Senior leadership questions

Welcome to Definitely Maybe Agile, the podcast where Peter Maddison and Dave Sharrock discuss the complexities of adopting new ways of working at scale. Hello and welcome to another exciting episode of Definitely Maybe Agile with your hosts, Peter Maddison and David Shark. How are you today, Dave? Oh, it's excellent.

I'm actually in Toronto. You're in Toronto. So we actually found a room, got a bit of quiet time, and uh got a chance to have a chat in person for a change.

Which is fantastic. It's nice to actually uh be in person and uh actually have these conversations face to face for a change.

Well, not that we're not face to face on a video call, but uh it's well face-to-face in person is definitely different, isn't it?

It is, it is indeed. And so what's on the uh cards for today?

Well, a lot of uh podcasts that I've been listening to, they seem to kind of pull in questions from lots of different places. And uh, I've just been doing a a number of uh leadership workshops recently where the caliber of questions for were just those deep and meaningful, like you answer them with one or two sentences in a training environment because you're gonna move on to something else. And I think they're well worth a deeper dive. So got a couple of those up here. Let's just pull one or two in and see how we go. Sounds exciting. So, where do you want to start? Well, leadership workshop, talking about agile transformations, talking about cultural change, talking about digital transformations, all the stuff that we talk about all the time. And there's this one simple conversation question that came up, which is how can we bring senior leadership along on the journey? I mean, it's a simple, straightforward question, but has so much nuance to it.

There's definitely a lot of connotations in that one. There's a lot of hidden depths, isn't it? Yeah. Yeah. It's uh so well, but first off, what was your two-sentence answer?

Oh so actually, anytime I talk about leadership, I think my two-sentence answer is you got to lead with you know quick wins, find some results, stop talking about the change being what you're trying to achieve. The change is there to achieve a purpose. If you're not showing leaders how the time they've invested, the money they've invested, the sort of this the things they've said no to aren't providing some benefits which are strategic, which are top of mind, they're not gonna back it for long.

And we touched on this last time around as well when we were talking about cutter and change and how you scale it and penguins.

I can't look at penguins anymore without remembering that conversation.

Yeah. Uh yeah, it's it's very true. It's the uh one of those pieces is we we know we say that leadership will make it or break it, um, or at least leadership alone can't can't make it alone. But if you don't have that leadership buy-in, then it's almost certain to start to hit uh rocky waters, if you like it.

It's interesting. So there's been a number of studies. The one that I always kind of call back to is I think State of Agile from a couple of years back, maybe 2019 or 2020, identified leadership, executive leadership support as the factor that makes or breaks your transformation. And it's not the only study that's done that. There's lots of them that come around. That's for sure. Yeah.

Yeah. It always amazes me though that it's almost seems like an afterthought in a lot of the transformations that it's like, we'll roll out Scrum training and now everybody has scrum training. We're gonna, we're gonna try and guess how much work we're getting done using story points.

Well, it what I find as we're chatting away, and I'm looking at this post-it note here, there's an implicit assumption kind of behind the scenes that they're not along on the journey. And I think that one on its own is a is really one of the places to kind of start, which is, you know, there's that maybe your organization has a strategic objective, there's a digital transformation coming through, which agile is part of, or DevOps or whatever it might be. Great. We're all kind of, you know, our eyes light up, we're excited about this, we want to get involved. But what are the leaders showing through their actions, their words? What do they really mean or believe in, or what have they bought into, what have they not bought into? I think is a super important question to recognize.

Yeah, and I think that's uh that's really one of those key aspects of it. It's that the leadership, presumably, is bought into this in that they have spent some money and they've invested in it and they've said, hey, we want this, but what they've probably or may not have realized is that there's a change that they need to make as a part of that. Uh that's what a common piece that I see.

I'd even push back on something as straightforward as the leadership have bought into it. I mean, a lot of different pressures can be on that, that leadership team. And I think one of the it's it's been quite interesting. I've worked with quite a few people, like a couple of one or two layers below leadership. They're absolutely bought in and they're wanting to push the boat out and really take some risks and make some changes happen. And one of the first things that we end up doing is and it's almost like prove it, put your money where your mouth is. Let's and actually put your money where your mouth is is totally the wrong piece because they often do put money behind it, but that's not sufficient. It's what are the actions? What is what is where's the skin in the game being shown as to how what the leaders are thinking about? And I think that's an important piece, is is as a leader, let's say if the leader was listening to this right now, as a leader, you need to walk the walk and show very clearly that you're prepared to make the decisions. Go ahead.

Yeah, well, exactly. And that's the that's what I mean by the they they've said, hey, we're gonna spend this money, so it's now over there. It's like we've created this bucket of money, go transform, go on, all of you, go, go, go. Yeah, but versus realizing that, well, they've also got a piece to play in this, they have to change their behaviors, they have to look at how they um act, and that's what is going to uh actually empower the transformation to be successful. And if they don't follow through on that, that's often where things start to get uh come unstuck.

