Strategic Product Planning: Part 3

Welcome and Introductions

Rina Alexin | 00:00–03:00
Hi everyone, welcome to our live session, “Mastering Prioritization in Product Planning.” I’m Rina Alexin, CEO at Productside, and I’ll be moderating today’s discussion. We’re joined by one of our leading consultants, Ryan Cantwell, who will walk us through practical ways to balance data-driven prioritization with intuition and experience.

Ryan Cantwell | 03:01–04:30
Thanks, Rina. Hi everyone! I’m Ryan Cantwell, Principal Consultant and Trainer at Productside. I’ve spent over 20 years helping teams align product strategy with outcomes that matter. Today, we’re focusing on one of the toughest challenges in product management—making prioritization decisions when everything feels important.

About Productside

Rina Alexin | 04:31–06:00
If this is your first Productside webinar, welcome! Productside is your outcome-driven partner for transforming product organizations. We focus on practical frameworks and tools that empower product teams to deliver measurable business results. You can learn more about our playbooks, templates, and courses at Productside.com.

Poll #1 – Your Biggest Prioritization Challenge

Rina Alexin | 06:01–07:00
Let’s start with a quick poll. What’s your biggest challenge when prioritizing product work? Is it stakeholder pressure, limited data, competing goals, or just too many good ideas?

Ryan Cantwell | 07:01–08:30
Looks like the top two answers are “too many priorities” and “conflicting stakeholder demands.” Not surprising—that’s where most PMs struggle. Let’s dive into how we can bring structure and clarity to those challenges.

Why Prioritization Matters

Ryan Cantwell | 08:31–12:00
Prioritization isn’t just a spreadsheet exercise—it’s how you drive focus. Every “yes” means a hundred “no’s.” Without clarity, you end up building everything and achieving nothing. Prioritization helps connect your roadmap to outcomes, not outputs. It’s about aligning product decisions with business strategy and customer value.

Rina Alexin | 12:01–13:00
Exactly. A strong prioritization process gives your team confidence. It reduces churn, prevents burnout, and keeps everyone aligned on what truly matters.

Frameworks for Prioritization

Ryan Cantwell | 13:01–18:30
There are many frameworks out there—RICE, MoSCoW, Kano, Value vs. Effort, WSJF. Each one brings structure, but no single model fits every scenario.
– **RICE** works great for scoring features when data is available.
– **MoSCoW** helps align stakeholder expectations by classifying features as must-have, should-have, could-have, or won’t-have.
– **Value vs. Effort** is excellent for quick visual comparisons.
The key is not the framework itself, but the conversation it enables.

Rina Alexin | 18:31–20:00
And those conversations reveal trade-offs. The real magic happens when teams discuss why something scores high or low. Frameworks should promote alignment, not dictate outcomes.

Balancing Data and Intuition

Ryan Cantwell | 20:01–25:00
Here’s where most PMs get stuck—balancing hard data with gut instinct. Data gives us confidence, but intuition gives us speed. The trick is to combine both: use data to inform, not replace, your judgment. Experience helps you spot patterns data can’t yet show. If something feels off, explore it—your intuition might be surfacing an insight your data hasn’t caught up with yet.

Rina Alexin | 25:01–26:30
Right, and overreliance on either can lead to poor decisions. Data without context can mislead; intuition without validation can derail. Use both as inputs for a balanced, evidence-informed decision-making process.

Stakeholder Alignment

Ryan Cantwell | 26:31–31:00
Prioritization fails most often due to misalignment, not math. Stakeholders come with their own agendas—sales wants speed, engineering wants stability, and executives want growth. As PMs, our job is to make those competing perspectives visible and facilitate trade-offs. Use frameworks like RICE or a prioritization matrix in a live workshop—it’s amazing how fast alignment happens when everyone sees the same data.

Rina Alexin | 31:01–32:30
Yes! And invite stakeholders early. If they co-create prioritization decisions, they’ll support them later—even when their pet projects get delayed.

Poll #2 – Which Framework Do You Use Most?

Rina Alexin | 32:31–33:30
Let’s take another poll. Which framework do you currently use most—RICE, MoSCoW, Kano, or Value vs. Effort?

Ryan Cantwell | 33:31–35:00
Interesting—RICE takes the lead, with MoSCoW a close second. Remember, it’s less about which framework you pick and more about creating shared understanding around priorities.

Common Pitfalls in Prioritization

Ryan Cantwell | 35:01–40:00
Here are the biggest traps I see:
1️⃣ Prioritizing based on opinions instead of outcomes.
2️⃣ Forgetting to revisit decisions when context changes.
3️⃣ Using frameworks mechanically without real discussion.
4️⃣ Letting urgency override strategy.
Effective prioritization is continuous—it evolves as you learn.

Making Prioritization a Habit

Ryan Cantwell | 40:01–45:00
Turn prioritization into a rhythm. Embed it in sprint planning, quarterly reviews, and roadmap discussions. Use tools like a product opportunity backlog to track ideas and evaluate them consistently. Transparency builds trust—publish your scoring criteria so stakeholders understand the “why” behind your choices.

Rina Alexin | 45:01–46:30
That’s so important. Prioritization shouldn’t happen behind closed doors. When everyone understands how decisions are made, they’re more likely to support them—even if they disagree.

Poll #3 – How Confident Are You in Your Prioritization Process?

Rina Alexin | 46:31–47:30
Final poll for today: How confident do you feel in your team’s prioritization process—highly confident, somewhat confident, or not confident?

Ryan Cantwell | 47:31–49:00
Looks like most people are “somewhat confident,” which is great—it means you’re aware and improving. Keep refining. Prioritization is like a muscle; it gets stronger the more you practice.

Q&A and Closing Remarks

Rina Alexin | 49:01–End
We’ll wrap up with a few audience questions. One question we received: “How do you handle prioritization when data is incomplete?” Ryan?

Ryan Cantwell | 49:30–End
Great question. In those cases, use qualitative insights, run small experiments, and learn fast. Prioritization doesn’t have to be perfect—it just has to be intentional. Thank you all for joining us! Don’t forget, the recording and slides will be available soon, and our next session, “Product Management Nightmares,” is coming later this month. Thanks again, and have a great day!