Four Questions to Help You Think Bigger About the Future

Provocative questions are powerful. Here are four tried-and-true queries that help groups think proactively about their futures.

1. Thinking back, what big ideas or opportunities did we miss? What happened, and what can we learn?

Swings and misses have a lot to teach us. So do missed opportunities.

This is a great question for groups that have a lot of experience or longevity together. They know the history and the players. They know what was missed and why.

The first part of the question is just an appetizer; the second part has the insights you're looking for.

Why this works: Everyone wants to be remembered for what they did rather than what they didn't or couldn't do. Framing this question as a reflection on history pulls past lessons into the present, so leaders can make future choices with greater wisdom.

2. Imagine another organization made it their business to put you out of business. What are the first things they'd do to kick your butt?

You can use this for cities, companies...even teams or departments.

Why this works: This question gives you permission to admit your soft spots or weaknesses and raises the temperature on taking action now.

I've used this question many time in my own business. It always provides immediate clarity on things that have been low-key nagging me.

3. We are on a journey from X (current state) to Y (future state). What are X and Y?

Bryan and I asked this question in a meeting with four prospects from the same coastal community. We got four creative responses that all pointed to a shared truth: they were on a journey from a once-proud but aging brand to a reinvented place with dynamic, new swagger.

Why this works: Until people SAY IT OUT LOUD, their worries about the current state seems...impolite. But if you give people a chance to state their worries--alongside what they believe is possible--it creates group therapy and group hope.

4. What old habits or beliefs do we need to let go of to reach our potential? What exciting seeds of the future do we see starting to take root?

My wife is a tremendous gardner. In late fall every year, she clears the garden of old growth, spreads compost, and protet the soil so that next spring it's ready for a new cycle of growth.

Why this works: This question is a gardening question; it asks what has to be cleared away and turned into compost so that a new healthy cycle of growth can occur. The first part of the question is about letting go. Most of know what we need to let go of - the grudges, bad habits, or rivalries. It can be hard to let go - but sometimes it's easier if we can see how letting go can enable dynamic new things to come forth.

Please let me know if you use these questions and how they work for you.