that's the big mistake of retros—it's almost like an iterative band-aid.

Jaclyn Smith: Yeah. Tell me a little bit more about some of the anti-patterns that you have seen or how they come into play.

Shane Raubenheimer: One of them we've just touched on—I think the buzzword for it is the cargo cult culture for agile. That's just cookie-cutting agile, doing agile because you have to instead of being agile. Literally making things like your stand-up or your review or even planning just becomes "okay, well we've got to do this, so we've ticked the box and we're following through."

Not understanding the boundaries of what your method is—whether you like playing "wagile" or whether you're waterfall sometimes, agile at other times, and you mistake that variability as your agility. But instead, you don't actually have an identity. You're course-correcting blindly based on what's proportionate to what kind of fire you've got in your way.

Another big anti-pattern is not understanding the concept of what a team culture means and why it's important to have a team goal or a working agreement for your team. Almost your internal contracting. We do it as employees, right?

I think a lot of other anti-patterns come in where something's exposed within a team process, and because it's not interrogated or cross-referenced across your broader base of teams, it's not even recognized as a symptom. It is just a static issue. For me, that's a real anti-pattern in a lot of ways—lack of directive around what to do with retrospectives externally as well as internally. That's simply not a thing.

A lot of other anti-patterns come in where something's exposed within a team process, and because it's not interrogated or cross-referenced across your broader base of teams, it's not even recognized as a symptom. It is just a static issue. For me, that's a real anti-pattern in a lot of ways—lack of directive around what to do with retrospectives externally as well as internally.

Jaclyn Smith: Yeah, I think that's a good call-out for anyone watching or listening. If you're not familiar with anti-patterns, they're common but ineffective responses to recurring problems. They may seem helpful initially to solve an immediate problem, but they ultimately lead to negative outcomes.

Shane, what you just spoke about there with retrospectives—an example of that is that the team feel disengaged with retrospectives and they're not getting anything useful out of it, or change isn't resulting from the retrospectives. So the solution is to not hold them as frequently, or to stop doing them, or not do them at different levels or at different times. That's a really good example of an anti-pattern. It does appear to fix the problem, but longer term it causes more problems than it solves.

Another one that I see is with breaking down work. The idea that spending time together to understand and gain a shared understanding of the work and the outcome that you need takes a lot of time, and breaking down that work and getting aligned on how that work is going to break down on paper can look like quite an investment. But it's also saving time at the other end, reducing risk, reducing duplication and rework to get a better outcome quicker. You shift the time spent—development contracts because you've spent a little bit more time discovering and understanding what you're doing.

A common anti-pattern that I see there is "we spent way too long looking at this, so we're going to not do discovery in the same way anymore," or "one person's going to look at that and break it down."

The budget analogy

Shane Raubenheimer: I always liken it to your budget. The retrospective is always the nice shiny holiday—it's always the first to go.

I always liken it to your budget. The retrospective is always the nice shiny holiday—it's always the first to go.

Jaclyn Smith: It's the contractor.

Shane Raubenheimer: Yeah. It's almost like exposing stuff that everybody allegedly knows to each other is almost seen as counterintuitive because "we're just talking about stuff we all know." It often gets conflated into "okay, we'll just do that in planning." But the reality is the concept of planning and how you amend what you've done in the retrospective—that's a huge anti-pattern because flattening those structures from a ceremonies perspective is what teams tend to do because of your point of "well, we're running out of daylight for doing actual development."

But it's hitting your head against the wall repeatedly and hoping for a different outcome without actually implying a different outcome. Use a different wall even. I think it's because people are so disillusioned with retrospectives. I firmly believe it's not an internal issue. I believe if the voices are being heard at a budgeting level or at a management level, it will change the whole concept of the retrospective.

Solution 1: Getting leadership buy-in

Jaclyn Smith: I like it, and that's a good thread to move on to. So what do we do about it? How do we help change this? What are some of the practical tips that people can deploy?

