Dealing with Difficult Digital Conversations 

by Brittany Moor

In today’s digital world, more and more of our conversations are happening through a screen. Between emails, texts, instant messages and social media, we often struggle to convey tone and meaning with just our words. And when the conversation goes sideways, it’s hard to craft a response without increasing tension or damaging a relationship.  

When we experience a misunderstanding through our screen, how can we craft a response that is both respectful and direct? 

From a friend’s recent experience booking a cottage online, I learned two helpful strategies for handling an uncomfortable conversation.  

(Please note, names have been changed to respect the privacy of those involved.) 

Evie was looking to book a last-minute summer getaway. So, she hopped online to find the perfect space. Soon, she found a quaint cottage that met her needs, and she started instant messaging the property owner. Little did she know she’d have to handle a difficult conversation that, if responded to in the wrong way, could ruin her entire trip and cost her hundreds of dollars. 

The property owner, John, was friendly and helpful. He shared that he had two spaces for rent on the property Evie was looking at, an RV and a cottage, which were both available. Evie said she was looking for something private, and if he was renting the RV and the cottage separately, she wasn’t interested. John graciously offered to book both spaces for her and only charge her for one. This way, she wouldn’t have to share the property with anyone and would have the privacy she preferred. How perfect! She agreed to rent John’s property. 

Let’s fast forward to the week before Evie’s holiday. 

John reaches out to Evie to confirm last-minute logistics: What time will you arrive? You can find the key here. Make sure you check out this restaurant. Then, he casually mentions that he will be staying in the RV while she’s at the cottage next week. Evie is confused, and a bit upset. This isn’t part of their original agreement.  

What can she do? If Evie cancels her reservation, she risks losing her deposit. And she won’t have enough time to book something else – her vacation would be ruined. 

Evie needed to craft a response that explains her feelings and reminds him of their original agreement. She had to do this in a clear and respectful way, through instant messaging. If she got it right, John would realize his error, and she’ll be able to enjoy her trip with the privacy she wants.  

Evie uses two strategies to write her response: 

First, she is direct when she reminds him of their original agreement: 

• She refers to the exact date and time of the message with the agreement 
• She reminds him that she was looking for privacy, and she booked his location because he could provide that 
• She shares that if they can’t keep the original agreement, she’ll have to cancel her reservation 

Second, she maintains a friendly, positive tone throughout her message: 

• She uses a buffer by thanking him for confirming details 
• She avoids negative trigger words 
• She uses please and thank you to be polite 

She asks me to read her response and make suggestions. She also reviews her message again to make a few last edits and corrections. Then she sends it. 

Evie nervously waits for John’s response.  

She doesn’t wait long. He sends a message within seconds and… 

He apologizes! He completely forgot their original agreement. He’s new to renting and manages three properties. He will, of course, follow their agreement and give her both spaces. He thanks her for reminding him and hopes she will still come.  

Evie is thrilled. She dealt with a difficult conversation successfully. She still gets to enjoy her private getaway, didn’t lose money, and maintains a positive relationship with the property owner. 

The strategies Evie used in this situation are helpful for dealing with bad news or difficult conversations in our digital world. When we respond with a direct and clear digital message that also keeps a positive tone, we preserve relationships and maintain a respectful image.