Creating Confidence with Heather Monahan
Confidence Classic: Lead with Curiosity and Confidence with Master Interviewer Cal Fussman
Wed, 28 May 2025
What if the key to better leadership, connection, and confidence came down to how you ASK questions? In this episode, I sit down with legendary interviewer and storytelling icon Cal Fussman. He’s spent decades in conversations with the world’s most influential people, including Muhammad Ali and Jeff Bezos. We talk about the power of curiosity, why asking great questions builds certainty, and how to navigate your life and business through deep listening. Cal also shares the life-changing lessons he’s learned from sitting down with the best and how you can use them to lead with purpose and impact. Get ready to rethink how you show up, how you connect, and how you lead! In This Episode, You Will Learn 00:00 How to repackage your VALUE with confidence. 07:30 How to write emails that convert. 13:30 The mindset Cal used to connect with global icons. 22:45 What is the fastest way to monetize trust into revenue? 26:45 How to lead pricing conversations without fear or guilt. 35:30 Why your lowest-paying clients often demand the most. 42:30 Why giving fewer options creates more action and better sales. 50:00 The pitch strategy that gets decision-makers to say YES. Resources + Links Listen to Cal’s podcast Big Questions Sign up for a one-dollar-per-month trial period at shopify.com/monahan Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN. Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN. Get 10% off your first Mitopure order at timeline.com/CONFIDENCE. Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com. 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 Cal on Twitter & Instagram
Chapter 1: How can you repackage your value with confidence?
Is there a way of thinking to not leave money on the table?
First of all, there's market research that we can do, right? So we know with keynote speeches, they start at $5,000 and they go to $500,000. So just being familiar with how wide the gap is and what people are offering, you can pretty much feel confident going in that whatever your number that you think is big, there are people offering the same services for much, much more.
So know that you're not the highest price point. You know, I had the opportunity to speak with a lot of different people across the country over the past year. Some of them were getting $150,000 on the same stage I was on and I was getting 15,000. Here's the thing, Cal, you can always negotiate down, right? Say you go into a meeting and you're asking, here's my virtual speaker fee.
Let's take a look at what dates work for you. You know, so you put the fee out there and then you ask for the date and then they'll say to you, Cal, wow, that's a little bit more than what I had budgeted. And that's when you say, great, great. What did you budget? What had you budgeted? 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. I'm ready for my close-up.
hi and welcome back i'm so excited that you're here with me so this has been an interesting week for me i'm launching my first ever well when you hear this i'm already gonna have done it but for me i'm recording this a couple days earlier i'm usually a few days ahead of you but right now i'm Almost a week ahead of when you're hearing this.
So I am conducting my first ever live workshop with a Harvard professor tomorrow for a group of people who have bought tickets to attend. I've never done anything like this before. Right. And this all stemmed from the pandemic happening yesterday. Speaking engagements canceled, revenue dropping.
I launched this May mentoring program, which has evolved into me learning all about this online coaching seminar, masterclass, mastermind business that if you're like me, I had no idea was a business, much less it's multi billions of dollars. And actually more and more people are moving learning online, as I believe everyone is right now, right? So it's just how can we repackage our value prop
and bring it to market virtually. Sounds simple, however, it's not. So my mentoring program was kind of, that was easier. It's me coaching people one-on-one and then once a week as a group, which is essentially what I did in corporate America. So that's easy, but this is different. Number one, because I've partnered with another person, right?
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Chapter 2: What mindset helps connect with global icons?
Everyone just needs to be learning right now. And that means sometimes failing and sometimes making mistakes. And yeah, I'm sitting here right now saying, gosh, I put a ton of time into this. The ROI will not be there for me and not for John on this one. But we did have a call today that now that we've figured it out or are figuring it out, It can become more of a low touch product.
