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4 Ways That Help Cut Down Your Concern About Firing Someone

Last week I was laughing with one of my CEO clients about how good leaders often feel more guilty than other people do. This is a real thing: it’s even been written about in Harvard Business Review! The actual subject of our conversation was how to deal with an executive he knew he needed to fire. She had been blocking progress and disrupting the worklife of less senior employees since the CEO arrived on the job a few years before—but he kept raising reasons why it might not be a good idea to cut ties with her.

I’m as big a believer as the next person in guilt as a moral and workplace value (and if you’ve actually worked with me, you may be nodding along as you read), but in this case, the CEO’s worries about himself were getting in the way of forward movement. Here’s how we focused on the needs of the business rather than the CEO’s feelings and managed to dispatch his concerns:

It doesn’t work to wait till “a better time.” This concern rarely comes unless the leader is afraid they haven’t given sufficient constructive feedback and guidance or clear enough warnings about consequences. It often takes the form of “we can’t fire her this close to Thanksgiving/so soon after her dog died/in the middle of the current reorganization.” There will always be another holiday on the horizon, the loss of a dog could be followed by a parent’s illness, and some challenging initiative is always happening at work. 

A better approach would be to provide concrete requirements for complete cessation of the negative behaviors, say, for a probationary period of four to six weeks and continuing thereafter, or else termination will be the result. When that period is over, it’s over. At the same time, it’s crucial to show kindness and compassion throughout the feedback and disciplinary period and to provide ongoing check-ins. 

Confront your fears that you’ve handled the situation imperfectly. The CEO worried that the problem exec would challenge his right to terminate her employment because of the times he had been short-tempered with her or argued with her in front of staff—as if his lack of dispassion meant he didn’t have the moral standing to fire her. And of course, there’s always the vague fear of litigation. 

It’s normal to have said or done some ill-considered things during the course of becoming dissatisfied with an employee and having to provide discipline or remove them. I agreed that the problem exec might exploit any of those weaknesses, but I advised the CEO that she might do that whether she was still employed or not, regardless of whether his overall pattern of behavior had been reasonable. It was at this point that we started laughing about feeling guilty, because the exec had already used some of the CEO’s gaffes to stir up internal dissension. (Just make sure that HR backs you up in terms of how you’ve handled things.) 

Reexamine the idea that you’ve treated the individual unfairly because you “don’t like” them. Good, guilty-leaning people often self-question rigorously and bend over backwards to prove to themselves that they aren’t trying to get rid of someone just because of their personal dislike or discomfort. In this case, the antidote was to assess the damage that the person was doing to the organization. I asked the CEO to look at all the people who had made complaints about this exec or whose work had been undermined by her bad behavior. We considered whether keeping her on staff was worth making good people suffer—and how counterproductive it was to undercut the people the CEO did like because he was worried that it wasn’t fair for him to like them!

Don’t ignore the skeletons in your closet—but don’t worry about them either. It’s natural to worry that a badly behaved person will say bad things about you publicly. This could include revealing personal information that’s usually kept private—about your relationships or health, for example. But rather than fretting about a vague threat of exposure, do a rigorous thought experiment and hypothesize about exactly what would happen if the fired exec actually did make negative public statements about you. In most cases, it becomes clear that it would not be to the individual’s advantage to expose you; otherwise, a counterstrategy can be developed, if necessary, with legal assistance. 

Your responsibility as a leader is to your entire organization and team as well as to the results that you’re supposed to deliver. It’s natural to feel distressed and even guilty when you can’t forge a good relationship with someone or convince them to drop their inappropriate ways and support the team better, but that doesn’t mean you should keep them and let their negative impact on the business persist. 

You can’t afford to lose good people or forward momentum, so it’s damaging to keep a problem person even if they do have certain skills or experiences that would otherwise make them a valued part of the team—if only they behaved better. Perhaps one of the best tools you have as a leader is to arrange for a severance package that will help the problematic person start over somewhere else with a clean slate, creating the possibility that they will actually leave their bad behavior behind.

Onward and upward—
LK

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