How to Deal with Difficult Employees as a Manager of Customer Success

How to Deal with Difficult Employees as a Manager of Customer Success

I remember thinking one morning “I’d rather set myself on fire than have my 1:1 with her this afternoon.”

A bit dramatic? Perhaps. But most managers have been there. And if you’re looking to move to a leadership role, you need to know how to handle these types of situations.

Because the truth is, not everyone will be your cup of tea. They talk too much or won’t stop humming. Or maybe they are on the opposite end of the political spectrum. Then there are those who are straight-up rude to you and really push the limits on how they treat others. They aren’t quite breaking the rules, but they have a negative impact on the team.

Here's what to do when you feel this type of reaction towards a direct report.

Assess if the situation is personal or performance-based

Things can get a bit muddy here. It’s easy to take certain actions as signs of disrespect – especially as a new manager trying to build your confidence. But make sure to isolate their behavior from your interpretation of it.

Are they constantly late? Yes, this may be passive-aggressive, or they may have legitimate issues with their public transport system.

Is their behavior affecting their performance in a measurable way? Or hurting the team?

Performance-based issues are easier to address than a bad attitude, which can also affect the entire team. A bad attitude is more difficult to measure but just as important to discuss.

Bear in mind too, that when an employee has a bad attitude, it is most likely due to resentment. Ask them during their 1:1s if they feel they are treated fairly at your organization. Don’t sit waiting to contradict them, just listen. Few people are truly lazy. Most are just disappointed.

Stay curious

Always try to give them the benefit of the doubt. Assume good intent - otherwise, you will make them defensive.

There’s a big difference between:

“You’ve been late a lot lately…” and

“I noticed you’ve been late a couple of times this week. What’s up? Everything ok?”

No one is all good or all bad. It’s unlikely they go home and kick puppies while plotting new ways to piss you off.

There’s a human in there, and no one’s life is perfect. Consider the full picture of them as a human. Something hard is almost always going on - for everyone. They could have a sick parent, be worried about a child, feel misunderstood at work, be going through a breakup…

Don’t make something up in your head, just use this to realize that they have things going on in their lives that you know nothing about. You don’t have context.

Assuming everything IS okay, you can then move on to: “Ok glad to hear it. Are you able to arrive on time moving forward?”

Get them to commit to changing their action. This makes any further follow-up much easier, but most of the time you won’t need to.

Understand the threat level

Most of the time when we get our hackles up about someone, it’s due to fear. It never feels this way, but if you dig into why you don’t like someone, it will most likely come down to your fear of losing something – your job, the respect of others, your relationship… If there is no potential consequence involved for you, why even care?

Once you pinpoint what you are afraid of losing, assess how likely that is to happen. Most of the time, there is no real threat. Once you realize this, it tends to soften your reaction so that it doesn’t take up so much energy. You might still not like them, but it will be an annoyance rather than something that affects your life.

Set your boundaries

The bottom line is, they are doing something you don’t like. It’s ok to let them know that. Boundaries can sound serious and confrontational, but they don’t have to be, it’s just letting people know what’s ok with you and what’s not. Cite a specific instance rather than “You always talk over me!”.

Performance issues are one thing, but disrespect is another. You let one or two things go, because you don’t want to be oversensitive, or don’t feel comfortable documenting it. The problem is, if you don’t nip it in the bud, it will only get worse. They are seeing how far they can push you. When they say something that’s just over the line you can start with “What do you mean by that?” This usually causes immediate backpedaling, and the message has been sent.

If for whatever reason this doesn’t work, you can tell them, “I will always treat you with respect. I expect you to do the same.” Then get some advice from your favorite person in HR…

Focus on the positive

Do what you want others to do for you, leverage your strengths.

So for your direct report, focus on what THEY do well. Are they fantastic with data? Great! Give them numbers to crunch that can lead to greater customer insights, and then show appreciation for that. Give them a win. That can make a big difference in their attitude.

Focus on performance

The bottom line is, you don’t have to like them. Are they doing their job? Are they getting the things done that are on their job description? That’s really all that’s necessary. Not winning a personality contest.

If someone showed you their stats along with an employee you do like, would you be able to know who is who?

If there are performance issues, show them gently where they are falling short, then offer to help them improve. Ask what they need to get there. If they don’t know, offer suggestions. Approach their setback as a challenge to overcome together.


You can’t be a true leader if you only lead those you like. You need to have the integrity to treat everyone with respect, regardless of your opinion of them, and enable them to do their best work.

Think more about the big picture of what you are trying to accomplish, and the things you don’t like will fade into the background.

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