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ITX Product Momentum Podcast – Episode 8: Planning & Prioritizing Roadmaps

Have you ever wondered what exactly it takes to create software products? Those who spend even a little time in this space learn quickly that there is no wizard behind the curtain.

In this episode, hosts Sean and Joe speak with Rohini Pandhi, currently on the product team at Square, about her experiences developing and implementing a product roadmap – the path that connects a customer’s problems with a solution that drives their business forward. It’s not magic, Rohini says. There is no special sauce or magic potion. It’s a combination of talented, creative, hard-working people grinding through priorities, making sure they never lose sight of the customers’ destination along the journey.

At Square, the product roadmap begins with key stakeholders laying out a 1- to 3-year strategic view – based on the company’s competitive and market landscapes – of what they want to accomplish with the product. The team narrows its focus to a series of multi-quarter objectives while closely examining its OKRs (Objectives & Key Results) as a way to provide a deeper level of clarity. After further refinement comes the actual roadmap, which includes all projects that are in flight or residing in the backlog. The product roadmap isolates line items for each active workstream and provides additional links to even more details.

Prioritization: Buckets and T-shirts

In a recent blog on Medium, Rohini explains that organizations should structure roadmaps based on their individual company cultures. While there is no “one size fits all” roadmap structure, the need to prioritize projects and their tasks applies to everyone.

Many tools exist to manage the prioritization element of roadmapping. Rohini cites Adam Nash’s “Three Buckets of Prioritization” as a model worth review. The three buckets include “customer feedback,” “metrics movers,” and “foundational work.” With her Invoices team at Square, Rohini added a fourth bucket she calls “level of effort,” and within those buckets prioritizes with greater granularity. T-shirting exercises serve well here, though she’s drilled down beyond the normal “small, medium, large” framework to include “extra small” on one end and “extra large” on the other.

“The process really helps tie the team together to make sure that we’re all held accountable for the commitments we’ve made,” Rohini says. “It’s not like some consultant just came in and told us what we’re going to do. We become very attached to the goals we set for ourselves.”

Process + Creativity = Client Success

Rohini associates process with roadmapping, and appropriately so, as the roadmap represents a series of thoughtfully developed, well-orchestrated steps in a complex path to success. However, the connotation isn’t always a positive one. To many, process suggests a restrictive approach that imposes limits on behavior and rules that must not be broken.

Process provides the necessary structure around the stakeholders’ shared goals, Rohini offers. But it’s important not to let process get in the way of creativity. This is true perhaps especially in the world of software, in which all ingredients are necessary but no one ingredient is sufficient. The key is to incorporate a degree of flexibility – in process as well as in project scope and availability of resources.

The Path to Customer Success

Perhaps a more compelling way to perceive the roadmap concept is as a best practice, one that allows for testing and experimentation. In the same way innovation remains continuous, so too must the tweaking and adjusting of best practices to drive predictable results and outcomes.

Rohini concurs: “Words matter. Language matters. So just even tweaking the framework means not only that rules are allowed to be broken, but that they should be if and when something changes.”

The combination of art and science within the roadmap process allows all stakeholders to remain motivated not only by the challenge of the work, but even more so by the powerful impact their solutions have on customers.

“I’m pretty fortunate in that my team is very passionate about our work,” Rohini says. “We all embrace a sense of customer empathy around what we do.  I love bringing team members along on customer visits, because it allows them to put a face or a story to the problem we’re solving.”

To learn more about ways in which roadmapping can enhance communication, sustain creativity, and solve customer problems, check out The Product Momentum Podcast – Episode 8: Planning & Prioritizing Roadmaps.

Rohini Pandhi is currently on the product team at Square. She has experiences building new products for startups, developing existing product lines for growth stage companies, and creating new innovation strategies for larger corporations. In her free time, Rohini also advises, invests, and advocates for tech startups, especially those with underrepresented entrepreneurs through a nonprofit she co-founded called Transparent Collective.


Rohini Pandhi, Creating focus within the chaos of roadmapping.

Adam Nash, Guide to Product Planning: Three Feature Buckets.

Sean Flaherty, A Software Product’s Future: The Backlog.

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