This feels less like a roadmap, more like a well-crafted features contract. Nothing wrong with that, but let’s not confuse it with a strategic roadmap built around outcomes.
A true roadmap charts the path from today’s messy middle to the outcomes we’re aiming for. That strategy should drive what gets built ... not the other way around.
Otherwise, we risk sliding into order-taking mode, serving requests instead of steering growth. Tactics should follow vision, not lead it.
I was expecting a comment like this. And this time, I'm going to bite.
First, I agree with the importance of a "strategic roadmap" for internal alignment. Cool.
But that's different from a customer-facing roadmap meant to be sent to enterprise customers who are trying to understand your future product plans. This is where you're conveying what you have ALREADY internally agreed on.
A CFR is essentially translating your problem themes into something tangible for the customer. It is also produced AFTER the vision, strategy, and roadmap are finalized. It doesn't drive those items.
While a CFR should still highlight strategy, it also needs a level of concreteness that customers can actually understand and connect with. These are two different documents for two different purposes.
Doodling strategic mindmaps for enterprise customers won't earn much goodwill. They want clarity about what's being built. I'm still about highlighting outcomes as shown in the example. But stakeholders have small attention spans, so it's important to clearly lay out the problems and solutions you're pursuing.
You mentioned "a true roadmap charts the path from today's messy middle to the outcomes we're aiming for." I'm with you on that - and I did say you highlight outcomes across the asset along with problem sets and context. I'm not suggesting the CFR should be stripped of that narrative.
"Tactics should follow vision" - absolutely agree. But the CFR isn't an invitation to co-create vision with customers. Far from it. The vision's already set. You're articulating the tactics you've chosen to execute that vision/strategy and win customer trust. You're getting them excited about the problems you have already decided to go after.
Sure, it might look like a features contract on the surface, but if you unpack it, it's really not.
The stuff you're building in the next 90 days? That's already in your dev pipeline, probably fleshed out in mockups or staging. You're just giving customers visibility with messaging they can understand. You'll still highlight outcomes, but unnecessarily wrapping it in strategic jargon doesn't help with CFRs. It just creates more cross-questioning.
For initiatives further out, I've maintained that you need to keep conversations focused on outcomes without committing to specifics. I've also said it's better not to share initiatives that far out anyway as market dynamics can change.
A CFR doesn't promote order-taking mode at all. In fact, it's nearly the polar opposite.
It's a document that literally shares the direction you've already chosen. This isn't a wishlist call. In fact, some customers might not like your direction and might pass on you. That's fine, as long as you're not fooling anyone with wrong priorities.
I've tried handing memos to customer success and sales about future "strategic" directions. But they didn't help as much as the CFR template I described in the article, especially with larger ACV contracts.
Sure, your experiences might be different. You're free to write an expansive article on that. I'd be happy to read that.
Just because we've escaped feature-factory hell doesn't mean talking about initiatives or features suddenly becomes evil or that every artifact that solely isn't centered around buzzwords like strategy or outcomes is a cardinal sin.
You know why I don’t pull into a Waffle House when I’m hungry? Because I’m not looking for a laminated menu full of greasy options and blind confidence. I want a meal with intention, not just a pile of outputs on a plate.
Same goes for what we hand to customers.
If I’m putting something in front of them, I’m going to lead with a strategic roadmap—a clear picture of the transformative journey we’re taking them on. Then I’ll show them the tactical release plan—what we’re building next, and why it matters in terms of moving the needle for them.
This way, we set expectations around value creation—for their goals and ours. We’re running a business here, not a food line.
As for being balanced and results-oriented, it’s just a matter of whether we want to serve a thoughtful meal ... or keep measuring success by how many Tums we hand out to cover the indigestion caused by outputs that never find their way to outcomes.
And the last thing I want to serve customers is menu of caloric intakes without first framing the dining experience and nutritional gains. Because that might fill the moment—but it won’t keep them coming back.
You know what's funny about that Waffle House analogy?
Thousands of people actually do pull into Waffle House when they're hungry. Why? Because they know exactly what they'll be served and what they'll pay for it. Waffle House may have greasy options, but there's value in creating clarity on expectations.
