EP 286: Being difficult made me better with difficult people
16 Apr 2026 · 10 min
Natalie Fisher was jealous of a charismatic new colleague and gave her the cold shoulder. The colleague kept asking her to coffee, acknowledged the tension directly, and asked for a professional relationship without demanding friendship. Natalie said yes, they became collaborators, and it taught her that difficult people respond to vulnerability and persistent, gentle asks.
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Welcome to the Outrageous Workplace Stories series of the podcast. In these episodes, you'll see ways to handle even the toughest of workplace situations with power and impact while making humanity a priority. These stories shaped how I went from receptionist to HR manager in 4 short years without a degree, without the qualifications or experience that you would've thought I needed. This series is designed to help you turn everyday challenges into momentum for your next level, no matter where you're at right now. If staying grounded in your humanity and being true to who you are as a person is important to you, yet you also want to get to your next level, you want to earn more money, and you want to create a professional life you're proud of, that is also at the top of your list. I'm here to tell you that you can do both. And this is where you start. Let's go.
Hey, so welcome to the next one of the 13 work stories that you wouldn't believe happened. This one's a little different. Um, I was working in a place where a new woman came in, and I was honestly quite jealous of her. She was very pretty, she was very like magnetic, and everybody loved her, and I Just was jealous, and therefore I didn't want to help her, and I didn't want to be nice to her. And so she would ask me for things, and I would kind of like not really give her the answers, or like brush her off, or like kind of tell her to go look somewhere. And we ended up actually having a good relationship in the end, and it was because of her, because of what she did. And I think that the way she handled me, the difficult person, was worth noting, and it made a difference for me in my career later. So she picked up on the fact that I didn't like her. She knew this. And so she asked me to go for coffee. She's like, look, I know that— I don't— I mean, she's— it was something— she sent me an email. It was something along the lines of, look, I know we haven't really gotten along and you don't really know me, so I was wondering if I could invite you for coffee, um, and we could have a chat. And I was like, no, you know, I don't really have time for that. I don't really want to. And she just kept persisting. She's She just kept saying, "Hey, look, I know maybe you have time this afternoon. How about Friday morning?" She's like, "I know, like I have my favorite place, the Dolce Vita. I will take you." She's like, "She's like, I'm not looking for anything. I just want to have a chat." And she's just, you know, she kept persisting, made it low pressure. So eventually, I couldn't really keep saying no. I felt like I kind of had to. So I went, and basically what she said is she's like, "Look, I know you don't really like me." But I would really appreciate it if we could have a decent working relationship. She's like, we don't have to be friends, that's okay. She's like, but it would really mean a lot to me if, you know, we could have a professional relationship where we can help each other out. She's like, because honestly, I would like to be able to help you, and I would like it for you to be able to help me. And, you know, that's just what I would like. And so she presented that to me. And I was like, Sure. I'm like, I didn't want to, and I still didn't really like her, and I was still dealing with my own jealous feelings. But the way that she presented it to me, it was so human. It was so open. It was so like she wasn't asking me for anything more than what I already should have been doing, right? I already should have been the decent human being that got over my jealous feelings and helped her. And so I was—it was very difficult for me to say no to her ask. So I ended up saying yes. And then she kind of pushed it a little bit and she's like, yeah, maybe you want to come to a yoga class with me sometime. And that I was definitely not into. And I was like, well, you said we didn't have to be friends. But I did, I was definitely different towards her after that. So after that, I did help her, I was more collaborative, and, and she made more of an effort with me as well. And the thing that this story really points out is that somebody can be very difficult, they can be very negative, They can be very non— like, they can be walled off, and you can still get through to them when you make it like it's unreasonable not to, right? Like, if someone's like, I would really like it if we could have just, you know, a professional working relationship— like, she phrased it like that. She's like, she's like, working relationship. She's like, we don't have to be friends. I get that you don't like me. That's okay. And then when someone does that, or someone says that to you, It's just really hard to be like, no bitch, I'm not interested in that. Like you have to be like a very malicious person, and I wasn't at that point, and I