Easy Agile Podcast Ep.15 The Role of Business in Supporting Sustainability Initiatives with TietoEVRY

"Having gone through a cloud migration at Splunk, Greg share's some insightful key learnings, challenges and opportunities" - Chloe Hall

Greg Warner has been involved with the Atlassian ecosystem since 2006 and is a frequent speaker at Atlassian events. Greg has worked as a senior consultant for a solution partner, supported Jira and Confluence at Amazon, and in his current role at Splunk, executed a cloud migration to Atlassian Enterprise Cloud for over 10,000 of his colleagues.

In this episode, Greg and Chloe discuss the cloud migration journey:

📌 The mental shift to cloud migration and how to think beyond the technical side

📌 How to navigate the journey without a roadmap to follow

📌 The four pillars to success for your cloud migration journey

📌 Finding the right time to migrate & thinking about future opportunities    beyond your migration

📌 The unexpected value that can come from a cloud migration

+ more!

📲 Subscribe/Listen on your favourite podcasting app.

Thanks, Greg and Chloe!

Transcript

Chloe Hall:

Hey everyone and welcome back to the Easy Agile Podcast. So I'm Chloe, Marketing Coordinator at Easy Agile, and I'll be your host for today's episode. So before we begin, we'd like to acknowledge the traditional custodians of the land from which I am recording today, the Wodiwodi people of the Dharawal-speaking nation and pay our respects to elders past, present, and emerging. We extend that same respect to all Aboriginal and to Australia Islander peoples who are tuning in today.

Chloe Hall:

So we have a very exciting guest on the podcast today. This guest has been involved with the Atlassian ecosystem since 2006 and is a frequent speaker at Atlassian events. He has worked as a senior consultant for a solution partner, supported Jira and Confluence at Amazon and at his current role at Splunk, executed a cloud migration to Atlassian Enterprise Cloud for over 10,000 colleagues. So welcome to the Easy Agile podcast, Greg Warner.

Chloe Hall:

How are you?

Greg Warner:

Good, and thank you for having me.

Chloe Hall:

No worries. It's great to have you here today.

Greg Warner:

This is one of my favorite topics. We talk about cloud migration and yeah, I hope I can explain why.

Chloe Hall:

Yes, that's exactly what we want for you because I remember when we met at Team 22, you were just so passionate about cloud migration and had so many insights to share and I was very intrigued as well.

Greg Warner:

To give it a bit background about myself.

Chloe Hall:

Yeah.

Greg Warner:

I haven't always been a cloud person. So you mentioned before about being involved since 2006. I was involved early days with when Jira had the several different flavors of standard and professional, when you'd order an enterprise license for Atlassian and they'd send you a shirt. That was one of the difference between one of the licenses. So based a lot in the server versions, over many years. I looked at the cloud as being the poorer cousin, if you like.

Greg Warner:

I'd been to several Atlassian summits and later Team events where there was always things of what was happening in cloud but not necessarily server. I participated in writing exam questions for Atlassian certification program for both server and DC. For me, in the last 18 months, two years now, to make this fundamental shift from being certainly a proponent of what we do doing on server in DC to now absolutely cloud first and that is the definite direction that we as a company have chosen and certainly why I'm so passionate about speaking to other enterprise customers about their cloud migration journey.

Chloe Hall:

Wow. So what do you think it was that you were like, okay, let's migrate to the cloud, as you were so involved in the server DC part of it? What was it that grabbed your attention?

Greg Warner:

I joined Splunk in 2019 and it wasn't all roses in regards to how we maintained Jira and Confluence. It wasn't uncommon to have outages that would last hours. For two systems that were just so critical to our business operations to have that, I was kind of dumbfounded but I thought, hey, I've been here before. I have seen this. And so it was a slow methodical approach to root cause our problems, get us to a version that was in long-term support, and then take a breather.

Greg Warner:

Once we got to that point where we didn't have outages, we kind of think of what the future would be. And for me, that future was exactly what I'd done before, what I'd done at Amazon, which is where we would move all of our on-prem infrastructure, Jira, Confluence, and Crowd to public cloud, whether it would be a AWS or GCP, something of that flavor. I'd done that before. I knew how we were going to do that to the extent that I'd even held meetings in my team about how we were going to stand up the infrastructure, what the design was going to be.

