3 Elements of Executive Leadership
Be a trusted decision maker; Scale yourself to lead large orgs; Inventing and handling change
Ethan & Jason here—welcome to a paid member-only edition of Level Up: Your source for executive insights, high performance habits, and specific career growth actions.
Many subscribers expense this newsletter to their Learning & Development budget, here’s an email template to send to your manager.
Upcoming live events:
(Nov 14, today) Fireside chat with Chaitali Narla (Eng Lead at Stripe; ex-Google Director) & Jason Yoong (my operating partner) on “Career & Personal Challenges Often Faced by Women in Tech”.
(Nov 19) Seattle in-person meetup for Level Up Members. Last day to RSVP is this Friday.
To become a VP at Amazon, I had to earn Jeff Bezos’s trust in my judgment, show that I could lead hundreds of people, and prove that I could invent valuable new businesses.
In this newsletter, I will tell you how you can do those 3 things.
The first thing to know is that each of these key elements boils down to something simple (not easy):
Becoming a trusted decision-maker means making correct decisions almost all the time, and course correcting when a decision does not work out. I share the exact process to do this lower down in section 1 of this newsletter.
Leading large organizations requires scaling yourself to stay on top of dozens of separate teams. To do this, you must teach your leaders to recognize and feed you the right information. Then, you must get good at diving in to audit when needed. I talk about how you can do this in section 2.
There is a process for inventing at scale. I never thought of myself as inventive, but I now have over 70 issued patents and I helped start key Amazon businesses like Twitch Commerce, Prime Gaming, and Merch by Amazon, all billion-dollar businesses today. I explain how I learned to invent at this scale in section 3.
This newsletter will be a quick look at each of these essential elements of executive leadership. In my live online course, Stuck at Senior Manager: Breaking Through to Executive, I go into far more detail about each of these areas. The course also provides students with 4+ hours of live Q&A to ask their own questions on these topics, and then a whole hour focused specifically on implementing these three things into daily work.
All this material is still less than 20% of the total course, and these are just the key topics in personal performance. The course also covers how executives lead their teams, how they participate on the executive team, and how they manage the promotion process.
The next cohort is from January 11 through February 14. If you read the tips here and want more, consider joining us.
Now, here’s the newsletter.
Section One: Trusted Decision Maker
As a Director at Amazon, I owned and built our first Appstore. Jeff Bezos was personally interested in the product launch, and when the product failed upon release, he lost faith in my judgment. It took me two years to restore his trust in me before I was promoted to Vice President (read the story). Trust is built by consistent performance over time, and that failure reset my clock. But, I was able to gain the trust back over the course of a few years.
Trust is essential for leadership growth because no higher executive can take the time to second guess everything their reports are doing. You also need to be trusted by other executives, otherwise you will never be able to influence decisions.
So, how can you build trust?
Simply put, trust comes from saying what you will do, then following through and doing it. Then, you must do this enough times for leaders to know they can rely on you.
Trust also comes from regularly making the right calls. The more times you get something right, the more trust you will build. Experience will help you make good decisions when you have seen similar situations, but there is also a simple process for making good decisions when facing a new challenge.
This process has 4 steps:
Step 1
Widen your lens and gather all your options. Do not jump to the first possible choice. Instead, ask: “What else could work here?”
This is the time to get input on possibilities from a wide range of experts and advisors.
Step 2
Evaluate all of your options and narrow them down. Assign your team to do research and gather data, and then have your strongest team members help you evaluate all the information.
Step 3
This is where you make your choice, and this is where many executives stumble. They delay or avoid making a decision for fear of being wrong. This is a mistake.
While it is important to be right most of the time, it is also important to be fast. The pace of business keeps accelerating. If you wait too long, a competitor will likely rush past you.
One thing to consider when making decisions is whether a particular decision is reversible or not. Many decisions can be changed or modified after you learn more. For example, when building software, features can be added, changed, or removed. On the other hand, letting go of a key employee or supplier is much harder to undo.
If a decision is easily reversed or modified, you can make it more quickly and with less information. This is because learning as you go is not overly risky, and it allows you to move faster. Most decisions fall into this category, particularly with good planning, testing, and prototyping.
However, when a decision is required for something that cannot be tested or reversed, a good executive slows down and makes a careful choice because it needs to be right the first time.
Step 4
Step 4 is where you evaluate and adjust. Once you make the decision and start acting, you will start learning.
A common mistake is to stick to a plan even in the face of obvious problems. Instead, choose the metrics you will use to judge the progress of your plan and the times when you will assess the data and adjust the course. Establishing these measurements and dates up front will protect you from distraction and over-optimism.
By following these steps, you can make good decisions quickly and earn trust while driving results.
Finally, I want to share my number one book recommendation for decision-making. It is Decisive by Chip and Dan Heath. This book is an easy read that will help you immediately in both your professional and personal life.
Section Two: Scaling Yourself
Executives must scale to lead hundreds or thousands of employees while staying in touch with the important details. There seems to be a contradiction between high-level, strategic direction setting and being down in the details of dozens of teams. However, the responsibility of the executive role is to get the right things done quickly and well, not to get “everything” done.
At Amazon, I managed 800 people. This is far too many people to know personally. Yet, the leaders above me expected me to know the critical details of their work. This is only possible by training your leaders to recognize the information you need and proactively funnel it to you.
That means scaling requires you to develop the individuals and leaders under you to rapidly move information up, down, and across your organization. I explained to my team members that I was expected to know the key details of features, timelines, problems, and budgets for each of their areas, so they needed to provide that information to me as a weekly status and as an immediate update if something went wrong.
Once you have taught your team to relay information proactively, the next step is to know when to audit personally. There is a time to dive in yourself, and it is when the information you are getting indicates that there is a problem that is not getting solved. At that point, you dive in deeply, gather the team, and use your experience, personal skills, and positional resources to resolve the problem. Then, you extract yourself and go back to strategic work.