Why Executive Buy-In Needs Both Strategy AND Tactics

Getting executive buy-in for transformation requires more than vision – it demands clarity about what will actually change and how success will be measured. Leaders need concrete details about what will look different in their organization, not just high-level strategy.

This episode explores balancing directive consulting with coaching. Modern transformations benefit from proven frameworks combined with coaching conversations that help leaders navigate challenges personally. We also examine measuring system change rather than just activity, understanding that progress is non-linear and involves experimentation cycles.

Key Takeaways

• Close the Vision-Reality Gap - Executives need concrete details about organizational changes, not just strategic concepts
• Blend Consulting with Coaching - Combine proven frameworks with personal coaching conversations
• Measure System Change - Focus on meaningful indicators rather than activity metrics

Chapters

• 0:00 Introducing the executive buy-in problem
• 1:42 Leaders need conviction and understanding
• 4:22 Coaching vs. consulting approaches
• 7:13 Building the transformation framework
• 10:31 Showing progress toward outcomes
• 14:45 Key takeaways and conclusion

Transcript

Peter (0:04): Welcome to Definitely Maybe Agile, the podcast where Peter Maddison and David Sharrock discuss the complexities of adopting new ways of working at scale.

Dave (0:12): Hello Dave, how are you? Peter, good to chat with you again. Now I know in preparation for this, you had a really interesting problem for us to talk through.

Peter (0:23): Yeah. So I was talking to somebody this past week about a particular presentation they were about to do to some executives. The purpose of this presentation was to get buy-in for a larger transformation and the set of activities that are going to change certain aspects of how this executive's teams work together. Looking through the notes from a coaching perspective, they were fairly well grounded in what we would look for as a directional statement. But what I found missing was a lack of "why would you want to do some of these things?" We can talk about what the things were as well, but more importantly, there was also a lack of "how will you know when we..." What are the results you're looking for? How will we know that if we, for example, put processes into place to ensure that all work is defined as close as we know to being less than three months...

Peter (1:20): We're trying to make work more completable, and then how will we know that that's happened? What is it we're doing there? Why are we doing that? But none of that was being explained. There was this assumption that the other side already knew, and I find this an interesting conversation.

Dave (1:36): There are a lot of things for us to chat around, and I'm definitely going to want to come to the coaching versus consulting mindset that I think we've seen a shift in the industry in recent years. We've touched on that before.

Dave (1:48): But as you're describing it, one of the things that I think is an assumption that we very often have—which is misleading in these situations—is that if we're dealing with senior executive leaders, we need to be strategic and we need to stay strategic and keep them focused on this long-term vision. I think, especially in the current market where results matter, where organizations are looking to make sure that if they invest somewhere, they're going to see a result, there needs to be that tie-in between "Hey, this is the direction we're going in and we feel this is the right direction. You feel this is the right direction. We're very excited about taking you there." There has to be that bit in the middle: "This is what it's going to look like," or "These are the steps we're going to take and how it's going to help you achieve that."

Peter (2:32): Yeah, and that's the key part—giving somebody something where they can hold onto it and say, "Okay, I understand what you're saying to me and I'm bought in. I've read the books, I've seen all those talks, and you've convinced me that we need to make these changes about how we're organizing our work and how we're organizing ourselves and how the teams are working together. We need to make these changes and I'm convinced. I just have no idea what that's going to look like and what's going to change about how we're doing things today."

Dave (3:07): I love the way you're describing that, Peter, because now, if I'm listening to what you're describing and I put myself in those shoes, it's not just "What are we doing? What does that look like in a concrete sense?" There's actually a hidden call-out there which is: if I'm going to lead this, I need to speak with conviction. I need to understand how these things fit together, because if I don't understand it, I can't speak with conviction, I can't get behind it. Either I'm worried that I'm going to get called out when I try to communicate that to my team, or I'm worried that I'm going to get questions which I'm not going to be able to answer. So I think there's a hidden piece in there that we often forget, because it isn't just about...

Dave (3:49): "Here's a metric that we're going to hit. You currently—whatever it is—you're releasing every six to eight weeks, and our goal is to get your organization working together to be able to release every two weeks." Great, but the why, what's going to have to change in order to get there... There's a whole bunch of these things that the leadership needs to understand and be able to articulate in their own way.

Peter (4:12): Yeah, exactly. And I think, to paraphrase, you're saying that leaders are human too. Shock horror.

