Your First Hire: Finding (and Keeping) the Right Role

When adding the first members to your team, how do you identify the right roles for your needs—and once they join, how do they continue to grow?

When you’re starting up a team, it’s tempting to want to hire a carbon copy of yourself. But you shouldn’t. (Also, you can’t!) As a founder, you probably fill the “visionary” role—the one who sees the big picture and sets the course. So when hiring new employees, do you look for someone who is:

  1. An assistant: They’ll take care of all the details, break work into tasks, and do the “boring” (but very necessary) stuff
  2. A best friend: They “get” you and can save you from yourself
  3. A superstar: Someone with more experience than you who is a fantastic salesperson, known influencer, or stable showrunner
  4. A missionary: As passionate about the space and vision for the company as you are

Matching Roles with Needs

Obviously, you’d love to find “all of the above”— but one person can’t be all those things. And if by chance they were, they’d be out doing their own thing, and you couldn’t afford them. How do you decide? Think about what skills you really, really need to grow the business, and the trade-offs each role brings:


  • Pros: Takes care of the boring details; keeps things moving
  • Cons: May not be able to do more than what they are told; may want more structure (regular hours, established processes, benefits) than you can provide initially

Best Friend

  • Pros: Make you feel great, can think broadly about the business and help save you from yourself when your biases and blind spots get in the way
  • Cons: May not get much done; may want half the business


  • Pros: Gives you credibility and reach; can contribute to strategy 
  • Cons: Expensive; may lose interest if it’s slow going; may compete with you


  • Pros: Lots of energy; can stay with you as you pivot to find product/market fit
  • Cons: Easily frustrated and eventually burned out; may have the same blind spots you have; may not have the skills you need most

As a general rule, if you are a missionary or a visionary who’s not great with follow though, go for high execution–an assistant. If you are already a great executor, consider a superstar who can give you credibility and access. Only get a best friend if they excel at a skillset you lack. 

Job Crafting and Employee Promotion

Even if you’ve narrowed down the role of the person you need to hire, chances are good they’ll excel in some areas and lack in others. As a startup, you need people to be GREAT at their jobs, so don’t be afraid to shift duties around as needed. That’s where job crafting comes in—it’s a negotiation between the employer and the employee to change the job descriptions so that they can do more of what they’re great at, and less of what they’re bad at.

With any luck, your first hire will be so successful that they’ll eventually want to move up. But if you’re still a small team, you may not have anywhere for them to go, or they may not be quite ready for a new role. To keep top performers—and keep them motivated—ask why they want what they want. A lot of the time, people are just bored and want to try something new. If that’s the case, give them “20% time” to work on something they’re interested in that helps the business. For instance, they could help plan an event or give a talk while still keeping their normal duties.

If they are dead set on being a manager, give them a clear set of hoops to jump through that will allow them to audition for the job they want. Make the hoops measurable, and the desired results crystal clear.

  • Bad Goal: Show more executive presence
  • Better Goal: Lead a project to completion on time with an internal NPS rating of at least 8

Lastly, make sure you keep your word—if they do it, reward them with the promotion. In the meantime, titles are free. Make them “Senior” and have them mentor others as training until a role becomes available.

Published July 11, 2019

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