AI Driven PM: S2E9 - Coach First, PM Second

 

Or: Why the Best PMs in the AI Era Coach First and Manage Second

I almost skipped the coaching certification.

When I joined the John Maxwell team, the coaching program was part of the package. And honestly? I wasn't that interested. I was doing well in my career. I had built successful PMOs. I had a reputation for getting results.

What did I need a coaching certification for?

But I went. And a trainer named Christian Simpson changed everything.

He was talking about directive leadership—how most leaders just answer questions, tell people what to do, and keep everyone dependent on them for direction.

That was me. I was a directive leader. And I knew it, because the proof showed up every time I tried to take a vacation.

My phone would ring constantly. I'd come back to disaster areas. Everything waited for me because I had built a team that couldn't function without my answers.

I thought I was being helpful. I was actually being a bottleneck.

And then Christian said the thing that rewired how I lead:

"If you give somebody the answer, you rob them of a lifetime of learning."

That hit me.

If you give someone the answer, they'll ask the same question next time. Because they didn't learn—they were just told.

But if they find the answer? If they work through the problem, make the connections, arrive at the solution themselves?

They'll never forget it.

From Manager to Coach: The Shift That Changes Everything

There's a debate I've been in a hundred times about whether project management is "command and control."

When I went through my first Agile training, they described project management like Godzilla stomping through cities. Commanding. Controlling. Dictating.

And Agile? It was communal living, group hugs, servant leadership, butterflies everywhere.

I always pushed back on that.

I was never a command-and-control PM. Even before my personal development journey, I believed in enabling people over directing them. I just didn't have the language for it.

But here's the real distinction that matters:

Old PM role: Here's the plan. Here's your task. Go do it.

New PM role: What do you need to succeed? How can I remove the obstacles in your way?

One extracts work from people. The other builds capacity in people.

And in the AI era, that difference has never mattered more.

Here's why:

AI can automate task management. It can build schedules, generate reports, write requirements, summarize meetings. All the things that used to justify our existence as schedulers and documenters?

Gone. Or going.

But what AI cannot touch is the emotional side of project work.

Conflict between two senior engineers who both think they're right and neither is wrong.

A team member withdrawing quietly because scope keeps changing and nobody's noticing.

A junior PM who doesn't know how to push back on a sponsor without getting their head taken off.

That's where we live now. That's the new PM value zone.

And you can't navigate that by giving answers.

You navigate it by asking the right questions.

The Coaching Mindset vs. The Management Mindset

Manager	Coach
Provides the answer	Asks questions to surface the answer
Directs action	Creates space for discovery
Extracts work	Develops people
Tells people what's wrong	Helps people see what they haven't seen
Creates dependency	Builds capability

The shift isn't about being softer. It's about being smarter.

People own the solutions they create. When the answer comes from them—when they worked through it, wrestled with it, arrived at it—they execute it with conviction, not compliance.

And remember what we covered in Episode 8? Compliance leads to resistance. Resistance leads to revenge. Revenge leads to resentment.

Coaching is the antidote to all three R's.

The Core Coaching Skills Every PM Needs Right Now

Active Listening: Not just hearing words—hearing what's not being said. The fear underneath the frustration. The confusion beneath the compliance. The real blocker hiding behind "everything's fine."

Powerful Questions: Questions that help people think differently, not just answer you. "What options have you already considered?" beats "Have you tried X?" every time.

Holding Space: Creating safety for the hard conversations. Pausing. Sitting in the silence instead of rushing to fill it.

Capability Building: Developing people, not just extracting work from them. Asking "what would help you grow through this?" alongside "what do you need to ship this?"

Accountability with Empathy: High standards AND high support. Both. Not one or the other.

The Story That Made It Click

Let me tell you the best coaching moment I've ever been on the receiving end of.

I was building out the GrowthDay platform for Brendan Bouchard. And I was having a real problem with one of my team members. I was frustrated. Genuinely frustrated.

So I called Brendan.

