Managing a product without a roadmap is like driving off road.
April 2017 update: my thoughts on roadmaps have changed – if you’re working in Agile, be sure to read Why Agile and roadmaps don’t mix.
Not every product needs a roadmap. If the product is really young and you’re still trying to find product/market fit, don’t waste your time planning a roadmap that’s probably wrong. Instead, spend your time building what you think will sell and iterating based on feedback. (yes, I’m assuming you’re building your product using Agile because it’s 2016)
But if you have a lot of stakeholders (clients, sales, marketing, support, operations, etc.) who need to have an idea of what’s coming down the line, you’ll need a roadmap. Here are 5 tips:
1. Group changes into epics.
Ideally you’re grouping together changes based on the problem you’re trying to solve for a user. For example, with HelloWallet, we recently spent a few sprints focused on helping users decide how to juggle their savings and debt paydown goals simultaneously, since we knew from our user research that it was one of the toughest choices our users were facing.
The reason to group changes together is for efficiency sake. If every sprint is a hodge podge of user stories that cover a bunch of parts of your product, there’s a lot of context switching for everyone on the squad — design has to understand the existing UX and suggest changes, engineering has to touch different parts of the code base (some of which might have cobwebs on it), and QA won’t be able to prioritize regression testing scenarios since you’re changing things all over the place.
2. Prioritize epics based on KPIs.
A roadmap is nothing more than a listing of the things that you think have the highest likelihood of moving your KPIs (in particular, the $$$ KPI I discussed yesterday).
Prioritization is a science and an art. You can get scientific by creating a score card to evaluate epics on their likelihood to move different KPIs, or based on other factors. You can edit the weights of the different factors easily so that you’re scoring epics consistently.

The art comes in with a gut check of whether you’d actually prioritize epic 3 at the top of your list. Maybe you socialize the score card with your squad and get some qualitative feedback (“ugh, that?” from your favorite engineer or “oh, shit, that’d be killer” from your favorite sales lady). And you adjust accordingly.
3. T-Shirt size epics.
As a Product Manager, you should never make up timelines. Mainly because you’re not the one doing the work. You’ll need buy in on timelines. No one on your squad wants to feel like they are handed an unrealistic timeline and have to execute against it. Hence getting them involved in the process.
At HelloWallet and Morningstar, we use t-shirt sizes to get us in the right ballpark for an epic (it’ll never be very accurate). We start by writing the epic as a user story and getting a group of people together to estimate it — tech, design, product is usually a good starting point.
During estimation, a million questions come up. That’s why we write down assumptions to make sure we’re all on the same page in terms of scope. (“oh, what about this scenario?” — make an assumption about how to handle that scenario).
T-shirt sizes are as follows:
- XS = < 1 sprint
- S = 1–2 sprints
- M = 3–5 sprints
- L = 6–8 sprints
- XL = 9–13 sprints
Once you have an estimate, get conservative and use the high end of the range. Assume you forgot about some part of the scope or that something you all thought was going to be easy will be hard. No one will ever complain if you execute on your roadmap faster than you said you would (well, I suppose the would if you ALWAYS executed faster). But they’ll really give you the stink eye if you’re late in delivering something they planned for.
4. Build a 12-month roadmap.
Don’t try to plan the next 3 years — it’s gonna be wrong. Just plan the next 4 quarters.
At Opower, we ran some stats and found that our roadmaps were really accurate for the next quarter, pretty accurate for the next two quarters, and almost always wrong after 6 months. That’s not bad — a lot changes in 6 months (especially at startups).
5. Get feedback.
Socialize your roadmap, especially with sales. If they shake their head, find out why. Is there something else they think would be more meaningful? Talk to other people in your organization, even ones who don’t work on your product or in your business unit. And in true Agile form, iterate the roadmap (once or twice). But don’t update your roadmap more often than quarterly. As you can see from above, there’s a lot that goes into the process. If you’re updating it monthly, you’ll never have time to execute on the roadmap.
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