How do I estimate blocks on my roadmap?

I get this question all the time: How can we accurately estimate the roadmap items so we can set expectations with leadership? My answer is always the same, “You, product, get to choose how long you will invest in roadmap items.” I repeat… YOU CHOOSE! Then it is your responsibility to prioritize the backlog items appropriately.

Let’s take it back a notch. If your teams are set up to deliver around outcome driven goals for your product and meant to own the care and feeding of a product, then we should no longer be in that project mindset of “we need to get it all done and move on”. YOU ARE FREE!!!! Do only what you need to do to start learning if you are on the right track, then make a decision what to do next. If you budgeted 4 sprints for the roadmap item and you get 2 sprints in and have delivered all the really important features and have moved into nice-to-have items, trim the tail! Move on to something else. Do you need to let it sit in production to see how users are responding to it? Move on to something else and come back! Have you gotten 4 sprints in and you are still delivering real value? Discuss with your stakeholders about investing more time to continue gaining value! You are in control.

But Reese, what if I budget 2 sprints and the team is like, “Woah woah woah! We can’t deliver on the outcome you are expecting in 2 sprints!” Alrighty, here is where I go back to your original question. How do we estimate? Take the items coming up to the team and size them against each other. I’ve found t-shirt sizes work really well for this. The team can quickly determine the size of the item relative to ones they’ve done before and boom! You have some data to work with. You can look back at past data and roughly say, “Cool! I’ll budget a sprint for an XS, 2 for a small” and so on based on how things went before. Do not tell them these equate with time. I repeat. DO NOT TELL THEM THESE EQUATE WITH TIME. If you do, it breaks the whole system. It will likely change over time, so you’ll need to readjust your translation.

You take that info, build a roadmap, and then as I started this story with, the onus is on you to prioritize correctly within the timeboxes you’ve set. Or renegotiate the timebox.

Easy peasy lemon squeezy.