EP 288: When your boss keeps re-scheduling 1-to-1 meetings
18 Apr 2026 · 8 min
In this solo episode of the Outrageous Workplace Stories podcast, Natalie Fisher shares a personal story about dealing with a boss who repeatedly cancels or postpones one‑to‑one meetings, a situation that can jeopardize bonuses and career momentum. She explains how she analyzed her boss’s decision‑making style, identified that he responded to brief, high‑impact requests, and successfully intervened by catching him in the hallway and asking two concise questions. The anecdote illustrates the broader principle that every boss (or colleague) has a psychological profile that can be matched with a tailored communication tactic. Fisher outlines four distinct decision‑maker types and stresses the importance of framing requests in a way that aligns with each type’s priorities. She warns that failing to adapt can lead to missed bonuses, stalled projects, and long‑term career derailment, while proactive, creative approaches open up opportunities and higher pay. The episode concludes with a call to action to join her "Professionally Human" program for deeper training and to access the full set of 13 workplace stories.
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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. Hello. Welcome to 13 Outrageous Work Stories That You Won't Believe Happened. Everyone, I think, goes through this. All one of my clients, all my one-on-one clients that I've worked with have had some kind of situation where their boss is hard to get ahold of. They keep canceling meetings. They're not, they're not rescheduling. And sometimes that can really get in the way. And one of my clients actually had it where she lost out on her bonus because she wasn't able to speak to her boss. And her boss needed to answer questions that she needed the answers for so she could get moving and she could actually get the project done where her bonus was at risk. And this is where you have to learn how to do it so that you can get what you need, even when it seems impossible. And that's what most people will do. And my client actually did almost just give up on this. So here's the story. When I had a boss where this was the case, I had been kind of analyzing his behavior and I was like, okay, what is important to him? What does he need? What could make inevitable where he's gonna be able to give me these answers? What can make it super easy for him? And the story was that he kept rescheduling it. He was just like, yeah, we're gonna have to push this off. I'm not ready. Like, I'm not— I don't have time for this right now. We'll have to meet next week sometime. And so I was like, okay, great, I'll reschedule it. So I just tried the, the next step, which would be, okay, I'll reschedule it, no problem. And then next week he would be like, I'm sorry, I can't do it either. And it just came to the point where like I knew he wasn't gonna be Available. I was like, oh yeah, that's just not gonna happen, right? So what I did instead was I caught him in the hallway and I said, look, I just need a few minutes. I just have these 2 questions. We'll get to the point of it. It's important because we're running out of time for this. And so I'll just catch you and I'll just, and I'll just move on, right? And it was just that energy of like, I just need these 2 questions. I'm here for the, like, to the point. It's no, it's no big deal. And It kind of like— people are afraid to do this because they don't want to— they don't want to get in the way, they don't want to burden people, they don't want to get in like be a problem. And this worked with him, and he was able to give me— give me at least a direction. He was like, okay, for this you need to talk to this person, and then— and then see what they say about that. And then for this you need to, um, you need to—
he would just make the quick decision and be like, we need to get the numbers for that first, and then we'll decide on that, right? So that gave me 2 that I could do to move that forward, even though we weren't fully in decision-making mode and we didn't have a whole one-on-one meeting. And so for him, for that particular boss's style, that worked. Now, through my career, I've learned that there's lots of different types of bosses. Some that would not work with— they would just be like, yeah, I, I'm on my way for lunch, I can't do it, right? But he was able to do that. And so we need to understand how people make decisions, how they think, what, what they process, how they process things, and frame it in a way that's You know, best for them. So I framed it as in, this is just gonna take 2 minutes. I just have 2 questions and you'll be outta here before you know it. And he was, he was good with that. Now I did a lot of experimenting cuz I did that with some people and they were like, yeah, no, I don't have time for that. I'm on my way for lunch. We'll have to do it later. And so I had to use a different approach with those people. And so what I wanna bring to the table for you is there's always a way to get through to somebody, even if you failed the first time, even if your first way didn't work. Even if you tried 3 or 4 different things, there's gonna be a way to get through to those people. And it's all based in how they, their psychology works. And because we're humans and we're complicated creatures, everybody is different. And so they're not all gonna respond to the same thing. Some, somebody might be really offended that I walked up to them in the hallway and asked them for 2 quick questions. And someone might be like, oh yeah, let's just, just get this out of the way. That's great. And then I don't have to have the meeting and you are ready to go do your work. Right. And with this particular boss, He was good at that. He was good at making decisions quickly, but he needed to know why it was important, and he needed to know that it would be quick. So yeah, I in my program I cover all the different kinds of people, the four different types of decision makers, how you speak to them, how we do this because it's imperative that these moments don't derail you. Like I like when like my client, like I said, she was really having issues with getting her boss. And she didn't have the tools. And if she didn't have the tools and she actually missed out on her bonus, imagine what else she's missing out on. The other opportunities, the other things that she could be moving along because she didn't have the tools to be able to get in front of people in the way that they needed so that they could quickly say yes, or they could quickly move along, move the project along, or they could, they could link up in their brain why this was important to them and why they needed to pay attention to it now. So oftentimes we'll say, Oh yeah, it's the other person's responsibility. They need to figure it out. And if they don't, then I guess I'm stuck. I don't have any other choice. That is almost never true. There is always a way. And I've been pretty creative in my career to do that, which I believe is why I was able to move up the ranks so quickly. This is 13 workplace stories that you wouldn't believe happened. This one is probably pretty common. You probably can believe it. Like, oh yeah, my boss isn't showing up for meetings. That happens. And my boss keeps rescheduling meetings. The thing that people don't see is the problem with this is It can completely derail your career if you don't make it, if you don't make it a priority to figure out how to get through to them. And working with hundreds of clients, I can tell you there is always a way to get through to the person. If they are your boss or your colleague or your coworker, there is always gonna be a way to get through to people so that you can get what you need. You can move your stuff along, and that is what opens up the opportunities for you. That is what opens up the The pay scale for you. That is what opens up the, the upleveling for you. Because the people who stay quiet, the people who give up, the people who don't say anything, the people who sit down and say, yeah, I can't do anything because my boss just hasn't rescheduled the meeting, they are the people that will be last. And they will end up getting frustrated, they will leave, and they will just think that it is everyone else's fault. When really there's so much we can take control of over, and so much a possibility, and so much in it, so much growth available just in learning the human psychology. of the other people that you're working with. This is something that I have loved and taken pride in doing. And they would even say, you know, if you get a difficult person, send them to Natalie because Natalie will deal with them. She loves them. So if you want to get all the 13 stories, you can opt in. If you're already opted in, watch the rest of the ones on the page, and I will see you next time in the next video.
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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