Lenny RAG MCP Server

{ "episode": { "guest": "Maggie Crowley", "expertise_tags": [ "Product Management", "Product Strategy", "Leadership", "Startup Operations", "Team Management", "Product Development", "Enterprise Product", "Content Creation" ], "summary": "Maggie Crowley, VP of Product at Toast, discusses the three defining traits of exceptional product managers: simplification, following up on results, and willingness to do unglamorous work. She shares a tactical framework for writing product strategy documents that map from company mission through competitive landscape to specific execution plans. Crowley challenges conventional wisdom on being data-driven, argues that product content can be dangerous if misapplied, and emphasizes that the PM role is fundamentally about delivering business results rather than executing frameworks. She draws on experience across startups, scale-ups, and enterprises including TripAdvisor, Drift, Charlie Health, and BevSpot.", "key_frameworks": [ "The three traits of great PMs: simplification, following up on results, and carrying the water", "Strategy document structure: mission, landscape, current state, opportunity, challenges, solution, plan", "One-pager structure: background/context, problem, why it matters, why it matters now", "Minto Pyramid Principle for written communication", "Rule of three for prioritization", "On Writing Well principles for simplification" ] }, "topics": [ { "id": "topic_1", "title": "Three traits that distinguish great product managers", "summary": "Maggie identifies the three most consistent traits across best PMs she's worked with: breaking things down and simplifying, following up on results to demonstrate impact, and willingness to do hard unglamorous work including sales calls, customer implementation, and project management.", "timestamp_start": "00:04:50", "timestamp_end": "00:10:54", "line_start": 22, "line_end": 69 }, { "id": "topic_2", "title": "How to develop the skill of simplification", "summary": "Practical techniques for simplifying writing and thinking include reading work aloud, using the Minto Pyramid principle (conclusion first), deleting opening paragraphs, limiting to three points maximum, and getting peer feedback from trusted colleagues.", "timestamp_start": "00:11:14", "timestamp_end": "00:20:49", "line_start": 71, "line_end": 150 }, { "id": "topic_3", "title": "The importance of following up on results and creating visibility", "summary": "Many PMs fail to follow up on shipped features and their metrics. Setting calendar reminders and proactively sharing results with leadership is rare and valuable. This practice both demonstrates competence and enables learning from outcomes.", "timestamp_start": "00:21:49", "timestamp_end": "00:24:19", "line_start": 154, "line_end": 168 }, { "id": "topic_4", "title": "Time required to develop PM expertise and when to go deep vs. job hop", "summary": "It takes 4-5+ years to truly feel confident as a PM. Staying at one company for multiple years provides more learning than frequent job changes because you see multiple cycles of the same product. Maggie stayed at Drift for almost four years and learned more than in other periods despite desire for quick promotion.", "timestamp_start": "00:24:19", "timestamp_end": "00:27:16", "line_start": 169, "line_end": 184 }, { "id": "topic_5", "title": "Carrying the water: doing the work that makes products successful", "summary": "PMs must be willing to do whatever it takes including customer support, sales calls, QA, implementation work, and project management. This unglamorous work is central to the role. As emotional center of team, PMs must maintain optimism and momentum.", "timestamp_start": "00:27:42", "timestamp_end": "00:31:42", "line_start": 187, "line_end": 210 }, { "id": "topic_6", "title": "Breaking into product management: paths and strategies", "summary": "Entry paths to PM include MBA programs, entry-level programs at big tech, lateral moves within companies, or joining startups. Getting a PM title is critical for future opportunities. Once hired, ability to ship becomes the next filter. First PM role is hardest to obtain.", "timestamp_start": "00:31:55", "timestamp_end": "00:34:36", "line_start": 214, "line_end": 225 }, { "id": "topic_7", "title": "Product strategy: comprehensive framework and structure", "summary": "Maggie outlines detailed strategy document structure starting with company mission and goals, then landscape (competitive, SWOT, risks, market dynamics), current state (product, business, technical hurdles), opportunity identification, challenges, and finally proposed solution with sequencing and resource needs. Includes executive summary upfront.", "timestamp_start": "00:35:04", "timestamp_end": "00:42:37", "line_start": 229, "line_end": 281 }, { "id": "topic_8", "title": "One-pager or spec document structure and importance", "summary": "One-pagers should start with background and context, problem statement, why the problem matters, and