July 23

“If you get stuck, draw with a different pen. Change your tools; it may free your thinking.” – Paul Arden

It’s bound to happen sooner or later. No matter how skilled you are and no matter how well you’ve prepared, you’re inevitably going to find yourself stuck on a tough problem without a clear path forward.

It’s tempting in these circumstances to keep your nose down and continue cranking on the problem. The problem with this method is that you may be digging yourself deeper into an existing rut.

Sometimes it’s valuable to have a set of questions at the ready to help you re-frame, shift, or view the problem through a different window. Below is a set of questions that have been used in various situations to jog new creative thoughts about stubborn problems. The questions can be used on your own, but are especially valuable in the context of a team.

We have to be willing to immerse ourselves in the process in order to get to the deeply valuable ideas that reside just on the other side of stasis.

Choose a project you’re stuck on, and ask:

Is an assumption in the way?

What is the worst-case scenario?

Could I do the opposite?

How can I thrill the end user?

What am I afraid of?

Do I understand why?

Where else has something similar been done?

What is expected and why?

Who has something to lose?

Who is the enemy and how do we foil them?

Who could solve this problem with ease, and how?

How would my favorite super hero do it?

How would my favorite movie character do it?

Could I change the medium?

Could I ask the question differently?

How would a 3rd grader approach this problem?

What question do I need to answer first?

Is there a resource I’m lacking?

How would I describe the problem in three words?

Are there sub-problems to the main problem?

What’s the world like once the problem’s solved?

Who can I call for help?

Can I create a metaphor for the problem?

How would I start over?

What’s the primary block and why?

Refuse to remain stuck. Ask new questions to spark new insights. 

Question: Is there an assumption you’re making that needs to be challenged?

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