You know, we are more comfortable working together. It's part of the process, right? The journey. So we'll reevaluate after. And obviously our goal will be to extrapolate testimonials, social proof, because social proof drives new business. Ideas John had was maybe we ask on the call, guys, who here works for a company that
that they could connect us with that, you know, we could create or customize a specific class for you and for your team. So I think that's an interesting idea because businesses are looking for ways right now to support employees, invest employees and help them decipher how to communicate during this very challenging time. And I see some people doing it successfully and some are not right.
And every advantage we can give to ourselves, to our companies, to business right now is a game changer. It's that small sliver of a difference that can make a huge impact. And I noticed this when I was running that someone was 10 seconds ahead of me and I thought I can catch that person.
But if you don't speed up and do something different, that 10 seconds after 10 laps has grown immensely and you are so far behind. And that's what we're seeing happening right now in business and with innovation or lack of innovation. small changes are really impacting business and the ones that aren't changing are going to be left behind in the dust.
So this is why I'm jumping into this seminar and this online virtual world. I've got to change. I've got to evolve my business. Some of it's going to go great and some of it's going to cost too much time and effort and money and not going to be worth it. But I'm only going to learn if I do it. So I'm in that is since I got fired. That's my new thing. Step into fear.
Fear is a green light that means go in. And we're going to make it work. So we did offer a money back guarantee, which I think for everyone right now is really smart. We need people to trust us and feel safe with us. That is paramount. Those are the two factors everyone is interested in.
How can I trust the other person and make sure I do trust them if I'm going to work with them, collaborate with them or do anything with them and make sure I'm safe and my family is safe? So we've got to answer those two questions first and foremost. Money Back Guarantee does that, right? And establishing some credibility with these people. So I'm really looking forward to tomorrow.
No idea how it's going to go. I put quite a bit of time into it, hoping that it goes great. And if it doesn't, that we evolve it into something better and bigger from here. Just go bigger. I was reminded that today on a coaching call with one of my mentees, she was explaining to me that she's just having this epiphany that she hasn't been wanting to go bigger for fear that
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Chapter 3: What is the fastest way to monetize trust into revenue?
She would hurt other people or intimidate them and that she's finally getting to this place of freedom where she realizes she's got to show up as the real her as big as that can be. Otherwise, she's not shining her light to bring brightness and positivity to others. And that's an epic fail. So just go bigger. Just take the chance. It really will pay off for you.
But you've got to move through that fear moment, which I'm constantly doing. Okay, so one of the ways that I do that moving through the fear, I got frustrated a couple days ago, I wasn't selling enough tickets for this. And I had set up my page on Shopify. which is pretty simplistic and straightforward. And I've got all the credibility in the world on there. My book's on there, my testimonials.
My partner is from Harvard. He's a Harvard teacher. He's got testimonials on there. We've got so much credibility and experience between us. However, we weren't converting. So I look at the pricing. I look at the call to action. I look at the incentive. I look at the audience I'm communicating with. I tried a number of different things. Posting on social, obviously. Obviously. Right.
That's the simple answer, which I did at frequency. And I didn't see a big conversion on that. So I thought, OK, it's not working on social. I've got to look at email. Right. And I don't like to overwhelm the people in my email list because I send them one email a week. My goal is to add value to them and tell them a story that's going to inspire them and or give them attention.
Chapter 4: How to lead pricing conversations without fear?
or teaching they can apply to their life. So I don't want to lose them because I'm trying to push a product. That seems short-sighted to me. So I didn't want to send out just a standalone email on this and bombard them.
I went to social media and I sent a bunch of DMs to people that I either have been a guest on their podcast and given up an hour out of my day to support them or whatever, done things to support other people. I reached out to a few people just to say, hey, you know, if there's any chance you could help me or you have any ideas, how could I market this better? What am I missing?
Give me some feedback because sometimes we're too close to something to see where it may be flawed. And it was so funny. I reached out to my friend Brandon and I said, I don't know what to do. I'm freaking out. I haven't sold enough tickets. And he wrote back to me, did you forget what my business is? And I had.