why it matters now. This establishes the home base for team decisions. Document should include running decisions log and links to supporting research. It's the core PM artifact.", "timestamp_start": "00:49:39", "timestamp_end": "00:52:48", "line_start": 344, "line_end": 356 }, { "id": "topic_9", "title": "Contrarian view: being data-driven is a red flag", "summary": "PMs who are too focused on quantitative data and dashboards often neglect qualitative research and user understanding. Data shows what happened but not why. The best PMs combine data with user research and good judgment, not blindly follow metrics.", "timestamp_start": "00:58:39", "timestamp_end": "01:00:58", "line_start": 412, "line_end": 423 }, { "id": "topic_10", "title": "Contrarian view: product content can be dangerous", "summary": "Product frameworks in content become dogmatic when readers believe they're the one way to do things. People lose sight of creating impact and instead focus on checking boxes of frameworks. Nuance is lost in sanitized content. Context and judgment matter more than following templates.", "timestamp_start": "01:01:20", "timestamp_end": "01:05:19", "line_start": 427, "line_end": 450 }, { "id": "topic_11", "title": "Why creating content accelerated Maggie's career and learning", "summary": "Content creation provided networking opportunities, personal brand building, employability, recruiting advantages, and most importantly forced her to deeply process and learn from her work. The act of explaining and writing about experiences created more learning than the work itself.", "timestamp_start": "01:06:11", "timestamp_end": "01:08:28", "line_start": 460, "line_end": 468 }, { "id": "topic_12", "title": "How to create authentic product content without being cringey", "summary": "Start with real questions you're working through, stay authentic, and focus on being valuable rather than building followers. Early content will be rough. Share what's actually useful to you. Avoid clickbait. Be unashamed about your interests. The best content comes from active practitioners sharing real challenges.", "timestamp_start": "01:08:44", "timestamp_end": "01:14:13", "line_start": 472, "line_end": 533 }, { "id": "topic_13", "title": "Failure case study: the worst rewrite project", "summary": "Maggie describes a multi-team product rewrite that took 2.5 years instead of 6 months, never achieved feature parity, and failed completely. Caused by skipping discovery, not writing specs, arrogance, and poor technical planning. Lesson: avoid complete rewrites of core products.", "timestamp_start": "00:56:47", "timestamp_end": "00:57:59", "line_start": 380, "line_end": 407 }, { "id": "topic_14", "title": "PM interview question: what's the worst product you've shipped", "summary": "This interview question reveals humility, learning ability, humor, and whether candidates have shipped enough to fail. Good answers show candidates can identify mistakes, laugh about them, and learn. It's more revealing than questions about successes.", "timestamp_start": "01:16:51", "timestamp_end": "01:17:29", "line_start": 571, "line_end": 573 }, { "id": "topic_15", "title": "Closing wisdom: enjoying the work and creating culture", "summary": "Product management is messier than content suggests. PMs should focus on having fun, understanding that people do weird things, and that the role offers opportunity to create culture and enjoyment within teams. This aspect is underappreciated in product discourse.", "timestamp_start": "01:14:32", "timestamp_end": "01:15:17", "line_start": 541, "line_end": 548 }, { "id": "topic_16", "title": "Lightning round: recommended books and influences", "summary": "Key recommendations include Presentation Secrets of Steve Jobs for communication, Thinking in Bets by Annie Duke for decision-making, and Scaling People by Claire Hughes Johnson for management reference. These shape Maggie's thinking on communication, decision-making, and leadership.", "timestamp_start": "01:15:27", "timestamp_end": "01:16:11", "line_start": 559, "line_end": 560 }, { "id": "topic_17", "title": "Speed skating background and parallels to product management", "summary": "Maggie was a long-track Olympic speed skater, teaching her to think in four-to-eight-year cycles, perfect skills through repetition, focus, and grind through silence before moments of visibility. These principles directly transfer to product work's long-term focus and incremental improvement.", "timestamp_start": "01:19:38", "timestamp_end": "01:20:46", "line_start": 613, "line_end": 618 } ], "insights": [ { "id": "i001", "text": "The best PMs are really good at breaking things down and simplifying. In any moment you need to find the one truly important thing you need to do, especially in big companies with competing priorities. At startups there are so many fires that picking one and sticking with it is difficult.", "context": "Discussing the first trait that distinguishes great PMs", "topic_id": "topic_1", "line_start": 