A Roadmap Is a Prototype of Your Strategy: Janna Bastow on Now, Next, Later

Janna Bastow, a product manager by background, built ProdPad after seeing that product people lacked proper tools, and co-founded Mind the Product alongside it. She says the community was never a deliberate plan. A few product people simply got together because none of them knew what they were doing, and decided to learn together.

Her answer to what kept it healthy was grassroots sharing and showing up consistently: a ProductTank meetup every month and an event every year. Early on she also realised their own network was only so wide, so they recruited other people to curate content, find speakers outside the founders' circle and write for the blog. At its peak ProductTank reached nearly 300 cities, though Bastow notes Mind the Product has since been sold.

Asked about mistakes, Bastow describes conferences as one of the most expensive and least lean things a product person can attempt, because you cannot iterate mid-event. One year the caterers under-delivered and volunteers had to buy up food from local sandwich shops, followed by cash cards for attendees as an apology. When something goes wrong, she says, the cost is in the thousands rather than the hundreds.

Other disasters included a speaker pulling out after business-class flights were booked, a printing error found the day before, and the after-party venue going bust three weeks before the first-year event. What saved them was goodwill built up with the community, which offered help and forgave the compromises. On the economics, she calls it hugely risky: monetisation only pays off at larger scale, and under-selling tickets or a shock like COVID can sink an event.

Her advice for filling seats is to run a community meetup every month for years beforehand, since that effectively is your marketing. Lenny adds that event organising is a distinct personality type, and Bastow points out that it was once listed among the most stressful jobs, which is easy to believe when everything lands on you at once.

Bastow credits much of her skill to watching nearly every Mind the Product and ProductTank London speaker and noticing what audiences respond to. When she was invited to speak on the Mind the Product stage in 2017, the organisers gave her a speaker coach who rewrote her jokes, tightened the stories and worked on posture, delivery and phrasing. The coach also made her listen to recordings of herself, which she still dislikes but says is worth it.

She now begins with the story points and narrative and only then fits them into slides, rather than letting the deck dictate the story. For nerves she uses a power pose with hands on hips before going on stage, and walks out during the tech check to get used to the empty hall. During the talk she finds the people nodding along and speaks to them, ignoring anyone bored on their phone.

She recalls blanking in front of 200 people at an early ProductCamp, simply apologising and starting again, and the audience was completely fine with it. Her lesson is that audiences are rooting for you, and that visible stumbles are humanising and show others they can take the stage too. Lenny agrees that the feared worst case almost never happens.

Bastow used to build timeline roadmaps herself. As a junior product manager she copied the colourful Gantt-chart look, lined features up against due dates and assumed she was just bad at delivery when things slipped. The first version of ProdPad digitised exactly that format, with drag-and-drop ideas on a timeline.

Early customers kept asking to shift everything over by a month. Rather than just building a multi-select feature, the team asked the five whys and discovered that nobody was delivering on the timeline they showed. That prompted Bastow and her co-founder Simon to create a three-column roadmap, current, near term and future, which became Now, Next, Later.

Her objection is that a timeline puts a due date on everything by the shape of the chart, even though the further out you plan, the more you are making up. The approach draws on the cone of uncertainty. She stresses she is not against dates: you can attach one to an item when it genuinely has one, such as a regulatory deadline, the Christmas rush or the start of the school year.

Lenny asks how sales, marketing and the CEO cope without dates. Bastow suggests regular communication so people can see what is in the Now column, which is typically weeks away, plus launch-readiness meetings. Above all, she recommends splitting soft launches from hard launches: engineering ships when it is ready, and whether that is end of September or mid-October rarely matters because marketing is busy promoting what already shipped.

Once the soft launch is live, marketing can work from a functioning product, collect videos and beta-user testimonials, and spend as long as it wants planning the big launch. Meanwhile development moves on to the next thing. That avoids the typical failure of marketing building a campaign from designer mockups that have changed by release.

For dates that are truly fixed, she says you must plan well ahead, add buffer and aim for a soft launch long before the deadline. Doing that for every launch, however, either cuts quality or buries teams in estimation, which is why large teams can be outpaced by tiny ones who just build. She admits her customers are self-selected, so her sense that around 70% want Now, Next, Later is biased, but she believes the approach is becoming the expected way of working.

Asked what separates strong product teams from mediocre ones, Bastow names two things beyond the roadmap format: a real focus on discovery, including constantly asking customers questions, and psychological safety. She describes teams that can question each other and senior leaders, and that have fewer silos because people are allowed to ask.

The single practice she highlights is the retrospective, which both reflects and builds safety by asking what is working, what is not, and whether the team is allowed to change it. Teams that learn this way naturally move toward Now, Next, Later and discovery. She contrasts that with date-driven plans, which she says mostly exist because some senior person wanted to pin the team down.

Bastow thinks of culture as calcification, like limescale built up by running water. It cannot be fixed all at once, so you chip at it by finding a small pocket, such as a startup-lab-style unit with a strong leader, and letting it show the rest of the company a different way of working. It still needs buy-in from above, which is hard because executives are incentivised toward stable quarter-on-quarter growth.

She argues that large banks and health companies face startups taking the juicier parts of their business, and unless they are willing to take a dip in order to move upward they risk losing the ability to innovate. Her enterprise rollouts, including with governments, usually start with an advocate in a division, then several groups banding together, and only then a conversation with a VP of strategy or technology.

She says ProdPad is built to nudge teams into better practice: it makes timeline roadmaps and undefined backlog ideas difficult, and it asks what problem an idea solves, what the outcomes are and whether success was measured. Those prompts, she argues, help avoid the build trap. Anyone curious can try a sandbox at sandbox.prodpad.com, though a Now, Next, Later roadmap works fine on Post-it Notes.

Bastow returns to her core claim: a roadmap is not meant to be your plan but a prototype of your strategy. Just as a feature mockup is thrown away after feedback, the value is in the prototyping, so the value of a roadmap is in laying out assumptions about problems and checking them with teammates and customers. If they push back, you learn something and the roadmap becomes stronger.

To give sceptics confidence, she points out that sales is never asked to name which deal will close on which date. A sales leader asks for investment, runs a process of calls that act as experiments, and knows from past quarters that enough will succeed. Product should ask for the same leeway and be accountable for how many experiments it ran and which numbers moved, not for predicting winners, which she calls a timeline-delivery Magic 8 Ball.

On product vision, she recommends the elevator-pitch template from Geoffrey Moore's *Crossing the Chasm*, covering target customer, need, product category, reason to buy and differentiation from the alternative. Lenny notes it resembles a positioning exercise. For PMs who want to become founders, she says the PM role exposes you to the underpinnings of business and that starting is both easier and harder than it looks, so surround yourself with advisors and figure it out one day at a time.