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If there is one artifact that causes more friction between product managers and stakeholders than any other, it is the roadmap. For decades, the industry standard has been the timeline roadmap—essentially a Gantt chart that plots features against specific dates. Yet, as almost every product manager knows, these charts are often obsolete the moment they are saved. They set teams up for failure by treating product development like an assembly line rather than a discovery process.
Janna Bastow, co-founder of Mind the Product and the inventor of the "Now-Next-Later" framework, argues that we have been looking at roadmaps entirely wrong. A roadmap should not be a perfect plan of execution; it should be a prototype for your strategy. By shifting the focus from delivery dates to problem-solving, product leaders can regain credibility, foster psychological safety, and build products that actually matter.
Key Takeaways
- The Roadmap is a Prototype: Just as you prototype a feature to test design assumptions, you should treat your roadmap as a prototype for your strategy. It is a communication tool designed to be iterated upon, not a static contract.
- Escaping the Gantt Trap: Timeline-based roadmaps assume a level of certainty that rarely exists in technology. They force teams to pad estimates and prioritize "on-time delivery" over value delivery.
- The Now-Next-Later Framework: By organizing work into three buckets of decreasing granularity, teams can provide certainty where it exists (Now) while maintaining flexibility for future discovery (Next/Later).
- Decoupling Launch Dates: Separate your "Soft Launch" (engineering completion) from your "Hard Launch" (marketing push). This allows development to remain agile while giving marketing the certainty they need.
- Psychological Safety Drives Innovation: The best product teams aren't just the ones with the best tools; they are the ones with the safety to question leadership, run retrospectives, and admit when a hypothesis fails.
Why Timeline Roadmaps Set Teams Up to Fail
The traditional roadmap often looks like a math chart: time on the x-axis and features on the y-axis. This format inherently implies that every item has a specific due date and a specific duration. Bastow argues that this format forces product managers to live in "La La Land."
The further out you plan, the less you know. When a product manager places a feature on a timeline six months in the future, they are making a guess based on current assumptions. When reality inevitably shifts—due to technical debt, market changes, or user feedback—that timeline breaks. The result is a loss of trust. Stakeholders view the product team as unable to deliver, while the product team feels trapped by arbitrary deadlines.
The Problem with Certainty
In the timeline model, success is often defined as delivering a specific feature on a specific date. This incentivizes the wrong behaviors. Teams will cut corners on quality or skip essential discovery work just to meet a deadline on a Gantt chart. As Bastow notes, this leads to bloated teams that move slowly because they spend more time estimating and negotiating dates than actually building.
Adopting the Now-Next-Later Framework
To solve the timeline dilemma, Bastow introduced the Now-Next-Later framework. This approach acknowledges the "Cone of Uncertainty"—the idea that our confidence in estimation decreases the further we look into the future.
- Now: These are items currently in development. The scope is well-understood, the designs are ready, and the team is committed. These items might have specific dates because they are immediate.
- Next: This bucket contains the near-term future. The team knows what problems they want to solve, but the specific solution or feature might still be in the discovery phase.
- Later: These are high-level problems and opportunities that align with the long-term vision. They are not fleshed-out features yet, and they certainly don't have dates.
The whole point about a roadmap is that it's not designed to be your plan. I think about it as being a prototype for your strategy. The value isn't in the roadmap; the value is in the roadmapping process.
Roadmapping as a Process, Not an Artifact
When you view the roadmap as a prototype, it changes the conversation. You present your assumptions to stakeholders: "We think we have this problem, followed by that problem. What do you think?"
If a stakeholder pushes back or offers new information, you haven't broken a promise; you have simply updated your prototype. You throw out the old assumption and replace it with a better one. This makes the roadmap a living document that invites collaboration rather than a rigid contract that invites conflict.
Managing Stakeholder Expectations and Dates
One of the most common criticisms of date-less roadmapping is the fear that executives, sales, and marketing teams won't accept it. Bastow argues that "no timeline" does not mean "no dates ever." It means no dates on everything.
The Sales Team Analogy
Product managers often feel scrutinized for not providing exact delivery dates, yet other departments operate with similar ambiguity. Bastow draws a powerful comparison to the sales department.
A VP of Sales does not walk into a board meeting and promise that "Client X will sign a contract for exactly $50,000 on October 14th." Instead, they request a budget to hire account executives who will run a process (calls, demos) that yields a predictable outcome over the quarter. They can't say who will buy, but they know someone will buy.
Product teams should demand the same leeway. You are asking for resources to run experiments (development cycles). You can't promise exactly which experiment will win on which day, but you can promise that the process will move the company's key metrics in the right direction.
Separating Soft Launches from Hard Launches
To keep marketing happy without handcuffing engineering, Bastow suggests decoupling the technical release from the market release.
- Soft Launch: The engineering team deploys the code. It is functional and stable. This happens when it is ready.
- Hard Launch: Marketing executes the campaign, press releases, and public announcements.
By waiting for the soft launch to be complete before triggering the hard launch planning, marketing gains actual certainty. They can take screenshots of a real product, get testimonials from beta users, and build a campaign around something that actually exists. This eliminates the "crunch time" stress where developers are fixing bugs hours before a press release goes live.
Building a Culture of Psychological Safety
Transitioning to a flexible roadmap requires a culture shift. It demands a move away from "command and control" management toward trust and autonomy. Bastow identifies psychological safety as the critical differentiator between mediocre and high-performing teams.
The Role of Retrospectives
A litmus test for a healthy product culture is the quality of its retrospectives. In unsafe environments, teams hide mistakes or blame external factors. In safe environments, teams openly discuss what failed.
If a team determines something isn't working, are they allowed to change it? If the answer is yes, that team has the agency required to innovate. This safety allows teams to embrace the Now-Next-Later approach because they aren't afraid of admitting that a "Later" item might turn out to be a bad idea and needs to be removed from the roadmap entirely.
Consistency in Community and Communication
Beyond roadmapping, Bastow’s work with Mind the Product highlights the importance of consistency—whether building a community or a personal brand. The success of the world’s largest product community wasn't an overnight viral hit; it was the result of showing up every month, year after year.
Public Speaking as a Product Skill
Communication is a core competency for product leaders. Whether presenting a roadmap to the board or speaking at a conference, the principles are identical. Bastow advises moving away from "slide-first" preparation.
Many people open PowerPoint and start forcing their ideas into bullet points. Instead, start with the narrative. Write the story first, then build the visuals to support it. Furthermore, the physical aspect of communication cannot be ignored. Techniques like "power posing"—standing with hands on hips before a talk—can measurably reduce anxiety and improve performance, acting as a powerful placebo to trick the brain into confidence.
Conclusion
The transition from timeline roadmaps to strategic prototyping is not just a change in documentation; it is a change in mindset. It moves a product organization from an output-focused feature factory to an outcome-focused problem solver.
By adopting frameworks like Now-Next-Later and separating market promises from engineering reality, product leaders can stop apologizing for missed deadlines and start celebrating solved problems. As Bastow puts it, the goal isn't to create a perfect artifact to hang on the wall—it is to foster the conversations that ensure you are building the right thing in the first place.
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