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- [00:07]
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This is Help Wanted, the show that makes your work work for you. I'm Jason Pfeiffer, editor in chief of.
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Entrepreneur magazine, and I'm money expert Nicole Lapin. On Tuesdays, Jason and I answer the helpline and help callers solve their work problems.
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And on Thursdays, I give you one way to improve your work and build a career or company you love.
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And it starts now.
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You hate awkward conversations. I mean, I guess, does anyone like them anyway? Maybe you just had one, or you're dreading or avoiding 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 will 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 to and connect with others. So let's get into it, and we're going to start with an awkward conversation in the making. Now, this comes actually from Help Wanted. There's an episode that we ran on November 5, 2024. The title of the episode, you can go find it, is Tall Poppy syndrome, How to navigate your co workers jealousy. And in that conversation, Nicole and I talked to a listener named Mari who is getting shunned at the office. A quick refresher if you haven't heard the episode. Mari got promoted above her friends and now she is their manager and they totally resent her and she needs to address the situation, but she's unsure how. So here's what she told us when we were talking to her. She said, it's awkward and I don't want to be the person who feels awkward. It's hard to be in a position of leadership and have awkward feelings. Now, there's a lot to unpack in this situation, but to me, her admission of awkwardness was kind of 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? Let's talk about the upsides of awkwardness. To do that, we're going to hit pause on Mari for a second. We'll come back to her. Instead, let's just talk about awkwardness. By dictionary definition, awkwardness is a combination of things. You know, 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 that awkwardness is kind of an action word. You know, awkwardness is the result of boldness. You cannot be awkward unless you are doing something uncomfortable, something that would give you the opportunity to be awkward. And that by itself is commendable. If you're awkward at parties, for example. Well, the only way you're awkward at parties is if you showed up to the party. Everyone can relate to this. Perhaps it's why awkwardness is peaking right now. I did this search in Google. You can search Google by how many times a specific word appears in books over a long period of time. And I searched for the word awkwardness over the last hundred years of books and it is fascinating. It was basically exactly the same from the 1920s to like 2008, 2010ish. And then suddenly there is a spike that just keeps going up and up and up. The last couple years of our lives have featured the most number of uses of the word awkward in books historically. What does this say? Well, to me, what it says is that awkwardness is a great leveler. Everyone at every level of status feels and relates to awkwardness. And because it's so relatable, everyone is culturally allowed to feel awkward. We are giving ourselves permission because we're all feeling it. It's not a bad thing anymore. So put another way, awkwardness does not negate competency. I actually said that on the podcast episode here at Help Wanted with Mari, but I want to really unpack it because I spent time thinking about it afterwards. You know, really, awkwardness does not negate competency. You can feel awkward and still be viewed as competent, and that makes it a powerful tool in conversations. So that brings us back to Mari. Imagine that you're her. Mari needs to talk with those former friends of hers at work. But as she said, it's hard to be in a position of leadership and have awkward feelings. So what should Mari do? Here's my lead with the awkwardness. Mari could start the conversation by saying something like this. Hey, former friend, things have been awkward between us, and I realize this conversation may feel kind of awkward, and I feel kind of awkward having it, and so on. By acknowledging the awkwardness up front there, Mari just totally defangs it. She also humanizes herself without actively soliciting sympathy, which you never want to do in an awkward situation, and opens the door for her colleague to relax. And none of this undercuts Mari as a leader, because a leader is allowed to feel awkward. Remember, it's okay, we have permission. It is allowed. But of course, what comes next is equally important, because awkwardness must just be your springboard. You can admit awkwardness because everyone relates to that, but you can't actually be super awkward. You know, that's uncomfortable. So what do you do? Well, I said it above. You lead with your awkwardness. I borrowed that language from leadership expert Jacob Morgan, who wrote a book called Leading with Vulnerability, and 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 immediately with a plan, plan of action, well, now people trust you to lead them. The same is true for awkwardness in any setting. So let's go through a few of them. Making an uncomfortable request. For example, start off by saying, this feels a little awkward to ask. And then make the ask in a clear, friendly, direct way. Unsure how to start something? Well, when I'm alone at a conference, I will often walk up to other attendees and I'll just say hi. I I'm wandering around awkwardly looking for people to talk to. And then they instantly relate because they have basically been doing the same thing but just didn't openly acknowledge it. And then I ask questions to prompt real conversation. There are endless ways to do this. I know if you're feeling awkward, this is much 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 you can be the competent, insightful, powerful person that you are. Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.
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Pfeiffer and me, Nicole Lapin. Our executive producer is Morgan Lavoy. Do you want some help? Email our helpline@helpwantedoneynewsnetwork.com for the chance to have some of your questions answered on the show and follow us on Instagram @moneynews and TikTok MoneyNews Network for exclusive content and to see our beautiful faces. Maybe a little dance?
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Oh, I didn't sign up for that.
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All right, well, talk to you soon. This episode is brought to you by Progressive Insurance. Do you ever find yourself playing the budgeting game? Well, with the Name your price tool from Progressive, you can find options that fit your budget and potentially lower your bills. Try it@progressive.com Progressive Casualty Insurance Company and affiliates. Price and coverage match limited by state law. Not available in all states.