Hiring Employees
A warning: you should be hiring people who are actually curious about the job they're taking. Hirers still don't realize this and hire mismatches constantly.
The best teammates are rabidly curious to devour everything and experiment.
Why is curiosity critical? It doesn't apply to every job, I'll admit, but it applies to many. It's because curious people take advantage of a role to "selfishly" further mastery of their skills.
This is a good thing. In the pursuit of their self-interest, everyone wins.
A curious employee is someone who tests new tools and techniques without being told to do so. They study the competition to learn pick up divergent ideas. They independently read the latest blog posts in the industry to gleam insights.
Because they want to.
Do right by employees by putting them in roles that stoke this curiosity. It not only keeps them and your company on the cutting edge of your field, but it is incredibly infectious for the whole team.
When others see someone actually giving a shit, it reminds them that their own self-mastery matters too.
The net effect is that employees will outgrow their role. Curious employees have growth curves that leapfrog them over non-curious hires very quickly.
Good. Empower them. Getting 2-4 years of a curious person's most enthusiastic effort is a huge win. No one owes you their lifelong journey. And getting just two years with a force of nature does more than most of your employees will do in a lifetime.
Not only that, but curious employees are less likely to quit when the going gets tough: because they're still learning a lot.
And here's the very counterintuitive part about hiring for curiosity: Curiosity is even more important than hiring someone who's "passionate" about your mission. Because passion for a mission fails you when you’re bored out of your mind in your role.
Consider how we’ve all felt that excitement of being part of an important mission only to realize that the day-to-day is so dry we'd rather watch others pursue the mission from afar.
Meanwhile, curiosity empowers people to have inward-facing missions. Sidequests. They don't get as boring.
Now, this is all fine and sensible, but how do you actually figure out whether someone is curious?
Simple. I customize roles to maximize my best candidates' curiosities that overlap with business goals.
Meaning, I ask questions to uncover what they want to learn:
By meeting a candidate's curiosities where they are and not forcing them into a box, you become a much more compelling job for them. This lets you hire talent away from other companies with greater ease.
Now, to assess whether a candidate is curious, I might ask them:
That said, indexing on curiosity doesn’t work for every role.
You want the most experienced—not the most curious—pilot to fly you, for example.
But, in my experience, this philosophy works spectacularly well for early software startups and creative roles in particular.
Why? Because startups and creativity are driven by innovation, experimentation, and resourcefulness, and that requires a team of curious people who are sponges.
Curiosity compels mastery. And its infectious.
Stepping back from curiosity to look at the full picture: when vetting candidates, below are the qualities I personally prioritize.
Finding people with all these qualities is hard. That's why many $1B+ startup founders spend up to half their time on recruiting.
Treat your job description (JD) like a pitch deck that you’d use for fundraising. Do not just write plain JDs requiring “5 years of SQL experience” and “a self-motivated contributor” and expect A+ talent to find your job more interesting than the millions of others available. Here are some ideas:
Here's my final principle for hiring: most great talent is still employed, not searching, and is unlikely to come to you. This means you must go outbound.
I search for great candidates in two ways:
Let’s dive into this process step-by-step.
I source candidates via LinkedIn Sales Navigator (to find people with the appropriate background) or I search my enriched customer base.
Then I message each candidate as the CEO (not a recruiter). The message looks like this:
When I receive a response, I proceed to the next step.
1. I use my first phone call with a candidate to get them excited—not to grill them. They’re often employed, so they hold the cards and I’m the one who needs to sell. When doing so, I’ll get a feel for their personality and whether they’re someone I’d want to work with: Do they provide short, uninspired responses or do they play ball and ask good questions?
2. If we both like the interaction, I’ll ask them to sleep on the opportunity for a couple nights before emailing me their answers to these two questions:
This exercise is necessary to give them peace of mind—because if they’re leaving an employer for you, they're facing financial and career risk.
3. When they respond with their concerns, address those truthfully via email.
4. Do a second call where you ask all your vetting questions. As a reminder, I generally look for people who are curious, intentional, ethical, and resourceful. I also use this second call to see if I can dissuade them from joining by pointing out the sucky things about the role and business. I make sure they understand the tradeoffs so they don’t prematurely quit.
If they pass the calls, I proceed to vetting their talent.
Employers are still very fooled by resumés. I see it with my 100+ startups. The problem with hiring based off past roles and pedigree is that the previous employer likely did the same thing! A chain of zero diligence. So, I use resumés for prioritizing but sample projects for assessing.
I give top candidates a brief paid project to assess their strategic thinking (e.g. prioritization, planning) and the tactical skills needed for the role (e.g. copywriting, data analysis). The project also assesses whether they move fast and get things done.
The projects look like this:
1. To assess their strategic thinking, I have them write out how they’d approach a big problem that arises on the job: How would they scope the problem, reverse engineer it, generate experiments to test their hypotheses, execute those experiments, and act based on the results? I have them map out a decision tree for how they’d proceed based on the different outcomes.
For strategic roles at tech startups, this project is necessary: hires must be deliberate, framework-driven thinkers—not people who reflexively make decisions.
2. To assess a candidate's tactical skills, I pay for a brief deliverable. If they’re making ads, for example, I’ll ask them to make ads for the business. If they’re writing for the blog, they’ll write a sample blog post.
The tactical project also serves to confirm they’re willing to do the work they’re applying for. I’ve had candidates quit during tactical projects, which showed me they were merely being opportunistic and didn’t truly care for the role.
3. Finally, I do reference checks. I try to talk to at least one person who worked above them, beside them, and below them. I ask references to compare the candidate to other folks they’ve worked with in the same position: Is this candidate in the top 10%, 35%, or 50% of folks they’ve worked with?
Most references don't fully divulge negative things about a candidate, so I look for what percentage of references go out of their way to say something amazing about the candidate. That’s a good signal.
My hiring process looks like this:
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