Four practical tips to make your annual roadmap more actionable
Night falls early on these cold December days. The snow-covered streets are deserted and dark. Yet, in the distance, a light still flickers behind a lone window of an office building. While most people cozy up in a blanket on the couch, a small group is still toiling away at night. Their short meeting has been going on for nearly 4 hours now.
Ho! Ho! Ho! It's road mapping season!
It's a quaint tradition of company life. Every year we make next year's Big Plan. Every year we underestimate how much time and effort we sink into that annual road mapping session.
And every year, we fail to do what we set out to do the year before.
The roadmap has gained divine status among companies that build software products. Believers will swear by it and go into great detail to make sure it's correct this time. Heathens will call it an exercise in futility and exclaim that you can't predict the future.
While many of these theological discussions on the nature of roadmaps are fascinating, they could be more practical.
With the year coming to an end, let me give you four practical tips to create a more actionable roadmap for 2023.
1. Make it unified
The roadmap visualizes all the strategic work your company intends to do. It doesn't need to go into the nitty-gritty details, but every initiative planned for next year should have a place on that timeline.
What I see too often are "departmental roadmaps". Sales has a roadmap. The Web Team has one too. Every department, from Customer Success to Marketing, has done its homework and has produced a Big Plan. Since most departments aren't silos, there will be interplay, which goes largely unplanned. Sales wants to launch a big push into Sales Automation tools in 2023, but that requires the assistance of the IT department. Guess who's just crammed their year full of quality initiatives?
Isolated roadmaps per department or team create planning conflicts from day one. If your organization has multiple roadmaps, try to consolidate them on a single timeline and figure out where they might collide.
2. Make it hierarchical
Some companies describe the work they intend to do in excessive detail. There really is no reason to write User Stories for three months down the line. But other companies make their roadmaps too high-level. They see the roadmap as a visualization of valuable strategic initiatives. They don't want to clutter that with the business-as-usual work.
I've seen overworked teams design roadmaps of everything they will build on top of their regular workload. The teams that can't complete a single sprint will somehow find the time to side-hustle their roadmap? Unlikely.
Roadmaps should be hierarchical and top-down. It should be possible to drill down on each roadmap item and reach the work items developers will collaborate on. While bugs and small tasks don't need to be on the roadmap, it should be possible to trace all feature work back to a roadmap item.
Hierarchical roadmaps ensure we work on what we say we would work.
3. Plan recovery time
Software teams spend between 25% and 50% of their time maintaining existing code. Yet whenever I look at a company's roadmap, everyone acts as if they're building features 100% of the time. Such a roadmap is doomed from the start. Churning out feature after feature surely looks ambitious and impressive on your slide deck. It feels less great when you already have to temper that ambition in Q1. Actionable roadmaps should account for operational work. Make it a habit to plan one or two weeks of recovery time after each roadmap item. That way, maintenance is incorporated into the plan. It also creates some handy buffers to stop the domino effect should your overly ambitious plan start to slide.
4. Plan quarterly reviews
Once the roadmap is completed and everyone is aligned, we send out the final e-mail and close our laptops. We've made it! Time to join the company's Christmas party. Three hundred sixty-five days of non-roadmap bliss are ahead!
I strongly advise organizing a quarterly review of the roadmap. As soon as you send out that final e-mail, book a recurring 1-hour meeting at the beginning of each quarter. The same people who created the roadmap should review its targets. Are will still on track? Do we need to reshuffle the plan? Does this roadmap still align with our strategic vision, or did we discover better opportunities last quarter? Finally, it allows the team to add one more quarter to the long-term plan.
Planning is an ongoing process of capturing feedback and steering the tanker. By having these quarterly reviews, we kill the need for the Big Roadmap Session at the end of the year. Building actionable roadmaps becomes a company habit rather than an annual event.
It makes our long-term plans more reliable.
And it allows us to join that Christmas party earlier.
Next week marks the start of my holiday season as well. I'm spending the holidays with my family in Romania and will pick up the newsletter in January.
I wish you a fantastic end of 2022.