224: How Having Awkward Conversations Can Completely Change Your Life in Surprising Ways



That’s the question that Melissa Dahl poses in her new book Cringeworthy, a Theory of Awkwardness. It’s also something that I’ve been pondering for about 10 years now. Particularly, the area of having difficult and awkward conversations and how they impact your life. My friend Jenny Blake had told me about Melissa and her work; I knew I had to meet her! Fortunately, I was heading to Austin, Texas to an event put on by Express (my favorite clothing company on planet earth) to record our podcast Live at South By SouthWest, one of the larger conventions and festivals in the world. I tweeted Melissa and convinced her to join me onstage to discuss how difficult and awkward conversations can completely propel your career forward.Listen to the entire conversation here:


Much like the word “happiness,” awkwardness is used to describe an insane amount of events, happenings, feelings and more. This ranges from accidentally walking out of the bathroom with your fly undone all the way to asking your boss for a promotion. After talking to Melissa, she confirms that the awkward conversations that are most difficult are possibly some of the most valuable.

Maybe it can be an opportunity to become that person you think you are or you would like to be.

Here are a few examples:

  • Asking your boss for a raise (awkward yes! Profitable? Very).
  • Telling your spouse or significant other that you want to stop taking on debt because you realize it’s trapping you (scary… even with one of the people who loves you most).
  • Setting boundaries with people at work who are taking all of your time, adding more to your plate and causing you to overwork.

All awkward, all a little scary, all difficult conversations. All of them can have a profound impact on your quality of life. All of them are opportunities to move a little closer to the person you’d like to become.   In fact as I think back, 100% of the events that made the biggest impact on my adult life have involved a difficult or awkward conversation. (I can even directly trace awkward conversations to over $300,000+ extra income over the last 7 years that I had a boss.) So yes they’re valuable blah blah… if that’s the case you might think “Can’t I make them any easier?”


I asked Melissa this exact question. Turns out there is. And you’re not going to like the answer. It takes intentional practice. You have to decide that you’re going to have the conversation, then do it. When you do enough of these you can actually build up an Awkwardness Tolerance (my words, not Melissa’s)! Additionally though, you can get better at making it easier in those difficult moments. Here’s an example that Melissa gave: “It’s the kind of thing like you’re going into a job interview and all of a sudden you’re like ‘Wait I forget how chairs work. What am I supposed to do with my hands?’ I just did this with my boss’s office the other day. She has a big couch thing and I sat down and I kind of put a pillow like this and then I was like wait is that weird?”

“Is this weird? It’s a weird thing to do and just couldn’t fixate or focus on anything but it.Those two things really get you locked in that cycle. Psychologists who study this say it’s partially caused by self-consciousness.” The way out is to focus on anything but yourself. “So you know if you’re lucky enough to be public speaking with somebody else you focus on the person in front of you. Just anything but yourself you can focus on.” “If it’s the job interview scenario, you prepare beforehand and maybe think about three things you’re going to say about the job or whatever. You know it just kind of like zoom out. Zoom out and focus on the big picture and just don’t focus on yourself because that is the best way to be like wait what do I do with my hands again. That’s something that helps.”


My experience is that it takes the same amount of effort, worry, discomfort, and energy to have a bad awkward conversation as it does a good one. You can either put in a little prep work in making these most effective or you can deal with the fallout from a bad conversation. I might be a little biased on this from years of working in HR and helping people untangle bad conversations like these. Here’s what Melissa told me about the research on how to make these conversations most effective: “There isn’t a ton of research on this but there is some. And what little there is has suggested that there are two things that help. One is “Perspective Taking” which is kind of a fancy word for empathy. It’s putting yourself in the other person’s shoes and trying to imagine how they might be feeling and remembering it’s not all about you….Maybe you’re having a awkward conversation because you want a raise. Think about it from your boss’s point of view. Don’t think about it from your point of view. Don’t frame it as it’s because the cost of living in New York or wherever you live has gotten insane. Frame it as, well this is what I bring to the company. This is why it makes sense for you to give this to me. It’s perspective taking. The other one is called “active processing” which is another kind of fancy term for that kind of cooler rational side of of a conversation. I’ve seen people online promote #MakeItAwkward meaning like you’ve got to get up into somebody’s face and you’ve got to make it awkward and tell them they’re wrong or whatever. But that’s actually not going to be that effective. Where you can actually change someone’s mind or have a useful conversation is to stick with that cooler side.”


It turns out it’s not about trying to be less awkward, or even avoiding awkward moments. I’ve personally experienced that when you lean into those moments you have the largest opportunity to grow and develop as a human being. Melissa refers to this concept in her book as “finding your growth edge.” If you want to learn more about your growth edge, definitely listen to the entire interview or download the transcript below. Afterwards, it’s your opportunity to build your awkwardness tolerance. What’s that conversation that you know you need to have, at work, at home, with a friend or coworker? You know which one I’m talking about. Take some of what you’ve learned and have that conversation. Remember it’s in these boundaries of awkwardness and discomfort that the best of life happens.