Roadmaps that Matter: A Guide to Strategic Planning and Execution

1. Make Roadmapping a Collaborative, Research-Driven Process Before, During, and After

Effective roadmapping at the middle-management level requires cross-functional collaboration. This means sharing goals and resources between departments, avoiding silos, and ensuring that leadership sees the interconnectedness of each team's work.

Roadmaps should be dynamic and flexible as the messages they contain will need to adapt quickly according to changing circumstances.

They should never be treated as static documents. In order to keep your roadmaps relevant, involve your stakeholders and leadership in their creation and evolution.

Your roadmap should be flexible enough to adapt to the way each team works, ensuring it remains useful as your company scales.

Most importantly, keep gathering market and user insights and conduct regular reviews of progress. Be prepared to adjust initiatives based on resource changes, evolving customer needs, and unforeseen events.

[Visual: Representation of cross-functional team collaboration in roadmapping, showing Sales Team, Product, Marketing, Dev, Strategy, Outreach, Growth.]

2. Break Down Big Goals and Initiatives into Smaller Components

Goals and tasks that are vague or too big to achieve aren't useful in a practical sense.

On an organizational strategy roadmap, a goal might be “increase market share" but this lacks doable and measurable steps.

Translate vague goals like this into SMART goals (specific, measurable, achievable, relevant, and time-bound), e.g. “launch a new product line in Q4” or “expand into new geographic markets in Q2”.

Similarly, on a marketing tactics roadmap, you could have “launch a new ecommerce website". This is too big a job to be represented as a single item on a roadmap and will likely involve multiple team members.

If you break the job down into smaller ones, you'll have individual projects and tasks that can be assigned, tracked, and completed in nice, manageable chunks.

If your roadmapping tool can account for how projects are linked together, you'll have even better insights into dependencies, resource sharing, and more accurate timelines for project completion.

Once you have objectives and projects defined on a roadmap and you're ready to start working on them, you can use a tool like Structure PPM for visualizing everything in a granular hierarchy, as shown below.

• Project X
  • INIT-3 [warning] At Risk
  • Epic A STR-1
    • Task A STR-6 [check] On Track
    • Task B STR-9 [check] On Track
    • Sub-Task 1 STR-14 [check] On Track
• Project Y INIT-4 [high risk] High Risk
  • Epic B ARR-2 [warning] At Risk
  • Epic BB ARR-3 [check] On Track

3. Make Roadmaps That Are Visually Engaging and Rooted in Your Culture

To know how best to structure your roadmap, you first need to think about your culture. If deadlines are important to your company, your roadmap should reflect that.

If your teams are agile and require flexibility, or you're a company whose priorities are constantly shifting, then a roadmap without hard deadlines will be more appropriate. You might also need something in between: dates but not deadlines.

Next you need to think about the story you're trying to tell, and the best way of telling it.

If your roadmap is a list of objectives and initiatives on a spreadsheet, people's eyes will glaze over.

Roadmaps need to be visual, e.g. a timeline or swimlane, to make it easy for everyone in your strategy meetings to understand what the organization is planning to accomplish.

Use clear, color-coded milestones and dependencies to create a quick-view version of your roadmap for leadership while maintaining a more detailed view for your team.

Example Roadmap (Q1-Q2)

You should add visual markers for milestones, linked and dependent items, and priorities to highlight the things teams should remember. Color palettes are useful for customizing roadmaps, showcasing brand, and generally making them more attractive. But you can also use color-coding to visualize an additional layer of relationships between items.

Importantly, don't let your roadmaps become messy. Reorganize and pivot data to make it more manageable for the audience.

For example, a roadmap of a company's tactics for the first two quarters could easily end up looking like six laundry lists. Not only is this daunting to the team, it's difficult to see where any of the items sit strategically.

Now imagine pivoting on initiatives, i.e. creating subgroups for each month. The roadmap will instantly highlight that a team is focusing heavily on retention in Q1 and new features in Q2. These kinds of pivots make roadmaps much more compelling.

