When making tough personnel decisions, leaders should frame the choice not as a personal or purely business matter, but as a responsibility to the rest of the organization. Tolerating poor performance at the top jeopardizes the careers and stability of every other employee, making swift action an act of collective protection.
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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.
The most common failure mode for a founder-CEO isn't a lack of competence, but a crisis of confidence. This leads to hesitation on critical decisions, especially firing an underperforming executive. The excuses for delaying are merely symptoms of this confidence gap.
For leaders who are natural empaths, a key growth area is learning to separate deep personal care for team members from the objective needs of the business. This includes recognizing that letting someone go can be the most loving and correct decision for the individual, the team, and the company.
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.
Focusing on "bad to great" is more effective than "good to great" when scaling. Bad behaviors and destructive norms are so corrosive that they make it impossible for excellence to take root. A leader's first job in a turnaround or scaling effort is to eliminate the bad—like dirty bathrooms or incompetent employees—before trying to implement the good.
A leader's failure to deliver difficult feedback, even with good intentions, doesn't protect employees. It fosters entitlement in the underperformer and resentment in the leader, leading to a toxic dynamic and an inevitable, messy separation. True kindness is direct, constructive feedback.
If a decision has universal agreement, a leader isn't adding value because the group would have reached that conclusion anyway. True leadership is demonstrated when you make a difficult, unpopular choice that others would not, guiding the organization through necessary but painful steps.
Unlike a line manager who can train direct reports in a specific function, a CEO hires experts for roles they themselves cannot perform (e.g., CFO). A CEO's time spent trying to 'develop' an underperforming executive is a misallocation of their unique responsibilities, which are setting direction and making top-level decisions.
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.
When confronting a talented but abrasive CTO, don't just critique bad behavior. Frame the conversation around their effectiveness. Horowitz suggests saying, "You're a fantastic Director of Engineering, but not an effective CTO," because a true CTO must marshal resources across the entire company, not just manage their own team well.