When I worked at Amazon 1999-2006, Jeff Bezos’ favorite interview question was “are you a lucky person?” What a great way to filter for optimists and people who manifest success.
If you’re a successful, optimistic, humble leader the right answer starts this way: “Yes, I’m the luckiest person on earth. I’ve worked hard to get to this point in my career, but a lot of things also had to go right and I’ve taken full advantage of my luck.”
Sorting for optimistic people is a good proxy for leadership potential and likelihood of success. Perceiving yourself as lucky is a good proxy for optimism.
Humility is also important, and it’s easy to filter out false humility (“humble brags”) in follow-up questions. This isn’t the only question, it’s a conversation starter and opens to door to exposing someone’s personality beyond their resume.
Two wrong answers: 1) No, I’ve never felt lucky but I’ve been able to overcome all the bad things that always happen to me; 2) No, I’ve never needed luck because I am better/smarter/stronger than everyone else.

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More from @DanRose999

5 Jul
One of the most important things I learned from Jeff Bezos was to develop a bias for action. He wasn't always right, but he was always ready to act (and he was right much more than wrong). Like the time we were flying to Chicago and nearly wound up in Paris. Here's what happened:
In 2004, I joined Steve Kessel's newly formed digital team to incubate the Kindle. This was Amazon's first hardware project, a somewhat daunting initiative for a retailer. Jeff had met the CEO of Motorola who invited him to Chicago for a tour and meetings, and he brought us along
Steve brought me + 2 other people from the team, we got on Jeff's plane in Seattle. Jeff was fired up from the start, posing strategy questions & brainstorming our approach to hardware, software and content (my job). He had us captive for 4 hours and didn't waste a second.
Read 9 tweets
12 Jun
In my experience the best founders develop a fighter mentality. Mark Zuckerberg was a fighter, and without that mentality Facebook would never have achieved its full potential. Here’s what I saw over 13 years working for Zuck:
One of Mark’s first big fights was with his own board + exec team. They tried to convince him to sell the company to Yahoo for $1B in '06. At the time FB had 5M users (all college) and was 2 yrs old. At the age of 22, Mark stood to gain $300M personally. How could he say no?
Everyone told Mark to sell. Friends said he'd be crazy to pass up $1B. His management team wanted an exit. His board put pressure on him. But Mark knew something they didn’t – FB was on the cusp of launching new products that would completely change the trajectory of the company.
Read 16 tweets
23 May
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?"
Read 12 tweets
26 Apr
I was ambitious and worked hard to advance my career at Amazon and then Facebook. I thought the way to get ahead was to deliver results, then push for more responsibility and position myself for promotion. I later came to realize I had it totally backwards. Here's my story:
Ambition can be a good thing when it's channeled productively. Ambitious people push forward. For example, my litmus test for whether I should stay in a job or make a change was always to ask myself whether I was still on a vertical learning curve. If not, find a new challenge.
But early on I was nakedly ambitious. After one year at Amazon I thought I deserved to be Director. When my manager didn't promote me, I moved to another team who offered to promote me as part of the move. The promotion was later rescinded because my new manager lacked authority.
Read 17 tweets
3 Apr
What defines a great company culture? I worked for two iconic companies and founders with nearly polar opposite cultures. Amazon was heads-down, secretive, forthright. Facebook was open, transparent, collaborative. Here's what I learned about culture working for Bezos and Zuck:
Culture implicitly sets expectations for behavior. Strong cultures are well-defined with sharp edges, and well-understood by everyone in the organization top to bottom. Strong founders with unapologetic personalities set the culture early and maintain it as the company scales.
When I joined Amzn in 1999, we had top-secret teams working on new products like Auctions, Toys and Electronics. Before a product launched, the only people in the know were those who needed to know. Everyone else was told to keep their heads down and focus on their own work.
Read 17 tweets
12 Mar
I learned about leadership & scaling from Sheryl Sandberg. My direct manager for 10+ yrs, we spent countless hours together in weekly 1x1s (she attended religiously), meetings, offsites, dinners, travel, etc. Here are some of the most important lessons I took away from Sheryl:
In one of our early M-team offsites, everyone shared their mission in life. Sheryl described her passion for scaling organizations. She was single-mindedly focused on this purpose and loved everything about scaling. It's a huge strength to know what you were put on earth to do.
Sheryl implemented critical systems to help us scale - eg 360 perf reviews, calibrations, promotions, refresh grants, PIPs. She brought structure to our management team and board meetings, hired senior people across the company, and streamlined communications up and down the org.
Read 17 tweets

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