How to Work with Complicated People summary

When you think about the toughest parts of your job, chances are it’s not the tasks or the deadlines – it’s the people. You can have the best plans, the clearest goals, and the strongest work ethic, but strained relationships can make everything feel heavier than it needs to be. The upside? Your day-to-day experience can be totally transformed by proactively pursuing ways to collaborate with these complicated colleagues. 

Admittedly, this does take some work, and you may be wondering whether it’s worth it. After all, you’ve already honed CIA-level stealth tactics to avoid them wherever possible. 

Communication sounds simple: you say something, people understand it – easy, right? But the reality is a lot more complicated. We’re imperfect beings trying to connect with other imperfect beings, and misunderstandings aren’t the exception; they’re part of the deal. To truly connect with complicated colleagues, it helps to step back and rethink your communication style.

The first thing you’ll want to do is think about the direction of your communication. Speaking upward to leadership is very different from talking across to peers or downward to your team. 

There are many reasons you might label someone as “complicated.” Maybe it’s their communication style, attitude, or just that they move through the world differently than you would. But often, the real frustration boils down to the gap between who they are and who you expect them to be.

Here’s a powerful mental unlock: stop being surprised. Expect people to be complex. Walk into conversations, meetings, and email threads knowing things might get messy. Don’t assume everyone will agree with you, see things your way, or communicate with perfect tact. Letting go of these hidden expectations will protect your energy and give you back a considerable sense of control.

Sometimes, no matter how many books you read or tactics you try, collaboration just isn’t going to happen. Some people simply aren’t willing or able to meet you halfway – and that’s not a reflection of your effort or attitude. It’s on them, not you.

The good news? Truly impossible collaborators are rare. Most people, given time and space, can grow and change. But every workplace has a few who may never quite get there. When quitting isn’t an option, setting boundaries becomes your best plan of attack.