"The awkward wardrobe conversation I wasn’t trained to have...”

September 30, 2026
⏱︎
14:40

It was an awkward conversation no leader wants to have... Early in Jamie’s career, an unexpected wardrobe issue at a fundraising event meant sharing deeply uncomfortable feedback with an employee. Jamie explains how she approached the conversation with care... the question she suggests asking when there's a power dynamic in the room... and the lesson she learned about the quiet loneliness of leadership.

Transcription

SPEAKER_01 0:07

Hi everyone, welcome to the Nonprofit Diaries, where we share the stories that don't make the newsletter. I'm your host, Kimberly Bottom, and this week's guest has occupied a variety of roles at various nonprofits over her 20-year career. She is now the CEO of Girl Scouts Texas, Oklahoma Plains. And the journey to get where she is came with a lot of lived experiences and lessons that frankly nobody prepared her for, which I feel like a lot of us can relate to. Because so often in nonprofit work, there isn't formal training for becoming a leader. You just work hard, advance within your organization, and you figure it out as you go. So Jamie's experience with this process began with a fundraising event about a young employee and some feedback that no manager ever really wants to have with a person, but you have to do these things sometimes. So nonprofit Diaries Family, please welcome Jamie Williams to the pod. Jamie. Thank you so much. I'm so excited to be here. I'm so excited for you to tell this story because I feel like the awkward nature of the conversation is the reason people don't talk about it, but everybody goes through it. So, like we need to have these conversations. So I I do want to caveat before we dive into your story, Jamie. I want to preface this conversation to say that we are intentionally keeping some details out because what we don't want to do is identify that young employee that Jamie was managing. The point of the story is not calling out mistakes, it is recognizing that these challenging moments will inevitably happen to every single one of us. And the way we respond is what shapes the kind of leaders we turn out to be. So that is the preface of the story. I want everybody to be super clear on that. So now that we've got that set in stone, Jamie, early in your career, you had just moved into what was kind of your first like leadership position, right? Where you were directly managing people and there was an awkward situation at a fundraising event. So tell us what happened.

SPEAKER_00 2:04

Yeah, so I had just I had been in a role um with direct management responsibilities for the first time and hired in this new staff member. And honestly, she was lovely. Everything about her was she was a high performer. Um, she wanted to be great, she was super mission-focused, detailed. Um, and so we were preparing for an event together, and it was kind of a kooky event that was one of our signature events at the organization. Um, but it was supposed to be a lot of fun. We were dealing in a very serious subject matter. Um, and so we tried to make this event just lively and have a lot of personality. And so on event day, um, she was the person that was really responsible for coordinating the logistics and making sure that the event was really entertaining for participants. And during the event, I got a call from a friend who was on site who let me know that um her warp dro wardrobe choices were maybe not what we would have expected. So part of the event really was incorporating some level of costume. Um, and she was wearing a skirt and didn't necessarily think about that she'd be like climbing trees and doing some of those things, um, and failed to wear undergarments that day. And so it's typically something you wouldn't know if your employee was making that choice. Right. They're climbing a tree. It's windy outside, and now the entire event um participation base knows what her choices were related to undergarments that day. Yeah.

SPEAKER_01 3:53

Yeah, exactly. And I mean, thankfully, it sounds like that employee was letting you know out of like, hey, I, you know, obviously I'm looking out for this young employee. Like, she may not be aware, right, that this is an issue because again, maybe she's nervous, it's her first, whatever it might be, right? She's probably on. Absolutely.

SPEAKER_00 4:11

Absolutely. It was someone I think who felt like they wanted the event to be successful and they knew that that image maybe wasn't in line with the vision that we originally had for the event. And then I think also recognized just from a management perspective that that our employee would really benefit from some coaching long term about thinking through some of these things because that's something that could harm you if you continued to make those decisions.

SPEAKER_01 4:37

Absolutely. So, so you're a new leader, you've got this fundraiser, it's happening right now, right? So you're probably in hair on fire mode, right? And then you get this feedback. What did you do with that information? How did you process it internally? What did you, what were your next steps?

