Judge Kindly

" The more one judges, the less one loves. " — Honoré de Balzac

Today is another free chapter from Tao of Founders. Enjoy!

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Founders roll through dozens of decisions each day. Your role demands that you spend hours evaluating, comparing, and deciding what is best for you and your startup. The quality of those decisions ultimately determines the quality of your work.

Decisions and Trade-offs

Decisions require you to judge and to establish preferences. You apply a form of judgment on everything you do: hiring, building products, writing emails, communicating priorities with your team, and so on.

Good decisions are about making good trade-offs: what to keep, what to discard, what’s important, what to ignore. Good decisions command you to define mental shortcuts, also known as heuristics, that will help you move forward without too much effort.

Good decisions and good trade-offs boil down to focus. You don’t need to have the full picture if you can focus on the most important things. In fact, you’ll likely never have the full picture before making a decision. Jeff Bezos looks for 70 percent certainty in order to make most decisions. That is the trade-off Amazon is willing to make with most decisions, embracing speed and learning over completeness.

The Risk of Harsh Judgment

Good decisions usually demand you reach a conclusion based on your imperfect information, imperfect judgment, and imperfect timing. Dealing with a constant stream of decisions each day, small and large, made with incomplete information, invites a new habit to form in your mind: you tend to jump to conclusions.

Jumping ahead is good from a decision speed and agility viewpoint. However, jumping to conclusions as a habit can encourage you to judge readily, sometimes harshly.

I’ve definitely noticed that pattern getting stronger in my mind as my founder journey goes on. With each decision piling up through the years, I feel, well, judgier. By trying to decide faster, I sometimes forget to suspend my own preconceptions. Past a certain point, I stop listening with the intent to understand; rather, I listen to confirm my decision. I haven’t always listened as well as I should have. Listening closely to customers, employees, and partners is probably the lifeline of entrepreneurs, a prerequisite to doing anything of value. Judging harshly makes it so much harder to see the finer nuances of reality as it is. It took me a while to learn how judgment creates separation.

Judgment and Relationships

Many of us are quick to judge, yet we don’t want to be judged by others. Imagine the last time someone judged you mistakenly because they had imperfect information. Maybe they jumped to conclusions or failed to give you the benefit of the doubt. How did that make you feel? No one enjoys feeling judged unfairly.

Harsh judgment can be very damaging to relationships. The moment someone feels judged harshly by someone else, two things will likely happen. Either the person being judged agrees with the judgment and feels shame, or they disagree with the judgment and feel anger. There are no scenarios I can think of where harsh judgment leads to a positive interaction.

As therapist, author, and Buddhist teacher Tara Brach explains:

“Judgment is when we’re making others bad. The deal is, as far as I can tell, we get accustomed to it. We get accustomed to demoting people in our minds and in our hearts. We get accustomed to the distance it creates.”

For a founder, judging people from a place of “bad others” can be devastating to your team. Constant judging will soon turn to blame. It will be felt and heard by your colleagues and your loved ones. Feeling judged, or avoiding being judged, shuts people down. Judgment prevents them from doing their best work because they fear blame and shame.

Pixar’s Braintrust

In Creativity, Inc., Ed Catmull, co-founder of Pixar, explains how fear of judgment hindered creativity. Employees hesitated to share ideas because they feared negative judgment. Pixar shifted the focus from critiquing the person to evaluating the idea itself. This subtle change fostered a more open and creative environment, where team members could share and explore unproven ideas without fear. Debate the ideas, not the people.

“People hasten to judge in order not to be judged themselves.”

— Albert Camus

The Weight of Harsh Judgment

Over time, harsh judgment builds into an emotional burden. This negative energy dampens your spirit. Judgment accidentally trains the mind to be rigid. The more you believe you know, the harder you become to satisfy. With this mindset, you think no one else can match your standards. You end up intolerant and exhausted.

This same rigidity almost hindered Patagonia’s mission. Founder Yvon Chouinard judged employees harshly for not sharing his passion for sustainability. Turnover was high. Over time, he learned to balance discernment with tolerance, educating rather than blaming. That shift built Patagonia’s enduring culture of inclusion and activism.

From Harsh Judgment to Wise Discernment

Harsh judgment separates. Wise discernment connects. Discernment notices without condemning. It keeps empathy, compassion, and open-mindedness intact.

The Zen story of the two monks captures it best. One monk carried a woman across a river, breaking a rule. Hours later, the younger monk judged him. The elder replied: “I left the woman by the river’s edge. Yet you still carry her in your mind.”

Judge Kindly

“We can never judge the lives of others, because each person knows only their own pain and renunciation. It’s one thing to feel that you are on the right path, but it’s another to think that yours is the only path.”

— Paulo Coelho

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