A leader asks a team member, “What do you think we should do?” The team member offers a recommendation. The leader follows with another question, then another, until the recommendation starts to resemble the one the leader had in mind all along. Everyone leaves with a decision, and the leader feels good about having coached rather than directed. But what did the other person actually get to practice?
Helping someone develop judgment is different from helping them arrive at yours. The difference is hard to see when your answer is reasonable and your intentions are good. If the only acceptable destination is the conclusion you already reached, the other person is practicing something else: figuring out what you want.
The Question With an Answer Key
A managing director is reviewing a project manager’s staffing plan for a new engagement. The plan keeps continuity with the client and gives a newer colleague real responsibility. The director prefers a different arrangement and asks, “What would have to be true for this to work without our most experienced person on it?”
It sounds like a coaching question, but the project manager hears a verdict. Now they have to choose between defending their reasoning and coming around. Either way, they are responding to the director’s preference rather than thinking through the problem.
The director may well be right. Experience matters, and there may be something the project manager hasn’t considered. The problem is that advice is dressed up as discovery. If the director has already decided, the more useful move is to say so and explain why. If the decision is still open, the project manager’s thinking needs a real chance to change the outcome.
Why Capable Leaders Get Caught Here
For leaders who built careers on expertise, supplying the answer feels responsible. You can see the route through the problem, the deadline is real, and you could settle it in five minutes. A few guiding questions feel like a sensible compromise.
It is also worth being clear about the satisfaction involved. Watching someone arrive at your conclusion confirms your expertise and lets you feel you gave them room to grow. You can care deeply about someone’s development and still be attached to being the one who knows. That attachment shows up when their thinking heads somewhere you wouldn’t have gone.
One test is to ask whether you could support a well-reasoned answer that differs from yours. If you couldn’t, be honest about that. People learn from clear direction. They have a much harder time learning from a decision disguised as a discovery process.
When the pattern repeats, people start preparing for your preferences instead of exercising judgment. They bring the option you’re likely to approve and wait for your reaction before committing. You may read that as a lack of initiative, but it is a reasonable adaptation to how decisions actually get made. The cost comes back to you as well. You stay central to decisions you hoped others would eventually own, and the people you meant to develop get very good at securing approval without getting any better at making the call.
Give the Thinking Somewhere to Go
Start by naming what is open: “The budget and delivery date are fixed, but I want your recommendation on staffing, and I’ll make the final call.” That gives judgment a defined space instead of asking someone to guess how much freedom they have.
Then explore their reasoning before offering yours. Ask what they’re optimizing for and what risk they think is worth taking. If you know something they don’t, say it plainly. “There’s a client commitment you may not know about” teaches more than a string of questions engineered to make them find it.
When their approach differs from yours, separate a material concern from a preference. A contractual obligation deserves intervention. An approach that simply feels unfamiliar deserves a closer look: “My instinct is to do this differently. Walk me through why yours will work.”
Finally, come back to the decision once there’s something to learn from it. Ask which assumptions held up and what they would change next time. That tells you far more about their development than whether they agreed with you.
Before your next coaching conversation, notice whether you’re willing to be surprised by where it goes. You can still advise, set limits, or make the call. But when you invite someone to think, let that thinking matter. Over time, you end up with someone whose judgment you trust on the days their answer isn’t the one you would have given.
