What are the biggest challenges when creating a roadmap for a mature product?

The biggest challenge if you are not careful is you can fall into a trap of just making incremental enhancements and not staying focused on the outcomes you want to create for customers. Its always important a Product Manager is looking for new problems, defining outcomes, thinking how the world and technology changes will change consumer behavior and using all of that to have a vision for how their product will evolve over the next 12-24 months.

Creating a product roadmap is fraught with challenges, regardless of whether you’re working on a new/growing or a mature product. That said, when dealing with mature products, it’s especially important to consider:

• Change Management: A mature product likely has a large, established user base accustomed to how the product functions – including its supported use cases, quirks, etc. This presents a challenge when considering significant changes, like overhauling the user interface or significantly modifying key user flows. In such cases, you'll need to invest considerably more in change management: How do you ensure your users are aware of the impending changes, understand what these changes mean for them, and feel comfortable with the new experience? These considerations affect everything from the rollout pace (which will likely need to be more gradual) to having to devise a legacy strategy (for instance, with APIs and platforms, ensuring that your customers' products don’t suddenly stop functioning).

• Tech Debt Management: Generally, mature products tend to accumulate more tech debt than newer products. This should be a key consideration while developing your roadmap. For newer products, only a small percentage of your roadmap might be dedicated to technical maintenance, with the bulk of your development efforts focusing on new functionality. However, with mature products, this percentage might need to be higher.

The biggest challenge with product roadmaps for any type of product is managing competing priorities. The trade-off triumvirate of time, scope and resources is always present.

For mature products, the competing priorities usually end up being competing feature requests from important customers that pull the engineering team in different directions.

Having a clear framework for managing the different feature requests and prioritizing feature development so it doesn't compromise product quality, delivery timelines, and eng team focus and velocity is extremely important. For mature products, the most important job of the product manager / GM / leader is to have clarity themselves on the top business goals and related product priorities, and to communicate those clearly to their teams so they can have alignment on the roadmap.

It can be difficult to win investment on mature products since engineering teams are looking to build new things. Additionally a mature product is often seen as nearing end of life so engineers would rather build their skills and resumes on other opportunities. This being said, the roadmap will be constrained based on the level of investment the business is willing to make.

Ways to address this are to prioritize the features that reduce the cost of operations or entice your existing customers to either consume more or generally improve their view of your offering. They will place greater value on their relationship with you.