Overachiever Culture

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

Let’s think about it from a financial standpoint. If you have two years of runway in the bank as opposed to two months, it’s more difficult to stay focused on what’s most important. Distractions can creep in.

Forced constraints can help you develop great habits, too. By working no more than 8 hours a day, you’ll be more productive than if you had worked a 12 or 16-hour day. In most cases, more isn’t better even though cultural norms lead you to believe the contrary.

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 17, I spend a lot of time thinking about how to maintain a culture of overachievers.

All successful businesses start as overachieving founders. A few people take on the roles and responsibilities of about ten 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 their goals. No one says, “that’s not my job”, they just find a way to get it done and push forward.

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. 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 shrinks. Imagine that.

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.

So what does overachiever culture mean from a practical standpoint? It means keeping an MVH: minimum viable headcount. Headcount correlates to overhead. It means more meetings, more complicated org 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 an incredible amount of overhead. Each person would have more ownership and greater pressure to deliver for our customers.

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 person.

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 to 34 again this year. There’s no doubt I wrestle with my own opinions and adjust as I learn new things. But considering all that we’ve accomplished, I still think we’ve got an overachiever culture today. My responsibility is to keep that spirit intact as we grow.

So how do you keep a scaling company feeling like an overachieving startup? 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. Everyone has to feel like they are making a difference, and that the business can’t move forward without their 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, ownership and leadership, 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.