How I Stopped Dreading Executive Roadmap Reviews
The simple technique that turned my biggest PM nightmare into a strategic advantage
It was 9:47 AM, thirteen minutes into our quarterly roadmap review, when the CEO dropped the bomb:
"I was golfing with the CEO of [major competitor] last weekend. They just launched an AI assistant feature. Why isn't that on our roadmap? We need to be leaders, not followers."
My carefully crafted roadmap—based on three months of user research—suddenly felt like tissue paper.
Sound familiar?
When months of work get sidelined by a weekend golf anecdote… you need a better way to bring your users into the room.
The Old Way: Death by Defense
Here's how these conversations used to go:
CEO: "We need an AI assistant like [competitor]"
Me: "Well, our Q3 user survey showed that AI features ranked 7th in priority..."
CEO: "That survey is three months old. The market is moving fast."
Me: "Our user interviews indicated that performance is the bigger issue..."
CEO: "Maybe we asked the wrong questions."
Me: (internally screaming)
The problem? I was playing defense with stale ammunition. Even solid research feels weak when it's delivered as "remember that study from last quarter?"
The Turning Point
Everything changed when I started bringing user voices directly into the room.
Instead of defending, I now facilitate:
CEO: "We need an AI assistant like [competitor]"
Me: "Interesting. Let me ask our power users about that right now."
(Opens Rooost on laptop)
Me: "Hey Sarah (our enterprise persona), what would you think about an AI assistant feature in our product?"
Rooost Persona: "An AI assistant? I guess it could be cool, but honestly, I can't even get your search function to find the right documents. Last week I spent 20 minutes looking for a file I KNEW was there. Fix the basics before adding AI bells and whistles."
Me: (to CEO) "What do you think about Sarah's perspective?"
CEO: "...I didn't realize search was that broken."
Game. Changed.
The Strategy: From Defense to Discovery
Step 1: Redirect to Users
Instead of: "Our research shows..." Say: "We can ask our users about that right now."
Step 2: Ask in Real-Time
Pull up your Rooost persona. Ask the specific question, and watch them answer in real time. No more digging through Slack threads or stale decks to defend a decision. The answer’s already in Rooost.
Step 3: Let Users Speak
Read the response verbatim. Include the citation to the source research file if asked. Let the user's voice carry the weight.
Step 4: Guide the Conversation
"How does this change our thinking?" shifts the dynamic from your opinion vs. theirs to collaborative problem-solving.
The magic: You're not saying no to the CEO. Your users are expressing their actual needs.
Real Scenarios To Transform Roadmap Reviews
The Mobile App Pressure
Situation: Board member insists we need a mobile app because "everyone has one"
Old way: Pull up mobile usage stats, argue about development costs
When you ask Rooost:
- Ask your power user persona: "How often do you need mobile access to our product?"
- Persona: "Maybe twice a month when I'm traveling? But even then, I just wait until I'm back at my desk. What I really need is for your web app to work properly on tablets."
- Result: Built responsive tablet view instead. 10x less effort, users actually happy.
The Enterprise Feature Trap
Situation: Sales promises enterprise SSO to close a deal, demands it on roadmap
Old way: Argue about engineering resources vs. revenue potential
When you ask Rooost:
- Ask persona: "What enterprise features are must-haves for your organization?"
- Persona: "SSO is nice but not a dealbreaker. What kills me is your lack of audit logs. My compliance team is on my back every quarter about tracking who accessed what."
- Result: Prioritized audit logs → closed 3 enterprise deals in one quarter. SSO was added later, without derailing other priorities.
The Shiny Object Syndrome
Situation: CEO sees cool visualization feature at conference, wants it yesterday
Old way: Explain our different use case, get labeled as "not innovative"
When you ask Rooost:
- Ask persona: "How would interactive data visualizations help your workflow?"
- Persona: "Pretty charts? I need accurate data first. Half the time your numbers don't match my manual calculations. I'd rather have boring, correct data than beautiful, wrong data."
- Result: Fixed data accuracy issues, NPS jumped 15 points
According to Productboard, 58% of PMs say they lack confidence that their roadmap reflects real user needs.
Advanced Persona Interview Techniques I've Learned
The Comparison Question
"If you had to choose between [CEO's feature] and [your priority], which would make a bigger difference to your work?"
The Problem Behind the Feature
"What problem would [suggested feature] solve for you?" often reveals they want something completely different
The Competitive Reality Check
"I know [competitor] has [feature]. Have you tried it? What did you think?" Usually surfaces why it's not the silver bullet
Practical Tips for Your Next Review
Before the Meeting
- Update personas with latest research
- Have your Rooost dashboard pulled up and ready to go
- Prepare 2-3 power user personas for different perspectives
During the Meeting
- Stay curious, not defensive
- Let personas speak in full sentences
- Ask follow-up questions like a moderator
- Take notes on new insights that emerge
After the Meeting
- Send follow-up with quoted user insights
- Update roadmap to reflect what you learned
- Share the technique with your PM team
Pro tip: Start using this technique in smaller meetings first. Once stakeholders see the value, they'll expect user voices in every discussion.
What Changed for Me
Before: Roadmap reviews were battles. I'd prepare for hours, trying to anticipate every objection.
After: They're collaborative workshops. We discover user needs together.
The metrics:
- Roadmap approval time: 3 meetings → 1 meeting
- Random feature requests: Down 70%
- Features shipped that reached adoption targets: 4x increase
- My Sunday night anxiety: Gone
The Unexpected Benefits
- Executives started asking better questions: "What would users think?" became the default
- Cross-functional alignment improved: Everyone heard the same user voice
- My credibility skyrocketed: Not because I was right, but because I brought data
- Research investment increased: CFO approved research budget after seeing the impact
Start Tomorrow
Your next roadmap review doesn't have to be a battlefield. Try this:
- Create one solid persona with your existing research
- Practice asking it about your current roadmap
- Use it to answer just ONE executive question in your next meeting
- Watch the dynamic shift
Ready to stop guessing what users want—and show execs the proof?
Create your first persona and start getting research-backed insights in under 60 seconds.
Final thought: The best roadmap defense isn't a defense at all. It's an invitation to listen to the people who actually use your product. Once executives hear real user voices, the right priorities become obvious.
Want to practice before your next big meeting? Start with our instant persona creator and see how different the conversation becomes.