Can We Talk? A Guide For Difficult Conversations

How To Navigating Difficult Conversations At Work And At Home

So you’ve got that big meeting next week with Mr.DontGetAlongWith at work or you need to have a difficult conversation with your girlfriend because she keeps doing “that thing” that really makes you feel like crap. What do you actually say? Here are some suggestions for a more effective outcome.

Work Conversation:

Create the space. Try to think when the best time for discussion would be. Do they have a big event they are planning for this week? Are they dealing with some contract issues? Step into their world and do your best to determine when a good time would be.


Request a time to speak via email. This keeps it low pressure and non-confrontational. 

You: Hi (name), I’d like to know if we can set up a time this week to talk about the investor event last Thursday? I had a few questions. [Tip: Yes, there are a ton of things you want to get off your chest with this person but, you need to go with the most recent and clear example of when the two of you were not on the same page] 

Them: Sure, how about Wednesday, 2 pm?

You: Great. Thank you, I will book a room and send you a calendar invite. [Tip: By booking a room, you are creating a neutral, private environment. You can also go to a location outside of the office, but choose a space where you can be expressive and not worried about curious ears sitting next to you in a coffee shop. Also, by sending a calendar invite, there is no need to send a reminder.]


You: Thanks for taking the time today. I want you to know I’m really enjoying my role as Department Manager and the new challenges it brings. There is something I want to bring up that I think we can improve on. In our event debrief, you were quick to point out all the things you felt the team did wrong. They worked tirelessly to have a successful event and, yes, since it was our first event, we did have a few AV issues that we fixed in a timely manner. The team has felt deflated ever since then, which you have likely noticed, and I believe the solution is creating a better system for feedback. What I would suggest for the future is that you start with what you liked about the event and then move on to areas of improvement. You don’t need to sugar coat anything, but I believe it is just as important to praise as it is to critique when building effective teams. I think this habit can be brought into both our email and in-person communication. What do you think? 

Them: I’m a bit surprised by this because I thought I did provide some good feedback. If the team is feeling deflated, that isn’t a good thing. We have a lot more of these events to produce. I think what I’ll do is review my notes from the event and email them over to you and you can share them with the team. I’ll add in some notes on what I thought did go well. 

You: Thank you, that will be really helpful.

And then let the conversation end. Yes, there are other things you want to bring up with this person, but first, work together to solve one small issue. Once that is a success, things will get easier. 

Personal Conversation:

Create the space: Make sure you don’t bring up difficult conversations while one of you is driving, watching TV, or engaging in some other activity. You want to both be fully present and it’s worth making the effort to create that time. 


You: Hey, there’s some stuff I want to chat about with you regarding what happened at my parents’ place the other night. When would be good for you?

Them: Are you mad at me?

You: No, I’m not mad at you. I just want to chat about how we can make weekly dinner at my parents’ place more fun. 

Them: Okay, how about when I get home from work today? 

You: Sounds good, I’ll pick up some dinner we can have after. [Tip: saying something to this effect makes it clear this is not a break up conversation, which is everyone’s worst fear when asked “to talk”. That’s why the term “chat” is better for these lighter circumstances.]


You: I’ve been thinking about  dinner last week and it made me realize how important it is that you respect and get along with my parents. I know they aren’t perfect, but when you lean in to me with under-your-breath comments, it really makes me uncomfortable. I know you are doing it to connect with me but it makes me feel bad. [Tip: You are showing that you see both sides and why you guess they do it.]

Them: I thought we felt the same way and that you liked poking fun at your parents. Why do you always laugh then?

You: I laugh because I’m trying to make everyone happy. I just realized that it’s not really respectful to do that and I want us to make an effort to stop doing it. I don’t expect things to change overnight, but I want us to make the effort. [Tip: Use “us” language to show the two of you are remaining connected and working to do better together]

And then the conversation continues from there. Happy healthy conversating!