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How to Let Go of a Difficult Employee

Get On Board or Get Out


You know who I’m talking about. That employee with the bad attitude who doesn’t respect your authority. They interrupt you in meetings. They claim you are unfair. They feel underpaid. They rile up the team. They cause a flare up in your imposter syndrome.


You might feel like you need to make everyone happy as a manager, but this is not true. HR permitting, you need to start practicing what I call: “Get on board...or get out.”


Most of the time, both parties will be significantly happier once it happens. So how do you make this happen?


Some tips

  • Brace yourself: You’re going to have a really hard, really uncomfortable chat with your employee.

  • Be respectful: It is critical that you approach this interaction with respect and you check your emotions at the door.

  • Put it on them: Don’t make this decision for your employee, but lay out the options.

  • Be open: For this conversation to work, you need to be open to either outcome.


So, here it goes (Please don’t memorize this! It is for guidance only. The words must always be your own and be genuine.)


Getting Started

  • Book a room

  • Set aside at least a half hour

  • Put it at the end of the day so you can go home afterwards

  • Once in the meeting, set the tone: “I want to talk to you today about something important.”

State the Obvious


“It is clear that our current working dynamic is not productive. I feel that you are unsatisfied, and it is impacting our ability to work together.”


Give the Goal


“The purpose of this meeting is for us to discuss what changes we are going to make to fix this issue.”


Begin with Listening (seriously, only listening)


“Can you help me understand what you’re dissatisfied with and what you hope will happen?”


Ask follow up questions:

  • “Could you give me an example of…”

  • “Why do you think…”

  • “What would be a reasonable approach…”

[This is scary! What if they say mean things to you? What if they demand things from you?]


Set Expectations


“Thanks for giving me more insight into where you are coming from.”


“I have no current plans to make the changes you mentioned, because I don’t want to make rash changes.”


“I’d like to give your feedback more thought and I will come back to you with any follow ups that I have.” ← actually deliver on this, even if the only follow up is to say “Sorry, no.”


Provide the Options


“As the boss, it is my job to make this team successful and [team mission]. Your current attitude towards your work is hindering that goal. You have a couple of options.”

  • Either this is the right fit for you, and you make some changes and get onboard with the work or…

  • This job isn’t the right fit, and we figure out where your path should take you next.

“The option that does not work is you continuing in this role and not changing your attitude and approach.”


“It’s ultimately up to you to decide which path to take.”


Take a Break


“I know we both have a lot to think about, and we don’t need to finish this conversation now.”


“Why don’t you think it over more and come back to me later this week with what path you think is the best option for your career.”


Losing an employee puts a strain on the business, but sometimes it is for the best. There is a professional and caring way to approach this, and it springs from offering a choice.


Get more advice on having tough conversations with your employees.

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