Managing Difficult People

by Michael Ruggiero

People are difficult in different ways, and not all of them are catalogued here. These types are all rough approximations. I’ve experienced them all:

I have my own way of doing things

  • Ted likes to come in late, every day. He asks that we never schedule meetings before 10 because it’s really hard for him to come that early, which effectively means the team’s schedule is determined by one person * Alice doesn’t really want to work on projects that aren’t “interesting.” She’ll say “project X isn’t interesting to me” and will get out of working on X for that reason. Sometimes she’ll bargain with you, or with co-workers, in order to work on the stuff she finds “interesting”
  • Bob asks: “Is it ok if I don’t do a code review? I feel like it is really hard for me to be exposed to that kind of critical review.”
  • Carol says “well I don’t really think that [working on technology X] is why I was hired”

Tortured genius

Rather pervasive in our line of work. In their own assessment, they’re quite good: good code, good brain for programming trivia, good on the fundamentals of Some Aspect of Engineering. Tend to not champion others or even recognize skill in others. Critical, opinionated, but lacking in allies. No one sees their point of view, and they don’t know why, because it’s more or less correct. (I had one person say “hey, Sandi Metz and Uncle Bob said it, so it’s true.”)

You (my team lead) are an idiot

Person just doesn’t respect you. They think you’re a joke. Maybe you were once peers and now you manage them; maybe you don’t know anything about Some Technology and therefore don’t deserve respect; maybe it’s personal animus. It doesn’t matter because whatever you do will be greeted with scorn bordering on amused disbelief.

Not really listening

The person for whom you have to say a thing over and over. And over. “Please don’t commit println debugging statements to master.” Later that day: a println debugging statement is in master. Are they not listening?

Incredibly difficult people

Not super-common, but incredibly difficult people (and their cousins, narcissists) are out there. Beware! They often appear to be high-functioning, accomplished people and very good at creating alliances. Good at reading people, particularly people’s vulnerabilities, and great at exploiting them. So what should you watch out for? Here are some behaviors:

  • Starts strong and committed, but something happens and their effectiveness fades
  • Builds fast friendships and alliances, but they tend to turn sour with matching speed
  • Prone to inappropriately extreme emotional reactions
  • Unable to accept responsibility; causes run from “it was like that when I got here” to “other people are making my life hell” to “I got sabotaged” to “my point of view is not supported”
  • Hoards work
  • Claims that without their efforts, you would be screwed

The bumbler

Never seems to get things right. Commits huge bugs to master; comes up with crazy ideas that are not needed; seems to be at the center of crises; doesn’t grok the main things team is trying to get done. Can be overly-diligent about something irrelevant because they are afraid to do something else.

When you explain that things need to improve, doesn’t get the hint that you are seriously saying things NEED to improve. Often ends up working on tasks so low-risk that their bumbling-ness is shunted off. Examples: build tools that are not helpful, performance analysis that no one reads.

So what can be done?

OK that all seemed rather pessimistic, didn’t it? Did I mention that managing people is hard? You have to balance respect for the awesome person who is unique (and they are all unique), with being honest about the person who’s hurting the team.

Sometimes it’s best to be rather blunt and tell someone: I see a trait or a practice that prevents you from being more successful. Sometimes you can help them find the niche where they can be successful. Sometimes you need to fire them. Here are approaches for each type:

I have my own way

Some people do have their own way of doing things; you have to respect that. People need your space and support so that they feel challenged and valued. But there comes a time when what someone wants is harmful to the team. What is good for the team is really more important than what is good for one person’s flow.

Do they get special treatment? Are they “so good at what they do” that the rules are lightened (just for them)? Are they disrespecting others? You have to be very crisp about your limits here. Respect those limits, communicate them to the person.

Don’t do it in front of the team, take them aside. “This is a problem, the solution is you doing (or not doing) X, that’s it, let me know if you want to discuss further.”


I noticed that you were late for standup on Monday, Tuesday and today. I need you to be at standup every day. I realize it’s hard to get here, and stuff happens, but we are all committed to being here for standup and you are part of that as well. If you have any questions about that, let me know.

Tortured genius

Tortured genius’ low self-esteem will drive them to leave (for “someplace that respects” them), but not before they have taken the team hostage. After people have stopped wanting to work with them, tortured genius will be left to their own devices, and create debt in places you can’t even see. Unless this person recognizes that there is a problem with their self-awareness and lack of humility, they’ll be toxic and you need to fire them.

Your one chance to fix this: get them to teach. If they want to grow, they can be good teachers (because being a good teacher means really learning the edges of what you don’t know). Note: chance of this happening is pretty unlikely.

One anti-pattern I’ve seen: the megalomania of the tortured genius is rewarded by granting them their own team. Yes, you read that right. This is often the case when tortured genius manages up successfully and tells the manager “all your problems are the direct result of your people writing bad code. I can fix that.”

You (my team lead) are an idiot

If they aren’t undermining you, or disrespecting you, you may need to accept the fact that not everyone’s going to like you. If they fall into one of the other categories (tortured genius, not really listening?, bumbler) then look at those strategies.

One technique that I have tried: research something that the person is likely to find interesting and have a purely abstract conversation about it. Don’t talk about feelings at all, keep it all about something for which the emotional charge is very low. I call this the “I like the Giants, too” factor. People can bond over things that have very low emotional charge, like a shared alma mater, or a shared sports team.

For one report, I read essays on free will and agency in western philosophy, and we discussed them in the 1:1, just because I knew she would engage on the topic. It was like a bad talk show on cable access. You may never get this person to respect you, but you can open up a dialog that makes talking less awful and build from there.

Not really listening

They heard you. They just don’t agree, and are unwilling to own it. They believe “my lead doesn’t know what they’re talking about” and passively/aggressively won’t do what you asked. As with “I have my own way,” you need to be very direct:

I let you know on occasion A and occasion B that this is a problem. Now it is occasion C and the problem has continued. This isn’t working. If you don’t resolve this, we’re going to have to address it in our 1:1 as an ongoing project. I may need to put you on some sort of improvement plan. This is really hard for me because I think you’re a great team member and a great person. But we can’t continue to have this conversation. Am I making myself clear?

Incredibly difficult people

You need to fire them. Don’t wait for a “better time,” because they are going to make life impossible, and you’ll still need to fill the position. Better to do it before any more drama gets generated.

The bumbler

Ah, the bumbler. The bumbler is hard because you always think you can redirect them, train them, put them on a different, less-visible project, give them another chance. Because hey, we fuck up too. Everybody is fucking up!

But the bumbler is really a different case. The bumbler creates work for the team, no matter what they do, and it’s very hard for them to not do it. And when you give them more slack, or move them to lower-risk stuff, you are telling the team “the rules don’t apply to this person.” You are shielding them from consequences. And people know that you are not putting the bumbler on important tasks because you know the risk is too high.

You need to put the bumbler on an improvement plan; if they can’t get it together, fire them.

A Final Note

For the more benign types, like “I have my own way” or “not really listening,” you need to weigh the costs & benefits of putting them on an improvement plan. If the plan is really necessary because the behavior is really harmful to the team, only do the plan if you truly believe they can change. If you know they can’t (or if they are not willing to admit that a problem exists), be honest about that and fire them.