Hiring uncomfortably

A startup founder and I were recently discussing the topic of early-stage hiring. Since assembling a capable team is perhaps the single most important thing an early-stage startup CEO will do in building a business, the hiring strategy employed will play a significant role in the outcome. As anyone who has worked in an early stage startup knows, the people inside a company — particularly the earliest employees — do much more than build and sell a product. They also:

  • form the basis for a company culture and standards of excellence
  • establish process for key strategic decision-making, including how ideas are challenged and debated internally
  • influence how information is processed and shared within the organization
  • set the tone and role that ethics play in day-to-day business activity
  • ultimately, all of the above informs how future hires are made

This founder made the comment that he believes in “hiring uncomfortably”. Though we didn't get into what he specifically meant, I remember nodding our heads in mutual agreement. Hiring uncomfortably in the early days of a company's life means hiring the best and brightest people you can find for a given role, raising the bar of effectiveness for the entire organization. In addition to possessing relevant expertise in their specific areas of focus, the best early employees are “athletic” meaning they are well-rounded generalists who can play many different positions on the court. Over time, as companies grow, the need for generalists shifts to a need for specialists, but in the early days, athleticism matters. Hiring uncomfortably means hiring people who may know more than you about certain areas of the business and letting go enough to let them run once they're on the team.

A trap that I see some founder/CEOs falling into is hiring early employees who have reasonably good specialty skills, but aren’t athletic enough to adapt to the ups and downs of an early stage business and are probably not the very best person they could have found for the role. There are many possible reasons for CEOs to fall into this trap, but an obvious one is a self-preservation bias — not wanting to risk hiring their own replacement. For obvious reasons, this is short-sighted, yet it’s something that we see happen all the time. Self preservation, while a natural human instinct and often subconscious, is generally in direct opposition to strategic and opportunistic hiring. If CEOs have a clear picture of their strengths and areas of highest value add to their business, they are likely to be more comfortable hiring exceptional people to complement those areas. Conversely, CEOs who lack focus and try to exert too much control over the organization broadly speaking may not hire as well.

Mike Lazerow and I discussed this concept last spring in the context of a company we both know who was considering recruiting someone for the president role. He commented to me that he believed in hiring presidents "as often as possible", and specifically hired three President-types at Buddy Media. Hiring uncomfortably means possessing the confidence to surround yourself with people who can teach you things and bring unique perspectives that makes the broader organization stronger. Sometimes, it means hiring someone who may, one day, be better suited to run the business than you. Not every business leader possesses a level of confidence and awareness to hire uncomfortably, but the ones that do will position their companies best to maximize opportunity for success.

Update: Ben Sun wrote a great post on this topic from the entrepeneur's perspective last year. As I was reading it, I remembered he was the entrepreneur who inspired this post, so giving him due credit.

By Josh Guttman

Website