When a high-potential but cocky employee challenges a key decision, directly address their lack of coachability. Jeremy Duggan turned a new hire's complaint into a 24-hour ultimatum to "get his job back." This high-stakes move reframed the conversation from selling the change to demanding coachability, transforming a talented individual into a top performer.
To cultivate a culture of high agency, frame ultimate responsibility as a privilege, not a burden. By telling new hires 'everything's your fault now,' you immediately set the expectation that they have control and are empowered to solve problems. This approach attracts and retains individuals who see ownership as an opportunity to make an impact.
When an employee presents a problem they should be able to solve, resist providing a solution. Instead, return ownership by asking, "What do you think you should do about that?" This simple question forces critical thinking and breaks the team's dependency on you for answers.
To build a culture of continuous improvement, prioritize hiring for coachability. Individuals with backgrounds in competitive athletics or music are often ideal because they have been heavily coached their whole lives. They view direct feedback not as criticism, but as an essential tool for getting better.
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 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.
Annual or quarterly performance reviews are high-pressure, judgmental events that create fear. A more effective approach is to reframe management as coaching. This means providing frequent, trust-based feedback focused on developing an employee's long-term potential, rather than simply rating their past performance.
Keeping an employee in a role where they are failing is a profound disservice. You cannot coach someone into a fundamentally bad fit. The employee isn't growing; they're going backward. A manager's responsibility is to provide direct feedback and, if necessary, 'invite them to build their career elsewhere.'
A manager's highest duty is to an employee's fulfillment, not just their performance. When a top performer is not personally aligned with their role, a leader should actively help them find a better fit—even if it means using their own social capital to place them at another organization.
To prevent defensiveness when giving critical feedback, managers should explicitly state their positive intent. Saying "I'm giving this because I care about you and your career" shifts the focus from a personal attack to a supportive act of leadership aimed at helping them grow.
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.