If You’re Hitting All the Dates on Your Roadmap, You’re Doing It Wrong

Annie Dunham
Former VP of Product Management at ProductPlan

Hitting Roadmapping Dates | ProductPlan

Imagine a product team out for dinner and drinks. They’re celebrating a big win. The product manager, development team, product owner, maybe even a couple of company executives are there. They must have achieved something significant, right? A revenue milestone? Important roadmap deadlines? Reaching a target number of customers? A positive product review in a major industry publication?

What if I told you the team is celebrating the fact that they released the new version of their product a day before the internal deadline on their roadmap? That might be cause for celebration. But maybe not. Pushing out a new feature or product—even if you do it on time—is only one way to measure team success. And it isn’t the best way, not by a long shot.

Before this hypothetical product team starts raising their glasses and making toasts, they might want to wait for the answer to a far more important question. Will our customers be enthusiastic about this new product release?

Themes—Not Dates—Are the Stars of Your Roadmap

A product roadmap conveys the strategic direction and goals of your product. I like to think of a roadmap as a brief, clear story of how and why a product will impact the market.

That’s why you want to arrange your roadmaps into themes—those big-picture goals your team sets out to achieve. You want your team to focus first on product strategy, not deadlines. When stakeholders view the roadmap, you want them to easily grasp the story behind your planned work in the coming months. For a B2B software maker, those themes might look like these:

That tells a story. It depicts a company that’s thinking strategically. The themes on this roadmap show the product team is trying to find new ways to reach customers, doing business with them more conveniently, and reposition their product to find new markets.

But what if, instead of themes and strategies, the most prominent elements of your roadmap were dates and timeframes? Imagine if what stood out on your roadmap were these:

Where’s the story behind this roadmap? Where’s the vision, strategic thinking? What is this company even building? Your product roadmap should be a strategic guide, not a calendar.

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The deadlines won’t matter in the long run.

To put this another way, let’s say Microsoft adds a feature to its Teams collaboration app. Unfortunately, the new tool falls flat with users.

Now imagine that the product team launched this new feature by the internal deadline they set for themselves. In a year, is anyone in the company going to say, “Well, that Teams widget was a disappointment, but at least our product team released it on time”?

Yes, Dates Are Important to Product Success

At this point, you might be wondering if I put much value at all on dates and deadlines. Absolutely. Product managers always have limited resources—including time.

You’ll need dates and deadlines for several strategic reasons, including:

So Why Shouldn’t We Hit All Roadmap Deadlines?

If you can achieve everything you want strategically for your product and still meet every deadline on your roadmap, you might be ready to think bigger.  Empowered product management teams are constantly adjusting course to meet their customers’ evolving needs and the market.

A product roadmap should be somewhat aspirational. Its themes should include at least some stretch goals that may not be clearly defined and require creativity and lateral thinking.  Creating a roadmap with space for learning and insights means you will be ready to take advantage of new opportunities.  It also means you can regularly question if your original roadmap delivers the most value to your customer.

This is why I’m skeptical about any team’s ability to set those big strategic goals for their product but still get all of their projects done on time.

And if you have to choose between these two competing goals—aiming big with your product or hitting all of your roadmap deadlines—I’d highly recommend you choose to aim big.

A Deadline Culture Has Nasty Side Effects

Becoming date-focused on your product roadmap is dangerous not only because it can take your team’s attention away from the strategy they should be focusing on. The risks are much greater than that.

Here are some of the negative side effects of prioritizing roadmap deadlines over themes:

1.  Focusing on deadlines assumes you have nothing to learn.

When planning your roadmap, you have a good idea of the problems you are looking to solve, whether framed as jobs to be done, business objectives, or even features. You likely have some hypotheses about how you will solve them and even the technical challenges, but you should be prepared to learn along the way. Reserve space for additional validation and discovery, and be open to learning that you need to make some changes. You may find the problem isn’t worth solving or that it’s no longer the highest priority due to market trends. Alternatively, you may find that to solve it well, and you need to do much more than you planned.  If you are focused only on meeting the deadline, you are not delivering the best solution possible.

2. You might set deadlines later than necessary to make sure you hit them.

In a company culture that treats deadlines as its prized metric, product managers will undoubtedly be tempted to set their roadmap deadlines out as far as possible. What better way to ensure “success,” as the company defines it?

But when you take this approach, you also under-use your developers, product owners, project managers, and other team members. You might not be allowing your team to function at top capacity and do all the great work they’re capable of.

3. You might aim too low because you’re afraid of upsetting stakeholders.

A date-obsessed product team also runs the risk of playing it safe, under-promising, to hit their deadlines. This often happens in organizations whose executives focus on deadlines over other success metrics.

But your senior leadership’s obsession with roadmap deadlines can’t be your excuse to limit your strategic goals or vision. As a product manager, it is your responsibility to show your executive stakeholders that you have big goals for your product. You’ll need to persuade them that achieving those goals will be more important than whether you hit your roadmap’s deadlines.

4. You might prioritize work, not for its strategic value but because it seems easiest to complete on time.

And what an innovative and impactful product that will be!

Failure can be a powerful teacher. If you set aggressive deadlines for a project and miss it, that can still yield some successes. For example, it can help you discover important details about your team’s capacity and pacing and any shortcomings of your processes.

But even more important, building a culture that allows for a degree of failure—such as missed deadlines—also encourages more innovation and risk-taking. Both are keys to building products that make a positive impact on your market.

How to Deal with Roadmap Deadlines

Having said all of this, I do believe deadlines can play a useful role in your product roadmap. After all, I’ve overseen the development of the date-based milestone feature on ProductPlan’s roadmap app.

But you need to make sure your team treats roadmap deadlines with the proper amount of weight. Your team shouldn’t ignore the deadlines on your roadmap, nor should they think their success rests on meeting those dates.

Here are a few steps I’d recommend:

  1. Build a team culture that emphasizes product quality first (even above deadlines).
  2. Set a success rate for hitting deadlines that you’ll be happy with. It should be a high percentage but below 100%.
  3. When your team fails to hit a roadmap deadline, please don’t treat it as a reason to reprimand your coworkers or to hang your head in shame. Instead, learn from those misses.

As a Product Manager, Your Real Goal Isn’t on Any Calendar

As you drive your products’ development and continuous improvement, you’ll want to hit your deadlines whenever you can. That’s one way to measure how effective you are in your product management role.

But it’s not the end in and of itself. The goal behind any product management effort—releasing a new feature, for example—is to benefit both your customers and your company.

Remember: Your primary role as a product manager is to solve real problems for your market. It’s not to deliver those solutions on June 11.

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