Whoever is at work in charge of a team, a department, or an entire company would probably tell you that it’s always better to have long-term trusting relationships with the people they lead, instead of changing the people they work with often.

Although it’s ideal that you become close with the people you work with, unfortunately, sometimes, uncomfortable situations can be even harder because you guys became so close.

This is why sometimes it’s a blessing in disguise when you don’t get work with your colleagues.

When you become close, the motivation for work gets higher, but also less strictness and authority is present.

After a while, you as a boss, feel that your employee is not performing as he was, or that he doesn’t fit the team anymore.

Whether or not they are your friend, the person has been in the company a long time, and you know it will be hard to end it, but you need to find a way to cut ties.

Well, in this article, we will cover:

  1. what ground is there to cut ties with someone
  2. how to end your work relationship with an employee: over the phone or in person
  3. what to expect after you fire someone
  4. pieces of advice for you as a boss

Although it’s true that rarely anyone finds easy firing someone, it’s also true that if there is ground to do it, it’s always better to do it.

We’re here to make this process as painless as possible and help you do this!

Let’s get on it!


You know that time you worked on something with someone, and you didn’t enjoy the atmosphere?

You just didn’t feel comfortable or nice? Surely, you remember at least one of those types of situations. Maybe it was:

  1. when you had homework in school which you needed to do in a team
  2. when you applied for a hackathon or a case study with people you didn’t know well
  3. at your first job
  4. at your current job

There are a lot of toxic workplaces because people become unpleasant because of stress.

It only takes one influential toxic person to spread the unpleasantness through the entire team or organization.

Now, we’ve prepared for you examples of behavior you as a boss should be on the lookout for.

If you see some of these happen, consider your next course of action with that employee, because you might have to fire him/her later.

1. The employee’s performance drops excessively.

Are they late with delivering what is necessary to their clients? Are they having fewer meetings? Are their results getting worse? An employee is mainly judged by his/her performance. After all, they are there to get the job done.

Underperforming is the least toxic behavior, but it can spread easily. If other people see one employee slacking and getting away with it, they might start to do it too.

As a boss, you need to be strict with performance because your results depend on other’s work.

Sometimes, underperformance happens because of external factors like the market has changed, or a new competitor appeared.

Sometimes it can also be because of private reasons: a baby is on the way, or someone in their family has health issues.

Either way, openly talk about performance with the employee and make them know you’re there to help – with more educational training, or maybe with an altered job description with less work until they are back on their feet.

2. The employee is easily replaced.

Sometimes, one of your workers can’t get fired because they have a key position for getting the job done on time.

This postpones cutting ties, so when you want to fire someone, consider how currently they are vital to the team.

If their performance and/or behavior is bad, and the costs of time and money are low for their replacement, there isn’t any need for you to worry how this move will affect the company’s performance.

It will probably be better than before anyway so you will know that you made the right decision.

3. The employee has two jobs.

Nowadays it’s very popular for workers to have a side job.

The hustle culture is getting stronger and more and more people to want to become entrepreneurs.

Not to mention that a lot of people are getting into freelancing waters, which can pay nicely.

You might sense that your employee isn’t fulfilled by his/her work and would like to switch to a different profession.

Also, he/she is losing focus because of the other work, which is more interesting.

Before cutting ties if this happens, check with them if there’s anything you can do to make their current job better.

Anyway, it might even be better for them and for you to let them focus on their side gig full time.

4. The employee gossips a lot.

As a manager or a boss, it’s your job to make tough decisions.

Those decisions are only made harder because you know not everybody is going to like them.

You know those people who openly talk with everyone about how your decision was wrong and that they would’ve made a better one? If you do, then you know how frustrating it is to have them in your firm.

People who gossip are tricky because they can be big influencers on your less-experienced employees.

So, if you notice that there are gossips spreading around, not only about you or your work but also about other people, be sure to find the source of those stories and confront them about it.

5. The employee isn’t accountable.

Some workers have a hard time owning up to their mistakes and being accountable.

They often play the “blame game” by shifting the responsibility to their co-workers or subordinates if they are managers.

But these people are not hesitant when it comes to accepting praise for the results which they accomplished with someone.

