Easy Agile Podcast Ep.22 The Scaled Agile Framework

"Really enjoyed my conversation with William and Riz, I'm looking forward to implementing their recommendations with our team" - Angad Sethi

In this epsiode I spoke with William Rojas and Rizwan Hasan from Adaptavist about the ways we can enable high performing agile teams:

• The significance of team alignment
• When and where you should be using tools to assist with your team objectives
• Prioritizing what conversations you need to be apart of
• Advice for remote teams

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Thanks William & Rizwan!

Transcript

Angad Sethi:

Good afternoon/evening/morning everyone. How you guys going?

Rizwan Hasan:

Oh, good. Thanks Angad.

William Rojas:

Yeah. How are you?

Angad Sethi:

Yeah, really good. Really, really stoked to be having a chat with you guys. Should we start by introducing ourselves? Riz, would you like to take it?

Rizwan Hasan:

Sure. My name's Riz Hasan, I'm based in Brussels, Belgium. Very newly based here, actually used to be based in New York, not too far from William. We usually used to work together on the same team. My role here at Adaptavist is I'm a team lead for our consulting group in EMEA. So in the European region and in the UK. So day to day for me is a lot of internal management, but also working with customers and my consultants on how our customers are scaling agile and helping them with tool problems, process problems, people problems, all the above.

Angad Sethi:

Yeah. Yeah. Sounds awesome.

William Rojas:

As for myself, William Rojas. I'm actually based out of a little suburban town called Trumble in Connecticut, which is about an hour plus northeast of New York, basically. And as Rez mentioned, yeah, we've worked for a number of years we've worked together, we were running a agile transformation and scaling adoption team for Adaptavist. My new role now is actually I took on a presales principle, basically a presale principle consultant these days. It's actually a new role within Adaptavist, and what we do is we have, actually all of us, I think most of us are all like ex-consultants that support the pre-sales process, and work in between the sales team, and the delivery team, and all the other teams that support our clients at Adaptavist.

Angad Sethi:

Awesome, awesome.

William Rojas:

I help find to solutions for clients and make the proposals and support them through, get them on through delivery.

Angad Sethi:

I'm Angad, I'm a software developer and I'm working on Easy Agile programs and Easy Agile roadmaps, two of the products we offer for the Atlassian marketplace. We're super excited to speak to you guys about how your teams are operating in, like what's a day to day. Riz, would you like to answer that?

Rizwan Hasan:

Sure. Yeah. So apart from like the internal management stuff, I think what's particular to this conversation is how we walk clients through how to navigate planning at scale, right?

Angad Sethi:

Yeah.

Rizwan Hasan:

I'm working with a client right now who's based in the states, but they're acquiring other software companies left and right. Which I think is also a trend that's happening within this SaaS ecosystem. And when that happens, they're trying to bring all that work in together. So we're talking through ways of how to visualize all that in an easy way that isn't really too much upfront heavy with identifying requirements or understanding what systems we want to pull in, but more so what do you want to pull in? So really right now, in this phase of the data that I'm working with this client, it's really just those initial conversations about what are you planning? What are you doing? What's important to you? So it's a lot of these conversations about that.

Angad Sethi:

And so you mentioned it's a lot of internal management. Are some of your clients fellow workmates, or are they external clients?

Rizwan Hasan:

They're mostly internal because I manage a team, so I have different people who are working on different types of projects where they might be doing cloud migrations. They might be doing some scripting work. In terms of services, we cover everything within the Atlassian ecosystem, whether it be business related, process related, tool related. So it's a big mix of stuff at all times.

Angad Sethi:

Cool. And is it usually like you're speaking to all the team leads, and giving them advice on agile ceremonies, and pushing work through pipelines and stuff?

Rizwan Hasan:

Yeah, actually, so a story of when I first moved to Brussels, because we've... So professional services started at Adaptavist in the UK, and this was maybe like seven-eight years ago, and it's expanded and myself and William were part of like the first group of consultants who were in North America. That expanded really quickly, and now that we're in EMEA, it's almost like a different entity. It's a different way of working, and a lot of leadership has moved over to North America, so there's new systems and processes and ceremonies and then all that's happening. But because of time zones there's a conflict.

So what I started to do when we got here was to reintroduce some of those habits and consistent conversations to have, to really be much more on a better planning cadence. So interacting with people who would be, say, bringing work to delivery in presale. So folks who are, who work similar to William's capacity over here in this region, and then also project managers who would be responsible for managing that work. Right? So on the equivalent of like a scrum master on an engagement or like an RTE on a big engagement. Right?

Angad Sethi:

Yep. Yep. That's awesome. Just one thing I really liked was your terminology. You used conversations over ceremonies or speaks about the agile mindset in that sense, where you're not just pushing ceremonies on teams, where you actually embody being agile. Well, I'm assuming you are from your conversation, but I guess we'll unpack that. What about you, William? What's your [crosstalk 00:06:32]

William Rojas:

I was going to say, one of the things that's interesting challenge that we face, because Adaptavist has an entire branch that does product development and there are product developers, and product managers, and product marketing, and all sorts of things like that. And they set plans and they focus, deliver and so forth, as you would expect a normal product organization to do. On the consulting side, one of the things that's very interesting is that a lot of our, like we have to answer to two bosses, right? Like our clients come in and say, "Hey, we need this," and we have to support them. In the meantime, we have a lot of internal projects, internal procedures and processes and things that we want do as a company, as a practice, but at the same time, we still need to answer to our clients.

Angad Sethi:

I see.

William Rojas:

So that's actually one of the interesting challenges that from an agile perspective, we're constantly facing having to balance out between sometimes conflicting priorities. And that is definitely something that, and although consulting teams at different levels face this challenge. Right?

Angad Sethi:

Yeah.

William Rojas:

So as Riz mentioned, we're constantly bringing in more work and like, "Okay, we need you to now adjust and re-plan to do something different, then manage." Yes. It's an ongoing problem that's just part of this part of this world kind of thing.

Angad Sethi:

Yeah. Okay. I see. And so if I heard that correctly, so it's, I guess you're constantly recommending agile processes, but you may not necessarily get to practice it?

