I Made a Good CEO Cry. I Was a Jerk.

I Spent Years Giving Compliments With a Teaspoon. I Should Have Used a Ladle.

I spend too much time telling people who they should be and far too little time celebrating who they are.

I actually made one of my company’s CEO cry.

It was the most successful investment I ever made in my angel investing career.

The CEO had grown the company from $4mm in revenue to $16mm.

He missed his numbers about halfway through the $16mm fiscal year. I was then the Chairman of the Board of Directors and the largest investor. I called the CEO and asked for a meeting. A meeting that I wanted sooner rather than later.

I started the meeting by telling him how disappointed I was that he was missing his numbers. I then recounted why I think he was missing his numbers. I went through his lack of urgency with his direct reports, his lack of commitment to this important goal, his lack of timely action in replacing the non-performers, and, finally, his seeming calmness in the midst of this crisis.

As I went on and on about his shortcomings, he began to cry. Not big, heaping tears where it is difficult to catch your breath. These were tears of brokenness. But being a good Chairman, I ignored his tears and finished what I believed needed to be said. I wasn’t there to show empathy or be put off by an emotional showing. I was there to address the missed numbers and his inaction, which I saw as the culprit.

I left that meeting asking myself, “Could I have handled that meeting differently?”

The next day, the CEO called me and asked if he could come to my office.

In that meeting, he asked me if I wanted him to resign.

I proceeded to tell him all he had accomplished, how he had grown the company’s revenue over the last few years, and how he had built an amazing management team. How he and his team designed practices and processes to increase efficiency and reduce future financial liabilities, and how the customer base was a great source of references.

He listened, then said, “Why don’t you ever talk like this to me?”

I said, “I don’t know. I guess I have an eye that only sees what is wrong, and then I feel like I have to talk about it first.”

He said, “What you said in the last meeting drove me to the floor of my office. What you said today lifted me and motivated me to even greater achievements.”

And then he said this. I will never forget these words.

“You give compliments with a teaspoon. You should think about giving compliments with a ladle instead.”

This is what I want people to do with me, too.

But this is not what happens. I am also criticized. Told by others what is wrong with what I said or did. I am rarely told what I am doing right, what I accomplished, or what they appreciate about me.

So my excuse for my bad behavior is, “I can’t give what I don’t have.”

This is a bad, bad excuse. Because more people than not do compliment me. But I don’t receive it.

I treat myself like I treat others.

This became clear to me recently at breakfast with the CEO of a $1 billion company. I told him how much I admire him. I listed his characteristics and his achievements that impressed me. I then double down on speaking to the man: he is in Christ, and what a fortunate company to have him lead it.

He listened to me and said, “Thanks for saying that, but if you only knew.”

I called him out on his reaction. I said, “Why do we do this to ourselves?”

That is not how God talks to us. God made us in His image, and He loves us. Why do we talk to ourselves harshly? Why are we surrounded by people who judge us? People who tell us we are not enough. What is wrong with us?

We discussed these questions for a few minutes, then moved on to something else. It appeared to me that this topic made him uncomfortable.

And it was this breakfast that reminded me that over twenty years ago, I made that great manager who worked for me cry. The last time I remembered this story was two months ago when I attended that man’s funeral.

I was sitting in his funeral at his church and thought, “If I were asked to speak on this man’s life, what would I say?”

I would say, “I’m sorry for that day. I am sorry for what I said. Thanks for forgiving me. Thanks for your advice. You were a great friend over the last twenty years. You changed my life with your advice. I’ll never forget it.”

Don’t give compliments with a teaspoon. Use a ladle.