Leaving your job as a critical employee

Turns out it's not that different from leaving any other job

A little over six months ago, I left my job. I had started as employee number five; by the time I left three years later we’d grown to 150. Because of my position as a founding employee, I had touched most of our company's systems, influenced its culture, and gotten to know a lot of my colleagues. When I googled for advice on how to leave a job where you were a founding employee, all I found were generic articles that didn't resonate. Because of my unique position, I felt that my departure would be somehow special or different than what was in these generic blog posts.

I was wrong. My departure was the same as any other employee's, and the advice from those generic blog posts also applied to me. That said, leaving a company when you've played such a critical role can be pretty scary and uncertain. Here is some of what I learned about leaving a job gracefully from those generic blog posts, my own experience, and the experience of a few similarly "keystone" colleagues.

First, don't feel bad about leaving. At the end of the day, a job is a business transaction (at least in our current capitalist system). You don't owe your employer anything beyond your work, and they don't owe you anything beyond a salary. Your company can lay you off anytime; you can leave anytime. If the job isn't right for you anymore, then it's ok to leave. Loyalty isn't part of the transaction.

In terms of logistics, think about how you want to sequence announcing your departure. As a critical employee, it's likely that you've built relationships with a lot of folks. I ended up telling my manager first, then spending a few days letting my key colleagues know one on one and joining relevant team meetings to share the news, and then after about a week my manager posted about my departure publicly. Many of the colleagues who I reached out to one on one told me that they really appreciated hearing it from me directly. So if you're a keystone employee and you've touched a lot of people, it's good to be thoughtful about how those you've impacted will learn about your departure.

Despite having many reasons for wanting to leave, I found it extremely useful to have just one or two reasons why. I was resistant to the idea at first, but choosing one reason and sticking to it was absolutely the right call. I actually had three versions of my story - one for the folks who didn't need to know much beyond the surface-level, another for my colleagues who I was closer with and wanted to give a bit more context, and another for my very close colleagues who I felt comfortable telling a rawer version of the story. I was lucky that I left my company on good terms, and so I didn't have to work too hard to put a positive spin on my stories. But even if I'd left on bad terms, I would have wanted to find a positive story to tell. I cared about my colleagues and ultimately the success of the company, so leaving trash talking and with flames behind me wouldn't have felt right.

I gave two weeks notice, and I think that's the right call. Two of my former colleagues gave three weeks notice, and both shared that it felt like way too much. Once you decide to leave, you're a lame duck - you lose all of your power and influence, you won't get any new work, and you're essentially in full-time transition mode. In fact, a huge snowstorm took out our power and internet for 3 days my last week of work, which essentially turned my two weeks notice period into a week and half. And to be honest, it didn't have a noticeable impact.

During my transition, my job was to fully transition my knowledge and nurture the connections that I cherished. My role for the year before I left had been focused on knowledge transferring the many hats I currently wore, so I didn't have too much knowledge to transfer related to my current role. Instead, I focused on making sure that folks knew where they could find information about the projects I worked on which predated them all. I didn't re-organize anything, I just made sure that there was one source of truth where they could find directions to the different projects.

More importantly, I focused on culture. I gave a presentation to my data science team called "Claire's soapboxes" (modeled after a former colleague's "pearls of wisdom" - but rants are more my style!) I wanted to leave my team with a better understanding of the things I did which they admired and felt were out of reach - how to be a technical lead, how to lead a "data therapy" session with a customer, how to review each other's work, etc. I also wanted to remind them to zoom out and remember the passion underlying our startup - they weren't there at the beginning when we had no idea whether the whole thing would work or not, but I was. As an early employee, I wanted to transfer that perspective to them. I asked them to look up from the day-to-day chaos to remember that it was truly amazing to work on a technology that actually worked (!!), and that it was extra amazing to do it with a really awesome team.

Finally, it was really important for me to figure out what closure would look like for me (thanks, therapy!). Did I need a heartfelt conversation with the founders to feel at peace? What tone did I want to leave my team with? And just as importantly, what sort of going away celebration did I want? This one is especially important if you're in a remote role, because there aren't any "default" celebrations like getting drinks after work. I told my fellow team leads that closure was important to me and I didn't want just an unstructured happy hour. They delivered, with a beautiful balance of seriousness and fun: a few goodbye speeches, followed by an excellent game, with themes from our work and my personality.

Overall, picking one story, being thoughtful about how I left, and making sure I got the closure I needed made my transition an extremely positive one. I thought that leaving a job when I had been such a critical employee would be an extremely difficult and tumultuous experience. It was hard, but not that hard - turns out it really was just like leaving any other job.