Awkward Conversations

speak with people Apr 29, 2024
7 Tips to Navigate an Awkward Conversation




Have you ever found yourself in a conversation where you sense it's about to veer into awkward territory?

I was at a networking lunch recently and the organizers did the one thing we all know they have to do, but no one wants them to actually do it. What’s the thing you ask?

The organized meet and greet.

Personally, I would prefer they don’t force anything and let us connect on our own. I understand why they do it and it can be helpful in the long run. This is a networking event after all; we should expect these sorts of activities.

Well, on this day, it was kind of like speed dating.

We each had 5 minutes with a different leader and then everyone rotated. Conversations were going well until a leader, we’ll call him Joe, sat down. The bell rang and I asked my first question. Joe responded with a nod. That’s it.

I could sense more cringe worthy moments ahead. He was supposed to ask the next question and he just stared off in the distance. So, I asked another question. Again, Joe nodded while never looking at me.

Finally I asked a third and he responded with ‘why would you even ask that’?

Then before the bell rang, someone he knew walked by and he engaged in a full conversation with them. I was shocked to say the least. This went from mild cringe worthy and awkward territory to full blown def con awkwardness.

Within a few seconds, someone new was sitting in front of me and thankfully we were able to have a normal conversation.

Now, like Joe, I’ve had many, many awkward conversations and cringe worthy moments. I’m a talker so I’ve had moments where I couldn’t stop talking. There have been times when my thoughts didn’t go through a filter and they just came rambling out. Meanwhile, others may experience their mind going blank and have no idea what to say next. Can you relate?




Whether it's a difficult interaction with a coworker, an uncomfortable discussion with a friend, a nerve-wracking chat with a stranger or a just flat out weird moment with a family member, awkwardness can strike at any moment.

Maybe it’s at a networking event, a work party, after a meeting or on the golf course. Regardless of the location, you know it’s coming. You can sense it. Whether it's due to your own discomfort or the other person's, you can feel the tension building.

How do you respond?

How will they respond?

What can you do to fix this catastrophe?

We have all been there.

We have all been the awkward one in a conversation at some point. There could be a variety of reasons we’ve slipped into the awkward territory. Maybe we’re just having a bad day. Perhaps stress was getting the best of you. You may have been tired. Or maybe you’ve allowed some unhealthy communication habits to slip into your leadership.

At Speak with People, we call them “Speaking at People” habits. These are the unhealthy habits we allow that end up disrupting and destroying our connections with people. You see, we all have the choice to speak “with” people or speak “at” them.

When we speak with people, we breathe life into our conversations. We are fully connecting interpersonally and embracing healthy habits.

When we speak “at” people, we suck the life out of our conversations. Rather than connecting, we get stuck in unhealthy habits, which leads us into the awkward territory in our conversations.

The reality is, many leaders don’t realize they are utilizing unhealthy habits in their communication. Often these toxic habits lay below the surface in a leader's life, going unnoticed and need to be addressed. These unhealthy habits include things like inauthenticity, a lack of empathy, rushed communication, thoughtless speech and mixed body language. This is not the complete list, but this gives you the general idea.

Again, we have all been there. But, as leaders, we are in the people business and we need to elevate the importance of every interaction with another human being. It doesn’t matter if it’s our barista, co-worker, boss or potential customer.

Every interaction matters.




Let’s explore seven tips for making awkward conversations less, well, awkward.

  1. Acknowledge the Awkwardness: The first step in diffusing an awkward situation is to acknowledge it. Pretending that everything is fine when it clearly isn't only serves to heighten the discomfort. Instead, break the ice by addressing the awkwardness head-on. A simple acknowledgement like, "Well, this is awkward, isn't it?" can instantly lighten the mood and create a sense of camaraderie between you and the other person.
  2. Find Common Ground: One of the most effective ways to smooth over an awkward conversation is to find common ground with the other person. Look for topics you both can relate to or shared experiences you can bond over. Whether it's a mutual interest, shared hobby or similar background, finding common ground can help bridge the gap and make the conversation feel more natural.
  3. Use Humor: Laughter is the best medicine, especially when it comes to awkward conversations. Injecting a bit of humor into the dialogue can help lighten the mood and alleviate tension. Just be mindful of your audience and ensure that your jokes are appropriate for the situation. A well-timed quip or a lighthearted comment can work wonders in turning a cringe-worthy conversation into a more enjoyable conversation.
  4. Practice Active Listening: In awkward conversations, it's easy to become so preoccupied with your own discomfort that you forget to listen to the other person. By practicing active listening, you will foster meaningful communication and build rapport. Make a conscious effort to focus on what the other person is saying, ask follow-up questions, and show genuine interest in their perspective. Not only will this help you navigate the conversation more smoothly, but it will also make the other person feel valued and heard.
  5. Shift the Focus: If the conversation veers into uncomfortable territory, don't be afraid to gently shift the focus to a different topic. Redirecting the discussion to a more neutral subject can help steer it away from awkwardness and towards smoother waters. Look for an opportunity to introduce a new topic or ask a relevant question that can help steer the conversation in a more positive direction.
  6. Practice Empathy: So many leaders think empathy is just feeling sorry for someone. That couldn’t be further from the truth. Empathy is the ability to understand and share the feelings of another person. In awkward conversations, demonstrating empathy can go a long way towards easing tension and fostering connection. Put yourself in the other person's shoes and try to see the situation from their perspective. Validate their feelings, show compassion, and offer support if needed. By practicing empathy, you can create a safe space for open and honest communication.
  7. Know When to End the Conversation: Sometimes, despite our best efforts, awkward conversations can't be salvaged. In these situations, it's important to know when to gracefully end the discussion and move on. Don't feel obligated to prolong the conversation if it's causing undue discomfort for either party. Instead, politely wrap things up with a simple closing statement or excuse yourself from the conversation altogether. Remember, it's okay to prioritize your own well-being and peace of mind.

Awkward conversations are an inevitable part of life, but they don't have to be unbearable. Not every awkward conversation is like speed dating and will have a bell to end it. And not every conversation will be cringe worthy. But, they are going to pop up and you can be ready.

By following these seven tips, you can navigate awkward situations with confidence and grace. Remember to acknowledge the awkwardness, find common ground, use humor, practice active listening, shift the focus when necessary, practice empathy, and know when to end the conversation.

With a little patience and a lot of practice, you'll become a master at making awkward conversations less awkward in no time.


By Jason Raitz - CEO, Speak with People

Jason has decades of experience coaching healthy communication practices. Learn more about Speak with People's Healthy Communication Training and invite Jason to speak to your company.