Why the Product Strategy Nobody Disagrees With Is the One That's Guaranteed to Fail
The questions and simple math that test whether your product strategy builds real competitive advantage or is just a stakeholder-approved way to burn cash
What’s Changing As of Now
This issue deepens the pivot blending my 30 years of engineering, design, product and leadership experience with Roger L. Martin’s “Playing to Win” strategy framework by adding Rich Mironov’s “Money Stories” approach. Product teams start by reverse-engineering, designing, and testing sound strategy choices. The big shift is that now, once we’re ready to share a strategic bet with leadership, Rich gives us the tools to finally translate it into the financial language our executive stakeholders prefer.
Most product teams do one of those things, or neither.
The danger of consensus
The moment everyone in the room says your strategy is great is when you should be most worried.
You present the deck. The VP nods, asks a softball question. Sales says they’ll have an easy time getting customers to buy. Engineering says it’s no problem to build. And marketing says it’s consistent with your brand messaging. You leave the room feeling safe.
That comfortable feeling is the first sign your product is going to fail.
Why? Because choices that make everyone happy never lead to business success. They’re usually a watered-down collection of “best practices” and “customer-centric” platitudes that describe everyone and no one at the same time.
Effective strategy requires real, hard trade-offs that limit options in ways that inevitably stress people out. And that’s a good thing. Because making choices means you understand who your real customers are, how your business makes money, and are ready to focus on building competitive advantage.
And the only way to know whether you have a real strategy, and not just a wish list, is to test its logic.
AI meeting notes startup Granola’s experience with Vanta shows what real strategy looks like.
Granola’s Enterprise Revenue Acceleration
Just as AI augmented meeting notes startup Granola was gaining traction, Enterprise deals were stalling.
Some Enterprises flat-out refused to engage until Granola achieved SOC 2 compliance. After choosing Vanta, Granola achieved certification in just over three months, turning compliance from a bottleneck into a revenue driver. Granola could not only reach new Enterprise customers, but also reconnect with previously-stalled accounts.
Roughly how much revenue growth was Granola’s SOC 2 certification worth?
There are no publicly available figures or way to know for sure, but we can test the underlying strategy logic and apply a simple formula to get a sense of how many “zeroes” Vanta’s certification made possible.
Let’s start by testing our logic with strategy’s most important question.
What Would Have to Be True?
Product teams frequently waste months arguing among themselves and with stakeholders about which features will work.
They’re focused on fighting for what they assume is true, and don’t understand why no one else understands the logic and evidence exactly the way they see them.
Roger L. Martin’s breakthrough question, “What Would Have to Be True?“ (”WWHTBT”) allows teams to break logic and evidence apart. Instead of debating what you believe, you agree on what conditions must hold for your strategy to work.
For the first time, you can separate your assumption from the data you need to prove it.
In our last newsletter, we introduced the importance of Where to Play and How to Win as an inseparable matched pair. WWHTBT is your internal logic test for that set. If a strategy can’t name the exact conditions that must hold true for that pair to be a good idea, the product team needs to go back to the drawing board to design another matched set.
Here’s Vanta’s matched Where to Play and How to Win:
Where to Play: Smaller startups looking to move upmarket and capture Enterprise revenue through trust certification
How to Win: Speed up certification from quarters and years to weeks and months, and from point-in-time to continuous trust certification
By using the “What Would Have to Be True?” lens, for Vanta’s strategy to be a good idea, it would have to be true that:
Smaller startups are indeed looking to move upmarket and capture greater revenue from Enterprise customers
These startups can effectively serve Enterprise customers once they’ve been certified
Vanta unlocks sufficient Enterprise revenue to justify the investment with a reasonable return
We’ve now designed three conditions that have to be true for Vanta’s matched set to be a solid strategy.
They aren’t beliefs or hopes, but assumptions that have to be tested to understand whether they’ll prove true or not.
Now we’ll dig into how the money side might play out.
Translating Strategy Logic Into Money Logic
Our third WWHTBT condition allows us to frame our strategy story in financial terms, crucial if we’re to have a meaningful conversation with executive stakeholders.
Granola’s Condition To Test
If Granola invests in Vanta to achieve SOC 2 compliance, roughly how much new Enterprise Annual Recurring Revenue (“ARR”) might that make possible in the next year? More importantly, can it do that with a reasonable return?
