Continually Evolving Thoughts on Talent and Hiring

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In writing this post, I wanted to make a reminder for myself about the continually evolving nature of how I’ve viewed talent and hiring, and how it’s possible that my views will continue to change in the future.

When we first started Barrel, Sei-Wook and I were essentially a couple of freelancers who said yes to enough work that we needed to hire people to help us. We used Craigslist and that was the start of our journey as employers (not counting brief stints by close friends as part-time help). We lucked out as some of our hires turned out to be very talented and instrumental in our growth. In fact, one of our Craigslist pickups is a Partner at Barrel today and one of our best leaders.

The hurdle for hiring back then was fairly low – we were grateful that people with skills would want to work for us, even though we couldn’t afford to pay much. We didn’t screen much for things like professionalism, communication skills, or teamwork. In fact, we lacked such attributes ourselves as we were fairly inexperienced. We were, after all, just hitting our mid-twenties and high on being our own bosses.

Over time, as we began to professionalize and put in more processes, we put in a bit more structure. We interviewed for multiple rounds and did reference checks. Some hires have worked out really well. Others have not. I’ve learned to accept that nobody, even the ones that are amazing as candidates, are a sure bet. Until you’ve worked closely and observed how they perform in a variety of situations, it’s tough to truly gauge how good they’ll be.

However, one thing is certain–when we do hit jackpot on a really great employee, it makes a world of a difference. Nothing improves team morale and business momentum than really talented people doing excellent work. A great hire can instantly bring new energy to the team and elevate the output of the entire company. It’s truly a beautiful thing to see.

We’ve been working hard to mitigate the risk in the hiring bets we make. We’ve introduced a range of skills tests to accompany our interviews. Some of these tests are designed to help us gauge someone’s level of attention to detail, their ability to think on their feet, and their ability to present. I used to think these were too basic, but then I’m reminded of tests that athletes have to do for scouts at pre-draft workouts or for anyone trying out for a spot on the practice squad–they’re often subjected to skills tests that test their fundamentals as well as intangibles like in-game awareness and ability to synthesize information. A while ago, I had written about the fundamentals of knowledge workers, but it took our company a good year before we codified many of these skills into measurable tests in our hiring process.

I don’t think the testing of fundamentals satisfies everything. There’s still a great deal of work to be done to mitigate hiring risk. And it’s also important to not think of hiring solely from a risk perspective–then it’s too much of a focus on downside and not enough on potential. This is where outbound recruitment, scouting, and junior talent becomes important to an organization. Rather than solely relying on inbound applications to hopefully find our next gem of a candidate, it’s critical that we build infrastructure to proactively recruit and find talent that will represent upgrades for our team.

This could come in the form of working with an outside recruiter for specific roles or building our own in-house recruiting practice to identify and go after talent at other firms. I used to be allergic to the idea of paying recruiters, but knowing the impact that a great hire can make to the culture as well as the bottom line, I think recruitment is a very worthwhile investment. It’s no different than building up a very strong new business pipeline–when you have a strong talent pipeline, the chances of landing the next difference-maker will go up. This practice extends not only to proactively going after talented people looking to move laterally to our company, but also in building up a very strong “farm league” of junior talent.

I’m inspired by the Core Four, the legendary Yankees players (Jeter, Pettitte, Posada, and Rivera) that were signed as amateurs by the Yankees in the early 90s, developed in their minor league system, and eventually became the foundation of the dynasty that yielded five World Series Championships for the franchise. I love the idea of having a robust system of young talent–interns and juniors–who join us right out of school or not too far removed from it, and eventually emerge as superstars. The challenge for us has been the perceived overhead and required investment in overseeing such talent development. Oftentimes, we convince ourselves that it’s easier to hire someone “more experienced” and forgo the work required in nurturing talent. However, I think this line of thinking comes from being reactive to resourcing challenges and focusing too much on solving a short-term problem. If we’re to develop a truly valuable system, it means investing in interns and juniors and bringing them up in a way that allows them to make mistakes and learn. It also means being open to having a good number of such employees at once, which then means freeing up the time of seniors and managers to ensure they can provide guidance.

None of this is easy or without some trade-offs. If I was to succinctly summarize my evolving stance on talent and hiring that I’ve sketched out above, it’d be this: invest in reaching more talent; push through a greater volume of talent through our qualification process; invest in building a hiring and talent development framework that will ensure that the strongest and most impactful employees are selected and nurtured. Let’s see how this holds in the coming months and years.


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