The Essential Questions That Lead To A Great Product Roadmap
“The question ‘Why?’ is the beginning of wisdom.” — Socrates
There is no shortage of times when the right questions bailed me out in a challenging situation, saving me from embarrassment, either by giving me more profound insight into the problem or allowing me to deflect shortcomings in my knowledge. Yet, there is one specific incident that sticks out in my mind.
It was an oddly cold winter day for the southern United States. However, it shouldn’t have mattered. I sat comfortably inside a long, wide, unfurnished conference room in what was to become an innovation hub — clearly, the team had yet to hire the decorators. For me, the emptiness was a welcome sight as I find over-the-top, ‘innovative’ design distracting.
The team bantered as usual about the project — exchanging pleasantries while giving each other crap about where they were with their deliverables. My contribution? The roadmap for a new digital product designed to support a high-risk population suffering tremendously from the burden of disease. No pressure.
As the client walked in, the ‘music’ screeched to a halt. Game on. This client was known for asking questions that were off-the-chart challenging. But I was ready. There wasn’t a question I had not prepared for. And that’s where I got myself in trouble. I got cocky.
It was my turn to present. I ran through the roadmap for the product, fielding all the questions and handling them like a pro. Then it happened. How will we get paid? Uhh, what? We are building a product for a non-profit to help people with severe chronic conditions, not to make money.
Great, it’s my time for a roasting.
Fifteen minutes of interrogation.
But this taught me an important lesson — when creating a roadmap, you must prepare to answer questions about the roadmap and the inputs and outputs that shape the roadmap.
Now, that may seem obvious. But hear me out. You don’t just need end-to-end awareness; you need to know how to ask the right questions to gather and shape the information that drives your roadmap.
And when it comes to questions, I am a hoarder. Over the years, I have accumulated an extensive, ever-growing list of questions from tough clients, executives, teams, customers, and stakeholders. While I can’t cover all of them in a brief post, I’ll share the ones that frequently surface.
Here’s another great quote to prime the pump before we dive in — it’s also one of my favorites.
“The wise man doesn’t give the right answers; he poses the right questions.” — Clause Levi-Strauss
What happens before and after your roadmap stays with your roadmap
Context is king. True for life, true for your roadmap. Understanding the context surrounding your product is critical before you work on your roadmap. Context is invaluable input.
Unfortunately, my younger self often made assumptions about the context instead of asking the right questions. I failed to do my homework. I jumped to conclusions out of convenience.
However, since the fateful roasting on a cold southern day, I’ve embraced the power of the question “WHY.”
In the wise words of Simon Sinek —
“Innovation is not born from the dream; innovation is born from the struggle. It’s born from the people who are willing to ask the question why and who are willing to challenge the status quo.”
We can all agree that one of the primary purposes of your product roadmap is to lay out your case and plan for product innovation.
My suggestion? Start with the big why questions to gather context as input to the roadmap. Questions like:
- Why are we building this?
- Why should anyone care that we are making this?
- Why do the market and our customers need this product?
- Why are we the right company and team to deliver this product?
- Repeat after me — “Why, why, why?”
You see the pattern. Getting the macro, big picture, context-setting questions out of the way first — your whys — is important before asking what, how, when, where, and for whom. Channel your inner child.
Why always comes first when developing your product roadmap.
The Five Why Samurai
Before we leave context and shift to practical questions geared toward roadmap development, I want to build on the power of why in sequence five times — the five why samurai (yes, I made that up).
The Five Why Samurai approach is quite simple: when a situation arises, you ask “Why?” five times, slicing the information down into small chunks until you reach the root cause of the issue. Each answer forms the basis of the next question.
Sakichi Toyoda, the founder of Toyota Motor Corporation, originally developed the Five Why method (minus the samurai). Toyoda used the technique to identify the root causes of problems in his factories, and he found that it was an effective way to prevent problems from recurring.
Here are the steps, simple and straightforward:
- Identify a problem, open issue, or critical context related to your product.
