Grinders, sickos, and lunatics.
A field manual to hiring people who get stuff done.
Alright, people of the internet, put on your letter-writing cardigans, we’re talking about hiring.
It is a simple and irrefutable fact that startups are largely faith-based initiatives. And as such they require teams who believe their business can work, and then who’ll work at irrational levels of intensity and persistence to ensure that they do.
And if there’s one company that built its church on the rock of a bunch of deranged lunatics, it would have to have been DoorDash dot com.
Who, though, are these maniacs? These preternaturally effective, effective maniacs? Where does one find them? Why are they so important? Let’s break it down.
They just want to win
No founder’s going to look you in the eye and tell you they don’t want great talent. But then what? Every job posting gets inundated with 1,001 applicants, from new film studies grads to seasoned urban planners to physics PhDs. Your LinkedIn Recruiter account lets you filter for a seemingly infinite number of candidate permutations. There are 8 billion people on this planet. Where do you start?
The first hunting ground, at least in the DoorDash context, was college athletes. These were people who possessed, for reasons unknown and honestly, unimportant, an innate drive to win, no matter what. Division 1 football players, soccer players, baseball players, water polo (they’ll stab ya) players. Anyone who’s had the discipline to practice, train, and work their way into a competitive starting lineup, it turned out, were exceptionally talented operators and collaborative teammates.
Next, veterans. Just like the jocks but replace ‘focus and relentlessness’ with ‘one thousand times more focus and relentlessness.’ That was that squad. In my first year at the company I remember absolutely ruining Thanksgiving Day operations; I’d basically shut restaurants that were open and left open ones that were closed (which you’ll imagine is not what you want to do). And I remember receiving an immediate 8am phone call from our head of ops, an ex-Marine1, from which I got both a dead-calm but very serious list of my immediate action items, as well as a very firm, figurative flick in the forehead for being a moron (valid). Suffice it to say I got that Thanksgiving back on track asap2.
Then you’ve got the fat middle of the distribution: people who have, for one reason or another, a massive chip on their shoulder. People who got cut from their high school basketball team. Middle children. Failed founders. First or second generation immigrants. Ex-management consultants who’d given up the prestige of flying the 5am shuttle from Boston to Chicago 190 weeks in a row to slum it in a silly, early-stage startup. It truly didn’t matter what it was, it just mattered that the person had some unfinished business and was on a mission to prove to the world - and themselves - that they deserved to play in the big leagues.
[One fire subset of the shoulder chip brigade was the number twos. These were people who’d been the number two in a shiny, leading business, but who weren’t getting much time on the field. The VP who could have easily been the Chief Whatever Officer. The senior director reporting to an immovable VP. And so on down the org chart. These people were fully-capable of and dying to show the world they could sit in the big chair.]
And finally, and I’ll just be real, there were the sickos. These people were none of the above. Not athletes, not veterans, not middle children, not number twos. They were just dead-eyed loons who’d work as hard as they could, as much as they could. I don’t know what the deal was with these nuts but I was plenty grateful for them.
I’ll say, for radical transparency, that as much as I would love to share that I was in the high-performance athlete category, I was, in fact, very much on the shoulder-chip squad. I was a twice-rejected applicant to my undergraduate business program, a recipient of an immediate and then near-immediate rejection from Stanford GSB and HBS respectively, and a three-time failed startup leader. None of those experiences sparked a great deal of joy, and I was very excited to rectify as quickly as possible.
Tell me about a time you wanted to slam your hand in a car door
Yes, Steve. Hiring incredible talent is better than hiring idiots. Incredible insight, can’t wait for this Substack to put up a paywall. The question is, of course, how does one go about finding these people? When you rock up to a zoom meeting how do you know whether the pantsless person sitting across from you is your next director or someone you’re gonna be directing straight back to the job market in six months.
Here are a few things DoorDash used to help increase our collective batting average.
There’s an expression in the Marines that “every Marine is, first and foremost, a rifleman.” At DoorDash it was that every manager is, first and foremost, a recruiter. You have 4 outstanding, unfilled headcount? That’s your problem. Applicant funnel starting to back up? Congrats, your Sunday morning is sifting through resumes. Not getting enough good candidates? Stop what you’re doing and start sending some LinkedIn messages. Of course this makes sense, right? Who has more of a vested interest in hiring great people than their future manager?
