"How to navigate bosses behaving badly..."

October 14, 2026
⏱︎
13:11

A Nonprofit Diaries favorite is BACK to help you navigate bosses behaving badly! In her first episode, we heard how Cindy's boss ambushed her on a long car ride, and she was so rattled that she forgot to lock her car, which was later stolen. Now, she's spilling the tea on more managers gone rogue..... and offering advice on getting through these moments with your professionalism intact.

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 we've got a take two on a guest that I cannot wait to have back for more stories. My dear friend Cindy Wagman, who is just a badass woman in our industry who I absolutely admire and just love hearing her story. She's such a good storyteller and she's always got a lesson. She is the founder and CEO of the Nonprofit Fractionals Network, which is empowering nonprofit professionals to do fractional work for other nonprofits so that they can take their life back and so that those nonprofits can also have a wealth of experience on a temporary basis for what they need. So, Cindy, thank you for coming back to the podcast with more stories. My pleasure. I'm so excited. I'm so excited. So the last time we saw you, we talked a little bit about um maybe maybe part of the reason, right, that you pivoted into doing what you're doing now, which is sometimes when you think you have a leader in your corner, they're not always actually in your corner, or they're just really not there at all. And that really kind of frames how you move through the industry in terms of is your leadership you know really working for you as an employee or against you. And unfortunately for you, but fortunately for people listening, because there are lessons to be had here, you've had a few bosses behaving badly in a non-profit. So last time we talked about, you know, one that kind of ambushed you into a conversation you weren't ready for, frazzled you so much that you know you forgot to lock the car and the car got stolen. That's crazy, but that's one of many. So, in terms of other lessons you've learned from leadership that have not behaved the way they probably should, what do you have for us, Cindy?

SPEAKER_00 1:53

Oh, I mean, I feel like there's so many. Like one time, um I so we were talking before we were recording about tattoos, and years ago I had a tattoo on my foot. Everyone thought was very cute. I didn't actually like it. That's another story. I'm having to tell if you want. Um, but it was, you know, a cute flower tattoo. And my boss, we were going into a meeting, and I was wearing kind of crop pants and heels, and she looked at me, she's like, I need you to go to the store and buy stockings and cover your tattoo. Oh, I'm like, what? Like, this is you know, maybe the 2010s, like mid-2010s. Okay, it's not 19. No, no, no, 20, 20, like the mid-2000s. Let's say 2000, no, goodness, why am I my okay? I left that job in 2010. So sometime between 2005 and 2010. Um, so it wasn't that long ago. No, um, but yeah, she just was like, and she had these little ways of kind of not like putting people down, but like putting people down. Yeah. Yes. Aggressive little comments. Yeah. Yeah. Like I remember also going in for my job interview, and I'd known the organization, like I'd volunteered with them before and known them and knew her, who ended up being my boss. And I think it was before after the interview. She looked at me and she said, I had a dream that you should up to this interview in jeans. Um, like I like I would have been completely underdressed and like unprofessional. And I was like, So what are you telling me? Like, are you telling me you don't think I'm qualified for the job? Like, what what is what's the purpose of this story? Like, there's so many examples throughout my career, and I think for most of us, where um people just like you know, say something that isn't the nicest or like isn't mean, but can feel mean or undermine your own confidence. Exactly.

SPEAKER_01 4:19

And well, so now that you are you're your own boss, right? But you're also in charge of a company that empowers people to do their own work and those types of like you are a leader in your own right. How do we as leaders avoid this kind of like what kind of audit can we do to make because I don't I I can't, I I'm gonna give this these bosses the benefit of the doubt and say that there wasn't this intent to be malicious, right? They're not trying to be a bad guy, but yeah, how how do we avoid this kind of you know, kind of harmful rhetoric that we might be consciously spewing at other people?

SPEAKER_00 5:00

So I think part the way I've approached it now in my like since then, after I feel like I've learned a lot. The first thing is understanding in my experience, the people who behave like that are deeply insecure. It's usually a reflection of them, not you, right? Yeah, yeah, exactly. And so some I just with that take what they're saying as a grain of salt, and people who are insecure tend to put other people down so that they feel more secure in their role, right? And so oftentimes it has nothing to do with you. Now, that being said, we still take these messages with us. If we hear them enough times, they become these little stories that run around in our heads with our permission.

SPEAKER_01 5:57

So, my question for you, because this is an honest question. I would love your advice on this. Is there a way to respectfully challenge them so that we kind of get out of this habit of being the yes people, right? And even if it's not in the moment, right? Because so many times I'll go, man, 30 minutes later, I know exactly what I should have said. Oh, yeah. I had thought that in my brain, but you know, your brain's not maybe in that mode in that time that happens. A way to revisit that conversation. Because I think what allows us to rent, you know, keep that narrative renting space in our brain is the fact that we never kind of go back and say, wait a minute, that's not reality. Yeah, you're wrong. Here's the receipts to show you why I am right. I'm not just saying I'm right because, you know, I'm delusional. Have you found a way to either in the moment or later go back up to that person and be candid and say, This is, you know, how I feel. This is how what you said made me feel. Is there a version of that that people can employ themselves?

