Ever been on a sports team where everyone had the same skill and played the same position? Of course not. Yet leaders make a version of that mistake all the time. We build a management team, identify the qualities we value most, and then start trying to get everyone to think the same way.
I know because I did it.
I had an idea of what a strong manager was supposed to look like. More specifically, I wanted my managers to think the way I was trying to think. When someone was great at getting things done but less inclined to step back, consider possibilities, and look several moves ahead, I saw a gap that needed fixing.
Eventually, I realized I was asking the wrong question. The question was not simply, “How do I make this person more strategic?” It was, “How do I understand how this person naturally thinks, use that strength well, and help them expand their range from there?” That is a very different leadership challenge.
Execution Mode Is Not Necessarily A Problem
You probably know the manager I am talking about. Give them a target and a due date, and the work gets done. It is right. It is on time. They keep people moving, follow up on details, solve immediate problems, and rarely need to be reminded twice.
Then the conversation changes.
You ask, “Where do you think we need to be two years from now?” Or, “What are we missing?” Or, “If we did not have to do it this way, what would you change?” Suddenly, the person who was decisive five minutes ago gets quieter. That can be frustrating when you need your management layer to contribute at a higher level. But be careful not to immediately label the person “too tactical.”
Rich Horwath, who has worked with thousands of leaders on strategic thinking, makes this point in Harvard Business Review. He writes that many promising leaders are “unfairly branded with the ‘tactical, not strategic’ label.” The distinction is often based more on perception than on a clear understanding of how someone actually thinks.
Execution is not the absence of leadership. In the right role and at the right moment, it is an enormous leadership asset. The problem comes when we assume every strong manager should naturally excel at every kind of thinking.
Your Managers Do Not All Need To Think Like You
A few years ago, we conducted an assessment with our leadership team that examined six categories of thinking. It showed where each leader was strongest, where they were capable, and where they were comparatively weaker. When I saw the results, two people immediately caught my attention. They had the lowest scores on strategic thinking.
My first reaction was distress.
How could I have promoted these people to positions with so much responsibility when they had this kind of gap in their skill set? Then I looked at who I was actually talking about. These were two extremely strong players. Give either of them something with a deadline, and it was done. Always right. Always on time. They were outstanding executors.
That changed how I saw the assessment.
Instead of asking why they were not more like my strategic thinkers, I started thinking about the team as a whole. I could lean into people who naturally enjoyed looking at possibilities, considering alternatives, and thinking further ahead. Once we made the strategic decision, I could hand the baton to the executors. They could turn that decision into clear targets, resources, responsibilities, and deadlines.
At first, I thought I had found a way to compensate for different skill sets. Over time, I realized there was nothing to compensate for. This was how I should have thought about designing the team in the first place.
Strategic Thinking Is A Set Of Skills, Not a Personality Type
None of this means you should give up on helping managers become more strategic. It means you need to get more precise about what you are trying to develop. “Think more strategically” is lousy coaching because it does not give someone much to work with. Strategic thinking involves observable behaviors that can be practiced.
Research published in Harvard Business Review identified six capabilities associated with strategic leadership: the ability to “anticipate, challenge, interpret, decide, align, and learn.” Those are much more useful development targets than simply telling someone to “think bigger.”
A manager can learn to ask what might happen next before acting. They can practice looking for patterns instead of treating every problem as an isolated event. They can challenge an assumption that has quietly become “the way we do things.” They can consider how a decision in their department affects another part of the business. Those behaviors can be developed. They also require something many managers have very little of: room to think.
If you have spent years rewarding someone primarily for how quickly and reliably they execute, do not be surprised when execution becomes their default. If every conversation with their leader is about today’s numbers, this week’s deadline, and the next item on the list, you are reinforcing the very behavior you now want them to move beyond.
Do Not Tell Them To Be Strategic. Coach Them Into It.
This is where being more coach-like becomes important. If a manager brings you an issue and you immediately tell them what you see, what it means, and what they should do, you may solve today’s problem. But you have done most of the thinking for them. Instead, stay curious a little longer.
What are you noticing? What do you think is causing it? Where else might this have an impact? What happens if we do nothing? What options have we not considered? What assumptions are we making? What would you recommend if the decision were entirely yours?
You are still holding the goal. You are still accountable for the outcome. But rather than supplying all the thinking, you are giving the manager a chance to exercise their own judgment. That matters because strategic thinking is developed through use, not through instruction alone.
Nina Bowman makes a similar point in Harvard Business Review, arguing that strategic thinking “can, and must, happen at every level of the organization.” She recommends building a stronger understanding of the business context, looking for trends, making connections across the organization, and deliberately creating space to reflect.
Coaching gives managers a place to practice those behaviors before the stakes get higher. And there is a broader payoff to developing managers through coaching. McKinsey research found that 68% of respondents agreed that ongoing coaching and feedback conversations positively affect individual performance.
The keyword is ongoing.
One strategic planning retreat is not going to turn a strong executor into a broader thinker. Repeated opportunities to wrestle with questions, make recommendations, explain their reasoning, see consequences, and learn from the outcome can expand their capacity over time.
Start With Their Thinking Gifts
There is one more caution here. Do not make strategic thinking the new gold standard that everybody one your team has to maximize. Your strategic thinkers may come alive when they explore possibilities, challenge assumptions, and imagine what could be next. Hand them the detailed task list required to make that vision happen, and some of them will find it considerably less exciting.
Your executors may be exactly the opposite. Give them the finalized decision, the target date, the resources, and the responsibility, and watch them make magic happen. Neither is inherently better. You need both. So if you are asking, “How do I get my managers to think differently?” start somewhere else.
Learn how they already think.
Figure out where their thinking gifts are strongest. Give them work that allows those strengths to matter. Then coach them to stretch into the areas where a greater range will make them more effective. The goal is not to create a management team full of people who think exactly like you. It is to build a team whose different ways of thinking make the whole organization better.
