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Leveraging Roadmap Planning for Engagement and Alignment


31 March, 2021

Aaron Cripps
Aaron Cripps

VP, Product at Forge Global

Aaron Cripps, VP of Product at Forge Global, explains how to facilitate alignment on a dynamic roadmap across a broad portfolio by balancing accountability to plans while maintaining agility.


Whether your organization requires a long-term roadmap plan or simply clarity on the next most important step, achieving cross-functional alignment and finding a process which fits your culture can be challenging.

How might a product leader drive productive cross-functional engagement leading toward a ratified plan which is leveraged for accountability and learning?

Actions taken

When I join planning activities, I first explore how it has been done in the past. I ask: who is involved? how is the strategy published and communicated? and how does the published plan relate to the day-to-day reality of the work that gets done?

Identifying the individuals who should be engaged but haven't (whether as a contributor or simply informed) can help fill in gaps. Early conversations with these stakeholders surfaces needs and concerns which otherwise appear very late in planning--minimizing frustrating surprises and potential re-work.

At Forge, we have evolved our planning to a rolling four-quarter roadmap. We also have a process for capturing new insights and changing the current quarter plan quickly and with organizational alignment. At the end of each quarter, we perform a retrospective and revise the upcoming quarter’s strategy. In this process, we generally find that about 20% of the imagined plan changes, which for us feels appropriate--much more change would indicate we aren’t dialed in well enough, and too little implies we aren’t responsive to emergent learning and needs.

To ensure engagement, I have three expressions of the roadmap:

  • Quarterly deck. This is primarily for the senior executive team and the board, and is written at a higher level in non-technical language. It includes a retrospective on the previous quarter, a focus on the upcoming quarter, and a separate section on the remaining three quarters.
  • Current quarter kanban board. As the cross-functional teams define a strategy to address the quarter’s goals, we visualize the Epics on a kanban board. Each Monday we gather all our teams and use the board to share a brief update on what is planned, in progress, and released.
  • The backlogs. As each team decomposes their work, they link the stories to the kanban board’s Epics which provides a clear story of the road ahead and current status.

These three expressions help everyone in the organization stay involved. It has connected our daily work with long-term goals and helps facilitate conversations about if we are working on the right things at the right time. It also gives me a very easy way to visualize status across many teams and many active initiatives.

If you are interested in how we structure our roadmap, please see my other Story, “Creating Space on your Roadmap for Innovation and Improvements”.

Lessons learned

  • Just like in product design and development, an iterative mindset yields the best results, so keep learning through small experiments.

  • Be curious and interact with your organization early, and as broadly as possible. Early on, you will likely have to absorb some of the latent frustration from individuals who should have been previously engaged, but after a few cycles you will have significantly better alignment and a plan better anchored in reality.

  • Find an expression which is authentic to your organization, while iterating the process toward a healthy space based on best practices. Aim for near-term agility and the ability to publish ideas for the future, and a process for iteratively evaluating both.

  • In terms of artifacts, tune them to your audience, and invest some time to create a process for keeping artifacts in sync with as little work as possible. For example, since your roadmap deck will likely be reviewed only once a quarter by the senior executive team and the board, revise it at the quarter boundary. Active work tracking should exist in the places most natural for the cross-functional teams to reflect changes to plan based on their learning. Check in on progress to plan along the way and fully sync the two as you go into your review and planning cycle a month before the quarter ends.

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