Reframing Feedback for Disruptive CTOs

Situation

• A CEO approached Ben Horowitz with a challenging leadership problem: his CTO was technically competent but behaving poorly toward other departments
• The specific incident involved the CTO making a junior woman in finance cry
• The CEO felt stuck between two bad options: keep an "asshole" CTO or lose a technically strong leader
• The CEO explicitly stated he didn't want to fire the CTO but didn't know how to address the behavior without risking the CTO quitting

Actions

• Horowitz reframed the conversation from a personal character issue ("he's an asshole") to a professional effectiveness issue
• He provided specific language for the CEO to use that:
  • Acknowledged the CTO's technical strengths: "You're a really good director of engineering"
  • Redefined the CTO role as requiring cross-functional effectiveness: "To be a CTO you have to be effective with other parts of the organization"
  • Connected specific behavior to business impact: "Making somebody cry... you lost all effectiveness with all the finance team"
  • Offered support for improvement: "If you want to get good at that, I'll help you"
  • Created clear consequences: "If you don't, I'm going to have to hire a CTO at some point"

Results

• The CEO gained confidence that he could have the difficult conversation
• The approach provided a path forward that preserved the technical talent while addressing the problematic behavior
• The conversation shifted from a subjective character assessment to objective performance expectations

Key Lessons

• Frame feedback around effectiveness, not character: Discussing how behaviors impact business outcomes is more productive than labeling someone as "an asshole"
• Acknowledge strengths while addressing weaknesses: Starting with recognition of value prevents defensive reactions
• Define roles by their full requirements: Technical excellence alone doesn't qualify someone for leadership positions that require cross-functional collaboration
• Connect behaviors to specific business impacts: Show how interpersonal actions directly affect team effectiveness
• Provide clear choices with consequences: Offer support for improvement while establishing boundaries
• Leaders often hesitate because they lack the right framing: Many difficult conversations become possible with the right approach and language
• Specificity is more actionable than generality: Concrete examples and expectations are easier to address than broad character assessments