I really like Basecamp’s concept of “Hill Charts”. The gist of it is that each project we work on has two distinct phases: a “figuring it out” phase and a “making it happen” phase:

To quote from their post about it:

First there’s an uphill phase where you figure out your approach. You have a basic idea about the task, but you haven’t figured out what the solution is going to look like or how to solve all the unknowns.

Eventually you reach a point where there aren’t any more unsolved problems. That’s like standing at the top of the hill. You can see clearly all the way down the other side. Then the downhill phase is just about execution.

“Figuring it out” is full of uncertainty, unknowns, and problem solving. “Making it happen” is all about certainty, confidence, and execution.

I bring this up because one of the issues with quarterly planning cycles and committing to due dates on that cadence is that teams are often asked to commit to dates during the “figuring it out” phase. There’s a lot of uncertainty and unknowns, so teams have to make best guesses. The problem with this is that these do not reflect what Cagan calls “high-integrity commitments”:

The key is to understand that the root cause of all this grief about commitments is when these commitments are made. They are made too early. They are made before we know if we can actually deliver on this obligation, and even more important, if what we deliver will actually solve the problem for the customer.

So what inevitably happens is that, for a lot of projects, the date that teams provided “slips”. I believe this language matters, and I think by framing it this way an org tells teams they did something wrong. But the irony is that in the majority of cases, if teams move a date after they reached the “top of the hill”, they are doing the right thing for the business. They are saying that they have now figured out all the unknowns and uncertainties, and they are ready to make a high-integrity commitment. Again, here is Cagan:

So the compromise is simple. The product team asks for a little time to do product discovery before commitments are made, and then after enough product discovery is done to consider the risks, we are willing to commit to dates and deliverables so our colleagues can effectively do their jobs as well.

I think it’s important to encourage behavior that does the right thing for customers and the business. The right thing would not be to try to cut corners to meet a date that was committed to during a “figuring things out” phase. I also don’t believe the right thing is to inherently communicate to teams that moving a date once they reach the top of the hill means they “missed” a commitment.

I think we should be very clear about the nature of commitments when we make them. What is our confidence in our dates? Are we still figuring things out? Or are we at the top of the hill and ready to make a high-integrity commitment? The health of any Product org can be improved if we say that it’s ok to communicate what we think we can accomplish early on in the quarter, and move to high-integrity commitments once teams reach the top of each project’s hill.

I was recently asked by a colleague to write up our team’s reasoning for using a Now/Next/Later roadmap to plan our work (instead of quarterly/annual roadmaps with dates). If you already use Now/Next/Later nothing in here will be new to you, but I thought I’d share what I wrote for this internal document in case it’s useful to anyone hoping to make this shift as well.

We use an adapted version of a Now/Next/Later roadmap to plan our work. You can read more about this approach in Introduction to Lean Roadmapping by its creator, Janna Bastow. In short, here are the guiding principles for using this roadmap and why it is effective:

• Deadline-driven development is fraught with issues that make it a fairly ineffective way to plan delivery work. This includes:
  • Long-term priorities frequently change based on new data and developments, so any planning past a few months out is mostly fiction and rarely happens as planned.
  • Deadlines are often set without input from the delivery teams who are building the product, which makes estimates inaccurate and difficult to attain.
  • Because deadlines are often arbitrary, delivery teams have to make quality tradeoffs to meet the dates, which introduces unnecessary technical debt into the system.
• Using a Now/Next/Later approach helps delivery teams know what is most important to work on, and what is coming down the road.
  • “Now” means Now–it is literally the work that is in flight. This work should be limited to 1–2 projects per team to ensure effective delivery.
    • Changes to “Now” should only happen in the rarest of occasions so as not to interrupt work in flight.
  • “Next” means anything from 2–8 weeks from now. This is work that is planned and ready to go as soon as a team becomes available. It has been spec’d and scoped, and everyone agrees it’s the next important thing. We limit not only Work In Progress (Now), but also Work in Next, so that there are not too many priorities vying for attention.
    • Changes to “Next” should happen infrequently since the work is planned and the team will be ready to go at any moment.
  • “Later” means anything from 2–6 months from now. This is work we believe is important to be prioritized, but it hasn’t been fully spec’d and scoped yet.
    • Changes to “Later” can–and often does–happen whenever new data becomes available that makes us shift priorities. This is expected and encouraged, until the project moves to “Next” where it gets locked in and fully spec’d.
  • We cheated and added “Much Later”, which lists things that we think will be 6–12 months out. The likelihood of these projects changing are high, but it is good to have a long-term view on what we believe, with the current information we have, will be important for the business and our customers to work one.

We do acknowledge and recognize that delivery dates are important. We prefer to work with high-integrity commitments, which are dates that delivery teams commit to once they have had a chance to properly scope out a project (which sometimes means getting started without a completion date set).

The teams are accountable to these dates because they have been involved in setting them, and though they can change based on unknowns, these changes should be infrequent.