Disappointing Others

If you cannot disappoint people, you cannot lead them with clarity and honesty.

It's not that you go around trying to disappoint people. It's that doing what makes sense, having the important conversation, and making the hard decision, will inevitably disappoint your boss, direct reports, adult children, parents, and spouse.

Most of us know this in principle. In practice, three forces make it remarkably hard to do.

1. Delusion: What people ask for is not always what serves them

A physician client called me recently, worried about his 22-year-old son. "He graduated from college and doesn't know what he wants to do. He's floundering. Can you meet with him?"

I told the father I would not meet with his son until he, the father, met with me first, to address his own anxiety about his son. He was upset with my response. In his mind, the son was the problem, not him.

I had to be willing to disappoint the father in order to do what I believed was in the best interest of both of them. Had I pleased him by giving him the response he wanted, I would have deceived them both about the nature of the problem.

The kindest thing I could do was the thing he didn't want.

2. Fear: Disappointing someone with more power feels dangerous

The pull to agree, especially with an authority figure, is often less about thoughtful alignment and more about approval-seeking. The comfort of agreement is hard to resist, even when it serves neither the relationship nor the organization.

I've been on the receiving end of this one. A couple of years ago, I gave my son unsolicited advice about a job opportunity. My advice was rooted in my own fear that he was about to make the wrong choice. He listened carefully, considered my input, and then did exactly what I had warned him against.

A year later, his choice turned out to be a wise one.

He was willing to disappoint his father, and that willingness made his decision his own. It also taught me something I keep relearning: "how I see it" is usually different from "how it is."

Likewise, in businesses and other organizations, those who report to us need the freedom to let us down.

How does a boss decrease the pressure on a direct report who thinks he must tell the boss what the boss wants to hear? How much useful intel, how many great ideas, stay hidden because employees can't be honest with the boss?

3. Discomfort: Disapproval creates pressure to cave

When our decision provokes a reactive, disapproving response, emotional pressure to reverse course usually follows.

A client I'll call Lydia, a college president, heard a suggestion from a board member as a directive: "You need to spend more time building donor relationships and less time meeting with your cabinet." Lydia already had a well-thought-out plan for reaching out to donors but began to mistrust her plan based on one comment from a board member.

She almost caved. With her leadership team's backing, Lydia stayed with her plan.

The discomfort of letting someone down can be so acute that we "take back" a sound decision for no other reason than that it disappointed someone.

When caving in to disapproval, we are in danger of outsourcing decisions to whoever is most upset. A leader who does this repeatedly trains everyone around them that displeasure, expressed loudly enough, trumps good judgment.

Disappointment is not carelessness

None of this is a license to be dismissive or harsh. There is a world of difference between disappointing someone while staying in contact with them and disappointing them through distance.

One is an act of respect: listening, explaining your thinking, and remaining open to being wrong. The other is avoidance.

The willingness to disappoint is a measure of self

Your capacity to tolerate another person's disappointment is a direct measure of how well- defined a self you bring to your relationships.

The leader who cannot bear to disappoint is not actually being kind. They are being governed by the anxiety of others, and by their own need to be seen as agreeable, harmless, and good.

Chronic accommodation hurts both parties, just as chronic opposition does. At some point, every important relationship asks the same question: Can you stay connected to me and disagree with me?

Leaders who can answer yes are free to do what makes sense. Leaders who can't will spend their lives doing what makes everyone comfortable.

In the end, that lets everyone down. Including you.