Sharing Progress with Milestones and Markers
To keep your roadmap simple while also making communicating progress easier, use Milestones and Markers to tie effort and time to measurable progress without creating false certainty or constraints.
Roadmaps are supposed to be simple. Many product roadmaps are anything but.
One of the most helpful ways I’ve found to keep roadmaps clear and lightweight is using a Now-Next-Later outcome roadmap. When done right, they’re simple by design: focusing on outcomes, not features, and making room for uncertainty. That’s a feature, not a bug.
But I’ve seen outcome roadmaps misused and misunderstood more and more frequently as they become best practice for product-led companies. Why?Maybe it’s because they require comfort with ambiguity. Maybe it’s their simplicity that makes them easy to misuse. Either way, the underlying problem is often the same: not understanding what a roadmap is really for.
Whatever the reason, the foundational concepts behind any roadmap are the same. When you understand them it gets easier to develop your own heuristics and learn how to use uncertainty to your advantage.
Concept first, structure second
A roadmap should instantly orient the reader: where are you now, and where are you trying to go? Outcome roadmaps tell the story of problems to solve. Feature roadmaps tell the story of what will be built. Both can work but the clarity comes from intent.
💡 A feature roadmap might say: "Drive 1,000 miles in one day." An outcome roadmap says: "Enjoy the journey—and still arrive on time."
To get that framing right, I like using a metaphor: the road trip. What’s the minimum you need to map out a road trip? Not much.
1. Destination (Where are you headed?)
New York to attend a friend’s wedding
2. Travel Plan (How are you getting there?)
Drive my car, starting in Texas
3. Progress Indicators (How will you know you’re on track?)
Travel Northwest and split up the drive over 3 days
Translate that into product:
Destination = your product goal or objective
Travel Plan = outcomes and strategies you’ll follow
Progress Indicators = milestones and success measures
With that concept in mind, the roadmap is your vehicle to share the journey. Not every turn, just the direction, intent, and meaningful checkpoints. You don’t need to explain every detour.
Use uncertainty to tell your story
Outcome roadmaps don’t always tell a full story. They do a good job showing intended direction and prioritization but not as much when it comes to communicating unexpected blockers or deviations. That’s where chaos creeps in.
Here are two common missteps I’ve seen:
Turning outcome columns into time boxes. Naming your columns "30/60/90 days" or "Q1/Q2/Q3" invites people to treat your roadmap like a deadline calendar. Now/Next/Later is meant to show incrementality, not time pressure.
Writing features instead of outcomes. Something like “Implement analytics database” doesn’t describe an outcome—it’s just work. What’s the why? How does it improve user experience or business health? If you can’t answer that, it doesn’t belong on an outcome roadmap.
⛈️ When features replace outcomes, there’s a hidden assumption: once the feature ships, the value is delivered. That’s rarely true.
Milestones and Markers: A Complement to Outcome Roadmaps
To share progress more clearly without resorting to time-based deadlines, I like using an approach I call Milestones and Markers. It gives stakeholders a better sense of progress by tying completed work to measurable movement—without promising false certainty.
1. Start with the destination
Just like a road trip, clarity begins with a clear destination. On a chart, I usually make time the X-axis and value or distance to goal the Y-axis.
Example: We’re driving from Texas to New York for a wedding in 3 days.
Our goal / destination is to be in New York in 3 days to attend a friend’s wedding
2. Plot your milestones
Milestones are checkpoints on your journey. Each one is a clear, measurable step closer to your destination.
To drive 1,800 miles in 3 days, our milestones might be:
To get to New York we need to travel almost 1,800 miles. We will split up the driving time into 3 days and aim to stay overnight in Nashville, TN and Blue Ridge, VA, covering the most ground Day 1.
Milestones
1️⃣ Get to Nashville, TN (~850 miles)
2️⃣ Get to Blue Ridge, VA (~450 miles)
3️⃣ Arrive in New York (~450 miles)
We also set 🟢 progress markers to hit along the way.
If we miss the timeframe we intended for our progress marker, we have not failed, but we do need to adjust the rest of the trip to make up for it.
🔍 Tip: Miles driven don’t always correlate directly to value—just like high velocity doesn’t always mean high impact.
3. Track directional progress
In product, use output metrics (like features released or points delivered) to track effort over time. Just remember: effort isn’t always a proxy for value. Sometimes, the line plateaus. Sometimes, you move fast but in the wrong direction.
Driving 1,000 miles west when you're supposed to go east? That’s a problem, even if the numbers look great.
Pick a metric that aligns with your work cadence, and start plotting. Once the habit is in place, you can evolve it.
You might decide to add a separate line or even discard the effort line entirely once you get the hang of it. The important thing is to create a habit of measurement and hold yourself accountable to it. This is why success metrics are so crucial to an outcome-mindset: until you measure that your work produces the expected outcome, it’s not done!
When you finish work that is useful the plotted progress line will be more vertical. Logically, you are moving closer to the next milestone by delivering measurable value. Sometimes your efforts will not pay off and in those cases the line will be more of a plateau.
In this example there is a 1:1 relationship between our output (distance traveled) and outcome (New York) and having the right milestones will keep us driving those miles in the right direction.
On the road to New York we are tracking our effort using miles driven, and will plot it on an hourly basis.
This illustrates why directional measurement against your progress markers is important. You need measurement to tell you that you are directionally closer to your destination. If we drove 1000 miles west our miles driven would be through the roof, but New York would be even farther away!
4. Share along the way
Don’t wait for perfect milestones to communicate progress. With a milestones and markers habit in place, it’s easy to provide updates that are grounded in direction and context.
Road trip journal
Day 1: 😡 Left early, hit traffic near Dallas. Made it to Nashville late.
Day 2: 😢 Car trouble. 📞 Called ahead to adjust expectations. Still made it to Blue Ridge by dinner.
Day 3: Clear skies. Called again—"We’re going to make it."
This is how communication should work. Stakeholders don’t need to hear, “We shipped 5 features today.” They want to know: “Are we going to make the wedding?”
Why I Like Milestones & Markers
Milestones & Markers help my teams show real progress, grounded in value, not vanity metrics. It complements outcome roadmaps by making uncertainty easier to navigate and momentum easier to explain.
Here’s the flow:
Start with the destination and where you are now
Use outcomes to define your milestones
Track progress and share frequently
Stakeholders see how far you’ve come, how close you are to your goal, and whether you’re trending in the right direction. It reinforces the Build → Measure → Learn loop. And most importantly, it helps everyone treat uncertainty as a natural part of the process not a failure mode.
If you take away anything from this, hopefully it’s how to think about roadmap concepts in a different way. If you’d like to try it out, here’s a template in Google Sheets to start from. If it work works, great! But it might not. Every team works a little differently and nothing is guaranteed to be a perfect fit.