Ep 244: How Do You Get Senior Leaders to Stay Strategic? (First, Change the Question)

C-suite leaders often know their teams should be thinking strategically, and yet under pressure, those same teams keep dropping back to the tactical level. In this episode, David Wheatley, Dr. Rick Eigenbrod, and Dr. Judy Brown unpack why that keeps happening and what to do about it.

The conversation starts with a reframe: the question "how do I get them to be strategic?" is itself the problem. It creates a dependency that almost guarantees teams won't take ownership. From there, they explore what actually drives the regression: unclear shared meaning of "strategic," metrics and bonuses that reward tactical behavior, the boss's own anxiety signaling what really matters, and whether team members are developmentally ready for the altitude being asked of them.

Listeners will come away with a sharper diagnostic lens and a set of better questions to ask before trying to change anyone else's behavior.

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Transcript

David Wheatley (00:10) Well, welcome to this episode of the Humanergy Leadership Podcast. I'm David Wheatley, your host, and I'm joined by my good faithful doctors — Dr. Judy Brown and Dr. Rick Eigenbrod — who are my two mentors. I get in trouble for giving away their age, but they've got a combined significant number of years of doing this work ahead of me. So it's great to have conversations with them.

I posed them a question recently to noodle on, and then we'd have a conversation about it today: How do strategic leaders get their team to stay strategic? It's something I've been coming across a lot in my work, so here we are. Rick, I think you're going to start us off.

Dr. Rick Eigenbrod (00:57) Okay. I realized what a rich question it was. As I thought about it, I felt like I was peeling layers. And the first thing that came to mind — would you say the sentence again, please, David? I'm going to jump in right after.

David Wheatley (01:13) I'll make sure I get it. How do strategic leaders — I'm talking about C-suite leaders — get the team to stay strategic?

Dr. Rick Eigenbrod (01:23) Simple answer: they don't.

David Wheatley (01:26) All right. You've been listening to the Humanergy Leadership Podcast.

Dr. Rick Eigenbrod (01:29) Because I think, David, we hear in that question a very familiar set of dynamics. The minute you say "how do I get them to," you're already in trouble. You've set up a dependency relationship. You can almost hear yourself go back to when you were talking to your kids: How do I get them to pick up after themselves?

The first thing is to understand that you don't. What's missing here is — they don't. That's not up to you to get them to. The question is, why aren't they taking on that responsibility? Now there we can really start to peel the onion.

A couple of things come to mind as hallmarks. One is the brilliant work in The Wisdom of Teams — Katzenbach's work — and his distinction between teams and work groups. One characteristic of a team is that they're accountable for the whole. And this team isn't accountable for the whole. The boss is accountable for the whole, which means they become a work group, not a team.

The second is the brilliant insight of Lee Thayer, who said: the problem you name is the problem you solve. And what I think we all see with teams — particularly — is how little time they spend on problem naming. They're so pushed, and feeling pushed, to come up with solutions that the real work doesn't get done. As we've observed with teams, the real work isn't coming up with the answers. It's coming up with agreement on how we name the problem.

A couple of things came to mind. One is that the word "strategic" itself creates problems. It creates a problem of: do we have a shared understanding of what that word means? If I was in a room with them, I'd ask everyone to go to the board and write on a sheet of paper: when we use the words "the need to be strategic," what specifically do we mean by that?

Because until you have shared meaning, you just have a word that everyone thinks they know what it means. We think we have shared meaning, and in truth we don't. So I think the notion of making sure we have that is foundational.

What's the shared meaning? What are we talking about when we say "strategic"? It can be very different. It can have to do with the nature of the task and the work to be done. It can have to do with time frame — Elliott Jaques' work about how far out do we focus. Is that what they're talking about when they say strategic?

So first and foremost, I think he's got to change the question. He can't get them to do anything. The question I would have is: why aren't they? In what way does it make sense for them to behave the way they're behaving?

Dr. Judy Brown (05:31) Does it make sense to them for them to behave that way?

Dr. Rick Eigenbrod (05:35) The way they're acting. Because at one level we're talking about — yeah, we all agree we need to be strategic. But at a much more subtly dynamic level, they don't feel responsible for that. So one of the answers to the question is: in what way does it make sense that they're not being consistently strategic? One answer is because they don't feel responsible to be. He does. He feels responsible to get them to do it.

