Nov 20, 2022 · 1h 4m · lennys-podcast

What it takes to become a top 1% PM | Ian McAllister (Uber, Amazon, Airbnb)

Ian McAllister · 45m spoken Lenny Rachitsky · 14m spoken
0:00 / 0:00
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In this episode, veteran tech leader Ian McAllister joins Lenny Rachitsky to break down the frameworks, essential skills, and leadership mindsets that distinguish top 1% product managers. Drawing from his extensive experience at Amazon, Airbnb, and Uber, McAllister shares practical insights on career progression, earning cross-functional trust, and executing Amazon's working backwards methodology.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 25.5% of the talking time here. How this is scored →

Lenny as informed peer 3.7 Guest teaching 3.5 Guest disagreement 0.4 Lenny pushing back 0.5
05100:0015:0030:0045:001:00:003:55–8:13 · Lenny as informed peer 4/10 The Power and Reach of Writing Online Lenny opens by discussing Ian's classic Quora post and articulates how writing clarifies one's thinking, citing a well-known quote attributed to Mark Twain and Hemingway. Ian completely agrees and elaborates on how writing sharpened his communication skills at Amazon.8:14–10:57 · Lenny as informed peer 4/10 Ian McAllister's Career Path and Background Ian details his career path across Microsoft, Amazon, and Uber. Lenny points out a common thread around autonomy and AI, which Ian gently adjusts by emphasizing broad e-commerce platforms and reminding Lenny of their shared time at Airbnb.10:57–14:33 · Lenny as informed peer 3/10 Key Attributes of a Top 1% Product Manager Ian runs through his comprehensive list of attributes separating top 1% product managers from top 10% PMs. Lenny prompts him to lay out the framework before drilling into specific traits.14:33–23:06 · Lenny as informed peer 5/10 Core Skills for New PMs: Communicate, Prioritize, Execute Ian explains why communication, prioritization, and execution are the core pillars for junior PMs. Lenny synthesizes the insight by observing that new PMs should actively not stress about the remaining advanced attributes early on, which Ian affirms.23:06–31:54 · Lenny as informed peer 5/10 Advanced Skills for Senior PMs: Think Big, Trust, Impact Lenny pushes back gently on Ian's placement of impact as a senior PM trait, asking whether impact isn't actually the soup all PMs swim in regardless of level. Ian clarifies how expectations shift from shipping assigned features to driving strategic business outcomes.31:55–37:35 · Lenny as informed peer 3/10 Sponsor: AssemblyAI Audio and Video APIs After a mid-roll ad read, Ian elaborates on earning trust and shares a vulnerable story from his time at Airbnb where he failed to build sufficient cross-functional alignment with customer support leadership. Lenny prompts him for the key learning, which Ian reframes as continuous improvement rather than just getting something wrong.37:36–46:37 · Lenny as informed peer 3/10 Amazon's Culture and Leadership Under Bezos and Wilkie Ian gives a masterclass on Amazon's culture, contrasting Jeff Bezos's encouraging innovation reviews with Jeff Wilkie's rigorous operational Weekly Business Reviews (WBRs). Lenny acts primarily as an engaged interviewer eliciting management wisdom.46:39–58:56 · Lenny as informed peer 4/10 Mastering the Working Backwards Framework Ian educates Lenny on common misapplications of the Working Backwards framework, pointing out that teams often retrofit customer problems to preconceived technical solutions. Lenny explores whether the press release artifact is essential or just a mental model, and Ian clarifies that the problem-obsessed mindset is the true core.58:57–1:03:25 · Lenny as informed peer 4/10 Lightning Round: Recommendations and Influences Lenny navigates through a friendly lightning round covering book recommendations, podcasts, and interview questions. Lenny contributes relevant anecdotes, including an Olympic javelin thrower learning on YouTube.1:03:25–1:04:33 · Lenny as informed peer 2/10 Connecting with Ian and Final Thoughts Ian shares his contact handles and newsletter. Lenny closes out the episode by noting how their professional relationship began through online writing ten years prior.3:55–8:13 · Guest teaching 2/10 The Power and Reach of Writing Online Lenny opens by discussing Ian's classic Quora post and articulates how writing clarifies one's thinking, citing a well-known quote attributed to Mark Twain and Hemingway. Ian completely agrees and elaborates on how writing sharpened his communication skills at Amazon.8:14–10:57 · Guest teaching 1/10 Ian McAllister's Career Path and Background Ian details his career path across Microsoft, Amazon, and Uber. Lenny points out a