Chief Content Officer,
Techstrong Group


In this Digital CxO Leadership Insights episode, Mike Vizard talks to Teleios Strategy CEO Drew Yancey about how to overcome the gap between planning and execution that all too often scuttles digital business transformation initiatives.


Mike Vizard: Hello, and welcome to the latest edition of the Digital CxO Leadership Insights series. I’m your host, Mike Vizard. Today we’re with Drew Yancey, who’s CEO for Teleios Strategy, and we’re talking about execution, and hopefully not the kind that you might experience in a, shall we say, totalitarian environment, but one more where we’re talking about business strategy and how to bring it through fruition. Drew, welcome to the show.

Drew Yancey: Thank you so much for having me, Mike. Great to be here.

Mike Vizard: So many digital CxOs have awesome plans; they look great on paper, but when it comes to actually implementing, we run into all kinds of issues. What do we overlook every time we come up with some sort of grand strategy, and it seems like we run into the same execution issues over and over again, but what are they?

Drew Yancey: You make me think of a comment a friend of mine, who’s an executive in the space that you just described, he said, “You know what? I’m really struggling with all the idea fairies we have running around here.”
It’s a challenge, because on the one hand great plans start with great ideas. On the other, an idea is not a plan. It doesn’t get us to result directly. So more than anything, what I often tell people, Mike, is we need to shift our mindset when we think about strategic planning. Traditional strategic planning, which I am not a fan of, separates, it bifurcates plan and execution. And what that ends up doing is it creates this silo effect in our mind where we spend a lot of time perhaps as an organization or as in a leader coming up with a plan, but then we leave execution to an afterthought as if that’s going to take care of itself.
The data does not show that. What the data shows is that for most organizations, they’re liable to only actually execute about 30% of any strategic initiative that they’re going to come up with.

Mike Vizard: Is that because not everybody buys into the plan? It seems like sometimes the execution is left to folks that either have, shall we say, a competing agenda or may not be full believers in it or simply don’t understand the plan.

Drew Yancey: Lack of buy-in a major reason why there’s an execution gap, but it’s important to know, Mike, that that’s just one. There’s a variety of ways that that execution gap can transpire. And being aware of those is obviously an important starting point, and then shoring up your planning process so that it offsets those is another key step here.
Some of the other major reasons why this execution gap exists, we’re not clear enough about our objectives. We stop at the level of priority, meaning we might identify as part of a strategic plan we want to implement a new CRM technology. That’s a priority. That’s sort of like the New Year’s resolution version of I want to lose weight. Until we turn that into a clear objective, “By June 1st we will have implemented a new CRM technology that accomplishes X, Y, Z.” Now we’ve got something we can work with because taken a priority and we’ve made it into a clear objective, more of a target that we can aim at.

Mike Vizard: As we think about that, a lot of times you’ll see organizations will create a, quote unquote, for lack of a better phrase, tiger team that’s going to go execute some strategy or some idea, but almost invariably they wind up finding themselves in some sort of branch that somebody’s busily sawing off from the main trunk of the tree. And how do we find ways to innovate, which you need a tiger team to do, but then bridge that divide when we want to execute it at scale?

Drew Yancey: Yeah, great question. Any great tiger team, and I’ve spent many years of my career consulting large Fortune 500s where they have the resources to create an innovation team or a tiger team, but whatever you call it and whatever it is, that team has to have a mandate where it understands its role as a convener of innovation. What I mean by that is it is curating a culture of innovation throughout the organization. It’s making sure everyone understands that new value creation, which is how I think about innovation, that’s how I define it, is every single person’s responsibility. We might have a team that’s getting out in front and creating some structure and some process, but that team really needs to be clued into the needs of our internal and external stakeholders.
There’s been a shift in the strategic planning world over the last decade, sometimes referred to as open strategy. And open strategy is a term that can be abused a little bit, but the basic premise of it is, Mike, that we’re opening up the strategy room so that it’s not just senior leaders or a couple of tech wizards that are responsible for innovation. They might be some spearheading of a team, but everyone’s got to own innovation.

