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Coaching is a distinct mode of working with people - different from managing, mentoring, or advising. Where a mentor shares their experience and an advisor gives recommendations, a coach asks questions that help the other person think more clearly and find their own way forward 🎯 The distinction matters because people act on conclusions they reach themselves more than conclusions handed to them. A coaching conversation that ends with “so what are you going to do?” produces more durable change than advice that ends with “here’s what I’d do.”

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The core skill: asking, not telling

The instinct when someone brings you a problem is to solve it. Coaching resists that instinct. Instead of “here’s what I’d do”, you ask:
  • “What have you already tried?”
  • “What options do you see?”
  • “What’s stopping you from doing X?”
  • “What would you do if you weren’t worried about Y?”
  • “What does success look like here?”
The goal is to help the person access their own thinking - which is usually better than they give themselves credit for 💡

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When to coach vs. when to advise

Coaching isn’t always the right tool. If someone is new to a role, needs specific knowledge, or is facing an urgent situation they don’t have the context to navigate alone - that’s a moment for advice or mentoring, not coaching. Coaching works best when the person has the capability to solve the problem but is stuck, uncertain, or hasn’t yet worked through all the dimensions. It’s the tool for developing independent thinking, not for transferring knowledge quickly.

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Coaching in a product context

Senior PMs and product leaders use coaching instinctively with their teams - helping them work through discovery decisions, prioritisation calls, and stakeholder challenges rather than just handing down answers. It’s also the mode managers need to shift into as their team gains experience. Eric Schmidt, Jonathan Rosenberg, and Alan Eagle’s Trillion Dollar Coach tells the story of Bill Campbell, who coached some of Silicon Valley’s most successful leaders. The throughline: the best coaching is rooted in deep care for the person, not just their performance 🙌

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The listening requirement

You can’t coach without listening. Not listening while formulating your next question - actually listening, staying curious, and following the thread the other person is pulling. Most people who think they’re coaching are actually just asking leading questions toward the answer they’ve already decided on. Lesson learned: the first time I tried to coach rather than advise, I lasted about four minutes before jumping in with my opinion. It takes real discipline to stay in question mode. It gets easier, and the results are worth it.