How to hire low experience, high potential people

Finding diamonds in the rough

Lee Krasner, Gaea, 1966

My life has been deeply inflected by people who went out of their way to take a bet on me. They saw some sort of potential and gave me the chance to prove myself. 

It was particularly hard to take that bet when I was 19-20 and looking for a life path. I had no skills to speak of, didn’t understand how to navigate the system, and was hopelessly naive. I had applied for hundreds of jobs and didn’t get interviews at the vast majority of companies. I had no idea how to prepare for interviews or even what kind of path I wanted to follow within the industry. But when I applied to the Thiel Fellowship, I finally found people who wanted to take a bet on my potential. I was given a chance to join a team of peers that were similarly green, and found people who ended up becoming the bar raisers, confidants, and inspirations for my career ever since.  

It might seem insane to take a bet on inexperienced people, especially in the context of our current layoff-heavy market. I certainly don’t suggest populating an entire startup with this type of person. But every great high growth company (assume a not-yet-public tech startup) needs at least some high potential and unconventional people. Transformative companies need people to 1) do something crazy, time consuming, and novel without the burden of too much past experience and yet 2) have enough wisdom and experience to distinguish the special sauce of the business from the actually destructive craziness. It’s easier to find and evaluate the experienced folks who can do the latter thing. It’s almost impossible to find the right inexperienced ones to do the former, who are inventive and original and yet also disciplined. They don’t have any obvious past experience that helps you figure out how special they are.

After 1000+ hours of interviewing candidates, making many mistakes in hiring and firing, and closely imitating the best possible behaviors of my “hiring savant” managers, this is what I’ve learned about separating the wheat from the chaff in order to find amazing yet unconventional people.

Someone told me that a great way to run a startup is to have a “COO for every visionary.” This set of learnings works especially well for finding people who can be those “COOs” — people who are 1-8 years out of school, no specific skills (not engineers nor salespeople, yet), who have generalist proclivities. It ignores the “status markers” like school brand names and fancy connections that sometimes feel like red herrings. And of course, once you get one of these diamonds in the rough within your company, get ready to provide them with lots of mentorship – they’re truly a lot of work to polish, but the best of them make it all worth it.

A guide to finding diamonds in the rough

1. Find out their wins above replacement. Through the stories they tell, look to see if the end result of the thing they did would have been significantly worse without their involvement. Try to separate their actions from those of their team or the circumstance. This quality should both highlight their talents and their sense of agency and individuality. 

   1. What you’re looking for: 

      1. Creativity in identifying the bigger problem/opportunity at hand vs. e.g. “taking orders from boss”

      2. Resourcefulness & follow-through. Most smart people are actually terrible at having the drive/follow through to take things to completion. They’ll usually want to give up at the first sign of failure or slowness. It should feel like this person single handedly dragged [thing] to the finish line despite the environment. 

   2. What to ask: 

      1. I really like questions with maximalist qualifiers like "tell me about your best X.” If it's not good, you know that their best isn't good enough.

2. Navigate the world on their own terms. The best high potential youth are often unconventional in some ways. And if you’re looking for someone unconventional and high potential, they’ll often have a rationale for their unconventional approach.  Ideally they can describe their weird path in an internally coherent way without being egotistical or defensive. 

   1. What you’re looking for: 

      1. A thoughtful vision for their future that indicates some level of originality, broken down into specific life choices. Don’t expect this to be polished, you should employ some amount of “spidey senses” to glean what they really mean.  

   2. What to ask: 

      1. “Tell me about you. If your life was a book, give me the chapter titles from your birth till now.” Once you’ve gotten the overview, dive into each “chapter” and plumb the depths for their real stories. Go back to their childhood! I learn a lot about their grit and commitment to excellence from their basketball obsession or maybe their experience caring for a sick relative. People who have conquered adversity are extra valuable.  

3. Determine if they have a chip on their shoulder. Do they have something to prove? Where’s the hole they’re looking to fill? Ideally, you’d get someone with obvious talent/drive that is misunderstood by the world. Those types of people will run through walls to reconcile their internal view of themselves with external perception. 