William Rojas:

But more so we're both practicing for ourselves as well as trying to tell our clients to practice it or trying to adjust.

Angad Sethi:

I see, yeah.

William Rojas:

You know, a client comes in with needs and says, "Okay, now we have to re-plan or teach them how to do it, or re-accommodate their new emerging priorities as well." So we ultimately end up having to practice agile with and for our clients, as well as for ourselves. It's that constant rebalancing of having to weave in client needs into internal needs, and then the constant re-priority that may come as a result of that.

Angad Sethi:

Yeah.

William Rojas:

And then we're constantly looking for like, how do we make this thing more efficient, more effective? How do we really be lean about how we do the work and so forth? That is definitely one thing that we practice. We try to practice that on a daily basis.

Angad Sethi:

Yeah. And I guess that's a very, a tricky space to be... not a tricky space. It can be tricky, I guess, but adding to the trickiness is remote work. Do you guys have a lot of clients who have transitioned to remote work? And I don't know, has it, has it bought to light problems, which can be a good thing, or like what's your experience been?

William Rojas:

So that's interesting because so I've been doing consulting for over a couple decades, and traditionally, so I've done a lot of that, that travel warrior, every week you go travel to the client to do your work, you travel back and you do that again next week, and you do that month after month. In coming to Adaptavist, Adaptavist has historically always been a remote consulting company. So five years ago it was like, wow, we would go to clients saying like, "Okay, we need you to do this." And we're like, "Yeah, we can deliver that. And no, we don't need to, you know. We may come in and do a onsite visit to introduce ourselves, but we can deliver all this work remotely." So we've always had that history.

Angad Sethi:

Okay.

William Rojas:

But nonetheless, when COVID hit and everybody went remote, we definitely experienced a whole new set of companies were now suddenly having to work remotely, and having to establish new processes and practices that basically forced them to be remote. And I think we've had the fortune of in a sense, having always been-

Angad Sethi:

Yep, remote start.

William Rojas:

... S8's.

Angad Sethi:

Yeah.

William Rojas:

I know whenever we bring on people into the company, into consulting particular, that's one of the things we always point out. Remote work is not the same as being in the office. It has its ups and downs. But we've always had that benefit. I think we've been able to assist some of our clients, like, This is how this is how it's done, this is how we do it." So we've been able to teach by example type of thing for some of the clients.

Angad Sethi:

There you go.

William Rojas:

Yeah.

Angad Sethi:

Awesome. That was actually going to be my next question is what's the working structure at Adaptavist and what sort of processes? I'm sure that it's a big company and therefore there'd be tools and processes particular to teams in themselves. Just from your experiences, what are some of the processes or tools you guys are using?

Rizwan Hasan:

So, in terms of planning and work management, because we started off as a remote first company, and since COVID, business is good. I'll be frank there, it's been good for us because we specialize in this market. We've had a huge hiring spurt in all these different areas, and one thing that I noticed internally, as well as problems that... I wouldn't say problems, but a trend that we're seeing with a lot of other clients is that because of this remote push, and the need for an enterprise to be able to give the teams the tools they need to do their work, there's a lot more flexibility in what they can use, which has pros and cons.

On the pro side, there's flexibility, the teams can work the way they want. On the con side, administration might be difficult, alignment might be difficult. So we're seeing a lot of that with customers and ours. So we're almost going on this journey with customers as we're scaling ourselves, and learning how to navigate this new reality of working in a hybrid environment.

William Rojas:

I think in terms of some of the tooling and so forth that we get to do. So we obviously internally we have, we're pretty, pretty much in Atlassian. Atlassian stack, that is very much how we work every day. All our work is using Atlassian tools. All our work is tracked, all our client work is tracked in JIRA, all our sales work, basically everything we do, we use JIRA and Confluence, we're really big on Confluence. We have a lot of customizations we've done to our instance over the years, things that we just have developed, and so that's internal.

I think the other aspect is often, depending on the client that comes to us and the type of work that we're doing for that client, then the types of tools that we use can pretty much run the full gamut. We have a lot of Atlassians, we do a lot of work in JIRA with our clients, like work in Confluence. Sometimes we're working on helping them scale, so we bring on some of the add-on to support some of the scaling practices within to support JIRA. We'll do a lot of JSM work. We do often DevOps work, and then we'll bring on a lot of the DevOps tool sets that you would expect to find, so things to support delivery pipelines.

So it really depends quite a bit on the client. We even do some agile transformation work. And then there, we do some a lot of custom build things, practices and so forth. And we bring in surveys and tools that we've been able to develop over the years to support that particularly. So a lot of the tools often are dictated by what the client and the specific engagement call for.

Angad Sethi:

In my personal experience recently with COVID, I find myself in a lot of meetings, we are experimenting with, with Async decision making. Have you experimented with Async decision making processes yet?

Rizwan Hasan:

I'll start by saying I hate meetings. I think most meetings are a waste of time, and I tell my team this. And I'm like, "If we don't need to meet, like we're not going to meet."

Angad Sethi:

Yeah. Awesome.

Rizwan Hasan:

And I think that really comes. Yeah, awesome, for sure. Awesome.

Angad Sethi:

I love it.

Rizwan Hasan:

But it comes down to really is when you do meet, are you having the right conversation? And I think a key component being like an agile team, quote-unquote, is you have an understanding of what we all are doing collectively and what the priorities are. Which is tough to actually get. So when we talk about like asynchronous decision making, with a team that has some degree of understanding of what priorities are, what goals are, it gets easier. And you can have more low impact interactions with people.

So we use Slack a lot and we have a lot of internal bots on our Slack to be able to present information and collect feedback at asynchronous times, because there's voting features, there's places where you can comment. And I think when we talk about teams that are growing across the globe and also time zones and flexible working, that's a real thing now. There's a practical way of how to do that, that we're starting to dig into what does that look like?

Angad Sethi:

Do you find yourself in a million Slack groups?

Rizwan Hasan:

Yep.

Angad Sethi:

Yep. You do. Do you see any extra hurdles you've got to skip because of that? Because you maybe, do you find yourself hopping from conversation to conversation, whereas it would just be easier if everyone was in the same conversation? Does that happen a bit?

