Outside In

In small organizations, we often don’t have the bankroll to afford top-dollar talent. Most of us are playing Moneyball: we take passionate, culturally aligned people who love the work, allow them to lean into their strengths, and coach up (or ignore) the weaker parts of their game. 

Sure, we need a certain level of competence—but the idea that we will find the “perfect” person for any given job is unrealistic. This goes for us owners as well. I’m passionate and thoughtful, but I’m no Bob Iger. 

At Cat & Cloud, we’ve gone through different phases of hiring frameworks. In the early years, we exclusively promoted from within. A well-intentioned cultural gesture but we sometimes needed to fill roles for which we didn’t have anyone with even the base level of skill or desire needed. 

So we loosened up the reigns. Here’s what I’ve noticed:

Since giving ourselves permission to hire externally for higher-level positions, in the past three years we’ve only done it once. (Our marketing wizard Micheal Wiser who was also our first guest ever—he’s about as internal as an external hire can get.)

Many gaps can be filled by less than part-time third-party help. (We have someone who helps us work on grocery-specific wholesale who we could never justify bringing on full-time, but has helped us grow in areas where we aren’t experts.)

As we’ve grown as leaders, we’ve become better at clearly communicating expectations to people and identifying good job fits. This has led to us being able to fill most of our positions internally. In the past, I don’t think it was a case of not having the right people but more so us not having strong enough leadership. 

Scars and Scabs

All things being equal (or even slightly unequal), my gut steers towards filling positions from within. There’s something about having someone on staff who is culturally comfortable in your organization and still wants to grow with you despite your scars and scabs. Just as no job candidate is perfect, neither is any organization. Rose-colored glasses and unrealistic expectations can make coming into a small, bootstrapped organization a bit of a shock for outside hires. Plus it’s way more fun to give someone a shot and watch them succeed than to just assume that an outsider with a more “professional” resume will fix all your problems. 

Happy New Year. Happy hiring.