Awkward customer service conversations happen. Here’s how to get through them.

It happens at some point to everyone who talks to customers. One day, you pick up the phone, start speaking, and suddenly find yourself in a painfully awkward conversation.

“Hey bubby, how’s it hanging?”

“What? Did you just… call me… ‘bubby?’”

“Oh, I, uh, oop. I mean, oops.”


“Yeah, I… Cool. Cool. So, how are you?”

“I’m fine. I guess?”

“That’s cool! I mean, great!”

“Is it?”

“Sure thing. I’m— *yawns*

“Um, are you okay? Is everything alright?”

“Yes, I’m so sorry. Can we start over?”

“ *Laughs* Yeah, maybe we should.”

I’ve had more exchanges like this than I’d like to admit. I’ve called people by the wrong names, made jokes that didn’t land, overshared, interrupted, lost the thread, and so on. And so on. 


Memories of the worst conversations linger in my brain for months, even years, after the fact. I’ll wake up in the middle of the night, remember a two-minute phone call I had in 2012, and think oh my God, I can’t believe I said that. But then I take a breath and remind myself:

Awkward conversations are normal.

Messing up a conversation with a customer (or anyone, for that matter) is an entirely human thing to do. Few people consider themselves conversational whizzes. Many of us experience some level of social anxiety and dislike—if not loathe—small talk. 

These feelings of discomfort, along with the embarrassment that follows awkward moments, sting particularly sharp right now. Thanks to the COVID-19 pandemic, we’ve all been stuck inside for months. If you’re like me, you’re feeling socially rusty and on edge. 

And then there are the various charged political topics currently on people’s minds. It’s all too easy for conversations to veer into sensitive territory—and you may not realize the other person disagrees with you until it’s too late.

All of which is to say that at a time when “How are you?” is a loaded question, difficult conversations are bound to occur.

You don’t need to agonize over calling Mike “Steve” or giving Nadia too many details about your cat’s litter box habits. Weird exchanges with customers happen. It’s okay. It might even be a good thing sometimes. 

As a matter of fact, you can spin an awkward conversation into an opportunity to create a deeper connection with the other person. It all comes down to your attitude and ability to react carefully and authentically in the moment. 

Here are a few tips for recovering from awkwardness and overcoming conversational roadblocks when talking to customers.

Lighten up.

Your attitude is your greatest asset in customer service. A positive, enthusiastic outlook not only helps your customers feel welcomed and comfortable, but keeps you motivated to continue answering the phone even when the last conversation (or three) didn’t go as anticipated.

Don’t take yourself too seriously. People are drawn to people with senses of humor. If you can laugh at yourself (without wallowing in self-deprecation), you’ll make your customers feel at ease. And ultimately, what they’ll remember most when the conversation is over is how you made them feel—not what you said, word for word.

When you do make a mistake, laugh it off with a quick acknowledgment—“Oh, oops, that’s not your name, is it?”—and then…

Let it go.

Move on. There’s no reason to draw out an awkward moment. Keep the conversation rolling along and maintain your lighthearted attitude.

Again, it’s important to put the self-seriousness aside. You should take your responsibility to your customers seriously, but you don’t need to center yourself—or your conception of your self-worth—in executing that responsibility. 

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In other words, remember that it’s about them. Any conversational faux pas only matters insofar as it negatively impacts the customer. A minor mistake doesn’t mean anything as long as you provide the other person with outstanding service and a positive overall experience.

Apologize when you need to.

Sometimes, mistakes and awkward moments do cause problems. Calling someone the wrong name, for instance, could hurt their feelings. Giving someone incorrect information can create frustration and confusion. 

In these sorts of cases, you owe the customer an apology. Say you’re sorry and take responsibility. If necessary, offer an explanation and communicate what you’ll do to remedy the situation. It helps to empathize with your customer and verbally acknowledge their feelings. 

Keep it direct, personal, and brief, and then usher the conversation towards practical matters. For example:

  • “Oops, I’m so sorry, Dr. Martinez. I got you mixed up with another client and had the wrong information on my screen. I’m looking at your file now. Let’s try that again. How may I help you today?
  • “I’m sorry, Sam, you’re absolutely right about that. My fault—I should have listened to you more carefully the first time. Let me know if this sounds better…”
  • “Ms. Phan, I want to sincerely apologize for your experience today. We didn’t hold ourselves to the standard we’ve set for customer service. I can imagine how disappointed you probably feel. I’ll make sure we handle any future interactions in a more professional manner.”

Be patient and listen.

Not every conversational blip, awkward moment, or customer issue will be resolved immediately. Sometimes, the best option is to listen and let silence happen. Stay calm and be patient and present in the moment. Instead of filling the silence, pause for a beat and see how your customer responds. If they take the lead, great! If not, then it’s time to jump in and steer the conversation in a new direction.

Also, be patient with yourself. You will make mistakes. Forgive yourself for them and, if you can, learn from them. 

Reflect on your experiences: What were you feeling when you said that? What caused the awkward moment to occur? You might discover that the reason the mistake happened was that you hadn’t met your own needs. Maybe you were hungry or tired, or weren’t in the right emotional state for the conversation. 

Take the time to understand and grow through the experience. The better you know yourself, the better you’ll be able to serve your customers.

Use words and phrases that build trust.

The words you choose to say matter much more than the ones you utter by accident. Try using phrases like these to draw attention away from small mistakes and build connections in your customer service conversations:

  • “I understand.”
  • “Thank you.”
  • “Of course.”
  • “Absolutely!”
  • “I appreciate it.”
  • “That makes sense.”
  • “Is that right?”
  • “How may I help you?”
  • “What can I do to improve your experience with us?”
  • “Is there anything else I can help you with?”

Create connections every time with Ruby.

At the very least, an awkward conversation is a memorable conversation. But there’s no reason you need to wake up at 3am cringing about uncomfortable moments with customers. 

Sign up for Ruby and we’ll take care of customer service conversations for you. You can rest easy knowing the people you serve feel are connecting meaningfully with your business and experiencing unforgettable customer service exchanges—in the best possible way. 

Experience Ruby’s legendary customer service for yourself.

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