Leader, Manager and Expert – The 3 Startup Roles

At a startup, 3 types of jobs need doing. I call them Leader, Manager, and Expert.

The Leader is responsible for defining strategic objectives.

The Manager is responsible for building a high performing team.

The Expert is responsible for achieving the objectives.

Everybody at a startup wears all 3 hats – only in different ratios.

Working at small (1-10) startups – Expert mode

I've been an executive at 4 tech startups:

• On 3 of them, I was an executive when we were 1-10 employees – very small.
• On 3 of them, I was an executive when we were 150-300 employees – much bigger.

When companies have 1-10 employees, there usually is little Leadership or Management going on. It's Go, Go, Go, ship, ship, ship.

Take, for example, my time at a small (1-10) startup I worked on. The product was successful and made money, but every day, we woke up to a new set of issues that needed to be resolved or fires that needed to be put out.

At this small startup, I remember, in particular, having a task on my list to automate the provisioning of new servers since manual provisioning was so time-consuming. But I never had time to automate it because every day I was manually provisioning new servers to keep our service up!

There was never much deliberation on "what should I work on?" or "is this the right thing?", let alone something like "what is our strategy?" on the small startup.

At a small startup, the company's existential threat, or at least what seems like it, is often staring you right in the face. You just wake up and work on it.

But then the company grew a bit, to around 50 employees, and suddenly, I was not doing any actual work. What's going on?

Working at bigger (11-50) startups – Manager mode

Even if you're a CTO, COO, VP of Engineering, or something else, when the company has 11 people, you're not doing much strategizing.

Which is kinda funny because you're doing a lot of hiring.

When the company is growing, you build many processes as you use them. You may come up with interviews you're unsure are good, and you may have performance conversations without a review process or leveling docs.

For most of my time at companies at the 11-50 employees stage, my time was a blur of interviews and 1-1s.

Ensuring a team is fully staffed, with experts, working on the right things, and motivated is a full-time job, which is why managers are so important for companies and why executives do this exact job as the company grows.

Eventually, you start giving away your legos and hiring managers who will be accountable for their team's successes and freeing yourself up.

And as you free yourself up, you start trying to solve the non-trivial problem of how to get hundreds of people to consistently make tens of millions of dollars in a year.

Working at even bigger (51-300) startups – Leader mode

Any founder or startup executive will tell you that making your first million is much harder than making your first 10 millions. It's absolutely true.

But making your first 10 million requires a whole of a lot more planning to accomplish.

While it was kind of obvious what we each would work on when we were 10 people, and we were all primarily busy building and running teams when we were about 50 people, it was in no way obvious what everyone should be doing at the 200-person mark.

The challenge for leaders is to understand what sets of strategic objectives, when accomplished by groups and teams, would actually lead to the desired company results.

Knowing which strategic objectives will both lead to the best company outcome and can be executed by the current staff is probably an impossible problem to solve and the main reason why strong leaders are so valuable to companies.

Like the three-body problem, where you can't predict how 3 physical objects (say, planets) would influence each other's orbits with their gravitational pull, the subsystems within and outside a company exert and receive influence, creating an impossible problem to model or forecast.

That's why OKRs and similar frameworks are so popular within startups – they give you discipline for outlining and managing progress towards your company strategy.

When you're spending tens of millions of dollars in hundreds of people to try to make tens another tens of millions in a year, options abound.

Therefore, what to do and how to do it require considerable skill to be defined in a way that maximizes company results.

Evaluating the elusive company and individual performance

Everybody at a startup wears all 3 hats: Leader, Manager, and Expert, but most of us have an official title with a role to play.

It's essential to evaluate your role to ensure you're contributing at the highest level to the company and being assessed correctly, given your primary role.

Leaders should be evaluated by the effectiveness of their strategic objectives as measured by the positive impact on the company.

• The board or market can measure the company's success through valuation, an operational measurement like the Rule of 40, or anything else the board chooses.
• Companies must clearly define success to evaluate whether the company is being successful or not.
• The strategic objectives are those that, when defined, will optimally improve the company's success given the current staff. This is how you evaluate leaders.

Managers should be evaluated by the ability of their teams to accomplish strategic objectives.

• For this role, it doesn't matter if the strategic objectives are the right ones for the company but whether your team is effective at achieving them.
• This means creating the most successful team you can by hiring, upskilling, and firing.
• As a manager, you focus on the 3 pillars of management: Priority, Competence, and Motivation.

Experts should be evaluated by their contribution to completing their teams' strategic objectives.

• For this role, it doesn't matter if your team is being successful at accomplishing strategic objectives, but whether the expert is directly contributing to their completion
• To evaluate an Expert, you must have clear strategic objectives for your teams and clear differentiators in each of the Experts to accomplish them
• The Expert is then evaluated by how much their direct contributions push the strategic objectives toward completion.

Note: The evaluations above are a simplification by role, not by person. Given everybody wears all 3 hats, no matter your role, you're always contributing to good strategic objectives, your team's success, and directly accomplishing objectives yourself.

But I also stand by the opinion that since everybody at a startup has a different primary role, and all 3 roles are required for company success, one's main contribution and evaluation should be based on whether their primary role is Leader, Manager, or Expert and what's expected of them given their role.

Evaluating your performance

"How productive am I?" or "How productive is person X?" is an elusive question that's incredibly hard to answer in the world of knowledge work.

Instead of measuring actual performance, a lack of framework and guidelines for expectations on each role will quickly lead us to measure imprecise proxies of performance – or forego measurement altogether.

In my opinion, these performance evaluations for Leaders, Managers, and Experts can't happen over small periods of time.

While people should receive feedback on how they're doing every week, under this framework, performance evaluations need to happen quarterly and yearly.

Trying to tell whether someone was productive "today" or "recently" can lead us to measure busywork like how many meetings, how many tickets, how many hours worked, how good those slides were, etc.

This type of performance measurement can curtail the company's actual performance and hide the accountability necessary for Leaders, Managers, and Experts to perform at a high level.

Instead, productivity rolls down from whether the company is successful, which requires leaders creating the right strategic objectives and managers running effective teams that accomplish objectives through the contribution of high-performing experts.

This also serves as a way for you to ensure you are performing and being evaluated according to how you should be:

Expert

• If you're spending most of your time directly contributing to achieving objectives, such as by writing code, doing reviews, writing documentation, following processes – you're an Expert

Manager

• If you're spending most of your time in 1-1s, hiring, collecting and offering feedback, coaching, and firing, to build the best team – you're a Manager.

Leader

• If you're spending most of your time creating strategic objectives, making market, company, and departmental diagnostics, and then defining plans with stakeholders to address them to make the company successful – you're a Leader.

Use the above guidelines and criteria to evaluate how you spend your own time given your role and make the needed adjustments.

By thinking more clearly about what you're expected to do given your role, you'll clarify expectations on your performance and maximize your and your company's success.

References

I edited out the book quotes, but here are some books to read more about each of the roles:

Expert:

• The Staff Engineer's Path by Tanya Reilly

Manager:

• The Making of a Manager by Julie Zhuo

Leader:

• The 4 Disciplines of Execution by Sean Covey