📸 Computer History Museum, Mountain View, California

Working with difficult people

Alette Holmberg-Nielsen
3 min readJun 24, 2020

Do you wish your team would stop asking questions and just do what you tell them? Do you feel like you have to defend your decisions all the time? Do you wish the people on your team wouldn’t be so difficult? Then you probably have a much better team than you deserve.

I thoroughly enjoy working with difficult people because in my experience they tend to be the people who care the most. I find that people who care

  • are opinionated,
  • insist on high standards,
  • are not easily convinced,
  • don’t take no for an answer,
  • are hard to satisfy,
  • want to understand everything, and
  • want it their way.

In other words, people who care are not necessarily the easiest people to work with. They may come across as demanding, frustrated, negative, and combative. But in the end, they are the most fun, creative, and they go above and beyond to deliver stellar results. I wouldn’t want it any other way.

As a leader working with difficult people who care, there are only a few things you need to do. If you master those things, it’s quite easy.

First of all, you need to understand exactly what your people care about. What is it that makes them tick? What are their reasons to fight for something? You need to be able to ask questions and listen more than anything. What your people care about may not be what you consider important, but people usually have their reasons and it’s your responsibility to understand them.

Second, people who care often have a lot of energy and can be extremely productive. You need to be able to direct all of that energy into something that is both satisfying for your people and valuable to your company and customers. This won’t be hard if you have the right people, because they will want and need to work on what is important and valuable.

Third, when leading people who care, you need to praise and encourage, get out of the way, and be the wind in their back. That’s it. Easy, right?

Every once in a while, it happens that someone who used to care suddenly doesn’t give a rat’s ass about anything at the job. They completely lost the edge they used to have.

I believe it’s a core part of one’s personality to care so deeply that you’re willing to do just about anything to make something work. That’s why it is very hard to get dedicated people to stop caring overall. But it’s definitely possible to put out their fire for a specific project — and that may be easier than you think. When this happens, you may notice that someone’s fire at work is gone, but their pet projects are thriving or they suddenly pick up a new hobby. And no, the solution isn’t to ban pet projects or side gigs. On the contrary — I believe you should encourage them, because they are a very good indicator of how good you are at directing the energy of your people into something that’s satisfying for them. If your people have a surplus of energy and that is going somewhere other than work, you need to understand why. What is it they care about? Why is it so important to them? Why are they not satisfied and content when they leave work? Are their efforts not appreciated?

Working with difficult people who care is not a challenge if you’re always willing to engage in conversation, change your position when necessary and if you have the ability to show that you care by listening closely. Your team deserves it — and so do you!

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