How to Write Your First Strategic Roadmap (Part 2)

Now that you understand what a good strategic roadmap should include, here is the process that you should follow for building yours.
Image by Arek Socha from Pixabay

The process of building your strategic roadmap has 5 steps, as described below:

Step 1: Agree on the goals and the business context

The essence of this step is described in part 1 of the guide. You must understand where you want to go before you build the route to get there.

You need to get to an agreement before you move to the next step, so you should start the process by sitting with the CEO and discussing the definition and prioritization of goals.

To make this an effective discussion, you need to come to it prepared with a suggestion that you can review and make changes on. Don’t start it blank – you are the leader of this process, the CEO shouldn’t be the one giving you all the information. Make it a review session and frame it as such.

The best way to get to such a suggestion is to write it down. Start with what you already know or assume about the company goals (state clearly which ones are known facts and which are only assumptions). Then explain clearly – in writing – why you believe these are the right goals to tackle.

Some people view writing as merely a communication form or a knowledge sharing mechanism. But writing is a very powerful tool to organize your thoughts and sharpen your claims, way before you share them.

Jeff Bezos knows that, and that’s why he created the famous practice of writing a 6-page memo before each meeting. As explained here, the magic happens before the meeting, when the author prepares the memo:

“Full sentences are harder to write, [Bezos] says. They have verbs. The paragraphs have topic sentences. There is no way to write a six-page, narratively structured memo and not have clear thinking.”

(via Amazon’s Jeff Bezos: The ultimate disrupter – Fortune Management)

By the end of step 1, you need to have alignment on the goals, on the reasoning behind selecting those over others, and on the breakdown of the high-level company goals to more tangible product goals. Usually, this would require at least two iterations: an initial suggestion from you, review and feedback from the CEO, applying the changes and reviewing briefly again to make sure the feedback is fully understood and everyone is in agreement regarding the next steps.

In some cases, you need to do it separately for the high-level goals, agree on them, and then tackle the breakdown of goals the same way.

Generally, the strategic roadmap is built of layers that you are adding one after the other. Each layer is based on those which came earlier and extends them. That’s why it is critical that at the end of each layer you make sure you are aligned on everything you have up until now so that the next layer is built on solid ground.

Step 2: Collect as much input as you can

Which kind of input?

In the previous step, you created clarification and alignment on the company strategy. In this step, you want to learn – as freshly as possible – about the market and how your product is perceived and interacts with it.

You want to learn things like:

  • Market trends
  • Competition changes
  • Clarification on the problem you are solving and for whom
  • If you are B2B – the above applies for both the user and the buyer, who are typically two different people and two different angles of the problem
  • Alternative solutions that people are using today to solve the same problem
  • Customer’s mindset when they are using your product
  • What’s holding them back from using your product more or more often
  • Common product gaps

and so on.

From which sources?

You should seek input from everything and everyone. In this step, you want to open yourself to as much input and feedback as possible. You will have time to aggregate, organize and prioritize the input later. For now, you should focus on collecting it and keeping your mind open (more on this below).

Your sources should include:

  • Publicly available information on the above questions (you will be surprised to see how much you can learn from Googling the right questions)
  • Analyst reports
  • Support tickets
  • Your backlog
  • Customer interviews (new and past ones)
  • The point of view of as many people as possible: CEO, sales, marketing, customer success, R&D and operations (it means you need to interview at least the head of each such department), and also include board members if possible as they have their own unique view

How to make the most out of it?

You want to collect as much new information as possible, so you need to truly listen and try to absorb what you find. Don’t try to process it at this point or think about how it fits into what you already know. Simply write down what you are learning – whether you agree with it or not.

Note that listening to someone and writing down their thoughts doesn’t mean you have to implement them fully later, or even that you agree with them in the first place. Frame the conversation as information gathering, and only ask clarifying questions during the process, don’t try to convince them that they are wrong even if that’s what you think. They should be doing most of the talking, not you. Assume they have a reason for thinking about it this way, and try to find out what it is. As you do with your customers (I gave some advice about it here), try to fully understand your stakeholders and where they are coming from.

