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.

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Challenge the 'hire slow' mantra. Hiring is an intuitive guess, so act quickly. Once a person is in the organization, their performance is a known fact, not a guess. This clarity allows for faster decisions—both in removing underperformers and, crucially, in accelerating the promotion of superstars ahead of standard review cycles.

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.

Terminating an employee shouldn't be viewed solely as a negative outcome. Often, a lack of success is due to a mismatch in chemistry, timing, or culture. Parting ways can be a necessary catalyst that enables the individual to find a different environment where their skills allow them to thrive, benefiting both parties in the long run.

Firing decisions should be a function of both incompetence and business constraint. Not all underperformers are equal priorities. Some are like a "trash can on fire in the driveway"—a problem, but not the company's main bottleneck. Focus firing efforts on roles that are the direct constraint to growth.

To scale hiring efficiently, eliminate ambiguity. Each interviewer must make a definitive 'yes' or 'no' decision. If an interviewer is 'not sure' after their session, they are the problem, not the candidate. This prevents endless interview loops and forces clear, decisive judgment.

When confronting a high-performing but abrasive employee, don't just criticize. Frame the conversation around their career. Offer a choice: remain a great individual contributor, or learn the interpersonal skills needed for a broader leadership role, with your help.

Firing someone feels adversarial until you reframe it as a win-win. The employee wants to be successful and valued; if your team isn't the right place for that, helping them move on is a service to their career, not a disservice. This mindset changes the entire dynamic.

Employee retention now requires a customized approach beyond generic financial incentives. Effective managers must identify whether an individual is driven by work-life balance, ego-gratifying titles, or money, and then transparently tailor their role and its associated trade-offs to that primary motivator.

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.