How Conan O’Brien Effectively Connects With His Team

“You don’t have to tell anybody that you’re the best!”

Despite being a late-night show host and a comedic genius, Conan O’Brien showed how he was able to connect with his employees effectively. In his remote videos with his staff, he showed that he was able to get along with his employees very well.

His core technique to every one of his shows is through self-deprecating humor.

But how was he able to use this as his advantage other than his shows? And why use this technique?

Recently, Conan attended an Oxford Q&A Session where he explained why he made self-deprecating jokes as the core of the content of any shows he did.

“I don’t need a random person or a troll to tell me that I suck, because deep down, I know that.”

— Conan at Oxford, 2020.

While some may think that self-deprecating jokes are a way to conceal someone’s insecurities, it’s actually doing the opposite. It helps a lot with their emotional intelligence.

A study found that it helps boost your confidence and makes you happier. The speaker had no problem being the center of the joke and can still have fun together. As a result, the technique also helps them to be more sociable to others.

Conan does this a lot. He always made fun of himself and didn’t care if he would look ridiculous. That’s why it’s easier for him to connect with people as he visits certain destinations — because he made them feel comfortable to be around him.

Plus, it also helps to keep his ego in check. In a Q&A session at Harvard in 2016, Conan said that he prefers being laughed at (unless he can make fun of other people and get away with it, he said) because it helps him to be humble.

As a result, he could easily make friends with others, and make comfortable conversations with them, real conversations, which leads to many benefits in relationships. Here are the benefits of making self-deprecating jokes:

Honesty

An example is his own podcast: Conan Needs a Friend on Apple Podcast.

The title itself is already self-deprecating, you don’t see a lot of titles like that, and he was being really honest. But Conan did it anyways, and it made everyone really true with one another.

His guests and himself can have a deep conversation. They talked to him about their past, their insecurities, and so many things that you probably wouldn’t share with anybody but your close friends or families. And take note, Conan was able to get them to say that, recorded it, and released for the public to listen, and the guests had no problem for the world to hear their conversation.

Conan is able to get people to talk to him about any sensitive content, and still get away with it.

For Conan, it helped him gain an audience and have his staff open up to him, giving the workplace a very open culture. You can see this in his assistant, Sona, where she can insult Conan freely.

Being honest is very important in any kind of business. It helps employees to be open with one another and to their superiors, and stay true to their work.

No Brags

“You’re not a badass. You’ve got a lot to learn.”

— Conan to his son, mentioned at Harvard 2016 .

This is a big red alert for Conan. Thanks to his self-deprecating habit, he knows how to keep his ego in check, stay humble, and find humor in himself.

He hardly brags that he is the best host show or that he is from Harvard, even if he did brag, it wasn’t delivered in a boastful manner. He despises egoism, which is why it helps him to effectively communicate with his staff.

The point is, no one will love you if you are proud and a showoff.

Here is an example.

In his Oxford interview, before the session started, he shared an email he received from Cambridge. Cambridge too asked whether he too can attend their Q&A session, Conan received this message after he accepted to do a Q&A in Oxford.

However, the content of Cambridge’s email turned out to be bragging. The email wrote that Conan should do the Q&A for Cambridge instead of Oxford because their university is older and that their students will ask him questions that will blow his mind.

Long story short, Conan declined Cambridge’s invitation. Even Comedians hate braggers, so don’t do it. You won’t get anybody to be with you if you do that, leading to my last point that ultimately helps him connect with his staff.

Inclusion

As stated before, Conan often includes his staff in his remotes, which also became one of his big highlights in his show business. It is rare to see anyone sharing what’s going on behind the scene of their business, and Conan had no problem to show to the world what his office work life looks like. It gained positive insights after that.

Including your employees into the main project is a huge help for a healthy business. An inclusive culture can help achieve financial targets as employees become more engaged and creative in their work because they felt included.

A study from Deloitte stated that an inclusive culture helps employees a lot. It makes them feel safe and heard, giving them a sense of belonging in the company.

Your companies will never succeed without the people working within. And to make them stay at your business is that you need to make them feel safe, basically what any leaders should do.

Conan made this environment work. He includes his staff, listens to them, and made sure it is in the project. This helped his show have a lot of evergreen content videos.

Today, his net worth is $95 million.

The Take

I did a little research myself about this technique and tried to practice them with others, even when I work.

The result is just like how Conan O’Brien was able to connect with others in his shows. Though I didn’t do it as silly as him, I just interpret it from the discussions above. The responses were positive, people are more open, they are willing to speak more to me, and give me honest answers.

I still use the self-deprecating technique up to this day, and it’s already a habit. I think this is a great practice for all of us to try.

I hope you learn something from here.