How to create roadmaps worth following

Every company has two things: A high-level strategy for where it wants to be, and teams on the ground doing the work needed to get there. For some companies, these two things exist in vacuums.

This guide helps bridge that gap, keeping your people aligned, motivated, and focused on the bigger picture with a roadmap that tells them how their goals and projects are contributing to the organization's success.

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What’s in the guide?

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A framework for vision-making

How crafting a vision shapes your strategic plans.

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Transforming your vision into action

A strategic roadmap should serve as both a visionary blueprint and a dynamic tool for operational execution.

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Goals and goal getters

Balancing internal capabilities vs. future aspirations.

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Communication, monitoring, and adaptation

How to effectively communicate your plans, track progress, and adapt quickly.


What good is a roadmap that isn't followed?

Roadmapping is supposed to bring strategy and work together, telling teams, stakeholders, and executives not just what work is being done, but why it's being done.

However, without the right skills, tools, and information, roadmaps are difficult visualizations to create. The challenges range from how to make them look good to how to make them capable of facilitating an organization's success.

Here, we detail those challenges along with 5 best practices to make your roadmap effective and actionable.

By adopting and following them, you can keep your people aligned, motivated, and focused on the bigger picture with a roadmap that tells them just how their goals and projects are contributing to it.

 

 

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Common roadmapping challenges

Balancing priorities

One of the central challenges is knowing what to put on the roadmap. When there are lots of ideas and demands swirling around, it’s difficult to know which initiatives to tackle and which to sacrifice.

Project managers and product owners often need to bet on the bigger projects, which means some smaller projects getting axed or delayed. Understanding the benefits and tradeoffs of these decisions is not just a roadmapping challenge, but a project management one.

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Bringing teams together

All too often, different teams follow their own roadmaps. Combining them should drive efficiency, improve resource-sharing, and create a better sense of alignment — but bringing teams together isn’t easy.

There are often disagreements about a range of issues, such as which team owns the roadmap, whether it aligns with a specific agile methodology, or how necessary the roadmap is to begin with.

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Managing expectations

Executives are wondering why a new feature wasn’t released last week. The sales team want to know what’s coming up. The marketing team want to know when new products, features, and versions are being released.

When you arrive at a roadmap meeting, everyone will be expecting and fretting over different things. Using roadmaps to manage any mistaken or unrealistic demands is another central challenge.

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Getting project data into roadmaps

Teams already have projects and tasks and important contextual data about them in the platforms where they manage their work, like Jira.

However, unless there is an integration between the platform and the roadmapping tool, project details will need to be manually inputted into the roadmap. Not only is this hugely time-consuming and inefficient, it’s also very likely that some information won’t make it across.

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Structuring roadmaps

Should you choose a timeline? What’s the best way of structuring a more agile “no dates” roadmap? What about if you want dates but not hard deadlines?

Companies often struggle to know how best to structure a roadmap and many just settle for a list, but lists aren’t visual or engaging and list-based roadmaps are often ignored.

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Building roadmaps in spreadsheets or slides

In spreadsheets and presentation software, roadmaps have to be built from scratch without the kind of automation and templates that come with purpose-built roadmapping tools.

Cue lots of time-sucking manual effort, duplication, and mistakes.

What’s more, they will need to be continually updated because the data won’t be live.

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Inadequate tools

Whatever tool you use needs to have certain features and functionalities for your roadmap to be an actionable, boardroom-ready, and living document. However, many roadmap builders find themselves unable to structure, format, or customize their roadmap to best suit their audience.

With legacy tools, it’s very difficult to create a roadmap that looks good, is easy to understand, and includes all the visual markers you need to communicate to stakeholders, such as priorities, dependencies, and milestones.

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Overengineered tools

At the other end of the spectrum, a lot of roadmapping tools are overengineered and too complex, which makes them tricky to learn. As a result, people either don’t use them or don’t use them efficiently.

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Sharing roadmaps

Roadmaps are a communication tool, but that communication has to be two-way. A static spreadsheet shared by email won’t foster much transparency or collaboration, and many great roadmaps fall down because the people they’re meant for aren’t interacting with them.

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Keeping roadmaps relevant

Research and collaboration informs what objectives and initiatives end up on your roadmaps. Things like engagement stats, business growth metrics, and product feature usage as well as market, team, and user insights.

The problem is that many project managers stop gathering this data after the roadmap has been created, making it less relevant and useful a short while later. To serve its purpose as a strategic tool, a roadmap should be a living document that evolves as your teams, customers, and strategy do.

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5 best practices for making actionable roadmaps

Now let's dive into how to solve these challenges. Following these best practices will ensure your roadmap is capable of turning high-level strategy into actionable tasks and, down the road, organizational success.

Roadmaps worth following - make roadmapping collaborative

1. Make roadmapping a collaborative, research-driven process before, during, and after

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. To keep your roadmaps relevant, involve your stakeholders in their creation and evolution. 

Encourage feedback and collaboration from team members so your roadmap accurately reflects what everyone needs to do and why. 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. 

Roadmaps worth following - make roadmapping collaborative
Roadmaps worth following - Roadmaps worth following - break down initiatives into smaller components

2. Break down big goals and initiatives into smaller components

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

On an organizational strategy roadmap, a goal might be to "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 e-commerce 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 for Jira to visualize everything in a granular hierarchy. 

Roadmaps worth following - make roadmaps that are visually engaging

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 if your company's 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 trying to accomplish. 

A lighter, simpler roadmap can be more effective than an overly complex one.

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.

Roadmaps worth following - make roadmaps that are visually engaging
Roadmaps worth following - use a tool to build quickly and effectively

4. Use a tool to build quickly and efficiently

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

It should let you roll up multiple roadmaps into a portfolio roadmap, so you can get an at-a-glance view of how different teams, product lines, and programs fit together without starting from scratch. To minimize admin, confusion, and error, when something changes in the source roadmaps, this should sync to the portfolio roadmap -- and vice versa.

You also want a tool that presents live data that 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.

Something else that makes roadmaps quicker and easier? 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.

Roadmaps worth following - use milestones and KPIs

5. Use milestones and KPIs for measuring roadmap effectiveness

Milestones and key performance indicators (KPIs) keep team momentum strong and provide quantifiable metrics for objectively measuring the progress and success of your initiatives.

Without KPIs, it's impossible to know if your roadmap is effective. KPIs on roadmaps serve a number of other purposes as well:

  • 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 stakeholders

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

Roadmaps worth following - use milestones and KPIs

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