6 Crucial Conversations to Have Before Starting Your Product Roadmap
Product managers who build roadmaps from the inside out — starting with existing backlog items and prioritizing them without first establishing the strategic context that should drive prioritization — consistently produce roadmaps that are well-organized lists of things to build rather than strategic communications of why they matter.
The conversations that happen before roadmap planning begins determine the quality of the roadmap more than the planning process itself.
Conversation 1: With Executive Leadership on Strategic Objectives
The roadmap exists in service of the company’s strategic goals. Before building it, the product manager should have genuine alignment with executive leadership about what those goals are, what role the product plays in achieving them, and what specifically would constitute success for the upcoming planning period.
This conversation should surface any disconnects between the product team’s understanding of strategic priorities and leadership’s actual expectations — before those disconnects create a roadmap that satisfies the product team but surprises leadership at the review.
Conversation 2: With Engineering Leadership on Technical Reality
The most elegant product roadmap is worthless if it’s technically infeasible. The pre-roadmap conversation with engineering leadership should surface the technical constraints that will shape what’s possible, the architectural investments that might enable new capabilities, and the technical debt that’s creating development overhead.
Engineering input gathered before roadmap items are selected is far more useful than engineering pushback gathered after the roadmap is presented.
Conversation 3: With Sales on What the Market Is Asking For
Sales teams participate in hundreds of customer and prospect conversations that product managers rarely attend. The pre-roadmap conversation with sales should extract the competitive gap patterns, the most common objection themes, and the capabilities that most frequently influence buying decisions.
Conversation 4: With Customer Success on What’s Driving Retention and Churn
Customer success teams observe what’s actually working in the product post-sale. The pre-roadmap conversation with CS should surface the features that drive expansion, the capability gaps that create churn risk, and the onboarding friction that reduces activation.
Conversation 5: With Users Through Research
No proxy for user conversations — not sales intelligence, not CS data, not support tickets — fully captures what direct user contact reveals. The pre-roadmap period is when the most important user research questions should be investigated: what problems are most significant, what’s most frustrating about the current experience, what would change users’ workflows most meaningfully.
Conversation 6: With the Product Team on Discovery Insights and Backlogs
The product team’s collective knowledge — what discovery has been done, what hypotheses are being tested, what patterns are emerging from ongoing research — should be explicitly synthesized before roadmap planning begins.
Key Takeaways
The six crucial pre-roadmap conversations — with executive leadership, engineering leadership, sales, customer success, users, and the product team — collect the information that makes roadmap prioritization genuinely informed rather than internally self-referential. Each surfaces a different dimension of the full context that good product roadmap decisions require. Starting roadmap planning without these conversations is planning with significantly less information than is available.
The Conversations’ Cumulative Value
The six conversations described above have a cumulative value that exceeds their individual contributions: they collectively prevent the most common roadmap failures. The strategic context conversation prevents roadmaps that are strategically misaligned; the engineering conversation prevents technically infeasible roadmaps; the sales and CS conversations prevent roadmaps that miss the market’s most important needs; the user research conversation prevents roadmaps built on internal assumptions; the team conversation prevents redundant discovery. Having all six is insurance against all six failure modes simultaneously.
Key Takeaways
The six crucial pre-roadmap conversations — with executive leadership, engineering, sales, customer success, users, and the product team — collect the information that makes roadmap prioritization genuinely informed. Starting roadmap planning without these conversations is planning with significantly less information than is available.