💎 A roadmap is more than bullet points

My career began like many others, jumping at any gig that would give me an opportunity. Did I sell my soul to do so? No—but I did end up writing captions for social media, so you tell me. Eventually, I ended up at a company called Roadmunk where I cut my product teeth. My job? Creating roadmaps for people who create roadmaps. Pretty fucking meta, right?

My experience provided some incredible learnings about how to develop a company strategy and roadmap. I spent thousands of hours speaking with executives and leaders from companies we know and love, like Nike, Amazon, and The New York Times, peeking behind the curtain to see how multi-billion dollar decisions were made. It's one thing to spend $200 on sneakers, but $200 billion on product decisions? That’s when I felt like the Geek Squad staring at the motherboard.

Post-Roadmunk I was lucky enough to pick up some good roadmap habits at several other companies. However, I want to be clear that many mistakes were made. The facepalms were real and late-night thoughts of “I wish I didn’t…” felt worse. But ultimately, these reflections helped mold my understanding of what makes a roadmap successful.

Fast forward to today, and I'm hearing tales of leaders dumbfounded, wondering why their grand plan outlined in a four-bullet PowerPoint slide, isn't sparking "Mighty Ducks" level enthusiasm.

So it’s time we shared the ingredients to roadmaps that don’t suck. I’m not saying I can help you from afar hit every target, but I can say for certain your team will be on the same page and more excited by it. Some next-level focus. Alright, let’s get into it.

Roadmaps outline priorities

Ever feel like every time you turn around someone's asking, "What's the plan? What’s next?” Makes you wish you wore a sign saying I'm still figuring it out," right? But life doesn't quite work like that.

Let's be real, as much as it might sting, it's a valid question. It can feel like a little sting because it implies you haven't got it all sorted out. Prioritizing, though, that's where the real magic happens. Whether a big-shot CEO or a product guru, setting priorities can unlock a superpower. It's like finally organizing your closet so you're not asking your partner where your favorite shirt is every other day (…too close to home).

Good roadmaps? They’re like a GPS. They keep you on track and help you see the bigger picture. Plus, they're great for focus—no more rotating on your chair like a goldfish wondering what to tackle next.

Let’s be real, not every company has everyone on the same page about what comes next. But when you lay out what's crucial now and where we're all headed, everyone benefits. Everyone will have a sense of unity and shared purpose. Making everyone feel like they’re part of steering the ship, together. Always a good thing.

Roadmaps realize your vision

Your roadmap is the recipe that brings your vision to life. At its best? It’s used as the final climax when explaining quarterly and annual plans. Picture everyone nodding along as you explain how you’re going to realize that grand vision, hit goals, and address some meaningful problems. You’re mapping out a journey and momentum toward realizing your future.

Too often companies speak of their roadmap as a list of tasks or areas to fix. Sure, it has those, but it’s much more. It’s the blueprint for achieving your mission. So if you’re a company wondering what your mission is, start there. If you're a company with a mission being unused, start framing how you help customers through that lens. Share how this journey ahead (cough, roadmap) achieves your mission. Make it matter.

Roadmaps drive business results

It’s about time everyone learns a fundamental truth: a company must produce results. Of course, calculated risks are still part of the game. Let’s allocate 15% of your total R&D spend on things that are either necessary leaps of faith or failed experiments. This buffer leaves room for a few inevitable mistakes and future bets. However, the remaining 85% is dedicated to achieving tangible business outcomes within the year. It's about consistently providing exceptional value to your customers, driving revenue growth, and ensuring your team is fully aligned with this objective.

One of the cool things that happen when the company has a better sense of how each item makes an impact on the business—everyone builds a better product. That’s when results come at a greater rate. Like tides crashing against the shore. People not only brainstorm ideas but they craft business cases. They move from “Wouldn’t it be cool to build X?” to “Building X could reduce our churn by 5%”. That’s when you transform your novice operation into a formidable business. You start seeing more wins on the board. That continuous cycle of winning builds natural momentum. In turn, you’ve created a healthy rhythm in the company with better control over your fate when everyone learns what the levers are. People grow around you and your culture transforms.

If you find yourself in the middle of annual or quarterly planning and finding it hard, it is. But it gets a whole lot easier when you communicate priorities, articulate how they contribute to your vision, and ultimately lead to business outcomes. The added bonus? Your team gains clarity, focus, and renewed momentum.

Have fun with it. At the end of this cycle, you should feel excited that the company has the right ingredients to win and the ability to see the bigger picture. Need help along the way? Give me a shout and we’ll jam on it together.

Onwards,