Dave (4:19): Are we really agreeing to that?

Peter (4:23): Oh, I think so.

Dave (4:26): I was going to say, one of my favorite phrases whenever I'm working with people who communicate to leadership is "leaders have bosses too," and this is what we sometimes forget—that there are layers upon layers and people have to communicate upwards and outwards and downwards. Our job, if you like, is to make that as easy a conversation as possible by really clearly articulating what the benefits are, where they're coming from, why those are the benefits that they will receive because of whatever is changing, and then helping them articulate "Okay, I follow this, but I don't follow that. You're going to have to help me understand where that is."

Peter (5:02): And I think that's actually quite a nice segue into one of the comments you made earlier about the differences between coaching and consulting, especially when it comes to communication and leadership communication.

Dave (5:14): It's such an interesting topic because both of us have spent so much time—and we find ourselves in so many conversations—coaching, because that's really where we spent a lot of time in the last decade or so. And yet, whether it's an urgency or whether it's just that we're dealing with a different demographic, a different cohort of leaders who have different needs... It's more—and more directive I think is too strong—but more of a consultative approach, more of being involved in creating the solution or making decisions around what the solution might look like than it used to be when we were coaching.

Peter (5:52): Yeah, that definition that comes along of how it should be done and what should be there and what artifacts we're looking to create as a part of this. We're turning and telling you what those should be. We're not helping you figure this out yourself.

Dave (6:11): The reality is it's been done many, many times, and so yes, every transformation is unique and it has its own context. But we would probably both agree that not only are a lot of the core ingredients of that transformation similar, if not identical—and we could probably agree on that list of those ingredients and there'd be a lot of overlap there—but also there are some well-established practices that have been proven to address many of those components that we have to pull together, which are a great place to start. So we don't have to emerge things in the way that we had to in the past. There wasn't that necessity to sort of leave a lot of ownership on the table. I think there's this recognition that we can get a head start. We still need a learning organization, we still need to adapt to the context, but we can get that head start in place pretty rapidly.

Peter (7:01): Yeah, because we know what the scaffolding should look like. We know what those first pieces are that we need to put into place. We understand... We've seen what bits have worked in other places. We don't necessarily know what exactly is going to work here—that has to evolve—but the general structure and core pieces of it, we understand.

Dave (7:21): I was going to say, as you're describing that, what I love about where you're going is now you've got the core element of that conversation with your leadership, with those decision makers, because it's an element of not telling them the repetition that they can get everyone, but it's telling them the unique elements to help them understand why you're going left here, not right, or why you're focusing on A before you focus on B, before you focus on G and H, whatever it is. So they're understanding how their context is steering and guiding the direction that they're being asked to lead and buy into.

Peter (7:57): Then, of course, we get into the coaching side, where they run into a challenge with their teams or they're looking at a particular instance of "Okay, this happened today. Could you help me think through how I could respond to this in a different way? What might have gone differently? How is my behavior driving what I'm seeing?" And that's when we get into more of a coaching-type conversation versus the structures and artifacts that we have seen work in other places and know work for getting us to that two-week sustainable delivery-type model.

Dave (8:32): I love what you're saying there again, because I'm just reminded of the fact that it isn't an either-or. We're leading perhaps with a sort of consultative conversation, but it's much better supported through those coaching conversations—individual coaching conversations, both before, during, and after those changes.

Peter (8:53): Yeah, exactly. Because when we look to cement ideas into an organization, then the coaching really does come out. Like spending time thinking about why are we making the decisions that we're making, and how do I need to show up to help speak about this with conviction so I can truly believe in this. There are a lot of those types of things. The one I was sort of... How will I hold myself accountable to doing this? Those questions never get asked.

Dave (9:35): Here's how we know we get there. This is why we're going in this particular path, not a different path that you may have read about, whatever it might be. But then there's an element of "Here's how we're going to help you get there, and you're going to have these touch points," whatever it might be. So you're kind of building that whole package, but it's also very tactical, as much as it's strategic.

Peter (9:51): Yeah, and that's where it becomes interesting, because these are mechanisms that fit into helping put some of the right structures into place within the organization, and they are going to differ significantly across organizations.