- Ask “Why?” five times, following up with an answer that explains the reason for the previous answer.
- Continue asking “Why?” until you reach the root.
- Once you have identified the root, capture it as critical context and input to your roadmap.
Consider this simple, representative example:
Problem: The car won’t start.
1. Why? — The battery is dead.
2. Why? — The alternator is not functioning.
3. Why? — The alternator belt snapped.
4. Why? — The alternator belt was well beyond its useful service life and was not replaced.
5. Why? — I did not maintain the car according to the recommended service schedule.
So, the root of the problem is vehicle maintenance. The solution? A reminder via in-app messaging about service. Of course, that is only one possible solution. Additional context and input should indicate if that is the right feature for your roadmap that leads to the outcome of preventing a dead battery.
Taken down a different path, you might add an alternator belt with a longer life span — especially if it’s a luxury brand.
The “Five Whys” method identifies the broader and specific contexts when road mapping. It ensures that every roadmap item is a solution and a response to a deeply understood problem.
Critical questions to ask and answer when building your roadmap
Now that we got WHY out of the way, let’s focus on additional questions to consider as you create and prioritize your roadmap. These differ from the standard product roadmap development questions focused on documenting features, epics, and stories — I assume you have those down.
Instead, product managers often need to ask a variety of strategic questions to ensure that they are developing products and capabilities that meet the highest priority user needs, align with business goals, and can be effectively marketed and sold.
A few of my favorite top-level questions include:
- Why are we doing this? You should articulate how your product or feature will solve a problem for your company, buyer, and user.
- Who are we building this for? You should be able to define your buyer and user persona, segment the market, and focus on the most valuable and reachable customer segments. This is true of a product and a feature. You need to know who it is for.
- How would we define success? Your objectives and key results tied to the feature should be clear. Success has three sides. Success for your company. Success for your buyer. Success for your user.
- What outcome(s) are we aiming for with the product, epic, feature, etc.? No outcome, no go. It shouldn’t be on the roadmap. Only spend time on discovery if there is a clear hypothesis on the outcome and value.
- Is this a pain killer or vitamin? This is a fairly common question in Silicon Valley circles. Is this going to produce short-term relief or hope for long-term gain? Focus on painkillers first.
- How are we going to make money? How will the outcome, reflected as an epic or feature on the roadmap, contribute to our ability to make money?
- What constraints do we have? Are the resource, time, market, regulatory, or other constraints we need to plan for when building the product or feature?
- What assumptions are we making/do we need to make? And how will we validate those assumptions? It’s important to identify critical assumptions you need to test as you go through discovery and build.
- Do we have any dependencies? Dependencies are relatively straightforward but often ignored.
- If you depend on someone, something, some capability, etc., validate that it will be available when needed.
- How will we validate the DMF of the product or feature? Desirability, marketability, and feasibility. Only with those in combination proceed.
- Are we sure this is a priority? It’s always good to confirm that you are still focusing on a product or feature that passes the prioritization test — is the highest value’ thing’ we can spend our time and resources on?
- Do I have the information and context I need to move forward? Are you missing anything? Do you have open questions? Only start with a clear understanding of what you are getting into.
- What’s our learning and feedback plan? Often forgotten, you need a mechanism to deal with and incorporate what you learn and the feedback you receive from users.
Bringing it home
The power of questions in product management and roadmap development is indisputable. Throughout my career, whether being caught off guard in a meeting or applying my ever-growing arsenal of questions to build a product roadmap, the significance of “why” remains a critical first step.
For every product manager, questions should be their north star, whether working on the strategy or the roadmap. And while questions are foundational, they aren’t just about gathering inputs and data. They’re about understanding, interpreting, synthesizing, and ultimately, innovating. Roadmaps become more than plans when based on the right questions.
After diving deep into the art of questioning, remember that every product begins with a set of questions, often rooted in a simple “Why?”
Socrates was right; the question ‘Why?’ truly is the beginning of wisdom. So, the next time you work on your product, pause, reflect, and ask a question.
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