Work
The whiteboard was covered in sticky notes, arrows, and enough buzzwords to kill a small horse. We had a vision statement printed in a fancy font on the wall. We had product plans. We had timelines. But somehow, we were all running in different directions like toddlers at a birthday party.
The messy middle ground.
Ever found yourself staring at a product roadmap that looks more like a Jackson Pollock painting than a clear path forward? That was us. Our company had spent weeks crafting a beautiful vision: “To revolutionise how people manage their personal finances.” Sounds lovely. But when asked what we were definitely building next Tuesday, everyone had a different answer.
The problem wasn’t our vision. The problem wasn’t even our execution. The problem was the messy, often ignored middle bit – the strategic roadmap that connects lofty dreams to daily actions.
Think of it like planning a road trip from Limerick to Galway. The vision is getting to Galway and having a lovely time. The execution is turning the steering wheel and pressing the pedals. But without a map that shows which roads to take, when to turn, and where to stop for a wee, you might end up in Donegal wondering what went wrong.
Breaking down the roadmap bones.
A proper strategic roadmap isn’t just a glorified to-do list or a pretty Gantt chart you create once and then ignore, like that gym membership you bought in January.
I learned this the hard way when our “revolutionary finance app” somehow morphed into three different products being built simultaneously. One team was focused on budgeting tools, another on investment tracking, and someone in the corner was quietly building a cryptocurrency exchange. I’m pretty sure we never discussed that last one.
Let’s start with the obvious perks:
First, it needs a clear vision at the top – the mountaintop you're climbing toward. Our team had that part sorted. "Help small businesses control their energy costs." Check.
Next comes strategic objectives – the big moves that get you toward that vision> This is where we started to wobble like a newborn foal. Our objectives included vague nonsense like "create innovative features" and "delight users." It's as helpful as saying you'll get to Galway by "moving westward."
The meat of any good roadmap is the initiatives and milestones – concrete, tangible things you'll build or achieve along the way. These aren't just features, mind you. They're outcomes. Not "build a budget tracker" but "help small businesses control their energy costs".
Finally, a roadmap needs clear timelines and owners. Without these, it's just a wish list. We had put target dates on our roadmap, but they were treated more like gentle suggestions than actual commitments.
When vision & execution
refuse to dance together.
Let me tell you about a time earlier in my career when I was the lead designer before I moved into product management. I had a clear grasp of our product vision. I could paint a picture of where we were headed and deliver talks about reimagining energy auditing user flows.
But when it came to the week-to-week design work? I could easily get off-script. One week, I’d be deep in high-concept operations dashboards we weren’t planning to build for another year. The next, I’d redesign our login flow—not because it was broken, but because I knew I could improve it.
It wasn’t about being difficult. It was a disconnect. Our roadmap didn’t bridge the gap between the lofty vision and the practical next steps. The strategy was floating up in the clouds while execution scrambled around at ground level. There was no ladder between them.
So we changed the approach. We built a vision alignment framework, something that could act as the spine, linking the head (our strategy) to the feet (our daily execution) and keeping everything moving in the same direction.
We took our vision and broke it down into three strategic objectives for the year:
- Help users understand where their money goes.
- Reduce financial anxiety through clear insights.
- Build sustainable saving habits.
Each objective had clear success metrics. Then we mapped our quarterly initiatives directly to these objectives. Every feature, every design task, every line of code could be traced back to one of these objectives. Suddenly, I had clarity.
When the roadmap meets reality.
The first test came when our biggest competitor launched a new feature that our sales team immediately wanted us to copy. In the past, this would have thrown our roadmap into chaos.
Instead, we evaluated the request against our strategic objectives. Did it help users understand their spending? No. Did it reduce financial anxiety? Maybe slightly. Did it build saving habits? Not really.
We decided not to derail our plans. Three weeks later, when we launched our dashboard, our user engagement jumped. Meanwhile, our competitor’s shiny new feature was barely getting used.
Of course, I’d love to tell you this was all smooth sailing from then on. It wasn’t. Our roadmap still faced attacks from all sides, such as sales requests, technical debt, and that one executive who gets a new idea every time he reads a tech blog.
The difference was that we now had a framework for handling these interruptions. Our roadmap wasn’t rigid; it evolved as we learned, but the strategic objectives remained stable, keeping our vision and execution aligned.
The map is not the territory.
The uncomfortable truth that most product articles won’t tell you is that your strategic roadmap will never perfectly match reality. It can’t. The market changes, technologies evolve, and sometimes your best developer quits to open a coffee shop in Lahinch.
Our team learned to treat our roadmap as a living document rather than holy scripture. We scheduled regular reviews every six weeks to check if our assumptions still held true. Sometimes, they didn’t, and we had to adjust.
The key was maintaining alignment between vision and execution even as the specific details changed. When we adjusted our roadmap, we didn’t just change timelines or features. We reexamined how each piece still connected to our strategic objectives and ultimate vision.
This wasn’t just project management bureaucracy. It was about building shared understanding. Everyone on the team knew not only what we were building but why. This shared purpose created resilience when things inevitably went sideways.
Maps, compasses,
& occasional detours.
A year after our roadmap overhaul, our finance app had gained significant traction. We hadn’t built everything we’d planned – some things took longer and proved unnecessary – but we’d stayed true to our strategic objectives.
The most surprising outcome wasn’t product success (though that was nice). It was team cohesion. People made better decisions independently because they understood how their work connected to our larger goals.
Looking back, I realize our initial problem wasn’t unique. Many teams struggle with the gap between inspiring vision statements and the daily grind of execution. Strategic roadmaps aren’t just planning tools – they’re translation devices that convert big dreams into concrete actions.
The roadmap doesn’t guarantee you’ll reach your destination exactly as planned. But it does ensure you’re all travelling in the same direction, taking detours together rather than wandering off separately into the wilderness.
And if you find yourself in a meeting room staring at a chaotic whiteboard, wondering how everyone got so confused about what you’re building – well, maybe it’s time to look at the map.