common thread around autonomy and AI, which Ian gently adjusts by emphasizing broad e-commerce platforms and reminding Lenny of their shared time at Airbnb.10:57–14:33 · Guest teaching 4/10 Key Attributes of a Top 1% Product Manager Ian runs through his comprehensive list of attributes separating top 1% product managers from top 10% PMs. Lenny prompts him to lay out the framework before drilling into specific traits.14:33–23:06 · Guest teaching 4/10 Core Skills for New PMs: Communicate, Prioritize, Execute Ian explains why communication, prioritization, and execution are the core pillars for junior PMs. Lenny synthesizes the insight by observing that new PMs should actively not stress about the remaining advanced attributes early on, which Ian affirms.23:06–31:54 · Guest teaching 4/10 Advanced Skills for Senior PMs: Think Big, Trust, Impact Lenny pushes back gently on Ian's placement of impact as a senior PM trait, asking whether impact isn't actually the soup all PMs swim in regardless of level. Ian clarifies how expectations shift from shipping assigned features to driving strategic business outcomes.31:55–37:35 · Guest teaching 4/10 Sponsor: AssemblyAI Audio and Video APIs After a mid-roll ad read, Ian elaborates on earning trust and shares a vulnerable story from his time at Airbnb where he failed to build sufficient cross-functional alignment with customer support leadership. Lenny prompts him for the key learning, which Ian reframes as continuous improvement rather than just getting something wrong.37:36–46:37 · Guest teaching 6/10 Amazon's Culture and Leadership Under Bezos and Wilkie Ian gives a masterclass on Amazon's culture, contrasting Jeff Bezos's encouraging innovation reviews with Jeff Wilkie's rigorous operational Weekly Business Reviews (WBRs). Lenny acts primarily as an engaged interviewer eliciting management wisdom.46:39–58:56 · Guest teaching 7/10 Mastering the Working Backwards Framework Ian educates Lenny on common misapplications of the Working Backwards framework, pointing out that teams often retrofit customer problems to preconceived technical solutions. Lenny explores whether the press release artifact is essential or just a mental model, and Ian clarifies that the problem-obsessed mindset is the true core.58:57–1:03:25 · Guest teaching 2/10 Lightning Round: Recommendations and Influences Lenny navigates through a friendly lightning round covering book recommendations, podcasts, and interview questions. Lenny contributes relevant anecdotes, including an Olympic javelin thrower learning on YouTube.1:03:25–1:04:33 · Guest teaching 1/10 Connecting with Ian and Final Thoughts Ian shares his contact handles and newsletter. Lenny closes out the episode by noting how their professional relationship began through online writing ten years prior.3:55–8:13 · Guest disagreement 0/10 The Power and Reach of Writing Online Lenny opens by discussing Ian's classic Quora post and articulates how writing clarifies one's thinking, citing a well-known quote attributed to Mark Twain and Hemingway. Ian completely agrees and elaborates on how writing sharpened his communication skills at Amazon.8:14–10:57 · Guest disagreement 1/10 Ian McAllister's Career Path and Background Ian details his career path across Microsoft, Amazon, and Uber. Lenny points out a common thread around autonomy and AI, which Ian gently adjusts by emphasizing broad e-commerce platforms and reminding Lenny of their shared time at Airbnb.10:57–14:33 · Guest disagreement 0/10 Key Attributes of a Top 1% Product Manager Ian runs through his comprehensive list of attributes separating top 1% product managers from top 10% PMs. Lenny prompts him to lay out the framework before drilling into specific traits.14:33–23:06 · Guest disagreement 0/10 Core Skills for New PMs: Communicate, Prioritize, Execute Ian explains why communication, prioritization, and execution are the core pillars for junior PMs. Lenny synthesizes the insight by observing that new PMs should actively not stress about the remaining advanced attributes early on, which Ian affirms.23:06–31:54 · Guest disagreement 1/10 Advanced Skills for Senior PMs: Think Big, Trust, Impact Lenny pushes back gently on Ian's placement of impact as a senior PM trait, asking whether impact isn't actually the soup all PMs swim in regardless of level. Ian clarifies how expectations shift from shipping assigned features to driving strategic business outcomes.31:55–37:35 · Guest disagreement 1/10 Sponsor: AssemblyAI Audio and Video APIs After a mid-roll ad read, Ian elaborates on earning trust and shares a vulnerable story from his time at Airbnb where he failed to build sufficient cross-functional alignment with customer support leadership. Lenny prompts him for