CEOs provide a curated view of their company's culture. To get an accurate picture, talk to people who have left the organization on good terms for an unfiltered perspective. Also, ask behavioral questions like 'What would you tell a friend to do to be successful here?' to uncover the real cultural DNA.

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.

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.

When management denies your request for a new opportunity, resist the urge to immediately see it as a red flag. First, critically assess your own strategy. Are you communicating in a way your audience understands? Are you trying to skip essential learning steps? Self-correction is often more valuable than immediately leaving.

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.

To elicit candid answers from fund managers, the most effective technique is not the question itself but the silence that follows. Resisting the psychological urge to fill the space forces the manager to sit with the question, often leading to less rehearsed and more truthful responses.

When a defining career ends, the biggest struggle is often existential, not financial. Our culture fuses identity with profession ('what you do is who you are'), creating a vacuum when the job is gone. This leads to profound questions of self-worth, value, and purpose that transcend money.

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.

Standard reference checks yield polite platitudes. To elicit honesty, frame the call around the high stakes for both your company and the candidate. Emphasize that a bad fit hurts the candidate's career and wastes everyone's time. This forces the reference to provide a more candid, risk-assessed answer.