Shane Raubenheimer: A big practical tip—and this is going to sound like an obvious one—is actual and sincere buy-in. What I mean by that is, as a shareholder, if I am basing your performance and your effectiveness on the quality and output of the work that you're promising me, then I should be taking the issues that you're having that are repeating more seriously.

Because if you're course-correcting for five, six, or seven sprints and you're still not getting this increasing, predictable velocity, and if it's not your team size or your attitude, it's got to be something else. I often relate that to it being environmental.

Buying into the outputs for change the same way as you would into keeping everyone honest, managing budgets, and chasing deadlines—it should all be part of the same thing. They should all be sitting at the VIP table, and I think that's a big one.

Buying into the outputs for change the same way as you would into keeping everyone honest, managing budgets, and chasing deadlines—it should all be part of the same thing. They should all be sitting at the VIP table.

Solution 2: Making patterns visible

Jaclyn Smith: I think so too. Something that occurs to me, and it goes back to what we were talking about right at the beginning, is sometimes identifying that there's a pattern there and that the same thing keeps coming up isn't actually visible, and that's part of the problem, right?

I know some things we've been doing in Easy Agile TeamRhythm around that recently, attempting to help teams with this. We've recently started surfacing all incomplete action items in retrospectives so people can see that big long list. Because they can convert their action items to Jira items or work items, they can also see where they've just been sitting and languishing in the backlog forever and a day and never been planned for anything to be done about them.

We've recently started surfacing all incomplete action items in retrospectives so people can see that big long list. Because they can convert their action items to Jira items or work items, they can also see where they've just been sitting and languishing in the backlog forever and a day and never been planned for anything to be done about them.

We've added a few features to sort and that kind of thing. Coming in the future—and we've been asked about this a lot—is "what about themes? What about things that are bubbling up?" So that's definitely on our radar that will be helpful.

I think that understanding that something has been raised—a problem getting support from another team, or with a broken tool or an outdated tool that needs to be replaced in the dev tooling or something like that—if that's been popping up time and time again and you don't know about it, then even as the leader of that team, you don't have the ammunition to then say "Look, this is how much it's slowed us down."

I think we live in such a data world now. If those actions are also where the evidence is that this is what needs to change and this is where the barriers are...

Solution 3: The power of trend analysis

Shane Raubenheimer: Certainly. I agree. Touching on the trend analytics approach—we do trend analysis on everything except what isn't happening or what is actually going wrong, because we just track the fallout of said lack of application. We don't actually trend or theme, to your point.

We do trend analysis on everything except what isn't happening or what is actually going wrong, because we just track the fallout of said lack of application.

We theme everything when we plan, yet somehow we don't categorize performance issues as an example. If everybody's having a performance issue, that's the theme. We almost need to categorize or expose themes that are outward-facing, not just inward-facing. Because it's well and good saying "well, our automated testing system doesn't work"—what does that mean? Why doesn't it work?

I think it should inspire external investigation. When you do a master data cleanup, you don't just say "well, most of it looks good, let's just put it all in the new space." You literally interrogate it at its most definitive and lowest level. So why not do the same with theming and trending environmental issues that you could actually investigate, and that could become a new initiative that would be driven by a new team that didn't even know it was a thing?

Jaclyn Smith: Yeah, and you're also gathering data at that point to evidence the problem rather than "oh, it's a pain point that keeps coming up." It is, but it gives you the opportunity to quantify that pain point a little bit as well. I think that is sometimes really hard to do when you're talking about developer experience or team member experience. Even outside of product engineering teams, there are things in the employee experience that affect the ability for that delivery—whatever you're delivering—to run smoothly. You want to make that as slick as possible, and that's how you get the faster outcomes.

Solution 4: The human factor

Shane Raubenheimer: Absolutely. You can never underestimate the human factor as well. If everything I'm doing and every member of my team is doing is to the best of not just their capability, but to the best of the ability in what they have available to them, you become jaded, you become frustrated. Because if you're hitting your head against the same issue regardless of how often you're pivoting, that can be very disillusioning, especially if it's not been taken as seriously as your work output.

