#106: What Powerful Conviction Can Do For You with Heather!
4 Nov 2025 · 25 min
Heather Monahan shares how conviction gets results: she retrieved a wallet from a dumpster and landed a major advertiser deal by securing a Rao's reservation. She teaches phrases like "I'm confused" and "help me understand" to handle pushback at work, and says public commitment to goals makes you follow through.
Chapters
Come on this journey with me each week when you join me, we are going to chase down our goals, overcome adversity, and set you up for a better tomorrow. Fasten your seatbelts. I'm ready for my close up. Hi, and welcome back. I'm so excited you're back here with me this week. I hope you're loving the new format. Please hit me up in the DMs. Go to my website, heathermonahan.com Let me know what you think. This show is for you. I want to make sure that you're getting what you need, what you want from it. And I heard some feedback that people like the new format. So I'm hoping that it works for everyone. Okay. Crazy, crazy situation. You know, I. I don't know if I told you this. On Easter Sunday, I accidentally dropped my wallet in the trash chute in my building. I was doing, you know, 9 million things at the same time. I couldn't carry everything that I had in my hands, so I dropped my wallet in the Whole Foods bag. I just gotten home from the grocery store. And then I forgot that I did that, right? And so when I took all the big things out of the bag, there was still my little wallet at the bottom. And anyhow, I inadvertently went to throw all the bags out and didn't notice it was still in there. Threw it down the trash chute, okay? I didn't notice it till the next morning. So it was Easter Sunday in the morning. I was getting ready to go to the gym or go to spin, actually out on the roof that I always go to. And all of a sudden I looked for my wallet and it was gone. And I knew right then I thought, oh, my gosh, you gotta be kidding me. I totally blew it. I can't believe I did this. It's actually the second time I've done it. Last time was 10 years ago. So a decent pace, right? Once every decade, I do something completely ridiculous. So, all right, so here's what I do. I got super. Because it was the second time that I had done this. I knew I could get it out of there, right? I didn't know how, but I knew I was getting it out of there because my vaccine card was in there, which made it even more. I had to get it because I was coming up on getting my second vaccine. And I'm not about to lose that card no fricking way and start over from scratch again with the vaccines. So I went flying downstairs. I was talking to the guy at the front desk. I'm like, listen, you need to open up that trash room for me. I am jumping in that dumpster and finding my wallet. I don't care what anyone thinks about this. This is happening right now. So he was so nice, and he helped me to open the room up. But then we couldn't figure out how to open the actual dumpster. It was locked somehow. And he and I were kicking it. We were getting. You know, we're going crazy trying to get in anyways, make a long story longer. So he says, heather, I don't think we can do anything. We'll have to wait till tomorrow when the team's back, you know, all the maintenance people and everything, you know, on Monday. And I said, no, absolutely not. Because what will happen is so much more trash is going to go in. It's going to be too hard to find. We need to find someone now. Who can we call? And so he ends up calling one of the maintenance guys. He's at home with his kids. Easter Sunday, so sad. And we have. We're on FaceTime with him showing him how we can't get in. And finally the guy just said, you know what? I'm just gonna head over there. I'll be there in 10 minutes. So flipping nice. So this guy comes over. I'm waiting for him. Well, I came back up to my apartment to get money. Cause I had to thank him somehow. So kind of him to do this on Easter Sunday. He gets the dumpster open, and he looks at me and he says, listen, there's a lot in there. I just don't. I don't want you to get your hopes up. And I said, no, listen to me. We're finding it. Don't worry. This is happening. I just was so crystal clear on it because I knew it was in there, right? And I'm not going to leave.
I don't.
