Sharing Progress with Roadmaps

What's the biggest gap in your roadmap process? 

Is it prioritization, where everything feels important, or the difficulty of keeping status and progress up-to-date? Perhaps it's the challenge of keeping stakeholders in the loop, or weighing trade-offs when you need to pivot.

We understand these challenges and Shortcut's Roadmap can help you address them. It's an effective tool for your team to use to communicate asynchronously about focus and progress. At any given time, anyone in your organization can visit your team's roadmap and quickly get an understanding of what's being worked on, when it will be delivered and understand the overall vision for your team's deliverables. It's also a place to highlight projects that could be at risk due to missed deadlines, scope, or dependencies. 

Our Head of Product, Jordan LaCount, and Dan Nestor, our Customer Advisory Manager, hosted a webinar where they discussed setting up the Roadmap, the main challenges in the process, and the importance of keeping health updates and roadmaps consistent. Watch the recording here.

Let's take a quick look at how to set up your Roadmap and some best practices:

🎯 Set Objectives

Before you start building your roadmap, take a step back. First ask yourself: What are our business goals and objectives? If you already have them set, now's the perfect time for a quick review. If not, it's time to get those goals on paper (or screen), as they'll guide the decisions that follow.

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🗺️ Creating the Roadmap

Now that your objectives are in place, it’s time to map out the journey. Start by customizing a list of deliverables that will help you hit those goals. Keep it collaborative—invite your Product, Design, and Engineering leads to the table. Together, you can weigh the impact and effort of each deliverable. Don’t overcomplicate things; simple RICE (Reach, Impact, Confidence, Effort) scoring can be really helpful here!

Once you've prioritized, connect those Epics to the Objectives and Key Results (OKRs) they’ll impact. This connection not only keeps your team aligned but also shows everyone how their work contributes to the bigger picture.

💡 Pro Tip: Create your roadmap on a Quarterly or Semi-Annual basis. But remember, this roadmap isn’t set in stone—it's more like a flexible guide. As you measure impact and track progress, be prepared to adjust and pivot as needed.

Setting up your Roadmap in Shortcut

The Roadmap is organized by teams, and each team's grouping is built by adding the Epics your team is focusing on. You can reorder the Epics by priority, delivery date, or whatever works for your team.

Customize What You See

To keep your Roadmap view focused, you can customize what's shown and their placement. This includes things like name, state, progress, and objectives. You might want to change your view depending on what stage you are in the planning process.

Adding Health

Adding a Health status with a contextual comment to indicate what's on track, off track, or at risk can help provide asynchronous updates. This quickly signals to anyone viewing the Roadmap where things are at and if there's anything that needs to be discussed.

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Filtering your View

Use filters for various combinations of views once your Roadmap is created to get important snapshots of focused information.

Sharing the Roadmap

You can export your Roadmap to share it with your team. For example, you might want to focus your filters to show only what's in development to indicate current priorities before you share it on Slack!

The Roadmap provides big-picture content for what you'll build and enables teams to convey the details of what's coming and when.

💡 Pro Tips:

• Share a link to the Roadmap page. Better yet, bookmark it in Slack or your regular meeting invites
• Set a Slack reminder for Epic Owners to update Health and stakeholder communications

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🔄 Retro and Reflection

After you’ve navigated through a release phase, take some time to reflect. Bring those business outcomes back to the group for a retrospective. What worked? What didn’t? Analyzing this will help you fine-tune future roadmaps and avoid repeating past mistakes.

💡 Pro Tip: Once you’ve retroed and analyzed the impact, clear out the clutter. Remove completed Epics from your roadmap to keep it fresh and focused.

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Ready to take your team's roadmap to the next level? Start a free trial of Shortcut today! 

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