Aug 18, 2024 · 1h 28m · lennys-podcast
Unorthodox PM tips: Automating user insights, unselling candidates, decision logs, more | Kevin Yien
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this interview, product leader Kevin Yien shares unconventional frameworks for high-impact product management, including maintaining decision logs to build product sense, automating direct customer research pipelines, and utilizing unsell emails to improve hiring retention. He emphasizes the importance of deep craftsmanship, writing clarity, and finding the right organizational habitat to maximize builder potential.
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 28.3% of the talking time here. How this is scored →
Lenny as informed peer 3.1 Guest teaching 5.3 Guest disagreement 1.6 Lenny pushing back 0.9
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 54:15 No PM should settle for bent glass
Kevin dismisses the conventional PM practice of relying solely on secondary user research and reports, forcefully demanding direct exposure to raw customer interactions.
Hardest push from Lenny ▶ 34:05 Kevin pushes back on Lenny's async doc review suggestionWhen Lenny suggests allowing teammates to review documents asynchronously to save meeting time, Kevin directly rejects the framing and urges forcing people into live silent read rooms.
Biggest teaching moment ▶ 49:40 The reality and impact of the unsell emailKevin breaks down the counterintuitive mechanics of front-loading candidate fears at offer stage and explains why losing 30 percent of candidates upfront prevents catastrophic retention failures.
Lenny holds their own ▶ 9:55 Lenny cites Snap's delayed PM hiring milestoneLenny demonstrates his deep industry knowledge by citing Snap's 200-person milestone before hiring its first PM to illustrate how technical teams handle product tasks early on.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| Episode Preview and Key Themes | 1 | 1 | 1 | 0 | Lenny sets up the episode with clips and an introduction before engaging in friendly banter about Kevin's long-standing Twitter avatar. | |
| Why Aspiring PMs Should Start in Other Roles | 3 | 4 | 2 | 1 | Kevin lays out his unconventional thesis that aspiring PMs should start as engineers, designers, or salespeople to understand conversion of potential energy. Lenny actively listens and sets up the premise. | |
| When Companies Need Product Managers | 6 | 4 | 2 | 2 | Lenny shares his own definition of product management and adds the example of Snap waiting until 200 employees to hire PMs. Kevin builds on this by identifying when founders/builders build for themselves. | |
| Ideal Pre-PM Career Paths | 4 | 5 | 2 | 1 | Lenny notes his own transition from engineering to PM because he was not world-class, prompting Kevin to reframe the dynamic away from settling and toward doubling down on unique strengths. | |
| How to Improve Writing Craft and Cadence | 5 | 5 | 2 | 1 | Lenny quotes Joan Didion and cites Paul Graham and writing craft books to explore how PMs can write more compellingly, while Kevin breaks down sentence cadence. | |
| Defining the Perimeter and Working Across Swim Lanes | 3 | 6 | 3 | 1 | Kevin challenges conventional strict swim lanes between PM, design, and engineering, advocating for murky overlaps and setting the problem perimeter. | |
| Deep Craft: Fine-Tuning Square POS Animation Details | 2 | 7 | 2 | 1 | Kevin shares a detailed case study of spending an entire week fine-tuning millisecond animation transitions on Square POS for restaurant workers. | |
| Creating Space for Craft and Avoiding Internal Busywork | 5 | 5 | 2 | 2 | Lenny brings in Jeff Weinstein's advice and Shreyas Doshi's LNO framework to discuss prioritization and how PMs can avoid getting bogged down in internal busywork. | |
| Applying Concrete Constraints to Product Problems | 4 | 6 | 1 | 1 | Lenny prompts Kevin to make constraints actionable, and Kevin explains how trade-offs like speed over consistency empower engineering and eliminate unnecessary decisions. | |
| The Power of Silent Doc Reviews and Rapid Feedback | 4 | 6 | 3 | 2 | When Lenny suggests allowing asynchronous doc reviews as an option, Kevin pushes back and insists on synchronous silent reads to eliminate latency in feedback loops. | |
| Developing Product Sense with a Decision Log | 2 | 6 | 1 | 1 | Kevin defines product sense simply as making good decisions with insufficient data, explaining why keeping a decision log builds foundational intuition like piano scales. | |
| Implementing Decision Logs and the Shopify Prediction Case Study | 3 | 6 | 2 | 1 | Kevin explains his note-taking structure and recounts his Shopify Shop app prediction, emphasizing that decision logging is a supplement rather than a substitute for building. | |
| Sponsor Break: Eppo | 0 | 0 | 0 | 0 | Sponsor break for Eppo featuring host monologue. | |
| Calibrating Interview Accuracy with Decision Logging | 4 | 6 | 2 | 1 | Lenny proposes applying decision logs to interviewing calibration, leading Kevin into the genesis of his controversial unsell email strategy. | |