I will stay there all day till I pull every piece of trash out. I'm getting that wallet. So he was. He was kind of saw how serious I was about this, and I said. I said, you don't have to do it. I'll jump in there myself and do it. And he said, oh, my gosh, no way. He was so kind. So he ends up pulling out some trash. And, you know, he had an idea on how we could. It's packed so tight in there. It's compressed. And so he had an idea, and his idea was great. And he ends up pulling a few things out so that a lot of things would, you know, come out and wouldn't you know, I mean, within 10 minutes, he says, there it is. And he saw the Whole Foods bag. He said, I know. That's it right there. He picked it up, and it was my wallet. It was so crazy. I was so excited. But the reason why I wanted to share that story with you is when we get determined on something. Listen, the first guy tried to tell me that we couldn't do it because it was a Sunday, and then it was Easter Sunday. And then the next guy, you know, wanted to set my expectations. Hey, probably not going to find it. Every time someone said to me, no. I said, absolutely not. It's out of the question. It's 100% happening. I don't know how, but we'll figure it out. I'm not leaving here until I have it right. And when you come at things with that level of conviction, it is really hard for other people to not want to help you and help you solve that problem. Okay, so. So every week I'm on clubhouse Wednesday at 8pm EST for one hour, answering questions and talking about how to go to the next level, how to launch a personal brand, how to sell big deals, whatever the topics are. And last week, I was in Clubhouse, and someone raised their hand and asked a question around how. And I'm gonna botch it a little bit, so bear with me. But something like, hey, if you're in sales and you're having a hard time with the inconsistency, right? Because in sales, a lot of times you'll have a huge month, and then the next month, you have a terrible month, and then the next month, it's something amazing happens, and then the next month, you know, you can't close any big deals. They're really. It's like an EKG machine. And this woman was in sales, and she was saying, how do you get through those low times and keep your head up and stay motivated? She was having a really hard time. She was going through, you know, a lull in her business, business. And she said, so how do you do that? And I said, and this story reminded me of the Easter story. I said, oh, my gosh, I have to tell you a story. Remember, stories sell. Facts tell. So anytime you can leverage a story to allow people to understand something, a point you're trying to make, it's much more powerful and impactful. So I shared this story that I had forgotten about. Actually. This is probably, gosh, a decade ago, right? It's a really long time ago. I was either the VP of sales or the chief revenue officer of this media company I was running, I forget what my title was at the time, but I was in charge of revenue and we had lost a ton of business. It was just a really bad window for the radio business. The industry was down, everyone was cutting back. And I have, you know, I obviously I had monthly goals, quarterly goals and annual goals. And I kind of looked around the whole company and thought, okay, hang on, I need to close this gap and do it faster and I'm not going to get my bonus, right? So I looked at all the opportunities, I looked at all the markets and I thought, yes, I could take the approach that, you know, each market needs to increase their business by 10% or. And it's finally just said, forget it. No, I'm just gonna go to the largest advertiser that we have and I'm gonna go cut a deal to, you know, make up for my, my shortfall. So I jumped on a plane and I went to our largest advertiser. It was an insurance company, very well known insurance company, very famous insurance company, spends billions of dol. And I went into the ultimate decision maker who I had a relationship with. And I said, listen, we'd worked together for gosh, you know, six, seven years. I said, here's the thing. I am coming to you in need of help. I need you to increase your spend with me for the remainder of this year. Now, I know that this is a big ask and I know you don't have to do it. He's going to have to shift money from somebody else to give it to me, right? I mean, granted, we're going to do a great job for him and deliver, but he wasn't inclined to do this just because I need to hit a number. But I just got super clear on it and I said, so here's the thing, this is super important to me. You know, I explained to him, it'll be a huge help to me. I'm super grateful for you and for our business relationship. However, I want to make sure that you get something amazing out of this. What is the one thing that I could do for you in the world that would make this worthwhile for you?
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It's going to be a pain. He's going to have to go cancel somebody out. You know, it's just, it's just a headache that he didn't have to deal with. So he sits there for a minute and he said the one thing that you could do that would make this worthwhile for me, he said, is you could get me a reservation at Rao's. Now I had no idea what Rao's was at this point in time, but back when this was happening, it was a very hot restaurant in New York City, and it was impossible to get into. People actually owned or bought tables, right? You have your own table. I had no idea. So he. This man just says to me, all you need to do is get me a dinner reservation. Basically, that's what I hear. So I say, done, 100%. Consider it done. He said, heather, I need to explain something to you. This is not a layup. He said, it's the hardest restaurant in the country to get into. And I thought, oh, please, I'll find a way. I'm not even concerned, like, if this is what's standing in between me achieving my goal and budget for the year. Right. And my bonus financially, just, you know, personally, I like to always achieve my goals. I thought, no problem. I'll get in there. And he starts laughing. He was laughing at me. Basically, he was giving me a challenge that he thought I had zero chance of achieving. Guess he didn't know me that well. All right. So I hopped back on a plane, and literally on my way to the airport, I called my boss, who back then was the president of the company and a good friend of mine. I said, listen, I am going to change our year. I'm going to bring us to budget. However, we need to find out how to get a reservation at Rao's. And he had an American Express black card. And so I said, call black concierge right now and ask them if they can do it for us. He calls me back, no. I say, okay, call the bankers that invest in our company. They're all ballers. They're in New York City. They've got to know someone. So he calls. No. So I say, okay, who do I know in New York City? So I start calling everyone and anyone I know in New York City. No, no, and no. So I'm brainstorming with myself. Okay, you know, what am I missing? How could I go? I'm going to call the restaurant. I call a restaurant. No, no, and no. So I start thinking to myself, okay, this is much more challenging than I anticipated. I hope I didn't get myself into a tough spot here, but I'm not. I'm getting it. I don't care if this takes me a year. I'm getting this res. And the conviction that I moved forward on this initiative and it wasn't easy by any stretch of the imagination. It was ridiculous. It was overwhelming. It consumed my life. But on every phone call and every meeting I went on, it was the number one thing I talked about to everyone. I wanted to make sure everybody everywhere knew that this was my number one singular goal that I was working on and that I would achieve it, and I would appreciate their help. And wouldn't you know, one night, my girlfriend here in Miami called me and said, hey, come over to Casa Tua and meet me for drinks tonight. Tonight I go over to Casa too, which is a great restaurant here in Miami. And we're hanging out, and we were up at the bar. This is pre pandemic, clearly. And we're talking and just chatting with a bunch of people. And there was this huge group of people to our right. And I hear an accent. I hear a New York accent. And I said, guys, hang on a second. I walk over to this huge group of guys. I don't know them from Adam, and I said, hey, Hi. My name's Heather. It sounds like you guys are from New York. And they say, yeah, you know, we are from New York. I said, listen, this is so bizarre, what I'm about to ask you, but is there any chance that any one of you have any in to get me a res at Rao's in New York? And this one guy turns around and says, yeah, my brother owns a table. I said, are you freaking kidding me? He said, no. I said, can you call him right now? He said, okay. He calls his brother right there. I don't know this man. And puts me on the phone with the brother. The brother was so nice. I said, I will do anything.
I don't.
I'll pay you. I mean. Cause this was worth a lot of money to me to hit my bonus. I said, whatever you want. He said, no. He said, I'm happy to do it. He said, we have the table every day. He said, you know, we go all the time. Happy to do it. Sure. So he gave me the date. I had his number. I called my client the next day. I said, just so you know, you're going to Rao's. And we all ended up going to Rao's. So the moral of the story is achieving goals can be challenging, and there can be plenty of roadblocks and, you know, issues that come in your way, and plenty of people that tell you things can't be done. But when you get the level of conviction inside of you that you are relentless, the way that I knew I was not leaving that trash room until I had my wallet, I was not going to take a no on the rails. I was going to find a way. The way will appear, right?
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Was I left that woman. Actually, no, I know I left her with that feeling because she this again back to Clubhouse. She had asked me that question on Clubhouse and she came back to me on a DM on LinkedIn after and said I just want to say thank you so much. You reminded me that I have to be that committed. Right? You can't just be interested in doing well in sales. You have to be committed all in. You have to post your numbers for other people to see. You have to write down what you're going to achieve. You have to come up with what your why is. Why are you going after this? Right? And you have to hold yourself accountable. And in a funny way, it can be really exciting. That whole day, that Easter Sunday day, I was so excited that I got it done right. I didn't give up and I didn't quit and I want that for you. I don't want you to give up. I don't want you to quit. When you get clear on what your goal is, let nothing get in your way and nothing will. All right? Hold tight. We'll be right back. Meet a different guest each week. Okay. So when something shows up in my life twice in one week, it. I don't know, I feel like, okay, this means something. So I'm going to share the story with you and try not to get into too much detail about it. But the message is it's powerful and it's interesting. So I saw two extremely similar situations. One was in my personal life. I had dinner this week with a bunch of girlfriends, and one of my dear friends was dealing with a major challenge at work where she was getting completely hosed on a payout. And a situation at work she was completely being taken advantage of. And then fast forward to I have a group coaching program that I run every Friday, and I was excited for my group this week because one of the young woman who's amazing, love her. She's just such a. Such a great young lady, and she's come so far in the last month, and I'm so proud of her. She was going in to advocate for herself and ask for a title change because she had come to understand that she should have been given it on day one. She didn't know that was the case. And now as she had learned more, she was realizing everybody else had that title, but she didn't get it, and she was the only woman. Okay, so two situations that were very similar where people were somewhat being taken advantage of or, you know, not realizing their value that they should be or be or being treated the way they should be at work. So with both of those, you know, here's the thing. And I gave the same very similar direction, actually. And then I role played, right? Because when you role play things, you just feel more confident to go in and do it with my good friend, you know, I said, listen, here's a thing. You are owed this money, right? And she said, yeah, I mean, I am. I said, then why wouldn't you go in and advocate for yourself? And her concern was that, you know, she still had to work side by side with these people, and she didn't want to make it a fight, right? Here's the thing. It doesn't have to be a fight. Standing up for yourself, right? Setting boundaries, you know, raising your hand and saying, oh, this has got to be an oversight. Something's not right here. And I actually dealt with this with the company that I'm on, the board of directors. I noticed that I hadn't received my stock yet, so I just sent a note, hey, I'm sure this is an oversight. But somehow I have not received my stock options yet. So can we please have someone facilitate this for me? You know, it didn't have to be a big fight. And so I was suggesting the same kind of a thing to my friend. I said, listen, go in there and say, I'm sure this is an oversight on your behalf, but as you know, it wouldn't be me to not raise my hand and advocate for myself the same way I advocate for you when I'm out doing deals for this company every day. Let's get this situation straightened out so that we can focus again on business and keep it moving. You want me to be fighting for you the same way that I fight for myself because that's why you hired me is I am such an advocate at making sure that we do the best deals that we can and let's rectify this one so that we can move ahead. I was on my group coaching call and I'm a big fan of saying I'm confused. That's one of the things I lead with all the time if I'm in a difficult situation. Because basically you're saying you're calling someone out in a nice way. I'm confused. You know, why haven't I been paid on this yet? Right. So, you know, can you explain this to me? Well, one of the women in my group coaching had another way to handle it and I really liked it, so I wanted to share it with you. Her way was help me understand and I really liked how she framed that up. You know, help me understand what the challenges or where their breakdown is or help me understand what the miscommunication is here. I understood it this way.
Right.
And so we role played a few different ways for this woman to go back in to get that title change. I will keep you updated. I'm sure she's going to get it, but I just can't wait. And you know, I talk about this a lot. In any moment, you're either creating confidence within yourself or chipping away at it. With both of these women, if they don't go back in and have that conversation, they are going to be chipping away at their confidence. It's not as much about the end result as it is about them raising their hand and having the conversation. And that will give them momentum. That will help them feel more confident and that will remind themselves that they are worth it. And even if the outcome isn't exactly what they had planned for or hoped for, they're going to be that much closer to ensuring that they are treated better moving forward and that they will achieve their goals and will find the people and opportunities that they deserve to be around. So so that was my question of the week. Because it was so similar in both of these instances and both women had trepidation about going back in, I thought it was important to share, so I hope that helps. If you like the show, please leave a Review Rating Share on Social Whenever you share it on Social, I always repost you. And until next week, I will be right here creating confidence, hoping you are doing the same. I decided to change that dynamic. I couldn't be more excited for what you're gonna hear. Start learning and growing. Inevitably something will happen. No one succeeds alone. You don't stop and look around once in a while. You could miss it. Come on this journey with me.
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