Strategic Planning for PMs: Part 1

Welcome and Introductions

Kenny Kranseler | 00:00–04:30
Hello everyone, and welcome to today’s webinar, “Strategic Planning for PMs: Part 1—Good Strategy / Bad Strategy.” I’m Kenny Kranseler from Productside, and I’m thrilled to kick off this new three-part series designed to help product managers sharpen their strategic planning skills.

We’ll get started in just a moment as people join. While we do, drop in the chat where you’re joining from—it’s always fun to see our global audience. I see California, Toronto, Austin, London—fantastic!

Today’s session will run about an hour, and yes, it’s being recorded. You’ll get the replay and slides afterward. We’ll also leave time for Q&A at the end, so use the Q&A tab as we go.

Joining me today is Tom Evans, Principal Consultant and Trainer at Productside. He’s been helping product leaders define and implement strong strategies across organizations big and small. Tom, welcome—glad to have you here.

Tom Evans | 04:30–05:05
Thanks, Kenny. It’s great to be here and great to see so many of you interested in getting strategy right. It’s one of those topics that sounds simple but is so often misunderstood. I’m excited to dig in.

About Productside and Community Resources

Kenny Kranseler | 05:05–09:20
For those new to Productside, we’re an outcome-driven product partner. We help organizations shift from feature delivery to delivering measurable business outcomes. Whether you’re a product leader or an individual contributor, our mission is to help you make your product teams more strategic, aligned, and empowered.

Be sure to scan the QR codes on the slide—one links to our Productside Pulse newsletter, where you’ll get weekly “product caffeine” insights, and the other connects you with our LinkedIn community. It’s a great way to share ideas, templates, and upcoming sessions like this one.

Setting Up the Strategic Planning Series

Tom Evans | 09:20–11:10
This is Part 1 of a three-part series. In this first session, we’ll talk about what good strategy looks like and, more importantly, what bad strategy looks like—because sometimes that’s easier to recognize.

Part 2 will cover how to connect product outcomes to business outcomes. And Part 3 will focus on communicating strategy effectively to stakeholders. Our goal is to make you a more strategic, confident, and influential product manager.

Poll #1 – What’s in Your Product Strategy?

Kenny Kranseler | 11:10–13:40
Let’s start with a quick poll: What’s in your product strategy today? Is it a list of features? Is it OKRs? Is it a high-level vision statement? Or maybe it’s something else entirely. Go ahead and choose the one that best fits.

Tom Evans | 13:40–14:15
These answers are fascinating—most of you are saying “a mix of OKRs and roadmaps.” That’s pretty typical. The challenge is that neither of those things alone constitutes a strategy. Let’s talk about why.

What Strategy Is—and Isn’t

Tom Evans | 14:15–21:00
Let’s start by clearing up a common misconception: A roadmap is not a strategy. Strategy is not a list of features or OKRs or aspirational goals. Strategy is about coherent, connected choices—what you’re going to do and what you’re not going to do to achieve a specific goal.

A bad strategy is full of buzzwords—“We’ll be innovative, customer-centric, and data-driven”—but it doesn’t actually tell you how you’ll make tradeoffs or win. A good strategy creates alignment and enables decision-making.

Defining Strategy through Choices and Tradeoffs

Tom Evans | 21:00–26:30
Good strategy is about choice. You can’t be everything to everyone. You have to decide where to play and how to win. We often borrow from the *Playing to Win* framework—five key questions:
1. What is our winning aspiration?
2. Where will we play?
3. How will we win?
4. What capabilities must be in place?
5. What management systems support that?

The coherence of those answers is what defines strategy. When they’re disconnected, your strategy breaks down.

Avoiding Strategy Theater

Tom Evans | 26:30–33:10
Many organizations fall into what I call “strategy theater”—lots of activity, but no alignment. People put on a show of strategy with glossy decks and OKRs, but underneath it’s just feature prioritization.

Strategy theater wastes time and leads to frustration. Teams build things that don’t connect to outcomes, and leadership doesn’t understand why they’re not seeing results.