Mike Vizard: I think it’s easier within a particular silo to innovate than it is to do something that crosses multiple silos. You’ll see a marketing department do something interesting because they’re all reporting up to the same person, but once you do something a little more ambitious that crosses marketing, sales, manufacturing, accounting, it becomes a little more challenging. And a lot of these folks are sometimes working across purposes with each other. So how do I mitigate that or at least marginalize it some so that I can get everybody on the same page and at least move it in the same general direction?

Drew Yancey: Yeah, great question. A couple of key strategies here. Number one is we want the team to reflect the cross-functional nature of the initiative itself. So if we’ve got an initiative, an innovation initiative, that’s going to cross functions, then we need representation from each of those functions on the team itself. So that would be one key step.
Second is, once that team is established, we’ve got to have a shared language and expectation for why are we doing this. Whatever initiative we’re talking about, what’s the ultimate value that we’re after here? That value can’t be silo-specific. This can’t be a zero-sum game. “We’re only doing this for marketing,” or, “We’re only doing this for manufacturing or operations.” We want to create a unified reference point that we can all say, regardless of the function that we’re in, here’s our big why behind this.

Mike Vizard: It seems like we’re on the cusp of some major transformations that all trace their way back to two letters, AI. What is your sense of … Are organizations prepared for this? Do they really understand enough about their own processes to figure out how to apply it, or are we just going to be on the forthcoming year of experimentation?

Drew Yancey: I have no idea what you’re talking about. AI? This is a new thing. This is such an interesting question because people tend to be on one of two extremes here. Whether it’s AI or some other form of technology, one extreme is just to embrace it uncritically. “This is the best thing ever to happen in the world, let’s go all in.” The other end of the spectrum is to be paralyzed in fear. “This is going to destroy jobs, it’s going to eliminate opportunities. It’s going to expose our weaknesses in our organization.”
Probably no surprise to you, Mike, I’m going to recommend more of a balanced, middle-of-the-spectrum approach here. Let’s be thoughtful. Let’s try to find first and foremost the opportunities that this set of tools can create for us and our stakeholders. I emphasize the term “tool” because that’s ultimately what it is. It’s a tool that needs to be applied in the right way, and that’s going to require some discernment. So the worst thing we could do is immediately react to either one of those ends of the spectrum and not critically think and explore the value that could be here for us.

Mike Vizard: Do you think leaders are going to have to get down into the weeds a little more aggressively, because a lot of the times I’ll talk to folks and I’ll be saying to them, “Hey, you understand your processes?” And they’ll say, “Oh yeah, absolutely.” And then roughly sometime after that second beer, it becomes clear that they have no idea what’s going on in their rank and file, and there’s more exceptions than there are rules in the processes. So do we need to get back to the fundamentals before we start thinking about the next great wave of automation?

Drew Yancey: That’s an interesting observation. What do you mean by getting into the weeds? What does that mean to you?

Mike Vizard: Well, it seems like a lot of them don’t always know how processes work within their organization. They’re at a vice president level. They’re a little bit far removed. The last time they were down at that level was four or five years ago, and it’s evolved in a lot of ways that they don’t know anything about, but they’re still making decisions about it.

Drew Yancey: Yeah. Yeah, and why I wanted to clarify that is because I agree with you. If we’re constructing the idea of getting into the weeds in the form of micromanaging, then absolutely not, but I don’t think that’s what you mean. I think you mean it’s more of a growth and a learner’s mindset, to make sure that if we’re a senior leader, we’re listening to, we’ve got an ear on the front lines.
And so great leaders in this space are leaders that are very inquisitive. They’re very curious. They ask a lot of great questions. They recognize the limits of their own knowledge. They create an environment of psychological safety where those that are reporting to them can be blunt and honest. All of those factors I think really will make the difference long-term as to whether a leader is going to be successful in the implementation of this.

Mike Vizard: We have been struggling with this issue since time began, since the first time there was an organized anything. Is there something in the human condition that just prevents us from executing as sharply as we would like to, or there are instances where people have been successful, but I wonder if that’s more of the unique case than the rule. So what plagues us?