Greg Warner:

But there was probably one pivotal conversation that was with our CIO and it was in one of those, just passing by, and he's like, "Greg, I've seen the plans and the funding requests." He's like, "But have you considered Atlassian Cloud?" Now, the immediate personal reaction to me was like, we are not going to do that because I'd seen the iterations. I'd seen it over time. I'd worked for a solution partner. I'd worked with customers in cloud, never really thought we could be enterprise-ready. So my immediate reaction was not going to do that. I said, "I'm not going to answer that question right now." I said, "I don't know enough to give you an answer."

Greg Warner:

And I'm absolutely glad I did that because I would've put a foot in mu mouth had I given the immediate response that was... So yeah, I took that question, went and did some analysis, spoke to our technical account manager at the time, and really looked at what had been going on and where was cloud today? Where was it in its maturity? And the actual monumental thing for me was that I think it's actually ready. People make excuses for why they can't do it, but there are a bunch of reasons why you should. And if we look at us as a company, with our own products that we are moving our own customers to cloud, and we are using cloud services, like Google Workspace and Zoom and a variety of SaaS applications. What was so different about what we did in engineering that couldn't go to cloud? And that was like, okay, I think the CIO was actually asking me a much bigger question here.

Greg Warner:

So the result of that was yes, we decided that it was the right time for Splunk to move. And that is a monumental shift. And I know there's a lot of Jira admins out there that are like, if you do this, you're putting your own jobs at risk. The answer is no, you're not. And even within my team, when we had we'd discussed this, there was emotional connection to maintaining on-premise infrastructure and were we giving our own jobs away if we do this? There's all those... No.

Greg Warner:

And there have actually been two people in my team that got actually promoted through the work of our cloud migration that otherwise wouldn't have because they could demonstrate the skills. But that's kind of like the backstory about how we decided to go to cloud. And I think as we are thinking about it, there is a mental shift first. Before you even go down the technical path about how you would do it, change your own mind so that it's open so that you're ready for it as well.

Chloe Hall:

Yeah, I love that. It's so good. And I think just the fact that you didn't respond to your CIO, did you say that?

Greg Warner:

Yep.

Chloe Hall:

That you didn't respond to your CIO straight away and you weren't like, "No, I don't want to do that." You actually stepped away, took that time to do your research, and think maybe cloud is the better option for Splunk, which is just so great and really created that mental shift in yourself. So when you say that your employees, like everyone kind of has that beef that, oh, we're going to lose our job if we move from on-prem to cloud and those employees ended up getting promoted. How did their roles change?

Greg Warner:

When we moved from on-prem to cloud, you no longer have to maintain the plumbing, right?

Chloe Hall:

Yeah.

Greg Warner:

You no longer have to maintain all the plumbing that's supporting Jira, Confluence, BitBucket, whatever is going to move. Now we thought that was the piece that's actually providing value to the organization. And it wasn't until we went to cloud, we actually realized it wasn't. Like what we can do now is different. And that's what my team has done. They've up-leveled.

Greg Warner:

So in the times since we moved from Jira, Confluence on-prem to cloud, we now get involved a lot more with the business analysis and understanding what our project teams want. So when someone from engineering is requesting something that has an integration or a workflow, we've got more time to spend on that than are we going to upgrade? Are we on the current feature release? Is there a bug we have to close? Log for J as a prime example where the extent of where we covered was logging a call with the Atlassian enterprise support and then telling us, "Yep, it's done."

Greg Warner:

Whereas other colleagues within the ecosystem that I spoke to spent a week dealing with that, right? Dealing with patching and upgrades. So the value for our team in the work we do has shifted up. We've also done Jira advanced roadmaps in that time. So we've been able to provide things we would've never got to because we're too busy to the plumbing, to the extent now that we have a very small footprint of on-prem that remains and that's primarily FedRAMP and IO5. It's not quite certified yet. It's going to get there. So we have a very small footprint and I'm the one who has to do the upgrades and now you look at it like, oh my god, that's going to be this couple-week tasks we going to do where I could do all this other better work that's waiting for us in cloud. You don't realize it until you have it removed how much you used to do.

