Most people still don't know how to hire. Cutting to the chase: curiosity and the ability to learn quickly are the two most important for strategic startup hires.
In tech startups, great employees are the most powerful form of leverage. To beat competition and remain relevant in your market, you must delegate to people who are strategically competent—because they're curious and learn quickly.
That's what this lesson explores. I'll then walk step-by-step through pitching top talent to leave their job and join your startup.
Hire curious people. Curious people take advantage of your role to selfishly further their own mastery. This is a good thing because in their pursuit of self-growth, your team benefits immensely:
Curious employees are also the ones who test new tools, explore the competition, and read the latest industry blog posts. Because they want to.
In fact, curiosity to master a role is even more important than having passion for the company's mission. Because passion for the company fails you when you’re bored out of your mind.
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 just watch others pursue the mission for us from afar.
That's why leveraging a candidate's curiosity is also the most effective way to poach talent from big companies—to join your little-known team. To do this, customize roles to maximize top candidates' curiosities. I ask them questions to uncover what they most want to learn:
Even if their mastery of new skills is in pursuit of them later leaving the company to start their own non-competitor, that's fine! Getting 2-4 years of a curious person's most enthusiastic effort is a huge win. And they don't owe you their lifelong efforts.
To assess whether a candidate is curious, I might ask:
By meeting a candidate's curiosities where they are and not forcing them into a box, you become a much more compelling opportunity for them.
That said, indexing on curiosity doesn’t work for every role. You want the most experienced pilot to fly you, for example, but this philosophy works spectacularly well for early software startups and creative roles.
Why? Because startups are driven by innovation, experimentation, and resourcefulness, and that requires a team of curious people who are sponges.
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.
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: