The Road Less Stupid by Keith Cunningham

The Road Less Stupid is a business book that provides tools for thinking and effective decision-making. The author, Keith J. Cunningham, emphasizes the need for thinking, planning, and minimizing risk to achieve and sustain success. The structure of Thinking Time will enable you to minimize reacting emotionally and defaulting to the most obvious “best idea” available in the moment.

The main themes of the book are:

• Thinking, planning, and minimizing risk are essential to achieve and sustain success.
• Emotions and intellect work inversely. When emotions go up, intellect goes down.
• The importance of creating a system that takes you from Point A to Point B or removes the obstacle and maybe also closes the gap.
• The need to check assumptions and differentiate the facts from the story.
• The five core disciplines of thinking: find the unasked question, separate the problem from the symptom, check assumptions, create the machine, and set a consistent time to just think.

Useful takeaways from the book include:

• Identify the potential risks, the probability, and costs of failure for any major decision.
• Consistent execution requires dashboards, processes, best practices, standards, metrics, and accountability to measure the critical drivers, monitor the progress, reward the success, and coach/train people operating it.
• Use Think Time, a dedicated time to focus on important questions and come up with an outcome.
• Create a question that will result in clarity and generate better choices.
• Identify the real obstacle that is blocking your progress.
• Differentiate the facts from the story.
• Don’t live in the gap.
• Do some independent thinking instead of following all the sayings.
• Mistakes are inevitable but making bad moves after stupid moves can be avoided.
• Set a consistent time to just think.

What I Liked

I liked how specific this business book is. There’s not a lot of theory – but day to day tactics.

What I Did Not Like

Ok, the author definitely thinks a lot of himself. There’s nothing wrong with that (it pushed him to write a useful book!) but the book would be better with a little less personality.