Before hiring for a critical function, founders should do the job themselves, even if they aren't experts. The goal isn't mastery, but to deeply understand the role's challenges. This experience is crucial for setting a high hiring bar and being able to accurately assess if a candidate will truly up-level the team.
Related Insights
Contrary to conventional wisdom about delegation, the best management style for a small business founder is to be "all over fucking everything all the time." This means maintaining granular involvement in every aspect of the company—from client happiness to legal spending—to relentlessly drive daily improvements and maintain operational control.
Figma's founder, Dylan Field, admits he was a poor manager initially. His solution was to hire experienced leaders he could learn from directly, like his first director of engineering. This flips the traditional hiring dynamic; instead of hiring subordinates, insecure founders should hire mentors who can teach them essential skills and push the company forward.
Resist hiring quickly after finding traction. Instead, 'hire painfully slowly' and assemble an initial 'MVP Crew' — a small, self-sufficient team with all skills needed to build, market, and sell the product end-to-end. This establishes a core DNA of speed and execution before scaling.
To scale from 100 to 1,000+ employees, you must stop interviewing everyone. Success depends entirely on the cultural foundation built with the first 100 people. By personally hiring and imbuing them with the company's core values, you create a group of leaders who can replicate that culture as the organization expands.
To clarify difficult talent decisions, ask yourself: "Would I enthusiastically rehire this person for this same role today?" This binary question, used at Stripe, bypasses emotional ambiguity and provides a clear signal. A "no" doesn't mean immediate termination, but it mandates that some corrective action must be taken.
For high-level leadership roles, skip hypothetical case studies. Instead, present candidates with your company's actual, current problems. The worst-case scenario is free, high-quality consulting. The best case is finding someone who can not only devise a solution but also implement it, making the interview process far more valuable.
Your internal monologue during hiring reveals if you're making the right choice. If you think, "I really need to fill this role," you're on the path to settling. The right candidate sparks the feeling of, "I don't even care if I have a role for this person, I have to get them in."
Don't be paralyzed by the fear of making a bad hire. View hiring as an educated guess. The real knowledge comes after they've started working. Firing isn't a failure, but the confirmation of a mismatched hypothesis. This reframes hiring from a high-stakes decision to an iterative process of finding the right fit.