don't think I ever would have been in my life. And it caught me so off guard because I'm not really used to that. Like I'm not used to someone coming to me and and presenting that kind of an offer in such a low pressure way, in such a human like vulnerable way. That I would just be like, no. And so my automatic response was like, yeah, sure, we can do that, right? And I was resistant still, but her warmth and her ability to go out of her way to ask me for that made me change and made me come around. And ultimately, I'm happy that I did. She ended up inviting me to her wedding, and I didn't go to her wedding, but I sent her well wishes. And And she really, she really made an effort and I respected her for that. So here's what I wanted to share about this. When you're in a situation when you're either dealing with somebody that, you know, is hard to get on board with, there is always a way to get them to come around, right? And if there isn't, it doesn't have to do with you. It's not about you. But sometimes we need to get relationships in the workplace working So that we can get our job done. And in this case, she needed me to get her job done. And so what she did was she didn't go complain to her manager and say, Natalie's not helping me. Natalie's kind of a bitch. Instead, she took matters into her own hands and she decided, I'm going to invite Natalie to coffee as many times as I need to. And I'm going to make an ask that's difficult, that's going to be difficult for her to deny. Without seeming unreasonable. And she was successful. And because of that, I took her example and I have since done that with people in my career. And it has worked very well. And I'm not saying it's going to work 100% of the time. You might need to try some other things. I've tried a bazillion things and I have found things that work. One meant like going to a novelty store and buying a funny joke gift for this person. That ended up getting them to, you know, loosen up a bit and chill and talk to me and help me get what I needed. There's always a really creative way to get there. So if you're struggling with somebody right now, or you might be the person who's like, oh, I don't want to talk to this person, and it's no— there's no shame in that. I mean, like, I feel like we're all going to be at that point at some time where we don't want to help somebody. That's okay. It's humanness and vulnerability and humility that usually gets through. Like, people do not know what to do with humility, right? She's like— and that was what she did. She came to me, she's like, I don't know you, I know you don't know me, and I get the feeling that you don't like me very much, and I was wondering if maybe we could do something about that. And, you know, bringing it out onto the table, making it known, making an ask, being authentic about it. Like, she was being truly authentic. And she wasn't asking for too much. She was just taking it into her own hands to do something about a situation that was keeping her stuck in her current job. So I hope that helps. Tune into the 13 stories. They'll be on this page, or you can get an opt-in to get all 13 stories. I am teaching people. I'm on a mission to teach people that human dynamics in the workplace don't don't have to be so difficult all the time, that there is always going to be a way to get through to somebody using human psychology, using an unexpected trick, using something that can break their pattern completely. And it feels incredibly satisfying to be able to do that. Once you've done that a few times, you can build the identity of the person who can get through to difficult people, who can get through to people who might be not wanting to get on board, who can get your idea through, who can get heard, because of the amount of ways that I've been willing to try and see the response. And I've studied human psychology and I've had several coaches who have helped me with these particular situations. And so I'm very blessed to be able to now pass that on. So if you're interested in this, grab all the 13 stories. I'm telling a different one in every one, and it'll help you with a tidbit of how to manage these situations at work. Whatever they might be for you, because it's in these moments, in the moments where you respond, in the moments where you make a decision, that's where your promotion happens. That's where your raise happens. That's where the opportunity gets given to you instead of somebody else, is in those moments of your response and of your decisions, not in what happens, because those things happen to everyone. We all are going to deal with a difficult person. We're all going to have a situation where we haven't acted perfectly, or we didn't understand something perfectly, or we didn't know something. We're all going to have situations like that. So it's not about the situation itself. It's about how we react, respond, what we do, and how we think and feel before we speak. So I will see you in the next one.
If you enjoyed that story, and you gleaned something from it, if you want to learn how to master your professional life while being both impactful yet Deeply human. Join the waitlist for Professionally Human. The link is in the show notes. I can't wait for you to see what I have in store.
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