Coaching, Listening, and Problem Solving
There are only three modes in a leader/report 1:1 session: coach, listen, or problem-solve, and while you might love to problem-solve, CEO/Leader problem-solving is a poor use of limited bandwidth; it feels productive but erodes development. Coaching drives better outcomes than problem-solving as it's scalable, requires the executive to think through what they are trying to figure out, and imparts the ownership that comes with agency.¹
Below are 10 coaching questions designed to prompt executives to think about the issues they are elevating in ways that drive them to be strategic and thoughtful. They also remove the “solve the problem” reflex from the interaction. Most, if not all of these questions, may be preceded by a very tight reflection of their statement to ensure you are listening and understanding well, and a validation such as:
“I’m hearing that you are having issues with [name issue]. Thanks for sharing that with me. I know that can be [challenging] [hard] [frustrating].”
Then pivot to one of the following, or make up your own! Remember, your job in these moments is to tolerate the discomfort of not fixing the problem for them. It might feel slower today, but it's setting the stage for a faster, scalable tomorrow.
“What’s the outcome you’re trying to achieve here, and how will you know you achieved it?”
A. Forces clarity. Some executives jump to tactics; this pulls them back to first principles.“What assumptions are you making?”
A. Then move to another of these questions.
“If you were advising a peer on this issue, what would your advice be?”
A. Creates cognitive distance.“What’s the smallest actionable experiment you could run this week to test your thinking?”
A. Encourages learning and avoids analysis paralysis.“Who else needs to be part of the solution, and why?”
A. Exec-level work is cross-functional by definition. This avoids silos.i. Follow-up Q: “How will you cross-functionally navigate this?”
“What are you optimizing for in your decision, and what tradeoffs are you choosing?”
A. There are always tradeoffs. If they can’t articulate the tradeoffs, they’re not making a strategic decision.“Where does this sit on the spectrum of urgent vs. important?”
A. People conflate the two. The Eisenhower Matrix is still relevant.“What’s the conversation you’ve been avoiding that would unlock this issue?”
A. Conflict: Almost every executive problem is a people problem in disguise.“What’s one thing you learned from this that you want to apply in the future?”
A. Drives learning rather than episodic, one-off fixes.“What support do you need from me — and what should not be mine to solve?”
A. Sets boundaries and reinforces ownership. CEOs who skip this create dependency loops.
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¹ That said, when someone comes to you to ask “how much chocolate should we feed to the cows to get chocolate milk”, this is the time for problem solving, not coaching. Sometimes, a quick problem solve is the answer.
