Scaling from maker to manager

A few weeks ago I shared some important leadership lessons from Stewart Butterfield, including investing in your own growth to make sure that the founder scales as fast as the company.

Growing with your start-up can be a very tough undertaking for a founder. It requires reinventing yourself dramatically in very little time. When you start your company, you will be a “maker” for most of your days, wearing a thousand hats and tackling whatever needs to be tackled. But as the start-up scales and you hire employees, your day-to-day is taken over by more managerial tasks, like hiring and managing people, running company meetings, etc.

Going from a maker to manager was one of the hardest transitions I went through when building my own start-up and I don’t think I was fully aware of what was happening to me at the time.

Not all start-ups will scale as quickly as Slack did, but all founders will need to grow into new roles as their company grows. And here are some things to consider.

First – choose your path: do you really want to transition into a manager? 

You will first need to decide whether you want to go down the path of becoming a manager or not. There’s typically little choice for a founder CEO. It’s unusual to hire a non-founder CEO early in a start-up’s life because it will most likely fail. But other founders might have a choice between staying as individual contributors or becoming managers (e.g. the difference between becoming a CTO who provides technical direction vs. VP of Engineering who manages the whole dev team).

This decision is tough and further complicated by what you think others expect from you. And, the answer will not be immediately obvious: how can you know what the right choice is when you’ve probably never been in this situation before? Nonetheless, it’s an important question to consider and find your own answer to.

How to grow into the role of manager

If you do decide that you want to become a “manager”, there are a few things that can help you grow in to this role:

  1. Coach: Today, most CEOs of Silicon Valley start-ups use coaches to develop their CEO skills. The Information recently ran an article on some of the most popular coaches in SV. Choosing a coach is a very personal experience, as they all have different styles and backgrounds and one size does not fit everybody. It’s typically better to find a local coach, but great coaches are scarce in smaller ecosystems so you may need to rely on remote coaching.
  2. Mentor: Learning from a mentor is a very powerful thing. The challenge is that there are usually way fewer mentors than there are mentees. One hack is to have “informal” mentors – people you learn from without them directly knowing that they are a mentor for you. I have 2-3 people in my life that I would consider informal mentors; but this relationship works only if you also give back in some way. If you just take and take, these people won’t want to meet with you anymore.
  3. Peers: It has always been easy to connect with peers and talk shop in dense ecosystems. It’s now also becoming easier for founders outside of large ecosystems to connect with peers as well. More and more VCs are making sure they build a community around their founders. For example, at Version One we organize approximately ten founder dinners per year in locations like San Francisco, NYC, and Toronto. We always make sure to invite founders from smaller ecosystems to these dinners.
  4. 360° feedback: To learn how you’re doing as a manager, nothing beats feedback from peers and the people that report to you. Ideally, this feedback should be anonymous so it can be as frank as possible. At AbeBooks we had a bi-annual 360° feedback process and while it sometimes hurt, the feedback helped me identify my weaknesses and grow as a manager.
  5. Feedback from the whole company: At AbeBooks we did an annual survey of our employees to understand things from where they were sitting: Is the vision of the company clear? Does everybody understand the strategic priorities? Do employees think that we are living up to the value we defined? Such feedback at scale can be incredibly valuable and is the basis for measuring progress over the years.

Scaling from founder to manager is more of an evolution than an overnight transition. Great leaders are made, not born – although we tend to see just the end product and not the hard work that led to the success. The keys to growth are a founder’s self-awareness and a willingness to see feedback as an opportunity to grow, not just a criticism.

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