Proof Over Opinion: 8 Strategies for Selling a Roadmap to a Skeptic

Here you are up to your eyeballs, creating a killer product strategy and roadmap. Only, you discover that a key stakeholder doesn’t agree with your approach. With heels stubbornly dug in, the stakeholder’s opposition threatens to stall development—all that incredibly positive enthusiasm and momentum that’s been building fizzles in an instant.

If this sounds familiar, you’re not alone. Unfortunately, this is a widespread scenario in product management.

A roadmap skeptic poses a two-fold dilemma for a product manager (PM): you have to keep product development moving forward while figuring out how to sell your roadmap to the skeptic.

Addressing Roadmap Skepticism

By definition, a skeptic holds deep doubt about the truth of a particular thing. Because the underlying uncertainty can be deeply entrenched, a skeptic’s opinion about a specific aspect of your roadmap or strategy can give way to strong emotions, and discussions can grow heated fast. And once that happens, any openness to learning, flexibility, or even consideration of a different perspective fly out the window.

Don’t be fooled, however. Skepticism isn’t simply a contradictory opinion. At its core, skepticism often has more to do with an aversion to uncertainty than a strategically formed opinion about something. For some, uncertainty is a scary state of mind–particularly for those of us who have a greater need to be in control. So as you endeavor to win over a skeptic, remember to be gracious and empathetic as you argue your point of view. Look for ways to soothe your skeptic’s fear of uncertainty and need for control, or at least be mindful that the underlying resistance might be more about the skeptic and less about you and your roadmap.

Read Jim Semick’s tips for embracing uncertainty.

According to Peter Boghossian, professor of philosophy at Portland State University, changing the mind of a skeptic starts by asking a simple question:

“…asking the question, ‘What evidence would it take to change your mind?’ creates openings or spaces in someone’s belief where they challenge themselves to reflect upon whether or not their confidence in a belief is justified. You’re not telling them anything. You’re simply asking questions. And every time you ask, it’s another opportunity for people to reevaluate and revise their beliefs.”

8 ways to sell your roadmap to a skeptic and win them over

If you find yourself in a showdown with a skeptic about your roadmap or product strategy, you’ve got to get strategic about winning them over to your point of view. Keep in mind that you’ll have better luck sharing proof rather than opinion, evidence rather than conjecture, and outcomes rather than hunches.

1. Arm yourself with data

First and foremost, forgo your opinion. While a skeptic may be making a decision based purely on opinion, you should leave your own opinion out of the debate. Converting a roadmap skeptic into a roadmap believer will take nothing less than solid proof in the form of hard data. If you don’t deliver the data, you’re not going to change anyone’s mind.

Read the Strategic Roadmap Planning Guide ➜

2. Deliver data in two flavors

Gather both quantitative and qualitative data. As a PM, you’ve done your homework when it comes to understanding the customer’s perspective. You know what their wants and needs are. Your goal is to align that knowledge with a product outcome that will delight them and keep them coming back.

Dig into your wealth of customer knowledge to harvest compelling customer stories to share with your roadmap skeptic. Revisit the notes you took during conversations with customers that initially helped you distill their pain or unique perspective. If you can find audio recordings that deliver your point of view through the customer’s voice, share a few snippets. It’s impossible to argue against the opinion or first-hand experience of a customer. And it’s these very interactions with customers that helped shape your strategy and inform your roadmap.

You might even invite a few key customers into a live conversation to share their perspectives. Let your roadmap skeptic listen in, and see if hearing directly from customers has a greater impact on dispelling the doubt.

Read 10 Great Questions PMs Should Ask Customers

3. Talk like a negotiator

A roadmap is always a compromise. Even though you feel passionately invested in your product, try to leave emotions out of the discussion. Lean towards being rational. If your skeptic doesn’t think you should be doing X, ask their opinion which initiative to drop from the roadmap.

4. Align with company goals

An effective roadmap will always align firmly with the overall goals of a company, like profitability objectives, customer service, operations efficiency, or growth of the business. If you intentionally tie every roadmap initiative back to your primary company goals, it’s far less likely that you’ll have to sell or defend your roadmap to a skeptic in the first place. Even the biggest skeptic would have a hard time arguing against company goals.

Company leaders and product managers alike can benefit from the SMART goal setting framework to establish clear, attainable goals and increase the odds of successfully achieving desired results.Steps to using the SMART framework to create, develop, and achieve a clear, meaningful goal.


5. Keep surprises out of the equation

Nobody likes a surprise in product management–especially stakeholders. If you involve key stakeholders early in the development process, you’ll be more likely to avoid unwelcome surprises further down the road when it’s too late (or too costly) to change course.

Here are 6 reasons product roadmaps fail.

An effective product roadmap plays a central role in communicating the strategic vision and objectives of a product, keeping a product team on track, and managing stakeholder expectations. To be effective, however, a roadmap needs to accomplish several strategically important tasks simultaneously, including (but not limited to):

  • Clearly communicating the product’s strategy and vision
  • Helping the product owner earn stakeholder approval to proceed with the development
  • Ensuring all teams involved understand and are working toward the strategic goal
  • Serving as a helpful guide throughout the process that product managers, developers, and other teams can refer to and make sure they are still on track
    Download The Product Strategy Playbook ➜

Remember, a roadmap is a living document. It must be realistic. And it should include only high-level information, not just a long list of features. To win over a skeptic, make sure your roadmap is a clean, mean, development machine.

Here’s how to create an effective roadmap.

6. Build confidence with examples

Show your skeptic how previous initiatives turned into real needle movers for the company. It will help to build confidence in the same processes and people involved in the current development initiative. Highlighting your track record of successes will also motivate and encourage those involved with the current initiative.

7. Think beyond features

Don’t fall into the trap of a features-only roadmap. Product roadmaps most often fail because PMs mistakenly assume the roadmap should be a list of the features and other details they want to include in a product. Your product roadmap should include only high-level information. This includes themes, epics, goals, possibly some user stories, and possibly timeframes—but not a long list of features. A long list of items all but guarantees that people looking at it will quickly lose focus and interest.

Try a theme-based roadmap instead.

8. Share your roadmap broadly

Don’t just communicate the roadmap to a select few. Share it more broadly within your company. Doing so unifies people by inviting them to participate in a shared goal and enables them to understand better and support the vision. It’s a powerful way to motivate groups and people across the organization–even if they aren’t directly involved with developing a product.

If you’re a PM facing a showdown, try to put these tips to use to convert a roadmap skeptic into a roadmap believer. They might even become a roadmap evangelist!

Download the Free Product Leadership Book