Those couple of thoughts came to mind. Let me stop there, Judy and David, and see if that prompts any thinking on your part.

David Wheatley (06:13) Well, before we go to Judy — one of the things I've been doing in a lot of these conversations is building what I call an altitude chart. Let's look at the C-suite: how far out should you be thinking? How far out should you be looking? What's the work that you should be doing? Let's have that conversation with everybody. Then let's look at the VPs. How far out should they be looking? What's their work? Then the directors. Same thing.

So that's the clarity piece you're talking about. One of the challenges, though — and I come across this all the time — is that those people got promoted because they were good at the last job. And when the pressure's on, when they're incredibly busy, when there's major change going on, their natural tendency is to drop down a level to where they know they can perform. Especially if the people beneath them aren't performing to the level they'd expect.

So there's this squashing of the organization. And then the leader at the top sees this void being created — which is where the root of the question comes from. We've had the clarity. We know where we should be. And my team keeps getting gravitationally pulled back down to a level beneath where they should be working.

Dr. Rick Eigenbrod (07:44) It's such a familiar dynamic. Basically, what you're talking about is Elliot Jaques' notion about how far out do we work. There's another dynamic where we regress to the mean under the kind of circumstances you described.

So that becomes part of a conversation we need to have with each other. The question is, in a sense, to stop the dependency relationship. As long as I feel responsible for making you responsible, they ain't going to be responsible. So how do we need to change the conversations such that that doesn't happen — and we don't lose sight of why are we looking at the boss? We're accountable for the whole. Sorry, Judy.

Dr. Judy Brown (08:43) The story that comes to mind for me actually has to do with looking at the boss when you should be looking at something else.

I've been really interested in what happens when people think the boss has all the experience and the smarts, and they feel like they don't — because they're junior, or they're new, or they don't want to speak up. And what's the cost to the organization when that happens?

My favorite example is the Air Florida crash that happened about 25 years ago in Washington, D.C. You had two guys in the cockpit: a captain who was very experienced and very sure of himself, and a first officer who was pretty junior and not so sure of himself. It was a lousy weather day.

The junior officer was walking up and down the aisles, looking out to see if there was ice on the wings. And he thought there was. So he would come back and report to the captain: "Sir, I think there's a little ice on the wings." And the captain said, "Listen, we've de-iced once. If we have to de-ice again, we're going to lose more time. We're going to have mad passengers. We just can't do it. We're going to take off."

So he insisted they take off. And the first officer — the young guy — had his hands on the controls going down the runway. The black box recording later revealed you could hear him saying, "There's something terribly wrong here." They managed to get off the runway, but the plane was too heavy with the ice and crashed into the water just short of the 14th Street Bridge.

The captain and first officer died, and most of the passengers did too. And people say to me, but what could he have done? The captain insisted they were going to take off. To which my answer is: you can't fly a fully loaded plane with just one person in the cockpit. He could have gotten out of his seat and walked out the door off the plane. They would not have been able to take off.

And then people say, he probably would have lost his job. And I say, true. But what he lost instead was his life.

So this question of rank pressure — when there's uncertainty on the part of somebody who really is seeing something, but the culture isn't such that they can say it. I imagine a conversation where someone comes up to a CEO who wants to be strategic and says, "Look, what I'm seeing is this." And the boss says, "You're in the weeds. We told you to stay out of the weeds. We want you at a strategic level." When the news from the weeds may be the very thing that keeps the organization from imploding.

This tension between what people operating at that level can see, and the impact that insisting on a certain altitude can have on dampening the information you actually need to move ahead wisely — that's what's most on my mind, given the way you guys kicked this off.

David Wheatley (12:22) So the first question should be: do I understand why they're operating at a level below where they should be? Am I open to that? Am I listening to what's going on?

That takes me down one of two paths: either I understand it and they're choosing to drop down because they're more comfortable there, or I now understand it because there's something they're seeing that I don't have visibility to — and I need them to pay attention to it.

Dr. Judy Brown (12:55) Well, I might say it's not one of two paths — it's one of six paths, because Rick's got at least a list that long. They're seeing something I'm not seeing and think is important. Or — Rick, what were your other things?

