417: Using roadmaps with OKRs – with Michael Harrison

A process for improving product roadmapping using Objectives and Key Results – for product managers Today we are talking about roadmaps. Some product people love roadmaps, while a lot hate them. What can make them better? Our guest has had good experience creating roadmaps from objectives and key results (OKRs), and he is going to tell us how. That guest is Michael Harrison. He is the Head of Product Management for Fleetio, a SaaS company that automates fleet operations to keep vehicles and equipment running smoothly. Summary of some concepts discussed for product managers [2:11] What are approaches to product roadmaps have you used? As Fleetio has scaled, the needs of our roadmap have changed a lot. When we were small—seven employees—we operated on a project-based roadmap, a series of features with goals and timelines for when we hope to deliver those. That worked pretty well. When we were small, it kept us focused and we could afford major changes in direction. Now, as we’ve evolved, we need more of an outcome-based roadmap because it naturally keeps us more aligned as we get bigger. [3:58] What led you to incorporate OKRs into your roadmaps? The first change we made was switching to more theme-based roadmaps. Having narratives for product strategy is inspiring and allows the go-to-market side of the organization align with product more easily. We found if you just select roadmap themes and put them on a yearly cadence, it’s hard to judge relative priority among themes and choose a cap for how many themes you should have. If you’re a customer-led organization, almost every idea is a pretty good idea. The question is, what are the best ideas? For the last two quarters, we’ve been doing OKR roadmaps, and it forces us to make sure everything we’re building ties up directly to our company’s objective. It forces us to think about relative priority because we can only choose a couple of things to ladder up to the top company objectives. You  need narratives, but you also need some cap on how those narratives tie to your strategy and how to measure which ones are making a difference. [6:46] Have you found times when the strategic objective wasn’t the most helpful thing to guide OKRs? Yes, how you are going to pick the right things is the principal challenge of roadmaps. Not all your ideas are going to work. Think of the product team more like the marketing half of your organization—half of your ad dollars will be wasted; you just don’t know which half yet. The question is which things will have the most impact and can you reduce the impact of the things you’re going to get wrong? The OKR structure has given us a way to measure the impact of things. We don’t just have a flurry of activity each quarter. We have a flurry of activity in specific categories that are measurable. [8:16] What is your process for roadmapping with OKRs? I think of our process as a four-layer ladder. We tie everything the company is doing up to five unchanging OKRs at the top level, for example our annually recurring revenue (ARR) is our North Star metric. We also have metrics for retention and expansion. That’s level one—company strategy. Underneath that in level two, we think about what the product needs to do over the next year. What do we need to get better at? What kind of mission do we need to be on for the product to drive revenue, retention, and expansion? Level three is what can we do this quarter? That’s where time bounds are very important because we’re planning where we want to be by the end of the quarter. That’s our outcome-based roadmap. What does the product need to achieve for users? What leading indicators can we measure that would tell us we’re driving the level-two product mission. Level four is our roadmap. Those are the ideas, experiments,