Hey Subscriber First Name,

A few things in this one. A lesson I learned about handling difficult stakeholders, a tip that will change how you use AI as a PM, and a free cheatsheet at the end that turns any AI tool into your senior PM advisor.

I used to watch a project manager get into the same argument every week. Different meeting. Different topic. Same result. They'd make their point, the other side would push back, and within minutes they were deadlocked.

Then I watched a project director handle the exact same stakeholder. Same difficult personality. Same tendency to push back. Same room. But they walked through the conversation like it was nothing.

The difference? They never disagreed first.

When the stakeholder challenged the proposal, they didn't defend it. They didn't dig in. They said: "We're both trying to protect the deadline here. I hear your concern about the risk. What if we tried this approach, what would you need to see for it to work?"

Ten minutes later, they'd agreed a way forward.

I've thought about that moment a lot since. And here's what I've realised.

In every difficult conversation, there's a door between you and the other person. Behind it is the place you're both trying to reach. Agreement. Progress. A decision that sticks. When you lead with agreement, the door stays open. When you lead with disagreement, it closes. And every time you push against a closed door, the locks get tighter.

I've spent 15 years in rooms where people disagreed for a living. Programme boards, design reviews, stakeholder workshops. The ones that went well almost always had the same pattern: someone found common ground before they made their case. The ones that went badly? Someone tried to win the argument. And even when they were right, they lost the room.

No one teaches you this in the textbooks. But in my experience, it doubles your chances of a successful outcome with challenging stakeholders. And not just at work. This works everywhere. Difficult conversations with family. Negotiations. Any situation where two people see things differently. The principle is the same: never disagree first.

Steven Bartlett talks about this in The Diary of a CEO. It's one of his laws. And it stuck with me because I'd already been doing it without realising. The moment I heard it framed that way, everything clicked. It gave a name to something I'd learned the hard way over 15 years of delivery.

The OPEN Framework: How to Keep the Door Open

I've broken this down into four steps you can remember and apply straight away. I call it OPEN, because that's what it does.

O, Open with what you both want. Before you make your point, remind everyone what you're both trying to achieve. "We all want this to land on time and within budget" is a sentence that costs nothing but changes the temperature of the room. Start with the shared destination and you start on the same side.

P, Pause and acknowledge their point. When someone pushes back, your instinct is to counter. Resist it. Say "I hear that" or "That's a fair concern" first. You're not agreeing with their position. You're telling them they've been heard. And people who feel heard stop fighting.

E, Explore with questions, not statements. "What would you need to see for this to work?" puts the other person in problem-solving mode instead of defensive mode. It shifts the dynamic from "me vs you" to "us vs the problem." Questions open doors. Statements close them.

N, Navigate with suggestions, not demands. "What if we tried..." lands differently to "We need to...". One invites dialogue. The other invites resistance. The best PMs I've worked with frame everything as an option, even when they know exactly what needs to happen.

OPEN works in a boardroom. It works in a one-to-one. It works at home. Wherever there's a closed door, these four steps give you the key.

If you've been trying to break down doors, try never disagreeing first. Try OPEN. It might change more than your stakeholder relationships.

MAKING IT HAPPEN: Your Weekly Strategy

Pick one conversation this week where you know you're going to disagree with someone. Before you go in, write down two things: the outcome you both want, and one thing you genuinely agree with from their perspective. Open the conversation with those two things before you say anything else. Watch what happens to the tone. You're not being soft. You're being strategic. The best negotiators in the world don't start with what they want. They start with what the other person needs to hear. Try it once. If it works, you'll never go back to leading with disagreement.

AI for PMs: The One Tip That Changes Everything

Last week I introduced the five layers of AI. Most of you will already be familiar with Layer 1, the LLMs. ChatGPT, Claude, Gemini, Copilot. You ask, they answer. But here's what I've noticed. Most people get average results from these tools. They type a vague question, get a vague answer, and walk away thinking AI is overrated.

The difference between average output and genuinely useful output comes down to one thing: how you ask. It's called outcome-based prompting. Instead of pushing a loose question at the tool, you structure your input so the output is usable first time. I've been applying this to project management and the results are night and day.

Here's the framework. Six steps.

1. Give it a role. Tell it who to be. A delivery lead, a PMO analyst, a team coach. This sets the lens it thinks through.

2. Give a clear command. Use a verb and the outcome you need. Review. Classify. Draft. Identify. Not "help me with my project."

3. Set constraints. Word count, tone, governance standards, what to avoid. Constraints sharpen the output.

4. Provide context. Share the background you'd give a real colleague. Project type, team size, stage, pressures. The more context, the better the response.

5. Specify the format. Table, bullet points, structured sections. This gets you usable output first time, not an essay you have to reformat.

6. Add a human touch. Sense-check, adjust tone, add your judgement. It's your project. The AI gives you the raw material. You make it real.

Here's what that looks like in practice: "Act as a senior project manager. Review this brief and create a clear project definition: problem statement, strategic alignment, benefits, assumptions, and scope. Context: a rail infrastructure organisation at gateway approval stage. Present as: Section / Summary. Include key questions to answer before approval."

Same tool. Completely different output. All because of how you asked.

I wrote a full breakdown of how AI fits into project management on the blog. And I've created a cheatsheet with 8 ready-made prompts that turn any LLM into your senior PM advisor. Project scoping, delivery planning, stakeholder mapping, risk reviews, and more. Each one follows the framework above. You can download it here. Save it, share it, and let me know what prompts you'd want next.

If you want the full details on how I use these prompts, I broke it all down in this LinkedIn post.

If this landed with you, forward it to a colleague who's dealing with a difficult stakeholder right now. That's how this community grows. One conversation at a time. Explore more insights and interactive experiences at bilaljamil.com.

Take care and speak soon, 

Bilal