Examples of Strategy Theater in Action

Kenny Kranseler | 33:10–35:30
I’ve seen this firsthand—companies with massive “strategic initiatives” that are really just rebranded backlogs. People confuse activity with progress.

Tom Evans | 35:30–38:20
Exactly. I once worked with a team that spent six months creating a “vision deck.” It looked beautiful—brand colors, animations—but nobody could articulate what choices were being made. It was all theater. Strategy should simplify, not obscure.

How to Escape Strategy Theater

Tom Evans | 38:20–42:00
To escape strategy theater, start with diagnosis. Understand your real problem and your competitive context. Don’t jump to solutions. A good strategy defines the challenges clearly before proposing how to address them.

Elements of a Good Product Strategy

Tom Evans | 42:00–48:40
A solid strategy has three key parts:
1. **Diagnosis** – Understanding your environment and problem space.
2. **Guiding Policy** – The approach or philosophy that will drive choices.
3. **Coherent Actions** – The initiatives or steps aligned with that policy.

If your actions don’t ladder up to your guiding policy, you’ve lost coherence.

Deciding What Not to Do

Tom Evans | 48:40–52:30
Saying “no” is one of the hardest parts of strategy. But it’s what gives your plan focus. A company I worked with years ago had 12 strategic priorities. Twelve! That’s not strategy—it’s a wish list. When they narrowed down to three, execution improved dramatically.

Testing and Validating Your Strategy

Tom Evans | 52:30–56:00
Once you have a draft, test it. Present it to peers, leaders, and cross-functional partners. Ask: “If this is our strategy, what would we stop doing?” If people can’t answer that, your strategy isn’t specific enough.

Poll #2 – Where to Improve Your Product Strategy

Kenny Kranseler | 56:00–58:20
Our next poll: Where do you think your strategy needs the most improvement—focus, measurement, customer understanding, or alignment?

Tom Evans | 58:20–59:10
Looks like focus is leading the way—and that doesn’t surprise me. Most PMs are trying to do too much with too few resources.

Case Stories on Strategic Focus

Tom Evans | 59:10–01:03:30
Let’s look at a few case studies. One B2B SaaS company reduced its initiatives by half and doubled NPS within six months. Another shut down two underperforming verticals to invest in one growing niche—it was painful, but transformative.

Examples of Good Strategy: Figma and Swiffer

Tom Evans | 01:03:30–01:09:30
Figma didn’t try to be Photoshop; it focused on real-time collaboration. Swiffer didn’t try to replace mops—it redefined convenience. Both examples show focus and clear differentiation grounded in customer insight.

Tools for Strategic Context and Planning

Tom Evans | 01:09:30–01:16:00
You don’t need a 100-page deck to be strategic. Tools like PESTEL analysis, competitive matrices, and positioning statements can help structure your thinking. The Product Outcome Canvas is another powerful tool for linking problems, outcomes, and value creation.

Outcome-Based Roadmaps and Go-to-Market Enablement

Tom Evans | 01:16:00–01:19:30
When you connect your roadmap to outcomes, you give context to every feature. And that context empowers marketing and sales teams—they can articulate “why now” and “why it matters” far better.

Upcoming Training and Webinars

Kenny Kranseler | 01:19:30–01:23:40
Before we wrap up, a few announcements. We’ve got in-person Productside trainings coming up in London, New York, and Austin. And don’t miss Part 2 of this series—“Connecting Product Outcomes to Business Outcomes,” hosted by Tom next month.

Q&A Session and Closing Remarks

Kenny Kranseler | 01:23:40–01:28:30
Let’s take a few questions before we close.
**Q:** How often should we revisit our strategy?
**A:** At least quarterly. Strategy is dynamic—it should adapt as your context changes.
**Q:** Who should own product strategy?
**A:** PMs are the authors, but it should be validated with cross-functional input.

Final Thank-You and Next Steps

Kenny Kranseler | 01:28:30–01:30:00
That’s all for today! Thank you for joining Part 1 of our Strategic Planning series. You’ll get the recording, slides, and templates tomorrow. We’ll see you in Part 2—Connecting Product Outcomes to Business Outcomes. Have a great day!