The best leaders today don’t boss. They coach. And yet, when things get hectic—tight deadlines, shifting priorities, delivery pressure—it’s all too easy to default to directing rather than developing. To assign rather than align. To fix rather than grow.

But that approach drains your energy and your team’s autonomy. You end up thinking for others, solving their problems, and carrying the burden of every decision. 

If the thoughts below resonate with you, then it’s probably time to change the conversation.

• “Why don’t they just take ownership?”
• “Why do I have to keep reminding them?”
• “Why can’t they solve this without me?”

Coaching conversations are different. They create space for reflection, ownership, and growth. They teach your team how to think, not just what to do. Over time, this reduces dependency, builds confidence, and strengthens your product culture.

• Instead of directing, you ask.
• Instead of reacting, you reflect.
• Instead of solving, you support the solving.

 

Most managers don’t boss because they want control—they boss because they feel responsible.

But without a strong conversational toolkit, it’s hard to step back without dropping the ball.

Common challenges include:

• Feeling like coaching takes too long in the moment
• Uncertainty about what to ask (or how to push without overstepping)
• Worrying that things won’t get done unless you dictate.

 

But here’s the paradox: Coaching may take longer up front, but it builds the capability that saves you time in the long run.

The following questions are designed to shift your mindset from solving to developing and to help your PMs build product thinking, confidence, and clarity.

 

Question 1: What’s on your mind?

Start open. Invite focus.

This disarms the transactional tone of check-ins. It invites your PM to name the thing they’re carrying — even if it’s uncomfortable. It tells them: “This space is for you.”

Use it in retros, 1:1s, or when they seem off but haven’t said why.

 

Question 2. And what else?

The magic question.

It’s rarely the first thing that’s the real thing. “And what else?” creates space for deeper thinking and less filtered responses.

Use it when discussing blockers, roadmap trade-offs, or team tensions.

 

Question 3. What’s the real challenge here for you?

Clarify the core issue.

This is the unlock question. Maybe the challenge isn’t the process — it’s their confidence. Maybe it’s not stakeholder X — it’s the fear of being wrong.

Use it when PMs spiral in complexity or seem stuck in a swirl.

 

Question 4. What do you want?

Help them name their need.

This builds self-awareness. Do they want clarity, support, space, or backup? Asking helps them reflect — and teaches them to ask for what matters.

Use it when emotions are high or alignment is unclear.

 

Question 5. How can I help?

Avoid rescuing. Offer clarity.

This question avoids assumptions. It invites your PM to reflect on what support looks like. Maybe it’s a sounding board — not a solution.

Use it to check your helper instinct and let them lead.

 

Question 6. If you’re saying yes to this, what are you saying no to?

Build prioritisation muscles.

Saying yes to a big new initiative? Then what drops? This question is gold for PMs who are overwhelmed or overcommitted.

Use it in planning, scope discussions, or career goal-setting.

 

Question 7. What was most useful for you in this conversation?

Close with reflection.

This reinforces learning and helps your PM identify what shifted. It also trains you to be a better coach — you’ll learn what lands and what doesn’t.

Use it to finish 1:1s, coaching chats, or feedback sessions.

 

Coaching in Action: A Quick Scenario

PM says: “The engineers keep pushing back on this story — I’m not sure how to move forward.”
Old boss habit: “Tell them to build it anyway.”
Coaching leader habit:

• “What’s on your mind?”
• “And what else?”
• “What’s the real challenge here for you?”
• “What do you want?”
• “How can I help?”

 

Instead of fixing, you’re developing judgment, empathy, and communication skills, you will find the root of the problem and how to progress from there to best support the PM and the Developers. That’s a win you can’t roadmap.

 

Watch the Type of Conversation, Too

As Charles Duhigg (in Supercommunicators) explains, mismatched conversation types can cause friction.

Are they asking for:

• Practical advice?
• Emotional support?
• Social connection?

 

As a coaching leader, your job is to match the moment. If they’re venting, don’t leap into “solutions mode.” Start with “What’s the real challenge here for you?” and see what emerges.

 

The Shift That Changes Everything

Being a boss gives you control.
Being a coach gives you leverage.

You stop being the bottleneck.
You become the multiplier.

With coaching conversations, you don’t just ship better products — you build better product people.

 

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📚 Further Reading

• The Coaching Habit – Michael Bungay Stanier
• The Six Conversations of a Brilliant Manager – Alan J. Sears
• Supercommunicators – Charles Duhigg