September 5, 2024 | By David M. Wagner

Imagine, six months from now, you know that the project or initiative or problem you’ve been worrying about has gone completely wrong.

Now ask yourself – what are the possible reasons for that failure?

This thought exercise is called a “premortem” – a tool for identifying risks and issues before they occur. (Freakonomics radio featured postmortems in an episode about succeeding at failure last year).

I love questions like this because they force us to reframe situations in new ways.

The right reframing can bypass mental roadblocks to our creativity.

Using questions to unlock new ideas is an inquiry-based leadership technique you can use to inspire teams, coach individuals, and even jumpstart your own creativity.

Here are five of my favorite questions to reframe challenges and generate new ideas.

1. If you could magically change any one thing, what would it be? Would that fix everything? In other words, is what’s bothering you the real issue, or just a symptom of the root cause? Getting to the heart of the challenge helps focus on realistic ways to address the right problem.

2. What does success look like? How will you know things are better? Getting specific about tangible changes you’d like to see will clarify your goals. It can also reveal suddenly-obvious steps to take (e.g., knowing that you want funders to increase their giving suggests you’ll need a campaign to make those asks).

3. What would someone (or an organization) you admire do in this situation? Imaging how someone else would handle a situation removes you – and your perception of your limitations or constraints – from the equation. You may discover new possibilities that, on reflection, you can make happen.

4. What would you do if there were no possible downsides? Removing fear, uncertainty, and risk helps reveal your true preferences, as well as what’s holding you back. Take this as permission to explore whether the obstacles you envision are real, and if so, whether there is a way around them.

5. Imagine that six months from now, everything is better; looking back, what made that possible? Okay, I cheated a bit and turned the premortem question above into something with a positive outlook. Removing the uncertainty about if things will work makes it easier to imagine how things will work. You don’t even need to know all the steps between here and success – finding the first move to make can be enough to get you unstuck.

Whether you, your mentee, or your whole team are wrestling with a big challenge, asking the right question helps you reframe the issue. Finding new ways of looking at the situation will remove mental obstacles to your creativity and unlock new ideas.

I use questions like these when I facilitate strategic planning, coach leaders, and help nonprofits tackle wicked issues. If you’d like a hand working through your biggest challenges, set a free consultation today.