Creating Confidence with Heather Monahan - Confidence Classic: The Art of CONNECTION (Why Serving First Changes Everything) with Jordan Montgomery

Episode Date: December 24, 2025

Most people chase opportunities, but the most successful people create them by how they show up for others. In this episode, I sit down with my dear friend and performance coach Jordan Montgomery to break down the real mechanics of connection, influence, and service. We talk about why the most connected people are the ones constantly promoting others, connecting people to opportunities, and giving without expectation. Jordan shares a weekly framework that has quietly opened doors to rooms most people never get invited into, and I share stories of how showing up with generosity, even when the payoff wasn’t immediate, came back tenfold years later. Get ready to stop chasing opportunity and start becoming the person opportunity looks for. In This Episode, You Will Learn Why CONNECTED people become connected by CONNECTING others first. How PROMOTING people builds real influence, not just visibility. Why SERVING WITHOUT EXPECTATION creates trust and long-term opportunity. Why the best opportunities often come YEARS after you show up. How to stop building a “BROCHURE” and start building a BRAND. The weekly QUESTIONS that quietly expand your influence and network. Why SPECIFICITY is the secret to meaningful connection. How proximity to the RIGHT PEOPLE can raise your standards and your results. Check Out Our Sponsors: Shopify - Sign up for a one-dollar-per-month trial period at shopify.com/monahan Quince - Step into the holiday season with layers made to feel good and last from Quince. Go to quince.com/confidence Timeline - Get 10% off your first Mitopure order at timeline.com/CONFIDENCE. Northwest Registered Agent - protect your privacy, build your brand and get your complete business identity in just 10 clicks and 10 minutes! Visit https://www.northwestregisteredagent.com/confidencefree Resources + Links Call my digital clone at 201-897-2553!  Visit heathermonahan.com Sign up for my mailing list: heathermonahan.com/mailing-list/  Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com  If you haven't yet, get my first book Confidence Creator Follow Heather on Instagram & LinkedIn Jordan on Instagram & LinkedIn

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I think if you ask yourself a question every Monday or once a week, it's like, okay, who can I promote this week? Who can I connect this week? And who could I serve this week? I think over time, you wake up in a world where you created so much impact, but you've also created a ton of opportunity

and you have all these relationships. I'm 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. I'm ready for my quota. Tell me, have you been enjoying these new bonus confidence classics episodes we've been dropping on you every week? We've literally hundreds of episodes for you to listen to.

So these bonuses are a great way to help you find the ones you may have already missed. I hope you love this one as much as I do. Hi, and welcome back. I'm so excited for you to meet my guest this week. Wait a minute you've met him before. This is Jordan Montgomery. He's the owner of Montgomery Company's highly regarded performance coach, keynote speaker, whose clients include businesses, executives, sales organizations, and entrepreneurs.

From a small town in Iowa to a dominant force in the performance coaching industry, Jordan travels the country, speaking and coaching executives at Fortune 500 companies, professional athletes, and salespeople. In addition to his work speaking and coaching, Jordan is an accomplished business leader who has managed top performing sales teams in the financial services industry. He resides in Tippin, Iowa, with his wife, Ashley, his son, McCoy. I thought it was Mac. Wait, if I've been calling your baby the wrong name all the time,

and his three daughters, Audrey, Claire, and Olivia. When he's not writing, coaching, or speaking, Jordan spends time with his family and enjoys the outdoors. He is a lover of sports and all things Iowa hot guys. Jordan, thanks for coming back on the show. Heather, thank you for having me. And you know what? I just appreciate your friendship.

You've just been such a dear friend. And so it's fun when you get a podcast with someone that you just genuinely want to catch up with and hang out with any. So fun that we get to hang out and you've been such a good friend to me and Ashley and we just appreciate you. Oh my gosh. Sadly, we don't get to record all of our conversations for the podcast. We would have much better ratings. All right, but listen, here's what I want to get into today.

You shock me. Okay, guys, listening, first of all, I met Jordan. Jordan and I met through David Nurse, who another guest on the show connected us. Oh, my gosh, a while ago now back when people didn't see people in real life. So we got to know each other and establish a friendship over the computer, never having met in real life. And then just a couple of months ago, we finally ripped the Band-Aid, met in real life. I didn't know if you were going to be four-foot tall or six-foot tall. I didn't know what to expect.

