How to Manage Four Types of "Difficult" Coworkers

We've all worked with that one colleague (or maybe even been one)—the “troublemaker” who requires constant supervision.  Bethanye Mckinney Blount, a once self-proclaimed troublemaker-turned-coach for Reddit and Facebook, uncovered four common personality types that are often misunderstood and mislabeled as trouble.  There is hope, though, by learning how these types are best managed, teams can earn greater autonomy to do their best work.

How to Work with Difficult People: Four Types of "Troublemakers"

The Hermit

  • What they look like: This person keeps their projects to themselves and—intentionally or not—will not share their progress until their work is complete. You might hear them say things like, “I’ll have it to you soon, it’s just not quite perfect yet.”
  • What they really mean: “I’m afraid you won’t like what I have so far.” Claiming perfectionism is often really a guise for fear. This person has likely experienced a workplace that criticized ideas that weren’t fully formed and is acting out of self-defense.
  • How to approach them: When you ask for progress updates, realize you’re also asking that employee to be vulnerable. Make sure you’re fostering a supportive learning environment where team members trust each other enough to share. Additionally, if a hermit is used to always working alone, ease them into group work by pairing them with no more than two other people to collaborate with. Explain the group’s purpose and value, and continue to reinforce trust and teamwork. After all, autonomy doesn’t mean working alone.

The Nostalgia Junkie

  • What they look like: This person has likely been with the company since its early days. Now they constantly complain about changes within the company and often bring up how much better things used to be. You might hear them say things like, “It’s too bad you weren’t around a few years ago, it was great.”
  • What they really mean: “I’m worried that I’m going to get left behind.” Every time this person sees new team members join or new initiatives take place, they feel their early contributions may not have mattered enough, and that they could be getting replaced.
  • How to approach them: This type of troublemaker really just craves recognition. Help them feel heard and look to the future by asking what they’re not looking forward to the following week. They might realize they don’t have a good reason to be so pessimistic. Then, ask what qualities of the company they miss the most. If they share a moment of glory they’ve had in the past, look for current opportunities where they could use the same skills to be helpful. This person will be able to work autonomously when they can feel secure that their role still has an impact.

The Trend Chaser

  • What they look like: The opposite of the nostalgia junkie, this person always looks for the next latest and greatest idea or tool. You might hear them say, “I’ve read about this on Product Hunt and I’m installing it.”
  • What they really mean: “Since I’m new here, I feel I need to prove my worth.” This person is often younger, and/or new to the company. They’re excited by possibilities and want to prove how effective they are by finding out what’s trending and sharing it with the company. The danger here is that they typically aren’t experienced enough to know what long-term consequences look like, so new initiatives are started without giving them much thought.
  • How to approach them: Acknowledge that forward thinking is a positive trait, but remind them to look beyond themselves at the bigger picture. When they want to try something new, ask them how they’re going to deploy, scale and support their idea over the next year. Then ask them if they are willing to own the initiative, even if it fails. You’ll feel more comfortable granting this person more autonomy when they’ve proven they can weigh risk and reward, and recognize when something isn’t safe to try.

The Smartest In the Room

  • What they look like: You brought on this person because they were terrific in an interview, had an impressive resume, and they promised they could fix all of your problems. They’re easy to spot because they’re likely also costing you a ton of money. They’re always ready with their opinion and give little regard to other people’s feedback. We’re betting you know exactly what this person sounds like.
  • What they really mean: Sometimes, frankly, this person is just a jerk who means exactly what they say. Other times, though, they might just believe being direct and opinionated is the most efficient way to get things done and are acting that way to help effect change.
  • How to approach them: It’s important to distinguish which type of know-it-all this person is. Are they aware of their image and are actively cultivating it, or is their image an unintended byproduct of well-intended efficiency? You’re not their therapist, so the former might be a lost cause. In a 1:1 meeting, have them take 30 seconds to reflect on what the goal was with their communication and how others may have interpreted the message. If they refuse to self-reflect in a meaningful way, Blount suggests a Hail Mary:

"I list out to them all the tasks and time it took for me to clean up after their shit. This only works if there’s enough of a foundational relationship (read: consistent 1:1s) that she cares about your experience. Tell them that you’ve reached your limit and that we’re not going to have this happen anymore. This appeal has both worked and failed, but it’s typically my last, best attempt to drum up awareness and empathy.”

At the end of the day, you will need to decide if this person is costing you more than they’re contributing (both financially and emotionally). If they aren’t willing to collaborate and take feedback, you’ll never be able to trust them in an autonomous group.

Takeaway: If you want your team to do their best work, first make the effort to better understand them, and then offer support based off of what they need. As Blount says “Have some tolerance for troublemaking. Otherwise, you might end up with a homogenous organization that a single virus could knock out.”


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