I had lunch recently with a PM named Mark. Mark was feeling nervous. The next day, he was flying to a big stakeholder meeting and needed to give an update on the state of a big project he’s leading. Things had not been going that well. Mark didn’t feel confident in the technical feasibility of what his team was working on.

He said to me:

I want to be honest with them about what isn’t working, but I’m afraid they’ll freak out. I’m not confident in our approach either. How do I tell them the truth but not spook them?

It’s inevitable to be in this place. Especially if you value transparency and intellectual honesty. So what’s an intellectually-honest-wanting-to-inspire-confidence-but-not-feeling-too-confident PM to do?

Good news: there is a simple, three-question framework that will help you feel more confident going into any such conversation,

The three questions in the background

Try to go into any stakeholder conversation having an answer to the following three questions—especially when things are going sideways:

1. what’s happened?

2. what’s it mean?

3. what's next?

You may not explicitly say these to your stakeholder, but the thinking and information contained in each are essential. I’ve found that it’s more about having an answer to all three questions than having the perfect answer to any subset.

First: What’s happened?

Most of the time, you and your stakeholders have a completely different experience of time as it relates to your project. This is because the current context of the project is always shifting.

You are in this thing constantly. Your stakeholders are checking in occasionally.

The pace of change you each experience is totally different. They get out of date quickly, and each time you sync, you need to catch them up to the current context.

Whenever you sync up with a stakeholder, ask: what’s happened since I last updated this person?

Second: What’s it mean?

The next question you need to answer is: what does it mean?

Even once they are caught up, your stakeholder doesn’t have your full context. They may very well not know how to think about what you’ve told them. So think through how you want them to think about this, and how to frame things for them.

Based on what has happened: why does that matter? what does that mean? How should they think about it? Is it good or bad? What are the implications, or second-order effects of what has happened?

Third: What’s next?

This is the inevitable last question: okay, now what? Based on all that...what’s next?

You may not feel confident about your next step. That’s okay.

But have an intended next step, your current best answer, and be ready to discuss it.

This will give your stakeholder the chance to contribute to you and the project by helping you think through your decision. You can always change your mind, but by giving the stakeholder a clear intention to respond to, they can give you more useful feedback than if you go into the conversation nebulous.

Feel more confident in the chaos

As you can see, these three questions are a simple framework to help you prep for key stakeholder meetings. With the above three questions thought out, you can feel more confident navigating the discomfort of having difficult conversations with stakeholders. You can be intellectually honest and give partners or stakeholders tough news, help them see the path ahead, and generally be OK with it.

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