Are you developing your team’s thinking? Or merely harvesting it?
Many leaders ask for better thinking while doing little to build it.
This article is the fifth in a six-part series, Building Strategic Capacity in Your Leadership Team, exploring how CEOs help operational leaders develop the judgment, perspective, and tradeoff thinking required to contribute meaningfully to strategy rather than simply execute it. Read the first article here.
THINK ON IT: Are you developing your team’s thinking? Or merely harvesting it?
Early in my career, I worked for a former military officer.
He was sharp, experienced, and confident in his judgment. He came from an environment where decisions moved fast, authority was clear, and execution mattered. Over time, his staff had learned to operate accordingly. They anticipated what he wanted, framed updates to match his instincts, and became efficient at giving him what he expected.
I didn’t know that when I arrived, so I did what came naturally. I asked questions, challenged assumptions, and engaged the thinking behind the direction rather than simply accepting it.
One afternoon, we got into a lengthy debate in his office over a path we should take. After more than two hours of disagreement, he smiled and said, “I rather enjoyed that.”
“I’m glad one of us did,” I responded.
What stayed with me was not the disagreement itself, but what his comment revealed. He had enjoyed it because it was rare. Not because his team lacked intelligence or opinions, but because somewhere along the way they had learned that the safest move was to align, not to challenge. They had stopped bringing him their thinking and started bringing him his thinking, reflected back and polished for approval.
That dynamic is more common than many leaders realize.
You don’t have to be authoritarian to create it. You just have to be predictable enough, confident enough, or decisive enough that people conclude thinking out loud carries more risk than it is worth. When that happens, meetings can look strategic without actually being strategic. The room is engaged. People contribute. But much of it is performance, not thinking.
If you ask poor questions, rather than rich ones, you train leaders to answer quickly rather than to think deeply.
AI can reinforce the same habit. It can produce fast answers instantly, and many will be useful. But fast answers are not the same as good judgment. Strong decisions still require context, tradeoffs, and lived experience.
Many CEOs say they want more strategic thinking from their teams, but they may be inadvertently training the opposite. Most leaders are simply doing what the pace of business has trained them to do. They ask for updates, recommendations, ownership, and timelines. Those are useful questions, but they mostly develop responsiveness, not judgment.
A leadership team can become very good at producing answers without becoming very good at thinking. In that kind of environment, leaders are harvesting whatever thinking already exists rather than developing more of it.
When leaders learn to answer quickly rather than think deeply, assumptions go unchallenged, tradeoffs go unexplored, and conversations get shorter while thinking gets thinner.
Strategic thinking requires something different. Leaders must wrestle with ambiguity long enough to interpret what they are seeing. They need questions that widen perspective rather than narrow it too quickly. They also need an environment where thoughtful challenge is not mistaken for disloyalty.
This is why the quality of strategic thinking on a team often reflects the quality of questions the CEO asks. If your questions are mostly operational, you will get operational thinking. If your questions reward speed, you will get fast answers. If your questions imply the right answer is already known, your leaders will spend more time reading you than thinking for themselves.
Which raises an uncomfortable but important question: When your team gives shallow answers, is it because they lack the ability to think more strategically? Or because they have quietly learned that careful is safer than thoughtful?
Your team is always learning from how you lead. The real question is whether you are cultivating thinkers for the future, or merely harvesting answers for today.
In the Act On It section below, I’ll share practical ways you can ask better questions, create more honest dialogue, and develop stronger thinking in your leadership team. (Premium Members only. Not a member yet? Become a Premium Member. Paid subscribers get access to over 100 tools and how-tos for implementing strategic topics, including a 7-part series to help leaders build their own strategic capacity.)
“Surround yourself with people who will tell you what you need to hear, not what you want to hear.” — Colin Powell
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