When interviewing salespeople, the biggest red flag is blame. Strong candidates demonstrate humility and self-reflection by taking ownership of lost deals and analyzing their own shortcomings. Weaker candidates deflect, blaming the product, competition, or other external factors, signaling a lack of coachability.

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.

Early leadership mistakes often stem from a perceived need to have all the answers. A more powerful approach is to express confidence in the mission while openly asking your team for feedback on how you can improve as a leader to better serve them and the company.

When evaluating senior candidates, don't view a failed entrepreneurial venture as a negative. It often indicates valuable traits like risk-tolerance, scrappiness, and resilience. These leaders have learned hard lessons on someone else's dime, making them potentially more effective in a new organization.

A venture capitalist's first question to a founder is about a major failure. An inability to answer ends the meeting, as it signals a lack of experience in confronting and overcoming adversity, a crucial skill for leading a startup.

Companies that consistently avoid dissecting failures, like lost deals, demonstrate a cultural aversion to learning. They prefer chasing new opportunities over improving. For employees in such an environment, this systemic refusal to learn is a major red flag indicating limited growth and a need to seek opportunities elsewhere.

Employees should test their managers by asking how they make decisions. A manager who cannot articulate their decision-making framework is a significant warning sign, suggesting a lack of clarity and potential organizational chaos. This serves as a powerful "reverse interview" technique for assessing leadership.

Beyond IQ and EQ, interview for 'Resilience Quotient' (RQ)—the ability to persevere through setbacks. A key tactic is to ask candidates about their proudest achievement, then follow up with, 'What would you do differently?' to see how they navigated strife and learned from it.

Great founders turn a pitch into a collaborative discussion by asking investors to identify business weaknesses. This signals curiosity, strength, and a desire for genuine feedback over just presenting a perfect picture. It demonstrates a coachable leader who is focused on gathering data to improve.