SPEAKER_00 7:05

Yes. And I would say it varies depending on where you are in your career. So early on, and oh, that like, oh, I should have thought of that is the worst feeling because we sit with it for like days sometimes. I've heard that. But yeah. So regardless of where you are in your uh experience, let's call it on the spectrum of experience. The best thing I would say is give yourself space. So very often we are like, sure, great, I'll do that. If you can say, let me think about it, like, you know what? That's interesting. Let me come back to you with some thoughts. Um anything you can do to give yourself space or continue the conversation. I teach this also in business development with people who are like, and I actually used to teach this with fundraising. If someone asks you a question and you don't know the answer, it's okay to buy yourself time and space to get back to them. So, same thing. Like, you don't have to be perfect, you don't have to have all the answers, you just have to practice space, pause, think about it, say that's interesting. You know what? Let me think about it and get back to you. Or I haven't thought of that. Let me get like I'll come back to you with an answer. So that's the first thing. Because we never think of the right thing. I never think of the right thing to say.

SPEAKER_01 8:41

No, oh there, I'm there with you.

SPEAKER_00 8:43

Yeah. Now, early in my career, I think you and for most people early in their career, you kind of have to back it up. You have to be like, okay, let me bring the research, right? Bring the receipts. Here's what I learned, here's where I found it, what have you. Now, as you get further into your career, you have the experience, and it's more along the lines of, and I teach us with the fractionals I work with, which is saying, like, you brought me on to be the expert on this. This is what I'm telling you as the expert. And I have had to do that with clients. I said, You brought like this is what you asked me, this is why I'm here. I need you to try it.

SPEAKER_01 9:33

I love reminding people why you are where you are. That's such a good piece of advice to be like, remember, bored woman, or whoever you are, you brought me here. Why did you bring me here? Because I've done this. And because I am smart and I know this organization and I know this work. I think we're so often afraid to say that because it sounds like bragging, but it's not. It's just reality. Like, this is absolutely why you are sitting in the seat that you're in. And sometimes we just forget that. We're like, we feel like everybody around us is so much more competent than we are for whatever reason, which is just absolutely not the truth. And it does help when you have leaders who support you and remind you of your value, but we can't count on them, as we've learned through your stories, that you are responsible for being your own champion, and not just for the sake of you know, throwing yourself a party, but because you've earned it.

SPEAKER_00 10:35

That is like the number one thing I'm so like hyper fixated on teaching my kids. I say to them, like, you can control other people's behavior, but you always have a choice on how you respond and react. And so I'm like, if you learn anything, so I like kind of hack this idea of like whose brain do you hear? And I'm like, that's the that's the message I want you to hear in your brain when you grow up is like you can control other people, but you always get to control how you respond.

SPEAKER_01 11:08

Exactly. Yes, I love that. And it really gives you ownership, right? It makes you feel empowered to do what you need to do rather than being at the mercy of someone else's opinion or actions. So I hope that your kids, absolutely, but all of us adults or you know, kids at heart, because we all feel, you know, I still don't feel like the adult in the room and I'm in my brain. No.

SPEAKER_00 11:26

No, I'm like still 25. Oh, in my brain, yes, absolutely. Um, you know, my still with my like high collect, no, I have like high blood pressure and everything. I'm like, yeah, no, I'm still 25, right?

SPEAKER_01 11:40

Yeah, right. I will think that, you know, till the day I die. So yeah, but but I love all of thank you for sharing first of all the vulnerable stories. I realize we all kind of like collectively sigh and chuckle at these things. This is a version of reliving some trauma, right? These were hard moments in the moment that taught you something. So I always appreciate people coming and reliving those for the benefit of other people. So, first and foremost, thank you for sharing all of these little jewels and nuggets that you have in your treasure chest of experience. It really does, I think, make us all feel more connected and feel like, okay, I'm not the only one. And not only am I not the only one, but this is a really good like nugget for me to remember to how to move through these motions moving forward. So appreciate you being here multiple times. And take your very valuable time to share your stories. I would love to have you back. Keep collecting those good stories because this is what we're here for. We're just here to to collectively breathe and laugh and vent and and all the things. And you've really helped us do that today. Thank you. Yes, absolutely. Well, Cindy, thank you for being here. Everyone on the podcast, thank you for listening as always. This is your reminder to hydrate and practice self care. Please take care of yourself. And if it's going to help you move through your career and your life, there's a link in the description where you can submit your own diary entry so that you can relate to the nonprofits around you as well. We would love to have you on the podcast. So I hope you do that, and we'll see you all next time.

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