The Power of Iterative Roadmap Planning in Tech Teams

Roadmap planning is an essential aspect of any software development team. It provides clear direction for the team, sets expectations with stakeholders, and helps ensure that resources are allocated effectively. However, roadmap planning is often conducted as a one-off exercise at the end of each quarter. This approach can lead to rigid plans that are difficult to adjust when priorities change, creating unnecessary stress for the team. Instead, roadmap planning should be an iterative process, involving engineers from the onset and continuously throughout the quarter.

One of the benefits of an iterative roadmap planning process is its inherent flexibility. As the team gains deeper understanding of the product and market, priorities may shift, and new opportunities may arise. Planning in shorter cycles allows the team to make adjustments as needed without disrupting momentum. Moreover, this iterative process helps ensure that the roadmap remains relevant, keeping the team focused on delivering value to customers.

In my experience, the most successful planning processes involve both engineers and product managers working collaboratively. Engineers, with their deep understanding of the technology, often guide the conversation towards high-leverage projects. Product managers, on the other hand, bring a clear understanding of the market and customer needs. This collaboration results in a roadmap that is both technically feasible and value-driven.

When engineers are involved in the planning process, they are more likely to feel invested in the outcome.

The involvement of engineers in the planning process often leads to greater investment in the outcome. This engagement can foster a stronger sense of ownership, a culture of accountability, and ultimately, better outcomes. Moreover, engineers can provide valuable insights during planning, identifying high-risk features, potential trade-offs, and technologies that could be leveraged, whether new or pre-existing.

Lastly, I encourage all teams to share their draft plans with leadership to solicit early feedback. This can initially seem daunting, but sharing plans early allows for productive engagement with leaders and the opportunity to draw from their wealth of experience. Leaders can provide guidance, identify potential roadblocks, and offer suggestions for improvement. This feedback helps ensure alignment of the roadmap with the overall strategy of the organization, minimizing surprises down the road.

If you’re a software engineering manager or product manager, I encourage you to embrace the iterative approach to roadmap planning. Your team, stakeholders, and customers will thank you 🙏🏻.

The learning continues in…

• Chapter 1 — How Engineering Managers can understand their team better
• Chapter 2 — The Power of Iterative Roadmap Planning in Tech Teams

If you have any thoughts or experiences to add, let me know! Respond to this post or let me know on LinkedIn. I’m happy to talk about anything software engineering related.