the key learning, which Ian reframes as continuous improvement rather than just getting something wrong.37:36–46:37 · Guest disagreement 0/10 Amazon's Culture and Leadership Under Bezos and Wilkie Ian gives a masterclass on Amazon's culture, contrasting Jeff Bezos's encouraging innovation reviews with Jeff Wilkie's rigorous operational Weekly Business Reviews (WBRs). Lenny acts primarily as an engaged interviewer eliciting management wisdom.46:39–58:56 · Guest disagreement 1/10 Mastering the Working Backwards Framework Ian educates Lenny on common misapplications of the Working Backwards framework, pointing out that teams often retrofit customer problems to preconceived technical solutions. Lenny explores whether the press release artifact is essential or just a mental model, and Ian clarifies that the problem-obsessed mindset is the true core.58:57–1:03:25 · Guest disagreement 0/10 Lightning Round: Recommendations and Influences Lenny navigates through a friendly lightning round covering book recommendations, podcasts, and interview questions. Lenny contributes relevant anecdotes, including an Olympic javelin thrower learning on YouTube.1:03:25–1:04:33 · Guest disagreement 0/10 Connecting with Ian and Final Thoughts Ian shares his contact handles and newsletter. Lenny closes out the episode by noting how their professional relationship began through online writing ten years prior.3:55–8:13 · Lenny pushing back 0/10 The Power and Reach of Writing Online Lenny opens by discussing Ian's classic Quora post and articulates how writing clarifies one's thinking, citing a well-known quote attributed to Mark Twain and Hemingway. Ian completely agrees and elaborates on how writing sharpened his communication skills at Amazon.8:14–10:57 · Lenny pushing back 1/10 Ian McAllister's Career Path and Background Ian details his career path across Microsoft, Amazon, and Uber. Lenny points out a common thread around autonomy and AI, which Ian gently adjusts by emphasizing broad e-commerce platforms and reminding Lenny of their shared time at Airbnb.10:57–14:33 · Lenny pushing back 0/10 Key Attributes of a Top 1% Product Manager Ian runs through his comprehensive list of attributes separating top 1% product managers from top 10% PMs. Lenny prompts him to lay out the framework before drilling into specific traits.14:33–23:06 · Lenny pushing back 1/10 Core Skills for New PMs: Communicate, Prioritize, Execute Ian explains why communication, prioritization, and execution are the core pillars for junior PMs. Lenny synthesizes the insight by observing that new PMs should actively not stress about the remaining advanced attributes early on, which Ian affirms.23:06–31:54 · Lenny pushing back 2/10 Advanced Skills for Senior PMs: Think Big, Trust, Impact Lenny pushes back gently on Ian's placement of impact as a senior PM trait, asking whether impact isn't actually the soup all PMs swim in regardless of level. Ian clarifies how expectations shift from shipping assigned features to driving strategic business outcomes.31:55–37:35 · Lenny pushing back 0/10 Sponsor: AssemblyAI Audio and Video APIs After a mid-roll ad read, Ian elaborates on earning trust and shares a vulnerable story from his time at Airbnb where he failed to build sufficient cross-functional alignment with customer support leadership. Lenny prompts him for the key learning, which Ian reframes as continuous improvement rather than just getting something wrong.37:36–46:37 · Lenny pushing back 0/10 Amazon's Culture and Leadership Under Bezos and Wilkie Ian gives a masterclass on Amazon's culture, contrasting Jeff Bezos's encouraging innovation reviews with Jeff Wilkie's rigorous operational Weekly Business Reviews (WBRs). Lenny acts primarily as an engaged interviewer eliciting management wisdom.46:39–58:56 · Lenny pushing back 1/10 Mastering the Working Backwards Framework Ian educates Lenny on common misapplications of the Working Backwards framework, pointing out that teams often retrofit customer problems to preconceived technical solutions. Lenny explores whether the press release artifact is essential or just a mental model, and Ian clarifies that the problem-obsessed mindset is the true core.58:57–1:03:25 · Lenny pushing back 0/10 Lightning Round: Recommendations and Influences Lenny navigates through a friendly lightning round covering book recommendations, podcasts, and interview questions. Lenny contributes relevant anecdotes, including an Olympic javelin thrower learning on YouTube.1:03:25–1:04:33 · Lenny pushing back 0/10 Connecting with Ian and Final Thoughts Ian shares his contact handles and newsletter. Lenny closes out the episode by noting how their professional relationship began through online writing ten years prior.