Rizwan Hasan:

Yeah. Yeah. All the time.

Angad Sethi:

I hear you, yeah, there you go. Okay. Cool.

William Rojas:

But I would say we have a lot of impromptu. I think we do have a lot of impromptu meetings. And sometimes we may be in a Slack typing away. It says, you know what? [crosstalk 00:17:29]

Angad Sethi:

Just jump in a huddle.

William Rojas:

Into Zoom and then let's chat or Slack conversation, and then just face to face conversation, and then just address it then and there. But I think we have been looking at, it's almost like I think a balance between the time spent on the meeting, and the amount of people that need to be in the meeting, and the benefit and value that comes out of that meeting. And a daily meeting where work was people would pick up work or support from a sales perspective. And it was very, very much necessary as per part of the work coming into the consulting pipeline. But it felt very inefficient.

So that's one of the means, for example, we did away with, and it's now a completely asynchronous process, by which work comes in and it gets allocated, people pick it up, people support it, we deliver things, we track where things are and so forth. And we now use all of that is basically all done through Slack. So we did away with all the meetings around, "Hey, who can help with this?" But meantime, we have another meeting where we're trying to get people on projects. And that is very much a, we need to negotiate on that often. So that's a meeting that's still very much done.

Angad Sethi:

Yep.

William Rojas:

Everybody comes in, we all talk, we decide what we need to get done. People balance back and forth. So that trade off I think is really important to really understand what, there are meetings that are necessary, very valuable, and they should remain. And there's ones that really a Slack is a much better mechanism to be able to make those kind of decisions

Angad Sethi:

Yeah. Very true. Yeah. And does it well, sorry, firstly, pardon the location change. I'm sitting right next to the router now, so hopefully the iPhone holds. What sort of a scale are we speaking about here in your Slack? The reason I ask is with larger organizations, it can be harder to scale. Therefore I'm just trying to get a gauge of what scale your Slack is at.

Rizwan Hasan:

So we just hit, we are just over the 500 mark, that'd be in terms of employees. With basically our general, which seems to be, I think, I don't want to say universal, but the standard across any organization that has Slack general as the best indicator of how many people you have logged on. So we're just about the 500 mark, which I would say is probably around mid-size, but it's definitely getting to the point where we're starting to see, it's almost a little bit too much in order to disseminate information, find their information, etc.

We're actually partners with Slack also. So we work with them pretty closely on some opportunities. [crosstalk 00:20:39] Yeah, exactly. And we're starting to talk with customers also about the same problem, about how much is too much, and when do you start to form communities around people that are delivering the same type of value. So those conversations are more aligned and there's not just a whole lot of chatter and people get confused, like when they read Slack and like, "Oh, is this the priority now? Or am I supposed to be doing this or change in process?" That communication is harder now, I think, really. And this is where a lot of folks, I think, who are moving to this remote environment are struggling with, is that alignment communication.

Angad Sethi:

Yeah. Very true.

William Rojas:

And it is, I would say fairly organic, like our channel proliferation. We do have, I would think even for company of our size, we're pretty loose about how channels get proliferated, who gets to create them, what they're for and so forth. But then it gives the flexibility of based upon your interests or the context of what you need to communicate on, then you can either join a channel that supports it or create a channel if necessary to support it. So it is, in that sense, pretty organic. But it is true that there are hundreds, if not thousands of Slack channels that we have, and so kind of staying like which one should you be on, is definitely one of our biggest challenges.

Angad Sethi:

Yeah. Well, that just blows my mind just because like 500 people on a Slack. Our whole company is 35 people and I'm pulling my hair out being in too many Slacks. So well A, that blows my mind.

William Rojas:

It does allow us, for example, to have client specific Slack channels. So anybody, if you need to talk about, if you're working on a particular account, you're working for a client, then there's a channel for that. And if you're working on another client, there's another channel. The thing I find helpful about it is that it gives you that context of if I want to communicate with so and so, if I communicate with Riz on a particular account, I will go to the account channel. If I want to talk to Riz one-on-one, I go to a one-on-one chat.

Angad Sethi:

I see, yep, the flexibility.

William Rojas:

So we do have that benefit of where to put the information. But it does mean that I have probably over a hundred channels in my roster of things that I follow, and I'm always behind.

Angad Sethi:

Yeah.

William Rojas:

Well, yeah. So the next level of it is, then you begin to prioritize which channels should I really be notified about, and which ones are most important. I want to track those. And I try to keep that list to a minimum in terms of unread messages, and the stuff that I try to get to, and I'm bored and I have nothing else to do so, but yeah.

Rizwan Hasan:

I've been leaving a lot of channels too. I've been just really cutting the cord with some channels. You know, I had some motivation to really help out here, but I just can't and it's just too much noise. And just got to cut the cord and be like, if it's empty, there's no conversation happening or if it's slow, then move on.

Angad Sethi:

Yep.

William Rojas:

We also have the ability to, you can get added back in. So sometimes you leave and then somebody will put you back in, like, "I need you to talk about this." But it is pretty organic. I know we do leave it up to the individual to decide how best to manage that.

Rizwan Hasan:

Yeah.

Angad Sethi:

That's awesome.

Rizwan Hasan:

We had a instance today, actually, where there was an old, it was basically a sales opportunity, a customer who had reached out to us for a certain ask, and we hadn't heard from them for months, like eight-nine months. And someone posted, someone who I'm pretty close with on our sales team posted, "Hey, this is kicking back up again, but I don't have the capacity." And I just left immediately as I saw that message. I was like, "I can't help out. Sorry."

Angad Sethi:

Yeah. The old so-and-so has left the group is a bit of a stab in the heart, but yeah.

Rizwan Hasan:

Yeah.

Angad Sethi:

We will get over it. Just coming back to a point you mentioned, Riz, you said you used the words, alignment and communication. Both of you when consulting with clients, are those the two main themes you guys like to base your recommendations around?

Rizwan Hasan:

I'll give you a very consulting answer and say it depends.

Angad Sethi:

Yeah.