Greg Warner:

And so we used to do two upgrades of Jira year and two upgrades of Confluence a year. We put that down to about a month's work of each. By the time you do all of your testing and you're staging and then do that. So you're really looking at four months of the year you were spending doing upgrades. We don't have that anymore. It's completely gone. And so now we make sure that we do things cloud first. We don't bring across behaviors that we were doing on-prem into cloud. So that's probably one thing we learned was that don't implement server DC in cloud.

Chloe Hall:

Yeah, that's so great. It seems like it's opened up a lot more opportunity for you as well. So I think something that I kind of want to look into and understand a bit more is that people focus a lot on the technical aspect of the cloud migration. What other aspects do you think need to be considered?

Greg Warner:

Certainly people. I mentioned at the very front here the mental mindset and that really started with my team, to get their mind around how we're going to do this cloud migration. There isn't necessarily yet a roadmap that says these are all the steps need to take to get ready for your cloud migration. So we had to invent some of those and one of those two was, what did we want to get out of the cloud migration?

Greg Warner:

I speak to other Atlassian customers. You talk about they're running a project, the project is the cloud migration, the start and the end is the cloud migration day. No, completely wrong. The cloud migration actually has a beginning, a middle, and an end. What you're talking about here, about this first changes is in the beginning, and that should be we're moving to cloud because it should be fundamentally better than what we have today.

Greg Warner:

If it's not better, there's no value in doing the activity. So we started with a vision and that vision was that all of the core things had to work from day one and they had to work better. So create issue, edit issue, up to issue, that just needs to work. There should be no argument whether it does or does not. That needs to work and work better. Create a page, edit a page, share a page. That stuff needs to work in Confluence without any problems. We also need to make sure that there are people in the organization who this could be a fundamental change of how they work, depending on how much they work with Jira and Confluence. So appreciating that there is some change management and some communications that needs to be ready as you do your cloud migration to ensure that your vision is going to work, but also acknowledging you will break some things. You're not going to be able to do a cloud migration and shift you from A to B without nothing.

Greg Warner:

It will go wrong. So we were aware of that and for that, what I would always tell people was that we're really fixed on the vision of making it sure it's better than it was today, but flexible on the details, how we get there. We will probably find different ways as we go along because things will change. Cloud changes itself. You'll discover things you didn't know before. There was a Jira admin that made a decision 10 years ago, you now found that. So yeah, very, very fixed on that vision that day one that we had to have this unboxing experience that when people got to use Jira and Conference Cloud for the first time, they could see why we'd spent so much effort to make sure it was polished and things just worked. And as you went a bit further out, there might be things to do with apps that might not be quite the same.

Greg Warner:

That's okay. And then further out, things you just ultimately can't control. And for that, we had 76 integrations of teams that had written automations from all over the company. We're never going to get to find out what they do, but we knew that some of those would probably break. And so just dealing with some change control and allowing those people to know this is coming, what the rest endpoints will be, how to set up their API keys. We did a lot of that, but we did have one integration that broke and that integration broke because the entire team was on PTO or leave that week. We can't avoid that one. But it was good to see other teams actually jumped in because they'd been involved in updating theirs to go help fix that. So that was okay. We had one integration that we really gave the white glove support to and that was for... We have a Salesforce to Jira integration that's a revenue-generating integration.

Greg Warner:

We gave that a lot of attention to make sure that just worked. But the 76 others, we provided a runbook. The runbook was essentially teams, you do things like this. So they knew how to change and update to the new system. But yeah, certainly the beginning, middle and end. The beginning is all those shifts that you're going to have to change and probably some history about design decisions. The middle is in fact your cloud migration and the end, middle to the end is everything you do with it afterwards. So that's where the real value comes from in your cloud migration. It's once you're in, what can we do with it?

Greg Warner:

And we are towards the end of that now. There have been things that I couldn't have planned for that people have done. So we did your advanced roadmaps, saving the forest there, but also we're encouraging our staff to extend the platform. That used to be really difficult and we've worked with Atlassian to understand what should that look like? And we've settled on using it Atlassian Forge. And so now we have our first app this week, in UAT, in Atlassian Cloud to solve business problems that we have. That's a custom Atlassian Forge app. And we're encouraging our engineers to build those and so they can extend and get that real value through the cloud migration.

