Zipline's CEO shares advice from board member Alfred Lin: fire someone the first time you consider it. The logic is that for true A+ players, the thought never crosses your mind. Debating whether someone is a C- or C+ performer is a poor use of a leader's time and energy.

Leaders struggling with firing decisions should reframe the act as a protective measure for the entire organization. By failing to remove an underperformer or poor cultural fit, a leader is letting one person jeopardize the careers and work environment of everyone else on the team.

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 manage stakeholder expectations and create predictable workflows, collaboratively create Service Level Agreements (SLAs) with each internal team. This approach builds mutual understanding and buy-in, making it easier to enforce timelines and address deviations from the agreed-upon process later on.

When facing emotionally difficult decisions like firings or reorgs, it's tempting to optimize for making people happy. The correct mantra is 'serve the business, not the people.' A successful business ultimately benefits everyone involved. This principle provides clarity and helps you make the right, albeit painful, call.

Leaders forfeit their right to be frustrated by subpar work if their quality bar is subjective and hasn't been explicitly communicated. To hold a team to a high standard, particularly one based on 'gut feeling,' you must document those expectations in specific detail. This transforms a subjective bar into an objective, referenceable standard.

When you establish clear boundaries and accountability, employees must make a choice. They either rise to meet the new standards or they leave. This process naturally filters out underperformers and those who prefer low-accountability environments, ultimately strengthening your team.

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.

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.