A CPO’s Guide to Choosing the Right “Roadmap” Tool

Ryan Polk's CPO Series Quote

The tech stack of your product team can make or break the effectiveness of a product organization.

Ryan Polk, Chief Product Officer (CPO) of Stack Overflow, recently shared his insights during a CPO Series webinar focused on choosing the right “roadmap” tool – or rather the right product portfolio tool for him and his product organization.

The Selection Process: A Case Study from Stack Overflow

At Stack Overflow, Ryan’s team chose Dragonboat because they need a platform that enables the complete product operating model, including both product roadmapping and strategy formulation, execution, and investment optimization. A platform that enables product managers, product executives, business leaders, and overall participants in building products that deliver customer value and business outcomes.

There are 4 things your “roadmap” tool should enable you to do:

1. Keep your strategy visible by linking roadmaps directly to outcomes

Ryan stepped into a Stack Overflow that had seen a lot of changes and challenges, including a significant disruption by AI technology and a 9-month gap without a CPO. The previous systems had deteriorated in the absence of leadership.

Ryan’s first order of business was to reintegrate and realign these systems. His key advice is to ensure there’s a basic structure connecting every layer of your organization, from top to bottom.

Product organizations should use tools that help create a direct, understandable link between what your teams are doing and the outcomes you aim for. A great tool like Dragonboat can help keep your strategy in the spotlight, preventing it from getting diluted or lost.

the right roadmap tool: Portfolio Roadmaps Module shows all work linked to outcomes
Dragonboat View that Ryan uses daily: Portfolio Roadmaps Module shows all work linked to outcomes

With Dragonboat, Ryan was able to see all his roadmap items linked to outcomes. The platform enables visibility into the strategic layers: Objectives at the top, followed by Initiatives and then features. Seeing the associated quarter and progress of each objective and work item helps Ryan and his team have an instant view of all work across the product organization.

2. Create visibility into roadmap commitments

Often, roadmap commitments are nebulous, with many dependencies between teams not immediately apparent. Ryan advises making commitments and dependencies clear to everyone.
His approach involves consolidating or “rolling up” commitments on a quarterly basis. By the quarter’s end, Ryan evaluates the team’s say/do ratio: how many commitments were planned versus what has been accomplished.

the right roadmap tool - Dragonboat’s Delivery Dashboard
Dragonboat’s Delivery Dashboard enables CPOs to check into their delivery commitments in real-time

On a regular basis, Ryan looks into his Dragonboat views to identify bottlenecks or tasks that are veering off course. For Ryan, successfully pausing or removing an item that is not on track from the roadmap is considered a victory. It frees up resources for the rest of the team, enhancing the overall product ROI significantly.

3. Simplify allocation and trade-offs

At Stack Overflow, Ryan noticed that shifting resources and work between departments created many logistical difficulties. It was hard to gauge capacity or understand where trade-offs were happening. Ryan’s advice is to establish consistent, persistent teams. Then, with systems like Dragonboat, you can allocate work based on strategic priorities, simplifying the process of making those tough decisions.

“What you need [as a CPO] are high-level tools to make trade-offs, to be able to deep dive into what you’re working on on a daily basis, and manage that.”

– Ryan Polk, CPO of Stack Overflow

Ryan recommends having a clear understanding of your R&D organization’s focus areas, and where the bulk of your budget is being allocated. He advises all CPOs to create a report similar to what he uses in Dragonboat: categorizing the nature of the work being undertaken (e.g. maintenance, architecture, tech debt) and running allocation reports.

Dragonboat's Allocation Report
Dragonboat’s Allocation Report gives a real-time view into trade-off decisions by categorizing the current work and comparing it to various product dimensions (e.g. outcomes, themes, etc.)

This approach enables you to weigh the potential benefits of the features you’re rolling out against the capacity allocated to each category. Having a firm handle on this information is essential for justifying your expenditure decisions, which often are not the exciting innovative features the company is excited about. This tool aids CPOs in communicating and defending these choices to other members of the executive team and the rest of the organization.

4. Measure both outcome and roadmap progress

For Ryan, gaining visibility was the first critical step toward accurately measuring and reacting to product performance. For Stack Overflow, Dragonboat brought visibility, which empowered the team to track performance, and adapt as necessary.

The CPO must ensure everyone in the company is aligned with the company’s strategic priorities: what the company’s goals are, the goal progress, everyone is focused on achieving them. In executive meetings, CPOs must articulate the new deliveries, the value creation behind them and help the other teams create the GTM motions post-delivery.

Dragonboat's Outcome Module
Dragonboat’s Outcome Module allows executive team updates to stay high-level

To do this, Ryan uses Dragonboat’s executive dashboards to present high-level strategic updates. The dashboards provide visuals of where the company’s priorities are. This helps the executive team grasp and manipulate key information without getting bogged down in granular development details.

Leadership Tips for Effective Tool Adoption

After you have made a selection, you need a swift adoption process to maximize the tool’s benefits. Ryan shares a few recommendations for implementing a tool as the new CPO:

Don’t put off tooling

Bringing in templates and spreadsheets might fix a few problems, but it also means you’re leaning on a quick fix that can make it tough to switch tools later on. If you get the right tool sorted out as soon as you start, it shortens your learning cycle and quickly sets you up as a leader within the organization, guiding the executive team towards the right decisions.

Prioritize ease of use and support

A tool’s complexity shouldn’t be a barrier to adoption. Opt for platforms known for their comprehensive support, and intuitive design. This will shorten the learning curve, enabling your team to capitalize on the tool’s benefits sooner.

“The support from the Dragonboat team was top-notch and gave us the ability to evolve our processes.”

– Ryan Polk, CPO of Stack Overflow

Engage with your provider

Ryan recommends leaning on the expertise and support of your tool’s provider for a smoother integration of the technology into your workflows. Their insights can help tailor the tool to your specific needs, maximizing its effectiveness.

“Don’t underestimate the power of your provider to help you get going as an accelerator, especially when you’re a new CPO.”

– Ryan Polk, CPO of Stack Overflow

Seek comprehensive solutions

A holistic tool that encompasses all aspects of planning—from strategy alignment to quarterly planning and executive communication—ensures a unified approach to product management. Such integration is key to maintaining strategic coherence across different levels of the organization.

Future of Roadmapping Tools

Ryan sees an interesting trajectory for roadmapping tools, leaning significantly towards emphasis on Return on Investment (ROI). These tools will go beyond tracking, proving tangible ROI for each feature and strategy, integrating deeper with analytics, offering real-time insights into feature performance, and tying initiatives to the organization’s financial health.

In times of volatility, it is necessary for teams to focus on ROI to sustain value. Advanced product tools will play a crucial role in stabilizing and advancing product development entities.

Dragonboat’s product portfolio management platform is specifically designed to tackle the challenges Ryan is up against as a CPO of a modern product organization. For those interested in seeing how Dragonboat can directly support the implementation of these practices, we invite you to join our next group demo. 

Don’t miss out – Secure your spot for our next group demo, led by Dragonboat’s CEO Becky Flint.

Ready to accelerate product outcomes?

Alisa Vaz

With over a decade in global product teams across Canada, China, Spain, Germany, Switzerland, and the USA, Alisa is a seasoned Product Manager with a passion for crafting tools to elevate product organizations. As a Senior Product Manager at Dragonboat, she is committed to empowering product leaders to drive business results.
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