Rizwan Hasan:

But when we engage with a customer, one of the toughest parts of our job is understanding if there is even alignment in the group of people that we're talking to as well, because at the scale of projects that sometimes we work with, we have like 20 to 25 people on a call. And of all of those people, they may have different motivations or objectives of what they're wanting with their engagement with us. So I would say, that's primarily what's driving what we're trying to find out, what we're trying to do with them is get some alignment between the group and ourselves, and communicating that is not always easy.

Angad Sethi:

Yeah.

William Rojas:

Let's say, adding on what Riz, that also depends quite a bit on the specific engagement with that client. So in particular, if the engagement, because if an engagement is like, "Get me onto the cloud." Okay. You know, come in. Often there's much better alignment for something like that. If the engagements are more about, "Hey, help us scale agile, help us get better at how we deliver." Then the need for alignment, the need to make sure that we're all communicating correctly, we all understand, we all come to the meeting with the same objectives and so forth, is so much more critical.

Angad Sethi:

Yeah.

William Rojas:

So in those kind of engagements, we're constantly realigning. Because it's not even like we had the alignment. It's like yeah. Okay. We have it, next week it's gone. We got to go back and get it again. So that keeping, making sure that everybody's marching towards the same set of objectives, defining what those objectives are, letting them evolve as appropriate and so forth, all that becomes so much more critical.

Angad Sethi:

Yeah.

William Rojas:

And that's where the tools, that's where things like JIRA and then again, like how do we scale? How do we show what everybody's doing? And so forth, that's where it becomes that much more important. And in those kind of engagements, the tooling becomes essential. Not that the tooling's going to answer it, but the tooling becomes a way by which it helps us communicate, yeah. This is what we all agree we're going to do. Okay. The tool says so because that's the decision we've made.

Angad Sethi:

Yeah.

Rizwan Hasan:

It's really interesting that you say cloud migration, William, like when you say, "Okay, I'm moving to cloud, we know what the alignment is," but even then, I'm finding is that, especially within the Atlassian ecosystem, because that's what we're exposed to all the time, but when we're moving data from a completely old infrastructure to something brand new, it's not going to be the same. And you have folks who are thinking that, "Oh, we're just going to be taking all this stuff from here and putting it over there." But what usually doesn't come along with it is that you're going to have to also change the way you work slightly. There's going to be changes that you're not accounting for.

And that's where the alignment conversation really is important because we work with small companies who understand, okay, moving to the cloud will be completely different. We also work with legacy organizations like financial institutions that have a lot of red tape, and process, and security concerns, and getting that alignment and understanding with them first of what this means to move to a completely different way of working, is also part of that conversation. So it's a constant push and pull with that.

Angad Sethi:

Yeah, yeah. It's really heartwarming to hear the two of you deal with the JCMA, which is the geo cloud migration system.

Rizwan Hasan:

Quite a bit, yeah.

Angad Sethi:

That's awesome, because yeah, that's something we are working on currently as well. So I'll end with a super hard question and I'll challenge you guys to not use the word depends in there. And the question is the number one piece of advice for remote teams practicing agile. Start with you, Riz.

Rizwan Hasan:

Get to know each other.

Angad Sethi:

Yeah, okay.

Rizwan Hasan:

Keep it personal. I think one of the hardest things about this new reality is making that connection with someone, and when you have that, that builds trust, and when you have trust, everything's a lot easier. So I'd say that. People really aren't... The enemy. That's not the right word, but work shouldn't be a conflict. It should be more of like a negotiation, and if you trust each other, it's a lot easier to do that.

Angad Sethi:

Yeah.

Rizwan Hasan:

So yeah.

Angad Sethi:

That's awesome.

William Rojas:

It really is.

Angad Sethi:

I'm going to definitely take that back with me.

William Rojas:

Yeah. And just if I could quickly add to that. That's like looking for ways how to replace the standing around by the, having a cup of coffee. How do you replace that in a remote setting?

Rizwan Hasan:

Yeah.

Angad Sethi:

Yeah.

William Rojas:

How do you still have that personal interaction that maybe there's an electronic medium in between, but there's still sort of that personal setting. I think that's one of the things you're looking for. Because yeah, it is very much about trust. And I think to that, I would also add, back to the alignment. Right? Because in some ways that strong interaction helps build and maintain the alignment, because often it's not so much that you get alignment is that you stay aligned.

So it is this constant, and having those interactions, having that trust and so forth, is what in a sense allows us to stay aligned. Because we know each other, we know how to help each other, we support each other, so we stay in alignment. So the trust and so forth are a good way to help build and maintain the alignment itself that you're looking for. That's absolutely. In remote world, you don't have the benefit of seeing each other, the whiteboard, all those things are not the same.

Angad Sethi:

Very true. Getting cup a coffee, yep.

William Rojas:

But we still need to stay in sync with what needs to get done. That's so important.

Angad Sethi:

Very true. And so would you guys want to drop any names of tools you're using to facilitate that trust between team members in a remote setting?

William Rojas:

So I would say, like I mentioned from my role, one of the things that we do is in the presales area, we support some of our larger accounts, almost as more of like a solution account manager, per se. So we come in and help make sure that the client is getting the solution that is meant to be delivered. So we work with the delivery teams, we work with the client, we sit in between.

There's one large client that we've been working on for years now, and we basically, to the point that they're moving towards some flavor of safe. That I wouldn't call it fully safe, but they do have a lot of safe practices, but they do PI planning, and so we come in and join the PI planning. That's actually one of the, like I said, how do you stay alive?

Angad Sethi:

That circle. Yeah. [crosstalk 00:33:15]

William Rojas:

You pull up your program definition, you look at what features you want to deliver in the PI, who's going to deliver that feature in the PI, and then in your readout, go back to the tool and say, "Look, this is what we've agreed to." Others can ask questions and so forth, and constantly going back to... For example, just last week, we're doing now sprint planning and saying, "Actually, okay, this feature's going to drag on another sprint. Let me go back and readjust in," this client is using the Easy Agile programs. The original plan of saying this features not going to be, not two sprints, but the three sprints instead, for example.

