Start with Why: Why We Are Building RoadmapOne

In “Start with Why ,” Simon Sinek presents a powerful concept: great leaders and organizations inspire action by first explaining why they do what they do before explaining what they do or how they do it.

So here’s my rationale for building RoadmapOne, and how I hope that it makes organisations slightly better for everybody.

The Roadmap Challenge

I’ve been a CTO and CTPO for more than 20 years. During that time I’ve done a lot of things that didn’t work, and a few things that did. Now that I’m doing advisory and Non-Exec work with different companies and different sectors, I keep seeing the same pain points:

• Product teams struggling to clearly demonstrate the business value of their roadmaps
• Misalignment between engineering resources and strategic business priorities
• Leadership teams lacking visibility into how resources are allocated across initiatives
• Stakeholders asking “Why are we building this?” while teams scramble to articulate value
• Initiatives being approved without clear connections to measurable business outcomes
• Engineering teams spending huge amounts of time building (and justifying why they are building) “enabling” tools, while ignoring initiatives that could drive the business.

These issues are all symptoms of a deeper problem in how organizations approach roadmapping.

The “Why” Behind RoadmapOne

As Sinek explains, truly inspirational leadership begins with purpose. For RoadmapOne, our “why” is crystal clear: We believe product teams deserve a better way to connect their work to measurable business value while gaining organizational alignment around resource allocation.

This isn’t just about creating another project management tool (in fact, if you’re a project manager, then RoadmapOne is really not for you). It’s about fundamentally shifting how product organizations think about their roadmaps—from output-focused lists of features to outcome-focused strategic alignment tools.

I’ve implemented the RoadmapOne approach at multple different organisations and (so far), it’s always made a meaningful and measureable difference to the organisation.

Aligning Resources with Outcomes

The traditional roadmap is often disconnected from business strategy. Teams track what they’re building, but rarely connect those efforts directly to tangible business results like:

• Increasing onboarding conversion from 15% to 25%
• Reducing customer churn from 15% to 12%
• Decreasing cost per acquisition from £4 to £2.50
• Achieving regulatory compliance by a specific deadline
• Reducing critical security issues from 7 to zero

Each of these represents a clear, measurable outcome that executives, board members, and stakeholders can immediately recognize as valuable. And yet, most roadmaps fail to make these connections explicit.

From Output to Outcome

RoadmapOne was built specifically to address this disconnect by:

1. Centering on Initiatives and Objectives that directly impact financial performance or business sustainability
2. Providing visibility into resource allocation across teams, sprints, and quarters
3. Empowering teams to define their own Key Results for objectives, following the SVPG Product Model where leadership allocates objectives and teams determine how to achieve them
4. Creating transparency around capacity so organizations can have honest conversations about prioritization
5. Visualizing the distribution of resources to ensure highest-priority initiatives receive appropriate support

This approach shifts the conversation from “What are we building?” to “Why are we building it and what outcomes will it deliver?”

The Golden Circle Applied to Product Management

Sinek’s model of the Golden Circle—Why, How, and What—maps perfectly to effective product management:

• WHY: The business Objectives we aim to achieve (increase conversion, reduce churn, etc.)
• HOW: The key results teams will deliver to reach those outcomes
• WHAT: The specific features and capabilities teams will build

Most roadmap tools start with the “What.” RoadmapOne deliberately starts with the “Why.”

The Hidden Cost of Misalignment

The cost of failing to connect roadmaps to business value isn’t just theoretical—it’s enormously expensive. Organizations waste millions on:

• Building features nobody uses
• Pursuing initiatives disconnected from strategic goals
• Staffing teams to work on lower-impact projects while high-value opportunities languish
• Responding to whoever shouts loudest rather than what delivers most value

This misalignment creates frustration across the organization. Product teams feel undervalued and misunderstood. Leadership teams question the ROI of product investments. Engineers wonder if their work matters.

A New Approach

RoadmapOne represents a fundamental rethinking of how roadmaps should work:

1. Start with business objectives that executives and board members instantly recognize as valuable
2. Allocate those objectives across the squads with clear, measurable targets
3. Visualize resource allocation across teams, quarters, and priorities
4. Enable data-informed conversations about priorities and trade-offs
5. Provide transparency into what’s being built, when, by whom, and most importantly—why
6. Ensure squads are empowered to determine how to achive the objective

This isn’t just better roadmapping—it’s better business.

Your Own Golden Circle

As you think about your own product management challenges, I encourage you to apply Sinek’s Golden Circle:

• WHY: What business outcomes are you trying to achieve?
• HOW: What measurable key results will indicate success?
• WHAT: What specific features and capabilities will deliver those results?

If you can’t clearly articulate your “why,” you might be building the wrong things.

Join Our Mission

At RoadmapOne, our mission is to transform how organizations approach product roadmapping—from feature factories to strategic business partners. We believe product teams deserve better tools to demonstrate their value and align their work with organizational priorities.

If you’ve experienced the frustration of disconnected roadmaps, resource allocation challenges, or struggles to articulate the value of product work, we built RoadmapOne for you.

Start with why. The rest will follow.