The human side of project leadership #007

The Difficult person is a data point

There is a point in almost every project manager’s career when you realize the hardest part of the job is not the project. It’s the people.

It’s the client who questions everything. The stakeholder who waits until after the meeting to send the angry email. The teammate who seems determined to make every conversation harder than it needs to be. The person whose name pops up in Slack and immediately changes your mood.

No methodology prepares you for that. No template fixes it. And moving another task around on a project plan probably isn’t going to help either. Kelly Vega, one of this year's DPM 2026 keynotes, I was pretty stoked to sit down with her for my Human Side of Project Leadership series leading up to the Digital PM Summit.

I’ve known Kelly for a long time. We realized during our conversation that we first met more than a decade ago at a Digital PM workshop I hosted at the Basecamp office in Chicago. Since then, Kelly has built a career in project and delivery leadership, and she’s also become @nottheworstpm on TikTok, where she turns some of the absurdity of project management into painfully relatable comedy.

At this year’s Digital PM Summit, she’s presenting a session called Empathy for the Difficult Client (or Teammate). This is a topic I really enjoy (And was excited to see come through in Kelly's session proposal), so I had questions.

Frustration is information

When someone is making your life miserable, empathy is probably not the first thing that comes to mind. For that, Kelly’s first piece of advice is deceptively simple: pause.

She told me that the times she has reacted immediately to a difficult situation rarely turned out the way she wanted. Even with good intentions, reacting from frustration tends to make things messier.

Over time, she started looking at frustration differently. It’s a data point. Something is happening. Someone is worried, confused, frustrated, missing information, feeling ignored, or responding to pressure you might not even know exists.

That doesn’t excuse shitty behavior. But before you react, it’s worth figuring out where it’s coming from. There might be something going on that you can actually address.

Empathy does not mean putting up with everything

I think project managers sometimes hear “have empathy” and translate it into “put up with more.” Those are not the same thing.

Kelly described the line as the difference between empathy and over-functioning. You can try to understand where someone is coming from without taking responsibility for everything they’re feeling or doing. If the same frustration keeps coming up, something has to change.

Maybe you change the process, have a direct conversation, or escalate the issue. And sometimes, you have to recognize that you’ve done what you can and stop carrying the situation around with you.

Project managers absorb a lot

There is another reason this gets complicated for PMs: we sit in the middle of everything. Clients are stressed. Stakeholders are nervous. Designers are frustrated. Developers are overloaded. Leadership wants answers. And somehow all of that energy finds its way to the project manager.

That can be exhausting.

Kelly talked about the importance of having trusted counterparts you can go to when that happens. An account manager, creative lead, technical lead, or another PM can help you sanity-check what you’re hearing. But she made an important distinction: don’t just vent. Venting is healthy, but eventually you have to get to, “Here’s what I’m seeing, here’s what I think is happening, and here’s what I think we should do.”

That shift toward being solution-oriented can keep you from getting stuck in someone else’s frustration.

Pause. Assess. Clarify. Decide.

So...this was kinda fun. Kelly revealed in the interview that she is bringing a framework to her Summit session called PACE: Pause. Assess. Clarify. Decide.

Yes, project managers apparently require an acronym for everything. But this one works because it creates a little distance between the thing that happens and your response to it.

Pause before reacting.

Assess what is actually happening, including what you might be missing.

Clarify the issue instead of filling in the gaps yourself.

Then decide what you’re going to do.

That assessment doesn’t have to happen alone, either. Sometimes the smartest thing you can do is pull in someone who has more history with the client, knows the teammate better, or simply has enough distance from the situation to see something you can’t.

As Kelly put it during our conversation, communication is usually at the bottom of alignment problems. And sometimes the “difficult” client or teammate is actually a scared client or teammate who doesn’t have enough visibility. That doesn’t excuse bad behavior, but it might change how you approach it.

Know what is actually yours to control

Toward the end of our conversation, I asked Kelly what she hoped someone would take away from her Summit session if they walked in thinking about the one person at work who was currently making their life miserable.

Her answer was about recognizing what you can actually control. You can have the conversation, adjust how you’re working together, bring in someone else, or escalate when you need to. But you can do all of that and still end up working with someone who is difficult.

I’ve always had a hard time letting that kind of thing go, and I suspect a lot of project managers can relate. We’re invested in the work and the people doing it, so when something isn’t going well, it’s easy to take it personally or feel responsible for fixing it. Kelly’s point is that eventually you have to recognize when you’ve done what you can and stop giving the situation more energy than it deserves.

But experience teaches you that not every problem is yours.

Sometimes you have to find the humor

This is probably part of why Kelly’s @nottheworstpm videos resonate with so many people. She told me that a lot of the scenarios she turns into comedy come from past experiences. What makes creating them especially useful is seeing the response from other PMs.

She’ll post something and wonder whether it’s just her. Then the comments arrive.

The gist is, “This was me today.” or “Felt.” And girl, I gotta say, same. There’s something reassuring about realizing that the ridiculous situation you thought could only possibly be happening to you is apparently happening to project managers everywhere.

We are all out here doing this, and sometimes laughing about it is healthier than opening Slack and writing the response you actually want to send.

Project management is cumulative

One thing Kelly said reminded me of something I’ve believed for a long time: project management is an incredibly cumulative career.

The longer you work in project management, the more experience you have to draw from when something gets weird. You recognize behaviors you’ve seen before, you know when it’s worth addressing something directly, and you have a better sense of when to involve someone else or just let something go. None of that makes difficult situations easy, but experience gives you perspective. You’re less likely to react immediately or assume that someone else’s frustration is yours to fix.

Kelly Vega will be presenting Empathy for the Difficult Client (or Teammate) at the Digital PM Summit, October 19–20 in Asheville, North Carolina.

If you’ve ever had a client, stakeholder, or teammate who made you want to throw your laptop out the damn window, I have a feeling you’ll want to be in the room.

T L ; D R - Difficult people are part of project management, but empathy doesn’t mean accepting bad behavior or absorbing everyone else’s stress. Kelly Vega suggests treating frustration as information: pause, assess what’s happening, clarify the real issue, and then decide what you can actually do about it. Sometimes the most important realization is that you can control your response without being responsible for fixing the other person.