Hiring - The Big Picture

Growing Pains

My first encounter with startup hiring was a rude awakening. First company I ever co-founded. First time manager. First time hiring an engineer who would be reporting to me. None of us had expectations of this attempt being a home run, but we figured it would be “just fine.” How hard could it be after all? It goes about as well as you would expect.

The candidate, Steve, and I perform an interview rain dance that neither of us are familiar with. Steve is about as green as I, applying for his second job after college. After a brief chat I send him a take-home test I had to slap together the day before. Later, a few standard interview questions scrounged from a Google search. A whole lot of open-ended chatting about programming opinions. I don’t know anybody who has done this before for a startup and asking ChatGPT is still in a galaxy far far away.

In the end neither side learns much about the other, but we’re not exactly swimming in options. He’s only talking to one firm. We’re talking to a few candidates, and he seems “reasonable,” a word that is always a strong telltale. It’s worth a shot, I guess. Part of me hopes I absolutely nailed it, maybe I’m secretly a genius and this hire will prove it. Two months have passed. I have to deliver Steve the bad news in a spartan and dimly lit 3-person conference room that still lives in my head 12 years later. It looks like a broom closet. It actually might be one. The office space owner figured a desk and two chairs (my cofounder had to stand during the announcement) count as a conference room. You can touch both walls if you stretch your arms out. Steve is shocked to hear the news, because, of course, I failed to make it obvious to him this whole time that he was doing poorly. My naive first-time manager self hoped he would get the message somehow if only I gently hinted at it. It wouldn’t be the last time I bomb finding the right person for the team and have to walk someone to the elevator with all of their stuff. Yikes.

Ever since that experience, and many variations of it since, I’ve been tormented by the quest for the perfect hiring process, and why some companies absolutely nail this, and others half-ass it at best. Perfect not in an abstract global optimum sense, but perfect for my company, its industry, its life stage, its people, its tribal customs. I dread letting people go, and I never want another Steve on my hands. I should have known better, been better. What was missing?

That quest is still ongoing, mistakes still happen, but what I do today hardly resembles the first fumbled attempt from 2013. After tens of thousands of resumes and hundreds of interviews, every hiring push I lead offers more opportunities for valuable scars and iteration. And now I approach the process of building one’s hiring flywheel with the same lens of experimentation and rigor as with any other product I build, be that internal or external.

Impossible Tradeoffs

Hiring at a fast-paced startup is all about impossible tradeoffs. You need the perfect hire, yesterday. The team is drowning. The runway is getting shorter by the day. A hiring mistake? You might have killed the company. You delay hiring for a few months? The mountain of work only gets more desperate, and the runway is ever shrinking. You still might have killed the company. As you get bigger the price of every individual mistake goes down, but accumulating many of them leads to a very painful fix down the line.

Every firm must pick their poison. Don’t know who you are, your culture, the role? Wrong hire. Spend forever trying to figure it out, avoiding mistakes? The market might run away from under you. Skip steps, rushing the funnel? You’ll make bad hires. Drag things on? You’ll lose good ones. Your sweet spot depends on a dozen variables: risk tolerance, culture, market conditions, desperation level, the list is vast. And these variables constantly move. What worked during your Seed will crater you at Series B. Last year’s artisanal process is this year’s hyper-scaling bottleneck.

If that wasn’t enough, you have to do it all on a shoestring budget. You might be in Cockroach Mode, and the market might be such that a great hire is already being paid more than your entire pre-seed round. You might have to alter the nature of your company to survive Hiring Winter, potentially hiring abroad and working asynchronously to make it all work.

It’s hard, but it’s also one of the most important areas for you to invest in. It’s so important that some have called it the “other product,” beyond the product you’re actively selling to customers, and my thesis is that you need to treat it with an equal amount of reverence.

Assembling Two Airplanes on the Way Down

Your company’s hiring identity, its positioning, its funnel and the post-hiring follow-up is an essential part of the broader product-market fit search. What most first-time entrepreneurs don’t appreciate is that the product is not actually the only product you’re building. The company itself is to be marketed and sold to a specific niche of potential future hires, with its own narrative, differentiation, aesthetic packaging, and a promise of a better life after the “purchase.”

You have to come up with a thesis of what would be best for your team at this point within your budget and available time, and how you’re going to go about obtaining it. You then proceed to test those assumptions by iterating on the process and the type of person you’re looking for. Whether you succeed or fail with each iteration, you learn something valuable about yourself, the company, and the market. Just like user onboarding, you keep iterating on this for the rest of your company’s life, as the target will be constantly moving.

Reality check: there’s no perfect playbook. Early in your career you hope that there’s a universal formula that you can spam at your hiring problems. With much trial and error–mostly error–you realize that every solution has to be bespoke to your situation. Past lessons are key, but only if you know when to break them for your unique situation. The good news is that any company that has become great at consistently sourcing, attracting, closing and retaining stellar employees has had to figure this out. The playbooks exist and you don’t need to re-invent the wheel. The bad news is that the playbook still needs to be adapted to your own unique circumstances, you can’t carbon copy another company’s essence and expect it to work. You test and test again.

If you run enough of these experiments, with plenty of reflection and course-adjustment, you will get pretty darn close to where you hope to land. You will make mistakes, the only way to avoid them is to never hire to begin with, but eventually you’ll dial things in. At least until it stops working, and then you do it all over again, an important but ultimately Sisyphean endeavor.

The More Things Change

Your gate into the world of early stage hiring is going to be through founding the company or by joining it at a later stage with a mandate to fix whatever has been cobbled together until that point.

The team you’re joining might be 2012 Alex and a homebrew process duct-taped together from whatever fads were hot and trending on Hacker News that year. We were chasing holacratic coding ninjas, then radically candid 10x engineers, then founder-mode cracked 996 Claude-riding context wranglers. Here, your work is going to involve undoing a lot of unfounded assumptions and letting go of those unfortunate enough to have gotten reeled into the company without much rigor. If you’re lucky, they might be great and get to stay. But chances are you’re going to have to rebuild a chunk of the team, or you wouldn’t have been brought in to intervene.

Fortunately the art and science of doing this right is nowhere near as mysterious and opaque as it might have been decades ago. Unfortunately not everything from past eras is going to carry over. Take home projects are blown away by a single prompt of ChatGPT. Spies with gen-AI Zoom faces apply for tech jobs to siphon VC funds for sketchy foreign regimes. H-1Bs cost 100 grand to obtain. Cluely-style cheating apps answer every interview question. $100M comp for the top AI talent.

We’re living in a wacky timeline and many tactics from the past have gone the way of the dinosaur.

Luckily the fundamentals haven’t changed much, as are still very much worth testing for. What also hasn’t changed is the hiring cat and mouse game, and doing the job well requires staying on top of the relentless stream of changes. Part of what keeps things interesting, I suppose, if you want to find a silver lining in it all.

Next up, a look into how to position your team in the relentless cacophony of a hectic hiring market.