Second, prize the candidate who’s done hard things. That could be rocking up to elementary school as a first generation immigrant without speaking the language. It could be putting yourself through college by working at a pizza place (or whatever the 2023 equivalent is that also includes insurmountable student debt). It could be you walked to the South Pole to raise money for a good cause. And quite honestly it could be simply that you went to Harvard3 because getting into Harvard is, as I understand it, generally ludicrously hard. What you’re looking for here is someone who’ll grind, who’ll not just do the minimum needed to barely hit their goals, but the maximum to ensure they hit their goals.
Third, always give candidates, from c-suite on down, an analytics exercise or case study, where they have to run some relevant analysis and prepare their findings within a finite amount of time. Why? Well because it’s incredibly $%#*ing annoying, that’s why. I am sure that there are those of you for whom an analytics exercise is an opportunity to gauge a candidate’s analytical toolkit and strategic thinking. Not me. No, I view it as primarily a chance to see whether a candidate wants the job enough to spend 4-6 hours of their evenings and/ or weekends to put together what is ultimately a pretty meaningless product. From that, I can at least conclude that Doug is a hard worker, and that in a crunch, he’ll be the teammate who says “yup, on it”, rather than the one who equivocates, dithers, and stalls.
Fourth, regardless of the questions I ask in an interview, I find myself gravitating to a concept I had never encountered pre-DoorDash, which is content-to-words ratio. Yes, the content of your interviewee’s answers matters, but above that, is their ability to convey their answers succinctly in as few words as possible. It proved an incredible proxy for someone who was a structured thinker, a focused operator, and, someone who’ll make the most of your time together. After all, who do you want to have your 1:1s with, the person who can rattle through 5 dense topics in 30 minutes or the person who’s still trying to get out of the driveway as you’re supposed to be wrapping up.
Finally, for the love of God, just ask them about the job. The internet is littered with Inc. articles with the 99 best interview questions, and they’re all some version of “tell me about a time where you faced an uncertain situation.” Shoot me directly into the sun. An uncertain situation? No kidding, an uncertain situation? What ever did they do in this very exciting and uncertain situation? Well, they either 1. handled it deftly with a balance of focus, skill and action or 2. set their hair on fire and ran screaming into traffic. No, please, I beg you, just try asking questions about the job you’re actually hiring for. “Hey, here’s our problem, what would you do?” You’ll gauge whether they’re actually interested in the work they’ll actually be doing, whether they’re sufficiently qualified for the work such as to provide some novel insights, and hey, maybe you’ll learn something to boot.
Talent starts at the top
Very quickly and simply, Tony Xu ultimately had to approve every DoorDash hire himself as recently as I think 2020. And it wasn’t a rubber stamp, there were real questions. Why is this the best person we can find? How will this person increase our talent bar? How will this person measurably improve the business? Are you going to bet your reputation on this hire? There were honestly a lot of times where under these kinds of questions a candidate at the 1 yard line would be rejected. Where hiring managers would lose their conviction. To be clear, it wasn’t that every candidate needed to get gold stars from every interview, it was simply that at the end of the day the person making the hire had to stand in front of the CEO and pound the table for their person. And it worked.
Once you go sicko, you’ll never go backo
Why does any of this matter?
Well, I’ll tell you (I guess that’s the whole conceit of a Substack).
When you’ve got someone you know you’ve got to fire, that’s kind of easy. It might not be easy to sit in the room and tell them they’ve been let go, but it’s usually not a shock when it happens. Let’s call that the bottom 20%.
Then, you’ve got the next bucket of talent. This is the bucket that we’ll call… ‘fine’. At the upper end they’re dependable operators, at the bottom they’re at best doing no harm. This is the ‘big company’ squad.
And then above both these groups you’ve got what we’ll call, very lovingly, the lunatics. These are the people who you could ask “hey can you fix this?” And by the following week it’d be fixed and there’d be a meeting to review how it’d been fixed. They’d ping you about an idea they’d scoped and launched in secret and that had worked awesomely. They would generally move heaven and earth to accomplish their objectives.
And you know what? They were an absolute transcendental joy to manage and work with. They were the backbone of DoorDash’s operations and ultimately a major - if not the major - reason why that company succeeded. Your prospects as a company are basically directly proportional to the number of these nuts you have inside your tent. So go forth, gather up as many sociopaths as you possibly can and watch your business accelerate into the stratosphere.
Though I understand there’s no such thing as an ex-Marine.
Nah, I’m kidding. It was a dumpster fire, gate to gate.
Harvard College.