The Art of Doing Technical Program Management

The Art of Doing Technical Program Management

šŸ” How TPMs Can AI - Preparing for Complicated Discussions and Meetings

Practical AI for Technical Program Managers. A series of real-world scenarios showing how TPMs can use AI tools to solve common challenges, work smarter, and 10x their impact.

Aadil Maan
Sep 16, 2025
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Hi, I am Aadil and I write this newsletter on the art of doing technical program management. You are reading a premium post for my paid subscribers.

Practical AI for Technical Program Managers. A series of real-world scenarios showing how TPMs can use AI tools to solve common challenges, work smarter, and 10x their impact, complete with ready-to-use prompts and actionable strategies.

If you have Feedback and/or Suggestions to improve this guide, please leave a comment. Only paid subscribers who have access to the guide can leave comments.

OR reach out to me for any questions - aadilmaan at gmail.com.


My Dearest Readers - At the beginning of 2025, I made a re-commitment to my writing after almost 1 year hiatus during 2024. So far, your response has been overwhelming. I feel like 2025 and beyond is going to be both terrifying and exciting.

As we hit the official mid-point of 2025, please help fill out this feedback survey so I can continue to focus on delivering real world practical solutions, advice and insights to help you grow as a TPM.

Fill Out Feedback Survey šŸ™šŸ½

Now, on to this week’s post…


How TPMs Can Use AI

You’re reading another post in my ongoing series, ā€œHow TPMs Can AI,ā€ where I share real world scenarios showing how AI can make Technical Program Managers more productive and effective.

Nothing beats concrete, real-world examples. My hope is that these stories inspire you to find your own ways to leverage AI, maybe even 10x your impact, effectiveness, and focus.

How This Series Works

  • I’ll start with a common challenge TPMs face.

  • Then, I’ll show how AI tools can help you explore possible solutions, sometimes ones you might not have considered before.


The Scenario

You’ve launched a feature. It shipped, but the path there was rocky. Now your VP of Engineering wants you to lead a retrospective.

Or maybe you’re heading into a feature review where you need to ask for more time because of unexpected scope creep.

Or perhaps you’re facing a difficult conversation about someone’s behavior.

Or you will be facilitating an estimation workshop with a group of cross-functional engineering, product, design teams.

As TPMs, we walk into many kinds of conversations on daily basis, formal and informal. But none can feel more daunting than the ones with big audiences and high stakes.

Why so challenging? Because we often lead these meetings. There’s pressure from all sides:

  • Say too little, and you lose control of the room.

  • Say too much, and you risk derailing the discussion.

  • Say the wrong thing, and you could damage trust.

How do you keep the meeting on track when your VP starts to digress? How do you lead if you’re naturally introverted? How do you handle tough conversations without freezing up?


Before AI

Over time, experience helps. You reflect on past situations, learn what worked, and build your own playbook.

You might try to anticipate where things could go wrong, prepare pre-reads, or ask your manager and cross-functional partners for advice. But no matter how much you plan, the first unexpected moment can throw everything off.

When you’re still junior, you might even piece together advice from blogs and articles about running effective meetings. That’s useful but often not enough to prepare for the real pressure of the room.

You always need something to calm the nerves.


After AI

Here’s where AI changes the game.

The real power of AI isn’t just access to information but it’s the ability to get coaching that’s tailored to your exact situation. With the right prompt, AI can help you prepare in a way that feels actionable and relevant to you.

Recently, I had to lead a retrospective. I’ve done plenty of these in my career, but even with experience, it helps to refresh and rethink how to approach them.

So I leaned on AI. I wrote a prompt that laid out my context and asked for strategies, facilitation tips, and sample ways to phrase things during the discussion. The output gave me not just a refresher but also new angles to consider.

And this approach isn’t limited to retrospectives. You can apply it to any big or complicated meeting like feature reviews, roadmap debates, or difficult one-on-ones.

The Prompt

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