LLenny's Podcast
← All episodes
Ethan Evans (Amazon)14 January 2024

Taking control of your career

5Frameworks
15Insights

Episode overview

Former Amazon vice president Ethan Evans explains the “magic loop,” a five-step process for aligning help for a manager with an employee’s own career goals. He discusses how senior managers can demonstrate next-level strategic leadership, how candidates can stand out through enthusiasm and business impact, and how dedicated thinking supports invention. Evans also recounts a failed Amazon Appstore launch for Jeff Bezos, drawing lessons about ownership, proactive communication, rebuilding trust, operational risk, and caring for the people behind mistakes.

Key ideas

  • The magic loop begins with performing the current job well, asking a manager how to help, doing what is requested, aligning future help with a personal goal, and repeating.
  • Career goals need not mean promotion; they can include learning a skill, changing roles, joining a stronger team, or establishing healthier boundaries.
  • Senior managers reach director and executive levels by shifting from functional execution toward strategy, influence, coordination, invention, and delegation.
  • Systematic invention requires relevant expertise, dedicated distraction-free thinking, and combining existing ideas; a small number of strong ideas can create years of valuable work.
  • Interview candidates stand out through professional presence, genuine enthusiasm, full attention, and evidence that their work produced meaningful business or customer impact.
  • After a major failure, leaders should own the problem, fix it urgently, communicate concrete plans and regular updates, and rebuild trust through subsequent performance.
  • Operational leaders should balance bias for action with reputational risk, beta testing, and awareness of whether a failure could become a damaging public headline.
  • Evans argues that remote work still has substantial room for innovation and that trust-based business relationships can sometimes outperform excessive contractual suspicion.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 17

  • Ethan EvansMentionsEthan is a former vice president at Amazon executive coach and course creator focused on helping leaders grow into Executives

    today my guest is Ethan Evans Ethan is a former vice president at Amazon executive coach and course creator

  • Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter

    Ethan thank you so much for being here and welcome to the podast

  • Marshall GoldsmithCoinedthe book by Marshall gold smith what got you here won't get you there

    I often reference the book by Marshall gold smith what got you here won't get you there

  • Thomas EdisonMentionsFord and Edison okay collaborated on an early in the I think the first decade of the 20th century an early electric car

    Edison said it's what 1% inspiration and 99% perspiration

  • Lex FridmanMentionsthis reminds me of a story I just listened to on Lex Friedman's podcast

    I was just listening to Jeff BAS on Lex Freedman

  • Bill CarrCoinedbill joined Amazon just 5 years after it was founded stayed there for 15 years

    my old boss Bill Carr who wrote working backwards

  • Elon MuskMentionsWhether you like him or not, Elon, this is similar to his um if you watch him, he has sets these really ambitious goals

    like Elon Musk Tesla he can kind of like bu off his hands

  • Jeff BezosMentionsthe Jeff Bezos thing that like the success of today was set in motion three years ago

    Jeff used to write a letter introducing new products

  • Jeff WilkeMentionshe was sort of the consummate like operator

    Jeff Wilkey the CEO of retail

  • Andy JassyMentionsAndy jass's organization which was AWS at that time

    Andy jass's organization which was AWS at that time

  • Werner VogelsMentionshis CTO a a guy named verer Vogal

    his CTO a a guy named verer Vogal said you're having a database problem

  • Sam AltmanMentionsthere's everybody has uh and had and continues to have like such deep trust in in Sam and Greg and our leadership team

    Sam Alman has a similar philosophy of just like trust people and assume it'll all be okay

  • Dan HeathCoinedthe best marketing textbook ever is Dan and Chip Heath's made to stick

    it's by chip and Dan fief and it's about the science of making better decisions

  • Chip HeathCoinedthe best marketing textbook ever is Dan and Chip Heath's made to stick

    it's by chip and Dan fief and it's about the science of making better decisions

  • Jason YimMentionssomeone I work with that you know Jason yum

    was recently brought to me by uh someone I work with that you know Jason yum

  • Naval RavikantMentionseventually I met folks like Naval ravikot and Sam Altman and Brian Armstrong and they recommended me around

    Nal racan is an angel investor responsible for Angels list

  • Taylor SheridanCoinedThe person you know producing and writing those things is incredibly talented.

    all the Taylor Sheridan uh you know um 1923 and Yellowstone

Resources · 43

  • Prime VideoMentionsproduct · Amazon

    helped invent and run Prime video the Amazon app store Prime gaming and twitch Commerce

