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

by Keith J. Cunningham

The three most fundamental questions to ask to help get clarity about the root problem/obstacle are:

What are the possible reasons I am noticin...

What isn’t happening that, if it did happen, would cause the perceived gap (symptoms) to ...

What is happening that, if it stopped happening, would cause the perceived gap (symptom...

The machine we create and build should always help us overcome the obstacle that is blocking our forward progress and momentum, not just alleviate the pain of the symptom.

Few things are worse than running the wrong direction enthusiastically. Misdiagnosing the problem or working on the wrong priorities results in a dumb tax!

All those good ideas that turned out bad have one thing in common: unexamined assumptions, which usually take the form of a really great story.

The key to checking assumptions is to look for where I have substituted an opinion for a fact.

One of my most frequent Thinking Time questions is: “What Don’t I See?”

What none of us see are the assumptions we make about the problem we have, the solution we create, or the opportunity in front of us.

An assumption I used to make quite frequently was “lottery investing” (small investment, high probability of failure, but astronomical returns if lucky).

“If I stood here and hit a thousand golf balls, the likelihood that any of them would go in the hole is very remote. Maybe if I hit 10,000 golf balls I might get lucky and one would go in; but, you are not offering 10,000 to 1 odds. I know it’s a small amount of money and that I could easily afford it, but it’s bad odds. Stupid in small things, stupid in big things.”

spent some quality Thinking Time differentiating the facts from our emotions and fantasies.

Core Discipline #4—Consider the 2nd-Order Consequences

I use the following three questions (which I call the Power of 3) as one of my litmus tests to help me think before I act:

What is the upside? We are usually experts at this one.

What is the downside? What could go wrong? We rarely can do this one by ourselves because we are irrationally emotional and optimistic ...

Can I live with the downside? Only the pros bother to think about this one, which is why their track record of dumb tax is so much smaller than th...

We only have a choice about the decision we are about to make, not the consequences. An important decision that does not identify the possible risks as well as the probability and costs of failure is a decision with a high likelihood of creating drama.

The problem with drama is that it always costs money.

Tom’s answer has stuck with me for over twenty-five years now. “No, a double bogey is a bad shot followed by a stupid shot.”

Here it is on a bumper sticker: Thinking about 2nd-order consequences minimizes the probability of a double bogey. Mistakes are inevitable, but double bogeys are usually avoidable.

Core Discipline #5—Create the Machine

Here it is on a bumper sticker: Shoes that don’t fit are not a bargain at any price. A good idea that can’t be executed is a bad idea.

Building an effective machine or adapting the current machine implies actual activity, and that activity will be different from what is currently being executed.

Regardless of the change, management must shift priorities if the new solution has a shot at being effective.

to operate them. When you stop to think about it, a great machine that is operated by a team of B and C players who execute inconsistently and are a poor cultural fit is a machine doomed to mediocrity or the dump.

in “A CEO Should Never Delegate . . .”) 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 the people operating

Measurement is THE key to sustainability and a culture of accountability.

One tiny mistake can derail the entire process. Finding the dash of paprika that is ruining your pie requires careful thinking and close observation.

Thinking Time: The Process

My Thinking Time is highly ritualized. I have a thinking chair. The only time I sit in it is during my Thinking Time sessions. I have a thinking pen and thinking journal: I use them only when I am in Thinking Time mode. And I follow this step-by-step process to structure each Thinking Time session:

A great Thinking Time session requires a great question as the launching pad.

I clear my calendar for sixty minutes, which will enable me to think for about three-quarters of an hour and then evaluate/sort the solutions

For most of my questions, one Thinking Time session is insufficient, but focusing for more than about forty minutes is the limit of my capacity to concentrate.

(I am old-school, so I always think on paper and never the computer, where too many distractions and temptations pop up.)

Right before I start, I sip my water, scratch what itches, go to the bathroom, clear my throat, and then sit perfectly still.

To optimize the thinking process, I must lose touch with my body so that my train of concentration is totally uninterrupted.

Capturing my Thinking Time ideas while they are fresh is critical to this process.

If any of these ideas are worthy of future consideration or possible action, then I schedule additional Thinking Time on my calendar.

If I don’t take the step of scheduling it on the calendar, it stays on my “To Do” list and never gets implemented or addressed.

It is rare for me to have fewer than two or more than three Thinking Time Sessions in a week.

What we refer to as conventional wisdom rarely passes the sniff test of common sense.

If you drank the Kool-Aid of one of these “how to get your mind right and passively become a millionaire in thirty days with no money down by working four hours per week from your kitchen table in your bathrobe” best sellers, chances are you are in worse financial shape now than when you started.

vast majority of these financial self-help gurus who promise millionaire, even billionaire, status owe their financial success to selling the Kool-Aid, not from drinking it themselves.

Yet, when you think about someone you admire, someone who has achieved the success or greatness you aspire to, you will inevitably find years of practice, hard work, patience, persistence, correction, more practice, and more corrections.

You will also find a teacher, coach, or mentor who illuminates the way so you do not have to make all the stupid and obvious mistakes yourself.

When we really take a hard look at the people we want to emulate, we will inevitably find that they all started at the back of the line.

They practiced for countless hours, stayed in line, followed the advice of a great coach or mentor, overcame numerous obstacles, had some lucky breaks, committed to being a learner, practiced countless more hours, and eventually got to the front of the line.

Here is an important point: Their success was not obvious at the begin...