An Executive Psychologist’s Top Six Tips for Making Better Decisions

As an executive psychologist, I am privileged to work with CEOs & VCs on optimizing their health & performance. However, as a general rule of thumb, I try to stay away from giving advice, since my stance is to not tell people how to run their lives and businesses (in fact, I’m trying to foster independence).

As a former startup CEO/executive myself, of course I’ll give advice if I think someone’s making a clear mistake or if directly asked. But most of time, my job is to give people evidence-informed frameworks for making better decisions, which they can internalize and later use in any situation. Here are my top six tips for making better decisions:

1) Decide within the same amount of time it would take to undo the decision.

Photo by Samantha Gades on Unsplash
Photo by Samantha Gades on Unsplash

Decisiveness is a competitive advantage in business and in life, and so is a sword that should be honed sharply. That being said, major decisions are not to be decided impulsively just for quickness’ sake.

In order to avoid procrastination, it’s important to set a time limit to make the decision. How long should that time period be? I recommend basing it on the chance of failure (something with 10% odds of success need to be considered more slowly than 90% odds), and how long it would take to undo the decision if necessary.

For example, these days, marriage can unfortunately be a risky proposition, with approximately half ending in divorce or separation. Undoing this can be a fiscally expensive and drawn-out legal affair (especially with children involved), so understandably requires serious reflection. On the other hand, the median job tenure for employees who are boomers vs. millennials has dropped from 10.1 to 2.8 years. Thus jobs nowadays can be considered a “tours of duty” that can be left and replaced relatively quickly in the current bull market, and thus can be decided on more quickly.

2) If you can’t decide, the answer is no.

Image for post
Image for post

When it comes to making decisions about people, listen to your gut AND your loved ones or colleagues. Intuition is basically unconscious pattern recognition, and is an effective tool for deciding whether to trust people given enough experience (e.g. I have seen thousands of clients and thus have become pretty good at spotting pathology).

Unfortunately, sometimes intuition is heavily tainted by other unconscious issues. For example, some people unknowingly seek relationship partners who treat them poorly if their underlying core belief if they are fundamentally undeserving or unlovable. That’s why it’s important to listen to loved ones as well when it comes to relationships or colleagues when it comes to hiring. If they’re spotting major red flags that you are too emotionally blinded to see, it is worth taking into consideration. Life is short — don’t pursue relationships with people you don’t resonate with and your loved ones or colleagues don’t get along with.

However, when it comes to deciding to attending events or purchase things, people are susceptible to “FOMO” (Fear of Missing Out). This is exacerbated by the new social media culture in which everyone portrays living their best life in order to signal social status and desirability. In reality, if you’re not compelled by an event or object (Derek Sivers’ HELL YEAH! or No motto), saying no when indecisive will often save you time and money (Marie Kondo’s, “if it doesn’t spark joy, throw it away”).

3) If two decisions seem equally difficult, choose the one that is more painful in the short-term.

Image for post
Image for post

According to Naval Ravikant, when presented with two choices that seem equally difficult, our perceptions are distorted by wanting to avoid pain. The two decisions SEEM equally difficult, but the one that is more painful is probably actually easier (in respects other than how painful it seems), so we overweigh its difficulty as a result. Paradoxically, the more painful path is often easier in the long-term.

According to Acceptance & Commitment Therapy (ACT) principles, avoiding pain is actually the root cause of most psychological suffering. Thus, we should try not to avoid pain as much as possible IF pursing a path that involves pain means getting closer to our values (who we want to be) in the long-term. It’s important to remember that making decisions that are in line with your values does NOT guarantee emotional happiness (though increases the probability anyway), but DOES increase satisfaction/contentment. Satisfaction is more of a cognitive appraisal that is achievable and stable, unlike a fleeting emotion like happiness or passion is unsustainable at all times.

4) Before making the decision, be as realistic as possible. After making the decision, be as optimistic as possible.

Image for post
Image for post

Decisions should ideally be made as realistically and rationally as possible. One way of instigating this is practicing intellectual humility. Elon Musk, one of the greatest entrepreneurs of our generation, said regarding running a company:

“You should take the approach that you’re wrong. Your goal is to be less wrong.”

However, once you make the decision, particularly if it is difficult to undo (starting a company/fund, getting married/having children), you should purposefully put the blinders on and be as committed and optimistic as possible. This also influences performance. According to my classmate/colleague Adam Grant, in insurance sales jobs with high rejection rates, optimists sold 37% more than pessimists over a 2-year period and were half as likely to quit in their first year.

5) Once made, don’t second-guess your decision constantly.

Image for post
Image for post

Since I have a speciality in treating with anxiety disorders and I work with executives with very high stress jobs, they tend to be on the anxious side/spectrum. This can lead to not only indecisiveness, but second-guessing the decisions once made.

From a behavioral perspective, second guessing is an avoidance behavior, because it’s triggered by a stimulus (anxiety), which leads to reassurance seeking (to suppress the anxiety), whether internally or externally (reflecting on/researching the decision again, or asking a colleague for a second opinion).

In order to break this association, I recommend that reflections should be scheduled ahead of time, so that they’re not triggered by any emotion, but prompted your calendar. I recommend using the Keystone Habit method to set up reflection times that are as brief as 4 minutes.

In reality, if there’s obviously urgent or important new information that has come up (e.g. your business’ sales are tanking and you need to pivot), obviously take that consideration as needed.

6) The surprising secret to making better decisions is being ok with making bad ones.

Image for post
Image for post

Failure can be a gift if you let it be. Most of the time, however, people dread failure, not just because of the immediate consequences, but because of what it may mean about them.

In my clinical experience, people who are high in perfectionism (which is very highly represented among the successful) have the hardest time with failure. This is because failures threatens their ego identity and thus damages their self-worth. It becomes not “I failed”, but “I’M a failure”, which is an over-personalized interpretation that can lead to depression or worse.

The way to counteract this is to forgive yourself BEFORE failing. Even when you’re making the decision, it’s important to reassure your ego/mind that “regardless of whether I succeed or fail, your self-worth is safe with me.”

This essentially allows you to ‘decatastrophize’ failure in advance. Armoring your self-worth is an internal way of building resilience, which makes the threat of failure less of a life-or-death situation (that brings fight-or-flight stress with it) and more of a challenge to be managed.

For More:

Written by

CEO, Maximus. Med School Professor. Executive Psychologist to CEOs & VCs.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store