Rethinking product roadmaps: now, next, later and why timelines fail

Executive overview

Timeline-based roadmaps create a false promise: assigning due dates to everything forces teams to deliver on guesses, not plans. The further out you plan, the more you're making it up — yet the Gantt format treats all dates as equally certain.

The now/next/later framework strips the timeline axis and replaces it with three buckets of decreasing certainty. Dates can still be added where they genuinely exist; the difference is that you're not inventing them for everything else.

A roadmap is a prototype for your strategy — its value lies in the process of sharing and checking assumptions, not in the document itself.

Why timeline roadmaps break

• A timeline format forces every item to carry a due date or duration — even when no real date exists
• Teams consistently miss timeline roadmap dates; this is universal, not a personal delivery failure
• The further out you plan, the less accurate dates become — but the format hides this
• Pressure to give exact delivery dates is unique to product; sales, for example, commits to pipeline outcomes, not individual deal dates

The now/next/later framework

• Three columns replace the time axis: what you're doing now, what's coming next, what's planned for later
• Specificity decreases across columns — granular commitments only where certainty exists
• Dates can still be attached to individual items when a hard deadline genuinely applies (e.g. regulatory deadlines, seasonal cutoffs)
• Items in the now column signal weeks away, not months — giving sales and marketing a working signal without false precision
• Start with post-it notes on a wall: lay out problems in order, share with stakeholders, check assumptions

Separating soft launch from hard launch

• Developers ship when the feature is ready (soft launch); marketing plans and executes their launch on their own timeline (hard launch)
• Marketing gets a working product to create videos, testimonials, and accurate copy — not designer mockups
• Eliminates the stress of synchronising two completely different project types
• Development moves on to the next thing during the hard launch period

What separates great product teams

• Consistent focus on discovery: regularly talking to customers and iterating on what's learned
• Psychological safety: team members can question direction, surface problems, and challenge decisions without fear
• Regular retrospectives: the practice is a leading indicator of safety and continuous improvement
• High-functioning teams naturally adopt flexible planning and discovery — they're not forced into timeline commitments by top-down pressure

Changing culture at larger companies

• Culture calcifies over time; it cannot be changed wholesale — chip away at it incrementally
• Find a small pocket with a strong leader and let them run as a startup lab
• Winning teams in that pocket teach adjacent teams; change spreads from there
• Buy-in from above is necessary but difficult — large company incentives (stability, quarter-on-quarter growth) are often misaligned with the behaviour needed to innovate
• Startups will erode the most attractive parts of a large business if it cannot adapt

Building product vision

• Use the Geoffrey Moore elevator pitch template: target customer → need/opportunity → product name → category → reason to buy → differentiation versus alternative
• The same template used for product positioning can anchor a product vision statement
• It answers the questions a vision needs to answer without becoming abstract

Public speaking and conference running

• Start with story points and narrative, then build slides around them — not the reverse
• Record yourself and play it back; uncomfortable but effective for refinement
• Power pose before going on stage; placebo or not, it works if it works for you
• Walk the empty stage during tech check — familiarity reduces anxiety on the day
• Find nodding audience members and deliver to them; no one notices and it steadies delivery
• Audiences root for speakers to succeed — blanking on stage and restarting is recoverable and humanising
• Conferences are a high-risk, thin-margin business; failures compound in thousands of dollars, not hundreds

PM to founder

• Product management builds most of the skills needed for founding: cross-functional exposure, stakeholder management, understanding how a business runs
• Being close to leadership before founding helps set realistic expectations
• Surround yourself with advisors mapped to problem types — no founder needs to know everything upfront
• Do not wait until you feel ready; people less capable have figured it out