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  • Writer's pictureChuck Cusumano

The Art of Avoiding Overthinking & Underthinking

By Chuck Cusumano and Jillian Broaddus

Whether you self-identify as an "overthinker" or "underthinker," the past two years have given us a LOT to think about. While circumstances beyond our control may challenge us, our agility and power to adapt will ultimately lead us to overcome! Although this blog was written in 2020, its lessons still hold true so we're re-sharing it now. Read below for a reminder on how to master The Art of Avoiding Overthinking & Underthinking to become an agile thinker, effective decision maker, and successful leader!


If 2020 has taught us anything at all, it is that anything is possible at any time. In life, in business, in that weird section where the two intersect—anything can happen at any time. As such, the term agility has been more prevalent than ever.

If you have heard the word agility tossed around in the business landscape as of late, you are not alone. It is one of those hot buzzwords that is all the rage, popping up in offices (even work-from-home offices) all over the globe.

As consultants and coaches, agility often comes up in our everyday conversations, oftentimes laced into questions that sound like, “How do I know when to make that decision?” or "How can I be sure now is the time to make that decision?”

They are great questions—simple in theory, but nearly elusive in application.

Before we dive into this, though, we need to take a brief pause and lay down some definitional foundations. Let us come to an agreement on what some terms mean so that we can better define how to tell when it is the right time to make a decision.

(P.S. If you are a regular reader of our blog, you probably already know that definitions are a major sticking point when it comes to good communication—see our blog here for more info on this topic!)

First, let us talk definitions.

  • Agility – The ability to think and understand quickly, in business terms. In other words, the ability to move and act easily and flexibly within the marketplace.

  • Thinking – A process that our mind uses to consider information or reason something out. In terms of life, it is the process used to consider data and make decisions.

  • Wisdom – The application of knowledge. In terms of life, wisdom is the knowledge and experience one has leveraged to make sound judgments.

These three words are the foundation of our ability to understand how and when to make sound decisions in our lives and in our businesses.

The simplest answer to the question “How do I know when to make that decision?” is fundamentally basic—you will make the decision as soon as you have enough information to implement a sound judgment in the time allowed.

It seems so simple, right?

Now comes the elusive part—how much information do I gather or consider and how much time do I take to evaluate?

Here is where it gets tricky.

If you gather too much data or take too much time—you are OVERTHINKING it.

If you act too quickly or do not consider all the facts—you are UNDERTHINKING it.

We like to think of overthinking and underthinking as the two ditches on each side of the highway we know as Effective Decision Making.

With this in mind—how exactly can we all navigate this highway safely without driving into either of those ditches?

We like to institute some guardrails and a sense of direction.

With the right guardrails, you can keep yourself in line, ensuring you are not getting too close to either side of the proverbial ditch. With a keen sense of direction, you can ensure that you are most likely to travel down the right side of the road when it comes to making effective decisions (in business or in your personal life).

Overthinking It—The First Ditch

Natural planners, organizers, and analytical human beings—this is more than likely the ditch you will find yourself too close to. If you identify as having one (or more) of those characteristics, it is highly likely that you will find yourself struggling to avoid the Overthinking Ditch.

Maybe you consider too many possible scenarios, maybe you think you always need more information before you process data—whatever it might be, it is possible you are a textbook overthinker.

In extreme cases, we would refer to this as analysis paralysis—in other words, it keeps you from making decisions because all the data is not in.

In moderation, you are a step or two behind where you need to be in order to be effective.

A classic example of this might include a situation like: You finally call to make the job offer to the perfect candidate for the open position at your company; unfortunately, they have already accepted another job.

Another? You are gathering more information to present a plan to your supervisor on how to improve the department’s productivity. But a coworker already presented a scaled-down version of the same idea. Now, they are the project lead that you have to report to.

Does any of this hit close to home?

Voltaire, the French writer, said it aptly this way: “The best is the enemy of the good.”

Confucius put it in a way we can all relate to, as well: “Better a diamond with a flaw, than a pebble without.”

So, how can we avoid overthinking things?

Your centerline on the highway should be agility. Set your GPS for agility.

Your guardrails should be deadlines. Limit the amount of time required or assign a deadline to consider all of the available data. Then, make a decision based on what you have—not on what you might have later.

For overthinkers, data can be a tough thing to wrestle with. Why? Because data is infinite. Time, on the other hand, is absolutely finite.

It is crucial to manage yourself within that constant of time and make the best decision with the information you have.

Optimize that decision as you travel down the highway as more information becomes available.

Ultimately, you must move forward.

So, overthinkers, remember this—your goal is agility!

Underthinking It—The Second Ditch

Spontaneous by nature, intuition follower, people-oriented, I-feel-it-in-my-gut—do these traits describe your personality and how you tend to make decisions?

You might steer closer to the Underthinking Ditch.

When you have a decision to make or data to analyze, you might predominantly rely on the feelings you have. In the extreme, we call this a Ready, Fire, Aim style of decision making.

In moderation, it is possible you overvalue the emotional side of a decision in place of the analytical side.

An example of this looks like: You have become bored and blind to the lack-luster results from one of your long-time trusted direct reports, and it is jeopardizing your team’s results.

Another one?

You already know what the outcome of a situation will be because this scenario is just like all the others you have dealt with—until suddenly, it is not.

Therein lies the overarching problem with just reacting when making decisions.

Ernest Hemingway said, “Before you react, think. Before you spend, earn. Before you criticize, wait. Before you quit, try.”

General James Mattis instructed his troops like this: “You are part of the world’s most feared and trusted force. Engage your brain before you engage your weapon.

Your centerline on the highway should be wisdom. Set your GPS for wisdom.

Your guardrail should be the brake pedal.

When an idea or decision comes to your mind, tap the brakes before you proceed—the bigger the decision, the harder you should hit the brakes.

No, you do not want to slam them to the floor—stopping all forward progress does not get you anywhere. But you should slow down enough so you do not run off the road.

What does this look like in practice?

Let's say you receive an email that you think is pretty rude or inappropriate. Pump the brakes before you respond. You do not need to react and respond at this moment.

Go ahead, write a response, but do not include a recipient in your email—leave it blank. Then, let it sit for a few hours.

When you revisit and reread, you will have a clearer head, a better idea of what you are actually feeling and thinking, and you will have more time to determine all the facts. When you slow down, you are better able to consider the discrepancies between what you think you know and what you actually know. This can help you greatly improve your evidence-based decision-making process.

Do not get us wrong, it is a great skill to be fast and first in the marketplace—but only when you are heading in the right direction. Take a few moments to get your geographical bearing straight before you take off. Otherwise, you could be going the fastest—but in the wrong direction.

The goal in business, leadership, and life should be to know yourself so well that you can adapt to the circumstances that are before you while simultaneously utilizing your best traits to achieve your desired outcomes.

In practice, this means staying on the road, avoiding ditches, and consistently improving when it comes to making good decisions based on your abilities. This should help (eventually) turn the process of driving down the right side of the road (and avoiding ditches) just like muscle memory for you.

Take a lesson from Jim Morrison and The Doors: “Keep your eyes on the road and your hands upon the wheel.”

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