How Do You Talk to a Difficult Chief Technology Officer?

Ben Horowitz says there are no five steps for being a CEO. A mentor worth having is someone who can hold a real conversation, not someone who hands out instructions. He asks CEOs what is on their mind and where they are stuck, then uses mistakes he has already made.

One CEO asked how to think about a CTO who was an asshole. The CTO was executing better than anyone before, and the CEO was not going to fire him, so the real question was how to talk to him without driving him away. The CTO had been talking to a young woman in finance and made her cry. Horowitz would sit him down, call him a great director of engineering who ships products on time, and say he is not effective as a CTO until he can work with other functions and orchestrate the company so the technology part gets what it needs. Making someone cry means he will never get what he wants from her, her boss, or her boss's boss. They can work on making him more effective, or one day the company hires someone who already is.

A conversation like that is advice a founder can actually use, as opposed to a no asshole rule or something heard at Harvard Business School. Everything is situational: the company, the product, and the people. The person to talk with can be a peer just one step ahead.