For me, the roadmap is a strategy document, and in the end of the day it's all about getting a group of people (your colleagues) on the same page and create alignment about priority in the organization. The roadmap should explain what bets we will focus on and what problem the bets are solving for the business and our users. But the roadmap also explain why we have decided to do them in a specific order, what's behind that, and what is the business outcome we can expect if we do it like this.
If you have been a good product person and done the discovery work together with your team, then you should have a good understanding of the various risks in each bet, then I don't see any big constraints with putting the bets plus expected business outcome on a timeline. But make sure to add quite a lot of margins in the end for unknowns that you might have missed during the discovery process.
If you are new to the team or if the team doesn't have any structured ways of working with discovery, then I would recommend doing a 'Now, Next, Later' roadmap instead. It’s easier and less things can go wrong. And it is an efficient way to communicate the priority on bets and create alignment. The downside of a 'Now, Next, Later' roadmap is that it doesn't say anything about when the bets are expected to be shipped to the users and when the expected outcome will be reached. If you do a Now, Next, Later roadmap, you need to reason around that, inform the audience why it's hard to estimate the time, and how you will work with your team to discover all the 'unknowns' in every bet. But I would say that in most cases this is a great and easy way to communicate the roadmap.
Another way to align your colleagues around a plan is to introduce the concept of an 'Opportunity solution tree'. This is something that you can start working with within your team to create alignment, and when you have alignment within the team, then this might be a great way to also create alignment outside of the team. Opportunity Solution Tree is a great way to get everyone on the same page about what the most important outcome is for the team, but also how the problem space looks like. But go slow here and anchor the concept in smaller groups before moving forward in the bigger organisation. If done right, this can be something that really creates alignment, if done wrong and too fast and without context, this can be something that harms.
There is also a concept that I call a 'strategic roadmap' that connects ongoing work, future bets, and biggest themes to the vision that I have found very useful. But I will be covering that more in detail in another blog post.
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