A love letter to project managers who overthink everything

There was a project I knew wasn’t going to work within the first two weeks.

Every call revealed the same pattern. The client team wasn’t aligned internally about what the project actually was. Roles were fuzzy. Decisions shifted depending on who joined the Zoom. We would try to move the work forward and find ourselves blocked by conversations they hadn’t had with each other.

There was also a quiet expectation that, as the project manager, I would step in and manage their internal dynamics for them. They expected me to track down their stakeholders, schedule calls, align their leadership, consolidate feedback that contradicted itself, etc. Those things absolutely needed to happen. They just weren’t mine to own.

I wasn't the only one on my team seeing this. Everyone felt it to their core. We flagged what we could early. We asked clarifying questions. We tried to anchor roles and expectations. Still, after every meeting, I would sit for a moment staring at the “Leave Meeting” button, thinking we accomplished nothing again.

My team was focused on delivering excellent work, which they did. Even with making progress and delivering solid work, we were all watching the fault lines.

Over the course of a couple of rough weeks, the tone shifted. Frustration hardened into hostility. Energy drained from the calls. I got to a point where I realized I didn’t even want to keep doing the work, not because the work itself was bad, but because the environment around it made success nearly impossible.

We had the hard conversation. The contract ended. Everyone moved on.

When I looked back, the red flags had been there from the start. They showed up in the sales process. They showed up in how decisions were avoided. They showed up in the resistance to accountability.

And I had seen them.

I know Valentine's Day has passed, but I’ve never been one for strict deadlines when it comes to appreciation. On to the letter...

Dear project manager who replays meetings in your head,

When you’ve worked across enough teams and organizations, you begin to recognize patterns. You notice when a project is being used to solve a problem it cannot actually fix. You notice when a client is asking for deliverables but actually needs alignment. You notice when roles are undefined in ways that will eventually create friction.

From the outside, that awareness can look like overthinking. From the inside, it feels like driving a car, orchestrating a symphony, and playing a game of whack-a-mole all at once.

Part of our job is to anticipate where things will break. We are supposed to examine whether the structure can support the ambition. We are supposed to ask the uncomfortable question before it becomes an expensive one. We are supposed to consider the personalities, the politics, the ownership gaps, and the cultural friction that never show up in a project plan.

Sometimes you surface the risk early and the team adjusts. Those are the quiet wins no one celebrates because the disaster never happens.

Other times, you soften your read because you want the partnership to work. You assume the tension is temporary. You tell yourself that with enough patience and process, alignment will eventually emerge. Experience teaches you that structure cannot compensate for a missing foundation.

There is a difference between spiraling and sensing. Spiraling is circular and untethered. Sensing is grounded in history, pattern recognition, and evidence you’ve collected over years of work. The longer you do this job, the more clearly you can tell the difference.

You will not always be right. I have misread situations, overanalyzed tone, and occasionally mistaken caffeine for intuition. I'll probably do those things again, and that's okay! But I know from experience, more often than not, when something felt structurally off, it was.

If you leave meetings with a subtle sense that something isn’t aligned, there is a good chance you are picking up on signals others have not yet processed. That awareness is part of what makes you effective.

It can feel lonely to be the one asking harder questions while everyone else is bursting with creating energy, eager to move forward. It can feel heavy to carry foresight when the room prefers momentum. Still, projects that succeed over the long term usually have someone willing to pause and examine the cracks before they widen.

If you have ever replayed a meeting because you sensed misalignment, or questioned a scope because the ownership didn’t add up, or flagged a personality dynamic that later became a full-blown issue, you are not being dramatic. You are a good project manager.

You are protecting the work, protecting the people doing the work, and protecting the future version of the project that has not yet gone sideways.

That kind of attention deserves acknowledgment. So consider this your slightly belated Valentine.

With appreciation,
Brett

TL;DR

If you notice red flags early, question unclear roles, and sense misalignment before others name it, you are not overthinking. You are doing preventative leadership. The real skill is learning when to push, when to document, and when to walk away.