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To test for self-awareness and honesty, ask executives to grade their own execution on an A-F scale. If a team that repeatedly blames external factors (like weather) gives itself a high grade like a 'B+', it's a significant red flag about their integrity and accountability.

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To maintain high standards in any role (CEO, parent, partner), use this simple self-audit question. It forces an objective assessment of your performance. If you wouldn't recommend yourself, you must confront the specific shortcomings and take corrective action.

The key trait for scaling a company is ownership. To screen for it, ask candidates about their mistakes. A-players will admit a genuine flaw, like having trust issues that lead to micromanagement. B-players will offer a veiled brag or fake weakness, which is a major red flag.

To expose vulnerabilities, run a "murder board" offsite. Task your team with a simple goal: if you were a new, well-funded competitor, how would you kill our company? This exercise forces brutal honesty, counters a culture of overly positive "optics," and reveals weaknesses before the market does.

Directly ask your manager, "When you talk about my performance in leadership meetings, what are the main points you emphasize?" An honest manager will answer directly, while a manipulative one will likely deflect or become defensive, revealing their lack of transparency.

In his first week leading a turnaround, Peter Cuneo asks direct reports to identify who made past mistakes. This question quickly reveals who takes ownership versus who blames others, allowing him to immediately assess his team's character and decide who to keep for the long term.

To get truthful feedback, leaders should criticize their own ideas first. By openly pointing out a flaw in their plan (the "ugly baby"), they signal that criticism is safe and desired, preventing subordinates from just offering praise out of fear or deference.

Instead of telling a leader what they're doing wrong, ask what impact they want to have. By comparing their desired outcome (e.g., 'I want my team to bring me new ideas') with the actual result (e.g., 'no one speaks up'), the leader is intrinsically motivated to identify and correct the behaviors causing the gap.

Framing a question about past errors as a "do-over" bypasses management defensiveness. It encourages more honest reflection on decisions and reveals a leader's capacity for humility, a key trait for avoiding corporate blow-ups.

To gauge a leader's coachability and the company's health, ask them to describe a time they were wrong about the market and how the organization pivoted. A leader who can't admit to missteps or share learnings is a major red flag, signaling a lack of self-awareness that will hinder growth.

An effective manager evaluation technique is to recognize that everyone presents their polished "best self" initially. An allocator's primary job during due diligence is to actively investigate beyond this facade to uncover the manager's "true self"—how they operate under pressure and handle failure—before committing capital.

Ask Management to Grade Its Own Performance to Expose Dishonesty | RiffOn