  • Prime GamingMentionsproduct · Amazon

    helped invent and run Prime video the Amazon app store Prime gaming and twitch Commerce

  • AmazonMentionscompany · Jeff Bezos

    Ethan is a former vice president at Amazon

  • Twitch CommerceMentionsproduct · Amazon

    Prime gaming and twitch Commerce which alone is a billion doll business for Amazon

  • SidebarRecommendscompany · Sidebar

    sidebar is the missing piece to catalyze your career

  • SprigMentionssoftware · Sprig

    sprig is an AI powered platform that enables you to collect relevant product experience insights from the right users

  • FigmaUsessoftware · Figma

    next gen product teams like figma and notion rely on Sprig

  • NotionUsessoftware · Notion Labs

    next gen product teams like figma and notion rely on Sprig

  • StarbucksMentionscompany

    what your manager should do and $4 will get you a cup of coffee at Starbucks

  • AppleMentionscompany · Steve Jobs, Steve Wozniak, and Ronald Wayne

    a lot of companies Amazon Google Apple Etc were growing very rapidly

  • GoogleMentionscompany · Google

    a lot of companies Amazon Google Apple Etc were growing very rapidly

  • What Got You Here Won't Get You ThereRecommendsbook · Marshall Goldsmith

    not only because it's a great book classically on this problem but because the title tells the story

  • Working BackwardsMentionsbook · Colin Bryar and Bill Carr

    my old boss Bill Carr who wrote working backwards

  • KindleMentionsproduct · Amazon

    the Kindle a decades old idea now still getting better

  • TeslaMentionscompany · Tesla, Inc.

    like Elon Musk Tesla he can kind of like bu off his hands

  • Amazon PrimeMentionsproduct · Amazon

    Prime has expanded first it was two Day in the US then one day in the US now it's Same Day

  • ArcadeMentionssoftware · Arcade

    arcade is an interactive demo platform that enables teams to create polished on brand Demos in minutes

  • Quantum MetricUsescompany

    quantum metric the leading digital analytics platform created an interactive product tour library to drive more prospects with arcade

  • CartaUsescompany

    product 4 teams such as atlassian Carta and rol use arcade to tell better stories

  • AtlassianUsescompany

    product 4 teams such as atlassian Carta and rol use arcade to tell better stories

  • Amazon AppstoreMentionssoftware · Amazon

    I was responsible for launching Amazon's App Store

  • Amazon Web ServicesUsescompany · Amazon

    we're trying to eliminate all Oracle databases and move to AWS

  • Oracle DatabaseUsessoftware · Oracle

    we're trying to eliminate all Oracle databases and move to AWS

  • Amazon SilkMentionssoftware · Amazon

    Amazon had a browser called Silk for a while

  • Fire PhoneMentionsproduct · Amazon

    Jeff and firefoam which you know it's like his that'll be an albatross around his neck

  • MicrosoftMentionscompany · Bill Gates and Paul Allen

    basically it was a reaction I think to Microsoft where they felt Microsoft always talked about what was coming

  • Amazon Leadership PrinciplesMentionsother · Amazon

    Amazon has these leadership principles I think there's 14 of them

  • Blue OriginMentionscompany · Jeff Bezos

    with blue origin he wants it to be decisiveness basically leaning into this bias reaction

  • PayPalUsescompany · Max Levchin, Peter Thiel, and Luke Nosek

    they pay me through PayPal and I do good coaching for them

  • DecisiveRecommendsbook · Chip Heath and Dan Heath

    my number one recommendation is a book called decisive

  • Leadership and Self-DeceptionRecommendsbook · The Arbinger Institute

    my second most recommended book is leadership and self-deception

  • The Arbinger InstituteCoinedcompany

    it's by a group a research group called The arbinger Institute

  • AngelListCoinedcompany · Naval Ravikant and Babak Nivi

    Nal racan is an angel investor responsible for Angels list

  • The Almanack of Naval RavikantRecommendsbook · Eric Jorgenson

    that book is the almanac of racan

  • 1923Recommendstv show · Taylor Sheridan

    all the Taylor Sheridan uh you know um 1923 and Yellowstone and I I all of those series of we've watched everything

  • YellowstoneRecommendstv show · Taylor Sheridan and John Linson

    all the Taylor Sheridan uh you know um 1923 and Yellowstone and I I all of those series of we've watched everything

  • Chuckit!Recommendsproduct

    my favorite product that I've discovered recently is the Chuck it which you use to whip a ball for your dog

  • ChatGPTMentionssoftware · OpenAI

    it's too easy to say chat GPT and stuff so I won't go there

  • LinkedInUseswebsite · LinkedIn

    the best place to find me online I do all my writing on LinkedIn

  • SubstackUseswebsite · Substack Inc.