25, "line_end": 26 }, { "id": "i002", "text": "Prioritization is not just a moment in time decision. It's the ability to stay with the priority, make sure it continues to be the most important thing, finish it, see that it works, and keep people excited and engaged in the project.", "context": "On what makes prioritization hard", "topic_id": "topic_1", "line_start": 31, "line_end": 32 }, { "id": "i003", "text": "Your job as a PM is to stay on that and be the person who's beating that drum over and over again. The best PMs are the ones who can do that and have the resilience and energy to stay with it.", "context": "On shipping and maintaining momentum", "topic_id": "topic_1", "line_start": 34, "line_end": 35 }, { "id": "i004", "text": "Following up on results is so rare. Really good PMs remember to follow up on results. When a PM comes back and says 'Hey, remember we did that thing, here's what happened,' that's one of the best things when looking at PMs.", "context": "On the second trait of great PMs", "topic_id": "topic_3", "line_start": 47, "line_end": 47 }, { "id": "i005", "text": "You can't be a good PM if you're not willing to do the hard boring unglamorous work of customer support, sales, marketing, writing copy, project management. Your job is to deliver a business result, and you're responsible for outcomes and results.", "context": "On the third trait: carrying the water", "topic_id": "topic_5", "line_start": 50, "line_end": 50 }, { "id": "i006", "text": "Communication and analytical ability are basics of the PM role. But strategy is only 5% of the work you do. The person who has a good strategy will not be as successful as the PM who ships more stuff, gets more reps, and has the ability to create impact.", "context": "On what makes great PMs vs. basics", "topic_id": "topic_1", "line_start": 56, "line_end": 56 }, { "id": "i007", "text": "The word ownership doesn't have the same 'oh shit' feeling as 'you're making a bet.' Making a bet means you know there's a chance the thing you're working on won't work out and you still have to be the one to do it.", "context": "On responsibility and risk in PM role", "topic_id": "topic_1", "line_start": 110, "line_end": 110 }, { "id": "i008", "text": "When you write something, read it out loud. Half the time you'll realize it's way too complicated. Or if someone comes and says they're working on something, ask them what they're trying to say and they'll often say it simply in conversation but their document is overcomplicated.", "context": "Tool for simplifying writing", "topic_id": "topic_2", "line_start": 74, "line_end": 77 }, { "id": "i009", "text": "Just say the thing that you said in conversation. There's no reason your prose in a document has to be a certain way. We're not in school. Our goal is to get things done.", "context": "On simplification in writing", "topic_id": "topic_2", "line_start": 77, "line_end": 77 }, { "id": "i010", "text": "To get better at boiling things down, get as many reps in as you can and have people review your work. Listen to them. Your boss and the founder probably know more than you about the market, so listen to them and ask them to help you simplify.", "context": "On developing simplification skill", "topic_id": "topic_2", "line_start": 80, "line_end": 80 }, { "id": "i011", "text": "Pretty much every doc you write, you can delete the first two paragraphs. Everything on the first page is 'crapola.' Don't use it.", "context": "Writing advice from Maggie's father", "topic_id": "topic_2", "line_start": 134, "line_end": 134 }, { "id": "i012", "text": "The rule of three: there's always three things or fewer, never more than three things. If you have a fourth, you have to figure out how to squish it in there because it just doesn't look right if there's four.", "context": "On prioritization and presentation", "topic_id": "topic_2", "line_start": 89, "line_end": 89 }, { "id": "i013", "text": "There's power in picking the thing that's going to have the most impact and cutting other stuff that may have some impact but is much less important. When you lump together a bunch of ideas, it dilutes everything.", "context": "On focus and prioritization", "topic_id": "topic_2", "line_start": 98, "line_end": 98 }, { "id": "i014", "text": "To be good at your job continuously at senior levels, you need people who can give you feedback. The more senior you get, the harder that is. Having peers who can give you another point of view and help you is incredibly valuable.", "context": "On building peer support network", "topic_id": "topic_2", "line_start": 143, "line_end": 143 }, { "id": "i015", "text": "Put reminders in your calendar to follow up on metrics weeks, months, and six months after launch. Share those results with whoever might care about it. It's simple to do and really high value activity.", "context": "Practical method for following up on results", "topic_id": "topic_3", "line_start": 155, "line_end": 155 }, { "id": "i016", "text": "Following up on