Example Roadmap by Initiative (Q1-Q2)

4. Use a Tool to Build Quickly and Efficiently

For middle managers, time spent creating and updating roadmaps takes away from the team's productivity.

Use a tool that integrates directly with your work management systems to ensure you're sharing up-to-date insights with leadership without spending hours on manual updates.

Choose a purpose-built roadmapping application that offers templates, format layouts, and automation for making roadmaps in a few clicks.

You also want a tool that presents live data which auto-updates as initiatives are completed, so you're not rewriting your roadmaps every other day. This means a tool that will integrate and sync with your work management systems, eliminating copy-paste and import-export efforts and creating real-time roadmaps that stay useful.

[Visual: Screenshot of a task management interface showing "System Launch Testing" with details like assignee, progress, and link to Jira.]

Something else that makes roadmapping quicker and easier is a filtering tool that lets you tailor your roadmaps to display only items that are relevant to a specific audience. This enables you to keep initiatives combined on the same roadmap – rather than spread across dozens – making them easier to manage and monitor.

5. Use Milestones and KPIs for Measuring Roadmap Effectiveness

By incorporating KPIs, you can give leadership a clear, quantifiable view of your team's impact on strategic goals. This builds trust with leadership, aligns your team's work with their priorities, and gives you data to advocate for resources or adjustments as needed.

Without KPIs, it's impossible to know if your roadmap is effective.

KPIs on roadmaps serve a number of other purposes as well. They:

• Keep initiatives aligned with overarching organizational goals
• Make team members aware of the specific metrics they're responsible for, fostering a culture of transparency, ownership, and accountability
• Serve as early warning indicators; if a KPI starts to deviate from the target, it signals a potential issue that needs to be addressed for the project to stay on track
• Allow organizations to assess the return on investment (ROI) from each initiative, and
• Demonstrate progress to senior leadership.

Overall, milestones and KPIs make it easier for everyone to see what has been achieved and what is still to come.

[Visual: Representation of milestones and KPIs, showing progress towards goals.]

CARFAX x Strategic Roadmaps

How CARFAX used the five best practices of roadmapping to eliminate their pain points:

Microsoft Excel does a lot of stuff, but it's a one-size-fits-all generic piece of software. So if you want to make roadmaps, don't expect any shortcuts.

CARFAX, which supplies millions of Canadians and Americans with vehicle history reports, learned the hard way how unwieldy Excel is for making roadmaps.

For years they had one big Excel-based roadmap with joined cells and merged data. They would copy portions of it into Microsoft PowerPoint before adding overlays to draw attention to different elements. It was a tedious and time-consuming process that was painful to update each month.

When CARFAX implemented Strategic Roadmaps, all that stress went away. It became so much easier to show who's working on what and how it's connected to their strategy. Strategic Roadmaps' automation, integration with Jira, and drag-and-drop customizations made building and updating CARFAX's roadmaps easy and quick.

Moreover, Strategic Roadmaps are dynamic, live documents. So CARFAX no longer had to wait for updated Excel files to be passed around. Roadmapping became a more open, collaborative, and efficient process, with the new roadmaps always reflecting the reality of the situation at that moment in time.

Structure and Strategic Roadmaps: The Secret to Aligning Strategic Planning with Execution

Let's face it – senior leadership won't use Jira, no matter how much you try. Which means that, for now, you're stuck pasting screenshots into PowerPoint for every weekly report. Sound familiar?

It doesn't have to be this way. With the new Structure and Strategic Roadmaps integration, you can generate accurate, high-level reports in minutes.

By combining Structure's project data rollups and powerful formulas with Strategic Roadmaps' visualization, you gain big-picture insights without sacrificing detail. This integration keeps you in control with up-to-date summaries and clear visibility at every critical level, helping you convey complex project information in a format that leadership can quickly understand.

Learn more at: www.tempo.io/integrations/structure-and-roadmaps or dive into the webinar rundown here.