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.

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Most leaders are conflict-avoidant. Instead of running from tension, view it as a data point signaling an unaddressed issue or misalignment. This reframes conflict from a threat into an opportunity for discovery and improvement, prompting curiosity rather than fear.

To empower your team, enforce the '1-3-1 rule' for problem-solving. Before anyone can escalate an issue to you, they must define the one problem, research three potential solutions, and present their single best recommendation. This forces critical thinking and shifts the team from problem-spotters to problem-solvers.

When an employee seems defiant, it's rarely a deliberate act of insubordination. Instead, it's a signal that a request has caused an internal conflict or values mismatch. Leaders should treat this as a cue to investigate the root cause, not to punish the behavior.

Navigate disagreements with a four-step method: use uncertain language (Hedge), find common ground (Emphasize Agreement), demonstrate what you heard (Acknowledge), and frame points positively instead of negatively (Reframe). This prevents conversations from spiraling into negativity.

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.

Don't be afraid to surface problems to executives, as their job is almost entirely focused on what's not working. Withholding a problem is unhelpful; clarifying and framing it is incredibly valuable. Your champion isn't offending their boss by raising an issue, they're demonstrating strategic awareness.

In difficult conversations, leaders fail when focused on their own feelings or ego. The real work is to get to the absolute truth of the situation. This involves moving past your own reaction to understand why the person acted as they did, if the behavior is correctable, and what would truly motivate them to change.

The key to a successful confrontation is to stop thinking about yourself—whether you need to be seen as tough or be liked. The singular goal is to communicate the unvarnished truth in a way the other person can hear and act upon, without their defensiveness being triggered by your own emotional agenda.

When progress on a complex initiative stalls with middle management, don't hesitate to escalate to senior leadership. A brief, well-prepared C-level discussion can cut through uncertainty, validate importance, and accelerate alignment across teams or with external partners.

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.