results helps both visibility to your manager and your own learning. You'll go back and learn why something happened or why it didn't. The more you follow up and learn, the better you get every time you ship something.", "context": "Benefits of following up on results", "topic_id": "topic_3", "line_start": 166, "line_end": 167 }, { "id": "i017", "text": "You don't have to be quietly great at your job. If you're toiling in the background doing great work, you might not get what you want. Great managers are few and far between. Always make sure to share your progress because you didn't want to leave it up to chance that someone would notice.", "context": "On visibility and career progression", "topic_id": "topic_3", "line_start": 161, "line_end": 161 }, { "id": "i018", "text": "Great PMs create an aura that they've got something on their plate and they're not going to drop it. Threads are not going to be forgotten. They put something on their plate and it's complete.", "context": "Traits that inspire confidence", "topic_id": "topic_3", "line_start": 164, "line_end": 164 }, { "id": "i019", "text": "It took years to feel confident knowing what I was doing as a PM. It takes a long time to ship stuff. Spending time is really helpful and allowed me to move faster later because I had spent time grinding it out.", "context": "On timeline for PM expertise", "topic_id": "topic_4", "line_start": 172, "line_end": 176 }, { "id": "i020", "text": "When you stay at a company for a while, you get to see two or three cycles of the same product and learn more from that than hopping companies frequently because you get to see the consequences of your decisions. That's rare.", "context": "Value of staying at one company", "topic_id": "topic_4", "line_start": 176, "line_end": 176 }, { "id": "i021", "text": "Advice for getting promoted is always: create impact and that can take time. There's lots of good reasons to bounce between companies but there's value in sticking around.", "context": "Career progression advice", "topic_id": "topic_4", "line_start": 182, "line_end": 182 }, { "id": "i022", "text": "If you ever find yourself saying 'that's not my job,' that's probably a thing you should do. You probably aren't your job and it's someone else's job, but you can spend your life getting frustrated or you can just get the work done.", "context": "On doing unglamorous work", "topic_id": "topic_5", "line_start": 188, "line_end": 188 }, { "id": "i023", "text": "People who are willing to just get the work done will move faster, their products will be more successful and they probably aren't carrying around anger and crappy emotion.", "context": "On willingness to do the work", "topic_id": "topic_5", "line_start": 188, "line_end": 188 }, { "id": "i024", "text": "As a PM, you're oftentimes the emotional center of the team. It's your job to keep people motivated, excited, and bought into the project. You have to keep that optimism going and it's hard work.", "context": "On emotional leadership", "topic_id": "topic_5", "line_start": 191, "line_end": 191 }, { "id": "i025", "text": "Your job as a PM is to deliver a business result. You don't have a specific deliverable like engineers writing code or designers designing. You're uniquely positioned to fill in all gaps because no one else is incentivized to do that.", "context": "On PM job definition", "topic_id": "topic_5", "line_start": 200, "line_end": 200 }, { "id": "i026", "text": "A lot of the PM job sucks and isn't glamorous. Most of the job is boring and annoying things. You have to be able to QA products, implement with customers, sell them, find users. None of it is above you.", "context": "Unglamorous aspects of PM work", "topic_id": "topic_5", "line_start": 209, "line_end": 209 }, { "id": "i027", "text": "If you can get someone to stamp you with the product manager role, take it. Once you get that first PM job, everything gets easier. It's what they screen on.", "context": "On importance of first PM title", "topic_id": "topic_6", "line_start": 224, "line_end": 224 }, { "id": "i028", "text": "After getting a PM title, the second filter becomes: what have you shipped? It's fascinating how quickly people can't answer that question. The people who can are always several steps ahead.", "context": "What matters after first PM role", "topic_id": "topic_6", "line_start": 224, "line_end": 224 }, { "id": "i029", "text": "Write out strategy with complete transparency about mission, landscape, current state, and opportunity so that if anyone doesn't agree, they can point out where their disagreement lands. This way disagreements become about specific points of data and feedback, not personal.", "context": "On strategy documentation approach", "topic_id": "topic_7", "line_start": 242, "line_end": 242 }, { "id": "i030", "text": "You should be able to walk from company mission down to individual priority and see the logic chain and why you got there. This allows people to understand how you arrived at decisions.", "context": "On