9 Hard Lessons You Learn as a Director at Amazon
What unexpected things happen when your scope increases, almost everything is ambiguous, and results (not effort) are all that matter.
Welcome to the Scarlet Ink newsletter. I’m Dave Anderson, an ex-Amazon Tech Director and GM. Each week I write a newsletter article on tech industry careers and tactical leadership advice.
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My initial interest in early retirement started as I imagine the majority of the community discovers the idea. Sitting there at my work desk, I felt a sense of existential disappointment at the idea of working another 40 years.
I’m glad that I began my savings journey, and while I had detours along the way, the lessons I learned landed me in a pretty great place. I get to sit here in my home office with a coffee next to me, writing a lovely letter to thousands of people.
However, I don’t want to lose track of a vital lesson (yes, at least loosely related to this article).
If you were to smooth out a graph of my average work satisfaction over time, it would be clear that as I progressed in my career, work began to be less unpleasant. The negative aspects decreased, and every year I was able to engage with more work that I honestly enjoyed.
When you look at senior employees who seem genuinely excited to be in the office, I used to wonder what was wrong with them. “They’ve made plenty of money. Why are they still in the office every day?”
I mean, I still think that to some extent. But there’s a kernel of wisdom here as well. Read any LinkedIn or Reddit post about work, and you’ll find a good number of junior employees filled with bitterness and cynicism. They rail at the stupidity of management, the incoming AI wave as defeating all hope of a better future, and the pointlessness of their daily tasks.
But I think the junior years of work are honestly pretty hard. You don’t understand why you’re doing things (sometimes people don’t bother telling you, or you just don’t understand). Your work is a small piece of a big jigsaw puzzle you quite possibly don’t see. And your work is rarely influential in the grand scheme of things, so you really are just a small cog in a big machine.
The opposite end of the career ladder is interesting. Because if things have gone well, you might now be directing hundreds of cogs. You’ll know exactly why you’re doing the work, and you frequently agree with it. You can see the bigger puzzle, and you can identify how you specifically helped put that puzzle together. Plus, you have significant autonomy over your specific contributions, and those frequently line up with your skills and interests.
So the job is better. And that’s probably a significant aspect of why many senior people with fat bank accounts continue to work. They are finally at the point in their career where they’re having fun. And while I didn’t like my job enough to stay, I can at least understand the idea. I think it’s worth sharing this knowledge with everyone because it’s healthy to see the light at the end of the tunnel. You, too, may enjoy your job someday. If you don’t already, that is.
Okie dokie, time to move on.
Sharing my experiences.
I wanted to write about what it was like to move into a senior leadership position at Amazon. It’s the type of thing that many people never get to experience.
Several times I’ve written narratives about what it feels like to be in those roles. Those articles turned into some of the more popular things I’ve written. So if you haven’t read them, take a gander.
I enjoy writing narratives about my experiences. It’s a fun writing process. However, explaining one small concept can easily take more than 1000 words, and I had a list of things I wanted to share directly.
What senior leadership is like.
I’m going to walk through some aspects of senior leadership. They’re certainly Amazon biased, but I’m fairly sure the majority apply to any senior leadership position.
To help clarify things, I'll start by running through Amazon’s leveling system.
Levels at corporate Amazon to help understand my brief explanations:
L4 - Entry level, this is where you’re hired as an engineer (or other line employee).
L5 - Mid-level experienced engineer. You’re a few years into your career.
L6 - Senior engineer / line manager (Software Development Manager for example). Usually the most senior engineer of a team and/or the manager of the team at that level.
L7 - Principal engineer / Senior Manager. Go one level up in the management chain. So the engineer or manager has ~6 times the scope / influence.
L8 - Senior Principal Engineer / Director. One more level up the management chain. ~6 times the scope / influence of L7, and correspondingly, ~36 times the influence of L6.
L9 - Yeah, that doesn’t exist for a mysterious reason.
L10 - Distinguished Engineer / VP. Again, another level up. Another massive scope jump.
Above that is SVP (Senior Vice President), and then CEO.
Part of my point in sharing this is that each level sounds like “just one level up,” but Amazon has few levels, so each level means a significant change in influence.
1. Leaders quit or get emotionally harder.
I’ve met many line managers who had a hard time giving negative feedback to their team members. You don’t generally see people with that difficulty as they move through L7 into L8+.
I think it’s a mixture of selection, burnout, and numbing.
Selection
Senior leaders generally look at someone too emotionally soft as not leadership material. For example, a L6 manager says they have an underperforming engineer on their team. I ask them to copy me on their written feedback. They wince, and don’t do it for 2 weeks. They’re avoiding the emotional pain of communicating the performance feedback. That’s not acceptable at L6, and I wouldn’t dream of promoting someone like that to L7.
Burnout
Senior leaders and executives don’t generally sugarcoat feedback. They don’t have patience for it, and they think (for good reason, in my opinion) that clear and precise feedback is best. The higher the level, the less likely they are to spend words on being gentle. “This document is not acceptable to present to the SVPs. You can do better. Rewrite it.” If that type of feedback stresses you out, you won’t last long in a position above L6. In my experience, this is a big source of people quitting management positions. That type of pressure stresses them out, and they find roles elsewhere. Sometimes at more gentle companies. Sometimes in lower level positions.
Numbing
If you give feedback to enough employees, you get used to the emotional pain created. And at least in my experience, I saw it as a necessary pain, so I may as well rip the Band-Aid off.
“I’m afraid you’re not performing well, and your job is therefore at risk.”
At the beginning of my career, it would be fairly terrifying to say that. Later in my career, it wasn’t zero impact, but I could handle it. I knew they needed to hear it, and I couldn’t be shy about it.
However, I’d still say that we (senior leaders) got some rough edges by being put in that situation repeatedly.
