Does it make sense to use quarterly format for roadmaps? Do you do capacity planning for roadmap items that are more than 6 months out?

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!

We all inherently understand that the farther out you plan, the greater the uncertainty. This was also one of the key themes in the Agile development methodology. But I don’t believe I’ve ever heard someone explain the implications of this in a practical way for product managers.

Some businesses may require 5-year financial plans for product investments. Sometimes called LRPs for “long range plans.” These are bullshit as forecasts, but the exercise is useful as a check that this new product could be a profit-making business if it succeeds. E.g. if you can’t spin a credible story that grows the business to a revenue size and profit margin that your business would be interested in, then you know not to waste your time in this endeavor.

What I like to do for pre-PMF products or significant pivots to established products is 

1. Make a 2-3 year vision/loose plan: This is about painting a picture of a future product and business that are exciting and relevant to your customers and company. This will also engage your team members and stakeholders and help you align with your leadership.

2. Define a successful next year: Sync with company leadership or investors on what success for the next year looks like. E.g. "If we can achieve XYZ, we’ll be happy and keep investing/maybe grow our investment."

3. Make a concrete roadmap for the next 3-6 months: You need clear milestones with exit criteria, sound goal metrics with targets to hit, and prioritized and sized projects. Ideally you'll even have forecasts of the metrics improvements you can expect from your major projects.

These 3 artifacts will leave you with an inspiring vision for 2+ years to attract talent and motivate teammates and stakeholders, a clear definition of what a successful year of product advances looks like, and a concrete plan to hit the next set of milestones and goals. They also avoid waste in planning concrete milestones far ahead that will likely be abandoned as you continue to learn and adapt to your market.

More on roadmap durations and goals:

• Goals: On my teams, we plan 6 months at a time, and take on hard numbers goals (50% chance of success) for each 6-month period.

• Certainty: I encourage PMs, engineering managers, and senior folks on the team to ensure they have really clear roadmaps for the first 2-3 months, and then it’s OK to have some unvetted ideas in months 4-6. This serves two purposes: it encourages goals that are hard, ideally hard enough the team’s not sure that they can hit it. It allows the team to keep thinking creatively, keep learning, and swap in better projects whenever they discover and define them.

• Capacity planning: If you have hard dates you have to hit (e.g. major marketing moments, hardware device releases, consumer holidays, etc.), it’s an important check. If you ship updates regularly (monthly or faster), capacity planning usually isn’t that important because the team can just continually strive for their goals with the best projects they can think of.