   1. What you’re looking for: 

      1. A sense of security. You need to be careful to ensure they have a chip on their shoulder, but aren’t pathologically insecure! This is one of the biggest mistakes I’ve made in the past – I found someone young, hungry, and wildly talented. However, they were also deeply insecure about their choices and prone to bouts of indecision and paralysis that crippled them. 

      2. Look for positivity. If left to fester for too long, a belief that you’re underestimated can become a toxic trait. They should show optimism and reflect positively on their past experiences while still seeming hungry. If you’re worried about negativity in the interview, know that it will only get worse over time. 

   2. What to ask: 

      1. Match their energy level, bias towards enthusiasm and high energy to start. They’ll be more willing to open up and share what matters to them when they feel comfortable. Echo what they heard back to them, and of course relate it back to your own motivations in a way that resonates with that person — “this also resonates with me — that’s why I did X too <give example>” You get to the “chips” on the shoulder when they’re comfortable with you. 

      2. Highlight challenges and watch how they react. Point out things that could be better about your company that could be in scope for their role  — great people are excited by the challenge, not by everything being perfect. It’s a balance: you don’t want to suggest everything’s terrible, but people want to feel impactful. See if they seem undaunted, if they’re excited by the chance to prove themselves.  

4. High EQ + Persuasion. People who have a clear-headed view of a situation, and the soft skills/influence chops to bend the environment to their will, are especially valuable. It’s an underrated skill. 

   1. What to look for: 

      1. “Game recognize game” – it’s all intuition. It’s the feeling that you’re engaged and enjoying the conversation with the person, but you can see the gears moving in their heads as they read the room. 

   2. What to ask: 

      1. See how they react with multiple people in the room and how they tailor their words. Review their responses in the “debrief” after the interview with multiple people. 

5. Theory for excellence. "Excellence" is a surprisingly generalizable skill. People who've been great at *anything* are more likely to have the drive and self-discipline to excel even at something unrelated. In 2015-era Stripe, we hired a number of ex-Juilliard musicians with no engineering experience with the assumption that “people who know how to be meticulous and practice like crazy can figure anything out.” 

   1. What to look for: 

      1. Examples of past excellence. Did they play D-1 college basketball? Did they play the bass at Julliard? Are they a champion puzzler? Did they design the art for a Dungeons and Dragons card? Excellence is a broad thing, but you know it when you see it! Make sure that you distinguish between “excellence” and “popularity” – excellence does not mean having 100k followers on Twitter! 

      2. Theory of their own competence: Know what they’re good and bad at, what they conceive of as their strengths. They should already be aware of what tools they gravitate towards and what they over-use. Even 20 year olds should know this.

      3. “Spike potential.” In an interview, I’ll attempt to build a mental picture of the person based on their area of competence, and then start to tailor my questions to that specific profile. For example, if I’ve found an ex-Juilliard harpist who seems like she’d be detail-oriented and meticulous, I’ll then ask myself what the best version of that profile might look like. Since that profile usually spikes really high on “getting shit done” and “execution”, I will start thinking about how to probe into that in particular to search for seeds of future excellence in that regard.

   2.  What to ask: 

      1. You can be direct with these questions, and they’ll vary according to the person’s profile. 

6. Openness. You are not hiring a finished product, and therefore want to ensure the person is open to improvement and new ideas. 

   1. What to look for: 

      1. Coachability: This trait has two aspects: responding well to feedback, and being self-aware enough to assess their own performance. 

      2. Disagree and commit: Can they get out of their own ego and move forward, willingly, even when they don’t agree with the plan? 

   2. What to ask: 

      1. If you can’t probe this via their past experience in life, the scenario/case study is the best way to assess this quality. Have them work on a group interview, a take home exercise, or a role-play. Carefully observe how they react. 

      2. Backchannel and references are also excellent here. 

7. People who don’t take themselves too seriously. They have to be able to laugh at themselves to succeed. 

   1. What to look for: This is usually very easy to assess, but look for someone unpretentious and a pleasure to be around.

   2. What to ask: You know it when you see it.