Hey Reader,

A few years back, I was working with a CFO, and early on in the project, things were looking rocky. Each time we met with him, he’d seem unsatisfied even though we were doing good work. None of us could figure out what we were getting wrong.

There was one weekend when I couldn’t let it go. I was the lead on that project, so it was on me to understand why he was so frustrated with us. When I thought about it more, I realized that the work itself wasn’t the issue. How we communicated it was.

We were giving him the strategic overview and a clean summary of where things stood. We assumed that’s what he would want. In our minds, someone in his role cared about strategy and direction, not line-by-line thinking. I had never stopped to question whether that’s how he actually worked.

When I came to that realization, the answer was obvious: He wanted to know the details before he could get on board.

He didn’t need to go through every line of a project plan in our meetings, but he needed to know that level of detail existed before he could trust the bigger picture on top of it. The next time we met, I brought the full spreadsheet. Every task, every dependency, every date. He was visibly more comfortable. The work was exactly the same. The only thing that changed was how we showed it to him.

Most of us have experienced the other side of this. We’ve worked for leaders who weren’t doing anything wrong, but their approach didn’t fully match how we worked best. We still delivered good work. The relationship remained professional and polite. And still, something felt slightly off.

We’re usually told the same thing in those situations: adapt, be professional, set aside your differences. So when we gain more seniority and freedom to lean more into our own instincts, we can forget about how it might impact who we work with. And we can end up in a few situations where we’re scratching our heads wondering why we’re struggling to get work done.

We’re rarely taught how to adapt to how other people work. And it’s even harder to do that while still keeping our own individuality.

Everyone is going to bring different tendencies into how they work. Some team members come alive at the beginning of something new, energized by what it could become. Others work best when there’s a clear process and a defined finish line. Some need to account for what could go wrong before they can commit to moving forward. And still others are the ones holding the team together, reading the room, and making sure communication stays intact when pressure builds.

None of those tendencies are better than the others. When everyone works to their strengths, we can cover each other’s gaps. The problems emerge when we believe our way of working is the only one. That assumption can get in the way of truly understanding a team member and how they work best. If a colleague seems resistant, disengaged, or hard to read, it’s worth asking whether you’re meeting them where they are and communicating in a way that works for them.

You can categorize people in a hundred different ways to figure out how they work best, but that’s only really the beginning of understanding them. Pay attention to how someone responds under pressure, what they need before they can feel settled in a new situation, and how they communicate when something isn’t working.

If you want a practical starting point for thinking about the different working styles on your team, I put together a resource that breaks it down. You can find it here.

Is there a working relationship that this made you think about?

Hit reply and let me know. I read every message.