Chloe Hall:

Yeah, wow. You've come so far and it's nice to hear that you're towards the end of it and all the opportunities are coming with it and you're seeing all the value. It's all paying off as well. I think I just want to go back to that moment where you talk about there isn't essentially a roadmap outlay. There isn't someone or something to follow where it says this is where you need to start. These are the steps to cloud migration. And I think a lot of people, that's what they fear. They're like, we're not sure exactly where to start. We're not sure what roadmap we'll follow. How do you navigate that in a way?

Greg Warner:

So I get back to that when I talked about the vision. We said we're fixing the vision flexible details. Early on when we signed for cloud migration, it was in the first week after we'd signed for it, that same CIO asked me, "Greg, what's our date? When are we moving? Because you've sold me that this is so much better. Where's the action? When are we get this?" And we took a good six weeks after we signed to actually understand the tooling that's available. So for Jira, there's really two options. There's the Jira site import and the Jira cloud migration assistant. And on Confluence side, there's one that's called the Confluence cloud migration assistant. Better kind of understand how those technologies work. And for a couple weeks there, my team actually considered if we did the migration ourself, we could probably save the company a bunch of money and we would own it.

Greg Warner:

We would know how this thing worked. We got about four weeks in and decided that was a terrible idea. Do not do that. Any enterprise customers I talk about that say we're going to do it ourselves, do not do that. Do not do that. And part of the reason is that there's really four pillars to success for your cloud migration. Jira migration, Confluence migration, apps, and users. And we did not know how to do apps and users and we probably could have gotten away with Confluence and Jira. But we said, look, this is something that we actually need to have a partner involved. And so we did ask for partners to provide their way of doing it, knowing what they knew about us. And we did provide as much detail as we can. We had two partners actually provided completely different methodologies how to get there.

Greg Warner:

So this is that flexible on the details, but we really had to make a decision on what worked for us. So when it really came down to Jira, would we do a big bang approach and just switch it over in the course of a weekend or did we want to do cohort by cohort over time? And we decided for us, because we are a 24/7 organization that's supporting our customers, doing the big bang switchover, that was the best way to do it. So that's one of the reasons we chose the partner we did. But that partner didn't necessarily have a roadmap of where they want to go. But we did then explain what we want to get out of this. That was the first thing, was about it needs to happen on a weekend. So that then filters down what your choices are. The ecosystem apps part is really important to make sure that one, there may have been apps installed in your system that have been there for 10 years and you're not sure why they're there anymore because it was four Jira admins ago.

Greg Warner:

Nobody knows what's there. But if they don't have a cloud migration pathway, you really should consider they're probably going to hit their end because there is no equivalent. So you can rule them out. Identify the ones that do have a business process with them. And for that, Salesforce for us, we had to find a cloud-first connect that would work. So that meant that we knew that was going forward. But really, I think the key thing that we invented that we didn't know about was that we created this thing called an App Burn Down. And that's where we looked at all the apps we had. We had about 40 apps. We said, okay, which ones are not going to go to cloud? Which ones don't have a migration pathway? Which ones are going to replace something else? And so we started to remove apps over the course of about three months.

Greg Warner:

So people would see that we're starting to get away from on-prem design decisions and old ways of doing things. But we also said, but once we get to cloud, this is the pathway out of it. So that we said, look, we're going to turn this app off but you're going to get this one instead, which is the cloud-first app. So people could see how we're going to make the jump over the river to get there. But it meant that we would, over time, identify apps that weren't used. If we turned them off and nothing happened, it's fine. But also we did come across some where they were critical to a business use. And so if we didn't have an answer for those yet, it gave us time to find one. And with your user base, typically it's your colleagues, that's going to be your most critical customers. They're going to ask, okay, you're turning it off. When do I get the functionality back?

