Early in my career, roadmaps felt like a wishlist. Marketing wanted X, sales wanted Y, and weâengineeringâwere somehow supposed to make it all happen. And when we couldnât, we were labeled blockers.
It took years (and more than a few failed quarters) to realize the issue wasnât execution. It was misalignment. We were promising more than our team could realistically deliver.
Hereâs what Iâve learned about making sure roadmaps arenât just ambitiousâtheyâre achievable.
1. Start With Capacity, Not Deadlines
Before locking in a roadmap, I now ask: âWhat can this team realistically handle over the next cycle?â
Not what the business hopes for. Not what looks good on a slide.
That means looking at:
- Whoâs available (and for how long)
- Time already committed to support, bugs, or tech debt
- The velocity youâve actually observed, not idealized
Setting the roadmap after capacity is understood isnât pessimismâitâs adulting.
2. Separate Strategy From Execution
Leadership often confuses goals with commitments. Strategy says âwe want to grow revenue by 30%.â Execution says âwe need three new features to get there.â
Iâve started drawing a bright line between the two. Strategy sets direction. Execution defines what the team can actually ship.
If the roadmap doesnât fit the teamâs reality, something has to giveâeither the timeline, the features, or the resources.
3. Build in Slack Time
Every roadmap should include breathing roomâfor surprises, for iteration, for life.
If your plan assumes everyone works at 100% capacity, 100% of the time, youâve already failed. Someone will get sick. A requirement will change. Production will break.
I typically plan for 70â80% of theoretical capacity. The rest goes to the stuff we canât predict but always happens.
4. Be Transparent With Stakeholders
Iâve stopped sugarcoating whatâs feasible. When a stakeholder asks, âCan we squeeze in one more thing?â I walk them through the cost:
- What gets pushed out
- What breaks our velocity
- What causes burnouts
Instead of just saying âno,â I show why it doesnât fitâand offer choices. Sometimes, they prioritize differently. Other times, we push the timeline. Either way, theyâre part of the decision, not just recipients of it.
5. Review and Re-align Often
Roadmaps arenât static. Things shiftâpeople leave, dependencies slip, goals evolve.
I do biweekly check-ins to track:
- Are we on track?
- Whatâs blocked?
- Has capacity changed?
At work in Caseproof, we use EOS as our companyâs âoperating systemâ to help us regularly review and re-align our goals.
These arenât full replansâjust touchpoints. They let us course-correct before we end up way off base.
Roadmaps Arenât PromisesâTheyâre Plans
If you treat the roadmap like a contract, every delay feels like a failure. But if you treat it like a plan, it becomes something your team and stakeholders can adjust together.
Alignment doesnât mean you can do everything. It means everyone knows what youâre doing, why youâre doing it, and what it will cost.
When you get that right, your roadmap becomes more than a wishlist. It becomes a tool for trust.