How To Build A Roadmap

Few artifacts generate as much debate, and occasionally, dysfunction as the product roadmap. While intended to provide direction and alignment, roadmaps often become battlegrounds where different stakeholders push competing agendas, or worse, devolve into delivery date commitments that bear little relation to actual customer value. This article explores how to create roadmaps that drive alignment while maintaining the flexibility needed for effective product development.

Strategic Roadmaps vs. Delivery Plans

At its core, a strategic roadmap communicates the sequence of problems to solve and opportunities to address.

A delivery plan details specific implementation timelines for decomposed components.

This distinction is fundamental but frequently overlooked, leading to confusion and dysfunction in product organisations.

The most common roadmap mistake is treating it as a series of feature delivery dates rather than a visualization of strategy. A roadmap should communicate direction and alignment, not commitments to specific timelines for uncertain work.

The Architecture of Strategic Roadmaps

Effective strategic roadmaps share several key architectural elements, regardless of the specific format or visualization used.

Organisational Components

A well-structured roadmap typically includes:

• Themes or Opportunity Areas: Broad categories of customer problems or business opportunities that the product will address. These themes create natural groupings for related work and help stakeholders understand the strategic focus areas.
• Outcomes and Success Metrics: Clear articulation of what success looks like for each theme, often expressed as measurable outcomes for customers and the business. These metrics provide the basis for evaluating progress and impact.
• Timeframes: General time horizons that communicate sequence and priority without making specific date commitments for uncertain work. These might be expressed as quarters, "Now/Next/Later," or other relative timeframes.
• Confidence Levels: Indications of certainty that help set appropriate expectations for different roadmap elements. Items in the near term typically have higher confidence than those farther out.

Roadmap Structure

One of the most powerful aspects of strategic roadmaps is their progressive time horizon approach:

• Near-term items (typically the next 1-2 months) may include specific solutions with relatively high confidence, as teams have done sufficient discovery to validate solution approaches.
• Mid-term items (typically 3-6 months out) focus more on the opportunities to be addressed, with potential solutions identified but still subject to discovery and validation.
• Long-term items (beyond 6 months) emphasize outcomes and themes with limited solution specificity, acknowledging the uncertainty inherent in longer planning horizons.

Connecting North Star Metrics to Roadmaps

The most effective roadmaps establish clear connections to North Star Metrics, creating a line of sight from strategic direction to tactical execution. This connection ensures that roadmap priorities genuinely drive progress toward what matters most for the business.

Building Strategic Roadmaps: A Step-by-Step Guide

Creating effective strategic roadmaps requires a structured approach that balances strategic direction with discovery and flexibility. Here's a practical process for developing roadmaps that drive alignment while remaining adaptable.

Step 1: Establish Strategic Context

The foundation of any effective roadmap is clear strategic context. This includes understanding your North Star Metric, key business objectives, competitive landscape, and customer needs. This context ensures the roadmap reflects strategic priorities rather than just collecting feature requests.

Step 2: Identify Key Themes and Opportunity Areas

With strategic context established, the next step is identifying the major themes or opportunity areas that will organize your roadmap. These themes should connect directly to your North Star Metric and strategic objectives while addressing significant customer needs.

Buffer's roadmap development demonstrates this approach. When reshaping their roadmap for their publishing platform, they identified four key themes based on customer research and strategic objectives:

• Improving content planning and workflow
• Enhancing performance analytics
• Streamlining approval processes
• Expanding publishing channel support

Each theme connected directly to their North Star of "increasing successful posts per user" while addressing specific customer pain points identified through research. The themes were broad enough to encompass multiple potential solutions but specific enough to provide clear direction.

Effective themes share several characteristics:

• They focus on customer problems or needs rather than specific features
• They connect directly to strategic objectives and North Star Metrics
• They encompass related opportunities that can be addressed over time
• They can be translated into measurable outcomes

The goal is creating 3-5 major themes that will organize your roadmap and communicate strategic priorities clearly to stakeholders.

Step 3: Develop Measurable Outcomes for Each Theme

For each theme, define measurable outcomes that indicate progress. These outcomes translate strategic direction into evaluable results without prescribing specific solutions.

LinkedIn's Jobs product team exemplifies this approach. For their theme of "Improving Candidate Match Quality," they defined specific outcomes:

• Increase application completion rate from 30% to 45%
• Reduce time-to-hire for posted positions by 20%
• Increase hiring manager satisfaction with candidate quality from 70% to 85%

These outcomes provided clear success metrics without dictating how the team would achieve them. They created space for discovery and innovation while establishing accountability for results.

When developing outcomes, consider several questions:

• How will we know if we've successfully addressed this opportunity?
• What metrics would indicate we're creating customer and business value?
• How do these outcomes connect to our North Star Metric?
• Are these outcomes achievable within our planning horizon?

The most effective outcomes strike a balance—specific enough to guide decision-making and evaluate progress, but not so prescriptive that they presume particular solutions.

Step 4: Sequence Themes and Opportunities

With themes and outcomes defined, the next step is determining the sequence in which you'll address them. This sequencing creates the temporal structure of your roadmap and communicates priorities to stakeholders.

Basecamp's approach to sequencing provides an instructive example. Rather than trying to work on all themes simultaneously, they focus intensively on a few priority areas in each development cycle. Their sequencing considers several factors:

• Strategic importance: Which opportunities most directly impact their North Star?
• Dependencies: Which capabilities need to be built first to enable future work?
• Risk reduction: Which unknowns need early exploration to reduce project risk?
• Resource alignment: How can they sequence work to maximize team effectiveness?

The result is a clear sequence that communicates both priorities and rationale, helping stakeholders understand not just what will come first, but why.

