AMA: Asana Product Management Area Lead, Rodrigo Davies on Roadmap Planning

We rate our roadmaps and capacity plans by confidence level – so 6 months out is 70% confidence, beyond that is 50% or more. For choosing the right cadence, I think it makes sense to pay attention to the speed of your iteration cycle, your sales cycle length, and how quickly the space you're in is changing. Hopefully your iteration cycle reflects the other two!

In these situations it's important for product to lead with a customer-backed, strategic product opinion. If you aren't already an expert in what your customers want, and the strategic landscape your product is operating in, gather those insights and facilitate a conversation with leadership about a few options – with the potential benefits and tradeoffs of each. Even if the C-team is new, they'll have a sense of the business metrics they want to drive, and you can drive connecting the dots from those outcomes to the "how" in product.

It sounds like you're probably concerned about pushback from stakeholders for whom longer-term planning is highly beneficial, e.g. sales and marketing. Having a "plan for a plan" could help here – in other words, "we're pivoting and we don't want to plan more than 3 months out because we need to reach X, Y, Z milestones or answer questions A, B, C". Provide a timeframe / conditions under which you'll start to plan further out could help build trust and confidence. In the meantime, you might also need to provide more support to those functions, e.g. enablement, talking points for customers, while they have less visibility into the product roadmap.

There are a few gradations of what public means in practice – i.e. 100% open (e.g. with rankings), partially open (narrative, but not prioritized), public to customers. I think it's always important to have a version that you can easily share with customers on demand, and most companies will want a partially open version unless they're in a hyper-competitive space, or stealth mode. For 100% open roadmaps, I think it depends on the stage of your product, how you acquire customers, and how competitive your space is. In early stage, PLG, not-very-competitive spaces, this can be super helpful to drive engagement. In more competitive spaces, this risks eroding your competitive advantage, obviously, and for SLG motions, it's probably more important to put energy into your customer-facing roadmap than an open one. An open roadmap will become another channel and set of feedback you need to manage, and that audience might not always align with the customers you're trying to acquire.

Sales having a strong opinion about what customers want and being driven to advocate for it is actually a powerful asset! It sounds like where you're struggling is this energy is being directed into specific solutions. Try making time before solutions become an "ask" from sales to do upstream discovery of what they're hearing and are excited about, and work with them to frame their goals as customer problems rather than "build this specific thing". It could be as simple as changing a roadmap phrasing from "Build X" to "Solve Y problem by exploring solutions such as X". If this is a new muscle, it'll probably take some time to build up trust with sales that you'll execute on something that customers love just as much (or more) as solution X, and that you're not afraid to ship X as described, if that's the best option.

It depends a lot on the team, of course. There should always be a one-page version that any interested stakeholder can consume, but that won't answer all the questions some teams will have. I've found doing live Q&As with teams or groups of teams during roadmapping can be super helpful, to find out what people care most about. From there I can decide whether additional artifacts would be useful, and what shape they need to be. Making lots of shareable artifacts ahead of time (beyond one-pagers) can sometimes be wasted effort.