To change unwritten, bureaucratic rules, such as those in performance calibrations, avoid confronting decision-makers in a group setting where they become defensive. The speaker advises having private 1-on-1 conversations beforehand to understand the rule's origin and present your case with evidence.
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Directly confronting someone about a behavioral 'blocker' often causes defensiveness. A better method is to first demonstrate your own self-awareness and vulnerability. Then, ask for permission to share observations, which creates trust and makes them more receptive to exploring their behavior.
People become defensive when given unsolicited advice. To create an opening for constructive criticism, first ask the other person for feedback on your own performance. This act of vulnerability establishes trust and often triggers a natural social tendency for them to reciprocate, making them more receptive to your feedback in return.
As leaders rise, direct reports are less likely to provide challenging feedback, creating an executive bubble. To get unfiltered information, leaders should schedule regular one-on-ones with employees several levels down the org chart with the express purpose of listening, not dictating.
Instead of directly opposing a decision, surface the inherent dilemma. Acknowledge the desired goal (e.g., speed), then clearly state the cost ('If we do X, we trade off Y'). Then ask, 'Is that a tradeoff we are comfortable making?' This shifts the conversation from confrontation to collaborative risk assessment.
To maintain a flat, hands-on engineering culture without dedicated managers, Fal replaces traditional one-on-ones. They feel 1-on-1s can force negativity and instead use small group discussions with mixed tenure and roles. This format fosters more constructive, solution-oriented conversations rather than simple complaint sessions.
Escalating a conflict by attacking an individual will likely backfire on your career. The correct approach is to escalate the systemic issue. Frame the problem as a broken or unclear decision-making process, and ask leadership for clarity on how such disagreements should be resolved.
When your proposal is too far from someone's current position, it enters their "region of rejection" and is dismissed. Instead of asking for the full change at once, start with a smaller, more palatable request. This builds momentum and makes the ultimate goal seem less distant and more achievable over time.
When you identify a deal blocker, don't confront them alone. First, approach your champion and ask for their perspective on the dissenter's hesitation and advice on the best way to engage them. This provides crucial internal political context and helps you formulate a more effective strategy before you ever speak to the blocker.
Instead of offering unsolicited advice, first ask for permission. Frame the feedback around a shared goal (e.g., "I know you want to be the best leader possible") and then ask, "I spotted something that's getting in the way. Could I tell you about it?" This approach makes the recipient far more willing to listen and act.
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.
