Simplify, Follow Up, Carry the Water: What Separates Great Product Managers

Crowley has worked in startups, scaling companies and enterprise, and says the traits that set PMs apart are the same everywhere. She looks for them when hiring, promoting, or simply noticing who stands out. She names three: simplifying, following up on results, and being willing to do the hard, unglamorous work.

On simplifying, she describes big companies with endless priorities and startups with endless fires, where even picking one thing and sticking with it is difficult. The best PMs can find the one thing and stay with it until it ships. She pushes back on treating prioritization as a one-time formula, since leaders often want to re-litigate priorities a week later, and says a PM's real job is to keep beating the drum for months while keeping people energized.

The second trait is following up on results. Many specs name a metric and even come with a SQL query or dashboard, but the strong PMs return later and say "remember that thing, here's what happened." Crowley says managers a couple of layers up will not remember to ask, and that PMs who report back unprompted are rare. The third trait is the willingness to handle support, sales, marketing, copywriting and project management, a theme she links to her time at Drift.

She treats communication, analytical ability and product intuition as the basics of the role, and strategy as only a small slice of the work. In her view, the PM with a good strategy will not outperform the one who ships more, gets more reps and creates impact. People often say "drive impact" without saying how, and for her the how is mostly these three habits.

Some people are naturally simplifiers and others complexifiers, Crowley says, but the skill can be trained. Her main trick, learned from her father, is to read what you wrote out loud. When someone hands her a doc, she often asks what they are trying to say, and 99% of the time the spoken explanation is clearer than the document. Her advice is "just say that": write what you would say in conversation, because the goal is to get things done, not to impress a teacher.

To find the most important thing to do, she recommends getting as many reps as possible and having people review your work. She cautions new PMs against assuming a boss or founder is clueless, since those people usually had the market insight that made the company worth founding. Lenny adds the book *On Writing Well* and the rule of three, and Crowley agrees that strategy bets and priorities should rarely exceed three items.

Saying no to the other nine things you could do takes gumption, she argues, and the PM role is defined by a willingness to make a bet and be accountable for it. She prefers the word "bet" to "ownership" because it captures the risk that the work may fail and you still have to jump. Concretely, she recommends the Minto principle of putting the conclusion first, capping docs at three conclusions or next steps, and often deleting the first two paragraphs you wrote.

She also relies on a small private Slack group with two former Drift colleagues where they share work and ask for help simplifying it. Feedback gets harder to find as you become more senior, she says, so a trusted peer group in a non-competitive space is valuable. The tool matters less than easy access, and she notes that healthcare product leaders have a similar community.

Crowley's method for follow-up is simple: after launch, set calendar reminders for two weeks, a month and six months later to check the dashboard, then share the numbers with whoever cares. She says it is partly about visibility and partly about learning. She does not believe quietly doing great work is enough, since great managers are rare and she never wanted to leave recognition to chance.

Following up also teaches you why something worked or did not, which improves each subsequent launch. Crowley's answer to what makes a great PM is partly just that they have shipped a lot, and expertise takes years because shipping takes time. Lenny says it took him about four years to know what he was doing as a PM.

Crowley's own path took roughly five years. She started in a PM rotation at TripAdvisor, then became the only product person at a startup and realized she was not ready, and so she joined Drift to learn from strong product thinkers. Staying at Drift for almost four years let her see two or three cycles of the same product and the consequences of her decisions, which she says taught her more than a year at each of several other places.

She says there are good reasons to move jobs, but she was surprised by how much she valued staying put, and it let her move faster later. When people ask how to get promoted, her answer is always to create impact, and that can take time.

On carrying the water, Crowley says there are no tricks, only doing the work. If you hear yourself say "that's not my job," it probably is not, but you can either stay frustrated about it or get it done. People who simply get the work done move faster, their products succeed more often, and they avoid carrying around anger.

She adds that PMs are often the emotional center of a team, responsible for keeping people motivated and bought in, which is hard work. In practice, that might mean hopping on a sales call or implementing with a customer. Compared with engineers and designers, whose work has a defined deliverable, the PM's job is a business result, so the PM is uniquely positioned to fill in every gap.

Product has gained cachet, she notes, and people picture deciding what gets built. But the decision rights come with responsibility and plenty of tedious work such as project management and QA. She says none of it is above a PM, and PMs should know how the product works, be able to sell it and be able to find users.

For people trying to break in, she consulted her Slack group because it has been a long time since she did it. She sees two common paths: moving laterally within a company or joining a startup. She once hired an MBA graduate with no product experience and spent four months in person onboarding her. The hire succeeded partly because the candidate persistently emailed and made the case, and both Crowley and Lenny stress that once you have a PM title, getting the next job gets much easier.