Leading unaccountable people is not only unproductive because you never know if they’ll do something that they’ve promised to do, but also can lead to good employees quitting because they feel that they’re not treated accordingly.

Accountability is one of the building blocks of a good performing team, so encourage others to talk with an accountable person as well.

6. The employee put himself/herself before the team.

Having a person who puts their own results before the team’s results is very hard to manage.

Departments which need to work together, like marketing and sales, need good synergy in order for the company to perform.

It’s always better to have good team players, so if you have great solo players work with them, so they become one great part of a team!

7. The employee acts like a dictator.

If you’re higher at the hierarchy in your company, the people who manage people are also your employees.

As such, you should also pay attention to how they treat their people because the workers at the lowest level are the ones who are “on the field” and bringing the results.

If your manager is power-hungry the people, he/she leads won’t trust him/her.

A working environment without trust will never accomplish anything good.

When a manager delegates everything and doesn’t listen to feedback, employees become unsatisfied, and then they start to work less and worse.

So, if you notice that you have a dictator in your team, immediately talk to him/her about that.

After all, it could be that they’re just not aware of their own bad behavior.


At some point, you might see that you and the employee had different visions for the company.

They still work for you because of good conditions, or maybe they don’t want to look for a new job, but you see that their performance is a mere fraction of what it used to be.

You can let the employee know of your decision in a lot of ways:

  1. You can phone them
  2. You can let them know in person

People choose the first two options because they’re easier, of course.

However easy it may seem to avoid eye contact for this conversation, we recommend that you do this in person.

This move is more valued and respected. Also, if you guys have a friendship, doing this in person is the least you can do.

The employee will also better understand you if you do this face-to-face.

However, sometimes you really don’t have time to do this in person, so we will also cover here on how to let someone go over the phone or via e-mail.

1. Cutting ties in person.

i. Prepare to say which behaviors led to this.

This is very important because your decision should be objective and not subjective.

By making them know which exact behavior led to this, not only do you seem more objective, but the person will also know what to work on.

Surely there are big reasons for firing them, so name all you can think of:

  1. being late for work
  2. missing meetings
  3. not dressing properly
  4. using unwanted language
  5. not doing enough work
  6. disrespecting colleagues etc.

Think of it like this – if you were fired, wouldn’t you want to know why you’re fired for, so you know not to make the same mistakes at your next job?

It’s always better to talk with your employee about these things as soon as they happen, so you know you’ve tried to fix them.

This way your mind is easy because you know that your decision wasn’t rash but that you tried and it didn’t work out.

ii. Have an open direct conversation.

When you guys meet, don’t wander around the topic. The sooner you talk about the elephant in the room, the better you’ll both feel. For example, you can begin the conversation like this:

“To be completely honest, I’ve invited you to this meeting to talk to you about finding your way to other companies. I’m sorry that it had to come to this.

I’ve thought about it a lot, and I’m sure that this is the right thing to do. In the past period *now name the situations which led to this*.”

Be prepared for a bad dramatic reaction. Whatever their initial reaction is (it’s probably not going to be a good one), hear them out and try to comfort them professionally.

You should remain calm and remember at all times why you’re doing this, so you don’t give them their job back because of empathy.

Make sure that you let them know their time in this company is valued and that you are sure they’ll find a new job soon.

iii. A complete example.

Hello, welcome.

I arranged this meeting for us so I can tell you that, unfortunately, this is your last day with us. I’ve thought about this a lot, and I’ve decided that this is the best course of action for everyone. In the past period you did this, this and this (name the exact bad behavior which led to this) and we’ve tried to work on fixing these behaviors, am I right? So far, I haven’t seen progress in your work, which is why I’m letting you go.

I know that you might want to say a proper goodbye to some people here, you can do that today or tomorrow. These are workdays so you can reach out to them after work hours. I think that they’ll appreciate it. I will let everyone know what happened once we are done with the meeting here.

I have your final paycheck, which covers everything until today, and I also have a separation agreement for you. This agreement expires in X days, and if you sign it, we can give you $X. I understand that you’ll probably want to review it.

Please collect your stuff from the desk today or tomorrow; we can help you with that.

Do you have any questions?

2. Cutting ties over the phone.

Although this is the worse option, it’s sometimes the only one.

