The Art of Doing Technical Program Management

The Art of Doing Technical Program Management

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The Art of Doing Technical Program Management
The Art of Doing Technical Program Management
🔐 How TPMs Can AI - Dealing with Difficult Engineers and Leaders

🔐 How TPMs Can AI - Dealing with Difficult Engineers and Leaders

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
Aug 09, 2025
∙ Paid
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The Art of Doing Technical Program Management
The Art of Doing Technical Program Management
🔐 How TPMs Can AI - Dealing with Difficult Engineers and Leaders
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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.


How TPMs Can Use AI

I’m kicking off a new series of newsletter posts to help TPMs build their own personal AI playbook by showcasing real-world scenarios where AI can boost productivity and effectiveness.

Nothing beats practical examples of what’s possible. My hope is that these stories will spark ideas and inspire you to explore new ways to 10x your impact with AI.


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.

We’re starting this series with a classic: Dealing with difficult engineering partners or managers.


The Scenario

We’ve all been there. You’re working with an engineering manager who doesn’t believe TPMs add much value beyond:

  • Taking meeting notes

  • Asking for dates and timelines

  • Sending “annoying” status reports

They’re convinced that the only real work is writing code, and that anything else is “fake accountability” or unnecessary process.

Sorry if this brings back bad memories; it’s a situation many of us have faced, or will at some point. And often, your own manager will ask you to “bridge the gap” and make the relationship work.


Before AI

In the past, you might have:

  • Asked others in the org how they manage to work with this person

  • Tried to piece together a plan from second-hand stories

  • Struggled if you were a junior TPM still building influence-without-authority skills

Unless your manager was dealing with the same issue with the EM, you’d be left describing what happened (or didn’t happen) which doesn’t always lead to actionable guidance for what to try next.


After AI

What you’re looking for here isn’t a direct answer, but it’s advice and strategies.

Here’s how you can approach differently with AI:

  • My tool of choice: ChatGPT or Claude

  • My goal: Get a range of possible ways to approach the situation, tailored to my style and context

  • My method: Craft a prompt that clearly explains the situation and the outcome I’m aiming for.

The Prompt

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