    I do have a substack newsletter

  • MavenUseswebsite · Maven

    I do teach through the maven platform

  • Stuck at Senior Manager: Breaking Through to ExecutiveCoinedcourse · Ethan Evans

    I teach a course that's been very popular called stuck at senior manager breaking through to Executive

  • Lenny's PodcastMentionspodcast · Lenny Rachitsky

    you can find all past episodes or learn more about the show at lenp podcast.com

Spot an error or want something removed? Request a correction or removal.

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 4

Hot Take11:30

"What Your Manager Should Do and $4 Gets You a Coffee"

Ethan pushes back on the objection that a good manager should notice your work and drive your career for you. His point: a good manager technically should, but many aren't good or are too busy, so waiting for them is a losing bet. The whole value of his approach is that it puts career growth inside your own control.

  • A good manager would help your career, but not all managers are good and many are just busy.
  • Being upset your manager isn't perfect is wasted energy; take control of your own situation instead.
  • Managers can also initiate the same partnership from their side with their employees.

that is what your manager should do and $4 will get you a cup of coffee at Starbucks

Ethan Evans · 11:30
#career#management#ownership#promotion
Hot Take33:30

You Only Need a Few Ideas — The Rest Is Optimization

Ethan argues that reputations as great inventors come from very few ideas expressed relentlessly over years, not a constant stream of novelty. He says you only need about two hours of dedicated thinking a month, because one good idea takes years to fully express. Prime is his example: a single idea that keeps compounding through incremental optimization.

  • Invention time is small — roughly two hours once a month; expressing an idea takes years.
  • You don't need many good ideas to be seen as highly inventive.
  • Most of the real work and value is incremental optimization, not the initial idea.
  • Prime started as fast free shipping and grew into ~25 bundled benefits over time.

so the point here is you don't need very many good ideas to be seen as tremendously invented

Ethan Evans · 34:00

there's actually something like 25 things you get free with prime most people have no idea

Ethan Evans · 35:30
#invention#innovation#amazon#product
Hot Take1:09:00

Contrarian: Remote Work Will Win Long-Term

Against the return-to-office movement favored by many leaders at his level, Ethan bets on remote work because of innovation headroom. Offices have had about 300 years to be optimized and have little left to improve, while remote work is only a few years old and largely unexplored. He has far more faith in the upside of improving the remote experience.

  • The first purpose-built office was built in 1726 in London — ~300 years of optimization.
  • Offices have little room left to improve; remote work is barely explored.
  • 'Back to office because we know it works' undervalues remote's improvement potential.
  • He predicts remote work trends up over the long term.

the first purpose-built office the first building ever built to be an office was built in 1726 in London

Ethan Evans · 1:09:30
#remote-work#future-of-work#contrarian#innovation
Hot Take1:10:30

Contrarian: Do Business on a Handshake

Ethan argues that too much of the world runs on contracts and has lost the idea of your word being your bond. Most of his coaching clients have no contract and pay through PayPal, and he delivers anyway. He accepts he'll occasionally get burned, but believes chronic suspicion of people carries a higher cost.

  • Most of his coaching happens with no NDA or contract, paid via PayPal.
  • The world is over-reliant on contracts at the expense of trust.
  • Getting occasionally burned is cheaper than treating everyone as suspect.
  • Lenny notes Sam Altman holds a similar trust-first philosophy.

I think too much of the world is contract driven and we've lost the idea of your word being your bond

Ethan Evans · 1:11:00
#trust#business#contrarian#relationships

Explainer· 3

Explainer17:30

Why Helping Your Boss Actually Advances Your Career

Ethan explains the underlying mechanism behind his career advice: managers are rarely offered help and often feel overwhelmed and alone, so an ally lifts a huge weight off them. The deeper lever is basic reciprocity — we help the people who help us — built into human behavior. Leaning gently into that instinct is why the approach works so reliably.

