Why We Need Question-based Planning More Than Ever

Jack Ricchiuto
2 min readMar 25, 2024

We are not the first era with complex challenges, nor will we be the last.

We inhabit an era where the world is more connected than ever. This is a two-sided coin. On one side are more possibilities for collaboration than ever, and on the other side we have more complex challenges than ever.

We dream of a world where we can solve complex problems together so we leave the next generations with a world better than we found it.

Making this possible will take planning that works. This is planning that makes us smarter together, aligns us quickly, and brings out our best.

Not every planning model is designed to do this. Question-based planning is. If we want to solve complex challenges together, we must discover that it’s our planning models that make solutions more or less possible. We have to stop naively believing that who’s around the table or at the head of the table is more important than the planning model we use to be at the table.

Complex challenges are unfolding networks of uncertainties. Uncertainties include unknowns, contradictions, disruptions, constraints, and risks. Our penchant for certainty compels us to solve complex challenges. Questions have the ability to turn uncertainties into prime planning assets. Planning is turning uncertainty into new realities.

Planning that doesn’t work is assumption-based.

Until they’re transformed into new, actionable questions, assumptions divide us and maintain the status quo. They do not have the power to help us understand much less solve complex problems.

The “solutions” they create cause more problems than we had originally. They are the basis for the kinds of moral righteousness and superiority that prevent the solving of complex problems. They do not make us smarter together, align us quickly, or bring out our best.

People who practice and prefer assumption-based planning that doesn’t work are not bad or stupid people. There is nothing wrong with them. It’s their planning model that keeps things the same or makes them worse — even if they argue they are “for change.”

Question-based planning get all of us on the same side of the complex problem-solving table. Assumptions align those of us who share these assumptions. Questions can be shared by everyone.

Question-based planning works because it operates from zero assumptions. Working from assumptions is the prime planning flaw because assumptions prevent us from more deeply understanding complex problems. They also prevent access to new possibilities, which are only accessible through new, actionable questions.

In question-based planning, we solve complex problems one question at a time. Questions have this extraordinary power.

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