Honestly, I feel the restaurant analogy is a false equivalency as you can't compare a relatively rigid menu with an evolving, sophisticated piece of software, but since you brought that to this discourse, here's my next question:
What DO you do when you're hungry?
You want "a meal with intention," so how do you find that?
When you finally walk into a fine dining restaurant that meets your non-greasy lifestyle, I guess you never ask for the menu?
Perhaps, you want that menu card to relay outcomes like the explosive gastric journey you'll go on and the caloric content. But most people also want to know the cuisine, what's actually on the menu, the prices, and if items have fancy names like "Bun on the Run," they want clarity on ingredients and preparation.
And then you go on to say "first, I'll show the strategic roadmap, then I'll show them the tactical release plan."
Not sure what we're squabbling about then.
That's literally the CFR structure I'm suggesting. That's what I'm advocating you'll begin with. If you don't agree with my opening slides and feel they lack on "strategic weight", fine. PMs can go gung-ho on conveying their strategic narratives and carefully paint that "transformative journey" to their heart's content.
But let's not pretend we don't all eventually converge on sharing what's actually being built to meet those outcomes. That's what customers will spend most of their time evaluating. That's where I've focused most of this article.
Some enterprise buyers might require product strategy documents. I'm sure there's demand for it. But in my experience, that's insufficient for them to justify six-figure investments to their boards. They need concrete details.
Anyway, enough about me, Dean.
I'm now genuinely curious to see what your pristine battle-tested CFR version looks like.
Can you drop a few example links here for the community and me to peruse? I'm happy to be shown a better way by the strata who look down upon people who go to Waffle House. Because those who do never want "meals with intention".
You know it's funny about the waffle House analogy? Very few people take their spouse there for an anniversary or birthday. Why do you suppose that is?
Wanna know what else is funny? Most return customers are either late drinkers or light spenders. Great if you're into a service business model built around lowest price commodities. It means you can forgo the product managers, and simply hire taskmasters.
This feels less like a roadmap, more like a well-crafted features contract. Nothing wrong with that, but let’s not confuse it with a strategic roadmap built around outcomes.
A true roadmap charts the path from today’s messy middle to the outcomes we’re aiming for. That strategy should drive what gets built ... not the other way around.
Otherwise, we risk sliding into order-taking mode, serving requests instead of steering growth. Tactics should follow vision, not lead it.
I was expecting a comment like this. And this time, I'm going to bite.
First, I agree with the importance of a "strategic roadmap" for internal alignment. Cool.
But that's different from a customer-facing roadmap meant to be sent to enterprise customers who are trying to understand your future product plans. This is where you're conveying what you have ALREADY internally agreed on.
A CFR is essentially translating your problem themes into something tangible for the customer. It is also produced AFTER the vision, strategy, and roadmap are finalized. It doesn't drive those items.
While a CFR should still highlight strategy, it also needs a level of concreteness that customers can actually understand and connect with. These are two different documents for two different purposes.
Doodling strategic mindmaps for enterprise customers won't earn much goodwill. They want clarity about what's being built. I'm still about highlighting outcomes as shown in the example. But stakeholders have small attention spans, so it's important to clearly lay out the problems and solutions you're pursuing.
You mentioned "a true roadmap charts the path from today's messy middle to the outcomes we're aiming for." I'm with you on that - and I did say you highlight outcomes across the asset along with problem sets and context. I'm not suggesting the CFR should be stripped of that narrative.
"Tactics should follow vision" - absolutely agree. But the CFR isn't an invitation to co-create vision with customers. Far from it. The vision's already set. You're articulating the tactics you've chosen to execute that vision/strategy and win customer trust. You're getting them excited about the problems you have already decided to go after.
Sure, it might look like a features contract on the surface, but if you unpack it, it's really not.
The stuff you're building in the next 90 days? That's already in your dev pipeline, probably fleshed out in mockups or staging. You're just giving customers visibility with messaging they can understand. You'll still highlight outcomes, but unnecessarily wrapping it in strategic jargon doesn't help with CFRs. It just creates more cross-questioning.
