Wait! Before you create user stories…

In a previous post, I talked about my experience working for a company that had over 500 user stories (and counting!). There was no clear way to prioritize one feature over another, except by checking which customer was screaming loudest that week. The product was lumbering along, even though the execution was “Agile”.

In that post, I described a solution to such a problem: creating a vision and strategy, and developing a cross-functional strategic roadmap that can guide your execution. In this post, we’ll talk about how you can build that cross-functional strategic roadmap, and how you can make it actionable by loading it into tools like Trello.

Why a cross-functional strategic roadmap is important

Most companies have a one-dimensional backlog — it tracks what engineering (and maybe design) needs to do. In reality, while your tech team is working on the beta product, your professional services team might be working on APIs to simplify integration into the customer’s environment, your marketing team might be working on a sequence of activities that ends in the public launch, and your sales team might be negotiating friendly customer sites.

A cross-functional strategic roadmap ensures that you’re executing on your strategy in the most effective possible way.

All of these groups are working on critical aspects of your product strategy, with dependencies that need to be aligned. A cross-functional strategic roadmap can tie it all together, and ensure that you’re executing on your strategy in the most effective possible way.

Let’s use the example of Likelii, my last startup, to create a cross-functional strategic roadmap. You’ll want to use the Radical Product Toolkit to create a RDCL strategy for your product before you embark on a similar exercise for your company.

Start with the strategy

Below is a synthesized, cohesive RDCL strategy for Likelii, showing how each element of the strategy helps or hinders Vision and Sustainability. Considering the trade-offs between Vision and Sustainability helps you determine whether the proposed strategy results in too much Vision Debt, or if it over-exposes you to risk through too much Vision Investment.

This synthesized RDCL below addresses the pain point for amateur wine drinkers who are interested in drinking and learning about good wine, but don’t have the time to do research. We validated that this was a Real Pain Point by making sure it was Verified (this pain point was observable in our target segment) and Valued (users were willing to give something up to solve this pain point; in our case the “payment” was in the form of spending time answering questions about their tastes and browsing through the resulting recommendations).

Creating initiatives

Now that we have our strategy laid out, with an acceptable balance between Vision Debt and Vision Investment, we begin to consider how to execute on it. Transforming strategic goals from the RDCL canvas into actionable Initiatives is the next step.

Looking at this synthesized RDCL strategy, we can see a few high-level Initiatives that need to occur:

  • Providing recommendations based on mapping wines to taste preferences
  • Ensuring that recommendations are actionable by the user (i.e. available in stock for purchase)
  • Creating content and a subscription model for wine education
  • Improving the sales funnel
  • Optimizing the supply chain
Initiatives work best if you are using diverse, cross-functional autonomous teams across your product organization

These initiatives represent the starting point for your Strategic Roadmap. For each initiative, list the responsible teams and individuals. This is easiest if you are using diverse, cross-functional autonomous teams across your product organization, because each team will usually be responsible for a clear-cut set of initiatives. However, it can be accomplished (if somewhat less cleanly) under any organizational structure.

Now, Next, and Later

Next, consider the Milestones you need to hit to accomplish these initiatives over the “Now”, “Next”, and “Later” timeframes. Milestones should be concrete (that is, based on specific accomplishments, not activities to be done). We find it most helpful to phrase milestones in the past tense; this is a little psychology hack that helps your team visualize each milestone as an achievable goal.

In the Radical Product Toolkit, the Strategic Roadmap gives you the flexibility to decide the Now, Next, and Later timeframes that make the most sense for your product. For Likelii, an early-stage startup, our Now horizon was up to a year, the Next time horizon was 1–2 years, and the Later time horizon was 3–7 years.

Above is a view of the Strategic Roadmap worksheet filled out for Likelii. Notice how a single initiative evolves over time through the milestones. “Optimizing the Supply Chain” in the short term (“Now” column) meant ensuring that our customers were getting the wines they ordered in the shortest possible time. This meant finding suppliers who were quick to ship and cared about customer experience. In the longer term (“Next” column), this meant expanding the number of suppliers so that we were shipping wines from the supplier closest to the customer, to further reduce order fulfillment times.