And he owns a software company that's a search engine that can pull contact information, email addresses included on anyone by job title, by industry, by company. I mean, by anything and everything. It's amazing. It's called Seamless AI. This is not an ad, by the way. I'm just sharing with you the solution he presented me with.
So he said, let me set you up with an account and set you up with a training, which, you 2000 emails to people who are in sales or sales management positions and target them. And it's just one of those moments where you say, how much is out there that I don't know? How much have I even come in contact with that?
I've forgotten that I'm not applying to my business right now, which is overwhelming and why the goal is obviously to amass a team of.
experts in different arenas so that they can be focused on those things understanding what the best practices are and the most innovative products and services I'm just lucky that my friend was willing to share that with me and set me up so now I've got this account I've got this ability to search for people
based on their job and or industry and or company and then pull their email addresses in large, you know, fashion, I was able to reach 2000 people in one email blast. And now here comes the work, right? You start looking at what copy are you using? What is the open rate? You know, what value are you providing inside? Are you allowing for opportunity to convert there? You know,
Are you speaking to that right niche? Are you addressing their concerns, their pain points? Are you offering a solution? Is it a valuable one? Do they feel comfortable with the price point? You know, there's so many things that we can go back and look at through analytics and try to understand and continue to evolve and improve. And I'm really leaning into price.
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Chapter 5: Why do your lowest-paying clients often demand the most?
looking more at my open rates on my emails, looking more at how much value I'm adding, getting feedback from people and seeing, am I getting people on subscribing as well as putting new funnels out there to drive people to sign up for my email list.
And what I've found is a free ebook or a free accountability program, some type of free service that we're providing to others is a great call to action and or contesting, you know, works really well too. So You know, this whole cycle, it just it takes a lot of work. I'm going to be very candid with you. It takes a lot of work. I'll let you know next week if it was worth it.
I think that it will be. I think we're going to get some great feedback and strong testimonials. I will ask everyone to give me a testimonial, of course, as you should always should always be updating your testimonials and reviews on LinkedIn. You know, LinkedIn's interesting.
I've gotten a couple of different prompts in the past week to, you know, test out if you want to add your services, which I did add. And that, you know, had people messaging me. So I continue to take advantage of any offer that LinkedIn gives me because I want my profile to populate for others. So the more views you get, the more people you get checking out your services, what you offer.
And hopefully engaging with your content and then potentially being converted into customers. So getting them in that pipeline, in that funnel. So this week, my guest is actually a friend of mine. He is Cal Fussman, who is beyond famous because of his podcast, his journalistic work, his books. and the amazing storyteller that he is.
And it's so funny to me that we get into his whole fear around selling, his whole reframe that we needed to create. And I've been seeing that a lot lately with people, the importance of reframing. I was actually just working with one of my mentees on dropping, I think, from her repertoire. So let me show you what I mean by that.
Instead of saying, I think that this is a good idea we move forward with, saying, this is a good idea we move forward with. You make yourself a lot more powerful when you drop some of these filler words. So I'm going to challenge you to do that this week. Stop saying, I'm sorry. Instead, thank people. Stop saying, I think, and start just owning what the statement is.
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Chapter 6: How can fewer options create better sales?
Put yourself in a position of power and watch how people respond differently to you. I guarantee they will. Okay, hold tight. We're going to be right back with my friend, Cal Fussman. And yes, you're going to love him.
Confidence creeper.
Welcome back. I'm so excited for everyone to meet my good friend, Cal Fussman. He's an American journalist and author, writer at large for Esquire magazine. And let me tell you a couple of people he's interviewed. Mikhail Gorbachev, Jimmy Carter, Ted Kennedy, Jeff Bezos, Richard Branson, Jack Welch. I mean, the list goes on and on. And of course, the podcast host of Big Questions.
Cal, thank you so much for being here with me.
What a great introduction. Thank you.
We are laughing because the first time we met was when you came to my house over a year ago and interviewed me for your fantastic podcast, Big Questions. And we sat down and had a very interesting conversation.