  • Management can be a lonely job; managers feel responsible for everything and rarely get offered help.
  • The mechanism is simple reciprocity: people help those who help them.
  • Many manager relationships are oppositional; flipping that to 'you help me, I'll help you' changes the dynamic.

management can be a lonely job because you feel like you're responsible for everything

Ethan Evans · 17:30

the social engineering here is just the simple you help me I'll help you like it doesn't have to be exploitative it's just we help…

Ethan Evans · 18:00
#career#management#psychology#influence
Explainer23:00

Why People Get Stuck at Senior Manager

Ethan breaks down why the jump from senior manager to director is a common plateau. There's a structural choke point (few director slots), worsened by a lean economy that no longer floats people up on growth. But the real block is that the skills that make you a strong senior manager — being excellent in your function and getting things done — aren't what the next level rewards.

  • There are far fewer director roles than senior managers, creating a structural choke point.
  • In a growing company you can 'ride the elevator' up as teams expand; lean times remove that lift.
  • Director and VP work is about influence, coordination, and letting go of the details, not personal execution.
  • He references Marshall Goldsmith's 'What Got You Here Won't Get You There' as the core problem.

I was in some sense just riding the elevator like the elevator was going up and as long as I managed to stay on it…

Ethan Evans · 24:00

all the great traits that got you to this one level kind of won't get you to the next level where you're more expected to…

Ethan Evans · 25:00
#career#promotion#leadership#management
Explainer36:30

The Two Things That Make You Stand Out in Interviews

Having interviewed over 2,200 people, Ethan says the top two factors in any interview are appearance and enthusiasm — show up looking interested and be genuinely excited to be there. He wants the offer even if he's decided he doesn't want the job. Beyond that, the biggest miss at senior levels is candidates describing what they did instead of why it mattered.

  • Appearance and enthusiasm are the number one and two interview factors — people want to work with people who want to work with them.
  • Come in leaned-in and enthusiastic; aim to win the offer even if you'd decline it.
  • Higher-level candidates talk about the work they did but not the impact it had.
  • Leaders hire to solve a problem, so show impact, not just effort.

the number one and two factors in any interview are appearance and enthusiasm

Ethan Evans · 36:30

people talk about what they have done but not why it mattered they don't talk about the impact

Ethan Evans · 37:00
#interviews#hiring#career#leadership

Story· 4

Story30:00

How Ethan Got 70+ Patents by Combining Two Existing Things

Faced with Amazon's 'invent and simplify' principle, Ethan taught himself to invent systematically rather than waiting for inspiration. His method: be an expert in the area, then set dedicated device-free time to think, and combine two things that already exist. His example — a truck-and-drone delivery patent — came from mashing up drones with the idea of an aircraft carrier.

  • Invention is learnable, not pure magic; Edison's '1% inspiration, 99% perspiration' applies.
  • You need real expertise in the area plus dedicated, distraction-free thinking time.
  • The easiest way to invent is to combine two existing things rather than create something wholly new.
  • His drone-delivery patent uses a topless truck as a mobile base, inspired by an aircraft carrier.

the most straightforward way to invent is not to somehow come up with something completely new but instead to put together two things that exist

Ethan Evans · 31:00

I loved military history and so I was thinking also about an aircraft carrier and I was thinking like is there a way to have…

Ethan Evans · 31:30
#invention#innovation#amazon#creativity
Story41:00

Failing Jeff Bezos on Launch Day and Surviving

As a director launching Amazon's App Store, Ethan's team hit 6am launch time with the marquee 'test drive' feature still broken and a Jeff Bezos launch letter waiting to go live. Bezos woke up, started emailing, and escalated as executives piled onto an increasingly angry thread. AWS principal engineers eventually threw 500 machines at the flawed database design to make it run, but the media moment was lost.

  • The team worked all night and was still debugging the 'test drive' feature at 6:15am.
  • Bezos emailed asking where the letter was, then escalated to Ethan's boss and the retail CEO.
  • The root cause was a flawed Oracle database design Amazon was trying to eliminate.
  • AWS engineers brute-forced a fix with ~500 machines; Bezos lost trust and checked the system himself over the weekend.

what I'm thinking in my head is get in the shower get in the shower I just need 20 minutes

Ethan Evans · 43:00

so I was buying life one hour at a time

Ethan Evans · 45:00
#failure#amazon#leadership#jeff-bezos
Story58:30

The Regret: The New Grad Who Left After the Bug

The code that failed in front of Bezos was written by a new college-grad engineer who'd been left alone on part of the UI without help or oversight. Shortly after the disaster he left the company. Ethan's biggest regret isn't catching the bug sooner — it's not reaching out to reassure that engineer that the system failed him, not the other way around.

