The Secret to Building a Roadmap That Endures
So, you say you want a roadmap: A clear and actionable plan your team can rally behind. Makes sense. A roadmap brings direction, helps align the team, and keeps everyone moving toward shared goals. But here's the thing: even the most thoughtfully prioritized roadmap can crumble if it’s built on shaky ground.
There are plenty of frameworks for prioritization—from point systems to effort vs. impact matrices. Those can be useful, no doubt. But when planning sessions feel frustrating or misaligned, it's usually not because the matrix was wrong. It's because the foundation underneath the prioritization wasn't solid to begin with.
Last fall, I posted a survey asking: What would make your next planning session a success? The responses were thoughtful, passionate, and surprisingly aligned. One clear theme emerged: the strength of your roadmap is only as good as the foundation it's built on.
Here are three foundational pillars I always check before building a roadmap, along with practical to-dos that will help you fortify your baseline.
1. An engaged team
You need a team that knows enough and cares enough to contribute meaningfully. Engagement isn’t about cheerleading. It’s about curiosity, context, and a sense of ownership.
Does your team have the context they need to weigh in with confidence? Are they bought into the outcomes, not just the outputs?
Here are some practical things you can do right now to create a more engaged team:
Share a short pre-read (1–2 pages) about 48–72 hours before the session that includes the problem statement, current metrics, and the expected decision/outcome.
Assign pre-work with ownership. For example, one person owns data, one owns customer insights, one owns constraints. Make it visible in the invite.
Run a 15-30 minute pre-session check-in to surface questions. Tackle anything that is unclear, ambiguous, or preventing people from feeling ready to fully engage.
Call out “why this matters” at the top of the agenda so contributors connect to purpose, not just tasks.
2. Prioritized goals that reflect a shared vision
A roadmap without a clear "why" is just a list. When goals are fuzzy or competing, it’s tough to prioritize work in a way that feels coherent.
Are your goals clearly defined, widely understood, and connected to a broader vision? Can your team name them without checking a slide deck?
Here are some practical things you can do right now to rally your team around a shared vision:
Define a big-picture goal in one sentence and distribute it ahead of time. I like to use the “how might we…” format to define the problem we aim to solve at the highest level.
Share 3-5 business outcomes that matter. In one sentence each, define the outcomes that are important and distribute them ahead of time. Include the measurement that will show progress.
Run a goals alignment exercise (30-ish minutes) at the session start where each participant defines what they believe are the long term goals (12-18 mos out). Then share, vote, and align on the top priority.
Create a “no-go” list—what you will not pursue this cycle—to reduce competing priorities.
3. Confidence in decision-making
Teams get stuck when decision-making is unclear. Do we decide together? Is there a final decider? Who breaks the tie? When this is murky, alignment suffers.
Ask yourself: Do people know how decisions get made? Is there clarity when collaboration ends and decisions get locked in?
Here are a few things you can try to help create more clear and confident decision-making:
Prior to the session, clarify a designated decider. Share the role, assignee, and responsibility with the group up front. This person will own making the final call on all decisions when the team gets stuck.
Ensure decision making autonomy. Before the group gathers, do what you need to do to ensure they can actually make choices together. If there’s not enough autonomy, the group may just spin their wheels, and it may mean you need a higher-ranking person in the org to join you.
Timebox topics (e.g., 60 minutes per topic) and assign a facilitator to keep the clock. Aim to resolve and decide on a given topic within that timeframe. If a decision isn’t met, defer with intent (see the final bullet).
Use visible decision artifacts (e.g., a shared whiteboard, slide, or Miro space) where each decision gets captured. Even better, for specifics, include a one-line record of decision, owner, target date, and next action.
If needed, defer with intent. Explicitly record what is undecided, why, and the exact information needed to decide. Assign an owner and a deadline.
If you mix these ingredients together, you're far more likely to get a roadmap that your team can believe in. One that doesn’t just sit in a doc, but actually helps guide decisions and tradeoffs in real time.
So, before you jump into another planning session or start tweaking your prioritization model, take a step back and check your foundation.
Need a hand?
If you’re feeling stuck, overwhelmed, or unsure how to facilitate a planning session that weaves these foundational elements together thoughtfully, I can help. Whether you're leading the session or wondering why it's so hard for your team to work together effectively, my sweet spot is making planning more impactful and less stressful.
Reach out here if you'd like to chat.