Take Risks, Handle Setbacks, and Grow Your Career
Failing Jeff Bezos twice and the 5 steps used to recover and eventually grow
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If you wait for certainty, you will be too late.
In business, someone else who is willing to gamble on early signals will beat you to whatever you are working towards. To succeed, we must take risks.
But if we take enough risks, even good ones, eventually something will go wrong.
So, our success is not only dependent on taking risks, but also on our ability to recover when one of those risks lands us in some trouble. In my career, I had to recover from two large, public mistakes.
Here is how I recovered and used to the experience to gain trust and credibility.
“I Believe You Have My Stapler”
Imagine me on a stage.
The auditorium is packed with Amazonians for the quarterly all-hands meeting. My VP and my SVP are sitting in the front row, looking up at me. Right next to them was Jeff Bezos, staring up at me as well.
It’s August 2006, and we are days from launching Amazon’s first digital media product. There is no Kindle, and Amazon AWS is completely new. Amazon makes most of its money from selling physical media, like books, CDs, VHS tapes, and DVDs.
I am about to demo the very first version of Prime Video to the entire company.
Our team’s business leader is introducing the product. He is a Hollywood insider, and he is trying to warm up a crowd composed mainly of retail merchandisers and software engineers with movie jokes. When his jokes fall flat, he panics and hands me the microphone with a quick introduction - “Here’s Ethan to show you more.”
A year earlier, Jeff Bezos had chartered three teams to take Amazon into the Digital age of media:
A books team was building the Kindle e-reader.
A music team was working on Prime Music.
And I was hired to build Prime Video (the origin of Amazon Prime Video).
I was hired from a startup into a Senior Manager role, and I led a modest team of just nine people. 20 years ago, Amazon was only 1% of its current size – 15,000 people rather than 1.5M.
Jeff had kept Amazon’s shift towards digital media a secret, both internally and externally, so our launch will also announce a new strategy. Given this, he asked us to demonstrate the new product at the all-hands, emphasizing how important it was to make a good impression on the market.
The secrecy caused me some problems. In 2006, home broadband was still relatively new, and our product was based on downloads. Choose a movie, download it, and watch it later.
I knew how to build PC software, and I knew that a beta program was necessary to find all the bugs that would appear across the infinite variations of software configurations in the marketplace. However, despite pushing hard for beta testing, the decision was made to prioritize secrecy over a public beta and launch without testing.
For the all-hands demo, I have downloaded Office Space and queued it up to the famous red stapler scene. I step forward, explain how the product works, and press play on the demo.
The crowd roars with laughter.
I turn around to see the 40-foot screen behind me, and slowly bend over, turning my head upside down.
Office Space is playing. 40 feet high. Upside down.
I turn back, alone in the spotlight, and see Bezos and my VPs looking at me, with a thousand Amazonians behind them.
I looked at Jeff and the audience, and said, “Jeff told us that this product has to ‘just work.’ Obviously, it doesn’t. I’m going to go fix that.”
Then I left the stage.
No matter how careful you are in your career, at some point you will fail and you will need to recover, in public.
We would later learn that Microsoft (who managed the video player for that version of Prime Video) knew about an obscure bug where video that was paused for several hours would sometimes resume play upside down. To this day, I have no idea what kind of code would generate this behavior, but setting up our video in the morning and pausing it until I was on stage had triggered this bug.
In the moment, I had no idea what was wrong, only that our demo had just failed in front of the entire company…
How to Recover
You can make mistakes in your career and recover from them. You can suffer setbacks and still move forward. It depends on both how you handle them and the culture of the leadership team above you.
After my big mistake, I did a few things that you can learn from and copy when you need to:
I acknowledged the obvious fact that there were big problems.
I made clear that I understood the importance of the problem.
I stated a simple plan: to go fix it.
I made clear I owned it and that I would fix it personally.
Those are the four things I did on stage, but the recovery process didn’t end there.
Back then, Jeff Bezos had a tradition of taking all the presenters from the all-hands to lunch after the meeting. The lunch spot was up the street, and I left the venue quickly and walked to the restaurant.
Arriving, I found Jeff seated alone in a private dining room.
I looked at him and immediately started for the furthest seat from him I could find.
Jeff called out and said “No, come sit by me.”
I assumed I was about to either get chewed out or fired. But, I went and took a seat next to him…Jeff said, “I’m not worried about the problems today because I know you are.”
This response was crucial to me being able to follow through on my recovery plan. Recovering from setbacks requires good leaders, and many CEOs would have criticized, questioned, or micromanaged their employee after a failure like that. Some would even have screamed obscenities.
Jeff just expressed a quiet confidence that I could handle the problem, and then we shared lunch.
To recover from a setback, you must own the problem and fix it. But, you also have to work for good leaders who support you. If you work for a tyrant, you will not be able to recover. At that point, my advice is to find a better job.
Just over a year after this disastrous demo, following a series of successful innovations and launches, I was promoted to Director. Rather than fleeing the company in shame or being chased out by an angry leader, I had recovered and taken a major step in my career.
Don’t Avoid Failure
The secret to success is not avoiding failure, but handling it in a way that builds confidence in your leadership. The way I handled the video disaster was part of what allowed me to be promoted to Director. Four years later, my recovery from another disaster helped me go from Director to VP.
Four years after my promotion to Director, I was once again launching a product in front of Jeff Bezos. By this time, I was a veteran Director with a team of over 100 people.
This launch was not on a stage, but rather an overnight deployment that led up to a press release in the morning, before the stock exchange opened. My job was to launch the Appstore, Amazon’s answer to the Google and Apple Appstores, to the public.
When Amazon released new features in this era, Jeff would take over the home page of the website, replacing the usual product offerings with a personal letter that introduced the product to “his” customers. He had written such a letter for the Appstore launch, focusing on one key feature.
Our team worked through the night to deploy the new Appstore for another “surprise” launch, but as morning came we noticed a problem. Most of the store was working as designed, but the key feature Jeff had written about was having intermittent failures.
At about 6 AM, I got an email from Jeff that asked, “Where’s the letter?”
I replied, “We’re working on some problems,” while thinking to myself, “Please, Jeff, just get in the shower!” Like most engineers, I believed that we just needed a few more minutes to track down the glitch, and if Jeff just took a morning shower everything would be ready by the time he got out.
But, seconds later, Jeff replied, “What problems?”
And the audit began.
Over the next hour, as more leaders woke up and saw the thread, the crisis intensified. Jeff was demanding answers we didn’t have, and the whole management chain under him was asking questions too.
The Prime Video demo failure four years beforehand had been a single, obvious problem. This time, the crisis was building slowly, starting from one email and eventually growing into a “war room” filled with principal engineers and managers from all over the company.
As the morning wore on and the problem persisted, Jeff became more frustrated. His emails read more like flames than questions, and he demanded that the product be fixed immediately.
As the leader responsible for the product, I took visible ownership: I started sending clear hourly updates to Jeff and all the leaders on the thread.
Each hour, I would send an email with three key elements.