And I was so excited. If you guys haven't been going to in-person events, like now is the time to do it. It is pure magic getting to be with people after a couple of years of this isolation. But, you know, getting to hang out with you in real life. I thought I was going there doing you some big favor because I'm such a social media influencer or whatever. And I'm like, oh, that's so nice to me. This is literally what I, guys, this is so embarrassing that I tell you my true story like this. But I'm really thinking myself, oh, I'm so nice.

I love Jordan. He's such a great friend. Love Ashley. Love their family. Do anything for them. They want me to go to this event. Yes, I will go. Never having been to a Maxwell anything in my life didn't know what to expect.

walked in there and literally, guys, and I've already said this, I was blown away by John Maxwell's event, Maxwell leadership team, by him, by Jordan, by the crew we got to run with for the time we were out there, the incredible people, the men with the vulnerability, trying in the room, talking about how much they love their wives. I'm talking about God in business. I've never ever been a part of something like that. Literally changed me forever and just elevated the bar on my expectations for people and reminded me power and proximity is a real thing. It can change your life and the people you surround yourself with not only on your day to day, but also on who you choose to go hang with even for an event can be game changing.

So I just want to say, I'm so thankful that you got me there, you invite me there, and I'm the lucky one. So how do you get invited to these things? First off, shout out, yeah, Maxwell leadership, John Maxwell, and shout out Chad Johnson. It was kind of his idea. I mean, so I was having a conversation with Chad, who's the right hand to John. It's been chief of staff with John for a long time. Dear friend of both of ours now, Chad Johnson, and we were talking about John pouring into

the next generation of leaders. And so the behind the scenes on that one is Chad said, well, what if we invited some leaders to a Maxwell leadership event to pour into the next generation? But here's what's so cool about John Maxwell. Instead of that being a way to generate more revenue and like sell tickets and get more people to buy and increase revenue. John extended an invite via Chad. They found a sponsor to pay for us to be there. And we're going to run it back again and do the same thing all over again in August. And you're going to be there and I'm going to be there. And it's going to be there.

And it's going to be great. So I think there's an abundance. There's an attitude of an abundance with John and their team. How do I get to be there? I don't know. I feel lucky to you just to know Chad Johnson. You're so good. We're going to talk today about connections and building relationships. You're so good at adding value to people. I don't know that I deserve to be in that room. I don't know that I deserve to know John or Chad. I just try to be intentional about adding value where I can. And sometimes I can add value, sometimes I can't. But where I can add value, I want to be intentional.

And so I think that's just an echo. Like those opportunities are an echo of the value that you provide. And sometimes the echo is big and sometimes it's small. But I think if you live in a way that you're serving, you're adding value. I think those things just kind of naturally happen to people who are focused on adding value to others. And you do that so well. Like you're doing that, I think, at the highest level. And so you're quick to give away credit.

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Go to Shopify.com slash Monaghan slash confidence. That's Shopify.com slash Monaghan slash confidence. This new year was Shopify by your side. I ask you to try to find your passion. Lead with values first. That is the key. Too many people,

and this happens with the podcast guys, all the time. I get so many requests to be on the show, and I'll get an email like this, teed up. Hey, Heather, really want to be on your show. I'm unbelievable at blah, blah, blah, blah. blah, blah, when do you have time to interview me? A hard pass right to the trash.

I don't care who that email came from. It's going right in the trash. However, I'll have someone show up on email to me say, hey, Heather, here's a picture of the review I just left your show. I listened to Jordan Montgomery's episode, and here's the three takeaways I took that I really loved it. So telling me, they're actually consuming my content. They actually care.

They told me what they liked about something that we did. They gave me a review, which was thoughtful and kind and took time. I'm going to go read that email. then they talked to me about how they could add value to my listeners, how they can add value to me. That's adding value to me. Heather, I have never heard you do a show on blah, blah, blah.

Here's how I think your listeners can benefit from learning this. And here's some of the giveaways that I'll provide for your listeners, doing more for my listeners. When you bring value to others, it comes back to you. So, so crazy, two quick examples. And this is like, I hijack my own show. I bring people on my show and then I interview myself. Oh, good.

