Your Technology Roadmap Is Already Wrong

Most technology roadmaps assume we know things we don’t actually know:

We know exactly what the business will need in 18 months. We know our current technology choices will still make sense next year. We know no new tools or platforms will emerge that change everything. We know the team we have today is the team we’ll have tomorrow.

I’ve been doing this for twenty-five years, and I can count on one hand the number of times those assumptions held up for more than six months.

The roadmaps that I’ve seen lately have teams migrating to a specific cloud platform in Q3, implementing a particular AI framework in Q4, and rolling out new analytics capabilities in Q1 of next year.

Neat, sequential, logical. Also fantasy.

What happens when that AI framework gets deprecated or when the cloud migration hits unexpected compliance requirements? What happens when the business suddenly needs those analytics capabilities yesterday because a competitor just launched something similar?

The roadmap becomes a source of stress instead of clarity. Teams start defending outdated plans instead of adapting to the current reality. “But it’s on the roadmap” becomes the reason to do something that no longer makes sense.

What Actually Works for Technology Planning

I’m not saying don’t plan. I’m saying plan differently.

The best technology leaders I work with build roadmaps around capabilities and outcomes rather than specific tools and dates. Instead of “Implement Salesforce by Q3,” they write “Enable sales team self-service for customer data by the end of the year.” Instead of “Migrate to AWS,” they plan to “Reduce infrastructure operational overhead.”

This approach gives you options when things change. If a better CRM option emerges, or if AWS pricing shifts, or if the business priorities flip, you can adapt without throwing out the whole plan.

I saw this work at a manufacturing company last year. Their original roadmap called for building a custom inventory management system. Six months in, they discovered a new vendor that did exactly what they needed, but better and cheaper. Because their roadmap focused on “real-time inventory visibility across all locations” rather than “build a custom inventory system,” they could pivot without looking like they’d failed.

The technical details matter, but they belong in shorter planning cycles. I typically recommend:

• Planning capabilities for 12-18 months
• Specific technologies for 3-6 months
• Implementation details for the current quarter only

The Communication Problem with Tech Roadmaps

Most roadmap failures aren’t really technology failures; they’re communication failures.

The roadmap serves two audiences with different needs. Business leaders want confidence that technology will support their goals. Technical teams want clarity about what to build and when. The traditional roadmap tries to satisfy both by being extremely specific about everything, which satisfies neither.

Business leaders don’t actually need to know you’re using React instead of Angular. They need to know the customer portal will be faster and more reliable. Technical teams don’t need the business strategy locked in stone. They need to understand the direction well enough to make good daily decisions.

I’ve started recommending a two-layer approach.

1. A business roadmap that focuses on capabilities and outcomes, with rough timeframes.
2. A technical roadmap that focuses on specific tools and implementations, with detailed timelines only for the current quarter.

This lets you have honest conversations about uncertainty. “We’re committed to improving customer data access this year. The specific technology choices will depend on what we learn in the next few months as we dig deeper into the integration requirements.”

How to Build Technology Roadmaps That Handle Change

The question isn’t whether your technology roadmap will change, but how well it will handle change.

Build in explicit decision points. Instead of a straight line from current state to future state, create checkpoints where you’ll reassess based on what you’ve learned. “After the pilot project in Q1, we’ll decide whether to continue with this approach or explore alternatives.”

Document your assumptions explicitly. Most roadmaps bury assumptions in the details. Pull them out and state them clearly. “This timeline assumes our current database can handle 10x the transaction volume,” or “This approach requires the marketing team to standardize their data collection process.” When assumptions prove wrong, you can adjust quickly instead of pretending everything is still on track.

Leave room for opportunities. The best technology advances often come from unexpected directions, like a new tool that solves an old problem elegantly, a vendor partnership that opens new possibilities, or a team member who brings expertise you didn’t know you needed. Rigid roadmaps have no room for good surprises.

What Good Technology Planning Actually Looks Like

A few years ago, I worked with a retail company whose “roadmap” fit on one page. It listed five technology capabilities they wanted to build that year, a rough timeframe for each, and the expected business impact. That’s it.

Their quarterly planning sessions dug into the technical details, but only for the next 90 days. They spent time each month reviewing what they had learned and adjusting plans for the following month accordingly.

It’s not as impressive as the forty-five-minute color-coded road map presentations like I’ve seen from some companies. But eighteen months later, they’ve delivered more value with fewer surprises and less stress than any team I’ve seen with a “proper” roadmap.

Your technology roadmap is already wrong. The question is whether you’re building plans that can survive being wrong, or plans that will crumble the first time reality disagrees with your assumptions.

Plan for capabilities rather than technologies. Plan for quarters rather than years. And always plan for the fact that everything will change.