  1. The employee might be a remote worker
  2. You might be in another country, and this can’t wait
  3. They might be currently in another country

First, check if you can even do this legally. It might violate the contract, and you might get a lawsuit if that is the case. Once you’ve checked this, arrange the call and make sure to leave out a lot of time for the conversation.

Book it in the time of day when you have time to talk; you’re not expecting a short call. They will probably talk to you at least a little.

Whether you fire someone over a phone or in person, expect questions concerning:

  1. severance
  2. unemployment insurance
  3. details about termination of benefits etc.


When you cut ties with a longtime employee expect to feel bad if it’s your first time doing it.

You probably don’t like to hurt someone as much as the next guy, so it’s completely normal that you feel bad.

Don’t worry; it will pass. Keep in mind that you did this for a reason.

One of the most important things to remember to do when you cut ties with someone is to take away their access to classified information.

They still might have access to their professional e-mails, and nothing is stopping them from sending out e-mails in the company’s name.

This is unlikely to happen, but know that if people overreact to this, there is no telling what they could do.

So, take away their access to the company’s:

  1. phone number
  2. email
  3. Google Drive
  4. CRM
  5. Social media profiles etc.

What you can also expect when you fire someone is to spend a lot of time making up for their leave.

The search for another candidate may be a long one, and even after you find him/her, it will still take some time until they do the job well.

When you take this into consideration, it is great to have a suited education cycle ready for the new employee, so they learn the job as fast as possible.

Expect to hear people talking about this, especially people who are close to the employee who got fired. Try to understand them as much as you can.

Think of how you would feel if your friend got fired from the same company you guys work in.

But, if the rumors escalate to an unwanted level, confront openly the ones who are talking about it.


  1. Sometimes, if the issues aren’t big enough for the person to leave the company entirely, consider demoting them or allocating them to a different project. This might be a better solution for both of you. Keep in mind that this person has been in the company for a long time and that his/her experience in it is still valuable to you.
  2. Make your final decision on whether you want to fire someone by answering the question “What is best for the company?”. Making the best call for the company is your job, and you know that the company’s needs come first. If you determine that this employee is no longer bringing anything good to the company, or that someone will do everything better than them, then it’s time to let them go.
  3. The more you postpone this decision, the worse it will get. Your company’s performance and culture will suffer more and more. Once you decide that it’s your final decision, execute on it immediately.
  4. If it’s your first-time practice this with someone, you trust. By simulating the conversation, you will prepare for the real one.
  5. Don’t fire someone without warning. In this article, we’ve covered a lot of reasons for cutting ties with someone, but as we’ve mentioned, you should never react on the first impulse. When you notice something bad, immediately talk to the employee about it and be prepared to work it out. Resort to firing them only when you’ve already tried to work with them on their bad behavior and when you’ve warned them where their bad behavior leads.
  6. Keep the conversation from your side short and simple. Be prepared for the conversation to take time, but you should do the talking for only the necessary part. Let them know the decision is final; you don’t want them to start negotiating with you.
  7. Try to end the meeting on a positive note. To help the employee try to give them a boost. Mention what they’ve done for the company and how much that was valued. Name their skills and propose jobs that would fit them. If it’s possible, offer to write them a recommendation letter for future job applying.
  8. If you’re not close with the employee, consider having a third person present for the conversation. HRs are regularly present at these types of conversations and can be of help when you go through this. Not only are they there as a witness, but also to help with dealing with the employee.


One of the points to take out from reading this would be to be careful of who we hire and how close we get to meet them.

But you really can’t predict anything. In different circumstances, you might’ve had everything – a great friend who you do great work with!

Being careful about who you befriend at work isn’t recommended. Rather, focus on good selection processes and give immediate feedback on bad work or behavior.

You can’t find a perfect employee, but you can make one with good communication and their willingness to work on their weaknesses.

When you’re in charge of people, sooner or later you’re going to cut ties with someone. This isn’t only a bad thing, but a good thing as well. You’re saving yourself from stress in the future, and that person will probably be happier somewhere else.

You got this role because you are capable of doing it.

This is just another part of the job description.

Hopefully, in this article, you found how to do this as nice as possible. We got your back and believe that you can do this!

When to Cut Ties With a Longtime Employee

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