5 Common Roadmapping Mistakes That Hold Back Your IT Team

5 Common Roadmapping Mistakes That Hold Back Your IT Team

Too many IT teams find themselves in this situation: they work hard all year, but when they look back, it's unclear whether their efforts truly advanced the business. They made tactical improvements—but not meaningful strategic progress.

The highest-performing tech teams avoid this situation. Their day-to-day work builds toward bigger goals. They’re able to do this because they have a way of working with their business stakeholders to set meaningful priorities. I’m a big advocate of using roadmaps to enable organizations to achieve alignment and set priorities. This post outlines a few of the biggest misconceptions about roadmaps and provides a few simple tips for creating effective roadmaps at your organization.

What a Roadmap Is and Isn’t

A roadmap is a tool that helps you:

  • Prioritize the most important business and technical initiatives

  • Align on rough timelines and sequencing

  • Create focus and clarity for your team and stakeholders

A roadmap is not:

  • A backlog of every idea or task

  • A detailed project plan

  • A fixed schedule

Roadmaps are best used to align on priorities. They give teams a way to say: "Item A is more important than item B right now, so we’re focusing on A first."

Unfortunately, many IT teams fall into familiar patterns when creating and managing roadmaps:

  • They draft a roadmap at the beginning of the year

  • It lists projects they expect to complete over the next 12–18 months

  • It gets little attention until next year’s planning cycle

  • Everyone shrugs about how little the actual work matched the plan

There’s a better way. Below are five common roadmapping mistakes—and how to fix them.

1. Your Roadmap Is Out of Date

One of the most common problems: the roadmap quickly becomes stale. When it doesn’t reflect reality, it loses credibility. Stakeholders may view it as a list of broken promises instead of a source of direction.

How to fix it: Expect your roadmap to evolve. Your priorities will change—and that’s normal. With this in mind, meet with your stakeholders quarterly to review and update the roadmap. Keep these sessions concise, practical and valuable to your stakeholders. Make sure your agenda includes a recap of your team's accomplishments from the prior quarter.

2. Your Roadmap Doesn’t Speak to the Business

Many IT teams treat their roadmap as a list of technical projects. But stakeholders care about what those projects enable—business outcomes and capabilities.

How to fix it: There are different types of roadmaps. Build roadmaps that go beyond technical projects. Including:

  • Business Outcomes: measurable changes in customer behavior that are relevant to the business For example: "increase qualified sales calls by 15%"

  • Capabilities: functional competencies performed by the organization via people, process and technology. For example: "Sales Qualification Process"

  • Technology Initiatives: specific technology projects. For example: "Salesforce Opportunity Stage Implementation Project"

By creating different types of roadmaps, your organization will have a more complete picture of the work your tech team is delivering and how that work is relevant to real business goals.

3. Your Roadmap Goes Too Far Out

It’s common to see roadmaps that plan out specific initiatives 12 to 18 months in advance. But the further out you go, the fuzzier your priorities become—and pretending otherwise damages credibility. Everyone knows that the landscape changes.

How to fix it: Get specific about work products for the upcoming quarter, but keep the planning for subsequent quarters at a higher level. For subsequent quarters focus more on desired outcomes and capabilities rather than specific technology projects. Alternatively, consider using a Now / Next / Later roadmap model instead of (or in addition to) a monthly or quarterly-based roadmap. Now/Next/Later gives you a framework to express priorities without estimating specific timeframes.

4. You Don’t Include Technical Debt Remediation

If your roadmap only includes new features, you’re missing a key part of strategic planning. Technical debt—like outdated code, inefficient processes, or brittle integrations—slows teams down and increases risk.

How to fix it: Include tech debt remediation alongside feature work. Explain the business value: faster delivery, lower risk, and reduced maintenance cost. Ensure that business stakeholders have clear visibility into the tech debt remediation work and its impact.

5. You Get Stuck on the Tool

Roadmaps are communication tools. They don’t need to be complex or beautiful—they just need to clearly communicate priorities and help your team have the right conversations.

How to fix it: Use whatever tool is the easiest for you: Excel, PowerPoint, Lucidchart, Miro, Elements.cloud. I use Lucidchart and Salesforce Well-Architected Roadmap templates. The format doesn’t really matter—what matters is starting the conversation. Share the draft, get feedback, and make it a habit to revisit priorities and make decisions together.

Final Thought

A good roadmap is not a static plan—it’s a living communication tool that helps you focus, adapt, and align. Avoid these five common pitfalls, and you’ll turn your roadmap into one of the most valuable tools your IT team has.

That sounds like a winning strategy to me.