Finding the right team for a startup is hard. You are often facing a tradeoff between limited resources (cash and equity, which themselves can have different values to different people) while looking for people who not only meet your current needs but your future plans. And for many key roles, once you find those people, you have to compete for them: most active startup cities are busy places, with many good ideas for the talented to pick from.
So what do you do when you can’t find what you need? You grow it. I think my friend Max Shron makes this point nicely in this DataGotham talk on finding a data scientist: for many startup positions that are not exact maps to other fields (like software development, design, marketing, etc.), you cannot expect to find someone who has all of the skills simply because the field itself is too new. And even for fields that are established, in a small market or a competitive market (which essentially covers all markets at this point), you may have to accept a less experienced hire.
As any good farmer knows, some seeds are better for growing than others. If you know that you are hiring based on growth potential, some of your search patterns need to change. For one, make the explicit choice to privilege personality over experience. Too often, I watch entrepreneurs acknowledge that they are going to need to grow someone into a role, and then concentrate on resume and experience-level as a way of deciding who to interview. If you know this is a growth role, personality is the single most important variable in your hiring process. Look for good cover letters that are personal and personable, and refer to resumes only as an indication of variety and intent.
The interview is also different for a growth role. Instead of trying to understand their experience, you want to understand their motivation, both level and direction. To understand skills, ask questions that focus on the future, rather than the past: what do they want to learn how to do, how do they want to grow the role, how do they see that growth contributing to the business. Don’t bother asking about their desired reward: plenty of people have said they are not motivated by money, and then discovered their own sensitivity to it around acquisition time. Instead, try to get at motivation by asking them why they want to work at a startup instead of a larger company. If they’re going to have to reach every single day in order to do a job they may not really be qualified for, they better know why they are there.
Generally speaking, I’m not a fan of having people solve problems in interviews, but growth is synonymous with the need to find novel ways to solve problems when you don’t always have all the skills already. Try to get at who they would ask when the autodidactic approach fails. Growing someone can truly sap all of your energy if you become the gateway through which they find all information. You want to know that they understand the organization of a startup and the skills that people throughout the community can teach them. Especially if you’re in NYC, where people are often far more willing to help than in The Valley.
In the end, look for someone who reminds you of yourself. While senior employees often need to be differentiated so that they can provide different viewpoints, chances are that if you’re running a startup, you yourself are the kind of person who expands to fill the needs of a role. If the candidate feels like they could be your younger sibling, you’ll probably in good shape. Trust your gut!