The Unpleasant Business of Firing People


For managers, few things suck more than firing an employee. Terminating a member of your staff is a strangely intimate and perilous action; and all but the most calloused individuals dread having to take such a step. Even though you may feel absolutely certain your decision is right for the company, the team, even the person being let go, somehow that certitude never pacifies the nagging sense that you’re doing someone financial and psychological harm. I’m sure that explains why most leaders wait way too long to take action—often at the expense of their team and their managerial credibility.

My leadership style has always been slightly avuncular. I want my company and my team to feel like a family where it’s safe to debate and dissent. I like to reward ideas; and ideas flourish best when everyone has a voice. But sometimes, in the diverse and turbulent choir of voices in a company, one individual becomes persistently discordant. At Redspring, when that discord became irresolvable and exacted a toll on the company operations or morale, I took action—very often reluctantly. I approached these terminations with a funerary solemnity, treating the departing employee and the fateful disclosure with great respect. A few times, I fired people in anger, which was cathartic in the moment but never felt good in retrospect. After all, when you have the power to affect someone’s financial situation profoundly, the least you can do is keep your shit together, no matter how provoked you may feel.

Most folks I let go handled the situation well, which left me respecting them more at their departure than during their employment tenure. I came to believe that, for someone being let go, the sweetest revenge is a classy exit. Occasionally, someone would receive the bad news with anger, vengefulness, or worst of all, snarkiness. These people might as well have patted me on the back as they left and said, “You did the right thing here, boss.” Nothing makes me feel more justified in taking action than a staffer who throws his colleagues under the bus, as if casting aspersions like rice at a wedding will somehow save his job.

Fire Fast, But Fire With Humanity

You can learn a lot from firing people—from the whole decision process, in fact. All kinds of important leadership traits are called upon in discerning if an employee needs to go, considering the impact of taking action, planning the appropriate way to end the person’s employment, and, ultimately, in how you share the news with staff. Most frequently, I fired people for their failure to honor our core values—and when I did so, I told my staff exactly that. I wanted to show our team that core values are more than placards on the wall and that we expected each employee to conduct him- or herself in accordance with our shared beliefs. If someone disregarded those values, they got voted off the island. When people understand that core values matter enough to get a person canned, they take comfort in that conviction—or they move on. Either way, it’s good for the company.

I’ve certainly made some mistakes in firing people. One woman I fired too abruptly, believing that her manager had given her fair warning that her performance was subpar (the manager hadn’t). I terminated a trusted senior executive based too much on feedback from a couple disgruntled members of his team. Those kinds of mistakes are unavoidable over a long career—and you just hope to make very few of them and that those affected recover quickly. My greatest regret, though, came in not firing people quickly enough. Letting complainers or low-performers hang around only poisons the company well. Putting people on probation when you know they’re not a fit only prolongs the agony and proves corrosive to the very foundation of your business. Taking swift action, however, doesn’t mean acting precipitously or without sufficient information. But it does mean acting with a sense of urgency, as if your business is bleeding revenue while this person stays around (that might well be the case). Most critical of all is that a leader with the authority to hire and fire never lose sight of her humanity, her sense of compassion. Daniel Webster famously said the power to tax is the power to destroy; he would have been no less right in observing that fact about firing people.

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