Getting your exec team aligned behind your roadmap is hard. In our book, Aligned: Stakeholder Management for Product Leaders, Melissa Appel and I describe a number of workshop exercises to help. My favorite for complex issues or diverse opinions is called Affinity Mapping.

Successful product leaders use workshopping to develop strategy, roadmaps, and anything else where input and feedback are valuable. A workshop can set a group on a great path forward, but it can also suffer from tangential conversations, people who don’t participate, or disrespectful behavior. Encourage frank but respectful engagement by setting ground rules beforehand.

Welcome to 2025! Here’s a resolution: If you are starting this year with a product roadmap (or at least working on one), update regularly throughout the year. No matter how well you plan, conditions inevitably change. Regular roadmap updates set the expectation within your organization that you are constantly learning and adjusting accordingly.

But how often should you update your roadmap? Here are some guidelines:

Some stakeholders seem like Grinches. Nothing is good enough and you have to make a business case to play with your toys. When the Grinch comes around, try to discover their intrinsic motivations to see if you can turn a negative relationship positive.

Some Grinches may simply be very passionate about a particular issue, and may not see their behavior as “difficult,” rather as simply the best way to get results.

Roadmaps are a team sport. If you include sales, marketing, finance, and others in your roadmapping process, you’ll get a better roadmap, and better buy in. But should you include everybody?

Test stakeholder alignment on your roadmap by asking a trusted outsider’s opinion before you finalize. Bring someone in with fresh eyes who may spot holes or problems the group missed. Do this with the whole group present and it may prompt deeper discussion of the thorniest issues as they hear their own private doubts expressed by someone they respect.

When decisions are made slowly (or not at all), when they seem to change from week to week, it’s often because it’s simply unclear who makes these decisions and how. The DACI (Driver, Approver, Contributors, Informed) framework can help by designating clear decision roles..

Roadmap alignment naturally decays. Stakeholders forget what they agreed to and even the overall goals of your team. To avoid this, frequent communication is key.

A good roadmap is a statement of strategy that helps stakeholders understand the destination and the obstacles along the way. It provides guidance for navigating those hurdles without prescribing an exact route. Yet, like a GPS, it recalculates as needed rather than a fixed set of turn-by-turn directions.

As product people, we often find ourselves trying to handle difficult stakeholders. I once had a colleague, a brilliant software architect, who objected (loudly) to any new idea. She disrupted several planning sessions, so I finally invited her to lunch. I said open debate between the two of us was confusing to the team, and we should meet one-on-one before team meetings.