Hire leaders with at least one 5+ year run

My favorite Silicon Valley truism is: The team you build is the company you build. (Credit to Vinod Khosla.) Very soon after founding, most of the work at the company will be done by people who are not you. You will succeed or fail based on the quality of their work. You have lots of levers of influence over the quality of that work, but far and away the biggest one is who you choose. Especially which leaders you choose. 

I’ve made more bad leadership hires than I care to admit. Chief among my mistakes was hiring for the resume when I knew in my gut it was a bad fit. The dopamine hit of showing the board and the early team that you hired someone with a big title out of Nvidia or Salesforce is real, and it comes back to bite you every time. Rushing a seemingly-good candidate to “yes” without doing all my diligence is another shameful repeat offender for me. That one’s always fun later when the board asks you why something didn’t come out in the reference call and you get to admit you skipped that part.

The main thing I have to show for these lumps and bruises is a hard-learned process. How I do it now, and what I look for:

Hire leaders with at least one 5+ year run. This is my number one. I don’t even care if the company ended up working out. Just that they dug in and gave it 110% over a sustained period of time. First, obviously, there’s a class of Silicon Valley exec that hops every couple years their whole career, and you want to avoid those. Also, any 5+ year run will include tough years and WFIO moments, and the fact that they stuck it out is critical evidence that they don’t quit when it gets hard. Most importantly, during a long run, they played many roles, lived with the long-term consequences of their decisions, drove success but also owned big L’s, got promoted but also got passed over, had to change strategies and try again. This is the real experience. You don’t get it in a 2-3 year “tour of duty.”

Meet three A+, out-of-your-league functional leaders to see what greatness looks like. If you’re a devtools company hiring a marketing leader, meet the CMOs of Stripe and GitHub. This is common advice in the industry. It works. Part of scaling as a founder is hiring for roles you’ve never met and couldn’t do yourself. There’s no replacement for in-person research to familiarize yourself with greatness and inoculate yourself against mediocrity.

Hires from your network have pros and cons, but on balance they’re worth it. 100% of people at Modelbit used to work at Periscope. This has drawbacks. It can lead to a monoculture with blind spots, and it’s going to be very hard to hire and onboard the first non-former-Periscoper. But no matter how strong your process, you will inevitably make a lot of bad hires that you will have to correct. It’s just very hard to know if someone you’ve never worked with will succeed at your company. If you know someone great for the role, and you’re lucky enough that they’d want to work with you again, 9 times out of 10 just hire them.

Do extensive backchannel references. LPs are incredible at these, and VCs do a good job too. For some reason founders are usually weak here. I think it’s because we live and die in “run fast, decide now” mode. I can’t tell you how many calls I’ve gotten about folks I wouldn’t necessarily hire again where the hiring manager has clearly decided to hire and just wants to say that they called me. It’s sobering, and it’s a good reminder to do a lot of calls and approach each one with an open mind and without prejudgment. 

Listen hard for “lightly positive” references. Usually when someone doesn’t work out for job performance reasons, no one wants to add insult to injury by being a negative reference for their future job searches. So those candidates get a lot of “lightly positive” references. A lot of “they were a solid A-/B+” or “they were a fine team player” or “well, they weren’t the right fit for us, but I think they’d be a great fit for you.” These comments don’t have to be disqualifying on their own. But if most or all the calls sound like this, it’s not going to be a good hire.

The interview is about what kind of human they are, and whether you can communicate with them. As a rule, executives are pretty polished and interview well. You’ll learn more about whether they’ll succeed at the job from track record and reference calls. Use the interview to determine if this is a human you can work with – and a human you want to work with. The creative director who comes in dressed like a fashion model and whips out a Steve Jobs-style deck would likely be successful at the next Nike or Apple. But it’s a persona I personally have a hard time communicating with. So that candidate is a pass for me, but maybe not for you. Are you comfortable with someone who’s basically motivated by money and doesn’t give a shit about the mission? What about someone who’s made their money and just wants to spend the rest of their career at exciting startups? You want to leave the interviews feeling like you understand what makes them tick, and you’re comfortable with what you learned.

The right answer is “it depends.” I ask VPs of Eng what they do when the VP Sales needs a questionable off-roadmap feature to make the quarter. I ask VPs of Sales what goals they like to see a VP Marketing take, and CFOs whether they’ll go over budget for a chance of hitting the topline. The mark of inexperience is rigid or formulaic answers to these questions. The answer is not “never” or “always.” Candidates who’ve lived these decisions know it’s always messy and the outcome is never guaranteed, but they also know there are moments where you have to take these risks. A good candidate says “it depends” and then talks about how they’d think through the decision.

Accept no bullshit. Bullshit is common in mediocre sales and marketing candidates, and first-time technical founders often think it’s just part of the job. It is not. The best leaders speak simply and directly, and know their business cold. You’ll see this when you meet the A+ out-of-your-league leaders. (You took the time to do that, right?)

Board referrals are often favors to someone else. On the other end of a board referral is often a board member smoothing a termination at another portfolio company by offering to introduce them to new opportunities. Or placing an Associate/Principal at a portfolio company when they’re not going to make Partner. Or making up for referring the candidate to a previous opportunity that didn’t work out. None of these things are necessarily bad, and a good board member will be straight-up with you about all of it. But make sure to ask for the whole story, so you can understand what it means about the context and enthusiasm of the recommendation.

Retained recruiters just want to get the hire done ASAP. They fundamentally do not care about whether it’s a high-quality candidate or a good fit, no matter what the contract says about redoing the search for free. The recruiter will have a roster of people they’ve talked to recently for this job title, and they will push them on you with a half-assed story of how they proactively identified this person for your opportunity. Retained searches can be the right approach, but you’ll need to actively manage them. This means doing your own LinkedIn searches, sending the profiles to the recruiter insisting they call those specific people and report back, and holding them accountable for adjusting to your feedback on candidates.

The biggest risk is the feeling that you must fill this role right away. This usually happens after an unexpected departure. You might have no one who can do what the departing leader did, so you’re in acute pain until you get someone in the seat. You might also feel the board watching you to see whether you’re really able to hire and retain strong leaders in these roles. But the death spiral starts with making a bad hire quickly. Then they do a lot of damage in the months until you move on from them, and now everything is worse and more urgent. You need to put the company in a position where you have a few months to do this right. That might mean some compromises on interim promotions, external advisers stepping in, or just doing less as a company. None of this is great. But I promise the death spiral is worse.

So much of startups is about making quick calls from your gut. Seeing an opportunity and going all-in before you lose the chance. Founders get used to this, and then get tripped up by exec hiring, which rewards thoughtfulness and thoroughness. A bad hire is much worse than another quarter with no hire. Design a good process, take your time, and be sure you’re getting someone great.