SPEAKER_00 4:51

Yeah. So I had to find my way to her, and it was a really large event space. Um, call her down from the tree, and then ask if she had any like backup costuming or like someone she could call to help um at that time, just kind of briefly highlighted what the challenge was. But we're in event mode, so now is not the time to like address. It's like what's the solution? Um, and so she was able to find a solution for that. And then ultimately when we returned to the office um the next Monday, we had we had to have a little chat. And, you know, it was really uncomfortable, not only because it of the subject matter, but also because we had a great relationship. Yeah, sometimes the performance management conversations, if there isn't, like if there's a lot of things going on, you it's easier to give feedback because you're like, oh gosh, well, you know, some of these things have been hard. We've been having ongoing conversations. Up to this point, there have been no conversations other than you're doing a great job. Yeah. And really not wanting to like kill her excitement, didn't want to damage her permanently. This is clearly something that would be embarrassing for someone. Um, and so just having that one-on-one conversation, making sure that no one we didn't, we were small enough, we didn't have HR. So there was no HR department involved. It was just me and her one-on-one, and me just sharing that. Like, of course, she knew that it had been brought to my attention because we had a wardrobe change, but like, but I wanted to help her think through like for future events or just coming to work. What how do we want to show up? Um, what that looks like, and some of the things that we need to consider that maybe we wouldn't necessarily consider outside of the work environment.

SPEAKER_01 6:54

Yes. I really appreciate that approach because this is deeply personal feedback for someone that you care about and want to champion. Like you said, this isn't a disciplinary, I think we need to part ways. This is everything's great, and this was just a, you know, a judgment misaligned. Like it probably wasn't even something she realized was happening. So the approach it sounds like you took was to sort of zoom out. Is that right? Where you kind of said, All right, taking us out of the moment. We already addressed it, we fixed it in the moment. What was your approach going into this conversation to make sure she knew that she was cared for and safe?

SPEAKER_00 7:26

Well, I think first it was just acknowledging the like the mutual feeling that this was it was mortifying for both of us, right? Like I'm a human too. Yeah. This is a really hard conversation to have. It's not a reflection of performance or anything else you've done in the organization. It's not a reflection of what your future is in the organization. Right. It's just maybe a judgment conversation that we weren't expecting to have, but maybe it, you know, we're having it now. And so trying to keep it kind of light, right? So that it was comfortable. It wasn't a disciplinary conversation. It was like uh this was a mistake. And we're gonna give you a little grace. Um because that's what I would hope for if I made the same mistake. And I'm not gonna make you sit in embarrassment. Like, let's keep this brief. Let's talk about how we move forward and and be done with it and not reflect on it again in the future.

SPEAKER_01 8:30

Yeah, I feel like the the keeping it light is such an important thing that maybe we forget because these these situations can feel heavy. But what's that quote? I'm gonna misquote it, and I can't remember who said it, but I think it was it was a very powerful woman, but she said, you know, nobody can make you feel embarrassed without your permission, right? And that's like we treat the way we treat a situation dictates how the situation unfolds. So when you go in and say, Man, this is weird, it feels like it just it releases the tension in the room, right? So as a leader, just acknowledging that like we don't we don't want to be here, but let's just get through it. That yeah that that for some, like I would feel safe, right? And in that scenario. So I really love that. And we when we chatted about this briefly, and like now that that moment has passed, there have probably been many moments since, right? That were sort of maybe not that awkward in nature, but like you have to have tough conversations. It taught you something about leadership, and there's a a hint of loneliness in that lesson. So touch on that a little bit.