speaking balance: gold is Lenny, purple is the guest (3 minute bins)

0:00 · Lenny 88.7% · guest 11.3%0:00 · Lenny 88.7% · guest 11.3%3:00 · Lenny 69.4% · guest 30.6%3:00 · Lenny 69.4% · guest 30.6%6:00 · Lenny 31.4% · guest 68.6%6:00 · Lenny 31.4% · guest 68.6%9:00 · Lenny 31.8% · guest 68.2%9:00 · Lenny 31.8% · guest 68.2%12:00 · Lenny 15.1% · guest 84.9%12:00 · Lenny 15.1% · guest 84.9%15:00 · Lenny 3.6% · guest 96.4%15:00 · Lenny 3.6% · guest 96.4%18:00 · Lenny 15.2% · guest 84.8%18:00 · Lenny 15.2% · guest 84.8%21:00 · Lenny 22.7% · guest 77.3%21:00 · Lenny 22.7% · guest 77.3%24:00 · Lenny 13.3% · guest 86.7%24:00 · Lenny 13.3% · guest 86.7%27:00 · Lenny 25.6% · guest 74.4%27:00 · Lenny 25.6% · guest 74.4%30:00 · Lenny 42.6% · guest 57.4%30:00 · Lenny 42.6% · guest 57.4%33:00 · Lenny 12.8% · guest 87.2%33:00 · Lenny 12.8% · guest 87.2%36:00 · Lenny 21.8% · guest 78.2%36:00 · Lenny 21.8% · guest 78.2%39:00 · Lenny 6.4% · guest 93.6%39:00 · Lenny 6.4% · guest 93.6%42:00 · Lenny 0% · guest 100%42:00 · Lenny 0% · guest 100%45:00 · Lenny 20.8% · guest 79.2%45:00 · Lenny 20.8% · guest 79.2%48:00 · Lenny 16.4% · guest 83.6%48:00 · Lenny 16.4% · guest 83.6%51:00 · Lenny 19.7% · guest 80.3%51:00 · Lenny 19.7% · guest 80.3%54:00 · Lenny 9.9% · guest 90.1%54:00 · Lenny 9.9% · guest 90.1%57:00 · Lenny 27.7% · guest 72.3%57:00 · Lenny 27.7% · guest 72.3%1:00:00 · Lenny 28.3% · guest 71.7%1:00:00 · Lenny 28.3% · guest 71.7%1:03:00 · Lenny 46.4% · guest 53.6%1:03:00 · Lenny 46.4% · guest 53.6%
Sharpest disagreement ▶ 37:06 Ian reframes 'getting it wrong' as continuous improvement

When Lenny characterizes Ian's Airbnb takeaway as a lesson from 'getting something wrong', Ian politely pushes back on the framing, insisting it was simply a matter of identifying continuous improvement opportunities.