Perfect. So two quick examples. Back in 2018, I had written Confidence Creator, didn't know what I was doing, pitching myself everywhere to sell books, BNY Mellon says, yeah, we'll buy a bunch of books. It wasn't a lot of money. They said, we need you to come in and do a talk for this women's group. Yeah, sure, I'll do it. I go, I show up, I killed it.

Like I made this thing big for them, and I wasn't making a lot of money. I didn't do it for the money. I did it because I knew I need to build something and I wanted the message of confidence creator out there. wouldn't you know? I didn't know it at the time. And this is why, guys, keep showing up and just believe in yourself, believe in doing good, and those doors will open. Cut to five years later, I met a dinner, a technology dinner in Miami last week with a bunch of CEOs and founders, I don't know. My really good friend of mine orchestrated this dinner. So it was cool. I'm meeting

people from all different industries. You know, I don't know anyone. And all of a sudden, the founder of Emerge Americas, which is one of the largest conference. in Miami. Tom Brady headlined it this year. It's huge. Walks over to me, extends her hand and says, I don't think you remember me, do you? And I said, I don't. I'm Heather Monahan. I'm introducing myself. She reintroduces herself, says, you spoke at BNY Mellon Women's Event five years ago, blew me away. I completely forgot you lived here. I'm wondering, could I get you to keynote next year? And I'm thinking, I wouldn't, that lady wouldn't know who I am. Otherwise, if I hadn't shown up at that small event that I really wasn't making any money for.

Now the only misstep is I should have been at the one with Tom Brady this year. But we're going to go ahead and we'll figure that up. All right, cut to another example that just happened yesterday. I was headlining an event from MLM last year in Orlando. They did the event with me. It went great. I left. They called me a week later and said, we have a virtual event.

We're supposed to be doing our keynote speaker just bailed on us, got sick, or something. Is there any way you can jump in? in. It's nowhere near the money that you get paid. But I love the people. They were so great to work. I'm like, you know, I'm team you. Let's do it. I jump in. I take whatever they give me. Wouldn't you know that woman ends up leaving that company goes to another MLM last night on DMs. She's messaging me, hey, just took over a huge new company. We'd love to have you come in and headline our keynote this year. My point being, if you work with good people, you show up and go the extra mile for them. You never know when they're going to open that next door. or how they're going to pay it forward. But don't you believe it always comes back tenfold? Always comes back tenfold. But I think if you expect it to come back tenfold, it changes everything.

You know when somebody is serving to serve and then when they're serving to get something in a return. And if you're serving to get something in return, it's not serving. You just completely take away from the value that you're adding. So I don't know, I'm guilty of that, right? I think we all are on some level where maybe there's been a moment or a conversation where you say,

hey, I love to help with this. But your motives might not be pure. In other words, you want to help with something because you're hopeful that that person then helps you. You can't be doing good. Sometimes when I asked Gary B's partner if I could help him develop a strategy

for launching his wine brand, I have hoped in the end he would help me get to Gary. I didn't know if he would. It wasn't a guarantee. He ended up doing it for me, but I was hopeful, but I wasn't expecting. And I think that's a way to be hopeful. I think it's totally okay to be hopeful.

It just isn't okay to be expected. Like, I did this for you, therefore I'm going to get some. No, no, no. And then we're a little bit disappointed. Gosh, that person didn't do anything back for me. It's like, well, then that wasn't really service. So okay to be hopeful. Just don't be expected.

But I also think here's one thing you're good at that I want listeners to hear. I think there's two things. I think number one is slowing down the conversation about service. So how many times do we say something like, hey, love to sort of love to help you? Like, it's like we just, those are like throw away comments that we use in everyday conversation. You're good at like slowing people down and saying like, hey, I really want to help you. Like, let me give you my heart behind the matter or let me give you some additional thoughts. Like you've done that with me time and time and time again where you're like, hey, I really want to help you.

And then here's the second part of it. Get specific. And I want to help you in these areas. Or I think I can add value to you in these areas. So specificity and then slow. blowing it down, help somebody to feel like, wow, Heather is being genuine and like service. Like she means it. This isn't a throwaway comment.