And I went. I vented. I laid it all out—every frustration, every grievance, everything this person had done that was driving me crazy.

Brendan just listened. The whole time.

And when I was finally done, he asked me one question:

"Huh. Well, what did he say when you told him all this?"

Silence.

What did he say... when I told him.

I hadn't told him.

Not one word of what I'd just spent ten minutes telling Brendan had ever been said directly to the person I was frustrated with.

And in that moment I realized: I had been complaining to the boss about someone I hadn't even attempted to talk to myself.

Brendan didn't tell me that. He didn't say, "You need to go have that conversation." He didn't lecture me about going around someone.

He asked one question.

And I arrived at the answer myself.

That's a lifetime of learning in a single sentence.

I've never forgotten it. And I've never again brought a complaint to someone's supervisor without first having the conversation directly.

That's coaching.

Now Let's Use AI to Get Better at It

Here's the beautiful irony: The tool that people worry will replace human connection is actually one of the best tools I've ever found for preparing for human connection.

AI won't coach your team for you. But it will help you show up to coaching conversations more prepared, more thoughtful, and more focused on the right questions.

Let me show you three prompts I use.

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Prompt 1: Coaching Conversation Planner (Your Non-Negotiable)

The situation I gave it:

Sarah—a senior back-end engineer on the Social Wishing project—has been withdrawing. She used to drive planning discussions and code reviews. Now she's quiet, says "whatever the team decides," works late but doesn't surface blockers, and gives short answers in one-on-ones.

Her velocity is still fine. Her engagement is not.

What ChatGPT gave me:

"Sarah still delivers. The risk sits in disengagement—senior engineers influence architecture, team energy, and decision quality. If she withdraws, the team loses signal."

Powerful questions by theme:

• "What have the last few sprints felt like from your perspective?"
• "When scope changes come up, what goes through your mind?"
• "What are you carrying that the team doesn't see?"

Claude's opening:

"Sarah, I wanted to carve out some time that isn't about tickets or sprint status. How are you actually doing?"

And then: Full stop. Don't add qualifiers or softeners. Let her decide how much to give you.

If she says "fine" or "busy," Claude told me:

"Follow with: 'I believe that you're busy. What I'm asking is whether busy feels okay right now—or whether it's starting to wear on you.'"

That's not a script. That's a doorway.

Claude also gave me the question sequence:

1. Energy and load
2. Work experience
3. What she needs
4. What adjustment to watch for if she deflects

This took me two minutes to generate. The conversation itself might be the most important one I have this week.

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Prompt 2: Powerful Coaching Questions Library

This one builds you a reusable toolkit organized by situation type.

Common PM situations:

• Team member stuck and escalating
• Two team members in conflict
• Team member underperforming but unaware
• Team member wants career growth
• Team member resistant to change

My favorite questions from what the AI generated:

For a stuck team member:

• "If you had to make this decision without me, what would you do?"
• "What's the smallest step you could take to test a direction?"

For conflict:

• "What outcome do you actually want from this situation?"
• "What part of this disagreement is about facts versus preferences?"

For underperforming but unaware:

• "What are you most proud of from the last month—and what would you do differently?"
• "Is there anything getting in the way of your best work that I don't know about?"

The most important coaching principle the AI surfaced:

Don't lead the witness.

❌ "Don't you think we should handle the architecture this way?" ✅ "What architecture options do you see?"

❌ "Do you think it would help to talk to them directly?" ✅ "What options have you considered?"

Same destination. Completely different journey. And the journey is where the learning lives.

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Prompt 3: Conflict Coaching Facilitator

The scenario: Two senior engineers at an impasse. Sarah wants microservices from day one (scalability). Tom wants monolith first (speed to MVP). Both are dug in. The debate is getting personal.

Claude's diagnosis:

"Architecture debates between senior engineers rarely stay technical this long unless something else is driving them. This conflict has three layers: 1. Risk tolerance and time horizon 2. Identity and credibility 3. Decision authority ambiguity

Until you address layer three, layers one and two will keep feeding each other."

