Rooster

Estimating large, future roadmap items can feel like trying to predict the weather next month—there’s just so much uncertainty. The bigger the item, the harder it is to figure out how much effort it will take. And when the item itself is still pretty fuzzy—maybe the scope isn’t fully defined—estimating becomes even trickier. What’s more, estimates usually come from the development team, which can make the conversation feel one-sided and, let’s be honest, sometimes uncomfortable.

But what if we flipped the script? That’s where “Betting on Your Roadmap” comes in. Instead of just estimating the size of a task, this approach lets you, as the Product Owner, place a “bet” on how much you’re willing to invest in a feature. It’s not just about size; it’s about cost. This approach restores the Product Owner’s role in setting priorities and constraints while also sparking fresh, collaborative discussions with the team. When you place a bet, you’re saying, “Here’s what I’m willinzg to spend—what can we build with that?” This not only shifts the dynamic but also ensures you’re taking responsibility for investment decisions in a way that engages the whole team.

Picking Your Currency: What Are You Betting?

Choosing the right currency for your bets is crucial because it sets the stage for how you’ll prioritize and discuss roadmap items with your team and stakeholders. Here are a few options to consider:

• Story Points: You can “buy” features based on the story points you’re willing to allocate. This works well if your team is already familiar with story points for estimation. It’s a way to quantify your bets in a way that feels familiar and easy to understand.
• Actual ‘Dollars/Euros’: This approach is particularly useful if your team works closely with finance. It ties features directly to the budget, making the investment crystal clear—how much actual money are you willing to spend to get this feature built?

But let me share my go-to approach, which I’ve found particularly effective in practice, especially in a multi-team Scrum environment: “1 sprint for 1 team.” Think of this as the $1 bill of your betting currency—simple, straightforward, and easy for everyone to grasp.

In this method, “1 sprint for 1 team” doesn’t mean the team will spend an entire sprint solely on one item. Instead, it means the sprint goal is focused on delivering a piece of that larger roadmap item. The key question becomes: “Can we deliver something valuable if one team focuses on this for X sprints?”

This approach not only sets a clear time frame for the investment but also takes into account the team’s context, leaving room for other work. It’s an accessible way to communicate effort and expectations, turning complex prioritization discussions into clear, actionable plans. By using “1 sprint for 1 team” as your baseline currency, you simplify the conversation, making it easier for everyone to understand the scope and make informed decisions.

Prioritization Made Easy

One of the best things about betting on your roadmap is that it transforms prioritization into a clear, meaningful conversation that everyone can get behind. For instance, if you’re using the “1 sprint for 1 team” currency, you can ask a stakeholder, “Is it worth spending X sprints on this item, knowing it will delay other features?” This type of discussion can uncover real insights—maybe the stakeholder realizes they’re okay with fewer sprints, or perhaps they come to see that the item isn’t as high a priority as they initially thought. The team can then weigh in on what’s feasible within those constraints, ensuring everyone is aligned.

In my experience, these discussions are most effective when you have both stakeholders and the team present at the same time. This way, decisions are made with full context, and the conversation is far more collaborative. Having everyone in the room ensures that the prioritization process is balanced, that all voices are heard, and that you end up with better outcomes.

Balancing Investment with Speed

Remember, the goal isn’t to spend multiple sprints working on something without delivering value. The bet is a high-level way to talk about future items without getting bogged down in too many details too early. It provides just enough structure to have meaningful discussions while still aiming to deliver value as quickly as possible. This approach helps you keep the bigger picture in mind while focusing on incremental progress.

Stay Accountable with Your Bets

Bets also help keep you and your team accountable. Let’s say you bet 4 sprints on a roadmap item. You’ve broken it down into smaller steps but expect it to take about 4 sprints to finish. After 2 sprints, you can check in: Are we on track? Is this investment paying off? If you hit the 4-sprint mark and aren’t done, it’s time to talk with stakeholders about whether to keep going. This ongoing reflection ensures you’re making smart decisions with your time and resources, adapting as needed, and maintaining alignment with your stakeholders.

From Roadmap to Backlog

The roadmap is a high-level strategic plan outlining the product’s long-term goals and vision, focusing on what you want to achieve and why over time. The backlog is a detailed, tactical list of tasks and user stories needed to execute the roadmap, turning strategy into actionable work items for the team.

Bets on the roadmap serve as constraints that guide the prioritization and scope of the backlog. As you break down roadmap items into backlog tasks, these bets help ensure that the team’s efforts align with the strategic vision. You can then use other estimation techniques to verify if the planned work fits within the constraints set by your bet, ensuring that your execution stays on track and within the agreed investment.

Conclusion

Betting on your roadmap is a powerful way to get everyone involved and ensure that you’re focusing on what truly matters. By shifting the conversation from size to cost, and using a currency that everyone understands, you can have more productive and insightful discussions about your priorities. Plus, it keeps you accountable and helps ensure that every sprint is delivering maximum value. I’ve seen firsthand how this approach can transform the way teams work together. Give it a try—you might find it’s the game-changer your team needs.

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In the next article, I’ll show you how to enhance collaboration and transparency with the World Café technique. This approach brings together your team and stakeholders in a more dynamic, interactive way to discuss the roadmap, helping you gather diverse insights and foster a sense of shared ownership.