Important lessons in your career can come from brief interactions with effective leaders. I had one of those interactions with Charlie Bell at Amazon 20 years years ago, and I’ve never forgotten it. Here’s what happened:
I was a middle manager in Amazon’s retail business and Charlie was a vp of engineering (on his way to svp and co-founder of AWS). We were working on something urgent, I don’t even remember what it was. But I remember Jeff Bezos was not happy with me.
I ran into Charlie at the company picnic. I pulled him aside and said “we need to do something right away because Jeff is pissed.” He looked me in the eyes and said “let’s forget about Jeff for a minute, what’s the right thing to do here?”
This was an aha moment, it never occurred to me there could be a difference between what Jeff wanted and what we should do. But I knew there was a better answer. We discussed my recommendation and Charlie agreed with me. Then we talked about how to get Jeff on board.
It’s hard to push back on the CEO, they have the most context and power. But their context is wide and shallow, and sometimes they miss important nuance. The job of a senior leader is to fill in that nuance by framing decisions clearly and escalating efficiently. Not to complain.
Many years later I found myself in a situation at Facebook that reminded me of this lesson. Zuck and I disagreed about something that seemed existential to the business, and he asked me to take it to the board for their input (to his credit, he took our debate to the board).
Several weeks later I ran into FB board member Reed Hastings, and he asked me if we had made a decision. I told him it would be much easier for me to just do what Mark wanted, but I didn’t think it was the right thing for the business. Reed encouraged me to keep making my case.
At the end of the day, the CEO gets to decide. But until they make their final decision, a leader’s job is to make their case. Great CEOs encourage dissent and leave space for debate. Great leaders have the ability to discern that space, and agility to make their case effectively
Great CEOs are also stubborn, decisive, impatient and wicked smart (trust me, I worked for two of them!), which makes it difficult to push back. It’s natural to just do what they ask now and complain about it later. Effective senior leaders know to do the opposite:
They make a strong case, patiently working through the pros and cons and debating for as long as the decision is left open. And when they lose a debate with their CEO, they disagree and commit, and start selling the decision to others so there’s alignment up and down the org.
I often disagreed with Bezos and Zuck, but I trusted them. They encouraged debate, were right more than they were wrong, and they had a special knack for being really right about the big stuff. If you don’t trust the judgement of your CEO, you’re working at the wrong company.
If I couldn’t convince Jeff or Mark to follow my recommendation, I viewed it as my failure not theirs. I looked at the decision through their lens, always wider than mine even if sometimes shallower. I didn’t complain, and I never said I told you so (neither did they). Onwards!

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