We expect and long to have the past back and drive what’s next and distrust the present, which is why we create roadmaps (and backlogs). But they create a feeling of debt. They can become order-dependent, making it hard to drop things if things get stuck, and they are often inflexible once they are shared. They treat strategy as a problem in deduction, which assumes anything worth knowing is already known. The hope is to create some kind of a prime radiant. It says, planning is one thing, executing another, and discovery has nothing to do with it.
Roadmaps, even described at higher altitudes, build up accumulated variance, which rises proportional to the square root of the time period. This means slippage rises exponentially with duration, e.g., a roadmap twice the duration can experience 16 times as much slippage from the original plan. Why waste time on it when each step knows more than all our thinking?
In ever-changing environments, prioritize adaptability over rigid planning, refraining from commitments extending beyond a 50-day timeframe. We figure things out as we go. It’s as simple as that. Continuous adjustment. We’ll do that regardless, with or without a plan or target.
There’s no nav in software product design and development. There are phases. You do something, and then you see the next step. It is incremental, not monotonic. You need to be ready to make decisions at any point in time.
Don’t plan all at once; plan along the way. Tell people what to expect more frequently, versus imagining and making bold guesses. You can make decisions as you go. You can make things up as you go. It’s not a scary thing. You’re still making decisions. You’re still being thoughtful and thinking things through, and you can let yourself do this more frequently. There’s nothing magical about doing it all at once…in the past. We can also avoid thrashing around by locking in what we wanna do for the next 30 to 50 business days. This lets us see meaningfully large and important things through and ship software on the regular.
Can you think of ALL the right work in advance?
Instead of suitably detailed long-horizon plans/forecasts, specify the end state, its purpose, and the minimal possible constraints. Be sure to address the following two constraints to stay focused on a distinct path when developing new products:
- State the transient trends and the enduring truths in your vertical, and how the business model works.
- State what the product will be more and less about and why ().
- Help your team learn how to think, and not what to do.
Don’t plan, prepare. An artifact that doesn’t tell you what’s ahead, but something that teaches you how to act when the future arrives. A future you hopefully co-create.
Counterintuitively, sometimes—especially in creative problem-solving endeavors—modeling the messiness of reality requires being imprecise or approximate. Imprecise wiggle room often better reflects what’s truly happening than basing conclusions on a precise but false premise.
Learn to accept the discontinuity between artifacts as plans and the work itself.
“Feel” as an outcome of understanding is a much better guide at this altitude. Just because you cannot see far out from where you are presently doesn’t mean you aren’t on the right path or not doing something radically important. Stay present. Do what you think and feel, and not only do what you have thought. Why should I defer to the ‘best guess’ of my past self when I’ve got better eyes now? Before was just now, then. Why not look at now, now? That’s when we know the most about a given thing anyway.
We must not live ad interim and look upon the present as something to be put up with while it lasts, serving only as a means to our goal.
Progress and flux. The defining properties of life itself.
Instead of using artifacts like roadmaps, put a narrative together about the vision. Speak to what is forever (what won’t change), what needs to change, where to act given the leverage you have, what could cause this vision to fail, and why you are here.
Then, empower talent (your teams) to navigate through customer strategy with coherent action, act, and back-brief on outcomes. We need strong systems to ensure that the many small economic decisions have an impact. This is where you get the biggest bang for your buck when you begin to move fast, i.e., strategy (*intentionally directed actions*) moves downstream to the local levels…the teams.
No matter how tempting it is to believe in it, the distant objective cannot guide us to itself — it is the ultimate false compass and just eats up time that could be spent on real things.
Don’t outsource decisions to ghosts of past reasoning and think you are improving by applying post hoc rationalization. You’ll always know more now than you did then. Planning is not about freezing decisions in advance—it’s about preparing to *decide better* when the moment comes. The future doesn’t need a blueprint. It needs a team equipped with eyes open, minds sharp, and hands ready. That’s how we get real traction: not by remembering what we thought, but by acting on what we *think*.
(Consider incorporating a *portfolio allocation* approach, as seen in the link below.)
2. Prioritizing Under Highly Variable Conditions