How to Fire a Friend Without Losing the Friendship

“But she left a stable job to work for us, and now we have to let her go! I have to make that right!”

Have you ever hired someone, only to have to fire them? Or hired a friend, and it didn’t work out?

A client and I navigated this exact situation this week. My client, Sara, a business owner, hired a local friend to do the administrative work in their business in anticipation of a large contract coming through.

The person they hired was a few years from retirement, but miserable in their job and unsure they could stick it out a few more years. Sara (not her real name) offering her a job felt like the perfect solution for both of them.

Until two things happened:

  1. The big contract Sara had anticipated fell through at the last minute. What would have been two years of full-time work for the new employee was now gone.
  2. Once this person came to work for my client, Sara realized her friend was actually terrible at detail-oriented work, the majority of her job description ????

Files got put in the wrong place, numbers on quotes got mixed up, and it turned out some of the industry knowledge Sara thought this person had was actually quite shallow.

Now, what I should also say is that this person is creative, warm, generous, and customers had great interactions with her. But that wasn’t the work Sara needed from her.

Sara needed to let her go, both financially and because this job did not play to her strengths, but she felt terrible.

They live in the same small town, have the same social circles and have been friends for years. Sara really wanted to preserve the relationship.

When the big contract fell through five months before, Sara had let her friend-now-employee know they wouldn’t be able to keep her on, BUT because she felt so terrible about the situation, Sara told the employee that they could “keep her on until she found something else.”

Considering that Sara was already re-doing much of this employee’s work, she assigned her only about two hours of tasks per day and told her employee to use the other six hours on the job search.

This went on for five months.


Not only was the job search not yielding results, Sara felt the employee was applying for other administrative jobs that weren’t a good fit, and she was terrified she’d be asked to give her a reference from someone local and didn’t want to lie.

On top of THAT, Sara felt the employee wasn’t really focusing her efforts on her job search and frequently seemed to be on social media instead.

By the time we had the conversation about this, Sara was feeling trapped, frustrated, and as if she’d never hire help again.

Are you exhausted yet?

How would you approach this situation?

Sara is an empathetic, caring, and sincere person. She felt deeply responsible for this person’s situation and felt that “she created it, she needed to fix it.”

Have you ever experienced this sense of responsibility for another person’s situation?

It’s heavy.

This is where we started in our coaching session. Here are the stages we moved through to figure out how to handle the situation.

One: Figure Out Where Your Responsibility Ends And The Other Person’s Starts

Sara saw herself as suddenly responsible for the welfare of the employee until she could in a nutshell “pass the torch” to another employer.

When I said, “Wow, that’s very generous. What if she never finds that? Will you support her until she retires in five years?”

Of course, Sara said, “No! That’s ridiculous!”

She suddenly saw that her responsibility as an employer did have a limit. From there, we could start to work backwards to find what her responsibility was in this situation.

Was a year reasonable? Six months? Three more months felt right, on top of the five months that had already been provided.

BUT, Sara was still struggling with the premise of the situation: if she hadn’t offered her the job, her employee would be in a stable job situation, so it was HER fault.

Two: Realizing the Risks

Here were the things I reminded her of: Nothing is secure, and there is risk in every choice we each make.

Nothing is really “secure.” Nothing. Sara has no way of knowing if the employee would have been fired, would have quit anyway for another job that may or may not have worked out, or could have been laid off from the other company. You. Don’t. Know.

We make choices of our own free will. As long as there is no fraud or coercion involved, we are each responsible for the risks inherent in the choices we make. Sara recognized she wanted to take responsibility as an employer to provide severance, but beyond that, every time you hire someone you are not pledging to care for them for the rest of their lives, just like if they decide to quit it’s not their responsibility to find you an employee to replace them.

Three: Decide What’s Most Important to YOU In This Situation and Realize What’s Out Of Your Control

Sara felt strongly that the employee wasn’t being very efficient or productive in her job search efforts. She wanted to give her feedback on her work in the role and “fix” her as a job search candidate, and since she was still paying her, felt she was entitled to tell the employee how, when and how much she searched.

Sara believed that if she just “made” her do certain things as someone who was still on the payroll, the employee would surely have something at the end of three months. She was considering requiring her to report twice each day with exactly what she’d done, which jobs she’d applied to, etc.

BUT, remember they were also friends. Was she willing to have these conversations with her employee and friend, I asked?

“Oh no! That’s going to be terrible. And what if it ruins our friendship because I hurt her feelings? If we’re letting her go in three months no matter what, it might not make a difference and then we might not be friends in the end either!”

The requirements on her employee to prove she was doing her due diligence in the job search had another problem.

“What if she refuses?” I asked Sara. “What will you do? Or if she does all the things you think she should, and yet it STILL doesn’t work out, will that change your course of action to let her go in three months?”

“Well, no,” Sara replied.

“Then what WILL that get you?”

“I’ll feel better that I did EVERYTHING I could to make her successful, BUT it’ll probably wreck the relationship by the end because I’m micromanaging,” Sarah said. “And you’re right, it still doesn’t guarantee she’ll have a job. And we STILL have to let her go at the end of three months.”

