Management

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

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I was coaching a new team lead at a startup yesterday, and he brought up a challenge I think probably affects many teams: how do you deal with being blocked waiting for a decision about day-to-day work from the person you report to?

This happens because nobody likes being negatively surprised. Especially in a startup that is going through many growing pains, there are many fears, not the least of which is the fear of losing control.

(Control itself is an illusion, but that’s a separate topic.)

These managers want to be in the loop and know what’s going on. What they’re afraid of is things going sideways and getting blindsided, when they could’ve prevented it somehow.

This is a reasonable concern. Senior leaders in any org have a different perspective than other people, because they are seeing everything. They can often spot problems from their perspective that someone directly involved with the work can’t. These are often integration problems or long-range implications that aren’t obvious in the moment.

Usually, these people don’t have all the information needed anyway and are ultimately going to push the decision back to the people closest to the work involved.

They just want to be in the loop, know what’s happening, and be able to contribute thinking and guidance if they see something that isn’t working or if they have a different perspective from their vantage point.

The problem is that such well-intentioned practices lead to a bad place: bottleneck.

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