Eating Lunch Together Builds Team Trust

The worst thing a leader can do is hesitate on difficult decisions. When faced with two bad options, the psychological muscle you must build is the ability to look into the abyss and choose the slightly better path.

As a CEO, you'll constantly face situations where both choices are horrible. The natural response is to avoid making a decision, but this hesitation is extremely destructive. It locks up the company, creates uncertainty, and forces senior leaders to jump into the void and make decisions for you. This is when organizations become political and dysfunctional.

The only value you add as a leader is when you make decisions most people don't like. If everyone agrees with the decision, they would have made it without you. Your job is to see what others don't and make the hard call, even when it's unpopular. This requires running toward fear rather than away from it.

When you hesitate, you're often trying to avoid criticism. But leadership isn't about being liked in the short term—it's about being respected in the long run. The most important things you'll say to your team are things they don't want to hear. This is especially true when you need to replace someone who isn't performing. While it's painful to have those conversations, the alternative is usually worse.

For individual contributors, understanding this leadership principle means recognizing that your manager's unpopular decisions may be addressing problems you don't fully see. When you disagree with a decision, consider that they might be choosing between two difficult options rather than ignoring an obvious solution. The best way to influence decisions is not by expecting your leader to avoid hard choices, but by helping them see better alternatives.

Building this decision-making muscle takes practice and often requires going through struggle. As Ben notes, "CEOs who had an easy run of it, who just launch a product and it's an instant hit, find it very hard to develop that muscle compared to those who gutted it out for multiple decades before having big success."

The median score on the "CEO test" is 18, not 90. You have to be comfortable getting a lot of D-minuses, because a D-minus is fine as long as you don't get the F—as long as you don't run out of cash or lose everything. Keep going, and remember that hesitation is your greatest enemy.