Hardest push from Lenny ▶ 26:38 Lenny challenges impact being reserved for senior PMs

Lenny questions Ian's taxonomy by asking why impact was placed among senior PM skills when impact is the fundamental metric across all levels of product management.

Biggest teaching moment ▶ 47:11 Ian breaks down the false execution of working backwards

Ian thoroughly educates on how teams mistake combining existing technical components for genuine customer-centric problem solving, explaining how retrofitting problems leads to failed launches.

Lenny holds their own ▶ 20:32 Lenny synthesizes the junior PM focus framework

Lenny demonstrates his deep grasp of product coaching by reframing Ian's list into an actionable rule of thumb: beginner PMs should deliberately ignore advanced competencies to master the basics first.

the scores for every segment, with the reasoning behind each
ChapterTopicLenny as informed peerGuest teachingGuest disagreementLenny pushing backWhy
The Power and Reach of Writing Online 4200 Lenny opens by discussing Ian's classic Quora post and articulates how writing clarifies one's thinking, citing a well-known quote attributed to Mark Twain and Hemingway. Ian completely agrees and elaborates on how writing sharpened his communication skills at Amazon.
Ian McAllister's Career Path and Background 4111 Ian details his career path across Microsoft, Amazon, and Uber. Lenny points out a common thread around autonomy and AI, which Ian gently adjusts by emphasizing broad e-commerce platforms and reminding Lenny of their shared time at Airbnb.
Key Attributes of a Top 1% Product Manager 3400 Ian runs through his comprehensive list of attributes separating top 1% product managers from top 10% PMs. Lenny prompts him to lay out the framework before drilling into specific traits.
Core Skills for New PMs: Communicate, Prioritize, Execute 5401 Ian explains why communication, prioritization, and execution are the core pillars for junior PMs. Lenny synthesizes the insight by observing that new PMs should actively not stress about the remaining advanced attributes early on, which Ian affirms.
Advanced Skills for Senior PMs: Think Big, Trust, Impact 5412 Lenny pushes back gently on Ian's placement of impact as a senior PM trait, asking whether impact isn't actually the soup all PMs swim in regardless of level. Ian clarifies how expectations shift from shipping assigned features to driving strategic business outcomes.
Sponsor: AssemblyAI Audio and Video APIs 3410 After a mid-roll ad read, Ian elaborates on earning trust and shares a vulnerable story from his time at Airbnb where he failed to build sufficient cross-functional alignment with customer support leadership. Lenny prompts him for the key learning, which Ian reframes as continuous improvement rather than just getting something wrong.
Amazon's Culture and Leadership Under Bezos and Wilkie 3600 Ian gives a masterclass on Amazon's culture, contrasting Jeff Bezos's encouraging innovation reviews with Jeff Wilkie's rigorous operational Weekly Business Reviews (WBRs). Lenny acts primarily as an engaged interviewer eliciting management wisdom.
Mastering the Working Backwards Framework 4711 Ian educates Lenny on common misapplications of the Working Backwards framework, pointing out that teams often retrofit customer problems to preconceived technical solutions. Lenny explores whether the press release artifact is essential or just a mental model, and Ian clarifies that the problem-obsessed mindset is the true core.
Lightning Round: Recommendations and Influences 4200 Lenny navigates through a friendly lightning round covering book recommendations, podcasts, and interview questions. Lenny contributes relevant anecdotes, including an Olympic javelin thrower learning on YouTube.
Connecting with Ian and Final Thoughts 2100 Ian shares his contact handles and newsletter. Lenny closes out the episode by noting how their professional relationship began through online writing ten years prior.