strategy transparency", "topic_id": "topic_7", "line_start": 242, "line_end": 242 }, { "id": "i031", "text": "Strategy documents can go 20+ pages with screenshots, competitor analysis, and deep market dynamics. The key is including an executive summary upfront so people get the point and can dive deeper if interested.", "context": "On strategy document length and format", "topic_id": "topic_7", "line_start": 281, "line_end": 281 }, { "id": "i032", "text": "Write the strategy document primarily for yourself to do your job effectively. Share it so others can engage deeply if they want. Your engineering and design partners will almost always engage deeply because they're also on the line.", "context": "On purpose and audience of strategy docs", "topic_id": "topic_7", "line_start": 287, "line_end": 287 }, { "id": "i033", "text": "When you finish a strategy and compare it to your roadmap, they're never the same. The roadmap is bloated with random stuff. Usually 90% of resources are committed to things that don't track against strategy.", "context": "On strategy vs. reality gap", "topic_id": "topic_7", "line_start": 310, "line_end": 314 }, { "id": "i034", "text": "The most important section in a one-pager is the first part: background and context. It allows the PM to center the team around the problem, why it exists, and why it's worth solving. This becomes the home base for team decisions.", "context": "On one-pager structure", "topic_id": "topic_8", "line_start": 348, "line_end": 350 }, { "id": "i035", "text": "In a one-pager, explicitly document decisions made: 'On this day we made this decision' or 'we decided not to do this' or 'we decided only to solve this part of the problem.' Keep a running list of this with links to supporting research.", "context": "Best practices for one-pagers", "topic_id": "topic_8", "line_start": 350, "line_end": 350 }, { "id": "i036", "text": "The 'why this problem matters now' section is important because there are many things you could do and certain things are perishable - you can only do them now or you miss the opportunity.", "context": "On timing in product decisions", "topic_id": "topic_8", "line_start": 357, "line_end": 357 }, { "id": "i037", "text": "PMs who are really excited about being data-driven often over-emphasize quantitative data at the expense of qualitative data. They probably don't do direct user research and don't understand the humans using the product.", "context": "Contrarian take on being data-driven", "topic_id": "topic_9", "line_start": 413, "line_end": 413 }, { "id": "i038", "text": "Most jobs and products benefit more from talking to 10 users than from any dashboard. You need data to understand if something works at scale, but data alone won't tell you why things are happening.", "context": "On quantitative vs qualitative data", "topic_id": "topic_9", "line_start": 413, "line_end": 413 }, { "id": "i039", "text": "If something is logically better and obviously a good idea, use good judgment and do that thing. You don't need to analyze everything - sometimes you can just do the obviously better thing.", "context": "On good judgment vs. analysis", "topic_id": "topic_9", "line_start": 422, "line_end": 422 }, { "id": "i040", "text": "Product content requires sanitizing and frameworkizing, which causes people to lose touch with the actual point which is creating impact. The best PMs build intuition and sometimes throw out all frameworks.", "context": "Risks of product content", "topic_id": "topic_10", "line_start": 428, "line_end": 428 }, { "id": "i041", "text": "Content sometimes gets in the way of impact because people try to apply frameworks and think the point is the framework or the template when it's not. The point is impact.", "context": "Content as obstacle", "topic_id": "topic_10", "line_start": 428, "line_end": 428 }, { "id": "i042", "text": "As a leader, you may find someone quoting your own content back at you. You have to know why you're not following the rules you previously advocated for.", "context": "On content creator accountability", "topic_id": "topic_10", "line_start": 431, "line_end": 431 }, { "id": "i043", "text": "Creating content forces you to think through what you did, summarize it, make it interesting, and discuss it. This process means you pay attention to what you're learning in ways you wouldn't if just working.", "context": "Learning benefit of content creation", "topic_id": "topic_11", "line_start": 467, "line_end": 467 }, { "id": "i044", "text": "Personal brand and content help with networking, access, recruitability, and recruiting. It signals who you are and how you like to work before people are on the phone with you.", "context": "Career benefits of content", "topic_id": "topic_11", "line_start": 464, "line_end": 464 }, { "id": "i045", "text": "Your first 10-20 posts are going to be cringe and that's natural. You have to get over the fact that early content is rough and it will fade away.", "context": "On starting with content