Public Roadmap Debates: How to Stress-Test Your Strategy Before Building
Most roadmaps are created in isolation and validated by yes-men. Here's a complete system for debating your roadmap publicly—templates, rules, and lessons from 8 months of practice.
John Connor
Technology Strategist
Your roadmap is a hypothesis, not a plan. Treating it as settled fact is how you waste months building the wrong thing. This post provides a complete system for public roadmap debates: preparation templates, debate structure, rules of engagement, and post-debate documentation.
Why Most Roadmap Reviews Fail
The pattern is predictable: a small team creates a roadmap, presents it to stakeholders who nod along, then spends months building something users don't want.
The roadmap was never stress-tested. Assumptions were never challenged. Blindspots were never surfaced.
I've done this. At Sparkblox, I presented roadmaps to my team and board for months without genuine challenge. They asked questions; I had answers. The answers sounded good. The roadmap was still wrong. We built features nobody needed because I'd optimized for sounding confident, not for being right.
This post provides a complete system for public roadmap debates—a practice I've used at SuperDebate that's saved us from multiple wrong turns.
The Format: Monthly Roadmap Debate
Preparation (1 Week Before)
- Publish the proposal — Share your proposed priorities with full rationale
- Invite challengers — Explicitly recruit people to argue against it
- Set rules — Time limits, structure, what's in/out of scope
Proposal Document Template
Period: [Month/Quarter]
Proposed Priorities:
- [Priority 1]: [Brief description]
- [Priority 2]: [Brief description]
- [Priority 3]: [Brief description]
Explicitly NOT doing:
- [Thing we're not doing] — Reason why
- [Another thing] — Reason why
Key assumptions:
- [Assumption 1]
- [Assumption 2]
Success metrics:
- [Metric 1]: Target [X]
- [Metric 2]: Target [Y]
Biggest risk: [What could make this wrong]
Debate Structure (60 minutes)
| Segment | Time | Who |
|---|---|---|
| Proposition | 10 min | Founder presents priorities |
| Clarifying questions | 5 min | Audience asks factual questions only |
| Opposition 1 | 7 min | First challenger argues against |
| Response | 3 min | Founder responds |
| Opposition 2 | 7 min | Second challenger argues against |
| Response | 3 min | Founder responds |
| Open floor | 15 min | Anyone can raise points |
| Synthesis | 10 min | Founder summarizes learnings |
Rules of Engagement
- Steel-man first: Opposition must acknowledge what's strong about the proposal before critiquing
- Specific critiques only: "I don't like it" is not allowed. Must be "I think X is wrong because Y"
- Alternatives required: If you argue against something, propose what should be done instead
- No interruptions: Time limits are enforced strictly
- Document everything: Record the debate, publish notes
The Opposition Brief Template
Give this to your challengers:
The proposal's strengths:
[Acknowledge what's good—required before critiquing]
My primary concern:
[One main argument against the proposal]
Supporting evidence:
- [Data point or example]
- [Data point or example]
Alternative proposal:
[What should be done instead]
What would change my mind:
[What evidence would make me support the original proposal]
Post-Debate Documentation
After each debate, publish:
Original proposal: [Link]
Key challenges raised:
- [Challenge 1] — Raised by [Name]
- [Challenge 2] — Raised by [Name]
Changes made based on feedback:
- [Change 1] — Because [reasoning]
- [Change 2] — Because [reasoning]
Feedback considered but not incorporated:
- [Feedback] — Why not: [reasoning]
Final roadmap: [Updated priorities]
Video recording: [Link]
Why document rejections: Explaining why you didn't take advice is as important as explaining why you did. It shows you considered it seriously and builds trust even when you disagree.
Recruiting Good Challengers
| Good Challengers | Why They're Valuable |
|---|---|
| Power users | Know your product's weaknesses intimately |
| Skeptics | People who've expressed doubts—give them a platform |
| Domain experts | See things you miss |
| Former competitor employees | See your blindspots from outside |
| Advisors with context | Can challenge substantively, not superficially |
| Avoid | Why |
|---|---|
| Yes-people | Validate without thinking |
| Trolls | Attack without substance |
| People without context | Waste time on basics |
Common Failure Modes
Failure Mode 1: Defensive Founder
If you get defensive, people stop challenging. Practice: "That's an interesting point. Let me think about it." Even if you disagree.
Failure Mode 2: Performative Debate
Going through the motions without genuine openness. Test: Did anything actually change based on the debate? If not, it was theater.
Failure Mode 3: Decision Paralysis
Using debate to avoid deciding. Set a deadline: debate happens, then decision is made, then execution begins. No endless deliberation.
Failure Mode 4: Wrong Audience
Debating with people who don't have relevant knowledge. A debate with random community members about technical architecture won't be useful.
When NOT to Debate
Public roadmap debates aren't appropriate for:
- Time-sensitive decisions: Sometimes you just need to move
- Confidential matters: M&A, fundraising, personnel
- Technical implementation details: Architecture debates belong in engineering
- Reversible decisions: Just try it and see
Do debate: Major direction changes, feature prioritization, strategy shifts, resource allocation.
Measuring Success
Track these metrics to know if your debates are working:
| Metric | Target | Why It Matters |
|---|---|---|
| Changes per debate | 20-40% result in changes | Too low = theater; too high = no conviction |
| Feature success rate | Higher than pre-debate baseline | Are debated features better? |
| Community trust scores | Stable or increasing | Do people feel heard? |
| Challenger participation | Stable or increasing | Are people willing to argue against you? |
Results After 8 Months
At SuperDebate, after 8 months of public roadmap debates:
- 2 major pivots based on challenges we hadn't considered
- 35% improvement in feature completion rate (building what people want)
- 22-point increase in community trust survey scores
- 3x increase in community contributor applications
The debates don't just improve decisions—they build trust and attract talent.
Getting Started
- Start small: Debate one decision, not your whole roadmap
- Recruit 2-3 challengers: Quality over quantity
- Set clear rules: Use the templates above
- Document everything: Publish the outcome
- Iterate: Improve the format based on what works
Your roadmap is a hypothesis about what will create value. The templates are here. The format is proven. The only barrier is willingness to be challenged.