Like she's giving me her heart behind the matter and she's getting specific with me and the ways in which she wants to serve her help. Those two things are a complete game changer because I used to say all the time to people like who are on our podcast. I'd say, hey, Heather, if there's anything I need to help you or support you, I'm all in, I'm in your corner. Let me know how I can help. And what do people say to that? They always say, okay, sounds good. you know, I'll think about that and we'll talk down the road. We changed that and now we say, look, our company, our team has made a decision to serve

the 50 guests that will interview on our podcast this year. We're really committed to that. I think there's some specific ways that I could add value to you and to serve you. So if something hits you right now where you're like, I got a book or a project or I need this specific connection, then let's talk about that. But I also want to give you permission just to sit on that, think about it and get back to me in the coming days on one way that the Montgomery companies could come alongside you, serve you, add value, and help you.

We mean it. We're excited about that. And I really want to serve you this year. Now somebody feels like, okay, there's a strategy. They share their heart behind the matter. They're intentional. They're getting specific. So if you're listening to this, you're thinking, well, Heather makes it seem so easy.

Like, you know, she adds value and doors just open wide. Well, it's because of specificity and it's because you slow down to share your heart behind matter. When we started doing those two things, everything changed in terms of the opportunities that got created and the impact that comes with it along the way. And you're good at that. You could speak to that because that's something you do so well when you serve and when you reach out to help people. Do you see it that way? Or are you just like, no, that's just who I am and I've never really slowed down to think about how I do that? Yeah, no, I don't really slow down and think about how I do a lot of stuff, right? I just show up. But I've been connecting those dots recently

thinking about the same things that made me successful in corporate are the same things that make me successful as an entrepreneur. And really, it's about creating community and allies and contacts of people that you're elevating and helping and connecting. And then they're out there spinning up that same stuff for you. Like, again, back to really just being around good, like-minded people who, you know, are willing to help others, want to do good and being aligned with people like that. When you're around people like that, I don't know. It's just, I find it so easy to help somebody else because I trust, right? Like, I trust that if I'm going to connect someone with you, they're going to love you. You're always do the right thing. You're always working,

you know, towards good. And if I'm around people like that, people I trust, it's so easy to open doors and connect other people. But, you know, the first time you and I met when I did your show, I was a guest on your podcast, you at the end, you said to me, I'll never forget, we were off air you guys the best conversations happen off air i need to do a show just of the off air stuff is so good but you said to me when we got off air you're like listen brine brown is out there killing it i'm gonna do everything that i can to get you to that level because you deserve to be at that level and i thought oh no one had ever said i say that to myself all the time but nobody else had said that to me right and i'm like oh my i love that you gave me like this genuine compliment i could tell you're passionate

about helping others i love anyone and and you mentioned there are aren't enough women out on big stages. And I'd like to play a role in advocating for you. And you've done it so, the connections you've made for me. I mean, it have been incredible. So again, back to serving first, you know, and being honest, noticing, always complimenting people with an honest compliment. That's an easy way to make a connection very quickly. That helped me huge on the Steve Harvey show when I was like the one guy that didn't belong there.

Giving an honest compliment to another person made a fast connection, allowed people to start smiling. so always lead with an honest compliment and do your homework ahead of time on people so you can save the ways that you could benefit them that you could help them and that maybe that you may already have connections in common. So good. And here's the thing.

This, the art of what we're talking about here doesn't get taught. And so I would love to get a little bit practical here because here's what I think happens. We teach sales. We teach communication. Teaching like the art of promotion or teaching connection.

People just say, oh, go connect. or go promote or go serve, but it's okay, well, then, well, how do I do that? Like, what are the steps? What do I do? What do I not do? And so I think teaching that, like, again, there's things that you do so naturally. Here's three things that you do really well. I was thinking about this before we talk, because I know we're going to have this conversation

today. There's three things that Heather Monaghan does, and you probably don't know that you do this, but any, like, world-class connector communicator, anybody who has a lot of relationships, is probably doing all three of these things really well. Number one is you promote people. So this is obvious, like even on your social media brand. A lot of people post a lot on social media, right? They're like, oh, I'm building my brand,

and they're sharing all their own content, and they're posting stuff, and they're consistent and they're intentional. But they never comment on anybody else's posts, and they never share anybody else's content. You are constantly sharing other people's content. You're commenting, you're encouraging, you're checking in, like you're advocating for people.

