If you’ve been with your organization or company for a couple years, you might find these 5 people in your office or Slack channel.


Bob has always been a challenge to work with at the company. Since the day you met him, he’s rubbed you the wrong way. He’s always fighting you, opposing your ideas. Bob is the lead actor in your happy hour rants to your friends. You’re not sure Bob will ever change, and you’d buy the cake for his send-off if he ever decided to leave.


You used to love working with Sarah. You were on the same wavelength and you collaborated with ease. You supported one another’s suggestions and enjoyed chats over coffee. But, at some point, the love affair ended and you now find yourself fixating over frustrations with her. You see her flaws more than her strengths and you just realized you started avoiding her. Weird.


Something has come over Larry. At one point, you’d see his name on an invite list to a conference call or offsite and celebrate. He made every meeting better and you loved having him on the team. But he’s changed recently. He’s not making every meeting better, he’s making everyone bitter. He feels like a drag on the team, and you wonder what’s going on outside of work.


Carrie is the latest victim of your passive-aggressive work culture. She is incredibly difficult, but everyone manages around her. She thinks people like her and enjoy working with her, when the truth is she’s the subject of the meeting after the meeting. She drives you nuts, but you’re afraid if you had a crucial conversation with her, everyone else would leave you stranded on an island and tell her she’s awesome.


You’re the only one who doesn’t know how difficult you are. Carrie can’t stand the way you check out of meetings while you scroll your iPhone. Larry wishes you’d not put him behind the 8-ball when your reports always arrive late each month, leaving him scrambling to adjust. Sarah is working on her communication skills but knows her progress is not good enough for you. And Bob has already picked out your cake and has the design filed on his desk.

Difficult People are Difficult to Avoid

Every work environment has difficult people. Some are always difficult, while others become difficult over time. People can be difficult for a season and there are those who haven’t the slightest clue the challenges they pose.

And then there’s us! You and me – we have no idea all the people who list us as difficult. And if we’re relatively self-aware, we have blind spots and oblivious areas – which even Carrie notices!

We shouldn’t be surprised when we find difficult people at work. They are as predictable as budget preparations and annual reviews, always arriving on schedule.

So, how do we deal with difficult people?

3 Ways to Respond with Wisdom

1. Identify the cause behind the challenge.

There’s a big difference between an “Always Difficult Bob” and a “What’s His Deal Lately Larry.” Bob’s issues are chronic, and Larry’s are seasonal. Not all causes are created equal.

Aristotle once said, “Be kind, for everyone you meet is fighting a difficult battle you know nothing about.” Too many of us don’t know what life is like outside of work for those we spend the majority of our week around.

Make sure you’re showing the same kind of compassion and care you’d want someone to show you if you were difficult to be around. And make sure you’re going after or working on a real problem, not one you imagined.

2. Treat everyone differently.

My grandmother would always buy my dad and my uncle the same thing because she didn’t want to be seen as playing favorites. The only problem was they didn’t like the same things and therefore would’ve rather her treated them differently, rather than the same.

Old-school business thinking says to be consistent in order to never be unfair. But newer thinking suggests there’s room for flexibility and customization in pursuit of equality.

Even in dealing with difficult people, one-size-fits-all approaches rarely fit anyone well. So, adjust your strategy to fit the challenge but always have the tough conversation. Avoiding an issue rarely if ever leads to a good outcome.

3. Own your difficulties regularly.

When someone points out the way in which you’re difficult, own it. I love the philosophy Jocko Wilinck and Leif Babin articulate in their book, Extreme Ownership. These two former Navy S.E.A.L. leaders describe how their code demanded taking responsibility at every turn, owning mistakes and acknowledging weaknesses.

Owning the ways and means by which we pose difficulties for others, along with visible efforts to improve, disabuses those around us of their excuses for writing off our feedback or critical reflection.

Think about it. Would you rather take feedback about your blind spot or flaw from someone who you recently watched own their blind spot or someone who you think flies around with a cape on their back?

Leadership author Craig Groeschel closes his podcast each month the same way. “People would rather follow a leader who is always real over a leader who is always right.”

Embrace the Opportunity

Working with difficult people is our only option because difficult people is all we have available to us. The best case scenario in working with difficult people is to grow ourselves, even as we hope to lead others towards personal transformation.

The worst-case scenario? We end up as a character in someone else’s happy hour rant and their go-to-example for a difficult person, based upon how we treated them and how we did our work. That’s a part no one wants to get cast in and we can all make the decision to avoid.

Photo by Mitchell Griest on Unsplash
We all have to work with difficult people - sometimes we may even be them! But how do we respond with wisdom to people at work that challenge us?