Peter (10:06): The pieces that become interesting from that are when we start to look at that strategy piece of it and say, "Well, if we're going to figure out why do you need to go in a particular direction? Well, what is it that you're going to not do, and what is it you are going to do? How do you build strategy that can feed this engine that we're building? And then what are those pieces as they come into this?" That's why it's more of a systemic view of the entire organization. One of the other pieces that we were looking at was how, in addition to properly defining the work and ensuring that the work is well defined, one of the next ones was "How do we make sure that the work will be effective, that we're effective in how we approach it, and how will we know that that is true?" So that was one of the interesting questions to the coach.

Dave (10:56): How do you show that? Well, and I think we're touching on quantitative and qualitative—however you want to look at analytical and sort of sense-making measures. You don't want a single measure, a single metric or KPI. You need to look at a range of different ones and both that kind of balance what you're looking at, so you can see a balanced way forward. I have to say that the "results matter" piece of what the results are and how we can go about achieving it is a really interesting question because we so often get caught up, as we've discussed in previous conversations...

Dave (11:29): We so often get caught up into the progress view—showing activity. "We're getting this done, we're getting that done, look how much activity we're making... progress we're making through this activity." It's much more difficult to show progress towards an outcome because that progress is non-linear, it's not straightforward, it's not guaranteed. So there's this whole "two steps forward, one step back," and that's if you're lucky. I mean very often it's two steps somewhere and you've got to take three steps back and go two steps in another direction. So how do you have those conversations? How do you set that up so that people don't walk out of that presentation and buy-in conversation to say, "Okay, I expect you to hit this level here, this level at that next phase," and so on. It isn't that linear, really.

Peter (12:14): Right, and so that's where, when we talk about what it is you need to have in place, thinking about it not in terms of "All work should be less than three months, because we're going to make sure that it is, and if it isn't, then we're going to go around slapping wrists." It's about "How do we ensure that work is well defined?" Well, the evidence the work has been well defined will mean that when we look at it, we see that a definition of done has been put on with the work, so we understand when it would be completed. We've got it written down in clear language. We can easily articulate to somebody else what is it we're going to be doing and why we're going to be doing it, and we're looking at things from that perspective.

Peter (12:55): We're not necessarily being draconian about this, but we're looking for what are the sort of indicators that we're seeing some of the right things. Once we have that, we still have to look at the outcome. Is this helping? Is the system getting better? Because if it isn't, then we need to look into why. Why might it not be getting better?

Dave (13:15): Again, I'm hearing you say two very distinct things. I just wanted to draw attention to them. One is the change that we're wanting to make. How are we progressing on achieving that change? Whatever that change may be, let's stay with that topic of releasing every two weeks in a sustainable manner. There's that side, but then there's the... That's a proxy for the actual meaningful outcomes we want to achieve through changes in user or customer behavior, whatever that might be, whether it's impact on the bottom line, impact on further engagement, referrals, whatever that might be. And those two things are... One we need to see to make sure we're moving in the right direction towards that goal. That is a proxy to achieving the outcomes that we're looking to achieve as a consequence of achieving process change.

Peter (13:57): Yeah, exactly. So at this point in our conversations, as usual, we can try some takeaways.

Dave (14:04): It's an interesting one. We've covered an awful lot just from that starting point.

Peter (14:06): Starting point of "Hey, I have a conversation to get executive buy-in." Well, I think one of my favorite takeaways from this is the whole coaching versus consulting piece of it and the need for both, and we were sort of touching on when and how both come into play. I think that's an important piece to draw out—that there's value in both and they very much help drive it forward as you start to introduce new ways of working.

Dave (14:40): I also wanted to add on that gap between the strategic long-term objective of what we're trying to achieve and the sort of arm-waving "hopefully everyone's understanding what we're trying to get to," but tying that tactically or much more tightly to that pragmatic "What's actually going to change in your world? Why is it changing? What are we trying to achieve as a consequence of that change?"

Peter (15:03): So many times I've seen that gap where the messaging has been too high level and not clear enough about what the actual changes will be or the outcomes will be. And I think that is really where we're going—that if you're going to be making very large changes across your organization, be crystal clear in your communication as to what people can expect to see as a consequence. Well, thank you, Dave. As always, it's always fun having these conversations, and I look forward to the next one.

Dave (15:36): Exactly, for sure. Until next time. Thanks again, Pete.

Peter (15:37): You've been listening to Definitely Maybe Agile, the podcast where your hosts, Peter Maddison and David Sharrock, focus on the art and science of digital, agile, and DevOps at scale.