In the realm of technology, uncertainty is the name of the game. It's a reality. We can pretend that it's not, but all we're doing is pretending.

Sure, a staff-member or an external firm may tell you how a project will happen or what sort of investment a product will need, and how it will all go down. You may even get a great plan, made with thoughtfulness and integrity. 

The problem is, the plan doesn't know 90% of the important details that will emerge to affect the road ahead. Before you're in the game you're just guessing, but once you're in the game you can adjust to the realities on the field. It's suddenly much clearer where the bottlenecks are, where the fires and opportunities are, and which battles will help you win that day and live to fight the next.

Countless major and minor adjustments of landscape will occur, from staffing issues to strategic puzzles to external expert availability to valuable feedback coming in from users. New, impactful opportunities will reveal themselves, and finish lines will turn out to have actually been halfway points. That's not because of some sort of undisciplined "scope creep," it's because someone spotted a strategic opportunity or two (or ten) along the way, and priorities were shifted appropriately. 

As new information comes to light your priorities should adjust. Would you want to ignore all of these precious insights simply because they might send you in a direction that wasn't outlined in the original plan? All of these things are going to affect the plan. They should, that's the whole point. And your beautiful plan doesn't know this stuff yet. It can't.

To be successful with technology, we have to get to agreement that uncertainty is the name of the game. The name of the game is being as smart as possible navigating an environment that is always in flux.

Yes, our organizations need estimates and budgets, and for good reason. So let's do our best to make smart guesses about what's to come. But the goal should not be to stick to those guesses, or to pretend that they should win any arguments about what to do next. The goal should always be to make the best choices about the most strategic and impactful use of time and resources given the landscape we face today.

And when we get information that tells us that the guesses should be updated, we need to update them, for clearly articulable reasons and without apology to bosses, boards, partners, or staff. Why stick to a best guess from three months ago simply because it was our guess? It's antithetical to the entire approach, and to common sense. It's a recipe for underwhelm, or missed opportunity, or outright failure. It's shooting ourselves in the foot.

So if we can't have the security of relying on a plan, then what can we rely on?

Our fundamental belief is clear, and the evidence bears it out. You must find smart, capable people and charge them with stewarding your technology. You must protect their remit, invest in them, and help them navigate their ever-changing landscape with intelligence and integrity. 

This is the whole basis of lean, agile work. At any given time, both your product team and your consultants should know their compass headings and the next hill they're going to take. But once they've taken that hill, any number of things will have changed. And their job will be to make the best decisions possible based on the latest updated intelligence they have.

What a superior path that is to a successful outcome, compared to picking the plan that reads best at some given time and pretending we can somehow just close our eyes and stick to it.

We need to ask ourselves as leaders: Do we build a team that is good at handling uncertainty? Or do we build a team that is good at pretending it’s certain.