Well, when I work with um teams or scrum masters working with teams, I often tell the scrum masters that the teams will test them. They're gonna come to, in a retrospective, they're gonna come up with something which which they sort of don't really need coming out of the retro, but they want to find out how serious the change effort is. And I think that's exactly what we're talking about here is if you're working with executive leadership, part of it is bring a decision where they're going to have to make a trade-off. They're gonna have to choose between that objective and maybe other things that maybe in the past they've fallen back to and promoted. And so to see there um how serious and and there's an education, but you can't expect them just, you know, from standing up and going, we're gonna do this, to immediately make those changes. Of course, they're not going to. They need to be aware, educated, know what's impacted, supported by the right, you know, coaches, guides, whoever they're partnering with. But there is that element of okay, if we're serious about this, this is we're gonna have to stop doing this, or I need an extra X, Y, and Z, whatever it might be. How do we bring that to the table and kind of rod the boundaries of how much commitment they're bringing?

Yeah, take things and saying, okay, I'm gonna take this on, I'm gonna own it, and I will actually deliver on this. And uh in return, I need you to deliver on this and that that actual piece. One one of the pieces that um or one of the way frameworks or models that I I always um like to use around that is uh Mark Burgess's uh promise theory, the the whole the uh that uh promises work two ways, like if uh I make a promise and the the intent comes back. So so the that I find is a is a beautiful model.

And it also explain a bit more, right?

Two sides to the promise, what exactly uh so if uh if I promise you um that I will deliver on this, you promise me that you'll be that you'll support me in that and that you'll accept it and that so then this way um those promises go both ways, and we make commitments and that we agree that this is what's gonna happen. Um first encountered that, of course, with CF Engine back in like '97 or something, but it's totally different use case for it. But the you've since applied the same logic to that organizational structures, which uh I find quite interesting.

Yeah, no, that's pretty interesting. So so let's uh we I think we've kind of beaten that one, but I just wanted to pick up another thing on this, which is we've we've looked at okay, are you serious about it? But the question said, how can we bring senior leadership along on the journey? So what do they look for? What can we give them? And and I'm gonna go back to Cotta, the conversation we had last time, which is which is is basically communicate, communicate, communicate, bring them along on a journey literally means let me tell you where we're going, let me tell you how we're gonna get there, let me tell how you can support. And I mean, what else would you add? I mean, there's communicate, communicate, communicate, but what else?

Uh well, uh with them is always a is a good one, is understand what's in it for me because this is a uh incentives. I mean, what are they incented by? If they're if they need to have success in certain areas for there's something that they need to achieve, show how what you want to do is going to help them achieve that. Uh and then that they're gonna be much more bought into it. This, like, hey, that that you want to be able to ensure uh currency across every system, your entire environment, because you need it to satisfy these security requirements. Well, let me show you how these changes to the the system of work that I'm introducing will enable that to happen. Uh, this kind of piece of showing how the direct changes will support something that that person you're talking to really needs.

Yeah, I I think that fits together really well with that promise is a two-way street, right? The promises because part of this is we're all human beings, right? And we can sit down and say your title is here, mine is there, and I need to do this and you need to do that. But the reality is we're we interact with one another in the way we do socially, right? So we're going to do the same thing of look at if you bring this to the table, I can bring this to the table. Or if I can bring anything at all to the table, what would be top of mind for you? Like if I can bring something to the table, which thing would would kind of be useful to you the most? So that just exploration and understanding of incentives, of the pressures that they're under, of the conflicting demands. I mean, I always I always say with leaders is they're desperate for people who can solve problems. They they're looking for people they they have problems, galore, right? So they need people who can get out there and solve problems. And transformations are often about building teams that can go and solve problems. There's a match made in heaven there if we can understand which problems need to be solved.

I I have a third one. There's a there's another one. There's more, right? Yeah, the the the other one is find out um what their influences are, find out who influences them and who they listen to. Uh and because if you can't convince them directly, convince the person that can convince them. Yeah. Which we we talked a bit about uh last time around as well.

I I really, you know, looking back on that conversation, it really pulled out the because sometimes I get bogged down with oh, we've got to do task A, task B, task C, give this, this, that, and the other happening. And what really struck me coming from there is that book review that we did was how much of it is communication and just questions and conversations and you know, let me share what's going on over here and tell me a little bit about what's what you're struggling with in your area. And I think we sometimes forget that, right? Yes, yeah, very much so.

Uh anything else you would add to that?

I I think uh so one final thing, maybe just to kind of put a bow on it, if you like, which is I remember a lot of the time when we were coaching internally, we'd have post-it notes and scribble drawings and whiteboard diagrams. And what I've been learning in the days of sort of remote work and just you know interacting with individuals where you're not necessarily able to take them over to a board and describe things, is the importance of the artifacts that you leave behind. And that the time spent to really use their language in those artifacts so that they feel connected to them, but also like it just raises the credibility of the change. And I think that's something that you know, when I look, we could we should talk sometime about transformations and how we we've not necessarily always done a good job in the agile community around that, but really just that you you know, we've got to help people talk to other people, and that's a lot driven by the pieces of information artifacts, whatever it might be that we leave behind.

