Coaching Product Managers: Five Ingredients, Honest Storytelling, and the Case for Community

Petra Wille describes herself as a coach for the people who lead product people: product directors, team leads and CPOs of smaller startups. Over the past few years she has coached about 130 people one-on-one, typically in 10 to 20 sessions each, and reached roughly another 150 through group, corporate and public sessions. Counting the ripple effects on their teams and on readers of her book, she estimates her influence at 50,000 to 60,000 people.

Lenny points out that the first-line-manager and director layer is often the most influential in a company, because those people make day-to-day decisions. Wille adds that many of her clients are not trained product people at all. They come from marketing, business, data or engineering backgrounds, so they lack both basic product practice and empathy for the struggles of the PMs they manage.

Two gaps stand out to her. Individual-contributor PMs often struggle through problems alone because their managers do not know the wider product community and cannot point them to a relevant talk, book or technique. And the role itself is far broader than a "T-shaped" profile, which is why she uses the image of an eight-legged creature that must handle business problems, user problems, discovery, delivery, data and iteration at once.

Wille's first ingredient is a solid, written definition of what a good product person looks like in your context, separating personality traits that are hard to develop from skills and know-how that can be coached. Most leads she works with carry this only as an implicit feeling. The second is knowing where each PM currently stands in their career and life, then imagining how good they could become and, above all, what the "next bigger challenge" would be for them.

She suggests blocking an hour each quarter to write down every direct report's name and their next bigger challenge. Opportunities do not always appear the next day, but once the list exists you can spot them and assign the right person. The third step is sharing that vision with the PM in an alignment conversation, since your picture and theirs may differ.

The fourth ingredient is a development plan, which she says is on the PM to carry out, but where managers help by showing the gap between the definition of good and the person's current profile and by suggesting small steps such as a book, a conference talk or a reflection on prioritization. The fifth is follow-up: a nudge at the water cooler, with each person choosing how often they want to be reminded. Lenny notes that the structure mirrors product strategy, with a problem, a direction, a vision and regular check-ins.

Asked where a new manager should begin, Wille says with the development plan. Even without a formal assessment, most PMs already know something they want to improve, or colleagues have complained about, such as storytelling or backlog ordering. Starting there takes little time, and she recommends creating a fresh plan with a new theme every quarter or every four months.

She also warns against waiting to build a company-wide competency framework. Leads often try to align with peers and HR, and the process can take ages. Her advice is to build a compass for your own team first and harmonize with others later, because giving your people orientation now beats being paralyzed by the lack of a shared one.

Lenny shares his own routine: a shared Google Doc with a few themes and concrete actions after each six-month review, plus a monthly coaching session with a color-coded status for each item. Wille agrees, saying "consistency beats intensity" applies both to PMs learning and to leads investing in their people, and that regular small check-ins beat big 360-degree reviews. Both stress that the PM should own the plan rather than receive it.

For companies without a career ladder, Wille recommends using one of the existing PM assessments, including Marty Cagan's, PM Daisy and her own PMwheel, and then heavily customizing it. A copy-paste approach fails when, for instance, your PMs are mostly technical and discovery-interview criteria matter less. Lenny adds that he compiled a public spreadsheet of skills evaluated at the largest tech companies' career ladders.

She also asks leads to reflect on personality traits, since some things are better hired for than developed. For her the key one is curiosity, which she sees in the best product people whatever the topic, and empathy is another. She can help someone build the empathy muscle, but if there is no decent level to begin with, it is nearly impossible to move them to a seasoned level.

The PMwheel splits PM work into eight buckets: understanding problems, finding solutions, planning, getting it done, listening and learning, team, personal growth and agile. Each comes with at least 15 framing questions, and she suggests a self-assessment, a manager assessment and ideally input from team members. She built it out of her own need for a compass when starting a coaching relationship, since clients are often sent to coaching and arrive unsure what to work on.

Lenny observes that the coaching recipe is straightforward and not time-consuming: work out what success looks like, where the PM is, align on it, and give them a few things to focus on. Wille says her book goes further, covering onboarding, hiring and how to explain concepts such as hypothesis-driven product development to people who have not met them. A lot of the magic, she says, is in small practical help, like teaching the Eisenhower matrix to someone who has never had a tool for prioritizing.

On content overload, Lenny suggests learning things when you need them rather than trying to read everything. Wille mentions a coach who dedicates a whole year to one methodology, such as Teresa Torres's Continuous Discovery Habits, and then compares notes with colleagues who picked a different book.