Greg Warner:

And by doing that App Burn Down over time, that does buy you time to then have that answer. So it's a much easier conversation than I'm simply turning off functionality, I don't have an answer for you yet. There are things like that. It wasn't necessarily a roadmap, but working with a solution partner is absolutely the right way to go. Don't try and do it yourself. They also work with Atlassian and they have far better reach into getting some of these answers than you can possibly ever have. And I have on at least three different occasions where our solution partner did go and speak directly with an ecosystem partner to find out what's the path forward. How can we make this work? So it is good. The migration is really a three-way collaboration between yourself, your solution partner, and Atlassian. And you all have the same goals. You want to get to cloud and it does work really well.

Chloe Hall:

Wow. Yeah. So sounds like hope everyone got that advice. Definitely don't take this on your own. Reach out to solution partner. And I really like how you said you went to two different solution partners and you found out what their ideas were, which ways they wanted to take you, so you could kind of explore your options, work out what was the best route for Splunk. And it's worked very well for you as well. Having that support I think as well. Yeah. Sorry, you go.

Greg Warner:

The choice of the partner is really important and it's probably one of the earliest decisions that we made to get that one right. And I remember several times thinking about, have we got the right people on board? Did we speak to... And it was an interview process to the extent that when we had our final day after we'd been working with Atlassian and with our partner for six months, one month after our migration was completed and we're all done, we had one final Zoom call with all of us and took a photo and did that. But it kind of felt like a breakup, to be honest, because we'd been in each other's faces for six months and working. We're now all saying goodbye. We might not see each other. It was like the weirdest feeling. But it did work. And so yeah, it is a real fundamental choice.

Greg Warner:

Just take the time, make sure they understand what we want to do, make sure you understand how they're going to do it. But yeah, if we have done it ourselves, we would've got ourselves all caught up in knots, wouldn't have been a successful migration or so. I'm a technical guy. I want to solve it. I want to be like... But I think the actual right answer was no, you don't need to know how this works 100% because you're going to do this hopefully just once. And so focus on the real business value things about dealing with stakeholders and the change and making design decisions that are really important for you because you're going to own those probably the next decade rather than worrying about how do I get my data from A to Z?

Chloe Hall:

Yeah. It definitely would've felt like a breakup for you because you would've been working side by side for so long, dealing with so much. Are you still in contact with them or...

Greg Warner:

Yeah, we had this fundamental thing we always said is we're always, if there's a problem, we're always cautiously optimistic, we're going to solve it. We did engineering challenges that we went through, but I did say right early on is, the ecosystem is only big and we're all going to bump into each other at some point. So yeah, let's make sure that we're still friends at the end of this. And I didn't realize how important that was until later when I was in New York for Christmas and I arranged to meet the project manager that worked for us. She lives in New York, so how about I meet you so... So we met each other at the hotel and she's like, "I have never met a customer outside of work to do this." Yeah, I gave the story about it felt like a breakup, but she did say that at the beginning you said we'll be friends after.

Greg Warner:

Yeah it is because it can be really hard. I've been on the consultant side where you kind of have to have some hard conversations and sometimes... You want to make sure that everyone understands the problem. You're trying to make it better so that at the end of it, you can still be friends like that. That is the thing. There probably will be engagements later on that you might need them again. So you want to make sure that you have your choice of best in breed partner to choose from. You have those relationships. They understand what you want to choose. So yeah, it is really important to choose the right partner. Don't necessarily based on price but choose the partner that's going to work for you, understands what you're trying to get out of your cloud migration and they'll be there in the future when you need them for another cloud migration or a much more gnarly project. Try and be friends at the end of it.

Chloe Hall:

And definitely it's good that you have that friendship now because they have that understanding about your business and what you want and the value of it. So if you do need help again, it's a lot easier to bring them on board straight away. So now that you've performed a cloud migration and you're coming towards the end of it, do you look at the process any differently to when you were at the very beginning?

Greg Warner:

Yeah, I thought we were just executing a data migration just yeah, on-prem to cloud.

Chloe Hall:

Yeah.