Build it together

We encourage you to craft this Strategic Roadmap together with experts in each functional area, so you can and review and debate the milestones with them and get their buy-in. Before you embark on this as a joint exercise, however, we recommend that you fill it out yourself first. This first draft will help you anticipate the areas where the team is likely to get stuck, so you can facilitate the discussion better.

Once your initial pass at the Strategic Roadmap is complete, it becomes a living document. Every week or two, when you check in as a cross-functional team, you can bring up your Strategic Roadmap and discuss if you’re aligned to deliver on those milestones.

Execution and Measurement

Now that you have a cross-functional roadmap to create alignment across initiatives, you’re ready to translate this into an Execute and Measure Model. Looking at your Strategic Roadmap, for each Initiative, break out each Milestone into Activities, Hypotheses, and Metrics. Below is an example of one Likelii Initiative being translated into Execution and Measurement.

Cross-functional expertise

As you see from this execution model, delivering on a milestone might involve activities across different functions. For example, Likelii’s Sommelier in Residence would describe a wine recommendation algorithm, and Engineering would build the algorithm into production.

Again, this is why structuring small, cross-functional Product Experience Teams (PXT) is ideal — they make delivering on milestones more efficient, and clarify lines of communication and responsibility. For example, the Quiz Experience Team would be delivering the Initiative of “Recommendations based on mapping wines to taste preferences” across multiple functional areas.

Metrics, hypotheses, and activities

When you fill out this Execution and Measurement Model, start with the metrics. Ask yourself: what metrics will tell us that we are making progress toward our next milestone? Next, list your hypotheses on what activities would move these metrics, and why.

For your hypotheses, we recommend using a simple “If... then... because…” format. This structure ensures that you’re thinking about what actions will help move the metric in the right direction, and (even more importantly) it forces you to state clearly why it would move in that direction.

For hypotheses, state what actions would help move the metric in the right direction, and (even more importantly) why you think it will move

Once you have your hypotheses, break down the activities into concrete actions to take, and write those down in the right-hand column. The scale and scope of these actions should be actionable, and assignable directly to an individual or small group. If an action is too broad, or too vaguely defined, it probably won’t be executed on effectively.

How often do we come back to the Execute & Measure Model?

How often you refresh your Execute & Measure Model comes down to how quickly your team works, but it’s likely that you will load up new activities multiple times per week as old ones are checked off the list. Whenever a hypothesis is invalidated (that is, you take the action and it doesn’t lead to the expected result) it needs to be cleared out and replaced with a new one — this happens very often in early-stage products, and less often once the product is more established.

Finally, if you’ve banged your head against the wall too many times with hypotheses that don’t seem to move your goal metrics, you may want to reconsider the metrics you’re targeting. This should not be taken lightly, but it can be the right choice if you realize that you’ve been measuring the wrong thing.

Translating the Execute and Measure Model into the tools you use today

With the team’s Execute and Measure Model complete, they can now use any PM tool of their choosing to input their activities and report back on progress. Below is an example of how the Quiz Experience Team could use Trello for execution, but they could create something similar using other tools like Pivotal Tracker — or even Excel.

The two Milestones the Quiz Experience Team is working on are color coded (“Developing a Taste Quiz” and “Developing an Algorithm”). Each green card, for example, represents an Activity towards Developing a Taste Quiz.

These Activities are effectively the cross-functional team equivalent of user stories. If you are using a sprint-based execution methodology like Scrum, you should be able to accomplish each card in the duration of one sprint. If an activity is too broadly scoped, you should plan to break it down into smaller, more achievable pieces.

When reporting up to the product organization’s leadership, teams can discuss progress on their Initiatives using their desired tool. In this case, the Quiz Experience Team might have Trello open, and report back that they need more resources on user testing to move those cards to the “In Progress” column. This gives your product leadership better visibility into how day-to-day activities influence strategic milestones, letting them make course corrections as needed.

With this post we have translated the abstract concepts of Vision and Strategy into a Strategic Roadmap, and tied the Execute and Measure Model into everyday tools for execution. This should equip you well to build vision-driven products using the Radical Product Toolkit!

Download the Radical Product Toolkit and reach out to us with questions as you start using it to craft your Vision, RDCL Strategy, Strategic Roadmap and your Execute and Measure Model. We look forward to hearing from you!