ChatGPT's framing:

"Sarah sees Tom as cutting corners. Tom sees Sarah as slowing the team with unnecessary complexity. Both are trying to protect the project from risk—but they can't see that in each other.

The goal of your conversation is to reframe the debate from personal positions to shared project outcomes."

Questions for Tom:

• "What risks do you see if we start with microservices?"
• "What assumptions are you making about future scale?"

Questions for Sarah:

• "What specifically makes you confident a monolith won't become a problem at scale?"
• "What's your read on where the product is heading in 18 months?"

What the AI surfaces that's most valuable:

What's not being said.

Tom isn't saying, "I'm scared we're going to miss the launch date and I'll be blamed."

Sarah isn't saying, "I've seen monoliths become nightmare refactors and I can't watch it happen again."

Those are the real conversations. And you can't get there by asking about architecture.

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Your Non-Negotiable Experiment This Week

Use the Coaching Conversation Planner to prepare for a real coaching conversation this week.

Then ask at least three coaching questions—and resist the urge to answer them yourself.

Here's what I want you to notice:

1. How does the person respond to questions versus directives?
2. Do they arrive at solutions you hadn't thought of?
3. Does coaching build capability and ownership in a way that managing doesn't?

Because here's the thing:

The tasks are getting automated. The human side of projects—the conflict, the fear, the ambiguity, the growth—that's becoming our entire job.

If you're still managing in a world that needs coaching, you're optimizing for a role that's disappearing.

But if you learn to ask the right questions?

You become the person no AI will ever replace.

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Next time: Work-Life Balance 2.0—how AI changes the always-on PM trap. Excited to share some different ways of using AI to help us become not just better PMs, but better humans.

Want these prompts ready to copy/paste? Head to PMThatWorks.com for the full library.

Now go prepare for that coaching conversation. Somebody on your team is waiting for the right question.

— Rick A. Morris

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The Prompts (Copy/Paste Ready)

Prompt 1 - Coaching Conversation Planner

You are an executive coach training project managers to coach their teams effectively.

First, ask me 4–6 questions about the team member, the situation they're facing, what I've observed, and what outcome I want from the conversation.

Then provide a coaching conversation plan answering:

1. What is the coaching goal for this conversation?
2. What powerful questions should I ask to help this person think through the situation themselves?
3. What am I listening for? (underlying concerns, assumptions, blind spots, emotions)
4. How do I balance support with accountability?
5. What's my opening? (How do I set the tone and create safety?)
6. What's my closing? (How do I ensure clarity and commitment to action?)

Team member situation: [Enter Context]

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Prompt 2 - Powerful Coaching Questions Library

You are a professional coach creating a question library for PMs to use in team conversations.

Ask me 2–3 questions about common situations I face with my team (performance issues, conflict, low morale, ambiguity, or resistance).

Then provide a library of powerful coaching questions organized by situation type answering:

1. What are 5–7 coaching questions for each situation type?
2. What is each question designed to unlock? (self-awareness, ownership, options, or commitment)
3. When should I use open-ended questions vs. more directed questions?
4. How do I avoid leading the witness and let people arrive at their own insights?

Situations I commonly face: [Enter Situations]

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Prompt 3 - Conflict Coaching Facilitator

You are a conflict resolution coach helping PMs facilitate team conflicts.

Ask me 4–5 questions about the conflict, the people involved, what each person wants, and what I've observed about the dynamic.

Then provide a facilitation strategy answering:

1. What is the underlying conflict? (goals, values, communication styles, resource scarcity, or misunderstanding)
2. How do I create a safe space for the conversation?
3. What coaching questions do I ask each person to help them articulate their perspective and needs?
4. How do I guide them toward mutual understanding—not just compromise?
5. What agreements or commitments do we need to leave the conversation with?
6. How do I follow up to ensure the conflict is resolved and not just paused?

Conflict situation: [Enter Context]