A Talent for Extreme Uncertainty

This is “Part 1” of a series on hiring excellent talent.

Business writers will tell you that the key to success is getting the right people on the team. Get the right people in the right seats on the bus and all that. (Aside: the seats on a bus are pretty much all the same so this metaphor doesn’t really make sense.) Go to any workshop or tech event and you’ll hear the same idea over and over.

But Daniel Pink says that there’s a gap between what science knows and business does. Why? Because nobody boos a pro-people stance. When you’re on a panel talking about running an organization and throw out some platitudes like “it’s the people that make us what we are,” no audience member will shout out “BUT DO THEY HAVE FIVE TO SEVEN YEARS OF EXPERIENCE?!?

Building a team is about leverage and risk. Can the person you bring on provide more value than they consume? When they do, that’s leverage. If that value is delivered by making others on the team more efficient/effective then you have something special. But there’s risk — what if they don’t work out? Slow other people down? Can’t deliver on their commitments? The game is to build leverage without excessive risk.

We can see that hiring is a flawed process. Especially in tech, our hiring processes reinforce the status quo.

We have six people. We need one more. Get me one just like the ones we’ve got.

How does that job posting get drafted? The person in charge of hiring probably isn’t technical, so they have to ask questions of the developers. “What skills do you use to do your job?” But the average developer doesn’t understand what makes them effective. Instead of trying to figure out what a “right person” might be like, we vomit out a bullet list of technologies we happen to be using at this moment. And top it off with a made-up number of years we think it takes to become a “real developer.” Look at any technical job listing and that’s what you’ll see.

It’s the process here that’s flawed, not the intention. These people are trying to mitigate risk. HR’s job, at the core, is to provide safety to the company and employees (in that order). HR will gladly forego leverage to minimize risk because risk is antithetical to their purpose. They’re just doing their job. Meanwhile the developers just want to get back to writing software, so they’re regurgitating what they’ve seen in job listings and recruiter emails.

What’s the consequence? We have an industry that prides itself in “disrupting” everything but faces a talent shortage. There’s nothing a technologist loves more than going into another industry and telling them what they’re doing wrong — but look in the mirror and we’d see the same stupid decisions hindering our own progress.

My friend John Dowd, a former Navy SEAL, told me that SEALs are “trained to make life-or-death decisions in situations of extreme uncertainty.” The average company is not nearly as dangerous or important as the work those amazing people do, but the idea is powerful. Life-or-death and extreme uncertainty catch the ear, but the most important word is trained.

People can be trained; people can learn how to deal with uncertainty. The talent we need isn’t the person who’s solved today’s problem before — it’s the person with enough knowledge, skill, humility, and insight to solve it anew.

The number of years you’ve been solving problems like these does not indicate your skill at solving the next problem. Having dealt with similar situations before is valuable — unless your analysis becomes so simplified that you believe the new problem is the same as the old problem. History and experience give us clues, not a roadmap. In any kind of engineering, executing a plan now based solely on what was observed last time is foolish. The best problem solvers leverage their knowledge and experience, but combine it with fresh perspective and information — recognizing that while few situations are truly new, few are truly identical.

How do you find those people? Invite them to find you. “Part 2” of the series is Let Them Write Code.


Jeff Casimir is the Founder & Executive Director of Turing School of Software & Design. He cooks up enough ideas to make any situation feel like extreme uncertainty.