I’m a fan of Oblique Strategies for triggering a new perspective when I get stuck. To me this method brings active questions to trigger better thinking.
This practice comes up for me frequently in product management when working on both short and long views of a roadmap. As part of any decision making process, whether by myself for reflection, or in a team working on a product change, I might ask something like:
What is the end result for our customers?
Where are we going in the long term?
The purpose of active questions, like Oblique Strategies, is to trigger more questions until you get a better answer. A truer answer. An honest answer. To find the why is to find the signal that drives everything else forward.
Who is it for?
How will they understand it’s for them?
How will we know if it’s a success?
What do we expect to see change?
How are we measuring it?
What would be a surprise here; something that we don’t expect?
Have we considered doing the opposite?
Who has the most to gain?
What’s the context?
What questions do you ask to find the why?
The Sensible Leader 