Managing “Difficult People”

Yaniv Preiss
5 min readOct 1, 2023

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Reservoir Dogs — 1992 Film

When talking about performance, it’s crucial to consider both the technical (a.k.a “hard”) skills and the interpersonal (a.k.a “soft”) skills. An employee is not a high performer if they are technically excellent but tear the team apart due to their behavior.

After managing people for a while, you might catch yourself thinking about one of your direct reports that they are “difficult”, and you wonder whether it’s your fault or maybe the person is not a good fit.
As we’ll shortly see, it’s very generic and not helpful to label someone as “difficult”.

Have you ever come to work thinking to yourself “Hmmm, today I will do real damage”? Probably not, and probably no one else does. They may display behaviors you consider wrong or harmful, but still assume positive intent — people try to do the right thing and not err on purpose.

First of all reflect — are they actually getting to the desired results and keeping relationships, but they simply do it differently from you? Does it really matter then?

Attitude?

So maybe you think the person has a “bad attitude”.
What does it actually mean? If I tell you about a person you’ve never met before, that they have a bad attitude, but you never notice any behavior to support it, do they really have a bad attitude?

If you ever tried to accuse someone that they have a bad attitude, even immediately after a specific incident, you know they can easily reject the claim, e.g. by saying “I was only telling the truth”. You can never know what’s on other people’s mind and infer intentions.

Even if you were a certified and experienced therapist, it wouldn’t be that easy to resolve “attitude” problems.

But what can you do as a manager?

You can talk about specific behaviors. It’s the behaviors that get results.

Behavior

  • The words you say (or sounds, or not say)
  • How you say them (tone, loud, speed, emphasis)
  • Facial expressions (smile, frown, raising eyebrows)
  • Body language (lower chin, cross arms, brush off)
  • Work products
    > relationships (strengthen or damage)
    > quality
    > quantity
    > timeliness
    > accuracy
    > documentation
    > safety/security

First try to crystalize to yourself on what way the direct report is difficult — can you break down specific behaviors that are causing specific issues with you or their peers?
Then pick a single behavior that you consider the most important to improve on.

How to improve behavior

1:1 — Create the rapport and trust with the direct report for several weeks, get to know and prove you care about them.

Feedback is both negative and positive and is only about the future.
First give positive feedbacks about real demonstrations of any other desired behaviors to build credibility.
After a while tell the direct report that when they display the undesired behavior it causes a specific problem and ask if they can work on it. Examples:

  • “Can I give you some feedback?
    When you cross your arms upon disagreeing with a colleague, it’s perceived as disrespectful. Can you avoid that in the future?”
  • “When you say you don’t care about the topic we’re discussing in a team meeting, it sets you apart from the team. Can you work on it?”
  • “When you raise your voice at a colleague, it tears down the team. Can you stop that?”
  • “When you frown at others’ ideas, you’re perceived as trying to be superior…”
  • “When you pound the table, it scares people…”
  • “When you interrupt others, it’s rude and ruins relationship…”
  • “When you don’t share ideas, it’s perceived as if you don’t care…”
  • “When you’re only negative about others’ ideas, it’s perceived as attack…”
  • “When you only do tasks when reminded, it make me think our priorities are misaligned…”
  • “When you disagree only by saying ‘you’re wrong’, it tears the team apart. Can you disagree in other ways?”

If the behavior continues, repeat that it causes a specific problem and ask how they can work on it.
If they don’t have ideas, ask if you can suggest your own.
If the behavior still continues, give negative behavior about it, and dictate the behavior you want to see.

Training is the act of teaching when you are the expert matter, which means, you are teaching the theory, show how to execute, do together with them and let them execute with your guidance and feedback. This might require a significant time investment from you.

Coaching is the supervising of the process of the direct report’s efforts to improve in favour of the organization. This means that you don’t have to be an expert on the topic, rather you guide and support the process of defining a measurable goal by some target date, finding resources together with the direct report and coming with a plan for them to execute and report on.

A refusal to receive feedback and act on it is unacceptable — we’re all paid to be effective, not to be comfortable. Moreover, the environment constantly changes and grows — the industry, competitors, company, colleagues. If one is not growing, they are going backwards.

Change is hard. If the behavior change is not crucial, then do not punish for incompletion. They did their best and maybe got 60% improvement, so celebrate that!

If you deem the behavior change as a “must” (a.k.a career limiting), make sure it is really clear to the direct report. Warn them that they will not be able to keep their job unless they change. An official PIP (Performance Improvement Plan) might be necessary, with a target date and measurable goals, and hopefully it will succeed. If not, the last thing to do is to let go.

The trap

Exercise: let’s say you have 3 direct reports: Alice, Bob and Charlie.
On some generic scale, Alice is excellent, Bob is doing OK and Charlie needs to improve.
With whom would you spend more time?

Many would respond Charlie, because this way we can “fix him” and improve the whole team.
But if you think about it more carefully, it makes little sense.
If your spending time with them generates a 10% improvement, then if Alice is at imaginary level of “80”, it will translate to “88”, and Charlie’s “40” will translate to “44”.
Obviously 88 instead of 80 is a big improvement to the team, while 40 to 44 is clearly not.

Therefore, spend more time with the highest performers, and it still doesn’t mean neglecting the lower performers, if you have the required resources.

Resources

Manager Tools — actionable guidance for managers

Effective leadership is learned
To learn more or reach out, visit my website or LinkedIn

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Yaniv Preiss
Yaniv Preiss

Written by Yaniv Preiss

Coaching managers to become effective | Head Of Engineering | I write about management, leadership and tech

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