creation", "topic_id": "topic_12", "line_start": 484, "line_end": 484 }, { "id": "i046", "text": "You have to be authentic and real in content. Share real questions you were working on and real advice you needed at that time. This relevance is what makes it valuable.", "context": "On authenticity in content", "topic_id": "topic_12", "line_start": 497, "line_end": 500 }, { "id": "i047", "text": "Share things that are actually useful to you. Don't create content if you haven't done the thing because people will see you don't know what you're really talking about.", "context": "On credibility in content", "topic_id": "topic_12", "line_start": 503, "line_end": 503 }, { "id": "i048", "text": "The most valuable content often comes from thinking the stuff you do is so basic it's not worth sharing, but that's often the most interesting because it's something you're really good at.", "context": "On finding content ideas", "topic_id": "topic_12", "line_start": 530, "line_end": 530 }, { "id": "i049", "text": "A strategy exercise can reveal that most of your roadmap doesn't actually track against strategy. This allows you to critically think about whether you should be doing what you're doing.", "context": "On gap between strategy and roadmap", "topic_id": "topic_7", "line_start": 314, "line_end": 314 }, { "id": "i050", "text": "A product rewrite without proper discovery and specs is extremely risky. It's easy to commit teams to it and nearly impossible to course correct once you're far along.", "context": "On failure of rewrites", "topic_id": "topic_13", "line_start": 383, "line_end": 383 } ], "examples": [ { "id": "e001", "explicit_text": "At TripAdvisor, we did product management rotation. It was my first PM job, two years with four different teams.", "inferred_identity": "Maggie's role at TripAdvisor", "confidence": "high", "tags": [ "TripAdvisor", "product management", "rotation program", "first job", "travel" ], "lesson": "Early PM roles in structured programs like rotations can teach fundamental PM skills across different products but may not prepare you for independent PM ownership", "topic_id": "topic_4", "line_start": 172, "line_end": 172 }, { "id": "e002", "explicit_text": "Went to a startup after TripAdvisor, there was another product person, they left and I was the only product person. I realized really quickly I had no idea what I was doing.", "inferred_identity": "Maggie's startup experience between TripAdvisor and Drift", "confidence": "medium", "tags": [ "startup", "solo PM", "learning", "difficult experience", "growth" ], "lesson": "Being a solo PM at a startup without mentorship is a baptism by fire that reveals gaps in knowledge that don't show up in structured environments", "topic_id": "topic_4", "line_start": 172, "line_end": 173 }, { "id": "e003", "explicit_text": "That's why I joined Drift - because that team had all these incredible product thinkers on it and they were shipping all sorts of stuff with momentum.", "inferred_identity": "Maggie's intentional move to Drift for learning", "confidence": "high", "tags": [ "Drift", "product team", "mentorship", "learning culture", "sales engagement" ], "lesson": "Choosing a company specifically for the learning opportunity and team quality can accelerate PM development more than optimizing for title or immediate impact", "topic_id": "topic_4", "line_start": 173, "line_end": 173 }, { "id": "e004", "explicit_text": "I stayed at Drift for almost four years. I got to see two or three cycles of the same product and I learned more from that than from the year or so at other places.", "inferred_identity": "Maggie's tenure at Drift", "confidence": "high", "tags": [ "Drift", "long tenure", "deep learning", "product cycles", "expertise building" ], "lesson": "Staying at one company for multiple product cycles builds expertise that job hopping cannot provide because you see consequences of decisions over time", "topic_id": "topic_4", "line_start": 176, "line_end": 176 }, { "id": "e005", "explicit_text": "When I was at my last startup, I did hire someone fresh out of business school who hadn't been into product into a PM role. We spent four months working together in a WeWork in person.", "inferred_identity": "Maggie's hiring of Christina (first PM hire from non-PM background) at Charlie Health", "confidence": "high", "tags": [ "hiring", "first-time PM", "onboarding", "startup", "mentorship", "WeWork" ], "lesson": "You can hire people without PM background into PM roles but it requires significant manager investment and only works with very engaged candidates", "topic_id": "topic_6", "line_start": 215, "line_end": 218 }, { "id": "e006", "explicit_text": "She basically just hounded me. Christina, if you're listening, you emailed me a lot. We talked a lot and we waited until the time was right and then you finally convinced me to do it.", "inferred_identity": "Christina as the candidate who pestered Maggie until hired", "confidence": "high", "tags": [ "persistence", "recruitment", "determination", "first