SPEAKER_00 9:32

Yeah, I think um you learn pretty quickly as you grow in your leadership journey that your your peer connections become much less, right? So, like even following that incident, that was something I had to keep to myself for her sake. Like I couldn't go with my friends after work and chit-chat and share like what had happened um and how terrible that was for me because it could impact her career. And um, and that becomes truer, I think, even the more we grow in our leadership roles, the more isolated we become, where maybe you don't have colleagues as a CEO. Like I don't have a person that's sitting next to me that's at of even rank within the organization. So oftentimes there are things that are just like, gosh, that was really hard. And the only person I can talk to about it is my therapist.

SPEAKER_01 10:31

Right. I feel that, right? Like sometimes I feel bad about you know what I have to say to my therapist. I'm like, well, I'm paying you. So at least there's that, right?

SPEAKER_00 10:43

Um there's confidentiality and like all the things that I need to protect this person. Yes, absolutely. Exactly.

SPEAKER_01 10:51

But I mean, to your point, on the front end and the back end of these learning experiences, whether it's having awkward conversations or anything else that comes with learning how to be a leader, you can't go to like a cohort before and ask, like, what should I do? And then after it's over, you can't go unravel it and like talk it through. It can be really isolating. And then you're wondering, did I do the right thing? There's no feedback. So, like, as now that you are a CEO and you've been in leadership positions for many years, is there anything, whether it be a resource or like a frame of mind, or maybe it's, you know, go find a good therapist, whatever it is, yeah, that you would suggest to somebody that's feeling that loneliness right now?

SPEAKER_00 11:32

Yeah. I I do think it's always okay to ask for feedback, even in those uncomfortable conversations where there's a power dynamic. Yeah. I didn't at that time. I think now if I was coaching, I probably would say, like, tell me how this conversation was for you. How can we make it better? Um, and then yeah, I I think that in the leadership role, we have to have mental health support in a very formal way because there is a whole team of people that is dependent on my stability. And so I have a responsibility to show up where I'm managing my own mental health. Um, and so I think that that's a really important resource for managers, no matter what level you're at, is you have to be really cognizant of your own mental health because it bleeds into everyone else's. So when I'm having a bad day, I have to be really self-aware to make sure that I don't cause everyone else to have a bad day.

SPEAKER_01 12:33

That's so hard to get outside of yourself to see that and do that. I just had a conversation with another podcast guest who's a mom, and she's like, at the end of the day, I'm like, oh, that tone that I took with my kids, that was not something that they deserve, right? Whatever that you just these things that, unless you start to look inside and inward, you're gonna miss, and it is going to affect the relationships and the leadership that you're that you're presenting on the outside. So it's such an important reminder that everybody's now saying, and I'm so glad that like take care of yourself is the new cool. Like, let's make that right. But I'm so I'm so thankful for you to say, like, hey, I've lived these experiences, and this is probably the thing that's really gonna help people be better leaders, which is to focus on yourself first. It's not selfish, it's it's what you need to do.

SPEAKER_00 13:20

Yeah, yeah, absolutely.

SPEAKER_01 13:22

I feel that. Well, I appreciate you coming on when we were chatting about this podcast. I remember you you were so careful because you're like, this is not about um shaming an employee. That is not the purpose of this conversation. And I was so thankful for your realization of that and your awareness of that, because there's a really important lesson here to talk about the awkward things that nobody wants to talk about because everybody goes through them, but you have to do it with with ethics and care. And you've definitely done that today. And I really think the story is going to make somebody go, oh, this one time. Yeah, I didn't, I didn't know what to do. And now, you know, this is probably a way I could handle it, and it's just gonna make everybody feel a little less alone, a little more supported. So that loneliness you felt, you are enabling other people to not feel that. So I'm really thankful for you sharing that with us today. Well, thank you for the opportunity to share. It was fun. Yes, it was fun, it was super fun. Well, everybody out there listening, this is your weekly reminder to hydrate and practice self care. I feel like every time we talk, I have a conversation now, like that that tagline just gets more and more important. So be sure to do that. And I can't wait to see you all again for our episode next week. Thank you all so much for joining us. Have a wonderful rest of your week. And thank you, Jamie, for being here.

SPEAKER_00 14:38

Thank you, Kimberly.

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