| Deep Candidate Engagement and Managing Unsell Pushback | 4 | 6 | 3 | 1 | Kevin recounts losing 30 percent of candidates at offer stage and resisting recruiters' demands to stop sending the unsell email, emphasizing the hiring manager's personal commitment. | |
| Automating User Research and Getting Direct Customer Exposure | 2 | 7 | 3 | 1 | Kevin rejects PMs relying solely on UXR reports and insists on direct exposure to raw customer interactions using tools like User Interviews and Gong. | |
| Building Automated User Research Pipelines | 3 | 6 | 1 | 1 | Kevin details the automated pipeline connecting Gong, Slack, Zapier, Customer.io, and Calendly to automatically funnel customer interviews onto a PM's calendar. | |
| Continuous Customer Contact to Update Mental Models | 5 | 5 | 1 | 1 | Lenny cites Patrick Collison on how customer research updates internal mental models, which Kevin heartily affirms, stressing the danger of relying on outdated intuition. | |
| Failure Corner: Overcoming Layoffs and Finding Swagger | 2 | 7 | 1 | 0 | In Failure Corner, Kevin shares a vulnerable story about being laid off while his wife was nine months pregnant and how he rebuilt his professional identity and swagger at Square. | |
| Understanding Environmental Fit and Habitat in Careers | 4 | 6 | 1 | 1 | Kevin explains the distinction between lacking skill and being in the wrong corporate habitat, which Lenny reinforces with a metaphor of palm trees in Antarctica. | |
| Lightning Round: Favorite Books and Adlerian Philosophy | 3 | 6 | 1 | 1 | Kevin discusses The Courage to Be Disliked and Adlerian philosophy's focus on personal locus of control, as well as The Paper Menagerie. | |
| Lightning Round: Shows and Favorite Physical Products | 2 | 5 | 1 | 0 | Kevin reviews Physical 100, The Bear, and practical tools like magnetic trays for automotive repair. | |
| Core Life Mottos: Lessons from Kevin's Parents | 2 | 7 | 1 | 0 | Kevin shares foundational lessons from his parents: his mother's advice to connect dots looking forward and his father's challenge to always find the extra three percent beyond 100. | |
| The 97-Ounce Steak: Kevin's Competitive Eating Era | 2 | 6 | 1 | 0 | Kevin details eating a 97-ounce steak at Manny's at age 14, sharing insights on self-built web pages and offering a closing plea for kindness. |
Statements from this episode (31)
Yien: Aspiring PMs Should Start in Engineering, Design, or Sales
“And when you're just getting started with a new product, the people that should be doing that are the people who are building it, right? That's an engineer. That's a designer. That's a salesperson or a support person. They're the front line of the smallest loo…”
Yien: Developer and designer-focused companies do not need dedicated product managers
“The broader point is that truly not every team needs a product manager, but the activities, the outcome that one would drive needs to get done no matter what. And in some cases, this is why the prototypical companies that everyone references when they say they…”
Lenny Rachitsky: Snap Waited Until 200 Employees to Hire First PM
“Snap actually is another example where they waited, I think, till they had 200 people before they hired their first PM.”
Yien: Writing is clarity at scale and essential for product managers
“The place that this comes from for me is writing is clarity at scale, and a key component to a PM's job is creating clarity, both internally and externally.”
Yien: PMs who cannot sell their product should not build it
“And I'm working backwards from the belief that if you can't sell or support your own product, I don't trust you to build the product.”
Kevin Yien: Reading PRDs and support articles will not improve PM writing
“I explicitly do not mean read a bunch of other PM artifacts. Like you're not gonna become a better writer by reading PRDs or, you know, whatever it is. Or support articles. It needs to be Writing that compels”
Yien: Most product teams underinvest in design capacity
“Most people I would say under invest in design point blank. And when you get to a certain scale, maybe things change, but like truly, I don't think most teams have experienced what it feels like to have a really high design ratio and what that actually does to…”
Yien: The best feedback comes from reacting to concrete proposals
“The best way to get feedback from people is not by asking what they think, but to put something concrete in front of them and then have them react to it, right?”
Yien: PMs should define problem constraints rather than prescribe solutions
“PMs should be doing everything in their power to draw the perimeter of the space, of the problem space. And it's within that eng design, everyone else that you're working with They can go as crazy as they want, push up against the bounds, and it filled the box…”
Yien: Great products require overlapping roles rather than strict swim lanes
“I think it is tempting when we think about engineering product and design to draw these really clear swim lanes and say, you do X, I do Y, don't tread on, you know, my area, but you need these murky overlaps in order to build something really good.”