Crowley says people, especially underrepresented people in tech approaching leadership, are often told they need to be more strategic without being told what that means. She worked out her own approach after an engineer pressed her to explain why the team was doing what it was doing. She began with a plain Google doc of bullets: the mission and goals, then a big landscape section covering the business, products, point of view on the market, competitors, a SWOT analysis and key risks.

Next comes an honest account of the current state, including what works and does not, customer feedback, support tickets and technical hurdles like tech debt. Writing all of this down tends to make the challenge visible, she says. She then adds the opportunity (where to play and why you can win), the challenges and what must be true for it to work, a proposed solution, ideally three bullets, and a plan covering sequencing, team shape and cost.

The doc is shared with everyone so that the logic chain from mission to team priority is visible, which moves disagreement from "I don't disagree with you" to "I disagree with this point." It can run 20 pages with a summary at the top, and she notes it is not for every feature, only for bigger questions like annual planning or a pivot. She writes it primarily as her own homework to be confident in her bet, and engineering and design counterparts usually engage deeply with it.

She says one effect is that comparing the strategy with the roadmap often shows the roadmap is bloated, with 90% of resources committed to things that do not track against the strategy. A PM may not have the authority to scrap the roadmap, but the exercise lets them question whether current work is still the most important. Lenny compares this to the Amazon narrative approach, where writing exposes a bad idea before anyone gives feedback.

Crowley calls the spec or one-pager the PM's artifact, since designers produce designs and engineers write code. Done well, it lets the PM start with why. She says the first section on background and context is the most important one: what the problem is, why it matters and why it matters now.

The doc then becomes a home base for decisions, with a running list of what the team decided on which day, what it chose not to do and links to research. She says templates need not be complicated, and the key is to bring the draft to the team early. Her first reader is usually her engineering counterpart, whom she asks to shred it, and she says PMs can't be precious about their work.

Lenny finds the "why now" question underused, since some opportunities are perishable, and connects it to Linear founder Karri's idea of main quests and side quests. Crowley agrees that staying disciplined is hard in a big company, and that answering "why now" matters because someone will ask anyway. Lenny adds that why-now matters in startup investing but, in his research, less than people expect for startup success.

Crowley says her standard interview question is "what's the worst product you've ever shipped?", because she thinks nobody is a good PM without having shipped something bad. Her own example was a rewrite of a core product that an engineer estimated at six months and that took two and a half years. The team skipped discovery, did not write a one-pager, and was arrogant, and it never changed the business's trajectory. Her advice is blunt: if anyone proposes a rewrite, don't do it.

Her contrarian view on product management is that people who are excited about being data-driven often show a red flag in their product thinking. Executives who say they make all decisions with dashboards often overweight quantitative data, skip direct user research and lack judgment. She does not say to ignore data, but a dashboard cannot tell you why, and talking to ten users usually produces better insights.

She recalls a TripAdvisor VP telling a team to stop justifying a project with numbers when it was obviously better and just do it. On product content, she argues that good content must be sanitized into frameworks, which can lead readers to optimize for the framework rather than impact. The best PMs have many frameworks and sometimes throw them all out; she recommends treating content as a toolkit rather than a single way, and as a leader, knowing why you are not following the rules.

Crowley calls creating content, such as her podcast, blog posts and tweets, the best thing she has done for her career. It brought networking and access, a personal brand that helps her stay employable, and a recruiting benefit because candidates reach out already knowing how she works. Her favorite benefit, though, is learning: to write about work you have to think through what you did, summarize it and process it, which made her a better product person faster.

On avoiding cringe, she says your first 10 or 20 posts will be bad and you simply have to get past that. She also says you must be authentic, noting her show worked because the questions were ones she was working on in her real PM job. Lenny adds that you cannot fake experience, and that he likes the framing of seeking to be of value rather than successful.

She argues that the things that seem easy to you may be most interesting to others, and she recalls a simple tip about drafting slides on paper that saved a colleague 75% of their time. Lenny agrees that anything you consistently find useful is a good place to start. Her closing hope is that listeners see product work as messier than it looks, that you can fail a lot and still succeed, and that you should have fun.

In the lightning round she recommends *Presentation Secrets of Steve Jobs*, *Thinking in Bets* by Annie Duke and *Scaling People* by Claire Hughes Johnson. She also names Slow Horses as a recent show and Pump Log as a focused app she loves. Her motto is that if something is worth doing, it is worth doing well, and she says Olympic speed skating taught her to find joy in years of grinding toward one shot.