When sequencing your roadmap, consider these approaches:

• Impact mapping: Assess each opportunity's potential impact on your North Star Metric
• Dependency analysis: Identify technical or capability prerequisites that influence sequence
• Effort-impact analysis: Balance potential value against required investment
• Customer journey mapping: Address opportunities in the sequence customers experience them

The outcome should be a clear sequence of themes and opportunities that communicates strategic priorities while creating a logical progression for capability development.

Step 5: Define Appropriate Time Horizons

Strategic roadmaps require appropriate time horizons that balance clarity with uncertainty. Rather than assigning specific dates to all initiatives, effective roadmaps use timeframes appropriate to confidence levels.

GitLab's roadmap approach demonstrates this principle. They use three-time horizons with decreasing specificity:

• Current iteration (3 months): Specific features with defined scope and milestones
• Coming soon (3-6 months): Opportunity areas with potential approaches being explored
• Future direction (6+ months): Strategic themes without specific implementation details

This approach sets appropriate expectations for different time horizons. Near-term items have specific details as teams have completed sufficient discovery to understand what they're building. Longer-term items focus on problems to solve rather than solution specifics, acknowledging that discovery will continue to shape approaches.

When defining time horizons, consider:

• Using relative timeframes (Now/Next/Later) rather than specific dates for uncertain work
• Creating more granular timeframes for near-term items (where confidence is higher)
• Using broader timeframes for distant items (where uncertainty is greater)
• Explicitly indicating confidence levels for different roadmap elements

The goal is creating appropriate expectations for different planning horizons while maintaining strategic clarity.

Step 6: Create Learning Milestones

One of the most valuable but often overlooked elements of strategic roadmaps is the inclusion of explicit learning milestones. These milestones acknowledge the discovery process and create accountability for knowledge accumulation alongside delivery.

Airbnb's roadmap for their Experiences product demonstrates this approach. Alongside delivery milestones, their roadmap included explicit learning milestones:

• Complete research on host onboarding friction points
• Validate pricing model with hosts in three test markets
• Evaluate competitive offerings in emerging experience categories

These learning milestones created space for discovery while maintaining accountability. They also helped stakeholders understand that learning represented valuable progress, even when not immediately resulting in shipped features.

Effective learning milestones have several characteristics:

• They focus on specific knowledge gaps or assumptions that need validation
• They have clear completion criteria (what specifically will be learned)
• They include research methods and participant parameters
• They connect directly to upcoming roadmap decisions

By incorporating learning milestones, roadmaps acknowledge the reality that product development requires discovery alongside delivery.

Common Roadmap Anti-Patterns

Several common practices undermine the effectiveness of product roadmaps. Understanding these anti-patterns helps teams avoid dysfunctional roadmapping approaches.

1. The Feature Factory Roadmap

Perhaps the most common anti-pattern is the feature-oriented roadmap with no clear connection to outcomes or strategic objectives. These roadmaps list features without explaining why they matter or how they contribute to customer and business success.

Signs you might have a feature factory roadmap include:

• Roadmap items described as features or solutions without explaining customer problems
• Success defined by shipping rather than outcome metrics
• Stakeholder discussions focused on feature requests rather than strategic priorities
• Limited connection between roadmap items and North Star Metrics

2. The Sales Appeasement Roadmap

Another common anti-pattern emerges when roadmaps become primarily tools for managing sales relationships rather than strategic planning documents. These roadmaps promise specific features by specific dates to close deals, creating both dysfunctional priorities and unrealistic commitments.

Indicators of a sales appeasement roadmap include:

• Frequent commitments to specific features by specific dates for specific customers
• Roadmap priorities changing based on recent deal losses
• Feature value measured primarily by associated sales opportunities
• Limited connection between roadmap items and overall product strategy

3. The Wishful Thinking Timeline

Many roadmaps suffer from unrealistic timelines that ignore both uncertainty and implementation capacity. These roadmaps present aspirational plans disconnected from reality, creating false expectations and inevitable disappointment.

Warning signs of the wishful thinking timeline include:

• Detailed feature specifications for distant future quarters
• Limited consideration of discovery and validation time
• Roadmap dates consistently missed but future dates not adjusted
• Planning that assumes perfect execution without contingency

4. The Immutable Contract

The final common anti-pattern treats roadmaps as immutable contracts rather than living documents that evolve with learning. These roadmaps become rigid commitments that prevent adaptation as new information emerges.

Signs of the immutable contract roadmap include:

• Roadmap changes viewed as failures rather than appropriate adaptations
• Limited explicit learning milestones or discovery activities
• Stakeholder frustration when priorities shift based on new information
• Teams pursuing committed approaches despite evidence suggesting alternatives

Conclusion: Roadmaps as Strategic Tools

Truly strategic roadmaps serve as powerful tools for aligning organizations around opportunities that matter most for customers and the business. By connecting North Star Metrics to customer opportunities and potential solutions, they create a coherent framework for product development that balances strategic direction with discovery and adaptation.

The shift from feature-oriented delivery dates to outcome-focused opportunity sequencing transforms roadmap discussions from feature debates to strategic conversations. It helps organizations focus on the problems worth solving rather than getting lost in solution details prematurely.

Most importantly, strategic roadmaps acknowledge the fundamental nature of product development—a journey of discovery where learning and adaptation are essential elements of progress. By creating space for this discovery while maintaining strategic direction, roadmaps can fulfil their potential as tools for alignment and communication rather than sources of dysfunction and false certainty.

As you develop your own approach to roadmapping, remember that the goal isn't perfect prediction but rather creating a framework that enables teams to make good decisions in the face of uncertainty. With clear connections to your North Star, focus on customer opportunities, appropriate time horizons, and regular review cycles, your roadmap can become a powerful tool for creating products that genuinely solve customer problems while driving business success.