Directly asking about values often yields aspirational answers. A more effective method is to ask someone who they admire. The qualities they praise in others are a reliable indicator of the values they genuinely hold and strive to embody, revealing their character more accurately than a direct question.

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To accurately assess a leader's actions, especially an unconventional one, avoid asking 'What would it mean if I did that?' Instead, ask 'What does it mean that *they* are doing that?' This helps separate your personal behavioral standards from their actual intent and worldview.

Move beyond surface-level discovery questions. Asking 'What do you value most in a partner?' forces prospects to articulate their core needs for a relationship (e.g., responsiveness, consultation). Their answer quickly reveals if there is a fundamental values alignment, a better predictor of success than technical fit.

Adopting a single 'role model' is flawed because no one is perfect. A better approach is to consciously identify the one thing each person you meet is exceptionally good at. This allows you to learn from a wide array of strengths without being blinded by their shortcomings.

Transactional questions get transactional answers. A "story-worthy" question, like "Tell me about the moment you first sensed trouble with your supplier?", prompts a narrative. This approach extracts the emotion, context, and deeper story behind an issue, leading to more authentic connection and insight.

Your core values aren't just abstract principles you admire; they are revealed by the concrete things you willingly give up time, ego, or comfort for. Observing your sacrifices provides a clearer, more honest assessment of what truly drives you.

Asking questions that probe values, beliefs, or experiences—"deep questions"—can create surprisingly intimate connections in seconds, even with strangers like a barista. These questions invite authenticity and move beyond superficial small talk, making the other person feel seen and valued.

True connection requires humility. Instead of trying to imagine another's viewpoint ("perspective taking"), a more effective approach is to actively seek it out through questions and tentative statements ("perspective getting"). This avoids misreads and shows genuine interest.

People are practiced and guarded during formal meetings. To understand their true nature, Negreanu suggests engaging with them in informal environments like a meal or drinks. This disarms them, making their reactions more authentic and revealing.

Don't try to invent aspirational values. Your true values are already embedded from childhood, often as a reaction for or against your experiences. The process is one of self-excavation—analyzing consistent behaviors during life's highs and lows—not wishful thinking.

To gauge a partner manager candidate's empathy, ask for an example of a proud accomplishment. Candidates who frame success in terms of helping their partner achieve a goal, rather than just hitting their own targets, demonstrate the genuine care required for true partnership. This reveals their core motivations more effectively than direct questions.