job", "network" ], "lesson": "Getting someone to take a chance on hiring you into your first PM role requires persistence and strong communication with the hiring manager", "topic_id": "topic_6", "line_start": 218, "line_end": 218 }, { "id": "e007", "explicit_text": "An engineer at Drift who I worked with really wanted to understand why we were doing what we were doing. He was not satisfied with surface level answers. He was pushing and pushing and pushing.", "inferred_identity": "Engineer at Drift who prompted Maggie to create strategy documentation", "confidence": "medium", "tags": [ "Drift", "engineering", "stakeholder", "strategy", "questions" ], "lesson": "Engineers who push for deep understanding of strategy can be the impetus for PMs to create better documentation and thinking", "topic_id": "topic_7", "line_start": 230, "line_end": 230 }, { "id": "e008", "explicit_text": "We decided we needed to do a rewrite of an existing product. An engineer I'd worked with many times said it would take six months. It didn't take six months, it took two and a half years.", "inferred_identity": "Major rewrite project (unnamed company)", "confidence": "medium", "tags": [ "rewrite", "technical debt", "estimation", "failure", "sunk cost fallacy" ], "lesson": "Product rewrites are almost always underestimated, take much longer than expected, and often fail to deliver ROI relative to the investment", "topic_id": "topic_13", "line_start": 380, "line_end": 382 }, { "id": "e009", "explicit_text": "Adam Medros, who was a VP at TripAdvisor, in a product review meeting just said, 'This is obviously better thing. Just do it. Stop. Stop doing all this stuff. Stop with these numbers.'", "inferred_identity": "Adam Medros at TripAdvisor", "confidence": "high", "tags": [ "TripAdvisor", "leadership", "decision making", "good judgment", "data vs intuition" ], "lesson": "Sometimes the best product decisions come from good judgment about obviously better ideas rather than analysis paralysis", "topic_id": "topic_9", "line_start": 419, "line_end": 422 }, { "id": "e010", "explicit_text": "At Drift, when that became such a part of what we were doing at that time, content creation was supported and encouraged.", "inferred_identity": "Drift culture supporting PM content creation", "confidence": "high", "tags": [ "Drift", "content creation", "thought leadership", "culture", "brand building" ], "lesson": "Companies that encourage PMs to create content and build personal brands benefit from the visibility and employee engagement it creates", "topic_id": "topic_11", "line_start": 461, "line_end": 461 }, { "id": "e011", "explicit_text": "I worked in healthcare for a year and there's a Slack community organized for heads of products in healthcare startups that is really powerful.", "inferred_identity": "Healthcare PM community (inferred: Charlie Health)", "confidence": "high", "tags": [ "healthcare", "Slack community", "peer support", "head of product", "startups" ], "lesson": "Professional peer communities by industry or role provide valuable support and knowledge sharing that peer relationships within companies cannot", "topic_id": "topic_2", "line_start": 149, "line_end": 149 }, { "id": "e012", "explicit_text": "Someone was justifying a project in a product review meeting and Adam Medros said to just do it because it's obviously better.", "inferred_identity": "Anonymous project at TripAdvisor", "confidence": "low", "tags": [ "TripAdvisor", "decision making", "leadership", "judgment" ], "lesson": "The best leaders empower teams to make obvious good decisions without requiring extensive justification", "topic_id": "topic_9", "line_start": 420, "line_end": 422 }, { "id": "e013", "explicit_text": "I was working with somebody making PowerPoint presentations. I wrote out how I do it: start with outline on paper, draw boxes for slides, write headlines, then sketch slides, then go to Google Docs.", "inferred_identity": "Anonymous colleague at unnamed company", "confidence": "low", "tags": [ "presentation skills", "process", "methodology", "writing", "collaboration" ], "lesson": "Simple process improvements that seem obvious to experts can significantly improve others' productivity when explicitly shared", "topic_id": "topic_12", "line_start": 527, "line_end": 530 }, { "id": "e014", "explicit_text": "Someone said it took 75% less time using my presentation process.", "inferred_identity": "Colleague adopting Maggie's presentation methodology", "confidence": "low", "tags": [ "productivity", "methodology", "learning", "content value" ], "lesson": "Sharing your methods can have outsized impact that you don't anticipate", "topic_id": "topic_12", "line_start": 530, "line_end": 530 }, { "id": "e015", "explicit_text": "At my last role, we all had your newsletter and people would bring articles, saying 'this could help, what if we did it that way?'", "inferred_identity": "Toast team using Lenny's content", "confidence": "high", "tags": [ "Toast", "newsletter", "implementation", "learning