Drew Yancey: That is a great question, and there is. Human beings, for as much as we’ve evolved as a species, Mike, as much as we’ve accomplished as a species, are still at the end of the day fairly simplistic, meaning we can’t handle a lot of complexity at once. We haven’t become magically better at multitasking. You look at the research that’s out there, depending on the particular study, I’ve seen numbers anywhere from five to 10, the amount of things that we can focus on meaningfully at any given point in time.
So when we think about an execution gap, it makes sense that the more complex our organization becomes, the more complex our environment becomes, the more variables we have to factor in and control for, the more difficult it’s going to be to remain focused and to radically prioritize. This isn’t something that we’re ever going to eliminate as attention, it’s something we need to be constantly aware of and manage well. A great strategic plan is not one that has 25 different initiatives on it. It’s one that’s clear and concise and gets to the heart of where we’re going as an organization and how we’re going to get there.

Mike Vizard: It also seems that there’s a tendency to sometimes cast aspersions on others. There’s an old joke about a football coach whose team was pretty awful, and the reporters asked him what did he think of his team’s execution today, and his answer was, “I think it’s a pretty good idea.” As funny as that may be, there is a tendency to blame the squad too much, and maybe the leadership needs to figure out, “Hey, it’s not the squad.”

Drew Yancey: Absolutely. Unfortunately, and you would probably have similar experiences, we’ve interacted with leaders who are at the helm of an organization that’s not executing, and that leader ultimately believes it’s someone else’s fault.
And what I believe defines true leadership in this space is that a leader recognizes that ultimately he or she is responsible for the results that the organization is getting. If I don’t like the results that my organization is getting, then I ultimately need to be responsible for that. Then that doesn’t mean that I am responsible for every action item that might be in a strategic plan or that I’m doing everything, the exact opposite, that I’m leading effectively through other people.

Mike Vizard: Ultimately, what’s your best advice for folks? Do I spring for a therapist for everybody and that’s what they’re going to need, or do they develop a dependency on some other substance to get them through the day? I mean, these are the two extremes, but how do I approach this in a way that preserves my sanity?

Drew Yancey: Yeah. Yeah. Obviously every scenario is different, every application of the execution gap is a little bit different, but I always go back to three basic questions. Whether we’re talking about an organization, Mike, that’s involved in strategic planning, or we’re talking about a leader who’s creating a tactical plan for their function, three basic questions.
Number one, where do you want to go? And be as specific and as vivid in the answer to that question as possible. In my work with clients on strategic planning, we go through an exercise where we create a vivid vision, and it’s an answer to the question, “What does amazing look like for our business in three years?” I won’t go into the components of each of those words, but they’re intentionally chosen to maximize the success of a plan.
But let’s keep in mind, a strategy is an answer to a “how” question, “how do we get to where we want to go?” It is not an answer to a “where are we going question,” or even more importantly, “why do we want to go there.” Oftentimes leaders will tell me, I need a strategy, but what they actually need first is a vision that’s going to drive that strategy. So that’s question number one, “Where do I want to go?”
Question number two is, “What are my vital few?” What I mean by that is if you think about what you want to accomplish, say, over a three-year period, there’s only going to be about three to five truly strategic initiatives that warrant your time and energy. We’re not saying that these are the only things that need to be accomplished. We’re saying these are our cornerstones, these are our centerpieces. They could be something related to sales or operations or leadership or all of the above.
And then the third question is, “What are my clear objectives?” So the final piece of the puzzle is let’s take those initiatives and turn those into clear objectives with measurable key results. What I described you a little bit earlier about a priority being, “I need to get A CRM technology,” and turning that into a clear objective. Whatever context we’re talking about, whether it’s the business or a team, if we can answer those three questions, we’re well on our way to closing the execution gap.

Mike Vizard: All right, folks. Well, you heard it here, that execution gap starts with that person you look at in the mirror every morning and then it goes out from there. Hey, Drew, thanks for being on the show.

Drew Yancey: Thank you for your time. Great discussion.

Mike Vizard: And thank you all for watching the latest edition of the Digital CxO Leadership Insights series. You can find this episode and others on the website. We invite you to check them all out. Until then, we’ll see you next time.