Lessons From the Shadow

A REACTION TO JEFF BEZOS’ TRANSITION FROM CEO TO EXEC CHAIR OF AMAZON - AND A CHALLENGE!

Someone recently asked me what it feels like to “finally step outside the shadows cast by my former-CEO bosses” now that I have founded a company of my own after 15 years as the right hand to Jeff Bezos (Amazon), Marissa Mayer (Yahoo) or Eric Schmidt (Google). That question, honestly, surprised me. I have never felt like I was in their shadow! Quite the opposite. 

Yes, they are among the wealthiest, most powerful and smartest executives in the world. It might seem reasonable for someone to feel small or invisible when in the room with them and feel comparatively in the dark standing just outside their blinding spotlight. However, I learned very early in my career that that proximity isn’t diminishing; it’s empowering when you chose for it to be. 

I learned that lesson directly from Andy Jassy, who just yesterday became Jeff Bezos’ successor as CEO of Amazon. 

My very first job out of undergrad was working directly with Jeff Bezos during the foundational years of Amazon. In the three years that I worked for him I watched him invent so many aspects of our modern life. Jeff is a truly visionary leader and I had a front row seat to witness him preparing for this transition of power as far back as when I worked for him fifteen years ago. 

Just after I joined Jeff’s team in 2002 Andy Jassy was chosen as Jeff Bezos’ very first official “Shadow”. Jeff created this role for two main reasons. First the Shadow would provide Jeff with an intellectual sparring partner at his side in every meeting, copied on every email and on every phone call so that he would have the full context he needed in order to challenge Jeff’s ideas and keep him innovative and challenging the status quo. The Shadow was also there to learn to anticipate the questions Jeff would ask, the decisions he would make and the way in which he envisioned the company so that this young executive could go on to represent those best practices across the company when Jeff wasn’t in the room. 

I remember Andy approaching the first few days in this role with due diligence and care. He would come to my desk each morning (likely because I was the newest edition to Jeff’s C-Suite team and knew exactly how he was feeling) and ask me about the agendas for each meeting and what he might be expected to contribute. He asked me for tips on how to best collaborate with Jeff and engage with him where others had failed. I had a unique perspective sitting less than three feet from Jeff’s own desk and watching all of his engagements day after day. 

I watched Andy pour over all of the briefing documents and meticulously prepare. He was a very fast study and quickly rose to the challenge given to him. I saw how his interactions with Jeff changed dramatically as he leaned into his role without fear or apology for what he didn’t yet know and focused on learning as much and as fast as possible. 

Andy gave me one of the most important lightbulb moments of my life. I realized that I had access to the exact same things he did; the briefings, the executives, and most importantly to Jeff himself. I decided that I too could choose to approach my job in a similar way and to learn and contribute something new and more impactful every single day. It didn’t matter what our titles were. I took what otherwise could have been a reactionary, invisible role as his EA and elevated it far beyond the traditional job description. I learned to push myself outside of my comfort zone every single day. All I had to do was give myself permission. 

I learned to anticipate every question that Jeff would ask, think the way he thinks and hold my projects to his exacting standards. What a gift! But after nearly two decades of implementing this strategy I have discovered that the most important element of my career growth wasn’t actually my proximity to these tech giant CEOs. The most important factors in creating a career which has consistently levelled up and brought me joy and challenges that have exceeded my wildest dreams are accessible to anyone who wants it. It comes down to creating opportunities to be the Shadow over and over again. 

In retrospect I can see that three things were key in my evolution. First, I knew what I wanted to learn and experience at each stage. I am a big believer that your career should give as much to you as you give to it (which for me is a very high bar). The reward I wanted in exchange for my tireless effort was learning as much as possible in revolutionary environments. Second, I knew who I wanted to be and sought out managers who were leaders like whom I wanted to become. And third, I knew where I wanted to go. 

I got this clarity from consistently writing down my “dream resume” that I hope to have at the end of my life. I include all the milestones of what I want to have accomplished, learned, experienced and created. Most importantly this dream resume has absolutely nothing to do with titles. It is a resume of skills learned, risks taken and contributions made.

Absolutely anyone, regardless of their seniority or industry can take control of their trajectory by having clear answers to these questions. 

I fully expect that this next chapter of Jeff Bezos’ career will be even more impactful than the last 2 decades he spent as Amazon’s CEO - and I am fully aware of what a big statement that is. I was Eric Schmidt’s Chief of Staff at Google for over 9 years and saw how his transition from CEO to Executive Chairman gave him an opportunity to 10X his impact. He was no longer bridled to headquarters and could expand his influence and sources of inspiration much broader. I expect that Jeff’s many “side hustle” ventures will have astronomical results now that he is free to dedicate more time to them and apply his visionary leadership more broadly. And if Jeff Bezos and Eric Schmidt can up-level at their level - then I have absolutely no excuse not to do so myself! 

I have never been in the shadows because I decided to be the Shadow. And so can you.