culture" ], "lesson": "Good product content can drive teams to experiment with new approaches and frameworks", "topic_id": "topic_10", "line_start": 437, "line_end": 437 }, { "id": "e016", "explicit_text": "There was a newsletter article about Figma and templates for product review in FigJam that we love and use all the time.", "inferred_identity": "Lenny's Figma/FigJam content used at Toast", "confidence": "high", "tags": [ "Figma", "FigJam", "templates", "product review", "tools" ], "lesson": "Concrete tool templates in content get adopted and used more than abstract frameworks", "topic_id": "topic_10", "line_start": 437, "line_end": 437 }, { "id": "e017", "explicit_text": "I showed my Slack workspace of three people: me, Alexa, and Daphne. We all worked together at Drift.", "inferred_identity": "Alexa and Daphne - Maggie's peer support group from Drift", "confidence": "high", "tags": [ "Drift", "peer support", "women in product", "mentorship", "network" ], "lesson": "Staying in touch with talented peers from previous companies creates a valuable long-term support network", "topic_id": "topic_2", "line_start": 143, "line_end": 143 }, { "id": "e018", "explicit_text": "At Toast, I get to work with John Cutler, it's phenomenal.", "inferred_identity": "John Cutler as colleague at Toast", "confidence": "high", "tags": [ "Toast", "collaboration", "product leadership", "executive" ], "lesson": "Working alongside world-class practitioners accelerates learning and impact", "topic_id": "topic_1", "line_start": 635, "line_end": 635 }, { "id": "e019", "explicit_text": "I was a speed skater, long track speed skater on a 400-meter rink, just turning left and going in circles.", "inferred_identity": "Maggie as Olympic long-track speed skater", "confidence": "high", "tags": [ "Olympics", "speed skating", "athlete", "sports", "discipline" ], "lesson": "Athletic training in individual sports teaches focus, discipline, and how to perfect skills through repetition", "topic_id": "topic_17", "line_start": 614 }, { "id": "e020", "explicit_text": "As an Olympic athlete, you have to think in four or eight-year chunks. You grind for so long in silence before you get a chance to shine.", "inferred_identity": "Maggie's experience as Olympic speed skater", "confidence": "high", "tags": [ "Olympics", "long-term thinking", "patience", "discipline", "delayed gratification" ], "lesson": "Long-term thinking built through athletic training translates directly to product work which also requires years of investment before seeing big results", "topic_id": "topic_17", "line_start": 614, "line_end": 617 }, { "id": "e021", "explicit_text": "As an MBA student, I went to business school and got into a program that took MBA students for PM rotation.", "inferred_identity": "Maggie's TripAdvisor PM rotation from business school", "confidence": "high", "tags": [ "MBA", "business school", "Harvard Business School", "TripAdvisor", "hiring path" ], "lesson": "Business school PM rotation programs are a reliable path to first PM roles if you can access them", "topic_id": "topic_6", "line_start": 215, "line_end": 215 }, { "id": "e022", "explicit_text": "I use Future Fit three times a week and I love it.", "inferred_identity": "Lenny as Future Fit user", "confidence": "high", "tags": [ "fitness", "app", "personal brand" ], "lesson": "Publicly sharing product usage builds personal brand and creates authentic recommendations", "topic_id": "topic_1", "line_start": 587, "line_end": 587 }, { "id": "e023", "explicit_text": "I'm now on Ladder Fit. I don't have to talk to the coach every day, I don't need the accountability. I like the anonymity and the group chat is unhinged.", "inferred_identity": "Maggie as Ladder Fit user", "confidence": "high", "tags": [ "fitness", "app", "community", "product recommendation" ], "lesson": "Different products serve different needs and self-knowledge about what you need (accountability vs anonymity) drives product choice", "topic_id": "topic_1", "line_start": 590, "line_end": 596 }, { "id": "e024", "explicit_text": "I'm a new mom. There's this app called Pump Log. It does one thing incredibly well and there's not a single thing I wish it did. I paid $14 for it, never paid for an app like that.", "inferred_identity": "Maggie using Pump Log as new mother", "confidence": "high", "tags": [ "parenting", "app", "focused product", "willingness to pay", "customer satisfaction" ], "lesson": "Focused products that solve one problem exceptionally well build strong customer loyalty and willingness to pay", "topic_id": "topic_1", "line_start": 602, "line_end": 602 }, { "id": "e025", "explicit_text": "Slow Horses with Gary Oldman is my favorite recent show.", "inferred_identity": "Maggie's entertainment preference", "confidence": "high", "tags": [ "entertainment", "television", "personal interest" ], "lesson": "Personal interests and authentic recommendations humanize leaders", "topic_id": "topic_1", "line_start": 566, "line_end": 566 } ] }