Yien: Product managers must be directly involved in micro-interaction details
“And so it's easy, I think for a PM to say, that's not my responsibility. I define the requirements, you know, Have a menu group that goes to the next level. Designer, engineer, figure it out. No way. Like, that's fully on you, and you better be involved in tho…”
Yien: Delayed Square for Restaurants launch three times to ensure product quality
“We were given a pretty strict deadline that we needed to launch by and I pushed it out three times. And that's not because of this one animation, but it's because of a series of decisions where we said, this is what we believe we need to ship. And this matters…”
Yien: Scaling Companies Naturally Pull PMs Into Internal Busywork
“As a company gets bigger, as teams get more complex, It's very easy and natural to spend more time on things that are internally focused and not externally focused, and I think we just all have to have, like, hypersensitive antenna to that so that we don't fal…”
Yien: PMs should add as many constraints as reasonable to foster creativity
“At the end of the day, you should be adding as many constraints as reasonable in order to let engineers and designers come up with the most creative solutions for whatever you're trying to do.”
Yien: Synchronous silent doc reviews iterate faster than async feedback
“The latency between a comment or question and a quick followup from the author just pushes that cycle speed really long in a way that doesn't need to be. And so when people are trying to find out, like, how do you move faster? Like this actually is one of thos…”
Kevin Yien: Product sense is making good decisions with insufficient data
“We all talk about product sense. It's this, like, super mystical thing that no one knows how to get better at. To me, it's just a fancy way of saying you can make good decisions with insufficient data, and the core of that is decisions, and so PMs need as many…”
Yien: Easiest decision log setup tags decisions and schedules future reviews
“This is not what I do, but I think it's the easiest place to start. Spin up a Google doc or a notion page, just call it daily log and then bullet point out like the date of today. And then as you're going through your day, you have a meeting, just type in the …”
Yien: Auditing hiring scorecards against employee performance exposes interview flaws
“I think some of the best companies actually do have a practice around this. Where, you know, they had a six, 1218 month check-in on new hires. And they then compare, you know, their sort of performance against level hired at and then review against the scoreca…”
Yien: Frontloading role negatives at offer stage prevents six-month attrition
“And if you can tell them that up front and they can read that whole email and still be equally excited to join, you find yourself any plus higher. But if they read that and they're like, I don't know anymore, it's way better to say, great, this is not a good f…”
Yien: Sending 'unsell emails' caused 30% of candidates to decline offers
“And when I first instituted this, I lost 30% of candidates at offer stage.”
Yien: Unsell emails only work at the final offer stage
“And so they ask, can you either not send this thing or can you send it at the very beginning? And my answer is no, because I don't know what they're afraid of yet. I have to go through the whole process to actually understand the thing that's going to potentia…”
Kevin Yien: PMs must have direct exposure to raw customer interactions
“Like, I know PM should settle for looking through bent glass, in my opinion, because whether it's a research report, whether it's something a salesperson is telling you, whether it's market research, don't care. It's been processed by someone, and PMs need dir…”
Kevin Yien: Barring PMs from customer conversations indicates structural organizational failure
“If you are in a situation where the product manager is literally not allowed to talk to a customer, There is something structurally wrong and that needs to be fixed first.”
Kevin Yien: Sales teams are research teams and PMs underutilize them
“The broader theme behind this next category is your sales team is a research team, and if you don't view them that way, you are missing out on half the value”
Yien: Relying on intuition from past customer interviews is a trap
“I can use my intuition
From the hundred interviews I've already done, I don't need to do one more interview, and that is a very tempting lie to tell yourself, because the world is changing, their lives are changing, and you need to constantly be exposed to th…”
Rachitsky: Customer research should update mental models, not dictate features
“Instead of doing user research, talking to customers, informing what to build, it's talking to user, talking to customers, informs your mental model of what the customer needs. And then that informs what to build.”
Yien: Children view generative AI models conceptually as crayons
“The concept of these image generation models is the same as a crayon to her. Like there is no difference in her mind. And that is an insane change that I can't even comprehend.”
Yien: Layoffs reflect mismatched organizational needs, not personal incompetence
“There is a difference between you not being good at something and a business or company not needing that thing at a particular moment in time, or you being very good at something, but not in the way that a company needs.”
Yien: Professional success is driven more by environmental fit than individual competence
“I've seen so many times where there's been a PM, engineer, designer, like whatever role, they cannot make it work at company A. And then you see them five years later, just killing it in company B. And you're like, did they change as a person? Did they get sup…”
Yien: Autobiographies are the ultimate cheat code for adopting mental models
“The type of book by volume that I read and get the most joy from are autobiographies and memoirs. It is just like the ultimate cheat code to spend time with people that you respect are interested by or want to learn from. Like, could you imagine what it would …”
Yien: People should buy their own domain and build handcrafted personal websites
“I really do recommend that for anyone with the curiosity and the desire, To buy your domain. Even if you're never going to write anything on it, you're never going to share it out. Just own a little piece of the internet. It feels good.”