Dr. Rick Eigenbrod (13:31) I think what you two are offering is really rich. It brought a couple of other things to mind. One is: people don't do nonsense. We hate nonsense. So we say, this doesn't make sense — they're not being strategic, we agreed they would be, why would they do that? But their behavior makes sense. From their point of view, their behavior makes sense. Our job is to get inside their sense-making process, which drives their behavior.

He thinks they're not being responsible. They think they're being sensible. So what's actually going on?

One thing you could look at is the old notion: we don't measure what we get, we get what we measure. So let's go to the metrics. What are we really measuring? Are we measuring behaviors we've defined and agreed upon as strategic? Or are we really measuring productivity, the old metrics from the level below? Do we have agreement on how we know if we're being strategic or not?

The other thing is the reward system. They may say, it's fine and dandy for you to say we should be strategic, but my bonus depends on something much more tactical or productivity-based. You can talk all you want about being strategic, but the reward system is set up to reinforce these behaviors. So it makes sense for us to do that.

And these are really subtle. We don't think about them. And the more anxious we get, the less likely we are to think about these systemic drivers.

There's one more I've watched: their response to the boss's anxiety. If the boss comes in and everything they talk about, everything they emote about, has nothing to do with strategy, guess what the team's going to respond to? We know what the boss is anxious about. Our job is to keep the boss from being anxious. And all the boss talks about is the numbers, the productivity, the delivery dates — all the things that are one level down. While in theory, we should all be working at this level. It's a very subtle but powerful driver of behavior.

David Wheatley (17:08) That's a great example. I can think of three or four real scenarios across different industries where it's the same thing. The leader wants everybody to be strategic — looking up and out — and at the same time is constantly looking at this year's performance and the fact that the year is getting shorter. Her anxiety goes up when that number changes, and the organization gets compressed.

What I'm hearing from you, Rick, is that the first two questions for our CEO here are: Do I understand why they're operating too low? And second: What am I talking about when I get in the room with these people? Am I driving some of this — this dropping of altitude?

Dr. Rick Eigenbrod (18:13) Yeah. Can you imagine a boss going into the room and saying, "Look, we have a plan. That plan has to do with three years out. We are not going to make the productivity numbers this year. I don't care. That's not the point." And they go, "Well, what about our bonuses?" "Let's talk about that."

I remember talking with the head of a big financial services company. One of things they did — and this is hugely unusual — they set goals. If you make the goals, you get the goodies. If they didn't make the goals, they paid up personally. If they had a financial goal and didn't meet it, each one of them put up money out of their own pocket to meet those goals. So can you imagine some version of that where the boss says, "We agreed this needs to be done. It's not happening. And that's not what's really important right now."

David Wheatley (19:36) I'll flip the script on you a little bit there, Rick. What if it's a large urban school district, and the superintendent is saying, "But when you say this year's results don't matter — that's 100 kids I've let down who are already behind."

Dr. Rick Eigenbrod (20:03) Well, I'd have to think about that. I get it.

David Wheatley (20:08) And it adds a complexity. That's the interesting thing, isn't it? The complexity drives urgency for today's results. But I want people to be thinking about what we're going to do in the next three years to impact the long-term sustainability of the district.

Dr. Judy Brown (20:28) That would make me want to ask: where, when we look around this organization, can we see instances of teacher behavior, learner behavior that has resulted both in improvements in learning and are at a strategic level?

Rather than divide the world into two things, the question in the school might be: out of 50 teachers, there may only be two you could cite who are managing to do this — who are keeping their eye on what we've called "looking up and out" and still getting remarkable results with the kids. That's when you turn your organizational focus to that place where it's working. And figure out how to run more and more experiments on that.

David Wheatley (21:29) The equivalent at that level in a large school system would really be the principals. Which school is actually rocking it? Find out what that principal is doing that's generating that impact, because that's the strategy. That principal is drawing kids to the school — kids want to go there because of the results they're delivering, which is the strategic side. And there must be something happening today that's improving results for that school, which is the tactical side.

You're saying: it's a balance between those two. Let's look for those hotspots and try to replicate them.

Dr. Judy Brown (22:05) That's actually a really good term for it — hotspots. And it might be beyond what you usually think you're looking for. The principal may be part of the answer, but it may also be that the chemistry in the place is such that the parents are deeply involved, there are all kinds of supports being created for the kids. It's just a different kind of place.

