Road-mapping is a contact sport.

For the un-initiated, putting together a roadmap always seems like it should be a simple process. A roadmap is just a single piece of paper after-all. How hard can it be?

We've got some news. When done properly it should be hard. In fact road-mapping should be a full-contact-sport. What do we mean by that? Road-mapping is where the rubber (your strategy) meets the road (the market). It should put the top decision makers in a room to make company impacting decisions. For the best results, it shouldn't be a comfortable experience.  It should be agony. Ok, maybe not agony, but road-mapping should be a high-energy debate to ensure the right decisions are made. 

"Ok, I got it", I hear you say, "Let's talk about how to make it a contact-sport." 

Right, let's do that....actually, one thing before we get started. Let's talk quickly about why we recommend roadmap's even for the earliest of startups. Road-mapping is a process of assigning your resources to deliver on the most important things you've decided you need. When you're a 5-person product team with a 20-person dev team, spread across 4 scrum teams it becomes a complex process. But when you're three guys in a garage, why bother? Well, by skipping formal roadmap discussions what you're really missing is the goal setting process for your startup. As we'll discuss, road-mapping (or at least proper road-mapping) forces you to decide what the business needs most. The temptation for early startups is to skip the roadmap and thus skip the awkward goal setting conversation. Not good.

Ok, back to our regularly scheduled blog post. Let's talk about 3 ways to make sure you get the productive full-contact road-mapping we're talking about.

Be the google maps of your startup

Coming to the road-mapping table without a common understanding of strategic goals across your decision makers is a fundamental error. It's akin to an explorer sitting down with their team to chart a course for their adventure and not agreeing on their destination. While it's a fundamental error, it's an easy mistake to make because many startups don't have a clear understanding of where they need to be at the end of the current planning horizon. Much like google maps forces us to enter a destination before optimizing the route for us, the product leader needs to ensure strategic goals are in place. They need to be the google maps of their company. Sometimes it can feel like pushing a rope trying to get this alignment. However, there is no point passing go on road-mapping until you have agreement on the strategic goals.

P.S. As Des Traynor over at Intercom points out, you can see this go wrong when the work on your roadmap doesn't look anything like the strategic vision you use to describe your company. Oops!

P.P.S. The other current "when-roadmaps-go-bad story" is the bloating of the Evernote platform.

Frame, frame, frame.

OK, so I know we said that road-mapping is a contact sport, but like every sport it needs rules of engagement to enable constructive conflict, rather than destructive. We see many VPs of Product making the mistake of not framing the road-mapping process, i.e. they don't set the rules of engagement. The rules of engagement break down into two topics - the prioritization process and the current proposal. There are any number of different feature prioritization methodologies to chose from, but it's the product person's job to find the right one for their company and propose it (Note: Daniel at foldingburritos has collected a really great portfolio of them here).

The other part of framing is to put forth your proposal for the roadmap you believe is most likely to achieve the strategic goals (remember those goals you all agreed on before!). In the absence of a proposal, your road-mapping peers will have nothing to push against. This creates two problems. First, you'll look silly because as the product person you haven't come up with a roadmap(!), and more importantly your ever-helpful peers will head straight into freestyle road-mapping. Freestyle road-mapping is when either the hipo or the squeeky-wheel drive the road-mapping decisions. It's a disaster and really hard to curb once started. Frame the conversation and you'll be good.

Be a player-coach

Ok, you've gotten everyone aligned on the strategic goals and you've made a proposal for this roadmap cycle. It's time to let the game begin. It's time for the players, I mean decision makers, to go head-to-head and debate the features and make all the agonizing tradeoffs. Your role as coach is now complete and it's time to join the fray with your strongly held opinions and spark the debate. As the head of product you have a strong opinion, right? Remember, you're the product person and it's your job to have the best information and form opinions based on that. However, you don't have all the information so it's time to play ball and get your team to articulate their opinions so you can reach consensus on the best roadmap.

Now,  you have our permission to pop back into the coach role if the conversation is going side-ways. And if that happens, you have framed the conversation already so you can fall back to the strategic goals already agreed upon, the process agreed upon and the current topic of conversation (your proposal).'re done.

You got your folks in the room and the game commenced. You likely argued, battled and agonized over some very tough decisions. There might even have been some raised voices. That's ok. You've achieved your goal; engaged decision makers battling toe-to-toe on important decisions. You have a roadmap. Nothing left to do now except deliver on it!