As the owner of the roadmap, you might be tempted to try and come up with the answers all by yourself. This is a mistake. The answers don’t reside with you. To come up with the best roadmap, you need to learn as much as you can, and then organize and prioritize your findings to an actionable roadmap. The more you listen to others and learn the various points of view, the better your roadmap and product will be.

Step 3: Organize and prioritize your findings

Review everything you have written down in the previous step, and start finding commonalities. They could be very specific things that appear in multiple places, but you should not limit yourself to bundling only identical input. You might find out a number of requests to handle a specific area. They would be solving the same problem, but the specific requests could be different. For example, you might find various issues regarding scale, or onboarding, or stability. Create those higher-level buckets as themes, and assign the issues you heard about to them.

You want to make sure your themes are inclusive of the important issues you found out. Don’t feel like you have to include every little thing you heard about. In most cases, some of the input is noise.

You also want to check your themes and suggested solutions against your goals.

For each goal, ask yourself: if I resolved these themes using these suggested solutions, would I reach the goal? If the answer is ‘no’, think about what is missing. This is the time to be creative and come up with your own answers, they don’t all have to come from other information sources.

Mix and match your themes and solutions until you feel you found the right grouping that is able to satisfy all the goals.

Doing so will also allow you to have an initial, rough prioritization. The goal of this prioritization is not to organize your timeline (what comes first), but rather to separate the wheat from the chaff: you need to understand what is materially important and what is noise. The timeline exercise comes later, and this kind of prioritization knowledge will help you to shorten the process.

By now, you have your complete wish list for the roadmap.

Go back to your document and rewrite it as a complete end-to-end story: continue from the goals and reasoning you already have, to explain how what you have in your wish list will achieve these goals and why. This should include the breakdown to the high-level milestones, along with their definition and order.

Step 4: Time estimates

Before you even start discussing time estimates, you and your development lead need to be aligned on the narrative from the earlier step. Explain that these are your current (initial) thoughts, and make them your partners in creating the final version. Spend time with them, explain your rationale, and make sure to answer all of their questions. Their input might result in another iteration on the story. Don’t worry, it won’t be the last one so feel free to make the changes you feel are necessary and make sense.

When you get to time estimates, nothing in your document should surprise them.

As I mentioned in part 1 of the guide, the time estimates here need to be high level. However, to make sure they are generally realistic, you will probably need to define in a little more detail what each piece of the roadmap should include.

Don’t go too deep. and remember that the goal is to understand roughly when each milestone can be achieved, to understand if the entire roadmap is doable, or understand what additional resources are needed in order to succeed.

As in almost everything else in life, the 80-20 rule works here as well. Make the 20% effort that you need to get to 80% accuracy. Don’t waste the time of the additional 80% of the planning effort to get to a perfect plan. The final plan will change anyway.

Add the ETAs to your document.

Note that some time estimates might change your prioritization – some things might need to come at the expense of others, or sometimes something is so difficult and costly to achieve that you might need to leave it out for now altogether. Don’t forget to include the left out pieces in a dedicated section of the document, along with the reasoning of why they were left out.

Step 5: Create a whole that is greater than the sum of its parts

Now that you have all the layers, review them again to make sure they are well connected. Make sure the entire flow of the story makes sense, end to end. Check to see how you feel about this roadmap – are you proud of it? Do you feel that it will take the company to where it needs to be?

The latter question needs to be asked with your internal stakeholders as well. Go back to the people you interviewed in step 2 above, and present your suggestion to them to get their thoughts and feedback. I recommend doing it in 1:1 meetings and framing what you have as a draft so that they feel comfortable giving your feedback while they still have the opportunity to impact the final outcome. This is the only way to create the partnership you need with them.

Once you incorporated everyone’s explained feedback (don’t take what they say blindly, and it’s ok to see things differently), take it back to the stakeholders for one final review. In this meeting, which is no longer 1:1, people should not be surprised by what they see. They need to feel that you addressed their concerns from the previous round with specific refinements and that it all makes perfect sense. If you have a large group of stakeholders that you need to talk to, consider splitting to a number of meetings, but make sure relevant people sit in the room together so that they get a chance to hear other people’s feedback.

Congratulations! Your strategic roadmap is now ready. In the last part of this guide, I will describe what you should do next to ensure you make the most out of it.

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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