Greg Warner:

Pretty straightforward, nothing big. I was pleasantly surprised as we're making some of these decisions as we went along, that it was more than that. There were business processes that we could improve. There was the beginning, the middle, and end. I didn't realize that until actually after the end. So when we did our cloud migration, it was actually the week before Thanksgiving in the US. It was November 19. And even that decision was made in just going for a walk at lunchtime. When should we really do this? And I kind of came down again, spoke to my project manager and said, "How about we do this in the cloud migration the week before Thanksgiving?" Because 50% of our workforce is located in the US and a large proportion of that will be on leave or PTO before.

Greg Warner:

So by doing it over a weekend before then we're ensuring that... Like when you open a new restaurant. You don't want to have all of your tables full on the first night. We knew that we were going to have everybody using Jira and Confluence day one after a migration because we're going to break some stuff. They actually turned out to be really exceptionally good idea. And I encouraged people to find... Look at your data and work out when is low time to do this? I've been involved in Jira and Confluence for a long time and just thought it's task tracker and it's a wiki. There's nothing there that I don't really know about. But one of the decisions we made was actually that when we completed the data migration and it was ready to go, I always said if we waited, do we get a better result? And the answer was no.

Greg Warner:

We should make this available to people now. And so we opened it up on a Sunday morning in the US, which was starting to be business hours in Australia. We started making teams aware that they can now go ahead and use Jira and Confluence. And it was the feedback that we immediately got from those teams that were starting to use Jira service management in cloud for the first time, about, "Wow, this is so much better than it was on-prem." And people said, "I can actually see the attention to detail you've made on fields and descriptions and the changes you've made." And it started to impact people's workday that this was better than it was. I didn't expect that to come back. And so I have a montage that we share with the team of all these Slack messages from people saying, "This is really good. This is much better than we had before."

Greg Warner:

What I didn't also realize is that when we moved from on-prem to cloud is the data that we had became more usable and accessible. Hadn't planned that. It seems obvious now, but when we put it in cloud and it has all the security controls around it and now no longer has the requirements of things like VPN to get access to it, people could build new things to use it to be able to interact with your issues, to interact with pages. And so we started with 76 integrations and over space of three months now we had this big jump in the first three months up to about a hundred something and now we're going to Forge And what it means is people who have had this need to be able to get to the data can now get to it. I didn't see that coming. I just thought we were just server cloud. But yeah, having a more accessible has led to improvements in the way that our teams are working but also how they use it in other applications that just simply wasn't available before.

Chloe Hall:

Yeah. Wow. That's great. And it's good that you were able to receive that feedback straight away from the teams that you had in Australia. I think that's really good and it sounds like it's created such a good opportunity for you at Splunk as well now that you're on cloud.

Greg Warner:

Yeah, it's certainly a business leader that can propel you forward and I eagerly come in now and look at what are other teams going to do with it. And so when we had the first team that said they want to build a Forge app, I'm like, Sure. We should not discourage that at all. Extend the platform. That's why we spent the money and time to do it. What can you do with it now? And we did certainly make Atlassian aware on the product side, like how we're using it and where we'd like to see improvements. If you look at the server DC comparison, I used to be that person that would look at the new features in cloud and ask that question about, when is that new feature coming to on-prem? To going to being that customer who's now, I have that feature today, right? And I'm using it because we don't wait for it.

Greg Warner:

So you mentioned about things you didn't plan from the roadmap. There are design decisions that I talk to enterprise customers that I need to make aware of about. One of them is to do with release tracks. In enterprise cloud, you can choose to bunch up the change to cloud and then they get released periodically every two weeks, every month. When I looked at that, came back to one of our principles about don't implement server in cloud, why would we do that? Atlassian has far more data points on whether this works for customers at scale than we do. So why would we hold back functionality? So as a result we don't do release tracks. We let all of the new functionality get delivered to us as Atlassian sees fit. And the result of that is our own engineering staff, our own support staff who use Jira, get the notifications about new products and features and this is fantastic.

Greg Warner:

Again, why would we implement server, which is where you would bunch up all your changes and then go forward? The other thing too about our cloud migration journey is don't be blinked that you're just doing a cloud migration today and then the project ends. There are things you need to be thinking about as you go along, but what's the impact in the future? So for us, we have multiple sites. Enterprise customer have multiple sites. So there are design decisions that we've made so that we can, in the future, do cloud to cloud migration. You will move sites. Your organization could be bought or could be buying companies. So you do mergers and acquisitions. And so as part of that, we have some runbooks now that talk about using the cloud-to-cloud tooling so we can move a Jira project from a site here to a site there, how we'd move users here and users there.

