6 Crucial Conversations to Have Before You Start Your Roadmap

Kirsten Schierholt

Kirsten Schierholt
Marketing Operations Analyst at ProductPlan

A carefully constructed roadmap can be a powerful tool that can align stakeholders and motivate coworkers. It can even jumpstart sales and growth.

But a neglected roadmap can prove problematic and breed internal dissent. It can also mislead customers, misallocate resources, and erode a product manager’s credibility.

Making sure a roadmap falls into the first category doesn’t happen by accident. Not only must you put in real time and effort, but you also need to cover all the bases and not take any shortcuts.

Much of this work begins before you even fire up your favorite roadmapping tool and drop a single item or theme on there. Fixing a roadmap is much harder than getting it right from the get-go.
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The process should start with crucial conversations, which aren’t always easy. These must occur to ensure this roadmap is building toward a shared vision. That means including mandatory requirements and meeting the expectations of everyone involved.

We think these six conversations are crucial to the success of any roadmap, as well as the future of your roadmapping process. These tips are applicable for newbies drawing up their very first roadmap, but they’re also valid for experienced veterans. There’s always room for improvement, but if you have these conversations before making your roadmap it will pay dividends down the line.

Six Conversations to Have Before Making a Roadmap

Giving credit where credit is due, this post was heavily influenced by the bestselling book Crucial Conversations. It’s a worthwhile read that explores the importance of having complicated dialogs as well as how to diffuse the emotions that make these conversations so tough to initiate and complete.

Too often, we avoid talking about specific topics because we predict it will be uncomfortable. Most of us don’t seek out confrontation and instead labor to keep the peace. But bypassing subjects or interactions to sidestep those situations doesn’t solve anything. It just kicks the can down the road.

In product development, those delays can prove deadly. Wait too long, and time has been wasted shipping products that create far more problems. It can exponentially increase anger and resentment. It also eliminates many opportunities for mitigation and compromise.

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In the product management role, where you dwell at the intersection of sales, engineering, customers, marketing, and management, there’s no room for conflict avoidance. Instead, product managers must sometimes stir up trouble, forcing folks to find a resolution.

These conversations may take many forms and cover a wide range of issues. But here are six types of conversations to have before making your roadmap:

1. Starting with empathy

The number one reaction to a roadmap is someone asking why things are on there. Questions usually follow this inquiry as to why something is slotted in a particular place. And, of course, why isn’t there something else on there.

These inquiries circle back to the fundamental purpose of the roadmap—why are we doing this in the first place?

For product managers laser-focused on the customer experience and well-versed in target personas, this may seem so obvious it doesn’t merit any conversation at all. But what’s a no-brainer for you isn’t the case for coworkers and stakeholders further away from the customers.

To bring along everyone else to reach the same enlightened state of customer empathy, it requires a little effort. You must encapsulate the needs, desires, and frustrations of the customer to ensure everyone is on the same page.

This conversation shouldn’t be uncomfortable or confrontational. While the facts, stats, testimonials, and requests you’re sharing may be new, the goal isn’t to attack preconceptions and argue. Instead, it’s all about building a common vision of what customers are yearning for and why.

It’s only from a common starting point and mutual understanding that a roadmap is embraced universally and supported.

2. Establishing a mutual goal

We don’t all want the same thing. Even when we do, we may not agree on how to get there. This disagreement is why it’s worth sifting through initiatives with each stakeholder to find some common ground.

Ideally, you can both center alignment around a mutual goal. These goals can be broad (“We both want to increase revenue”) or specific (“We both want to land this customer”). The important thing is finding something all parties want to happen.

To find that mutual goal, you can rely on another acronym: CRIB.

  • Commit to seeing the mutual purpose
  • Recognize the purpose behind the strategy
  • Invent a new purpose
  • Brainstorm new strategies

By agreeing to find something to agree upon, there’s an instant change in dynamics. Focusing on purpose rather than a specific strategy establishes commonalities versus highlighting differences. If the stated goals aren’t working for both sides, develop ones that do. You can then work together to figure out how to make the shared goal a reality.

After establishing a mutual goal, the conversation to have before creating a roadmap gets down to tactics and prioritization. There may still be disagreements. But you can always rally around that shared objective. There’s an understanding that you’re both trying to make it happen even if it’s not the path you would’ve chosen yourself.

