Balancing Hats

Here’s a simple framework for deciding what you have to do, want to do and are good at. Follow the steps below to complete the exercise and find some balance!

First, identify the “hats” you are wearing today. This can be done together with personal hats (mother, caregiver, volunteer, etc.) or two different charts— one for work and one for non-work hats.

These are the most common categories that are usually divided among cofounders and/or first hires at an early stage startup:

• Strategy: Determining the company’s true north, near- term direction, and making critical decisions about things like fundraising, revenue and human capital. Strategizing also includes defining and communicating why the company is doing what it does, which is as important as where it is going. CEOs rarely take off this hat.
• Product: What the company produces. In the earliest stages of a venture (rowboat and maybe motorboat) the person wearing the product hat may be responsible for customer discovery, design, building, shipping, and support. Wearing a product hat also includes prioritization and tradeoff decision- making for features, new products, and services. Many startup CEOs and/or CTOs are product people, and this is usually the first hat to put on and the hardest hat to take off— if ever.
• Culture and Process: If the culture doesn’t work, then the processes won’t work either. Creating high-performing, inclusive, and diverse teams goes well beyond what workflows, policies, and procedures are in place. Culture and process is how the team communicates, operates, and evolves as a living organism. Some founders are natural culture builders and systems thinkers, but if these are not strong suits, culture and process is definitely a hat that should be worn by someone else on your team with these propensities.
• Talent and Development: Who you hire and how you develop the team will determine whether the venture can scale successfully. As companies grow, there will always be tradeoffs on when to promote from within, when to hire more experienced talent, and when it’s time for some team members to move on. CEOs often wear this hat more often than others, but many have COOs or strong HR leaders on their teams who wear this hat permanently.
• Other Functional Areas Like Marketing, Sales, Support, and Finance: Brand identity, closing deals, supporting customers, and managing cash flow all require high founder engagement. Some founders are very functionally oriented, which can derive huge benefits for the business as long as there are capable leaders on the team wearing other hats.

Reflect on the hats identified and assess your have-to-dos (HTDs), want-to-dos (WTDs) and good-ats (GAs) today. Y for yes and N for no. This assessment is subjective and requires a large dose of humility— what “good at” means to you may be viewed differently by others (team, investors, partner, etc.). If unsure, ask for candid feedback from your team and/or investors. Here are a few prompts to consider:

• How are you spending most working hours of your day?
• What are activities you are excited to get to in a given day or week? Which are you frustrated that you are not getting to? (have to do/want to do) Which do you dread? (don’t want to do)
• What activities bring you joy when you completely them?
• What activities, even though you are good at them, are mundane and could probably be done by someone else?

Define the actions you plan to take to change your Ys to Ns or vice versa. For example, if talent development is something you have to do, want to do, but you’re not good at it, what steps will you take to improve? Hire a coach? Take a course? Read a book? Or, maybe routine accounting is something you are good at, but may not have to do, or want to do it so the action may be to hire a bookkeeper.

Decide how you’ll measure your actions. How will you know you have effectively achieved your goals? Will employee satisfaction or retention numbers improve and, if so, by when? Will employee satisfaction or retention numbers improve and, if so, by when? If you are hiring a bookkeeper, when would they come on board and how will you know you’ve officially taken that hat off?

Once you’ve done your balance assessment, consider discussing with cofounders, employees, advisors and/or investors. Ask for support especially if taking off a hat may slow something down for a bit until you catch up on something else. Perhaps someone can pitch in or suggest a contractor to help out, or maybe just empathize and offer emotional support.

Revisit this exercise at least once a quarter to be sure you are staying on track!

This is an example from a CEO I work with, but anyone can complete this exercise – founder, joiner, investors, partners, etc.

In this scenario, the CEO prioritized product, people, strategy, and process as the hats they have to wear. Here’s how they thought about these and the other hats:

• As a former engineer, product is their area of expertise and, at their startup’s stage, it’s a hat to keep on.
• Both people (hiring, culture, etc.) and strategy were important hats for this CEO to wear, but they felt their skills in both areas could be improved and decided to work with me as their coach to develop those skills.
• Even though they are good at accounting, they didn’t enjoy that work and knew it could easily be handed off to a bookkeeper.
• Finally, this CEO felt they still needed to be involved in sales, enjoyed that work, and was good at it so would keep that hat on for now.

Depending on the type of business you are in, there could be other hats to wear for domain- specific areas, such as clinical hats for a life- sciences business or a data-science hat for an AI-centric startup. Figure out which ones are important in your organization, which ones are clearly being worn by someone already, and which ones need owners.