Greg Warner:

And that actually came about through the assistance with our TAM, not focusing just always on the cloud migration date but also what's that look like six months later? What's it look 12 months later? So that you don't perform your cloud migration and then lock yourself in a corner that later on now I have to unwind something. I had the opportunity to fix it. So yeah, I do encourage migration customers to also think six months, 12 months beyond their cloud migration. But what could also happen and then speak to your solution partner about design decisions today that could affect you in the future.

Chloe Hall:

Yeah. So you definitely need to be thinking future-focus when you're doing this cloud migration. I know you've addressed a lot of the opportunities that came out of the cloud migration. Was there anything else that was an unexpected value that came from it that you wanted to share?

Greg Warner:

The other value is make it more accessible. We have seen people use it in different places that we hadn't thought about. So some of the things that we were doing before, we had to have a company-owned asset to get on the VPN and just things like that. That actually restricted people in where they could do work. Whereas now we've, as long as you've got a computer or mobile device connected to the Internet, absolutely you can use a mobile device support, you can get access to it. Approvals that used to be done on a computer are now done on a mobile device. Those things. But I think the integrations has been probably been the one thing I'm most... We're not the catalyst. We kind of pushed it along but seeing people get real use out of it and using the data for other purposes. We have seen people build some microservices that use the data from Jira that we couldn't do before. Again, you're just unlocking that potential by making it more usable and accessible.

Chloe Hall:

After going through the whole migration journey and, like you said, you're coming towards the end of it, what were the things that stood out to you that you're like, okay, they didn't go so well? Maybe if I was to do this again, how would I do this better next time?

Greg Warner:

So I get back to that day one unboxing experience. You know you want to give it that best experience. And we delivered that for people in Australia and APAC as we opened it and they got to use Jira for the first time and it worked fine. And that is mainly the result of a lot of emphasis on the Jira piece because we said, we know this is going to be hard. It's got workflows, issue schemes, notifications schemes. This is going to be hard.

Greg Warner:

So we started that one really early and then probably about 60% down through our migration journey, we started on Confluence. We thought how hard can Confluence be. It's a bunch of spaces and pages. It can't be that hard. We actually hit some migration challenges with the engineering tooling with Confluence, which meant that the Confluence UAT was delayed. The Jira UAT was fantastic. Ran for a month. We found some problems, got fixed, got answers. We were really confident that was going to be fine.

Greg Warner:

And then we hit this Confluence piece. We're like, wow, this is going to be a challenge. And there was at least one time I could think of. It was a Saturday morning at breakfast where our solution partner sent me a Slack message about, I think we've got a problem here with some tooling. What are we going to do? Towards the middle of the day, I was kind of scratching my head. This could be a real blocker. We actually worked with Atlassian, came up with the engineering solution, cleared that out. That was good to see, like in the space of 12 to 24 hours, there was a solution. But what it meant was that it delayed the Confluence UAT and it made a week. And there was something we found to do with the new Confluence editor and third-party apps right at the end of that week. And we had to really negotiate with our stakeholders to make this go ahead.

Greg Warner:

Because again, if we'd waited, we'd get a better result. No, we really should go. We know that there's this problem. It's not system-wide but it affects a small group people. So we did it. But for about a hundred people they have this really bad Confluence experience because of this thing. And so for me, I couldn't deliver on that thing I promised, which was a day one experience that was going to be better than what it had before.

Greg Warner:

Now we did work with Atlassian and app vendors to get some mitigation so it wasn't as bad on day five. It wasn't day one but it wasn't perfect. But I would certainly encourage people to make sure that you do treat Jira and Confluence with as much importance as each other. They do go together. When I did our cloud migration, we did it on a weekend and I remember coming back after dropping my kids at school on Tuesday and sitting in the car park. I was like, wow, we actually pulled that off.