The same view. I'm looking at you the same way. This time through Zoom. through the room, but this time you're actually closer. I think we're like 18 inches apart.
I know, right? That's so funny. Well, we were connected through a mutual friend who thought that we would hit it off and we did. And what was so interesting, and you discussed this on your show, was that while we're polar opposites, we're actually so much alike.
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Chapter 7: What pitch strategy gets decision-makers to say YES?
We've just come at business from opposite angles, me coming from the chief revenue officer position, you coming from the talent position, and both of us pivoting and becoming entrepreneurs and the challenges we both had to face along the way.
And you lifted me off the ground. I felt like a rocket ship as I was leaving your home. And now we've had this virus and everything has changed. And I feel like I'm in the booster rocket phase here. And I need the fuel to go off into space. And you are just the person to give it to me.
I am here for you, my friend. Now tell me, I want you to share because everybody else might not have heard this episode, which if you haven't, you got to check out the Big Questions podcast. It's a great show. And this was a really great episode. I've gotten so much feedback from people that gleaned some good sales tips from us.
You were struggling at the time with pitching yourself, pitching yourself for business. It was a role and a position you had never been in previously. And you and I sat and tried to talk about some different ways that you could step into that.
It worked so well. I was having my best year ever and really was poised. I was speaking for companies at conferences, going around the world, everything. It couldn't have gone better. And just as I was about to go off into the stratosphere, boom, this virus hits, every speaking gig canceled or postponed. And like you're suddenly looking around and what happened? Where do I go from here?
And I've come to realize I've got to go virtual. I've got to go through the computer, which was always one of my biggest fears. I'm getting better and better at it. Technology.
Why are you afraid?
Technology has always been something that from day one has just knocked me off balance. The best way I have to describe it, when I first tried to get an email, I was on customer support for like four hours to just try and get an email. And the poor person on the other end, like half of the day was spent working with me, and he just doesn't get it. Like, what's wrong?
Like you've done everything you need to do and it's not working. And then we realized that I was putting like calfusman.com. I was spelling D-O-T. Oh, so you asked me why I'm a technophobe. It starts right there.
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Chapter 8: How to effectively transition to virtual business?
It's interesting because I put out messaging on my podcast, letting people know I'm going to pivot, this is what I'm going to do. And I got a lot of response, but it's generally been from individuals saying, can you help me? Do you do one-on-ones? And so I have to think that way. But again... What really gets me is I know people are hurting now.
And so it's hard for me to go in and ask for a lot of money. I'm just not. I wasn't constructed that way. And I have to rewire my brain to think like that. This is what I'm worth. And this is the price. I'm sitting there thinking almost like a journalist. I wonder, are they on the edge? Are they just getting by? I don't want to take advantage of them.
So I'm looking at your eyes and you're saying, oh my God, I got it.
You know what you need to do? You need to go read your testimonials, your reviews and recommendations of your work. Go back and look at that. Go back and look at the value you deliver to other people because somehow you're forgetting that right now.
Yeah, I don't even think about it. I'm thinking about them.
But you're really not. And let me tell you why. If you were really thinking about serving them, you would focus on your deliverables and how you can increase revenue for them once you teach them your teachings. Focus on that. You are doing them a disservice, not giving them the opportunity right now. Allow them to make the decision. Wow.
But companies that are struggling, that aren't telling the brand story, that aren't telling the founder's story, that are disconnected from their audience, you can come in there and fix that for them. What is that worth?
You're right. You're a million percent right. And what I've just taken from... what you've put out in front of me is I really just have to look at this and feel bad if I am not going out and saying, let me help you and being as assertive as, as I possibly can. You know, this is a strange thing that happened, and it comes from being a journalist.
I know it because I was talking to a guy who's an agent now and who represents a lot of broadcasters, and he makes gigantic deals. And I asked him, Steve, where did you get started? And he said, well, I delivered newspapers as a boy. And it turned out we had both delivered newspapers for the same newspaper in Long Island.
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