Awkward much?

Awkward conversations. Nobody likes them. Everybody has to have them at some point. Over the past several weeks, I found myself needing to have awkward conversations both personally and professionally. Although these conversations are never fun or easy, I have learned how to make them go smoothly -- for all parties involved. So I'm sharing my top five tips for the next time you find yourself groaning, "Ugh, awkward much?!"

1. Identify a goal. Although tempting, the conversation is not a venting sesh about what the other person did wrong or about the problem in general. While that must be addressed, be sure to pinpoint the conversation's goal ahead of time. For example, if it's to express displeasure about what occurred, be sure to identify what the other person can do next time. If it's to tell someone what isn't working for you anymore, explain why and prioritize respect for that person while ensuring they understand your position or choice. 

2. Be prepared. Yup, I'm going to quote Scar from the Lion King here. When there's a risk of feeling anxious or emotions running high (for everyone), it's helpful to have a plan in place. Think about what you want to say. Practice the conversation in your head or aloud to yourself. If needed, organize your thoughts into bullets to see it all on paper. Anticipate the other person's reaction and plan for it. This preparation simultaneously allows you to ensure all roads lead to the conversation's goal.

3. Acknowledge the awkwardness. One of the most difficult professional conversations I've ever had was giving notice at my old law firm. When I shut the Managing Director's office door and sat down across from his quizzical expression, I said: "I want to start by saying I'm very nervous to have this conversation because it's really important to me." It completely changed the tenor in the room. When you show your vulnerability, there's a 99% chance the other person is going to respect you for it. In my recent conversations, I've said -- sometimes several times -- "I know this is awkward" or "I know it's awkward to talk about X because Y." Calling out the elephant in the room can be a relief and deflate any tension.

4. Say thank you. It's tempting to apologize for the awkwardness. For how you feel. For raising the issue. For taking up the person's time. Don't do it -- or if you feel you must, do so sparingly so as not to undermine yourself. Acknowledging the awkwardness should be enough. Instead of apologizing, thank the person for engaging in the awkward conversation. Thank them for listening to how you feel. Thank them for being receptive to your thoughts. After all, you are thankful for those things, but likely not sorry about them.

5. Don't procrastinate. Once you're ready to have the conversation, make every attempt to have it sooner rather than later. Sometimes, timing can be out of your control. However, as a recovering perfectionist, I also have the tendency to overthink. Be careful not to confuse getting prepared with overthinking. Each awkward conversation also has an expiration date of sorts, so I've learned that the sooner, the better -- for everyone.

While there are so many other facets to difficult conversations, I'm confident these five tips will set you on the right path. If you have any other tips, reply here and let me know! And good luck!

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