So you're building a brand, whereas a lot of other people are building a brochure. If you're only posting your own stuff and you're expecting people to come to you and build relationships, it's like, you're not building a brand, you're building a brochure. The only stuff you ever post is about you and you never take the time to comment or share.

Like, you're constantly commenting on our stuff and sharing and you're an advocate and you're an encourager. So, like, one is I think you promote people really well. Two is I think you connect like crazy. Like you're always trying to find good people who deserve to know each other. We've said it this way that connecting people are connected people.

Like, if you want to get more connected, start connecting. And you're great at that. And I think you connect people to people. I also think you connect people to opportunities. So you just randomly say, like, hey, here's a thing that's going on. You should be a part of this.

And I'd like to think we do that too, where it's like, hey, there's this event that's coming up, but you should be a part of this, or you should drop in on this. Or, hey, I want to make you aware. David Nurse does that. You do that. Brad Lomnik does that.

Like, the best connectors that I know are always trying to connect people to people and people to opportunities. We were just talking about a couple opportunities offline. One of them I think we're going to talk about here in a bit more specific way, with John Gordon and Pat Lanchone, which is part of the reason we're having this conversation today. And then the third thing you do, we just talked about, is serving,

you know, this idea that, like, living is giving, and you're trying to find ways to serve and add value. You're hopeful, but you're not expecting that it will create impact and opportunity. But I think if you do those three things, I think if you ask yourself a question every Monday or once a week, it's like, okay, who could I promote this week? who can I connect this week and who could I serve this week? I think over time you wake up in a world where you've created so much impact,

but you've also created a ton of opportunity and you have all these relationships. That's been your story and your journey over the course of your life. And I think you naturally do that. You promote you connect and you serve. But nobody like slows that down to talk about it, to teach it, to train on it. Like I'd love to hear what you have to say about that because like you're teaching, your training, you're living this out. Do you think that gets overlooked, like the art of connection and the art of promotion?

Don't you feel like that needs to be taught more often? Yeah, absolutely. Or not. Maybe that's how we keep, that's our unique value proposition. I want to own that. No, we're sitting here breaking it down for you because I want everyone to own it. Here's a thing, Jordan just gave you very specific steps to take. People lose, they have this intention that they want to connect and it sounds good,

but then you lose it in the details, right? It's so easy to say, oh, I guess I'm not good at that and chalked it up. No, take the specific step. Like he said, stop on a Monday. Put it in your calendar, a reminder. Who are you connecting this? Be intentional. And you just are thoughtful about it before you jump on the Zoom call with that next,

before you go to that next event. And there's, you know, 50 people that you're meeting for the first time there. Go on your Instagram and see who you know in common. Start trying to understand who you already having in connection together and then how you could add value in some other way. When you start leading with that approach, that intentionality, start asking how you can help others, start doing your homework. Oh, my gosh, you will see that magic will just begin to happen. But Jordan, you brought up, and it's so interesting, yet again, another incredible opportunity that you brought me into, not wanting anything to support our friend John Gordon and something really special and unique that he's doing.

Can you break it down for everybody? Yeah, so John's got a series that he is kicking off. It's called a day with, and then he's going to invite other thought leaders for a full day leadership, really experience. It's not an event. It's a gathering. It's an experience. And so you apply to get in. There's 75 leaders that will show up to a full day experience.

And he's 75 leaders. So like if you're a CEO, if you run a company, or maybe you're a community leader, but you're somebody who really wants to take your influence to the next level and you've got a lot on your plate, a lot of responsibility. You'd be a great fit for this event. it's not meant to be exclusive, but we do want to bring people together who are committed. And so the first event is with Pat Lanchone. Heather, I think you'll be a part of a future event. It's been tossed around that maybe Ed Mylett would be a part of the future event or Erwin McManus, but it's really John's event.

It's a day with. The first event's going to be November 2nd this year in Dallas, Texas, Kempton Hotel. There'll be 75 leaders getting together for a full-day leadership event. And then there's a VIP dinner the night before. Heather, you and I were joking that, like, you could remember. remove John and Pat from the event, and it would still be a huge win just based on the caliber of people that are going to be in the room. So we've got some pro athletes come in, some coaches, some CEOs.

