Make a Difficult Conversation Less Difficult

February 24, 2025

Recently a mentee of Stephanie’s, Sara, came to Stephanie looking for advice on a problem she was having with a  new team member. As a marketing lead for a new product, Sara is building out a team that is a little non-traditional. Because the brand she promotes is anything but corporate, she wants her team to lean into a more grassroots approach to building brand awareness and promoting the product. As such, she hired women in their mid-twenties to spend a year traveling the world and promoting the brand and its products by talking about their lives (and their use of the products) on their social media accounts. 


Since the project began, Sara has learned that these women have a different approach to work than she does. Sara comes from a corporate background and expects a certain corporate professionalism from her team members. When she sat down for a monthly one-on-one with one of the women, Kate, she was surprised to see Kate show up for the video call 10 min late and in her sports bra. To top it off, Kate used the time during the one-on-one to record a #GRWM (Get Ready With Me) video for the Instagram account, so the whole time she was talking to Sara, she was also putting on makeup and trying on outfits.


Sara came to Stephanie looking for advice on how to handle the situation. “I know that Kate comes from a different background than I do, and I want to respect the fact that she was literally creating content while on the call with me—the exact thing I hired her to do—but I can’t help but feel like she doesn’t respect me and her level of professionalism is lacking. How do I address this without making Kate feel like I don’t appreciate what she does?”

This is an age-old question. How do you give feedback to someone?


Nine times out of ten, feedback conversations turn into difficult conversations because we build them up in our heads to be way bigger and more complicated than they really have to be. Here’s some of the advice that Stephanie gave Sara. What else would you offer?


Immediacy is best


A quick comment delivered in the moment is much easier, both to deliver and receive than a long-awaited conversation. As soon as Sara sat down for the one-on-one and noticed that Kate was in a sports bra, she could have said something simple and straightforward like, “Oh! I see you’re in your sports bra! I’ll wait while you put something on.” Then, the trick is to make nothing of it after that. It’s a quick moment that immediately passes, but the signal that coming to a one-on-one in a sports bra is inappropriate is communicated.


Make it bite-size


Sara mentioned that she simply couldn’t think fast enough in the moment to respond right away. She would have loved to deliver quick and immediate feedback, but she was so flustered, the moment got away from her. So now what? It was two weeks later, and she still hadn’t said anything to Kate.

Stephanie’s advice was to keep the feedback small. Waiting until a whole pile of issues came up, and addressing them together only makes the conversation harder to have. If Sara felt like the sports bra moment needed to be addressed directly, then she should address it without compounding it with 14 other things that had also happened.


Get curious


With our love of coaching, this is always our favorite advice to offer. Most of the time, there is more to the story than we see. Stephanie challenged Sara to approach a conversation with Kate not as a moment to “teach” Kate anything specific, but rather as a moment to learn more about Kate. They brainstormed a few powerful questions Sara could bring to Kate to better understand where she’s coming from and what her thought process and motivations were:


  • What do you see as the purpose of our one-on-ones?
  • How can we maximize the value of our one-on-ones?
  • What do you hope to bring me during our one-on-ones?
  • What do you hope I bring you during our one-on-ones?


Focus on the behavior, not the assumptions you draw from behavior


One of the key challenges Sara was having was that she had interpreted all of Kate’s behavior to mean that Kate didn’t respect her. This is a story Sara was making up based on how she chose to read into Kate’s behavior. But the truth of the matter is, conflict almost always comes about from misread or misinterpreted signals. Stephanie encouraged Sara to pin the assumptions, and check her story. One way to do that is with the script, “I noticed that you [insert objective, observable behavior]. The story I’m making up about that is [insert personal interpretation]. I’m sure that’s not what you intended. Will you set me straight?”


This approach opens the door to a productive conversation that isn’t accusatory, and stays focused on the behavior (something fixable)—not the personality (something more akin to identity)—of the person.



What advice would you give Sara?

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