Taking Off Hats

Hats for sale
Photo by JOSHUA COLEMAN / Unsplash

At a startup, everyone needs to wear a lot of metaphorical hats.

With a small team, each person can have many responsibilities. Most companies have a pair of co-founders, one technical and one business-focused, on day zero. The CTO often must act as a product manager, engineer, technology operations, and IT support. The CEO must often do finance, legal, marketing, customer support, operations, etc.

As the company grows, it hires more people to do more things. The company moves from one developer to several. The company might hire a marketer, a product manager, a designer, a customer support person, and more. As each person is hired, they take on a role and wear one or more hats. The co-founders still have responsibility for these areas, but they start to take off a hat.

In the early stages of Wallaby, lasting well into our second year, I was the co-founder and CEO and also (with the help of a few interns) did data entry, blog post writing, social media marketing, and customer service. We decided to hire a multi-faceted role we called "Content, Data, and Community Management" to take on many of these functions. It was three part-time roles pulled together into a single one.

As we continued to grow, we had to take these roles and split them apart. We had more needs than part-time for each sub-function. For this person, the hats had to come off.

As you grow, which all startups want to do, the roles become deeper, with more subject matter expertise, rather than broader, with more responsibilities overall. The leaders of the startup, the co-founders, and the executive team they bring on have to have more breadth over time as the startup becomes much more complex, but with less depth.

For a leader, like a CEO or someone in a role as Chief Product Officer, it becomes impossible to know everything that is going on.

That lack of detailed knowledge is a tough pill to swallow. In 2016, I realized that I didn't know how the Wallaby app worked in detail. I once wrote the requirements, managed the data, and answered thousands of customer support requests. Then, several years later, I realized I was focused on so many other things at the much bigger parent company. I trusted the team to manage the app directly without me.

It is tough to make this transition for everyone. For someone on the front line, it may feel like their job is getting smaller as the hats come off and the knowledge gets deeper in specific areas. For a founder or executive, you have to trust that your team knows what to do and that you no longer have to know everything.

When I became CPO at Bankrate, I tried to know everything on every team. I wanted to answer any question intelligently and correctly on the spot. I couldn't. I don't think it's possible. I had to learn to be comfortable with saying, "I'll get back to you on that."

The real challenge of growth and management is hiring the right team and then giving them the right tools and directions so that you can trust them. There are many right ways to do the same thing. As a leader, you don't have to make your team do things your way, as long as they do them one of the right ways.

Many days I am (metaphorically) hit upside the head about something I don't understand or know about because I don’t know how everything works at my job. I wish I didn't have this experience, but it is OK because I have the right team to take the right actions. No one wants to be micromanaged; I need to have on the right hat, and each team member needs to have the proper fitting hat for themselves.