Very recently, I was coaching a very talented, budding operator. This was her first role in a management position, but her exec wanted to invest in her, so I found myself guiding her through the many challenges of leveling up her operational skills.
This operator was in a difficult position: for the first time, she had to fire an employee for performance reasons. Despite repeated attempts to bring the employee up to the high bar her company had, they were not making the adjustments they needed to make to perform.
She prepared very well, using many resources at her fingertips like this write-up on Firing Well, and also my Offboarding Checklist. She practiced and made sure to take time to create a container for the soon-to-be-ex employee, who was almost certainly going to feel anger and sadness at the news.
Still, by the end, she felt as rattled as the employee she just let go. What happened? Sending the recording to me, she asked for feedback.
As I watched how she fired this employee, I saw this very talented operator fall into every classic trap I’ve seen first-time operators make.
She said that this was hard for her and her bosses.
She asked whether the employee wanted to hear next steps.
She even allowed the employee to decide when to cut off access to her accounts.
While all of the above might not seem problematic, it is. Below, I'll explain the six most common mistakes operators make when they have to fire someone, and what to do instead. Firing an employee is one of the hardest things any founder or manager will ever do—but there’s a right way to do it.
1. Don’t Make It About You.
When firing someone, managers sometimes feel tempted to say phrases like, "This is difficult for me," or, "Thanks for making this easier on me." I think this comes from a well-intentioned place: often, we use phrases like this because we want to show empathy, that we're not taking pleasure in letting someone go, and we want to show them we're hurting with them. But while these phrases sound harmless, they're not: by telling the employee, "Hey, this is hard for me too," you inevitably shift the attention from the affected employee to yourself. Firing someone means you've just dropped a bombshell on someone's livelihood. In this moment, they're thinking about how they're going to pay for their rent or mortgage, how they're going to find another job, what they're going to do to take care of their family, and how to overcome the shame that accompanies the stigma of being fired. This moment should be about them - not you.
Remember the CEO of Better.com? One of the (many) reasons he got lambasted for how he fired his employees was because he said stuff like, "This is so difficult for me." The more power you have as an operator or as an exec, the more of a jerk this makes you look. If you're letting an employee go, you will always have more power than the person being fired, which instantly makes your discomfort irrelevant.
So what should you say instead? Center the conversation around your employee's experience. “I’m sorry this is happening” is enough, provided you maintain that the decision is firm and final. Don’t pile your own emotions on top.
2. Don’t Ask for Permission to Lead.
Firing someone is uncomfortable, so sometimes, first-time managing operators feel compelled to allow the person they are firing to take the driver's seat when it comes to next steps. In the case of this operator I worked with, she sensed the employee she was firing felt angry, sad, and confused. That led her to ask them, "Do you want me to continue?"
While it might sound good in theory, this is actually very poor form. The employee is in an extremely vulnerable position, and asking them if they want to continue dumps responsibility onto them. They’ve just learned they’re losing their job, and now you’re asking them to decide how to proceed?
Instead, you take the lead. Instead of, "Do you want me to continue?", you could try instead, "I'm going to walk you through what happens next." That way, you're not steamrolling them, but you are actively guiding them through a process they can't possibly be expected to direct themselves.
Please note, it's okay to ask them if they need a second before proceeding, especially if the employee seems emotionally distraught. But it's important to wrap up all logistics of firing well on the same call. Restarting the conversation over and over again at later dates means reopening a wound each time, for them and for you, too.
They may have questions for you, and it's okay to answer them. But don't put them in the position to do prefrontal cortex work when their world just got turned upside down.
3. Outline the Next Steps Clearly.
Too many first-time managing operators try to wing it when guiding ex employees through offboarding details. This breeds confusion and reflects terribly on you and your preparedness.
If the employee has to ask how their benefits will work, who will contact them about last paycheck and severance, what their final day looks like, or anything else firing-related, you're the quarterback that's just been sacked. And worse - if they ask and you don't have the answers to their questions, you've thrown an interception and the other team has scored. Big mistake!
Be ready with a very concise rundown on what they will need to know. Don't be caught with your pants down. Information you will need prepared includes:
- When their last day is
- When their access to comms will be shut off
- What severance you are providing them with
- What help you are providing them with, such as helping them find a new job, writing good reference letters, extending your network, and so on. Just because they aren't a good fit for your company, doesn't mean their skillset won't be valuable elsewhere.
- What work they need to wrap up and pass onto the next directly responsible individual
- What will happen during their exit interview if they have one
Please refer to my Offboarding Checklist for a full rundown of logistics you will need to consider.
When firing, transparency on logistical next steps is a form of kindness. The person being fired will still feel upset, but at least they will have a full idea of what's coming next, and that reduces unnecessary anxiety.
4. Don't Let Them Negotiate.
This one is related to Point #2, Don't Ask for Permission to Lead, but it's important enough to warrant its own callout.
