What kind of decision-maker is your boss? other stakeholders? your teenager? Once you have a good sense for how they make decisions, you will be better equipped to deal with challenges that come up in the decision-making process. Some types:

Your most powerful stakeholders can be dangerous if your interests are not aligned. They can hamper your progress merely by sending resources elsewhere. Worse, if actively opposing you, they can send your product to an early grave. To gain their support, establish a link between your work and their focus. Gain alignment by showing them how your work will make their plans successful.

What is required in a great product person? I like Tony Fadell’s definition in his book Build: “A needle in a haystack!...An almost impossible combination of structured thinker and visionary leader, with incredible passion but also firm follow-through, who’s a vibrant people person but fascinated by technology, an incredible communicator who can work with engineering and think through marketing and not forget the business model, the economics, profitability, PR.” Do this describe you? What did Tony miss? See the definitions in Aligned: Stakeholder Management for Product Leaders.

A stakeholder discovery interview is about listening more than talking, so you will have productive conversations in the future. Start with high-level questions to develop context and put your stakeholder at ease. They should be open-ended, like “tell me about” or “what’s challenging about...” Plan 5 minutes for every topic, and make a careful list in advance.
Here are some sample questions:

Your organization’s structure tells you who has the real power, how information is shared, and who makes the big decisions. Studying this will help you understand who are the most critical stakeholders to build relationships with and where loyalties lie.

When running a roadmap meeting (or really, any meeting), I’ve found it useful to set up a “parking lot” list of topics that should be saved for another day. This helps keep the discussion on track by parking distractions for later.

How much participation are you allowing your stakeholder?

Three groups of workers at a manufacturing plant were asked to adopt a new process, each under different conditions. See how it turned out.

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 workshopexercises 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: