What do you do when your boss keeps cancelling — and the clock is ticking on something you actually need them for?
Most people wait. They reschedule, follow up politely, and hope the meeting eventually happens. One of Natalie’s clients waited too long — and it cost her a bonus she had already earned.
In this episode, Natalie shares the creative workaround she used with a boss who was perpetually unavailable — and why the real skill isn’t persistence, it’s understanding how a specific person makes decisions and what it takes to get a quick yes from them.
What You’ll Learn in This Episode:
- The hallway move that got Natalie two answers from an unreachable boss in under two minutes
- Why “I can’t do anything because they won’t meet with me” is almost never actually true
- How to frame an urgent request so it feels effortless — not burdensome — to the person you need
- Why different bosses need completely different approaches, and how to read which is which
- The hidden career cost of staying quiet when things stall — and what you’re actually leaving on the table
This one is practical, fast, and packed with the kind of human psychology insights that separate people who get stuck from people who keep moving.
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DOWNLOAD TRANSCRIPT
Hello, welcome to 13 Outrageous Work Stories That You Won’t Believe Happened. Everyone, 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 a hold of, they keep canceling meetings, 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 this 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. not ready. Like, 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 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 I knew he wasn’t going to be available. I was like, oh yeah, that’s just not going to happen. 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 two 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 was just that energy of like, I just need these two 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 see what they say about that. And then for this, 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. So that gave me two things that I could do to move that forward, even though we were 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’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, they process, how they process things and frame it in a way that’s best for them. So I framed it as in this is just going to take two minutes. I just have two questions and you’ll be out of here before you know it. And he was he was good with that. Now, I did a lot of experimenting because 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 want to 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 three or four different things, there’s going to 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 going to respond to the same thing. Somebody might be really offended that I walked up to them in the hallway and asked them for two quick questions. And someone might be like, oh yeah, let’s 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. uh So yeah, 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 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 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 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 the person. If they are your boss or your colleague or your coworker, there is always going to 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 pay scale for you. That is what opens up the up leveling 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 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, if you’ll 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. uh 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.
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