Greg Warner:

If we'd propose to the company to move your company email system and your finance system on a weekend, the answer would be no because it's too big a hat. But what we'd said is we're going to move all of our Atlassian stack in a weekend, which really is two big systems, Jira and Confluence. So if I had the time again, we would've started Confluence much, much earlier and then we wouldn't have the need to rush it at the end. And that really did result in a bad day one experience for those people. We have worked with Atlassian since then. We're getting that resolved. We know other Atlassian guys have the same problem. I would start early and don't underestimate the complexity that could happen. There will be some things outside of your control.

Greg Warner:

I talk about this Confluence problem and the migration tooling, which is actually do at scale. Not every customer will see it. We saw it, I conducted customer interviews when we were doing our solution partner decision and the customer actually told me this. Like I should have started Confluence because we had this problem, we wasted some time, and we did it. I even have my notes. But it wasn't until later, same problem, you even had the answer and they told you and you still waited. So I'm spending a few minutes on this podcast talking about it because it happened to me. It's probably going to happen to the next person. So if I could do one thing and that is just encourage you to start it earlier. You're going to end up with a much, much better migration and hopefully can deliver on that day one experience that I couldn't do.

Chloe Hall:

Yeah, no I'm so glad that you've shared that with the Easy Agile audience as well because now they know and hopefully the same mistake won't keep getting repeated. Well, Greg, my final question for you today, and I don't know if you want that to be your answer, but I think it's really good just for the audience, if there's one key takeaway that they can go away with them today from the podcast, what would be that one piece of advice for everyone listening to start their migration journey?

Greg Warner:

The first thing to do is to prioritize it. So if you're an Atlassian customer that's using on-prem Jira or Confluence and you don't have a timeline and you don't have a priority to your cloud migration, start there. Open up the task, which is start to investigate Atlassian Cloud and choose a date. Because yeah, there will come a situation down the track where you might be asked by your CIO and so it's better to have an answer prepared already. I would encourage people to start to look at it because it is the future. If you look across the industry, people are moving to SaaS. It's really a question. Do you want to maintain and be that customer wondering when that feature's coming to cloud or do you want to be that customer in cloud who has it today? We have seen a monumental shift to when we moved to cloud in functionality, availability, all the good things that cloud delivers. And it's one of the biggest promoter... The person that used to write exam questions for servers now saying go to cloud.

Greg Warner:

Absolutely. So when I've spoken to other enterprise customers, particularly at Team, I said like, when do you plan your cloud migration? I was like, wow, we're going to start it in three years. I'm like, three years? You need to go back to the office next week and start like 12 months because yeah you will... There is absolutely a competitive advantage to doing it. And it's not just me being now as biggest cloud opponents. We see it, we see it every day and for me, this is one of the most influential projects I've been involved in with Atlassian since 2006. This one here is going to have a long-lasting effect at Splunk for a long time and I'm happy to speak to yourself at Easy Agile and others about it and here at their cloud journey because I want to go to Team next year. I want to make sure we have these conversations in the whole way about, I got that one thing. It's either I started my Confluence migration earlier or I actually put in a timeline of when we should start our cloud migrations.

Chloe Hall:

Yeah, beautiful. That is some great advice to take away, Greg. And so honestly, thank you so much for coming on the podcast today. You have provided some brilliant insights, takeaways, and also because there is no roadmap, I feel like your guidance is so good for those who are looking to start their cloud migration. Yeah. We really appreciate you sharing your knowledge.

Greg Warner:

All right. Thanks for having me on. Thank you for listening.

Chloe Hall:

No worries.

TL;DR

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

Introduction

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

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

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

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

About Our Guest

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

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

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

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

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

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

Transcript

Transcript

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

"Okay, alright. And then what?"

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

"And then what?"

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Navigating Conflicting Forces - Outcomes vs. Predictability

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

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

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

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

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

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

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

"Because we have to increase mobile revenue."

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

The Power of Renaming Teams

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

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

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

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

Prove the Model

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

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

Team Autonomy and Empowerment

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

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

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

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

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

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

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

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

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

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

The Two-Way Solution

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

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

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

Demand Proactive Transparency

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

"Why is it difficult?"

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

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

"Well, because we have a sales team."

"Why does that make it difficult?"

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

"Okay, now I understand."

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

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

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

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

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

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

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

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

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 →