Her final tip is to keep a go-to list of coaching questions for the days you cannot prepare, such as how someone is doing and what would make them more successful. She also keeps a list of about 30 emotions, because people often struggle to describe how they feel. Lenny adds Matt Mochary's framework of rating yourself one to ten and asking how to move from a six to a seven, which Wille likes because it targets incremental improvement rather than stressing people out.

Lenny notes that leaders are constantly told to be great storytellers, yet advice rarely helps when you face a blank deck. Wille offers two tips. First, beginners underestimate the time great storytellers invest in crafting and packaging a story, and a rule of thumb for explaining the next three to four months to a company is about two weeks of work at one or two hours a day.

Second, use language that speaks to hearts and minds rather than business lingo. Words like "product discovery" can become invisible through overuse, so she suggests simpler phrasing such as saying you need to learn something about a particular thing. She cites research suggesting stories affect the brain, with hormones released depending on how a story is built, and says using sensory, human language helps, though removing three-letter abbreviations is harder than it sounds.

She also sees a cultural dimension: in her view Americans tend to be better at it than many Europeans, partly because schools encourage speaking in front of a class. Wille's practical conclusion is that storytelling is learned through practice, not overnight talent.

Both Lenny and Wille admit to being nervous speakers. Her advice is to start in front of small, friendly audiences, such as your own team, a company all-hands or a local product meetup. Her first talk was a five-minute update at an all-hands of about 90 people, and it still freaked her out. She also recommends getting feedback from both peers, who are harsher, and strangers, who are politer but can spot gaps because they lack your context.

For pre-talk nerves she names two tricks: the Superman pose and gently tapping the chest area to lift your energy, ideally done backstage. Friendly faces in the front row also help. On whether PMs must be great speakers, she says that an IC can do the job without it, but getting promoted is far harder if you cannot tell stories and rally a team behind a shared goal. A team can partly compensate, yet she would call it a career staller.

Her storytelling heroes are her former boss Jason Goldberg, who took every stage to explain what the product organization wanted to achieve, Hans Rosling for proving that data-heavy topics can make gripping talks, and the spoken-word poet Sarah Kay for showing how playful language can be.

For a new document or deck, Wille says not to stare at a blank page: draft quickly, talk the story through with others, see how it lands and tweak it. She calls story a design tool, since it is easier to change a story than a prototype. She often uses the hero's journey, deciding whether the hero should be the team, to motivate it, or the user, to show how life improves once the product ships.

She advises having the story ready in several forms: spoken, written for asynchronous teams, and illustrated with whiteboard sketches or a few emotional slides. She also wants three lengths: a 75-second elevator pitch, a six-minute version, and a long version of about 80 minutes for an all-hands, with the length of a TED talk tied to attention spans. This effort is meant for vision or strategy a few months out, not the next sprint.

On resources, Lenny recommends Steven Pressfield's *Nobody Wants to Read Your Sh*t*. Wille credits Guy Kawasaki's *Selling the Dream*, which Marty Cagan had her read, for showing her she had to work on the skill, and says Nancy Duarte's books and free material helped her most.

Wille's interest in community started from a wish to scale her coaching: if line managers do not take care of development, something else has to. Early in her career she worked in an engaging product organization where people shared what worked and what did not, and everyone improved. This year she researched communities of practice, speaking with clients and running a survey, and found that many companies never considered starting one and many people had never heard of external product communities.

She names three benefits. Retention improves because people stay where they learn and grow toward mastery. Product leads carry less of the development load. And it is cheap compared with trainings, conference tickets and external coaches. Signs of a good community, she says, are meeting interesting people, learning something new from time to time, being able to contribute, trusting others and enjoying the company, with enough activity that it is not a dead space.

Lenny and Wille note that communities can be offline too, such as local meetups, and that giving back clarifies your own thinking.

Lenny describes his paid Slack community of roughly 10,000 PMs, founders and growth leaders, with meetups, mentorship and mastermind groups, and asks for advice. Wille congratulates him and shares her community canvas: periodically revisit the community's purpose, values and definition of success, find rituals and rhythm, and think about incentives and sponsoring such as extra training budget or time for active members.

She stresses roles. A community resting on the shoulders of one to three people is not sustainable, so workload and responsibility such as moderation should be distributed. She prefers to think in circles of 10 to 15 people around different interests, linked by bridges, rather than a pyramid. Lenny says he deliberately tries not to be the center and credits a core team that runs community, curation, meetups and mentorship.

Wille also questions engagement as a success metric, suggesting signal versus noise is better, and says organizations need someone with real time for community management. She still considers that cheaper than sending everyone to trainings and conferences, with network effects as a bonus.