When leading a function outside your expertise (e.g., a comms leader managing BDRs), success depends on hiring a great functional leader. Your role becomes asking them to explain concepts simply until you understand, trusting their expertise, and advocating for their needs, rather than trying to become the expert yourself.

A key trap for experienced founders is assuming success in one domain translates to expertise in another. This temptation toward arrogance is amplified because their teams are less likely to question their judgment, leading to flawed decisions in unfamiliar areas.

To gauge an expert's (human or AI) true depth, go beyond recall-based questions. Pose a complex problem with multiple constraints, like a skeptical audience, high anxiety, and a tight deadline. A genuine expert will synthesize concepts and address all layers of the problem, whereas a novice will give generic advice.

Leaders who were correct once in a specific area, like mobile UX in 2015, tend to believe their expertise is universally applicable. This cognitive trap leads them to make poor, unsubstantiated decisions in new domains like AI strategy.

When leading functions outside your core expertise (e.g., product leading tech and data), credibility cannot come from having answers. Instead, it's built by consistently asking open-ended questions to deeply understand the team's challenges. This approach prevents solutionizing and fosters trust.

While experience builds valuable pattern recognition, relying on old mental models in a rapidly changing environment can be a significant flaw. Wise leaders must balance their experience with the humility and curiosity to listen to younger team members who may have a more current and accurate understanding of the world.

Joining as a new tech lead for an existing team, the speaker built trust by forbidding himself from giving direct orders or rejecting designs. He instead embedded with teams and used strategic questioning to guide them, helping them arrive at the right conclusions while respecting their expertise.

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.

If a highly successful person repeatedly makes decisions that seem crazy but consistently work, don't dismiss them. Instead, assume their model of reality is superior to yours in a key way. Your goal should be to infer what knowledge they possess that you don't.