So that habit of getting into using the tool to communicate what we decided and what we just had to make changes to. So it becomes this, a communication vehicle, it's really important. Yeah, they use programs, they use the roadmap piece of programs to help them do their PI planning, and stay in sync with what it is that ultimately gets communicated out at the end of PI. And then during the sprints of the PI itself, and it's very helpful for them. Again, there's I think they have seven trainings, and they all use that to help stay in sync, stay aligned.

Angad Sethi:

Awesome. Awesome.

William Rojas:

One other quick thing I'll say is, I think there will be, some of where we've gone will now become status quo, become permanent. So I think that this has been as shift across the market, across the industry, across company, how people work. So the idea of remote work, the idea of using tooling to really establish communication, and help facilitate communication, all that, while it's been around, I think the big difference is now everybody, like you have no choice. Everybody has to do it.

Angad Sethi:

Has to. Yeah.

William Rojas:

And I think we've definitely seen a big shift across the entire industry because of that. That will now solidify and let's see what the next level brings. But I definitely think that we've reached a new stage of maturity and so forth pretty much globally, which is pretty cool.

Angad Sethi:

Yeah.

Rizwan Hasan:

Yeah.

Angad Sethi:

Yeah, it is. Thank you guys. I won't keep you too long. I think, has the sun set there, Riz? I can see the reflection going dark.

Rizwan Hasan:

Yeah. It is getting there. Yeah, for sure.

Angad Sethi:

Yeah. Yeah. I won't hold you guys for too long.

Rizwan Hasan:

All good.

Angad Sethi:

But thank you so much for the conversation. I honestly, I took a lot away from that. And yeah, I hope I can add you guys to my LinkedIn. I would love to be in touch still.

William Rojas:

Definitely.

Rizwan Hasan:

Yeah, sure.

Angad Sethi:

Yeah. Trying to establish a point of contact, not to add to one of your Slack channels, but yeah. Just so that we can be in conversation regarding the product and improving it.

Rizwan Hasan:

Yeah, sure. And we have a partner management channel. I know we've been talking to Haley a little bit.

Angad Sethi:

Awesome.

Rizwan Hasan:

She was reaching out, that's about some other stuff.

Angad Sethi:

Beautiful.

Rizwan Hasan:

Yeah, happy to. We engage with your product and it's in our white papers too, and we're going to put out another white paper this year where we're going to talk about Easy Agile too. So yeah. We'll stay in touch.

Angad Sethi:

Cool.

William Rojas:

I just gave you, so my LinkedIn is under a different, my LinkedIn is not with my work email. Because that way I can keep the same account place to place.

Angad Sethi:

Sounds good.

William Rojas:

Yeah. You can look me up on LinkedIn with that.

Angad Sethi:

Wicked awesome. Thanks guys.

William Rojas:

Awesome. All right.

Angad Sethi:

Have a good day.

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.

In this episode, we dive deep into the challenges of aligning teams with strategic goals across organisations of all sizes. From fast-growing startups to large enterprises, teams everywhere struggle with the same fundamental issue: translating high-level objectives into actionable work that drives real value.

Our guest Andreas Wengenmayer, Practice Lead for Enterprise Strategy and Planning at catworkx (the #2 Atlassian partner worldwide and #1 in EMEA), shares his 11 years of experience helping organisations bridge the gap between strategic vision and team execution.

Want to see these concepts in action? Andreas and Hayley hosted an interactive webinar where they demonstrated practical techniques for strategic goal alignment using Easy Agile Programs. Watch the recording here→

About Our Guest

Andreas Wengenmayer is the Practice Lead for Enterprise Strategy and Planning at catworkx, one of the leading Atlassian Platinum Solution Partners globally and the #1 in EMEA. With over a decade of hands-on experience helping enterprise teams scale agile effectively, Andreas specialises in bridging the gap between strategy and execution. His work focuses on guiding organisations through complex transformation programs, optimising portfolio planning practices, and helping teams adopt frameworks like SAFe with clarity and purpose. Known for blending pragmatic insight with systems thinking, Andreas brings stories from the field - ranging from fast-moving startups to complex, multinational enterprises.

Transcript

Note: This transcript has been lightly edited for clarity, readability, and flow while preserving the authentic conversation and insights shared.

Recognising the signs - when teams aren't aligned

Hayley Rodd: Awesome to have you here. So I'm going to start with a bit of a reality check. We've worked in organisations across the spectrum from really fast-growing startups to really big enterprises. From your experience, when you walk into a PI planning or quarterly planning session, and I'm sure they're pretty hectic, what are the telltale signs that teams aren't truly aligned on what success looks like?

Andreas Wengenmayer: That's a great question - one I hear frequently. You can imagine, especially post-COVID when teams returned to in-person planning sessions. Back in 2017, we'd have huge arenas with hundreds of people in one place. People are happy to see each other, excited to chat with colleagues from different locations. This became even more pronounced after COVID, when everyone was working from home more frequently. That's a good sign - the mood is positive.

But you also notice some teams under pressure. They'd rather be working on actual deliverables. They know they have to be there, and it takes two full days to complete all the planning. Meanwhile, they're carrying a mental backlog - technical debt, unfinished work from the previous PI, catching up on delayed items.

This is what I often observe: teams get bogged down discussing minor details. People debate specifics, and you can see they're frustrated about something deeper - but they're not addressing the root cause. This creates its own negative momentum and can derail otherwise solid planning sessions.

Teams get bogged down discussing minor details. People debate specifics, and you can see they're frustrated about something deeper - but they're not addressing the root cause. This creates its own negative momentum and can derail otherwise solid planning sessions.

Sometimes you have to step in and ask what's really underneath. What's the actual cause? People say, "Yeah, I have to be here because that's the format, but I'm not engaged." Maybe it didn't work well in the past and there's lingering skepticism.

The prevailing attitude then becomes: "This isn't really collaborative. Leadership plans from the top anyway. The outcomes are predetermined - here's the plan, just make it work and update your boards." When people feel they can't meaningfully contribute or influence direction, they simply go through the motions.

My favourite example happens at the end when teams must formulate their objectives. It becomes a box-checking exercise - create something that satisfies the coach or Release Train Engineer so everyone can "get back to real work."