We’re not going to spend hours doing deep-dive accounting or fabricating numbers.
Following Rich Mironov’s “Money Story” concept, we pick three numbers and only use multiplication so that we can “count the digits” to see if this is a 4-, 5-, 6-, or 7-digit story.
Using Granola’s WWHTBT condition for the ROI potential linked to gaining SOC 2 compliance, we’ll use Rich’s “Boosting Volume Money Story” pattern to get our three numbers in five minutes:
Stalled Enterprise Deals Addressable Base: The approximate number of Enterprise deals that stalled or went dead specifically because Granola lacked SOC 2 compliance.
Economic Average Contract Value: The Average Contract Value (ACV) of each Enterprise contract.
Guesstimated Win-Back Range: A realistic range of how many of those dead deals the sales team can re-engage and close now that the compliance blocker is gone.
[Stalled Enterprise Deals] x [Enterprise ACV] x [Guesstimated Win-Back Rate] = [Win-Back Revenue]
Applying Example Numbers
Inside of 5-10 minutes, we can assume the following internal numbers for Granola:
Stalled Enterprise Deals Addressable Base: Roughly 40 Enterprise deals went dead in the pipeline over the last year because they required SOC 2.
Economic Average Contract Value: The average Enterprise contract value is $50,000/year. (You don’t need to be precise here; just “mid-5-digits” will do.)
Guesstimated Win-Back Range: Granola’s sales team estimates they can realistically win back 10% to 20% of those dead deals.
The Calculation: 40 lost deals x $50,000 ACV x 10% to 20% win-back rate = $200,000 to $400,000 in net-new annual revenue.
You now have the formula and rough numbers to inform your SOC 2 compliance strategy story.
But raw math alone won’t persuade executives. In the paid section, I’ll show you how Rich Mironov recommends translating these numbers into a “Money Story” product teams can use to “finish their money sentences,” turning these three numbers into a clear narrative you can share in your next high-stakes leadership meeting.
We’ll also go deeper into “What Would Have to Be True?” and walk through two additional tests, the “Opposite” and “Can’t/Won’t,” to help you understand whether you actually have a strategy and whether it creates a durable competitive advantage or just sounds good.
Product Team Roadmap Discomfort Audit
Pull up your roadmap for this quarter. Ask these three questions:
Consistency: For each feature, have you stayed consistent with a matched Where to Play and How to Win set? What is it?
Logic: For your matched set, have you made at least three WWHTBT conditions clear?
The Math: Have you taken at least one of your WWHTBT conditions and defined the 3 numbers and the rough multiplication that must be true for this feature to pay for itself?
If you can’t answer these questions, you don’t have a cohesive, logical strategy guiding your work.
You’re burning cash based on hope.
Paid Subscribers Get So Much More
Free subscribers now have a solid, working knowledge of how to ask Roger L. Martin’s most important strategy question, “What Would Have to Be True?” With the introduction of Rich Mironov’s “Money Story” formula, you can now translate your strategy logic into the kind of bottom-line business impact logic product teams need to understand.
But paid subscribers also get:
The Executive Pitch Paragraph: How Rich Mironov recommends taking our financial calculation and “finishing the money sentence” so your CEO and CFO engage on what matters most to them
The Opposite Test: How to test whether your matched Where to Play and How to Win pair is making a real strategy choice for the right customer
The Can’t/Won’t Test: How to refine your matched set to identify and build structural barriers that prevent your biggest competitors from copying you
A 15-minute exercise that produces three artifacts ready for your next leadership meeting
Three AI prompts that run in the same logic sequence as the exercise and guide you to deepen your understanding of the material
Reply and let me know what resonated most for your product team’s situation.
Working with Product Teams
I’m looking for a few Product Trio leaders (PM, UX, and Tech leads) on active product teams who want to better understand strategy and financial literacy and use them to shape their day-to-day work and entire roadmap.
You’ll walk away from our free 30-minute session with a clear picture of your team’s actual strategy, the first question you need to answer to test it, and the 5-minute financial calculation you can run to show your stakeholders you care about more than just doing product “right.”
Reply TRUE and let me know a bit about you and your team, and if you’re ready to start seeing your product team’s strategic and financial impact in a new way.