Again, you don't have to be a CEO to attend. You could be a young professional that just wants to expand or influence, but we do really want people in the room who are committed. So people can go to a day with John and Pat.com to get more information. We'll add, I think, that link in the show notes, but it's a day with John and Pat.com to get more information. You can apply to get in. We'd love to have November 2nd in Dallas.

And again, this conversation is happening because you said I have an idea. Let's host to show on my podcast to help John and Pat, you know, drive some folks to their event, increase awareness. So another example of serving, like that's literally,

you and I are friends that we talk often, but that's literally the reason that you and I are having this conversation today is because you had an idea to add value to John and Pat, thought we could do something kind for them. So it all comes back to promoting, serving, connecting.

Another example of that. And, you know, this time, hopefully, to the benefit of John and Pat in that event. Meet a different guest each week. Build your complete business identity in just 10 clicks and 10 minutes when you want more start your business with Northwest Registered Agent.

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at www.w. Northwest Registeredagent.com slash paid confidence. I ask you to try to find your passion. My goal is to add value to our listeners. Shout out my peeps listening right now. But here's the thing. I really thought when you brought me into a behind-the-scenes about this upcoming event,

event with John and his team and a bunch of other people that want to support the event because this is an incredible opportunity. I just thought to myself, if there's anyone in my community that could benefit from this that would love being in that room, and it was coming off the heels of us just having been at the Maxwell leadership event where you could have pulled John Maxwell out of that event. It still would have been in the most incredible event that I've been to, right? So it isn't just about the headlining personality. It's about being around really high caliber great people who inspire you to go for more, who show you what's possible for you, who speak life into you and possibility and encouragement. And to me, that's everything, right?

It is everything. And we're going to sign off this way. I'm going to say this about you with your peeps listening. So I live in Iowa, fairly small town, about 100,000 people. We have four children. My wife and I run this business together. In the world of leadership, I am further behind. right. I'm not where you're at. Like I'm 35. I live in the middle of nowhere. And for some reason, you decided to take an interest in our business, our company. You decided to take an interest in my wife and I. And you've been like over the top generous and so encouraging. We've been through some family stuff and you've prayed for my wife and I and you've sent stuff to our house and you've like texted a scripture and you followed up with us and you checked in. Like when so few

people checked in. Like, you are still checking in. I just think that is so rare in today's world, especially when people make it to a certain level, right? Like, they have a lot going on, and they're busy, and you have all these opportunities around you. And yet, you're checking in on the Montgomery. He's glued in the middle of nowhere in Iowa. Like, you made a post about us, like our friendship on social media. And I'm like, that doesn't even make sense. Like, how, like, there's no, I didn't ask you to do that. There's no, like, business angle there. like you were just trying to be kind. But here's the reason I say all that.

And I'll leave our, I'll leave all listeners with this. Like the true test of somebody's character is how they treat people who can't do anything for them. And you've just treated Ashley and I so well and been so kind. And we're just thankful for that.

So somebody's listening and I're thinking, man, I'd love to be that way for other people. Like, I would love to have somebody say that about me. And the good news is like you can be a heather too. You can go out of your way to serve, to connect, to promote. There doesn't always need to be a string attached. And when there's not,

there's this really beautiful thing that you're going to do for somebody who looks at you and goes, like, you changed my life. You opened doors. Like, I don't understand why you were radically generous with me, but you were, and I'll never forget it, but I'll do everything that I can to pay it forward. And so Ashley and I both just want to say thanks to you for the ways in which you've blessed us and been kind to us. And we're just like super, super grateful for that.

So just know that. I wanted to share that with your audience listening. And now you guys know why I love the Montgomery's. And you know what's interesting is I'm meeting you in my late 4th, So I hope that inspires all of you. Be open-minded that there are other great people that you're going to love and know and support you in this world.

Be open to people and go to new places. Talk to people in Iowa. Who would know that I would be such team Montgomery? But I am ride or die for life. So you got me. Guys, until next week, keep creating your confidence. You know I will be. I decided to change that dynamic.

I couldn't be more excited. for what you're going to 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. I'm on this journey with me.