What good alignment actually looks like

Hayley Rodd: You've touched on so many things there. I can imagine walking into that room and feeling the pressure. People getting caught up in minor details rather than talking about root causes, or not asking the five whys to get to that root cause. You also touched on getting buy-in across the organisation. When people are really nailing it, when alignment is really there, what does that room feel like?

Andreas Wengenmayer: Yes, I've fortunately experienced those environments, and they're actually more common than you might think. When companies genuinely commit to grassroots planning, truly investing the time it requires, and ensure teams aren't overwhelmed from the start with everything marked "priority zero," you create the foundation for successful planning.

When companies genuinely commit to grassroots planning, truly investing the time it requires, and ensure teams aren't overwhelmed from the start with everything marked "priority zero," you create the foundation for successful planning.

You can see it immediately in people's body language and interactions. The energy in the room is palpable. If people appear resigned or intimidated, afraid to speak up, that's typically a red flag. The opposite creates magic.

Think about high-performing teams, like being a Scrum Master with an exceptional group. The best teams aren't just collections of highly skilled individuals in specific roles.

The best teams are those who communicate openly, genuinely enjoy each other's company, maintain positive energy, and actively support one another. This dynamic enables remarkable achievements. Maybe someone knows a contact in another tribe, release train, or department who can provide crucial answers and facilitate communication. Communication is absolutely fundamental.

That collaborative spirit is the hallmark of truly effective teams.

Hayley Rodd: Absolutely. We would know it in our day-to-day work, right? If your teams aren't communicating, if they're too overburdened as you said, it's not a good place to start. But if you can get that starting point right, if you can get that communication right, so many things will flow after that.

Andreas Wengenmayer: Absolutely. Looking back at any planning cycle, the real test is: did you plan the right things? You only know at the quarter's end whether you estimated capacity accurately.

Here's the crucial question: How does your organisation respond when goals aren't met? Do stakeholders focus on finding solutions? Do team members feel safe asking probing questions and seeking answers? Or does the blame game begin, searching for scapegoats?

How does your organisation respond when goals aren't met? Do stakeholders focus on finding solutions? Do team members feel safe asking probing questions and seeking answers? Or does the blame game begin, searching for scapegoats?

When you're permitted, encouraged, even, to be genuinely open and honest, you become much better at assessing realistic capacity. What makes stakeholders universally happy is predictability. You want confidence that your plans will actually materialise, that your commitments will be fulfilled.

Success breeds success, creating a positive foundation for the next PI. It's a continuous cycle that can spiral upward toward excellence or downward toward dysfunction.

The startup vs. enterprise spectrum

Hayley Rodd: Let's talk about the two ends of the spectrum. You've got a lot of experience, so I love hearing about this. Small companies will often say, "We're agile, we can pivot quickly, we don't need formal goal setting." Then enterprises are going all out on OKRs, cascading objectives, saying they're aligned because they've got those things in place. Yet both struggle with the same core problem. What's really going on?

Andreas Wengenmayer: You're absolutely right. I've been in agile projects since 2014, 11 years now, and I've seen a lot of companies pre-COVID, post-COVID, different sizes.

Starting with the really small ones, startup companies - what's really astonishing is that some very small startup companies tend to become overly complex, which is amazing. Some want solutions that are way too overblown. Basically, they need a sailing boat, but they're thinking about ordering an aircraft carrier.

Some startups want solutions that are way too overblown. Basically, they need a sailing boat, but they're thinking about ordering an aircraft carrier.

Maybe that's part of startup CEO culture - where everyone's a CEO on LinkedIn, and they think, "We're corporate, we have to be like that." They mostly get to their senses in the end, but small companies tend to be overly complex and overblown when it comes to technology, tooling, and organisation.

On the other end, large corporations sometimes seem to try their best to become truly agile - living the values everywhere. Still, it's a challenge. In most cases, there's some kind of hybrid planning going on. There's still a roadmap, which is good, but at some level, some people still stick to classical approaches, have some waterfall going on in the back.

I personally have never seen, for example, a full SAFe organisation where it's done truly at every level. There's a good balance and it should be healthy, but it all comes down to execution.

I feel like mid-sized companies are often the healthiest when it comes to that.

There's a balance of method and tooling, but you still need a solid understanding of goal setting and tracking. This includes pivoting when goals aren't right and learning from how you did things in the past. The gap between management and teams isn't that huge, and it's easier to bridge.

Avoiding death by KPI

Hayley Rodd: You've touched on so many fundamental things around getting the method and tooling right, but also that cultural aspect. I love the insight around mid-size organisations often striking that balance well. When we're thinking about the enterprise risk - which could be "death by KPI" or OKR, do you agree? Can you paint a picture of what that looks like and how it actually makes teams less focused?

Andreas Wengenmayer: Absolutely. There is such a thing as "death by KPI." KPIs are important to get a clear picture - you do need metrics, and there's merit to it. But as always, it's about choosing the right KPIs, the right metrics.

My favourite example is comparing story points across teams or ARTs. You measure velocity, and I have to repeat again and again: it's only individual to one team. You shouldn't compare it to another team or across tribes or ARTs - that doesn't work because you're creating the wrong incentives.

You see what will happen: "Well, okay, my stakeholders want higher amounts of story points. Let's estimate the stories bigger." Of course, that's a continuous loop, but it doesn't give you anything. Story points as a metric are just guidance for a team to get a better feeling for estimations.

You see what will happen: "Well, okay, my stakeholders want higher amounts of story points. Let's estimate the stories bigger." Of course, that's a continuous loop, but it doesn't give you anything. Story points as a metric are just guidance for a team to get a better feeling for estimations.

You want predictability - you want to meet a certain range. So it's not a great KPI when it comes to monitoring progress across teams. They have better KPIs in place.

Other metrics tend to create what I call bureaucracy. If you spend too much time creating reports, you have less time to create anything of value.

Hayley Rodd: I think there's so much in what you're saying about people being realistic and honest, open to pivoting or changing a goal if it's not the right one. Admitting to that is really difficult because no one wants to admit that what they set out to do is failing. But understanding that failure can sometimes be a benefit - you can learn from that. There's so much in that cultural aspect, right?