But if you look further and further, you'll see these bright spots. And I think there are two questions: how do you run experiments where you can have both? And how do you watch for situations where you're getting the results you need but you're not taking your eye off the ball?

Dr. Rick Eigenbrod (23:03) Yeah. Two things you two triggered in me. One is: in the school system, David, it really reminds us it's a system. To what extent have we communicated to the community at every level that they understand this year may not be what we want, but here's where we're going? The system isn't going to let us have a broader look unless the system has a shared understanding and a shared perspective.

The other thing that comes up is quite sensitive: do we have people on the team who are capable of doing what we're asking them to do?

Dr. Judy Brown (24:24) That's right.

Dr. Rick Eigenbrod (24:25) Are they developmentally, if you want to put it that way, at a stage where they can do what we're asking? We can look at Kegan's work and the levels at which people operate. At the lower levels, everything is defined by "what's in it for me." The next level is "what are the rules — tell me the rules and I'll abide by them." As you move up, they can handle higher levels of complexity, they have an internal locus of control rather than external, and so on.

David Wheatley (25:21) I'm putting up on the chart — Kegan's on the right-hand side here, for those who are watching. What I've done is put three different models on the same chart: Humanergy's Four Choices, Maslow's hierarchy, and Kegan's developmental stages. They have a similar kind of alignment, and I'm finding more and more that people who are at the bottom levels are nearly incapable of making transformative leadership choices.

Dr. Rick Eigenbrod (25:49) Exactly, David. Because we don't think that way as business people particularly — it's not built into how we make assessments. But I have a line that I may have stolen or may have made up, though I think it's brilliant: who goes into the room has everything to do with what comes out.

Sometimes we ask people to operate at levels they are developmentally not capable of operating at. And if they're already in the room, it's really tough to acknowledge that. But one of the things you can do is: watch their behavior. You don't have to give them a test, although there are fabulous tests. The Leadership Circle, by Robert Anderson, is an integrated model of development that connects levels of leadership with the capacity and productivity of the organization. It's real. We're coming to understand it's really real, this function of developmental level.

So: are these folks capable of doing what we're going to ask them to do?

Dr. Judy Brown (27:35) Which makes me ask: what are we doing to provide developmental experiences for our people? This has to do with how we maintain a rich bench. We can't just scrape off everyone who simply can't do this. How do we have a deep bench? How do we have the right coaching, developmental experiences, mentoring? And how do we manage to have serious conversations about this all along the way?

An idea came to mind, David, when I was looking at your charts. I thought: this is an argument for multigenerational teams. There is power in diversity of all kinds to get what we're talking about. But one of the things may well be multigenerational.

David Wheatley (28:48) It's interesting because in some ways Rick is saying: do we have the raw material? And you're saying: do we have the program to get the most out of that raw material?

One insight from talking with someone at a school district I worked with: how involved are the grandmas? There's quite a spark in getting the grandmas involved because they carry such power and authority in the community. I thought that was a genius idea.

The other thing that comes to mind as you two were talking: in the rest of the world, sports leagues are very performance-based. In America, it's quite the opposite — if you come last, you get the best draft pick next time. But in the rest of the world, you can get promoted. You can go from the fourth or fifth tier of soccer and slowly work your way up.

As people familiar with Ted Lasso and Welcome to Wrexham now know: the team that wins the championship in the second tier gets promoted to the Premier League, and they often ditch half their players — because they don't have the raw material to survive at that level. Some players get transferred back down. But some do have the raw material, and if the club has the development program, they'll keep and develop them.

That practice — of reviewing your team when you grow dramatically — we see the same thing in mergers. A leader who could run a $300 million organization is now leading a $600 million organization. Do they actually have the capacity to do that? Some do. Some need to go back and run another $300 million organization.

Dr. Judy Brown (31:01) I want to take another example of this sort of thing. There's a wonderful story at Ford Motor Company about a team that was put together with impossible financial demands and a very quick deadline, and managed to produce an extraordinary vehicle. They saved incredible amounts of money for Ford and finished well ahead of schedule. Everybody was so proud.