Sara realized what was in her power to control and what was not. There was no guaranteeing her employee had a perfect soft landing and her micromanaging would get in the way of what we identified as her most important priority: preserving the friendship.

So considering their employer/employee days were already numbered, Sara decided she would only communicate with her employee regarding her job search as a caring friend, not an employer.

Four: Trust That People Are Naturally Resourceful, Creative, And Whole

Sara was worried she needed to “fix” or “take care” of her employee. While that may have come from a loving place, the reality was Sara wasn’t seeing the employee as capable of solving her own problems.

She was feeling the need to “make sure” she used her time in the best way while looking for a job. Sara believed she knew best for the employee as a person.

How many of us have had a conversation at Thanksgiving dinner with a well-meaning aunt who treated us this way? How did you feel? Irritated? Small? Resigned? Pissed? Disrespected? Belittled?

Here’s the one thing I bet it didn’t make you feel: empowered to get the thing done.

From time to time, as friends or colleagues, we offer resources we have to those we love. That’s perfectly normal. But I’m talking about when we assume we know best, and give the person no credit for where they’ve gotten themselves to this point in life.

Sara’s employee was in their 60’s, had lived a good life, was married with a strong social network, had been supporting themselves financially their entire adult life, had no psychiatric, developmental, or neurodivergent differences that would need to be addressed to reach their potential.

There is no reason to believe the employee couldn’t be trusted to do what’s best for her own life!

When people approach us with the genuine assumption we are competent and resourceful people, we are more likely to respond to them with openness and positivity.

Sara’s Strategy

By the time we finished, Sara felt good that she was meeting her responsibility by offering three more months severance. She would communicate this to the employee so the employee could use this information to make decisions in her job search.

Because we had decided that preserving the relationship was most important to her, Sara decided she would respond to the employee’s job search as a friend (even when she had other ideas as a manager).

She would trust the employee to be creative, resourceful, and whole, and have faith that she would conduct her job search in a way that was best for her.

So that Sara felt she set them up to succeed with as many tools as possible, Sara would offer the employee a few resources for interviewing, resumes, and job searching she had gathered and allow her to do as she wished with them, without judgment.

Ultimately, she couldn’t control the outcome, but at least Sara would feel she had done what she could as far as offering support, while giving the employee space to choose what they felt was best for them.

What Happened – The Surprise Happy Ending

A few days later the conversation happened. By the end of it, they were both crying.

The employee was so upset that she asked to leave for the day right after, and Sara agreed. But on the way out the door, the employee hugged her and told her she was a cherished friend.

Then, on the way home, the employee was struck by an idea.

Her entire life, she had been an artist, but could never figure out how to turn it into a full-time gig. On the drive, an idea came to her: servicing nursing homes and assisted care facilities as an art therapist.

When she got home, she posted some questions to a few people on Facebook that she knew were connected to local facilities. Multiple people responded, including a person willing to help her write a grant request to help fund the work. Suddenly she had appointments lined up for the following week to continue exploring the possibilities!

By the end of the evening, the employee had excitedly written Sara an email saying she had the feeling “Now’s your chance to make art your life!”

She was so excited. She had never considered this could be possible before!

The conversation with Sara had kicked her into action in an unexpected way…and one that likely never would have happened if she had kept her on as an employee!

The Magic Formula: Sara had figured out what situation she could be at peace with, communicated it in a way she felt good about, let go of the outcome, and trusted the other person to be a resourceful human.

Now, you might be thinking, “Oh, man, but this SO could have gone the other way!”

Yep, you’re right. It could have. Sara realized that and had already made peace with that outcome. This is an important part of the process.

The employee could have continued with zero results in her job search after three months and been forever bitter with Sara for letting her go.

Sara decided she had to be okay with that, because the alternative was accepting responsibility for another person’s life in a way that wasn’t appropriate any longer.

If Sara had decided she genuinely couldn’t be okay with that outcome, then she would have needed to make another choice – to keep her employed (maybe forever), to start making her own calls for jobs on the employee’s behalf, or step into the role of career counselor and taskmaster, even if it ruined their friendship. It might sound a little ridiculous, but these are all choices. When we make them with intention, we’re a lot less likely to resent or regret them.

Even if the situation hadn’t turned out so well, the thoughtful actions Sara took — thinking through her responsibilities, her priorities and the limits of her control — ensured that she wouldn’t spend sleepless nights thinking “If only I had…” And it taught her some lessons about hiring employees, working with friends and setting up expectations in her work place.

So, what is this story bringing up in you? Most of us have situations in our lives where we’re taking responsibility for someone else’s work, outcome, or progress.

Where might it be time to let go of some of that feeling of responsibility, by either literally letting that person go, like in Sara’s situation, or by creating some healthy boundaries?

By continuing to take responsibility for that person, what potential happy ending (like Sara’s employee’s realization that she could achieve her dream of making a living as an artist) are you and that other person missing out on?

Or maybe you’re realizing that someone in your life is taking on this role with you, and it doesn’t feel good. How can you think through what you want and what kind of support you need to achieve that, without the feeling of dependence?

It’s possible. Not easy. But necessary.

And as with other things, you’ve got this.




This is the work I do. If you could use some support and think I might be able to help, book a free 20-minute intro call and let’s talk.

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