Realistic startup roadmap planning

We're a little ways into 2016 but since I've just gotten back from my travels, it really feels like the beginning of the year to me.

Calendar time breaks like years and quarters naturally lend themselves to planning for the future. As a product person, this usually means it's roadmap time! Ideally, you're not waiting until the end or beginning of a year to sit down and then have a giant planning session with the big extended team in which you map out the entire roadmap for a year. Invariably, this results in a grand aspirational strategy which will stay in a beautiful unsullied shell for exactly one week before engineering realities, new strategic partnerships and unexpected growth (or lack thereof) intrude.

Of course, that doesn't mean that planning is useless. The last thing you want your product team to be doing is aimlessly launching bits and pieces that don't make sense in a larger context. However, it's important to understand what your planning session should focus on and what you just don't know and shouldn't try to detail out in that session.

Whether it's a product roadmap or a new company venture, here's a framework I like to use for the outputs from a single roadmap planning session:

  • what's our one focus and why?
    • e.g. validating assumption X - it's the largest need for our target audience
    • e.g. improving metric Y - it's the single biggest contributor to revenue
  • what are the one or two key metrics that we'll track?
    • e.g. engagement, new user growth, revenue
    • include the set up for how you will monitor it - query, dashboard, automated report
  • what are the high-level products for this focus?
  • what is the priority for those products?
    • based on how well related it is to focus and how much we think it will affect the relevant metrics
  • what's our timeframe to revisit the roadmap?
    • arbitrarily, two to three months feels like a good amount of time to build something that can actually show results
    • this is not a timeline for project or sprint planning

And that's it. The key thing here is that this is a single session. In short order, teams then have to take this roadmap and actually get into the guts of building out the product and features.

Ideally, the roadmap helps guide teams as they go through this process. It creates a sense of focus by acting as the magnifying glass under which we view product development in a specific timeframe. At the breakneck pace of a startup, there's always something more to be done and something new to deal with. A realistic and tightly defined set of goals can help us keep the momentum to build the most important products for the company at that specific time.