How to Write Your First Strategic Roadmap (Part 3)

The importance of a strategic roadmap goes beyond executing on it. Learn how your roadmap can serve you in various ways after it is ready.
Image by Arek Socha from Pixabay

“I don’t believe how much energy needs to go into explaining the roadmap to others”.

That’s what B., the VP Product of an Ed(ucation)Tech startup I’m working with, told me this week. It was after he completed preparing the roadmap according to the guidelines in part 2 of this guide, and I guided him to do what you are going to read next. He was surprised at first, but after he followed my recommendations, he realized how important it was.

Intuitively, you might be thinking that the goal of the roadmap is to define what to do so that the development team can actually do it. Of course you need to do that – bring it down to earth and get the execution going. It’s so obvious that I’m not going to talk about it further. But in part 1 of this guide, we established that the roadmap is a strategic document, and also a tool that you can (and need to) use to communicate clearly and create alignment.

Creating Company-Wide Alignment

The strategic thinking part was handled during the process of creating the roadmap. If you worked according to the process I suggested, you also started creating alignment along the way – alignment on goals, priorities and the suggested path to achieve them – with the company management.

In the next phase, you want to create alignment with the entire company (or group if your company has more than one product).

Set time with each department and present the roadmap to them. You want to include all the explanations about how you are thinking about it, why some things are more important than others and generally reflect the thought process that you were following to get to the roadmap. It is much more important than the bottom line of what you are going to do when.

Leave some time for Q&A, and make sure they get it. If your company or group is small enough you can do it with everyone together, but I would recommend no more than 30 people at once so that you can keep the discussion open.

Your goal in creating alignment is that if you ask anyone in the company what you are doing and why they will tell the same story. The only way to get there is to make sure they understand the bigger picture, including all the considerations which led you to decide on a specific roadmap.

Specifically, with your development team, the wider the context they get the better their deliverables will be. By sharing how you think with them, not only will you get better features, they will also be much more independent and will be able to suggest their own solutions to the problems you are raising.

It can help shift the entire conversation from talking about solutions to talking about the problems you want to solve – which is the right balance for the product/dev relationship.

Ongoing Alignment

There is almost no limit to how many times you need to tell the story of your roadmap. It won’t always be as a full-blown roadmap presentation, but the essence of it, the thinking behind it, and the decisions that were made during the process need to be repeated time and again.

The roadmap is both a compass and an anchor, and whenever you are talking about what needs to be done you need to start with why and where it falls in the bigger picture. Luckily, you have your roadmap to rely on. If you did the alignment process once, linking back to it should be easy.

I want to say it very clearly: you simply cannot over-communicate it. That is, no matter how many times you will be repeating this, it is never too many. People need these ongoing reminders for focus and clarity, and they will often hear something new even though you said the same things.


Your roadmap is as solid as your weakest assumption. During the process of building the roadmap, you made some assumptions. The process requires that you will make them knowingly and distinguish them from facts. And while they all have to make sense on paper, to increase the confidence in each assumption you need to validate them.

The best validation is to run 2 years forward and see that the path you selected actually worked out for you. Unfortunately, that’s not going to help you make better decisions today. The next best thing is talking to customers, prospects, industry analysts, investors, and anyone relevant to your market to get their feedback.

Use the roadmap as an excuse to talk to all of these people.

The best validation is not presenting the roadmap and hearing their feedback. The best validation is to ask them the questions that you want answers for and get their point of view. So my recommendation is to start with an open discussion and only then present the roadmap, ideally showing how the roadmap actually answers all the concerns that were raised during the first part of the conversation.

Specifically with customers, take the opportunity to learn more about their world, not only in relation to your product. I always like starting the conversation with “what keeps you up at night?”.

Make sure you frame it first and explain that we met to discuss the roadmap, but in order for you to present them with the parts that are most relevant for them and for the discussion to be more productive, you want to learn more about their world first. People love talking about themselves, from my experience most of them cooperate and are happy to give you a deeper look into their world and point of view. This is priceless, regardless of the roadmap discussion itself.

When you then get to present the roadmap, tie it back to the discussion you just had. For example, when presenting what you believe is the main pain point, tie it back to something they said which might indicate they have the same pain. Let them help you make it more accurate and relevant for them. Listen to the specific words they use. The marketing team will love you forever for this.

External Communication

The strategic part of the roadmap should lay the foundation of your product’s positioning and messaging. Work with marketing or product marketing to clarify this part and make sure it is useful for them.

The plan itself can also be communicated externally, but do it with caution. Since it is a tentative plan, you should always caveat that this is not a commitment and that it might change. I used to have a slide stating that very clearly at the beginning of each roadmap presentation I prepared.

Still, you can use themes from the roadmap to tell the world how innovative you are, or how attentive you are to your customers. It can be done informally during sales conversations, or more formally by presenting that highlights of your roadmap externally or even including some of the plans on the company’s website.

Decision Making

Life will throw at you many surprises. You will constantly need to consider and update your priorities and plans. The strategic roadmap is not the plan to stick to, but rather the fundamental guidelines and principles that you need to follow.

When new ideas or needs are coming at you, use the assumptions that lie in the basis of the roadmap as a decision-making framework. Ask yourself if this new idea is in accordance with your assumptions and guidelines. If it is not, ask yourself what has changed. Maybe you learned something new or need to add something you didn’t take into consideration. Maybe one of your assumptions turned out to be not 100% accurate and requires tuning.

If nothing changed, if everything you said is still valid, and what you are now considering is not in line with your fundamental assumptions – most likely you don’t need to do it. Reflect it and explain it this way to reach a smoother decision-making process.

When doing so, you should also consider the actual plan: anything you add to the plan will mean something else will not be done (assuming you don’t get additional resources). Use the roadmap to understand the impact and the trade-offs. Some of them are worth making, while others aren’t.

You can use the roadmap both as a decision-making framework and a communication tool around specific decisions to be made. Use the alignment and agreement you already got as the baseline to start from, and consider the changes against it.

Revisit and Refine

The roadmap is a dynamic document. When you learn something new, add it – even as a comment.

Once a quarter, see what changed – what you learned and what you accomplished – and read it again. Check if you still agree with it, if your assumptions are still valid and if the new pieces of information are still connected well to the bigger picture you were painting.

Also, consider how fast you were able to move along the path you outlined in the roadmap (AKA execution). Many times, you would be moving slower than expected. Ask yourself how problematic this is. If your reasoning is solid, the answer shouldn’t be difficult to know.

Update your roadmap accordingly.

Once a year, re-open everything. Repeat the process from scratch to make sure you are seeing your situation with fresh eyes. A year in tech life is so significant, that in most cases you will find yourself with an upgraded vision and a whole new view of the market and the challenges ahead. This cannot be achieved by micro-changes on last year’s roadmap, you need to do the full process again, and don’t worry about getting to a similar result.

When you communicate the new roadmap, make sure to explain what has changed that has led you to this new, potentially unrelated roadmap.

To sum this part of the guide and the guide as a whole: creating a strategic roadmap is one of the most important things you can do for your company. It requires effort, but the process itself creates miracles. Don’t limit the impact to be focused only on execution. You worked so hard to create a good roadmap, let it work for you and help you long after you are done.

Good luck!

My free e-book “Speed-Up the Journey to Product-Market Fit” — an executive’s guide to strategic product management is waiting for you

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