Brutal Questions
Big Business
Brutal Questions
Brutal Questions
Sole Trader

Brutal Questions
A tool for the brave! Confront the brutal questions associated with your business

The big idea

Confronting the brutal questions (and facts) is an approach developed by Jim Collins (2001, 2009) from The Stockdale Paradox, which highlights the challenge of holding unwavering hope at the same time as confronting the brutal facts. Admiral Jim Stockdale, was a United States military officer who was held captive for eight years during the Vietnam War. As Stockdale told Collins, he never lost faith during his ordeal: “I never doubted not only that I would get out, but also that I would prevail in the end and turn the experience into the defining event of my life, which, in retrospect, I would not trade.”

The paradox is rooted in the fact that, while Stockdale had remarkable faith in the unknowable, he noted that it was the most optimistic of his fellow captives who did not survive the ordeal. They could not contemplate the brutal reality of the situation they found themselves in.


The purpose of this tool is straightforward: it is to help you adopt Stockdale’s approach and balance hope with the brutal facts. There is no doubt that we are now in an economic maelstrom, which follows a long period when arguably the creative and cultural industries ‘never had it so good’.

The Tool

This is not so much a tool as a series of reflective prompts to help you ask the brutal questions and confront your brutal facts. If this set of questions is not brutal enough for you, feel free to amend or add! The tool can be used on your own or with your team if you have one. As they are reflective questions, take time to think about them.