How to Work with Difficult People

Maybe it’s someone who makes excuses, someone who has a big ego, or someone who can’t take critique. We all encounter people throughout our careers who are challenging to work with.

These difficult people suck your energy and can, at worst, dampen your own performance. But you’re not powerless. With a little finesse, you can manage these people (or at least keep them from taking over your brain).

The umbrella of “difficult” people usually falls into one of three categories:

  • Logistics: Someone who is hard to get in touch with, hard to schedule, or goes unresponsive for periods of time.
  • Work Product: Someone whose work isn’t up to par.
  • Attitude: This might look like constant complaining, engaging in petty office politics, or being overly defensive to feedback.

Working with people who are hard to connect with is usually the result of out-of-sync time zones (i.e. global teams) or overscheduled, overworked people. In these instances, remind yourself, that the other person is likely just as frustrated as you are. It’s not personal, it’s just the circumstances.

Someone whose work product is subpar is more frustrating, but even in these instances, it might not be personal. When someone is falling short on the job, it could be a training issue, a resource challenge, or even a bad hire. In most cases, this person is not showing up to work with the attitude of “How can I underserve my colleagues today?

For example, when I was in college, I got a new waitressing job. I had waitressed before but at a cocktail lounge. This was a full-service restaurant. In the haze on onboarding, someone probably told me, that when you’re not busy with tables, you should be rolling silverware. Between learning the menu, the table numbers, and the new system, I forgot.

Until three weeks in, a more experienced waitress lost it on me. “You think you’re too good to roll silverware like the rest of us!! I haven’t seen you bring a single batch to the host stand!”

I was stunned. I didn’t think I was too good to roll silverware, for heaven’s sake, I was a waitress! I literally just forgot that single passing comment. Rest assured, I started rolling, but the dynamic remained awkward from that point forward. If you’re dealing with a difficult person in the ‘work product’ category, the first go-to remedy is to be helpful (say it nicely) and not take it personally.

However, the most insidious (and soul sucking) of the three categories is working with someone who needs, as my mother would say, an attitude adjustment.

When someone else’s attitude starts to impact your workday, it can be challenging to safeguard your energy and your emotions. Here’s a model that has worked for me, and the leaders I coach.

  1. Lead with positivity. Positivity at the start of a potentially challenging interaction takes everyone’s brain off the defensive. If you need to deliver difficult feedback, start with a compliment. If you are expecting a tense meeting, start with a funny story. Help everyone step into the best version of themselves.
  2. Be very specific. “Difficult to work with” is a big category. Just like “sloppy work” or “bad attitude,” these generalities can be frustratingly vague. The more specific you can be about the attitude, quality of work, and timeliness that you need, the less likely you are to run into difficulties. Clear expectations are a gift to everyone involved.
  3. Set boundaries. So, they lashed out in the meeting again? It’s an hour of your life that you won’t get back. But those three hours of venting and mentally stewing you spent afterward? That’s on you. The more you can isolate these moments (or people) the less of an impact they will have on your headspace.

Ultimately, you are only in control of your own behavior. Every career takes twists and turns, and on the journey, you’ll run into your fair share of difficult people. They won’t last, but the habits and mindsets you establish in dealing with them certainly will.