I was having drinks with Philip a few years back and he asked about the mobile transition. I mentioned arguing with Mark during it and after a pause I said “arguing with CEOs might be my superpower.”

Philip agreed and proceeded to almost fall out of his chair laughing.

Debate and debate again

At Google, my colleague Diane once asked me how I managed to get so many things done at Google that others have tried and failed at. Ultimately, I think it’s about embracing career limiting moments with senior leaders, especially CEOs. About doing your best to be fearless, even when you are scared.

We’ve all been in jobs that we had to keep because of finance, health care, or other reasons. I’m also incredibly lucky — I’m a white nerd playing life on the easy setting — so it’s a legitimate criticism of the point that I’m not really taking the risks that others might be.

Fair and true. But…

Here’s the thing. I’ve worked for and with some of the most amazing — and opinionated — CEOs out there. Philip. Mark. Sundar. If you discover that someone with as much real, soft, and positional power as they have isn’t willing to debate and learn, your job is going to be somewhere between ‘sucktastic’ and ‘impossible.’ Nobody — no matter how singular — is right all the time. Great leaders know that.

Find leaders who you can debate and learn with. If that isn’t your current situation, start working on your resume.