For initiatives further out, I've maintained that you need to keep conversations focused on outcomes without committing to specifics. I've also said it's better not to share initiatives that far out anyway as market dynamics can change.
A CFR doesn't promote order-taking mode at all. In fact, it's nearly the polar opposite.
It's a document that literally shares the direction you've already chosen. This isn't a wishlist call. In fact, some customers might not like your direction and might pass on you. That's fine, as long as you're not fooling anyone with wrong priorities.
I've tried handing memos to customer success and sales about future "strategic" directions. But they didn't help as much as the CFR template I described in the article, especially with larger ACV contracts.
Sure, your experiences might be different. You're free to write an expansive article on that. I'd be happy to read that.
Just because we've escaped feature-factory hell doesn't mean talking about initiatives or features suddenly becomes evil or that every artifact that solely isn't centered around buzzwords like strategy or outcomes is a cardinal sin.
Balance matters. Results matter.
You know why I don’t pull into a Waffle House when I’m hungry? Because I’m not looking for a laminated menu full of greasy options and blind confidence. I want a meal with intention, not just a pile of outputs on a plate.
Same goes for what we hand to customers.
If I’m putting something in front of them, I’m going to lead with a strategic roadmap—a clear picture of the transformative journey we’re taking them on. Then I’ll show them the tactical release plan—what we’re building next, and why it matters in terms of moving the needle for them.
This way, we set expectations around value creation—for their goals and ours. We’re running a business here, not a food line.
As for being balanced and results-oriented, it’s just a matter of whether we want to serve a thoughtful meal ... or keep measuring success by how many Tums we hand out to cover the indigestion caused by outputs that never find their way to outcomes.
And the last thing I want to serve customers is menu of caloric intakes without first framing the dining experience and nutritional gains. Because that might fill the moment—but it won’t keep them coming back.
You know what's funny about that Waffle House analogy?
Thousands of people actually do pull into Waffle House when they're hungry. Why? Because they know exactly what they'll be served and what they'll pay for it. Waffle House may have greasy options, but there's value in creating clarity on expectations.
Honestly, I feel the restaurant analogy is a false equivalency as you can't compare a relatively rigid menu with an evolving, sophisticated piece of software, but since you brought that to this discourse, here's my next question:
What DO you do when you're hungry?
You want "a meal with intention," so how do you find that?
When you finally walk into a fine dining restaurant that meets your non-greasy lifestyle, I guess you never ask for the menu?
Perhaps, you want that menu card to relay outcomes like the explosive gastric journey you'll go on and the caloric content. But most people also want to know the cuisine, what's actually on the menu, the prices, and if items have fancy names like "Bun on the Run," they want clarity on ingredients and preparation.
And then you go on to say "first, I'll show the strategic roadmap, then I'll show them the tactical release plan."
Not sure what we're squabbling about then.
That's literally the CFR structure I'm suggesting. That's what I'm advocating you'll begin with. If you don't agree with my opening slides and feel they lack on "strategic weight", fine. PMs can go gung-ho on conveying their strategic narratives and carefully paint that "transformative journey" to their heart's content.
But let's not pretend we don't all eventually converge on sharing what's actually being built to meet those outcomes. That's what customers will spend most of their time evaluating. That's where I've focused most of this article.
Some enterprise buyers might require product strategy documents. I'm sure there's demand for it. But in my experience, that's insufficient for them to justify six-figure investments to their boards. They need concrete details.
Anyway, enough about me, Dean.
I'm now genuinely curious to see what your pristine battle-tested CFR version looks like.
Can you drop a few example links here for the community and me to peruse? I'm happy to be shown a better way by the strata who look down upon people who go to Waffle House. Because those who do never want "meals with intention".
You know it's funny about the waffle House analogy? Very few people take their spouse there for an anniversary or birthday. Why do you suppose that is?
Wanna know what else is funny? Most return customers are either late drinkers or light spenders. Great if you're into a service business model built around lowest price commodities. It means you can forgo the product managers, and simply hire taskmasters.