Roadmapping Fear
I've made so many product roadmaps I've lost count. As a PM, as a product leader, as a stakeholder. For B2C products and B2B products, for software and hardware. For early stage startups and for 100 year old grocery companies doing $30B+ in revenue. Using every different methodology -- waterfall, agile (pick your flavor), Shape Up, everything Marty Cagan has ever advocated.
Everyone hates roadmapping. Literally everyone I talk to. They're frustrated and the number one piece of advice I get asked about (from product leaders and CEOs alike) is "how to roadmap better."
Maybe we should just kill off roadmaps. As Marty writes, "Typical roadmaps are the root cause of most waste and failed efforts in product organizations."
But roadmaps serve a critical purpose. Is it to prioritize, to allocate resources, to communicate clearly internally and externally? Yes, but:
The most important function of a product roadmap is controlling fear.
Everyone involved in the process is terrified, and no one will acknowledge it.
CEOs are scared (or call it worried, if you prefer) that they'll sign off on the wrong prioritization decision and miss an opportunity. That the thing they've promoted to the board as the future of the company will slip by a quarter, or two. That the product and engineering teams are sandbagging the estimates (they are). And that they really have no idea how it all works (most don't).
Other executives are scared because they have a number to hit, and there's usually a gap-to-goal that they're probably not entirely sure how to fill. So throw something onto the roadmap! Swear to god that it'll close the gap (they’re just guessing). The head of sales is sweating how to have that conversation with a key customer who was sold on a particular feature that doesn't exist yet and oops, no one told the product team.
Engineers and designers are scared because they know they're going to get signed up for wildly unrealistic expectations -- too many items, all with hard deadlines, probably with poorly thought out requirements, and with all sorts of resource and talent bottlenecks no one identified until too late. And once the roadmap is final, good luck trying to change it. You either work crazy long hours to hit the deadlines, and/or you miss but it's your fault for not working hard enough (certainly not because of a flaw in the process).
Meanwhile PMs and product leaders are in the middle of the fray and trying to calm all those fears. The best ones are trudging along while praying for it to be over (because roadmapping is not why anyone got into product -- roadmapping is theatre, not building). The worst ones are fudging the data or exaggerating the scope to either get their pet project approved or to ensure they have a very cushy deadline or unnecessarily low expectations.
But without roadmaps all these fears still exist, just deeper in the shadows, which causes even more dysfunction.
So, how do you run a healthy(-er) roadmapping process?
Acknowledge the fears. Talk about them openly. The CEO needs to set the tone here.
Practice empathy and genuine curiosity. Fear dissipates as understanding increases. Most companies are wildly under-invested in creating cross-functional context, and that under-investment shows up most during roadmap planning.
Use strategic themes to create shared understanding. These themes describe buckets of related products, features and projects, ideally tied to business outcomes. These ensure that product roadmaps are not just a "product thing" they become a "company thing."
Embrace rolling six month roadmaps. The first quarter should be fairly precise -- well estimated with clear expectations and limited surprises (there are always few). The second quarter should be "penciled in." These gives everyone a sense of what's next and what should be researched and prepped for, but critically there are no deliverable dates and the process assumes that new information will emerge in the first quarter than changes the penciled-in second quarter draft. Refresh every three months.
Be judicious when asking for "signed in blood" roadmap commitments. There are certain initiatives or product launches that are truly must hit by a certain date. And when great product and engineering teams are clear on this, they will hit the date, with quality, come hell or high water. Unfortunately, many CEOs and executives over use the designation, and when everything is must hit, then nothing is and discipline is lost.
Follow these tips, and your next roadmapping adventure will be lower anxiety than your last. Good luck!
