Opportunities roadmaps: connecting OKR planning with continuous discovery

It is that time of the year, if you are working with product development, chances are really high that you are spending the last days of 2022 trying to craft a plan for 2023. And while doing that, you probably find yourself debating about one thing: the roadmap.

Many questions might be spinning into your head. Anything from questioning if you should have a roadmap, to battling to define an outcome-based or problem-based roadmap as opposed to a feature one, trying to align your plans with the ones of some other teams, or getting that stakeholder’s sign-off without which you hit a roadblock. The struggle is real, I know. This is why I thought I would share the approach that we took this year at Hemnet.

What we are testing is what we call the business opportunity roadmap, which is basically a mapping of the interesting investment areas for the company, and the areas that we will put our product development focus on.

It is a way to connect the dots between goal setting, discovery, and clarity throughout the entire company. It tells us the areas we will focus on, and the problem we will try to solve to create an impact. But not how we will do it as that is feature discovery work.

I started to lay down the different pieces of the puzzle before summer, as a step to scaling our continuous discovery practice, and that work is coming into shape now. We are not done yet, but I already have some takeaways that I thought could be useful for other also thinking about their roadmap work.

Roadmaps are prototypes, not commitments

I have been one of those people in the room who really reacted every time someone mentioned the word ”roadmap". I literally had people telling me that I unconsciously was rolling my eyes every time someone even said the R-word. But of course, it is not the concept of having a plan in itself that I am against, it is what is unconsciously connected with that word that scares me. Roadmap more often than not means a closed plan, expectations on delivery, and maybe even a date attached to a really specific feature that someone thinks is really important to have (but we cannot really connect to any kind of effect or bigger plan).

Let’s put the record straight, I was, and I still am, really against using roadmaps as a way to lock your entire year into a certain number of predefined initiatives. This would mean that you have all the answers and that nothing in the world around you can change. If you are, or ever found yourself, in that position of total magic where you can read the future and freeze time, then by all means go ahead and have defined feature roadmaps, it will give you TONS of wiggle room against your competitors. Unfortunately, I was never that lucky of finding myself in that position, and more often than not what I experienced is that information changes, we learn, and therefore we should adapt and not follow the plan blindly.

But this doesn’t mean that because we do have not all the answers, we shouldn’t lay down a plan about how we intend to succeed.

There is another way of looking at roadmaps. They should not be seen as commitments or super detailed plans but as a lineup of our best bets to execute our strategy.

Janna Bastow said it best at the latest Product Elevation conference - your roadmaps are the prototype of your strategy. AMEN!

What we want to do is start mapping the areas that we believe will drive the effects we want to see in our product strategy. And by starting to execute those, we will be able to either take a step toward our goals or realize that we have failed and need to rethink.

And where do these areas come from you might ask yourselves - easy! These are the result of all the discoveries you have done, the input that the customers gave to you, the data you looked at, and the changes in the market that you observed.

You surely have an idea, or some, where you should start putting your focus on bringing our strategy to life, and this is what we should start mapping as a means to have a conversation with all your stakeholders.

I was astonished by how great of a discussion starter having those opportunities proved to be. This brings me to the next learning…

The value is in the process

The bigger takeaway I have so far is that mapping is key. As soon as you start mapping, you have something visible and a bit more concrete that can be discussed. And I assure you, making things explicit is really getting half of the job done.

Example of how we structured a roadmap from an outcome coming from the product strategy.
All the examples are purely illustrational

This is how we lined up the work since after summer:

1. Review our product strategy by refining more specific behaviors we want to drive
   This was the result of 1,5 years of working with the strategy and learning a lot. Where we are heading is the same, but I felt a need of making some behaviors more specific, to highlight the importance of certain areas

2. Define how we measure success in these areas
   Making explicit how we measure success in each area, some people would call these ”north stars”, to me are the metrics we always have to keep in mind

3. Map business opportunities from a 3-year perspective
   This gave an overview of all the things we could do to drive the strategy, as well as a great first visualization of how the different parts of our products interact with each other

4. Starting to select some of the business opportunities for next year, as a kick-start of the OKR planning

And here comes the interesting part - having step 4 really helped in taking the conversation about planning and product development investment on a level of abstraction down.

I was the one doing the first selection, but not at all the one who worked the most with it. What happened is that ”just” by starting to point at some business opportunities, and making more concrete the areas of focus created a cascade of healthy conversations between me, the PMs, and the stakeholders. These conversations would most likely happen anyway, but with this process, they were taken upfront.

Here are some examples of what we discussed about:

• We talked about connecting goals and business opportunities

• We talked about what are really the most important business opportunities to pursue

• We talked about synergies cross-products and products-portfolios

• We talked about risks

• We started to see trade-offs early

• We could have a more top-down, down-up approach to goal setting

• We created a level of transparency and understanding for others who are not so deep into the details

• We identify tech enablers that were not so easy to see when we prioritized only objectives on a level of abstraction up then the business opportunities

Of course, all these new conversations were not all a walk in the park. What I introduced was a change, and more than one person did not recognize him or herself in this new way and sometimes felt pressured or not included. Questions like ”who decided on those things” to ”why delivery in this quarter is so important” popped up and created some turbulence. But I believe that, beyond the beginner effect, it will not take long until more people will see a lot of benefits with this new approach. The biggest being alignment and clarity.

We are right now only in the planning phase, I do not know yet about the efficiency that this might bring. But the signals are all pointing in the right direction.

Find a balance between diverging and converging

Maybe the biggest risk for us with this process is communicating clearly that this new step is a way to scale our continuous discovery. Converging on some business opportunities doesn’t mean that we are working with ”fixed roadmaps”, quite the opposite, it is about using our learnings to define more clearly where to put our energy in order to prove ourselves right, or wrong, even quicker.

For me, this process is about striking the right balance between diverging and converging. Not everything needs to be in a ”diverge” mode all the time, we should have a good understanding, based on all the research we have done, of where we want to place our bets (select/converge) and where we need to dig head-down into discovery.

The business opportunities roadmap is a way to pin some focus areas, explaining why they are the ones we want to bet on, and really put all our attention into executing them, until we are proven wrong. It is about defining an area of focus, but not the way we will execute it.

In my head, it is a dance of diverging and converging, optimized for learning quickly and proving our product strategy.

This is how I think about balancing diverging and converging in the planning work

But for some pinning down more concretely some business opportunities, no matter how open for discovery they still are, felt like having an execution list. ”Why do we have to converge” or ”why aren’t all things open to discovery now?” were by far the biggest reaction I got.

And considering where we stand with our discovery practice and organizational scale, I feel that the golden balance of pointing at what to discover (a business opportunity or a solution to a business opportunity) is the nut to crack. I believe the two go hand in hand, but I will be extra mindful of monitoring that we learn and evaluate not only the solutions but also the business opportunities and that we make sure that our ways of working with continuous discovery are at the very heart of this new process. To be continued with some more learnings as we get deep into executing in 2023.

And what does your roadmap look like? Are you testing anything similar to this?