  • A new-grad engineer wrote the non-scaling code after being left unsupervised.
  • He left the company soon after, carrying undue responsibility for the failure.
  • Ethan's real regret is failing to support the human behind the bug.
  • The lesson is to notice and be there for people struggling silently after a mistake.

yes you wrote the bug but that's not on you like the system failed you

Ethan Evans · 59:30

he felt undue responsibility I think

Ethan Evans · 1:00:30
#leadership#empathy#management#failure
Story1:00:30

Writing "An Owner Never Says That's Not My Job"

When Amazon merged its lists into a single set of leadership principles, 'ownership' was dropped and a group of directors — including Ethan — pushed to restore it. Asked to draft language, Ethan proposed the line 'an owner never says that's not my job,' which survived into the official, still-current principle. With ~1.5M employees living by these principles, he calls it the most impactful thing he's ever written.

  • Ownership was cut when Amazon merged three lists into one; directors flagged the omission.
  • Ethan drafted the phrase 'an owner never says that's not my job.'
  • The line was modified but kept and remains in the principle today.
  • You can influence far up a company if your ideas are good.

an owner never says that's not my job

Ethan Evans · 1:02:00

it's probably the most impactful thing I've ever written

Ethan Evans · 1:03:00
#amazon#leadership-principles#ownership#influence

Tool· 1

Tool1:12:00

Ethan's Most-Recommended Books

In the lightning round, Ethan shares his three most-recommended books: 'Decisive' by Chip and Dan Heath on the science of better decisions, 'Leadership and Self-Deception' by the Arbinger Institute on how we cause interpersonal problems and blame others, and 'The Almanack of Naval Ravikant' for its emphasis on doing what you uniquely love rather than copying others.

  • 'Decisive' (Chip and Dan Heath) — the science of making better decisions, applied at work and in life.
  • 'Leadership and Self-Deception' (Arbinger Institute) — how you're part of your own interpersonal problems.
  • 'The Almanack of Naval Ravikant' — find what you uniquely do best rather than copying anyone.
  • Your defensible career value is being uniquely you.

my number one recommendation is a book called decisive it's by chip and Dan fief

Ethan Evans · 1:12:00

he says no one can be a better version of you don't try to copy me

Ethan Evans · 1:13:30
#books#recommendations#decision-making#leadership

Takeaway· 3

Takeaway27:30

Bosses Are Motivated to Promote You

Ethan reframes the common belief that bosses hold people down. As a leader, he wanted the strongest possible reports because capable people who can do more of his job are the only way he gets to do less of it. Doing the next-level job before you're given the title makes the promotion decision easy for everyone.

  • 'Do the job before you have the job' — demonstrate the level before you're granted it.
  • Leaders have a selfish incentive to promote strong people: it lets them do less of their own job.
  • The narrative that bosses are holding you down is mostly wrong for good managers.

why wouldn't I want stronger more capable direct reports why wouldn't I want people under me who could do more of my job frankly that's…

Ethan Evans · 28:00
#career#promotion#management#mindset
Takeaway44:00

How to Dig Out of a Public Failure

Ethan's playbook for surviving a high-visibility disaster: own it completely with no deflection, then proactively update leadership on a fixed cadence to hold off micromanagement and rebuild trust an hour at a time. The most powerful move was taking it in person — anger is easy over email but hard to sustain face to face, which is where relationships get repaired.

  • Own the failure outright: 'it's my fault, I will deal with it.'
  • Proactively update on a schedule (e.g. every hour) so leaders don't jump in and micromanage.
  • Rebuild trust incrementally rather than all at once.
  • Take the conversation in person — it's much harder to stay angry face to face than over email.

so the first thing I did was I owned it I said yes it's it's it's not working it's my fault I will deal with…

Ethan Evans · 44:30

angry emails are easy stitting free feet from someone and being angry with them face to face is hard

Ethan Evans · 49:00
#failure#leadership#communication#trust
Takeaway56:30

"Fear the New York Times Headline"

After the launch failure, Ethan — a self-described 'operational cowboy' who liked to move fast and loose — realized that speed at Amazon's scale carries public risk. He adopted a mental check: would this action generate a New York Times headline? It's not about being paralyzed, but about knowing when a mistake will land on Wall Street Journal and CNN instantly.

  • At scale, an outage becomes public news immediately across major outlets.
  • He taught himself and his team to ask whether an action could produce a bad headline.
  • The goal is calibrated caution, not paralysis.

so I taught myself a new phrase which was Fear The New York Times headline

Ethan Evans · 56:30
#leadership#risk#amazon#decision-making