Strategic Product Planning: Part 2

Welcome and Introductions

Kenny Kranseler | 00:00–03:00
Welcome everyone! Thanks for joining us for “Outcome-Based Roadmaps: Ditch the Dates, Deliver the Value.” I’m Kenny Kranseler, Principal Consultant and Trainer at Productside, coming to you from Seattle. I’ll be moderating today’s session, joined by my colleague and co-presenter, Ryan Cantwell.

Ryan Cantwell | 03:01–04:30
Thanks, Kenny! Hi everyone, I’m Ryan Cantwell, Principal Consultant and Trainer at Productside. I’m based in Pittsburgh, Pennsylvania, and I’m excited to dive into this topic—one that hits close to home for every product manager. Today we’re going to talk about how to move away from date-driven roadmaps and toward outcome-based roadmaps that actually drive results.

About Productside

Kenny Kranseler | 04:31–06:00
At Productside, we help teams shift from output-based to outcome-based thinking. Whether through consulting, training, or coaching, our goal is to empower organizations to deliver measurable impact. We partner with teams globally to develop the right habits, skills, and culture to succeed in modern product management.

Poll #1 – Your Roadmap Reality

Kenny Kranseler | 06:01–07:30
Let’s start with a quick poll. How often do you find yourself updating your roadmap due to changing priorities or stakeholder requests?

Ryan Cantwell | 07:31–08:30
Wow, looks like most of you said “constantly.” That’s the pain of date-driven roadmaps. They often become tactical checklists rather than strategic tools. Let’s unpack how we can change that.

Why Traditional Roadmaps Fail

Ryan Cantwell | 08:31–12:30
Traditional roadmaps are built around delivery dates and features, not outcomes. They’re driven by “when” rather than “why.” The problem is, when dates shift—and they always do—it erodes trust. Teams scramble, stakeholders get frustrated, and PMs spend more time managing optics than delivering value. Outcome-based roadmaps fix this by connecting what you plan to do with the value it delivers.

Kenny Kranseler | 12:31–13:30
Exactly. A roadmap shouldn’t be a release plan—it should tell a story about the change you’re driving. Dates belong in project management tools; outcomes belong on the roadmap.

Defining Outcome-Based Roadmaps

Ryan Cantwell | 13:31–18:00
An outcome-based roadmap aligns product objectives with business goals. It’s less about “what” and “when” and more about “why” and “impact.” For example, instead of saying “launch new dashboard in Q2,” you might say “improve customer retention by 10% by Q2.” The feature is just one possible way to get there.

Kenny Kranseler | 18:01–19:30
Right. This shift changes conversations with stakeholders. It moves you from “when will it ship?” to “how will this deliver value?” It’s empowering for PMs and creates alignment across the organization.

How to Build an Outcome-Based Roadmap

Ryan Cantwell | 19:31–25:00
Here’s a simple three-step process:
1️⃣ **Define business outcomes.** What organizational goals are you contributing to?
2️⃣ **Connect product outcomes.** Translate those goals into measurable product results.
3️⃣ **Prioritize initiatives.** Identify the themes and bets most likely to achieve those outcomes.

When you do this, you create a roadmap that tells a strategic story instead of a list of deliverables.

Poll #2 – What’s Your Biggest Roadmap Challenge?

Kenny Kranseler | 25:01–26:30
Let’s do another quick poll. What’s your biggest challenge with roadmaps—constant changes, misaligned stakeholders, or unclear outcomes?

Ryan Cantwell | 26:31–27:30
Looks like most people chose “unclear outcomes,” which makes sense. You can’t have alignment if you don’t know what success looks like.

Communicating with Stakeholders

Ryan Cantwell | 27:31–32:30
Communicating outcomes to stakeholders is critical. Use visuals—like swimlanes or outcome themes—so leadership can see the “why” behind the “what.” Regularly review progress in terms of outcomes, not outputs. This builds trust even when timelines shift because you’re focused on delivering value, not hitting arbitrary dates.

Kenny Kranseler | 32:31–33:30
And don’t forget to educate your stakeholders. They may be used to date-driven roadmaps. Frame this shift as a maturity move—it’s about improving predictability and impact, not reducing transparency.

Common Mistakes When Moving to Outcome-Based Roadmaps

Ryan Cantwell | 33:31–37:00
1️⃣ Focusing on metrics without meaning—measure what matters.
2️⃣ Treating outcomes as slogans instead of testable results.
3️⃣ Overloading the roadmap with too many objectives.
4️⃣ Forgetting to tie outcomes to business strategy.

Start small, iterate, and refine as your team gets more comfortable with the approach.

Poll #3 – How Ready Is Your Team to Go Outcome-Based?

Kenny Kranseler | 37:01–38:00
Let’s check—how ready are your teams to move from output to outcome-based roadmaps?

Ryan Cantwell | 38:01–39:30
Half of you said “somewhat ready,” which is great. It’s a journey. The key is to start by framing one initiative around outcomes and show success—that’s how you build momentum.

Q&A and Closing Remarks

Kenny Kranseler | 39:31–End
Thank you, everyone! Fantastic questions today. If you take one thing away, let it be this: dates are guesses—outcomes are goals. Focus on the results you want, and the rest will follow.

Ryan Cantwell | 40:01–End
Thanks for joining! The on-demand recording and slides will be available shortly. Don’t miss our next webinar, “Mastering Prioritization in Product Planning.” Until then, keep your eyes on the outcomes, not the dates!