The first job I had after college was in consulting. One of my managers there was the first one who wasn't just thinking about how to manage me day to day, but about my skills and growth. I didn’t realize that until later on.
I discovered consulting was not my cup of tea, so I went to grad school, and we stayed in touch. We would talk about his family and the different things he was working on. Then one day I got an email from his wife. I’d moved to California and hadn’t spoken to him for a few months. She said that he had gotten ill and had gone downhill very, very fast and had passed away. I wish I’d told him how much he helped.
These days I run the infrastructure engineering team at Slack. The engineers that I manage work on all the deep back-end systems that, if we do our job correctly, you'll never know they exist: Slack just works perfectly, it's super performant, fast. We're the type of people who are less interested in building user-facing features, but rather in supporting the people who build those features.
I worked for a long time at IBM Research, which is a really amazing place—all these mad scientists wandering the halls. I got to do some really great research work, wrote papers, built systems, got to spend a lot of time with brilliant technologists. But one of the challenges of research is that you build something, you write a paper, and you usually throw it away. It doesn’t become something. And I'm very, very entrepreneurial. So in the end I went and started my own company.
That was when I had the hardest moments, the ones that really challenge you in ways you don’t expect.
One of them was when I had to fire somebody for the first time. I was at my startup; it was early in my career and I didn't understand how to give people hard feedback—I was more focused on being nice and being their friend rather than their manager.
“A big part of [ firing someone is] not talking about how hard it is for you. You need to treat them with dignity and respect, and acknowledge that this is a more difficult situation for them.”
But after a while, there was somebody on my team that I had to let go. This was a talented engineer that I’d hired, but who we realized had a very different skill set than we thought—and it was not the skill set we needed at the time. I was very worried about it, and I knew this was going to be one of those moments that I needed to handle the right way. It really kept me up at night. And I knew whatever the impact was on me, it was going to impact him so much more.
When you fire someone, or when you have a hard performance conversation, you don't want them to be surprised. And I was in this really unfortunate position where I had set myself up to surprise them. That's never good for anyone. And I knew this could be one of those moments he remembers for the rest of his life. I didn’t know what to do.
I looked at this like a race, like a marathon. I’m a runner myself, and when you start running you know it's going to be long and painful, and it's going to push you. But when you run these really long races, you have these aid stations—they often have water or Gatorade or a power bar. I knew it was not going to be easy, but I knew that I was an empathetic, thoughtful human being, and that this is hard for all human beings who aren't psychopaths. So when I started the race I thought, well, I better visit my aid stations—that is, talk to my mentors to figure out what to do. I knew that there were playbooks, I just didn’t know what they were.
I didn’t really have a manager to help me, so I jumped on the phone with someone—a mentor I’d met and really looked up to. She was an engineer who had started her own company and knew what I was facing. She had a full-time job, so we spoke on the evening leading up to the firing. The first thing she asked, the thing she really pushed me on, was: Do you really need to fire this person? Often this switch flips in our head, and we say to ourselves, “All right, they’ve got to go, this is the only option.” She really helped me take a step back.
Then we talked very specifically, very tactically, about how you go about having that conversation. A big part of it was not talking about how hard it is for you as the person who’s doing the firing. Who cares, right? You’re not the one getting fired, so you shouldn’t ever talk about how it’s been so difficult for you, and you’ve lost sleep, and you’ve agonized over this decision. You need to treat them with dignity and respect, and acknowledge that this is a more difficult situation for them—this isn’t a conversation about yourself.
In the end, we had the conversation. He didn’t take it great, because it wasn’t great news, but we treated him with honesty and respect.
Getting advice really helped. That can come from your direct boss, but it can also be from mentors, friends, co-workers. Often you don’t even have a boss exactly, or a manager—you work with a CEO, start a company and report to the board, or work with a lot of investors… but they aren’t your boss. And so I’ve realized that management takes a lot of different forms. There are people I have met in this journey, in the 10 years I’ve been in Silicon Valley, who have had a huge influence over my career, who I’ve learned tremendous amounts from… and most of them are people I’ve never worked directly with.
