Jeopardy is the most popular game show in history for three simple reasons:

  1. We are amazed by people who know all the right answers
  2. We want to believe that we know all the right answers too
  3. Alex Trebek’s moustache

Today we are going to focus on the first two only. Sorry.

Knowing all the right answers matters. Not just in Jeopardy, but in life.

At least that’s what we were taught in school.

If you believe that schools are a microcosm of society, then knowing all the right answers is important in life. It separates the haves from the have-nots.

The people who know more have more opportunities. Period. Full stop. Plie.

[Editors Note: the plie is optional] In most schools, our grades – and, hence, our future academic opportunities – are based on doing well on tests where the sole purpose is to memorize and regurgitate all the right answers to miscellaneous questions.

The more schooling you have, the more we assume you know the right answers and the more we are willing to trust you and pay you.

That’s why we trust the answers of lawyers and doctors, even when our questions fall outside of their specialty.

Too bad always being right is not always right.

274. always right therapist

The Always Right Dilemma

My mother is a family therapist. She often works with couples who are having difficulty in their relationships. One of her soon-to-be-trademarked phrases is this:

You can either be right or you can be married. You can’t be both.

Her point is that healthy communication doesn’t happen when one person views it as a zero-sum game. If you insist that you’re always right, then you are insisting that the other person is wrong.

That is a crappy dynamic and it tears apart marriages, friendships, and work environments.

And that leads us to the problem with entrepreneurs.

The Entrepreneur’s Dilemma About Always Being Right

As a leadership coach and serial entrepreneur, I work with many entrepreneurial leaders. The thing I love about working with them is that they all have the same basic problems to overcome.

When they do well, they all encounter the same dilemma about being right.

You see, when you start a company, nobody knows the vision like you. By sheer necessity, you are the one that always has all the right answers.

An operational visionary who knows all the answers is what helps catapult the growth of early-stage companies.

It’s when you get to about 30 employees that the wheels start falling off the train.

At that point, knowing all the right answers suddenly turns from a benefit to a detriment. With a more robust infrastructure, you are inevitably hiring people who are specialists at their jobs. They know the right answers better than you for what they do. Or at least they should.

Always being right suddenly becomes wrong.

This is the most difficult transition for almost every successful entrepreneur – transforming from the person who knows all the right answers to the one who doesn’t.

And this brings us back to my mother, the therapist.