Book Report: The Road Less Stupid: Advice from the Chairman of the Board

This is a review of the book “The Road Less Stupid: Advice from the Chairman of the Board” by Keith J. Cunningham.

Read this book if:

• You’re looking to improve at managing your business
• Are interested in problem-solving as a business
• You want to improve your business

While I have issues with the title, the book does contain a lot of wisdom. I always enjoy reading these types of books, not because of the novel bits, but because it’s interesting to see my own beliefs echoed back from a different perspective.

What I particularly appreciated was that Cunningham convinces the reader they are the expert on the business and simply need to do the proper thinking and doing to achieve success. It’s a subtle thing too. Each chapter he poses several “thinking time” questions that are designed to help facilitate knowledge bubbling up. It was an implied reinforcement that anything is achievable if you’re willing to put in the work.

This book covers a vast array of topics, all related to some aspect of business. Primarily from a leadership perspective. Most of the topics can be extrapolated for personal use and small businesses. I think there were four chapters out of the 48 that I didn’t take notes on.

Thinking time

Cunningham introduces the concept of “Thinking Time” early in the book¹. It’s a process where a person deliberately thinks on a question for an hour. He provides a structure and process that has helped him be effective in this practice. There are tactics on how to rearrange the question to help elicit further knowledge from yourself. I gave this a go, and it does work, but like anything, it will take practice to make it consistently effective.

These thinking time questions revolved around five core disciplines of thinking². He goes into pages of detail on each of these, which is necessary to fully understand the approach.

1. Find the Unasked Question
2. Separate the Problem from the Symptom
3. Check Assumptions
4. Consider the 2nd-Order Consequences
5. Create the Machine

He makes the point that a thinking time question may require multiple sessions as the topic advances through multiple disciplines. I enjoyed seeing how his mind works and how he approaches complex problems. After all, we all face areas of indecision and uncertainty. This provides Cunningham’s approach on how he moves forward.

Undelegatable roles of a leader

I enjoyed Cunningham’s take on how a leader should delegate in that he inverts the concept. He doesn’t refute that delegation is necessary, but a leader has specific responsibilities that a leader must do themselves³. The terminology is directly related to the vocabulary of the book, so to best understand it, you’ll need to read it in full.

1. Clarify where you are and where you’re headed.
2. Identifying the gap and the obstacle(s).
3. Design the plan and the machine to move forward.
4. Allocating resources.
5. Cultivating good people.
6. Building out the organization chart.
7. Creating the culture.

Culture tends to be a recurring theme in the book. I appreciate the tangible advice Cunningham includes. In this chapter it centers around the fact that to create the culture, you must hold everyone, including yourself, accountable to the culture.

Goal setting and making plans

Chapter 16, “Dreams and Demand” covers the process for setting goals and making plans. The chapter includes a long list of common pitfalls when it comes to goals. One of those pitfalls is that the goal setter frequently lacks accountability to achieve the goal. It’s much easier to stay on track when you can rely on someone else to hold you accountable. Another is that it’s easy to be judgmental about our current situation and consider everything to be bad. There’s a lot that is going right, and Cunningham points out that being judgmental about your circumstances is an easy way to be unhappy.

The last thing I want to mention from this chapter is the idea that you need to be flexible. Over time, opportunities will present themselves in unexpected ways⁴. Being open to these possibilities and not rigidly sticking to your plan can help you tremendously on your journey.

Smaller tidbits

I can’t include everything that stuck out to me, but I’m still going to include a bunch! Below is a list of smaller things that I’m trying to commit to my daily processes and thinking.

• Don’t take advice without thinking on it. Mentors can help guide you as long as they recognize they don’t know everything⁵.
• Culture change requires hard and real consequences⁶.
• When you make a mistake, take the time to learn from it⁷.
• Don’t let systems and processes get in the way of adaptability, flexibility, and spirit⁸.
• Everything requires maintenance to avoid decay⁹.
• What gets measured gets done, what gets measured gets managed, and what gets measured and reported on can improve exponentially¹⁰.

Should you read this book?

I found this book insightful and thought-provoking. I mean, there are hundreds of thinking time questions, so how could it not be! Beyond that, Cunningham does a good job of making you confront how you operate and think.

I think it’s worth reading if you’re interested in revisiting your leadership or open to other ways to operate an organization. I believe it will be an excellent reference resource to refer to as I move forward.

Interestingly enough, the last thought I want to leave you with wasn’t written by Keith J. Cunningham, but instead by James Michener¹¹. I include it because the book is more than just a business book. It makes you reflect on how you operate as a human as well as your organization.

“The master in the art of living makes little distinction between his work and his play, his labor and his leisure, his mind and his body, his information and his recreation, his love and his religion. He hardly knows which is which. He simply pursues his vision of excellence at whatever he does, leaving others to decide whether he is working or playing. To him he’s always doing both.”