Yeah, I think that's a that's a good point. And uh it's it's it's interesting as well in the more virtual world that we're living in. We actually create even more of these artifacts than we did before, uh, and they are a lot less transient. A lot of the time, those post-it notes come off the wall or they fall down because we didn't peel them off the pad properly. And uh then uh that piece of information gets lost. And uh so so what else might you want to cover in this little uh chat today?

Um there's the opposite side, right? And I just saw one of the other questions here, which is um, how do we measure the success of a leader's contribution? So if we're looking out to the leadership saying, okay, how do we bring you along? The other one is okay, so how how do they contribute? What's the bottom line in that sense? Well, have we been successful? Well, it but it's different, isn't it? So if you're if you're a leader, you're wanting to see your strategic objectives being met, the problems that you the people have kindly uncovered and the incentives they've uncovered being met, and so on. But there's another thing, isn't it? There, there's it's the two-way promises piece. So, what come how do we measure that success for a leader?

So, some of the interesting ways that I've seen, which I quite like, are things like if if somebody says they have an open door policy and uh like how much how many meetings do they have in their calendar? Like, have you managed to actually free up the time to be available? And like, how long what's the lead time on being able to get time with the leader? Uh so looking at it from that perspective, how can we start to look at what does it take? Like, how are we being effective as leaders? Are we available? Are we there to answer the questions when needed?

That is fantastic. I'm just smiling, just thinking of how many leaders where you look over the calendar and of course they're eight to ten hours a day blocked and so on. Yeah. So are they available to the team? And that I I really like the um the sort of cycle time on feedback decisions. You know, you go to them with a decision, do you get a turnaround time which is a day or less, or do you end up waiting and having to? There's one of the things that I find quite interesting is do you have to, if you ask for a decision, do you have to make a note so that you remind yourself to go and check for an answer within a few days or a week or whatever it is? Or can you ask for a decision and you know the decision's coming back before your note is going to get triggered?

Yeah, that's an interesting one.

Yeah.

Because I find myself make a lot of those notes. Uh that's to remind myself about the decision I'm supposed to make, of course.

Well, that's because you're a leader that's contributing, you know, making sure you're doing it well. But it's uh, I mean, I I think that's a fantastic one. Um, that contribution. One of the other conversations you're asking about this sort of two-minute piece that I look at there, one is how you're growing people around you. Right. Uh and I think there's some great leadership development models, and we all know that great leaders grow leaders around them. So if you think of that contribution, I guess part of it is who, in addition to that leader, is being recognized, is getting put in front of the company at a town hall or whatever it might be, but who's who's actually coming up from their ranks, the team that they're working with?

Yeah, I like that one. Yeah, it's uh I think it's a critical one. And I know some of my proudest moments as a leader have always been when uh I've managed to somebody I've been working with has become successful and uh gone on to great things.

It's it's I find it it's anybody who's got kids, it's like automatically they understand it. Because as a parent, when you're sitting there and you're watching your kids cross various stages in life, you know, in various positions, that's the whole feeling because you're not doing the work for them. They're doing it all most of the time, right? But you're you're it's that reflected glory from it. And I think the the best leaders are the ones who they don't have to be in front of anything, they're actually there growing the people around them and people just like they're creating that sort of the next generation continually for sure. I I've got to say, I think there's more to it than that in terms of that contribution. So I'm just trying to think of like I think a lot of it is the safety aspect of the tough decisions. There's nothing worse than having a conversation where you know there's there's this tough decision coming up in front of you and the leaders making you sweat instead of stepping out and saying, you know, I can see this is gonna be do we need to go and talk about this thing? Can we can we bring that out into the open and have a safe conversation? What do you see happening? What do you need to see happening? Why do you think it's not happening, and so on? But instead of that nasty feeling where you you can see it coming and nobody's helping you to bring it out.

So so I I wonder if there's a uh there's um something I've seen effectively used in that is like the like an anonymous strength finder survey and trends of like how do people feel about um would would you recommend working for this leader? Well, 360s and things like this, right?

It's it's actually uh again this comes back to that whole conversation we're having about cotters, which is the time invested in building rapport, in vulnerability and building understanding and building trust on your teams. When you've got loads and loads of things to do, it feels like it's the wrong thing to do, but every single time those investments pay back tenfold.

Yeah, yeah. Awesome. So uh with that, should we wrap it up for this conversation?

Been an interesting conversation, actually. I kind of liked the way that came together. But maybe uh we can ask our listeners. Yes, we'll ask them later. So, yeah, for sure, like, uh maybe follow us if it's you're listening to us for the first few times. Um, but definitely give us some feedback on feedback at definitely maybe agile.com or in the in the comments below. And uh we'll look forward to maybe picking up a similar conversation in the future.

Yeah, yeah.

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Awesome. Until next time. Until next time. You've been listening to Definitely Maybe Agile, the podcast where your hosts Peter Madison and David Sharrick focus on the art and science of digital, agile, and DevOps at scale.