📅 Now, next, later
Guide to a Flexible Roadmap
Think of a perfectly planned and executed roadmap.
How often have you prepared and carefully laid out a neatly prioritised and estimated year of initiatives and deliveries? Something like this:
It’s like a perfect little story. A three-act structure. The beginning, the middle and the end.
End of story. End of the newsletter. Goodbye! Have a lovely week.
But wait a minute…
Do you genuinely think this depicts at all the reality?
As you look back at your year, that excellent plan above looks more like something like this:
So many things happen throughout the year. Especially in companies that have a fast pace, where you plan and lock in a yearly fashion, the image above is inevitable.
From having wrong estimates, shifting priorities, unexpected requirements, and changes in capacity, you have to be nimble enough to navigate through these times while simultaneously being capable of creating and executing a plan.
So as an Engineering Manager or as someone responsible for creating and maintaining your team’s roadmap, how can you work through this?
My suggestion is to focus on a more flexible approach, something that accommodates change and, at the same time, gives you enough assurance that you can manage a stable team.
The Now, Next, Later format was created by Janna Bastow in 2012, and the focus was to create a roadmap view focused on priorities and problem-solving instead of a deadline-based delivery.
Bastow creates three main buckets:
Initiatives that you are currently working on right now.
You have a high degree of detail on these initiatives.
Once everything you’re working on NOW is complete, you’ll tackle this.
You don’t have as much detail, but you know that they will be a priority.
Everything else you have set on doing but still without a defined date.
Very little detail, only broad ideas.
Allows you to know the direction you’re taking.
I’m sure you’re now thinking about how this is all a pretty essay, but it doesn’t fit your reality because you must deliver a timeline-based roadmap.
There’s no way a hip roadmap technique like this would ever work at your company.
Let's see how to use this technique and revisit our wonderful year roadmap above.
Start by understanding how these straightforward concepts can change much of what you’re doing.
Looking at the buckets, you’ll notice a couple of 📉 downward trends as you go from the NOW to the LATER buckets:
The degree of detail you have on each initiative
The impact of shifting priorities
The level of preparation you need for each initiative
What if we tried to apply Now, Next and Later definitions to our yearly roadmap?
Notice how you don’t have a later in this view. That’s because, in the definition, the Later column doesn’t have defined dates, so you end up with nine months of Next.
How can we improve this view? Focus on a quarter view.
First, let me highlight that you should revisit the plan monthly for this technique to work. This allows you to quickly change and take full advantage of the Now, Next and Later roadmap.
Let’s go back to the buckets and define them a little more.
The next three months - M1, M2, M3
Avoid changing anything in the next month (M1) at all costs, but allow some change in the following two (M2, M3).
You have great detail on these initiatives (motivations, dependencies, complexity, workload, estimation, etc.).
The following three months - M4, M5, M6
Be flexible to change here as the level of uncertainty is higher.
You should prioritise your initiatives, have a high-level estimate, and have critical aspects like identifying and informing dependencies.
Be ready to shift things around, but you know what to tackle next.
The final six months - M7, M8, M9, M10, M11, M12
Let’s face it. You have absolutely zero guarantees here. All you really have is an idea of what you’ll work on.
Keep a tidy backlog of initiatives and review them often so you’re ready to put them in the next bucket.
This would bring our yearly roadmap to something like this:
I can’t stress enough that even when you’re using a more flexible approach like this, you must know your hard deadlines and prepare accordingly. There’s no excuse if you don’t prioritise a delivery that is ten months away.
As a manager, this system will help you have a better lock of what your team is focused on in the next three months and for the team to feel less of the noise of priorities changing constantly.
Finally, let me just highlight that you shouldn’t shoot for a perfect roadmap.
It doesn’t exist.
Work instead on your prioritisation skills, your reaction time for when things change and how you deal with customers and stakeholders.
I’ll see you next week