And then, when it was all done, they gave them all kinds of recognition — and broke up the team and sent them off in different directions. Because they thought they were individually so smart that they could do that kind of work anywhere. Without realizing it was the capacity they had developed as a team that made it possible.

So one of the questions is: if the principal at one of those schools has an incredible teacher team and support team, the temptation may be to ship the best people off to other schools. But the wisest thing may be to keep that chemistry together, because it is collectively more powerful than the individual parts of it.

David Wheatley (32:28) And the challenge would be: what can we learn from that to replicate it — not to take it and plant it somewhere else, but to replicate the thinking.

What's interesting — in my soccer world — is you can see a coach with a team of the world's greatest players not do very well. And you can see another coach with a team of mediocre but good players do really well. The difference is how that coach is managing the team, the collective, the alignment. How well are they fighting for each other? How aligned are they to the vision?

So it comes back to: are we understanding why they aren't playing for me? Are we talking about the strategy? Are we aligned on what that looks like? Doesn't matter whether you're playing football or running a credit union — it's the same keys, isn't it?

And I think one of the challenges is that sometimes it's brutal. You have to cut players.

Dr. Rick Eigenbrod (33:38) Two things you two said that I want to underline in different language. One is this fundamental understanding from Robert Anderson's research: the developmental level at which the people leaders operate will determine the performance of the organization. It's physics. It's a rule of nature. If you take just one leader, it translates to: the company can't outgrow the leader. And you can extend that: the company can't outgrow the leaders.

The second thing is: who comes into the room is hugely important. When I talk with leaders about their high-value contribution, I say you should be focused only on your high-value contribution. And they go, "How do I know what that is?" It's what you and only you can do. And one of the things any leader on any team can do is decide who comes in the room and who doesn't.

And David, I want to come back to something from the Wisdom of Teams — what you said about the Ford team. There are two or three hallmarks of teams versus work groups. One: accountable for the whole. Two: they produce results greater than the sum of the parts. And that's what you're saying is possible when you do some of those other things. We have example after example of where a group can produce results greater than the sum of the parts.

David Wheatley (35:28) And you still need the raw material that's capable of contributing there. There's a certain baseline required.

Dr. Rick Eigenbrod (35:34) Yeah. There's a certain baseline at which you have to operate. My friend Jean has a wonderful thing she does with teams. She walks in and asks: "What does this team need to produce, create, and be?" Nobody can say a word. They write on cards.

Dr. Judy Brown (36:05) What are the three words again, Rick?

Dr. Rick Eigenbrod (36:09) What does this team need to produce, create, and be? Notice the "be." And at that point, if you said, "Okay, let's discuss," you know what would happen — the most verbal people would dominate. So brilliantly, she says, "Okay, everybody write one thing on a card." The cards go in the middle of the room. And you can't talk. You have to start wandering around the table, clustering where things cluster. People make a cluster here, someone says "no, that doesn't go there," and you keep circling. What amazingly happens is you get these clusters — all non-verbal. The most verbal people can't dictate. It's serious and genius.

It's the nature of the work — she's come up with a way for the team to tackle the essential questions they need to answer together.

David Wheatley (37:34) So: the question was, how do I as a CEO get my senior leaders to be more strategic? The first answer was: you don't. But then we came up with a set of questions to replace that.

Do you understand why they're operating too low? What are you as the CEO talking about that's driving their response? What are you measuring and rewarding? Where are the executives who are being strategic, and how do you hold them up? And do the rest of these people have the capability to get there — do they have the raw material?

And I think the other thing I heard you say, Rick: the problem you name is the problem you solve. And you named a number of leadership resources: the Leadership Circle by Robert Anderson, Wisdom of Teams, and one I'd like to add is What Great Teams Do Great.

That quote — the problem you name is the problem you solve — is one of the biggest things we found with What Great Teams Do Great. The teams that aren't successful skip what we call the setup box, which is answering those foundational questions. It's really a more complicated way of answering: what does this team need to produce, create, and be? But when teams skip over that and get straight into the "what are we going to do," that's when they fall down.

So Judy, Rick — appreciate the conversation again. Another 40 minutes gone by very quickly. I appreciate your time and wisdom today, and I look forward to more conversations in the future.

Dr. Rick Eigenbrod (39:12) Great fun, guys.

Dr. Judy Brown (39:13) Great fun.