Andy Jassy shares 9 things he’s learned over 28 years at Amazon

In his latest annual letter to shareholders, Amazon CEO Andy Jassy says we're in the middle of some of the biggest inflections of our lifetime. To cultivate a culture that can be adept at managing these inflections, Jassy shares nine things he’s learned over his 28 years at the company: 1.

You need to have the right data, mechanisms, and truth-tellers to deeply question what’s changed and should therefore be done. 2. You have to have people and a culture that are comfortable operating with ambiguity as you sort through the new normal. 3. You need to invent and experiment like crazy.

Many of these experiments will fail, and it might feel like you’re getting nowhere. But, your culture must possess the tenacity to keep at it. 4. You need to learn constantly. Each attempt you (and others) make provides insight on what customers really want. 5. You need to move fast, have teammates that act like true owners, and be scrappy.

At Amazon, we talk a lot about operating like the world’s biggest startup. It’s the primary reason we’ve worked to flatten our organization the last year, and we’re pleased with the improved speed of decision-making and delivery. 6. You have to be comfortable potentially over-rotating when pursuing one of these big needle-movers.

You may end up investing a little more than needed, but it’s better to capture most of the transformational upside than to miss much of it by cutting it too fine. And then, if you learn something new that requires course correcting, do it quickly. Inflections aren’t usually smooth or calm. They favor the bold and adaptable. 7.

You have to be adept at both inventing the inflections and recognizing when others have started ones that you should pursue as well. We tend to be first-movers, but have had several big successes where we didn’t enter first. In each of these cases, we haven’t just duplicated what others have done (when we’ve done that, we haven’t succeeded).

Rather, we’ve been inspired by new ideas, and invented unique experiences that appeal to our customers. It takes a different type of grit and resolve than when you’re first to an idea. 8. You have to be willing to reimagine not only every customer experience, but also how you organize and get work done.

Challenging conventions that have existed a long time (and worked) is difficult. People sometimes call these “change management” obstacles. That’s true, but in times of transformational tumult, they’re almost like reexamining your faith. 9. And, you have to be able to withstand criticism as you’re making your way through an inflection.

We have historically shared that we’re “comfortable being misunderstood for long periods of time.” This resolve is required when you’re inventing in general, but particularly when you’re in the middle of a meaningful change where there’s uncertainty and conflicting opinions. For more, read Jassy’s full letter to shareholders.

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