Statements from this episode (14)

Opinion
McAllister: Amazon maintained a secretive, heads-down culture around 2010
“A lot of Amazon people I sort of felt were just like so hundred percent heads down. It was a little bit of a secretive culture, not maybe like Apple, but it was pretty private.”
Ian McAllister Nov 20, 2022 ▶ 6:15
Insight
McAllister: Forecasting, executing, and measuring separates PMs from consultants
“You know, what separates product managers from consultants sometimes is you forecast and then you execute, and then you measure and validate, and that helps you build your instincts.”
Ian McAllister Nov 20, 2022 ▶ 12:13
Insight
McAllister: Pushing back effectively is essential for leadership advancement
“Pushing back effectively. This is an art and a skill, but I think your ability to do this is pretty correlated with your ability to grow and succeed as a leader, because if you say yes to everything, you're gonna go nowhere.”
Ian McAllister Nov 20, 2022 ▶ 13:54
Insight
McAllister: PMs who prioritize well generate 5x the impact
“Given the same amount of skill, intelligence, and resources, a product manager with a great Innate ability to prioritize is going to generate five X the impact of someone without that skill.”
Ian McAllister Nov 20, 2022 ▶ 18:08
Insight
McAllister: Effective PM communication requires answering first before explaining
“If you just think answer and then explain, or sometimes answer and then shut up, that actually is a tactical thing you can do to get better at communicating.”
Ian McAllister Nov 20, 2022 ▶ 21:56
Insight
McAllister: Trust is built by repeatedly setting and meeting expectations
“You know, trust is just built by repeatedly setting and meeting expectations. And I think that's a good kind of mantra to think about as a PM, like, you know, my meeting, the expectations that I set and not just doing good things, but like calling your shots, …”
Ian McAllister Nov 20, 2022 ▶ 24:37
Insight
McAllister: Executives prioritize offensive growth over risk mitigation and efficiency
“It's true that executives wake up if something drives dollars or customers or offense things. And, you know, it just maybe shouldn't be this way, but a little less interested in things that may be less than a risk that just the risk never happens. It comes to …”
Ian McAllister Nov 20, 2022 ▶ 28:33
Insight
McAllister: PMs should own unstaffed functions until someone else takes ownership
“And it just means, you know, you don't own marketing or you don't own this other function, but you own it until you find somebody else to own it. And so that's not necessarily thinking big in terms of scale or whatever, but in terms of how you think about your…”
Ian McAllister Nov 20, 2022 ▶ 31:05
Insight
McAllister: Correct Product Strategies Fail Without Earning Stakeholder Support
“Well, I would say that if you have a certain approach, now you may be, you believe it's the right one. It may be the right one, but if you don't build the support and the relationships, you know, that they're going to help carry that out and execute on that st…”
Ian McAllister Nov 20, 2022 ▶ 36:24
Insight
McAllister: Product leadership requires operating existing products, not just building new ones
“Being a product leader is not just about building new things. It's about, you know, how well you run, which you've already built. And if you, If you're really paying attention to the product that you operate, it will give you ideas for things you could do to d…”
Ian McAllister Nov 20, 2022 ▶ 44:27
Insight
McAllister: Leaders have more impact teaching mental models than giving prescriptive advice
“I think you'll have a lot more lasting effect if you could kind of abstract it to a degree and teach the lesson, because then that person will hopefully learn the lesson and can apply it to a bunch of future situations, and also understand the why more, and it…”
Ian McAllister Nov 20, 2022 ▶ 46:01
Insight
McAllister: Amazon's 'working backwards' method works without the PR/FAQ format
“Teach that and write some posts about with templates and things like that, because it's a great way to start of like the press release has a paragraph about the problem. That's what you write, and then you write the solution paragraph, and then the customer qu…”
Ian McAllister Nov 20, 2022 ▶ 50:51
Assertion Not checkable as stated
Jeff Bezos uses three specific criteria to evaluate new product investments
“And I sort of asked him like, what's your criteria for sort of investing in something new? And he said, well, it's like three things. One, is it a big idea? And then second, is it something we should be doing? So if maybe you have an idea, if you have this new…”
Ian McAllister Nov 20, 2022 ▶ 56:05
Insight
McAllister: Combining available tech ingredients fails the working backwards test
“The most common thing that I see that kind of tips me off is that when they talk about something, there's different pieces in the pantry, right? And they're like, we have these ingredients, we could put them together. We could add these two things together and…”
Ian McAllister Nov 20, 2022 ▶ 57:24
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