Two Conflicts | A Retrospective

I’ve done this wrong more times than I’ve done it right. I’ve backed down when I should have asked why. I’ve pushed back when I should have recognized I was looking at something personal, not professional. I’ve absorbed resentment for years without understanding where it came from.

What I know now, looking back at the moments that shaped how I show up in conflict, is that the diagnosis comes later. Not in the moment. In the moment, you just react. The learning happens when you’re willing to trace it back and figure out what you were actually dealing with.

The one where asking worked

A few years ago, I was managing delivery for a client whose asks were changing daily. His company had just come through an acquisition. New leadership above him, pressure to show results fast. I didn’t know any of that yet. I just knew emails were going unanswered, status updates were ignored, and we were doing the wrong work well.

I could have kept taking the new direction. I was lower on the food chain, and it would have been easier. But I’d been through enough projects to know how that ends. Six months of chasing a moving target, a half-finished deliverable, and a burnt-out team.

So I asked. Not to challenge him. Out of genuine curiosity about where we’d drifted from.

Why are we shifting this deliverable? Because leadership asked. Why did they ask? A competitor released a new feature, and we need to respond. Why do we need to respond right now? Because we can’t look irrelevant. We can’t lose business. This will look bad on me.

That last one I sat with. Would we actually be irrelevant? Or were we reacting to the optics of a competitor’s move while our clients were still counting on us to be steady?

That question reset the conversation. Not because I had a better answer, but because neither of us had asked it yet. We narrowed our focus to one feature we could deliver quickly, use to rebuild trust, and buy ourselves the runway to rethink the backlog properly. He felt heard. The project got back on track.

Looking back, this worked because the friction was actually professional. There was a real misalignment underneath the scope creep. The 5 Whys didn’t create that alignment. It just surfaced it so we could name it.

The one where asking made it worse

I had a coworker who came out of left field with snark. No warning, no context. My instinct was to disappear. Apologetic, backing down, making myself smaller to defuse the tension.

It worked, in a narrow sense. The moment passed. What it left behind was resentment.

I found out later, through a manager and mutual colleagues, that he was dealing with serious health issues and carrying stress that most people don’t bring visibly into a conference room but can’t fully leave at the door. When he was under pressure, his negativity was misplaced onto whoever was nearby.

None of that was visible to me. And even if it had been, his why wasn’t mine to ask about.

What I could do, what I eventually did, was come back. Stated my boundaries clearly. Kept the focus on the project goal. Not as a confrontation. As a reset. The boundary needed to be set, for me as much as for the work.
The thing I didn’t do, and should have done sooner, was recognize that backing down was creating a problem of its own. It wasn’t grace. It was just delayed resentment, coating itself in sympathy.

Pattern recognition in hindsight

These two stories don’t give you a decision tree. They give you what I see now that I didn’t see in the moment: most workplace conflict has a source, and the source tells you whether you can ask about it or whether you need to set a boundary and move on.

When friction is work-related, a shifting scope, a decision that doesn’t track, or a stakeholder going quiet, the source is usually findable. You can ask. The question is professional. Getting there serves the project.

When friction is personal, someone carrying something you have no visibility into, asking isn’t always available. Sometimes it makes things worse. What you can do is not internalize it, set your boundary when you need to, and stop backing down as a substitute for it.

The diagnostic question is the same in both cases: is this mine to solve, or mine to manage?

I didn’t have that question at the moment. I have it now, because I’ve lived both versions. The one where asking unlocked a conversation that needed to happen. The one where my silence was as much a problem as his sharpness.

Most conflict isn’t about you. It’s about pressure, context, and things that were in motion before you walked into the room. The instinct to ask what you did wrong is natural. Directed inward too quickly, it costs you the clarity you need for the actual problem.

The skill, it turned out, wasn’t reading the situation perfectly. It was being willing to look back at it honestly and ask: what was really going on, and what did I actually need to do?