Andreas Wengenmayer: Absolutely. Coming back to goals rather than KPIs - KPIs are like being on a boat in your control room. You see what the engine is doing, the temperature - those are KPIs. Goals, on the other hand, are the course that you set.

KPIs are like being on a boat in your control room. You see what the engine is doing, the temperature - those are KPIs. Goals, on the other hand, are the course that you set.

You could be a small company like a startup - you're in a canoe, you're rowing. Or you're a large company - you're like a big freighter. Still, if you don't set the right course, the right goal, you will never reach your destination. Your team can be as proficient and perfectly working as they could be. If the course isn't right, hopefully you have enough provisions on board to survive a long journey.

Where organisations get stuck in goal setting

Hayley Rodd: Where do organisations typically get stuck? Is it defining the goals, communicating the goals, or translating them into action - that execution point you made before?

Andreas Wengenmayer: It could be basically any one of those. If you have a smaller or mid-size company, it's easier to communicate - you don't have to bridge as huge a gap. But still, you have high-level goals that have to be translated into real work. Real value is created in the teams.

If you have a high-level goal that's highly abstract and sounds good on paper - "increase customer satisfaction," "create better products," "make the world a better place" - people still have to understand: What does that mean to my daily work? If I'm a developer, what's my stake in that? How can I contribute?

If you have a high-level goal that's highly abstract and sounds good on paper - "increase customer satisfaction," "create better products," "make the world a better place" - people still have to understand: What does that mean to my daily work? If I'm a developer, what's my stake in that? How can I contribute?

That's when communication and breaking down goals becomes really important. Breaking them down the right way, having them visible and transparent, and creating that feeling of contribution. You make it visible that you're not just working for yourself or your team, but you're really contributing. You understand what you're working on and why you're doing it. Purpose is critical.

Bridging the strategy-to-sprint gap

Hayley Rodd: That's a really good segue into the next question about translating strategic vision into team-level objectives that people can grab onto and execute. Leadership will often say something like "increase customer satisfaction," and teams are left going, "What does that mean for me in my sprint this week?" How does an organisation bridge that gap between the high-level leadership view and what we can do in our sprints as a team?

Andreas Wengenmayer: First of all, you as company management need to take the time. There have been, and still are, a lot of approaches with company values, putting posters on walls, creating marketing. Those are all values - that's what a company is like. Then you link it with your products, services - great services, customer satisfaction. Okay. Then comes the real challenge: we want to succeed and create the next service, software solution, or product.

The goal is clear on a high level, but how do we break it down? That's when the real work comes into play - breaking down the goals into smaller pieces.

It's like building a LEGO space station when I was a kid. You have the picture on the box in the beginning - 'Oh, that's what we're going to build.' Then you have to start putting together all the small pieces. You need a plan, you need the little pictures of the steps. You start with the big picture, then you're breaking it down one piece at a time. You create different parts, and they come together at the end. Same goes for goals.

It's like building a LEGO space station. You have the picture on the box in the beginning - 'Oh, that's what we're going to build.' Then you have to start putting together all the small pieces. You need a plan, you need the little pictures of the steps. You start with the big picture, then you're breaking it down one piece at a time. You create different parts, and they come together at the end. Same goes for goals.

Hayley Rodd: Nice. A colleague of mine often says you eat an elephant one bite at a time - similar thing, right? When you see that big goal, it's really overwhelming. But if you can break it down into those chunks and smaller pieces, it becomes so much more manageable and achievable. People can get behind that vision.

Managing moving targets

Hayley Rodd: In fast-moving environments, goals often shift. We're agile, we're always moving. How do you help teams stay connected to a moving target without either ignoring changes or constantly thrashing around?

Andreas Wengenmayer: Back in the nineties and early 2000s, there was a computer game that wasted a lot of time in offices where you were shooting at geese in Scottish Highlands. It was a big phenomenon because people were trying to get the next high score.

If you think of moving targets, it's a bit like that. Imagine you're doing your work - whether you're a hunter or developer doesn't matter - but you approach, you take aim, and the geese keep flying up. You miss the target. Same thing if you have moving goals.

It's harder to aim and approach them right. What you should avoid as a company or someone in charge is constant interference. Stick to your goals or objectives that were agreed upon during PI planning. Don't change them midterm during a PI.

What you should avoid as a company or someone in charge is constant interference. Stick to your goals or objectives that were agreed upon during PI planning. Don't change them midterm during a PI.

That doesn't mean you can't learn from mistakes or wrong goals. You can adjust them, but you have to adjust them in the right place and time, which is during planning. Of course, if something security-related comes up, you have to act, but it has to be agreed upon, and you still have to communicate it and create understanding.

Keeping goals visible and actionable

Hayley Rodd: Even when goals are well-defined, keeping them visible and actionable throughout a PI is tough. What practices or tools have you found most effective for maintaining connection between daily work and high-level strategic objectives?

Andreas Wengenmayer: Good question. Having the goals present at all times helps a lot. If you just meet for planning, have your goals set, and never look back during the PI, it doesn't do you any good.

That could be a piece of paper on the wall like we had back in the day - and still could be if you're working in the office. Also, choose the right tools to track the goals and create acceptance for tools. Really use them. Look into them - whether it's an OKR tool or some other solution, even PI objectives. Are we still on track?

What really helps is if it's not static but shows progress, and especially shows the link of what you're contributing - like what you achieved in your last sprint and how it plays into the objectives or goals, progress moving ahead. There's always a good feeling - everybody loves a green bar moving ahead or a checklist.

What really helps is if your tool is not static but shows progress, and especially shows the link of what you're contributing - like what you achieved in your last sprint and how it plays into the objectives or goals, progress moving ahead. There's always a good feeling - everybody loves a green bar moving ahead or a checklist.

It helps keep the vision and goals present.

Hayley Rodd: When I was a teenager in my final year of high school here in Australia, I wanted a specific score on my final exams. I had a big poster in front of my desk that I sat at for hours every day studying. Looking back, I didn't know what I was doing - I just wanted to visualise my goal, and I didn't know the psychology behind it. But I'm happy to report I got that mark and above.

