Is Texting Appropriate for a Difficult Conversation?

There are so many ways to communicate today!

Really, the possibilities for kicking off a conversation with someone are endless. We can reach out to others via email, phone, voice message, video chat, online work platforms such as Slack or Basecamp, and, perhaps the easiest of mediums, the text message. Given all the options, some mediums are better than others for effective communication and a lot depends on context. For example, is texting appropriate for a difficult conversation? Let’s think this through.

Those of us who are of a certain vintage will recall an episode of Sex and the City where Carrie reveals to her gal pals that her boyfriend just broke up with her via a Post-It note. All agreed the act was appalling. Carrie laments that it seemed only yesterday that it was inappropriate to break up via the phone. Oh 2008, weren’t you quaint? 

So many of the lines have moved over the last decade when it comes to communication and how we choose to do it. But maybe the guidance for what message matches which medium is more static than we think. Breaking up a long-term relationship via a Post-It note in 2008 is likely about the equivalent of sending a text message today. Most people would agree that this type of conversation calls for you to show up in person under most circumstances.

So, when is texting appropriate for difficult conversations?

Generally speaking, carrying out a difficult conversation through text messaging is not the best. However, there are always exceptions.

For example, several years ago, when hanging out with a group of friends, one of them said something to me in a way they thought was good-natured teasing but to me sounded more like bullying. The remarks involved a topic I am pretty sensitive about, and they hurt me.  I let it go at the time, but the friend repeated a variation on the comment to me the following two times we gathered as a group. It wasn't funny to me, and I knew I had to put a stop to it, or it would jeopardize my relationship with this person.

I felt awkward about initiating the difficult conversation I needed to have with my friend, and I suspected they would react defensively when we did speak.

I decided to send the friend a text message to succinctly relay the issue, adding that I wanted to meet in person to discuss it. 

Using a text to set the context of our discussion had advantages. It allowed me to compose exactly what I wanted to say and let the friend process the message and prepare for the conversation ahead.  The text was a way to begin the discussion and smooth the path to an in-person exchange. 

The approach worked well in this case, and we were able to retain our friendship. The in-person conversation was still tricky, but I think it benefitted from starting with a text message because it allowed us to process our feelings and prepare for the discussion. The two disadvantages of sending a text I have reflected upon since this incident are my friend could have received it at a bad time, or someone else nearby or with access to the phone could have seen it. Hindsight, being what it is, I could have used another text-based medium to avoid these potential risks and still achieve the same outcome. It was fortunate that neither of these concerns played out in my case.



The following is my take on the myriad options we have today for dialogue with others and what to consider before using them:

Face-to-face (in person and online video)

  • It’s an immediate form of communication. There is no lag time between those conversing.

  • Best for nuance because you can see facial expression and body language.

  • Offers immediate opportunities to clarify the message and correct assumptions.

  • Asking to meet face-to-face conveys respect and a certain weight to the importance of what you have to say.

  • In-person conversations provide the opportunity for physical exchanges such as a hug that the other person might find comforting.

  • It can be difficult for some to find the right words without preparation

Best for: Clearing the air when a resolution to a difficult problem or situation will require careful listening and responding. Also suited to delivering difficult messages

Phone (voice)

  • It’s immediate and next to a video chat, it’s the next best thing to being with someone to deliver the message. 

  • Participants can’t see each other so facial and body language are not accessible to give your message nuance. 

Best for: Times when you can’t have an in-person conversation or when not being directly in front of the person might increase your ability to convey the message because of the distance it provides.

Mail (electronic or physical note)

  • It’s asynchronous and means there are potentially gaps of time between responses.

  • With email, the recipient could miss your message because of in-box overload or spam filters. Letters can also get lost in the mail.

  • Without hearing someone’s voice or seeing body language, it is exceptionally easy to make erroneous assumptions about the message and the implied meaning behind words.

  • You can never assume your conversation will remain private due to tampering or hacking.

Best for: When you want to deliver a precise message that you craft carefully and you’re concerned you won’t be able to do this in person. A written message might also be a suitable way to invite someone to have an in-the-flesh meeting while giving them context for the difficult conversation to come.

Text message (including work platforms that include chat)

  • Conversations can be synchronous or asynchronous.

  • Comes with many of the limitations of mail or physical notes.

  • With so many online and digital chat platforms it's a very accessible way to converse.

  • The recipient of your text message may get it at an inopportune moment. 

Best for: Similar to mail -- a text message might be a good way to start a conversation but you might need to take it in-person to make the exchange effective.

Getting someone else to deliver your message

  • You have little control over how your message will be delivered,  which could create misunderstandings.

  • You might be putting someone in an uncomfortable situation being placed in the middle.

  • The person receiving the message might feel hurt if you didn’t come to them directly. 

  • You save yourself the discomfort of initiating the conversation

Best for: On the face of it, getting someone else to convey a message on your behalf might seem like a bad idea, but in some contexts, it can ease a difficult conversation. Take, for example, asking a friend or family member to tell your network of friends that you have experienced a death of someone very close to you or a pregnancy miscarriage. The trusted person can let your network know what you’re going through, and if you’d prefer not to discuss it right away, they can tell them that too. 


I’d love to hear about what’s working and not working in your conversations!