Getting fired can be devastating, especially to a conscientious employee. As a manager in the tech startup world, where turnover can be quit...

When You Have to Fire Good People

Getting fired can be devastating, especially to a conscientious employee. As a manager in the tech startup world, where turnover can be quite high and things change fast, I’ve had to let many good people go — and when I do, I’m acutely aware of how painful it is for them. But because I also focus full-time on the art of sales, I’ve learned to think of it this way: 


Firing involves an element of selling. It requires empathy, asking the right questions, and guiding someone to your desired outcome in an authentic and honest way. While I’m selling people on the idea that they’ll no longer be at the company, I’m helping them to see it’s what is best for them as well. This may sound manipulative or callous; it isn’t. When done right, it actually makes the transition easier.

A while back, I fired a content manager. She had previously worked in sales, but was also a good writer and wanted to try managing content for one of my businesses. I figured that having a good writer who knows sales could mean the best of both worlds for this position. But it didn’t work out. I needed to let her go and hire a replacement who knew a lot more about developing content.
Just ushering her out the door never even occurred to me. The idea made no sense. She had relationships with about 30 people outside the company who were providing content for us. They were crucial to our business. If she had left abruptly, it would have damaged those relationships. I wanted her to stay for a transition period. It would be better for her, too. It would give her time to look for the right job.
So we had the difficult conversation. I explained that it wasn’t working out, why it wasn’t “the right fit,” and that I’d have to let her go. And I asked: “What are your goals? Where would you like to go in your career?”
“I should probably get back into sales,” she told me. “That’s really where I want to be.”
At that point, I didn’t have any open positions that would fit. But I had gone into this meeting knowing several other possibilities that might work well for her. (In startups, you’re constantly networking — business leaders are always asking each other if they know of any candidates for certain positions.) So I told her about one job that I thought was a good lead. I got in touch with executives at that firm, made the introduction, and told them honestly that for the position they were looking to fill, she would make an excellent candidate.
She’s now been there two years, and she loves it.
This sort of thing happens often in Silicon Valley, as companies keep evolving and far-reaching networks open up unexpected opportunities. Sure, there are types of firings in which you’re not going to help the person — if they did something terrible or can’t be trusted, for example. But those conversations are less difficult.
When parting with talented people who tried to make it work but couldn’t, like the content manager, I bring three things from my sales tool kit into the conversation:
  • Compassion. I care about my employees and want them to land somewhere great if staying isn’t an option.
  • Curiosity. I want to know what their goals are for themselves
  • A plan. I do my research before every firing so that I walk into the room with ideas to help the employee move forward.
If there are skills the employee needs to work on to meet certain goals, we discuss those. I recommend books and training, as well as jobs at other businesses that may afford them the chance to learn what they need to learn.
I won’t pretend that this approach to firing takes away all the pain and hurt, or that I can always find the employee a new opportunity. Still, giving my best effort can lessen the blow. And eventually, when talented people do land elsewhere, I want them to be good ambassadors. I want them to be happy that they worked for me. I want them to continue to be supporters of my company. My business is on their resume. It’s on their LinkedIn profile. They don’t announce that they were fired, so unless an employer asks for that information, no one will know. If people who used to work for me are off doing great things, it becomes clear that my company has an eye for talent and can be a great stepping stone. That attracts top-notch applicants. Look at the “PayPal Mafia” — that’s the ultimate example.
The former content manager is just one of several fired employees with whom I’ve stayed in touch. Every time we see something good happening at each other’s companies, we send supportive messages to root each other on. We know that as awful as that moment was for both of us, it got us to a better place.

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