Welcome to One Thing Better. Each week, the editor in chief of Entrepreneur magazine (that’s me) shares one way to be happier and more effective at work — and build a career or company you love.
Today’s edition is sponsored by Kick, my favorite bookkeeping software (for real!). See details at the end of the newsletter.
You hate awkward conversations.
Maybe you just had one. Or you’re avoiding or dreading one. Or you’re just in a room where you don’t know anyone.
You try to hide your awkwardness, but that only makes things worse. It’s like being a teenager again!
Today, I’ll give you a simple antidote to this. It’ll diminish your awkwardness, boost your confidence, and make uncomfortable situations a lot more comfortable.
The trick is this: Lead with your awkwardness.
Because here’s the thing: Awkwardness is our great human equalizer — and when used properly, it helps us relate and connect to others.
So let’s start with an awkward conversation in the making…
“I’m the new boss, and feeling awkward”
I recently talked with a woman named Mary. She’s getting shunned at the office.
Mary got promoted above her friends. Now she’s their manager and they resent her. She needs to address the situation, but she’s unsure how.
“It’s awkward, and I don’t want to be the person who feels awkward,” she told me. “It’s hard to be in a position of leadership and have awkward feelings.”
Mary and I talked on my podcast Help Wanted. Take a listen; there’s a lot to unpack! But to me, her admission of awkwardness was the key to everything.
Because although her concern is understandable, it’s also worth asking: Is awkwardness actually a problem here? Or is it the solution?
The upsides of awkwardness
Let’s hit pause on Mary for a moment. And instead, let’s just talk about awkwardness.
By dictionary definition, awkwardness is a combination of things — difficulty, embarrassment, insecurity. But in practice, I think of awkwardness like this:
Awkwardness is the act of doing something, but being painfully aware of your imperfections.
That means awkwardness is an action word. It is the result of boldness! You cannot be awkward unless you do something uncomfortable — and that by itself is commendable. If you’re awkward at parties, for example, then it means you showed up to the party!
Everyone can relate to this. Perhaps it’s why “awkwardness” is peaking right now — just look at this chart from Google, tracking how often the word has appeared in books across the past century:
This makes awkwardness a great leveler! Everyone, at every level of status, feels awkward — and because it’s so relatable, everyone is culturally allowed to feel awkward.
Put another way: Awkwardness does not negate competency. You can feel awkward and still be viewed as competent.
That makes it a powerful tool in conversations.
Which brings us back to Mary…
Imagine that you’re Mary. She needs to talk with these former friends of hers, but “it’s hard to be in a position of leadership and have awkward feelings.”
So what should Mary say? Here’s my answer: Lead with the awkwardness.
Mary could start like this: “Things have been awkward between us, and I realize this conversation may feel kind of awkward, and I feel awkward having it…”
By acknowledging the awkwardness, she de-fangs it. She also humanizes herself without actively soliciting sympathy, and opens the door for her colleague to relax. And none of this undercuts Mary as a leader, because a leader is allowed to feel awkward.
But of course, what comes next is equally important…
Awkwardness must be your springboard
You can admit awkwardness — everyone relates to that! But you can’t actually be super awkward. That’s uncomfortable.
So what do you do? I wrote it above: You lead with your awkwardness.
I borrowed that language from leadership expert Jacob Morgan, who wrote a book called Leading with Vulnerability. He advises this:
People say that vulnerability is a great leadership skill — but that’s only half the formula. “Vulnerability creates connection,” he told me, “but you must also demonstrate competence.” If you only show vulnerability, you seem lost and out of control. But when you admit that you messed up or are feeling scared, and then follow that up with a plan of action, people trust you to lead them.
The same is true for awkwardness, in any setting.
Making an uncomfortable request? Start off by saying, “This feels a little awkward to ask…” — and then make the ask in a friendly, clear, direct way.
Unsure how to start? When I’m alone at a conference, I’ll often walk up to other attendees and say, “Hi, I’m wandering around awkwardly looking for people to talk to.” They instantly relate — and then I ask them questions to prompt real conversation.
There are endless ways to do this.
I know — if you’re feeling awkward, this is easier said than done. But remember what I said about awkwardness: It is an action word. You are awkward because you are bold.
Awkwardness is the antidote to awkwardness. So lead with it. Get it out of the way. Then be the competent, insightful, powerful person you are.
That’s how to do one thing better.
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