The Uncomfortable Truth About B2B Roadmaps: Implementation Challenges & Solutions
"I think most teams actually do fall into [nearsighted roadmapping] implicitly where they have a medium-term vision, some tentpoles over the next quarters and very clearly outlined what will in the next weeks/month" - Job van der Voort (CEO of Remote.com and the person who coined the terminology for nearsighted roadmaps).
I recently exchanged some messages with Job about nearsighted roadmaps, but this one stood out to me.
The thing is, I feel he is right—nearsighted planning is essential in B2B tech companies. But while many PMs fall into some kind of nearsighted pattern, I've found the biggest challenge still is to turn this implicit pattern into explicit processes. Why? because the benefits of nearsighted roadmapping are all in communication and the process, not so much the roadmap itself.
Here's a Twitter summary of what nearsighted roadmapping is: Commit to specific features short-term (4-6 weeks), focus on problems, not solutions mid-term (but commit to those, too!), and align with vision long-term. Essential for B2B tech where rigid long-term feature commitments fail, but directional clarity is crucial for customer relationships. Like navigation in fog—precision was visible, but direction was not.
So today, I'd like to share my personal journey with nearsighted planning—how I approached it, what helped me succeed, and the lessons I learned along the way.
Step 1: Align with senior executives
I got started with nearsighted roadmapping in 2019 at Unite, a large B2B procurement company in Europe. And I’ve used no other roadmapping since because I love the alignment they create.
The first and most critical hurdle in my journey was getting buy-in from those who typically want certainty the most—the executive team.
When I was at Unite, I was tasked with rolling out a completely new BI system to hundreds of employees, a six-figure project with high visibility. My boss at the time, Martin Kleinsteuber, was responsible for the entire data organization. When I proposed a nearsighted approach, I expected resistance.
Instead of leading with the methodology, I focused on benefits that would matter to him:
"Martin, I want to propose an approach that will let us move faster, adapt to what we learn, and ultimately align better with our sales efforts. It's going to feel uncomfortable because we won't be committing to specific features beyond the next six weeks, but we will commit to the problems we're solving."
His response surprised me: "You know, I've been in software long enough to know that detailed long-term plans are mostly fiction anyway. Let's try it."
This wasn't universal acceptance, though. Several other directors pushed back hard, wanting certainty on when specific features would land. My approach was twofold:
Create a "shadow roadmap" for 2-3 weeks that mapped my nearsighted approach alongside our traditional roadmap
Show how the nearsighted approach actually delivered more predictably on near-term commitments
After those initial weeks, I started to gradually shift the conversations from "When will feature X be delivered?" to "When will we address problem Y?" The shift was subtle but profound.
What helped me: Starting small and demonstrating value before attempting broader change. It's like the old saying about eating an elephant—one bite at a time.
Step 2: Establish a meaningful planning cadence
With initial executive buy-in secured, my next challenge was establishing a regular cadence of planning that gave stakeholders appropriate involvement.
A roadmap is just a document. The real magic of nearsighted planning is in the process—the regular reassessment and reprioritization that keeps you aligned with reality.
At Unite, I established two complementary rhythms:
First, quarterly planning events with stakeholders (later accelerated to every six weeks) where we would:
Review progress on solving key problems
Align on the next set of problems to tackle
Discuss how these problems are connected to longer-term vision
These sessions were focused on the "what" and "why" rather than the "how." I found that framing discussions around problems rather than features elevated the conversation and brought more thoughtful participation from business stakeholders.
As one sales leader put it: "For the first time, I feel like we're talking about what matters to customers, not just what's easy to build."
Second, we established regular demos (biweekly) where we would not only showcase progress but explicitly connect what we were showing to our broader roadmap. These weren't just technical demonstrations but strategic alignment touchpoints.
What helped me: Creating a simple template that connected each demo item to a specific problem on our roadmap (the big items, not the small features). This reinforced the connection between daily work and strategic direction, much like trail markers that help hikers understand both their immediate path and destination.
Step 3: Bring dev teams into the conversation
While executives and stakeholders presented challenges, I found that development teams often embrace nearsighted planning more readily—if approached thoughtfully.
At Unite, I instituted what I called "Roadmapping Monday" with the product and development teams. This weekly session combined zooming in and out on our plans:
Zooming out: We would briefly revisit our vision and the key problems we were solving
Mid-level view: We would review progress on our current problems and discuss any new insights
Zooming in: We would align on specific implementation details for the coming week
This regular cadence created a shared understanding of both the forest and the trees. Engineers weren't just implementing features; they were solving problems within an understood context.
One senior developer told me: "This is the first time in my career I've felt like I understand not just what I'm building, but why it matters."
What helped me: Creating visible connections between daily work and longer-term problems. We added a "Problem" field to our task tracking system that linked each task to the broader problem it was addressing. It's similar to how great chefs understand not just the ingredients they're preparing but how they contribute to the overall dish.
Step 4: Communicate with everyone
With “internal” alignment established, the next hurdle in my journey was communicating our approach to customers, prospects, and the broader organization.
This is where many nearsighted roadmapping efforts falter. The approach works internally, but teams struggle to communicate it externally without appearing evasive or uncertain.
"This is too vague. I need to know exactly what features are coming and when."
Rather than getting defensive, I acknowledged their concern and then shared a story from our recent history where we had promised a specific integration by Q3, but by the time Q3 rolled around, the third-party API had changed significantly. We delivered the integration on schedule, but it was much less valuable than originally envisioned.
"What if," I asked, "instead of promising you specific features that may or may not address your needs when they arrive, we commit to solving specific problems and keep you involved in shaping the solutions as we get closer?"
To make this work, we integrated roadmap communication into our regular demo cadence:
Each demo highlighted progress on specific problems
We explicitly connected what was being shown to our broader roadmap
We invited feedback on problem definitions, not just implementations
This approach transformed demos from technical showcases into strategic alignment sessions.
What helped me: Creating a simple FAQ document that explained our nearsighted approach and why it benefited customers (I still have a small teaser above any roadmap I create). It served as a reference for our customer-facing teams—like a translation guide for a complex concept.
The Courage to Embrace Uncertainty
The fundamental challenge in my nearsighted roadmapping journey wasn't the methodology—it was finding the courage to embrace uncertainty explicitly rather than papering over it with false precision.
In a business culture that often equates confidence with certainty, acknowledging the limits of your foresight can feel risky. Yet, in my experience, it's precisely this acknowledgment that builds genuine trust with stakeholders, customers, and everyone around you.
That's the essence of nearsighted roadmapping—not an absence of planning, but a more honest approach to it. It's like navigating in fog: you focus intently on what's visible directly ahead while maintaining awareness of your broader destination.