The art and craft

Smart questions are questions that help you reframe situations, connect people and refocus your efforts in useful ways.

We all use versions of these questions, but we generally don’t learn them in any systematic way. The art and craft comes from paying attention to which questions are useful for what, when, and with who.

For now it’s simplest to think of them from three perspective

1. Navigation questions

These are questions to help make new sense of the messy situation and decide where to focus. At a practical level they boil down to questions about:

  • Where we are e.g. What are we solving? What’s needed? How do we know?
  • Where we’re aiming e.g. What’s our ambition? What would ‘good’ look like? How will we know we are there?
  • The journey e.g. How might we get there? What’s possible? How do we start?

2. Connecting questions

The challenge with navigation questions comes when people disagree about the answers. Splitting them out helps, but getting real connection between people needs more. Connecting questions are about what matters to people, and why.

First, listen for perspectives that seem confusing, and ask ‘can you tell me more about that?’. Then, once you have more clarity, at some point ask ‘what is it about X that makes it so important to you?’. The art is not just using the questions – it’s caring about the answers enough to find connections between them.

3. Intention questions

For the navigation questions and connecting questions to work, you need to resolve a personal paradox. On the one hand you need your own opinion and perspective – a starting point for entering the discussion. But you also need to hold it lightly, to be genuinely curious about other opinions, and open to changing your mind when new information appears. It helps to think about your intention as two questions: ‘What do I hope to get from the discussion?’ and ‘How do I want to show up and contribute?’. Being clear about intentions before you start generally helps you to navigate how those things get resolved.