I think it was as you were saying - that constant reminder, that piece of paper worked for me. In organisations, we're looking for something a bit more complex sometimes, but I like your "keep it simple" advice. It doesn't always have to be super complex. It can just be a checklist, progress bar, or piece of paper - something that helps you feel connected to the goal and reminds you of it often.

When good work doesn't align with goals

Hayley Rodd: Have you seen situations where teams were delivering lots of work - good work, but it wasn't clearly contributing to company goals? What tends to cause that disconnect?

Andreas Wengenmayer: Yeah, that happens quite a bit. I can think of one example with very technical teams, like in semiconductors. Very smart people - everyone has a PhD in physics, material science. Awesome, smart people who tend to love their job. They're awesome, but they're also perfectionists who can still improve things and want to make them even better.

If you're in the business of producing machines used to produce semiconductors, for example, it's a complex task with a complex supply chain or value chain. You're creating lithography machines to create wafers used by other companies, and in the end, you have a customer planning the release of a new phone.

Your customer waits, the end customer waits, and you have to deliver on time. Sometimes this creates a challenge because teams still want to improve and make it even better. That's when economics come into play - the view of the big picture. You still have to communicate it. You shouldn't discourage such a great team, but you need to get the bigger perspective back to the teams and create acceptance instead of saying, "Hey, stop what you're doing, it's good enough." You don't want that. It all comes back to transparency and communication.

On the other spectrum, what you sometimes have is just too much workload on teams. Time for planning gets cut short, and if you don't take enough time to plan well, no wonder the results don't work out. It's just a lot of busy work - a lot of things getting done, but not necessarily the right things at the right time.

On the other spectrum, what you sometimes have is just too much workload on teams. Time for planning gets cut short, and if you don't take enough time to plan well, no wonder the results don't work out. It's just a lot of busy work - a lot of things getting done, but not necessarily the right things at the right time.

Hayley Rodd: If you don't do that planning at the start, you're setting yourself up for misalignments. If you're not communicating that plan regularly, you're setting yourself up for that busy work and people getting distracted. It's just so common. That planning part is so fundamental to getting it right.

One piece of advice for frustrated leaders

Hayley Rodd: We're on the home stretch now. If you could give one piece of advice to an engineering or product leader who's been frustrated because their teams seem to be going through the motions of PI planning or quarterly planning without real buy-in, what would it be?

Andreas Wengenmayer: I can resonate with that so well, and many can. I'd say: take the time to find out what's really going on. Investigate the root cause. It's like if you have a house and you're trying to fix a crack in the wall - you can look at the crack and do some superficial fixing or use a thick layer of paint, but you still have to find out what's causing that issue. Maybe something deeper.

You mentioned the five whys - that can be one way, but you have to have some understanding of the right way to approach people. You don't want to put anyone on the spot. Looking for a scapegoat doesn't help anybody.

We need to look at what's behind it, what's causing it. It all comes back to investing enough time for planning, but doing it with purpose. Not doing the whole planning like theatre, where everybody acts their part - that doesn't do you any good.

It all comes back to investing enough time for planning, but doing it with purpose. Not doing the whole planning like theatre, where everybody acts their part - that doesn't do you any good.

People have to understand why they're doing it. There has to be purpose and understanding - enough time, no distractions, and a positive atmosphere where everybody can contribute and be open.

You don't want people saying nothing because they don't dare to criticise or say no.

The connection between goal clarity and team motivation

Hayley Rodd: What's one thing you wish more organisations understood about the connection between goal clarity and team motivation?

Andreas Wengenmayer: We could get back to the boats we mentioned before. You want to arrive at your destination. If you're not clear about the destination, or maybe some people in your rowing boat don't want to go there, they might not join the rowing. If your crew is not invested, it will take you longer to reach a destination, or you won't get there as well.

It's the same thing. Motivation is key, and I don't talk about superficial motivation that just annoys everybody. Motivation is a positive environment where people rely on each other. They really like spending time with those people.

"Hey, I really like to go to lunch with you and talk to you" - not "I'd rather be home and not talk to anybody." You're not annoyed if your teammate asks you a question; you're happy to help. You're feeling safe that when you have a problem or question, you will get help.

That creates the right kind of motivation - that positive environment, and that can make a lot of things happen. It comes back to openness and transparency, not as buzzwords, but to get the clear picture. As a stakeholder, you get the correct current state because you get true answers.

I've seen strange situations in major corporations where people really didn't report what they were working on or show the right results. I've seen complete shadow Jira environments - one for internal use and one for external use with customers. There can be huge misalignments because people didn't dare to show real progress. In the long term, it will backfire. If you don't have trust in your environment, in your company, you will have a hard time.

I've seen strange situations in major corporations where people really didn't report what they were working on or show the right results. I've seen complete shadow Jira environments - one for internal use and one for external use with customers. There can be huge misalignments because people didn't dare to show real progress. In the long term, it will backfire. If you don't have trust in your environment, in your company, you will have a hard time.

Wrapping up

Hayley Rodd: There are so many key themes coming up throughout our conversation. You've talked about ongoing communication across teams, really planning with purpose, getting that context and buy-in to help with motivation, and allowing for radical candour - being really open if something's not working and being okay to call it out. So many cultural and communication elements are critical to the success of quarterly planning, PI planning, and organisations generally. Great takeaways.

We're going to end it there, but I want to end with a teaser for our interactive webinar that you and I are doing together on September 4th, which dives deeper and shows how to operationalise the ideas we've chatted about here using Easy Agile Programs and linking back to the fundamental services that catworkx provides organisations.

Andreas, it's been super wonderful to chat with you. I look forward to our webinar coming up on September 4th.

Andreas Wengenmayer: Thank you so much for having me. Looking forward to September 4th and seeing you again, talking more about tooling, boats, duck hunt, and anything in between.

Ready to transform your strategic planning?

The conversation doesn't end here. Andreas and Hayley hosted an interactive webinar where they showed how you can put these strategic alignment concepts into practice.

They spoke about:

• Practical techniques for breaking down strategic goals into actionable team objectives
• How to maintain goal visibility throughout your PI cycles
• Real-world examples of successful alignment transformations

Watch the webinar recording here →