Aligning Roadmaps with Team Structure: Janna Bastow’s Solution to Product Scaling Challenges

In a recent LinkedIn post, Janna Bastow discusses a pervasive, yet often overlooked, scaling problem within product organizations: having more products than dedicated product people. Bastow highlights how this imbalance can lead to significant operational inefficiencies.

According to Bastow, the issue manifests as coordination overhead, multiplied dependencies, and a diffusion of ownership when teams manage multiple product lines with separate roadmaps. This complexity, she notes, can make prioritization incredibly difficult.

“This team had multiple product lines, overlapping initiatives, and a roadmap per surface area. Coordination became overhead. Dependencies multiplied. Everything felt connected and nothing felt owned.”

The Pitfalls of Over-Structuring

Bastow observes that the initial, and often counterproductive, instinct when facing such challenges is to impose more structure. This can involve creating more roadmaps or attempting to rigidly separate product initiatives. However, she argues that this approach often exacerbates the problem, making effective prioritization even more elusive.

“The instinct was to add more structure. More roadmaps. More separation. That only made prioritization harder,” Bastow writes.

A Shift in Roadmap Philosophy

The turning point, as outlined by Bastow, lies in fundamentally rethinking how roadmaps are organized. She proposes shifting from product-centric roadmaps to team-centric ones. This means aligning a single roadmap with a single product manager, even if that manager is responsible for overseeing multiple products simultaneously.

This organizational shift, Bastow explains, brings critical benefits. It makes trade-offs immediately visible and prevents cross-cutting work from getting lost or bounced between different backlogs. Crucially, it ensures that decisions are made at the point where the most relevant context resides.

“The breakthrough was organizing roadmaps around teams, not products. One product manager. One roadmap. Even if that meant managing multiple products together. Suddenly trade offs were visible. Cross cutting work stopped bouncing between backlogs. Decisions happened where the context lived.”

Roadmaps as a Mirror of Operations

Bastow makes a strong case that roadmaps should not be viewed as a reflection of customer perception but rather as a representation of how teams actually operate. When this alignment is skewed, no amount of sophisticated tooling can compensate for the underlying structural issues.

She emphasizes that a misaligned roadmap structure, particularly one that mirrors the org chart, marketing site, or pricing page, is likely to hinder rather than help the organization’s progress.

“Roadmaps aren’t a reflection of how customers see your product. They’re a reflection of how your teams work. When that alignment is off, no amount of tooling fixes it.”

Bastow concludes by posing a critical question for organizations to consider: “How closely does your roadmap structure match how your teams actually operate?” This prompts a reflection on whether current roadmap practices are truly supporting efficient product development and scaling, or inadvertently creating bottlenecks.