3. Separating facts from fiction

While our brain might be chock full of trivia, we’re far more likely to process information as stories. Those stories contain vital facts or events. But they’re connected via a narrative constructed from inferences and assumptions.

This inference is why two people can look at the same set of facts and see two different realities (although this is different from “alternative facts”). Often, our disagreements about roadmaps stem from the stories we’ve assembled to make sense out of the facts at hand. For example:

  • Signups are up (fact)
  • Purchases are down (fact)
  • So there’s a problem with our shopping experience (story)

Metrics don’t lie (in this case). But the assumption that sales are down because customers can’t complete the transaction is only one possible scenario. Some other possible stories could explain these two facts.

There could be seasonality issues, or the store could be out of stock on in-demand items, or the pricing could be too high — many potential reasons for those two facts.

However, it’s unlikely the information was presented like the three bullets above. Instead, someone probably said, “There’s a problem in the shopping experience because purchases dropped even though signups have increased.”

Separating that narrative from the facts is another tough conversation to have before creating a roadmap. But it must happen to assess the situation and devise a path forward accurately. If everyone takes the “shopping experience problems” reasoning at face value, the company may spend tons of time “fixing” something that may or may not be broken without ever exploring other possible causes. This issue will clutter the roadmap with features and initiatives that may not do anything to reach a mutual goal.

4. Making it safe for feedback

Not every corporate culture embraces full transparency and debate. Even if yours does, not everyone may feel comfortable “rocking the boat” by asking questions or disagreeing with the status quo.

A successful product strategy requires consideration of every idea, regardless of who originated it or its possible consequences. And since the roadmap is the plan to turn strategy into reality, stakeholders, peers, and partners should be encouraged to offer up their concerns and objections.

Fostering a forum with welcomed, solicited feedback may be tricky. In order to elicit responses, you must reassure participants that:

  • You want their feedback
  • You value their opinion
  • There will be no judgment or punishment based on their feedback
  • You won’t take their feedback personally

However, creating a welcome environment is only the first step. Once folks open up, you must employ listening tools to reinforce your commitment and get them to keep sharing their thoughts and opinions.

In Crucial Conversations, the authors prescribe something known as AMPP:

  • Ask them to tell their stories
  • Mirror to confirm their feelings
  • Paraphrase to acknowledge their story
  • Prime when you’re getting nowhere

5. Creating a communication plan

Product roadmaps are seldom static. There are myriad factors that can necessitate a change or an update. And while making those tweaks and modifications is essential, they’re only half the battle. The other part is making sure everyone is aware of those adjustments and their impact.

Product managers must develop an agreed-upon framework for oversight and communication. This framework must include a few key ingredients:

  • Who must approve of the changes?
  • Who must receive information about the changes?
  • How often should changes be communicated?
  • What method(s) will you use for that communication?

For example, if you’re dropping a feature from a release, who needs to sign off? After accepting the change, who else needs to know? Should they be informed immediately or just updated on a set schedule? And is it enough to just update the online version of the roadmap, should there be an email, or does this require a meeting?

Of course, this may need to be a little more nuanced. If it’s just a schedule change and not substantive, are the same procedures required? Should some updates be restricted to internal personnel if the roadmap has been shared with customers?

This roadmap conversation also shouldn’t be particularly problematic. But it does need to happen. Without it, everyone is operating under different assumptions that may spell trouble down the line.

6. Do your homework

Having these conversations isn’t easy. Make them a little less terrible and a little more productive by first answering some crucial questions for yourself.

  • Who cares (or will care) about the roadmap?
  • Who understands the current process, or has previous roadmapping experience?
  • How many total people need to be involved in the process?
  • Who must I get buy-in from?

With those questions answered, it’s easier to whittle down the list of potential participants in the process. While everyone might have something to contribute, securing the presence and support of influential decision-makers and key idea generators is the goal.

The Upside of Tough Roadmap Conversations

The crucial conversations we covered above may not seem like much fun. The very idea of having them with coworkers might make you reconsider your life choices. But avoiding them doesn’t do anyone any favors.

Making a roadmap is a high-stakes endeavor. People can end up out of the loop, the roadmap itself can become out of date quickly, mimic a feature factory, or even end up ownerless.

Use your roadmap for its compelling intended purpose by following these conversations to have before making your roadmap.

Learn how to plan more strategically before and during your roadmap process. Read Your Guide to Product Roadmaps