If everything I'm doing and every member of my team is doing is to the best of not just their capability, but to the best of the ability in what they have available to them, you become jaded, you become frustrated.

We run a week late for a customer delivery or a customer project, and we start complaining about things like money, budget overspend, over-utilization. But identifying systematic or environmental issues that you can actually quantify should be treated in exactly the same way. I feel very strongly about this.

Solution 5: Breaking down overwhelming action items

Jaclyn Smith: We tend to nerd out about this stuff, Shane, and you're in good company. You've also reminded me—we've put together a bit of a workshop to help teams and people understand how to get the most out of their retrospectives, not just in terms of making them engaging, but fundamentally how to leverage actions to make them meaningful and impactful.

We've spoken a lot about the incremental change that is the critical factor when it is something that's within the team's control or closely to the team's control. That's how you get that expansion of impact—the slow incremental change. We've talked about sometimes those action items seem overwhelming and too big. What's your advice if that's the scenario for a team? What do you see happen and what can they do?

Shane Raubenheimer: I would suggest following the mantra of "if a story is too big, you don't understand enough about it yet, or it's not broken down far enough." Incremental change should be treated in exactly the same way. The "eat the elephant one bite at a time" analogy. If it's insurmountable, identify a portion of it that will make it a degree less insurmountable next time, and so on and so forth.

If we're iterating work delivery, problem-solving should be done in rapid iteration as well. That's my view.

Jaclyn Smith: I like it.

The "eat the elephant one bite at a time" analogy. If it's insurmountable, identify a portion of it that will make it a degree less insurmountable next time, and so on and so forth. If we're iterating work delivery, problem-solving should be done in rapid iteration as well.

Wrapping up: What's next?

Jaclyn Smith: I think we're almost wrapping up in terms of time. What can people expect from us if they join our webinar on July 10th, I believe it is, where we dive and nerd out even more about this topic, Shane?

Shane Raubenheimer: I think the benefit of the webinar is going to be a practical showing of what we're waxing lyrical about. It's easy to speak and evangelize, but I think from the webinar we'll show turning our concepts into actual actions that you can eyeball and see the results of.

With our approach that we took to our workshop, I think people will very quickly get the feeling of "this is dealing with cause and effect in a cause and effect way." So practical—to put that in one sentence, an active showing or demonstration of how to quantify and actually do what we've been waxing lyrical about.

the benefit of the webinar is going to be a practical showing of what we're waxing lyrical about. It's easy to speak and evangelize, but I think from the webinar we'll show turning our concepts into actual actions that you can eyeball and see the results of.

‍Jaclyn Smith: Excellent. That was a lovely summation, Shane. If anyone is interested in joining, we urge you to do so. You can hear us talking more about that but get some practical help as well. There is a link to the registration page in the description below.

I think that's about all we have time for today. But Shane, as always, it's been amazing and lovely to chat to you and hear your thoughts on a pocket of the agile world and helping teams.

Shane Raubenheimer: Yeah, it's always great engaging with you. I always enjoy our times together, and it's been my pleasure. I live for this kind of thing.

Jaclyn Smith: It's wonderful! Excellent. Well, I will see you on the 10th, and hopefully we'll see everyone else as well.

Shane Raubenheimer: Perfect. Yeah, looking forward to it.

Jaclyn Smith: Thanks.

Ready to end the frustration of ineffective retrospectives?

Jaclyn Smith and Shane Raubenheimer also hosted a live, hands-on webinar designed to turn retrospectives into powerful engines for continuous improvement.

In this highly interactive session, they talked about how teams can:

• Uncover why retrospectives get stuck in repetitive cycles
• Clearly capture and assign actionable insights
• Identify and avoid common retrospective pitfalls and anti-patterns
• Get hands-on experience with Easy Agile TeamRhythm to streamline retrospective actions
• Practical tools, techniques, and clear next steps to immediately enhance retrospectives and drive meaningful team improvements.

👉 Watch the recording here.