Building the Yellow Brick Road(map)

This is Part One of a series on building, monitoring, and pivoting a data roadmap. Stay tuned for additional content on this topic!

It’s your first month as head of data at your new company. You’ve been a star individual contributor for the last few years, and you’ve finally taken the next step into a leadership role.

Your goal? Define the vision for your team and function.

But you are missing key context. At this stage, you don’t have a clear sense of the business, how teams interact with data, or the organization’s most pressing problems. So you embark on a crucial first step: listening.

You begin to hear some insightful conversations.

“We have no visibility into real-time LTV-to-CAC. We’re spending dollars aimlessly.”

Ah, yes! You recognize a need to improve the attribution & customer lifecycle measurement framework. Robust measurement = more efficient marketing spend 📺

“Our product team doesn’t understand how to improve conversion rate or measure feature success.”

Been there, done that! We need a clean event taxonomy and to build a workflow that ties success metrics with their underlying tracking before feature launch 📓

“We need a centralized source of truth for revenue reporting. Our numbers are all over the place.”

The age-old “doesn’t match my spreadsheet” problem. In comes centralized unit economics and revenue reporting to the rescue 🦸

You end your listening tour with a vision:

You have the vision. You have projects to tackle and a high-powered team to execute these projects.

Now what?

Building the Roadmap

Roadmapping is a powerful tool for any leader. The ability to translate needs into a strategic plan builds cross-functional alignment and clarifies dependencies. Your team does not live in a silo, and your work means little if other teams are not moving toward the same goals. Roadmapping is how you make that alignment real.

Here's a tried and true process for building your team's first roadmap.

Step 1: Idea Generation

The first step is to compile a list of all possible opportunities that could drive value for the business. You’ve already done the hard part of defining the team's vision; now it’s time to plan for it.

About 4-6 weeks until the start of the quarter/year/etc, start the idea generation phase by:

1. Understanding the priorities of your colleagues. As the leader of the data function, you should meet regularly with other functional leaders to understand their concerns and priorities. As you start the idea-generation phase, use the 1:1 time to ensure you have a clear handle on future priorities. One hack is to use more rigid plans (i.e., a product roadmap) as an input to your data roadmap. For example, if your org is planning to release a new feature or product next quarter, include A/B experimentation and measurement support on your roadmap.

2. Leveraging your experience. What worked well at other companies that could work well here? If you’ve reached this part of your career, you’ve likely done a few things right, or at the very least, seen them done right. You’re now at a new company with new gaps. Identify these gaps and build successes based on past experiences into your roadmap.

3. Auditing existing processes. Do you face any recurring issues internally, such as data quality, CI/CD checks, or development velocity? Are there easy wins (tools or processes you can implement) to improve release cycles and the quality of your team’s work?

Note: do not let your past experience be a limiting factor in this phase! You can always bring in external support, hire a specialist, or stretch the skill set of your existing team.

Step 2: Build the Rough Draft

About 2-4 weeks out, build the rough draft.

Given all the generated ideas, use a prioritization framework of your choice to estimate the impact, effort, and confidence for each idea. Use whichever method best fits your working style.

After all potential projects are ranked and filed, put pen to paper and match the effort with your team’s current capacity. Use the inputs you have at your disposal, such as your team’s current development velocity and capacity, upcoming organizational changes, expected impact, etc., to outline a plan that balances impact with feasibility.

One common pitfall that leaders often face: how do we estimate the level of effort?

There’s a common Bill Gates quote that goes something like “Most people overestimate what they can achieve in a year and underestimate what they can achieve in ten years.”

With respect to planning, the general rule of thumb should be to overestimate the amount of time each project will take.

Step 3: Socialize the Rough Draft

It is extremely important to pressure test your roadmap in 1:1s during these weeks. Known as the “meeting(s) before the meeting”, your goal is to socialize ideas, gain buy-in, and address potential objections before the formal meeting.

Does the roadmap include all high-priority items from stakeholders? What are the biggest risks?

One small surprise can derail an otherwise successful roadmap session, so prepare effectively!

Step 4: Finalize the Roadmap with the Wider Group

By 1-2 weeks out, the roadmap should be in a near-final state. You’ve pressure-tested the plans individually with stakeholders and feel confident that you’re focusing on the right things. There might be a few lingering questions, but for the most part, you should be in a pretty good spot.

Use the finalization call to outline any last-minute changes, spitball requirements, and discuss risks.

In these conversations, there may be contention around prioritization. Do not be afraid to propose expanding capacity—via internal hiring or short-term external support—as a lever to drive greater impact and meet your stakeholders' needs.

Step 5: Share the Final Roadmap

Congrats! You’ve identified the most valuable data projects for the company, laid the path forward, and secured alignment on the plan. Now, time to condense the roadmap into an easily readable format and post it in your org-wide data Slack channel.

Closing thoughts

Data teams are internally-facing teams. Your stakeholders are within the company, not outside it. Their goals are your goals; you win when they win. By formalizing their needs into a clear plan of action, you enable their success.

That’s where roadmapping comes in. It turns stakeholder needs into an organized, shared plan, helping your team move from reactive support to proactive partnership.

Roadmapping is a powerful skill that takes time to develop, and starting this process can feel very intimidating for the first time. If partaking in a full-on roadmapping session feels intimidating to you, take baby steps to get there. Start with 1:1s with key stakeholders to build trust. Tease “quarterly goals” at the start of each quarter. Work your way up to the point where this process feels natural and not forced.