This Is How Our Product Team Created a 90-Day Rolling Roadmap
December 7, 2017

This Is How Our Product Team Created a 90-Day Rolling Roadmap

I was looking for some inspiration. This was back in October 2016 and we were in planning mode. Our product teams at WhiteHat Security had spent most of the year struggling to stay true to one annual roadmap. But as we looked back, it was clear that what we had said we would do and what we were delivering simply were not the same. Why?

It was certainly not for lack of effort. We used Aha! to set up work streams and tied that work to established metrics to track how we were doing. And it was not for lack of agility. Our engineering team was super agile, so we knew the team would adapt as needed.

And yet, what we had planned for and what we actually built had started diverging — because of changing market conditions, evolving customer demands, and previously unknown technical issues.

The juxtaposition between our fixed plan for the year and evolving conditions created frustration on all fronts.

I was looking for some inspiration. And I finally had a breakthrough when I sat in on a sales meeting. Sales sets a quota for the year and then references quarterly forecasts to guide near-term work. Those forecasts are further revised mid-quarter to reflect ongoing progress. This was exactly what I needed to reimagine our roadmap process.

While the product team still needed to plan for the year, we also needed to guide and forecast near-term work. So, in tandem with our annual planning, we decided to create a roadmap for the next 90 days — an outlook on whether defined work was going to get done.

We needed to identify the reporting in Aha! that would drive our process. We decided to use two custom roadmaps, which we share out monthly in an Aha! Notebook. One roadmap shows all products with master features (what we call “epics”) due in the last 30 days. The other roadmap shows all products with master features due in the next 90 days.

First, we created a conventional, theme-driven annual roadmap to meet company goals. Then, we lined up just enough activity to engage the product teams through the next 90 days. Our new plan was to have our four product teams (each with roughly 15 members) and the engineering managers get together at set intervals each month to do three things:

  1. Review the last 30 days of product and engineering activity

  2. Retire and promote some items from our backlog based on capacity and current priority

  3. Report the outcomes of numbers one and two to the entire company

We committed to the process. And the impact across our teams and audiences has been significant.

Product In the past, we tried creating a unified backlog for all product lines. However, with each product line in a different stage of maturity, the unified approach did not materially improve our execution. So we now run multiple product teams, each having its own backlog. We use the new joint product team meeting to resolve dependencies and repeat this process every month.

Customers We use the 90-day rolling roadmap to communicate with many of our most engaged and active customers to provide more transparency into status and decision-making. This has helped us build more trust with key customers. And the product team benefits from improved guidance on prioritizing since there are more opportunities to get feedback from those customers.

Sales and marketing The monthly planning meetings provide an opportunity for cross-functional planning. Sure, the near-term visibility helps with planning customer outreach and campaigns. But more importantly, it allows sales and marketing to influence the roadmap when required in a more direct manner — especially to prioritize tactical customer satisfaction issues that otherwise get put on the back burner.

Engineering The new 90-day rolling roadmap is much closer to their agile delivery processes. We no longer have to retroactively update based on the engineering team’s best guess of what should be worked on first. Now we are able to steer the “why” and “what” of the plan so that our engineering colleagues can focus on how it gets built.

Leadership We leverage the rolling roadmap during leadership meetings to measure incremental progress against the annual plan. We produce a monthly report that provides a snapshot view of the last 30 days and the next 90 days. Using this report, we are able to provide ongoing transparency around hits and misses, talk about what is coming, and quickly react to leadership requests.

Deciding to implement the 90-day rolling roadmap was easy. But it took a cohesive effort to implement continuous planning.

Here is a good example of what this has allowed us to do: One of our product teams had started thinking about a new use case and put together a solution that held a lot of potential. We were able to calibrate the roadmap for the next three months and start work on this new project. We added more resources from other product teams as people wrapped up their 90-day commitments.

The result? We delivered WhiteHat Scout, a new product, in just four months. Having launched half a dozen new products in my career, I know from experience that product delivery at this scale would usually have taken at least three quarters.

With our new roadmap process, we are now able to evolve the annual plans incrementally as the business needs change.

Of course, using a 90-day rolling roadmap to execute against your annual product plan is not an excuse to improvise or wing it. The key for us is to approach it as a planning exercise. Our teams are thriving in this structured approach to continuous planning.

Hopefully, as you wrap up 2018 planning, our experience provides inspiration on how you can strengthen your strategic product plan with a reasonable execution framework.

About the author Setu Kulkarni currently leads corporate and product strategy at WhiteHat Security, the leading application security platform for digital businesses. Prior to that, Setu spent over a decade at TIBCO Software in various roles in engineering and field sales before joining the product management team. He enjoys working on strategy and is always looking to create frameworks to translate that strategy to execution.

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