Occasionally, when someone is fired, they try to negotiate, beg, or plead. They might ask for another chance. They might ask many questions, trying to get you to justify why you are letting them go. They might ask whether they can have access to their accounts just a little bit longer, if they can retain Slack access, have time to gather personal files, or continue using company accounts.
First-time managing operators tend to cave. The guilt they feel for doing something so difficult like firing someone is insurmountable; surely they can have a little bit of extra time to off board, right?
Wrong. By letting someone negotiate, beg, or plead, you are prolonging both their suffering and your mental load. For painful events like firing, it's best to rip off the bandaid, all at once. Also, by doing this, you are creating gray areas around company property, sensitive information, and client relationships - a very big, red flag.
If your employee asks for another chance, be gentle but firm that this decision is final and irreversible. If they ask you lots of questions as to why they're being let go, you can try saying, "I appreciate you wanting more information on how to improve. But the purpose of this call right now is to let you know that you're being let go, not a feedback session."
And if they ask for more time to access their accounts, retain communication channels, or anything else in a similar vein, make it explicitly clear: "Your access will be removed once this call is over, as it is all company property. In the event that you have personal files you want to save, please let me know which files those are, and I can send them to you after your exit interview to your personal email address. This is the email I have, is that correct?" You are redirecting the conversation by asking a question, and making it clear what you have said is final. You are also providing a clear timeline - in this case, they can expect their belongings once the exit interview is over. This encourages them to offboard as amicably as possible. This may feel harsher, but it's actually an act of kindness when you keep things clean and concise.
Hopefully, if you did Point #3, Outline the Next Steps Clearly, properly, you will have already made clear, firm decisions on all of the logistical details beforehand regarding company property, and ideally, there shouldn't be anything left for them to transfer.
5. Maintain Authority Without Being Cold.
I've seen not only first-time managing operators, but seasoned operators, get this one wrong. The pendulum usually swings in either of two directions: first-time managing operators tend to be overly sympathetic and try to relate as empaths to their employees, because they remember being an individual contributor not too long ago. On the other hand, seasoned operators tend to go stone-faced to avoid messy feelings, and try to beat the situation up using pure logic and reasoning, making zero room for human emotion.
Both approaches are wrong. Being overly sympathetic drags out the conversation and piles on unnecessary emotional labor. On the other hand, being a robot and trying to logically submit your ex-employee, who is in full-on fear mode, is a jerk move and extremely callous.
So what's the best way to maintain authority, without coming across as being cold-hearted? Use empathetic language, but stick to the facts and stick to the plan. Keep all emotional phrases centered on the person you're firing, not yourself (See Point #1, Don't Make It About You.) When met with big emotions, you can say you understand this is a distressing piece of news to hear, and reiterate that you value the person as a human being (you should, even if they performed terribly in their role.) And if they try to derail the conversation, reference Point #4 - do not allow them to negotiate.
Communicating in a straightforward, practical, and kind manner will allow you to acknowledge their feelings, without inviting them to dictate company policy.
6. Prepare for Emotional Reactions
Firing someone is emotional, especially for the person receiving the news. Expect tears, sadness, anger, questions, and confusion. If you do not prepare for these reactions, you will become flustered and question your own game plan. This makes the entire process more painful, for them and for you.
I was once taught to mentally place a glass box around anyone experiencing big emotions, especially when they were directed at me. By imagining a glass container, it allowed me to see that person, hear everything they were saying, and experience all of their emotions - all without it ever actually hitting me in the face. It felt almost like I was at an exhibit, protecting my sober-mindedness and creating space for the person to fully experience (and exhaust) their large, emotional reaction.
Please make sure you practice placing glass containers around people. You can get easy practice doing this anywhere, using mindfulness techniques. The next time someone driving cuts you off, notice the act, and place a glass container around it. "This person is experiencing road rage and anger. It cannot hurt me if I do not react to it." When your spouse or partner is angry and releasing all of their emotions at you, notice it and place a glass container around them. "He/she is releasing a lot of emotions. None of them can hurt me. I can stand here and listen fully and intently, knowing that I will not take anything he/she says personally."
The fact is that when you react to someone's emotions, it heightens and prolongates their emotions. It's like pouring kerosene onto a fire. But if you allow them to experience their rage, sadness, or frustration, and you listen and acknowledge without emotionally reacting yourself, it's like a bonfire: the fire will eventually die out on its own.
Stay steady and consistent so that despite the shock your ex-employee feels, they understand that you are in control.
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In the end, I gave all of the feedback above to this first-time managing operator, who was grateful for all the tips. She didn't only make mistakes - she did many things right, too: She came up with a plan and timeline, took care of all the logistics on what would happen by when and with whom, and prepared very well for the emotions that came up in her ex-employee. She also shared that she would help this person find a new job, reiterated that she valued them as a human being, and made it clear that they would be receiving severance and a good recommendation letter for a role they would genuinely excel at.
I hope this write-up helps you avoid many of the common pitfalls, so that you can make this difficult process as humane and straightforward as possible.
