Startups and Desert Island Employees

Published on November 21st, 2019

Kevin is a MacGyver-like technologist. During our five years of working together, he had this knack of pulling rabbits out of hats and coming up with solutions and workarounds that blocked others. When describing him, I would tell people that if someone were to drop him off on a deserted island, he'd find a way to build a server by the close of business that day. Now, of course, there was no real way for him to melt sandy beaches into silicon chips. Still, it was more a statement about the overall resourcefulness and tenacity by which he attacked problems.

During our time working side-by-side growing a startup within a startup, Kevin and I interviewed over 200 people for roles ranging from PR, accounting, sales, design, development, etc. Interviewing is a high leverage activity, which means there is a lot of pressure to do it right. A great hire can be a force multiplier for a team or company. The wrong hire can sap resources, morale, and money.

Knowing this, we had to be very thoughtful about what our non-negotiables would be. Doing this allowed us to effectively and efficiently rule out some candidates so that we could focus as much of our effort on the ones that had the highest probability of success. We weren't always right, but I'd like to think we had more successes than mistakes as a result of our processes and criteria.

For me, one of the biggest non-negotiables in a startup is having team members that would thrive in a metaphorical desert island challenge. So how does one make that determination? The following are a useful set of questions to review:

  • Are they resourceful enough to think on their feet? With no directions or hints given to them?
  • Are they creative enough to develop novel solutions? With no previous map?
  • Are they capable of learning new skills on the fly? Even under time pressure?
  • Are they determined enough to persevere through the numerous and enormous setbacks?
  • Are they resilient enough to deal with the inevitable adversity?
  • Are they able to maintain a positive mental attitude and belief in themselves despite their moment to moment circumstances?

And finally... would you have confidence that they would get off the island?

I call people that score high on all these marks, a desert island employee. They are invaluable in a small-yet-growing startup because they can achieve so much in autonomy. Of course, it doesn't mean you have to or even should throw them in the deep end. They often work incredibly well with teams, helping keep people motivated, and finding solutions around roadblocks.

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About Rick Manelius

Quick Stats: CTO of Contact Mapping. Author of Winning the Lottery Within. Graduated from MIT in '03 (BS) and '09 (PhD). Life hacker and peak performance enthusiast. This blog is my experiment in creative writing, self-expression, and sharing what I've learned along my journey. For more information, read my full bio here or contact me.