Keeping Our Overachiever Culture

One of the most powerful things you can do as a founder or CEO is force constraints. Self-imposed limitations can unlock magic when applied properly to a team, a product, or the business as a whole.

In many cases, more isn’t better, even when cultural norms lead you to believe the contrary. I see it all the time in the hiring process. Do you think it’s more effective for someone to send their resume to one hundred companies per day or focus all their time on a great application for their three favorites?

Constraints empower you to develop great personal habits, too. By limiting your work day to 8 hours, rather than 12 or 16 hours, you have to be more efficient in order to get everything done. Reasonable work hours are also much more sustainable long-term.

There are countless examples to drive home this single point: constraints help you focus on what’s most important and bring out your best work.

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So how can we leverage constraints to build a better team?

In the last year I’ve learned a lot about hiring, and specifically about what kind of team I’d like to work with every day. With our headcount now at twenty, I spend a lot of time thinking about how to maintain a culture of overachievers.

All successful businesses start with overachieving founders. A few people take on the roles and responsibilities of many people, punching above their weight day after day to create something meaningful. Early hires also have to wear several hats and overachieve mightily to help the business meet its goals.

As a team grows, roles become more specialized and redundant. One designer becomes a team of designers and each has a few specific areas of expertise or ownership. That’s not necessarily a bad thing, but it's important to acknowledge the overhead introduced with each additional hire.

In some cases, the need for every member of the team to overachieve day after day disappears. Somehow as the headcount grows, the net productive output per person shrinks.

Many businesses get along fine with a low net productive output (few overachievers). But that’s not a culture I'm interested in being part of, nor does it seem like an environment that attracts the best people.

I’d much rather work in a business that fails unless everyone overachieves.

What does overachiever culture mean from a practical standpoint? It means keeping an MVH: minimum viable headcount. Headcount correlates to overhead, which means more meetings, more complicated organizational structure, more management, and more tools needed to keep everyone on the same page.

Instead of hiring 30 people to insulate the business and scale, I’d rather hire 10 overachievers and happily pay them what I’d pay the 30 people, because it saves me the additional cost of overhead. Each person would have more ownership and greater pressure to deliver for our customers.

One constraint that helps you keep a low MVH is never hiring before you absolutely have to, even if you can afford it. Unless things are breaking or opportunities are clearly being missed, there’s no need to hire for the future. The need must exceed the overhead and organizational demands created by adding another person.

By way of embracing this constraint, every person has to perform at a high level. In a small team like ours, there’s no room for junior-level positions because the business depends on a high level of output from every single person. Also, when a person isn't able to meet expectations, leaders are accountable to make the tough decision and part ways.

In the same way I believe less funding has extraordinary benefits for early stage companies, fewer people (each with a lot of ownership) brings about a culture of overachievers. They get more done in less time and foster a “we’re in this together” attitude.

Some of you may think I'm not drinking my own Kool-Aid, because the Help Scout headcount doubled last year and will double again this year. There’s no doubt I wrestle with my own opinions and adjust as I learn new things. But considering what we’ve accomplished so far, I still think we've got an overachieving team today. My responsibility is to keep that spirit intact as we grow.

Overachieving as you grow

So how do you maintain the attitude of an overachieving startup as your company scales? I think it has a lot to do with distribution of authority. The more I and other managers can pass authority to contributors on our team, the more ownership is shared amongst everyone. Each person has to feel like he or she is making a difference—that the business can't move forward without his or her contributions.

You know the best part? Most people will overachieve if they know the business is counting on them to do so. Given the right amount of trust and ownership, everyone on the team can and should be able to maximize their net productive output.

But the opposite is also true. Great people in a culture that doesn’t depend on them to perform at a high level won't be capable of much more than the status quo. They can only be excellent if you empower them to be.