In the early days of Gusto, I did it all. One of those things included setting up our physical office space where we worked. We were in a loft at the time, and I purchased the furniture, kitchen utensils, carpets, couches, plants and more. I loved crafting our space and making it an environment we were proud to spend time in, since we spent a lot of time there. But as we grew, I knew that the role would grow and I wouldn't have time to do it all myself.

There was only one thing I could do to make sure our office space kept being crafted with care -- I needed to fire myself.

Don't you mean "hire?"

I think firing yourself is one of the most important rites of passage for anyone who is used to helping with everything. As a company matures, the pie grows larger and the percentage of it occupied by one person needs to shrink. Why? Because there is only so much time in the day. A study from found that the typical executive rises and shines at 6am or earlier, devotes 10 to 11 hours a day to work, and 2.5 of those working hours are spent in meetings.

Every six months, the way a fast-growing company operates must change dramatically. This is because there are new people on the team, more customers in the mix, and what worked previously might not work anymore. The company must shed its skin, reinvent how it works, and the best possible thing you can do is join in on the metamorphosis. Part of this process involves reflecting on how you can organize the set of tasks that define your role. There will always be a million things to do, so focusing on the most important few is paramount.

Although communication and structure will change in a growing company, its values should remain the same. The reason why you started the business and the problem you're trying to fix will likely only grow more meaningful for you. What does need to change is the way the company operates, how work gets done, and who does what. In fact, the same job every six months becomes an entirely new job.

When is it time to fire yourself?

Here are a few questions to think about that will help you unearth your answer:

  1. Are you spending time on the most important thing? It's easy to become reactive given the million things you could be working on. As your company grows, it's imperative you stay proactive and choose what to spend your time on.
  2. Is the task large enough now that someone else should do it full time? Many of the things you did part time can easily become full-time jobs. Think about what would happen if more time were spent on the task, and find someone else who can do it better than you. Then trust and empower them to actually do it.

There will always be key responsibilities for you as CEO. These include setting direction for the business, i.e. what is "due north," as well as embodying the culture, setting an example to the company on how you work with others, and helping to define goals so it's clear what success is. What does change is all of the additional responsibilities you might have had early on when you were filling gaps. I used to run our sales and marketing teams at Gusto, but in the past few years, we've hired amazing leaders in these areas, and now my job is to empower them.

Redefining your role

During Gusto's early days, I made every offer to someone joining the team. This clearly wouldn't scale as we hired hundreds of people, but I still wanted to maintain a connection to the individual teams at Gusto and the different types of work being done. Therefore, a few months ago I started shadowing one person on each of the 37 teams at our company. Every week, I try to spend 1 ½ hours sitting with a teammate, learning about what they do, and seeing if I can help them. There are no pop quizzes or surprise evaluations. I pull my chair up right next to them, take diary-style notes, and try to do some of the work if I can.

So once you've fired yourself, what should you really be focused on? Y Combinator's Ali Rowghani sees it as making the leap from a "Doer-in-Chief" to a "Company-Builder-in-Chief." Once you enter that second phase, Rowghani says you should focus on the things that will take your company to the next level. This means hiring an incredible leadership team, building culture, and making sure people are aligned and getting meaning out of their work. "As a Phase 1 CEO, you are the lead rower on the boat. But in a Phase 2 startup, your job is no longer to row," says Rowghani.

What is firing yourself really about?

To me, it's all about trust. The ironic thing is, what makes you successful as an individual contributor is usually the exact thing that holds you back as a leader. For individuals, doing great work often comes down to controlling the entire schedule, going through each detail, and making sure everything is correct. For leaders, it's about learning how to set direction and then trusting a teammate to achieve the goal in their own way. It's realizing that there isn't just one way to succeed and what you might do is not always the best, or only, way to accomplish the goal. Or as Quip's Molly Graham says, it's about "giving away responsibility -- giving away part of the Lego tower you started building."

Firing yourself is a freeing moment for anyone who does a little bit of everything. It helps you peel away all those to-dos that feel productive, but can easily turn you into a reactive leader. It helps you find your flow -- that special place where hours float by and you don't even realize time has passed. So give yourself permission to reorganize what you do and realize that it's healthy, and normal to make some changes. There's a solid chance you'll be doing it again in six to 12 months as your company continues to bloom.