When You Can’t Bring Yourself to Terminate an Employee

All signs point to parting ways, but you just can't seem to do it. What's happening?

Here we go again. You’re listening to yet another employee gripe about Joe.

It’s become a pattern. Surely Joe can tell that his co-workers are avoiding him. Maybe it’s a bad cultural fit — you noticed that he’s barely doing the minimum these days. He keeps making mistakes, and you can’t trust his work anymore. You’ve told him in his performance reviews that his work is kind of sloppy and he needs to do better, yet nothing improves. All signs point to terminating Joe, but you just can’t bring yourself to do it.

Sound familiar? Most leaders struggle with this scenario at some point, especially new managers. You’re dealing with humans, so although you realize you should let them go, actually doing it can be difficult. That’s a natural result of human empathy. The fact that you care can lead you to a more amicable parting of ways.

What would happen if you calculated the hours spent talking with others about the employee’s performance, losing sleep thinking about it, checking (or doing) their work, and giving them more chances? When we ask founders, CEOs and managers to do this calculation, they’re often astonished that the employee is using up precious headspace that should be devoted to key business priorities that drive company revenue and success!

If you’re on the fence about whether you should fire someone, ask yourself, “If the person walked into my office and resigned, would I be sad or feel relieved that I don’t have to deal with them anymore?” Your answer will often help you choose a side of the fence.

If everything points to the fact that the employee is not working out, but you’re still delaying, let’s consider the questions that may be keeping you on that side of the fence:

Will this person be upset at me? I don’t want to disappoint anyone.

The employee may be upset. They may even cry. If you follow the approach we outline below, hopefully the employee will come to realize that parting ways is really the best thing for them as well as the company. If your company doesn’t have the resources to provide a severance package, consider providing a document of resources (career coaching, SCORE, resume writing classes, state/city resources, etc.). It’s perfectly normal to not want to disappoint others as you probably have built connection and rapport with the employee.

As a leader, you also have to think about the big picture. The person getting fired isn’t the only person you may disappoint. If you keep the employee, imagine who else may be disappointed. How much do folks enjoy redoing the employee’s work? Or watching the employee screw up and getting away with it? Or rethinking whether they can trust you as a manager if you won’t handle the problems? Or wondering why they have to work so hard while the problem employee isn’t? You need to think about what’s best for the business and the people on your team. If you forget about these things, morale will suffer.

Is it my fault? Did I hire poorly? Do I suck at hiring?

Rest assured, the majority of leaders have imperfect hiring records. It happens, because no leader is perfect. Could you actually suck at hiring? Absolutely. Think about it…you have a background in tech, finance, science, etc. You aren’t trained in hiring, which is an art and a science in itself. Cut yourself some slack (and get some training).

Will I be seen as a failure? Am I a failure?

It’s natural to feel defeated. Hiring someone who wasn’t a good fit may have been a failure, but that doesn’t mean that you are a failure. Notice the difference? The former is about your behavior, the latter is about your identity. You can test your thinking by consulting with someone you trust, e.g. your boss, peer, external colleague, or therapist. Ask yourself, “What do I know to be true? What are the facts?” If the facts add up to you having tried your best in communicating and holding the employee accountable and it still didn’t work, then you aren’t a failure at all. Even if the facts don’t add up, ask yourself what you can learn from the whole process. Learning will increase your chances of hiring well in the future.


After having addressed some of the psychological roadblocks, let’s look at the more practical side of handling the matter:

How will we meet our goals if we fire them?

Ah, good question. This question points to the larger issue: if one person is responsible for the majority of your sales, science, biz dev, or technology, you need to rethink your infrastructure. No company should revolve around one person. If your team or company is relatively small, then keeping an ill-performing employee can be even more damaging. Trust that other employees will step up to fill the gaps until a new person is hired. Believe us, they do. Cultivate an environment where knowledge and intellectual properties are being shared and transferred within and across the teams.

Could firing this person have been prevented?

Perhaps. To go forward, we recommend looking back. One main reason a leader delays firing is due to ineffective handling of the employee and issues leading up to the moment. When you need to fire someone, it shouldn’t come as a shock. Here are some leadership tips that could lower the chances of having to fire employees:

  • Hire for values, cultural fit, and talents, in addition to hard skills.
  • Clearly define their role, responsibilities, and your expectations. Clarify often.
  • Conduct 1:1 meetings every 1-2 weeks. Have employees send an agenda beforehand, including priorities, data, to-do lists, and completed tasks in an email the day before. Spend time in every meeting providing feedback framed in a way that shows how the feedback is helpful to the employee. Praise when warranted, and discuss errors, behaviors that missed the mark, or areas needing growth. It’s imperative that you explain the impact of their behaviors. Want to know how to give constructive feedback? Use the ABC formula.
  • Establish accountability by always answering these questions, whether in an email, 1:1, or larger meeting:
    • Big picture: what are you going to do?
    • Action items: how are you going to do it?
    • Deliverable: how will I (the manager) know it’s getting done? This includes check-in and deadline dates.
    • Support: how can I help the employee?
  • Be consistent in following up. If they don’t meet a milestone and you ignore it, you might expect more missed milestones.
  • If you’ve brought the behavior up in a 1:1 already, but the behavior starts becoming a pattern, start documenting it and communicate that to the employee. This is also where you clearly communicate the consequences, as in, “This is job threatening.”
  • Be sure performance reviews accurately reflect the 1:1 discussions.

Is it possible to have an amicable departure when the employee is fired for performance reasons?

If you’ve led with empathy and have told the employee how their behavior is impacting their career, team, and company, the employee will often conclude themselves that it’s time to go. It really shouldn’t be a shock to anyone involved. If you follow the above approach, you shouldn’t need a PIP (performance improvement plan). That’s a good thing since the PIP is usually viewed as a death knell and amps up tension. The fact that your working relationship is about to end doesn’t have to negate all the good moments you have shared.

How do I do damage control?

You don’t want the employee to sue or badmouth you online. Documenting along the way should help you avoid a lawsuit. Treating the employee with empathy should mitigate much of the risk of a bad Glassdoor review. Once the employee is gone, create a safe space for remaining employees in their 1:1s to process or vent about the employee’s departure. When you announce the news to the remaining employees, you can be vulnerable and admit that the decision was also very tough for you.

Perhaps, the most important lesson here is for all of us to stop thinking binarily: retention is good and termination is bad. People no longer settle in the same region and job for their entire life. Now the majority of us hop around cities and professions, entering and leaving loose networks. For the CEOs and managers out there, retention and termination mean very different things these days. It is possible that retaining an employee is actually harmful to her and the company’s growth, whereas a farewell can be necessary before you can meet again. Your journey with this employee, as well as your learning as a manager, won’t stop here.

Next post: I’m a founder and I’m exhausted. I feel like I have to work 24/7 because it’s my company. Everyone must be expecting it. I want to elevate existing employees, but I find myself constantly checking in on them and not giving them the autonomy they want. What’s happening?

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