Creating Confidence with Heather Monahan
Confidence Classic: How to Lead With Heart and Build a Culture That Rocks with Jim Knight
Tue, 27 May 2025
What if your leadership style could become your greatest legacy? In this episode, I sit down with leadership expert and keynote speaker Jim Knight to talk about what it really takes to build culture, develop rockstar teams, and lead with passion. Jim shares how he went from Gatorland and Olive Garden to training at Hard Rock Café and speaking on stages around the world. I also talk about what it looked like to show up on stage while navigating one of the hardest moments of my life, how I managed to cancel high-profile meetings, honor my son’s grief, and still deliver a high-stakes keynote that same week. Plus, I also answer your DMs about fast business pivots, launching with confidence, and MORE. In This Episode, You Will Learn 00:00 How I supported my son through his first experience with grief. 08:00 The BTS of delivering a keynote while managing emotional pain. 15:30 How did you start in the service industry? 25:30 Why “edutainment” is the future of speaking. 33:00 Jim’s 4 core leadership principles you can implement today. 41:30 What to do if you're working with a toxic CEO. 47:00 Advice for anyone who lost their job during COVID. 51:00 How to reinvent your business fast. 59:00 What happens when you bet on yourself? Resources + Links 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 Jim on Instagram
Chapter 1: How did Heather support her son through grief?
I don't even care what the product is. And I say this with love in my heart, regardless of people are selling widgets, it's never about the thing. It's not even about the environment. It's about the people. It's about the humans. It's always been about human behavior. The goal is don't focus so much on the thing.
Even if you're first to the market, even if you're crushing it compared to everybody else, the goal is you got to get spectacular people. You know, if you can find some rock stars out there, they will help you perpetuate the brand for all time.
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 today. Thank you for being with me. I need you. I have had quite a week, not a good one,
Of course, we can't have all good weeks, as we know, and I know that I'm definitely not alone. I'm sure you're with me in that there are just some weeks that suck, and this has been one of them. So the week started off normally, started off fine, actually, and then suddenly, tragically, my son's puppy drowned in... the pool. And since then, the last few days have just been a complete nightmare.
It's really been, you know, it's the first time my 13 year old has suffered from grief and loss and death. And it had been unexpected. I actually had said to him, wow, you know, at one point in a conversation I was having with him, geez, there are some things we can look to here. You know, when I first heard, I thought it was going to be one of your grandparents, you know,
And he explained to me that what I found really interesting, he said that wouldn't have been as jarring or shocking because you start to expect when people get older that things can happen. But when people are young and healthy, you don't ever anticipate that. And as much as I was trying to comfort him, you know, he was right. And I I really didn't know what to say there.
It's one of those interesting things when you're 45 years old and have gone through so much. I feel pretty equipped to handle basically anything that is thrown at me. And I'm not saying that's good, because in some regards, I think it's really jaded that I've seen it all. Go ahead, throw it at me and I'm going to handle it. But this one, I just I didn't have the words and it felt awful.
So I essentially just told him that I can't take the pain away. And I do understand how heart wrenching it is. But what I could do is promise to sit with him, to hold him, to be with him and to go through it with him. And that's what we're doing. So we actually made a great decision to leave home and go on a quick weekend trip with one of my really good friends and her son,
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Chapter 2: What is the BTS of delivering a keynote while managing emotional pain?
And it's been great because it got him out of the house. It got him into the ocean. It got him on a boat. It got him on a jet ski. It got him into activities which have gotten, you know, these little moments, these little breaks of sunshine and really his sad time right now. So I have not seen or felt sadness like this. And I don't even know how long.
There is nothing like watching your child suffer. It is much worse than any pain that I remember for myself other than when I was, you know, 15, 16, 17 years old. I remember looking back because I've been reflecting about this a lot. Things seem so much worse when you're younger because you don't have anything to compare it to.
However, you know, you're in some ways more hopeful and excited for things at that age because things are unexpected and new and and the whole world is new. Right. So there's this immense positive. And then I guess this really potential downside looming. Well, I see it that way now that I've actually gone through this with him. I wasn't thinking about that before this happened.
Time needs to pass. And obviously in time, he will learn to live with it and live with that idea of keeping someone in your heart and carrying them with you always. And we've been talking about that, although it's easier said than done when it first happens. One of my clients found out that this had happened and had asked.
actually seen a psychologist for someone, a child in his life when the same thing happened. And he was talking about some of the importance being around memorializing that animal's life and loss and, you know, if possible, doing something, even if it's just creating a picture or a portrait or something to showcase how special that person was and that they are still there in their life.
And so we are going to do that. My son had actually asked to do that. He wants to have a giant picture of him blown up for his room. You know, he came up with the idea to change his basketball jersey number to the date 14, the day that he had lost his dog. And so we're coming up with some different ways to make that special and memorable and rememberable, not forgettable.
And that's I believe that's important. So I appreciated that feedback because I didn't know, again, never having gone through this with my son before. So. This is life and sometimes life is just a bitch. So the day that it happened, of course, I had a full day planned of meetings and interviews and back to back. And my son was actually in his bedroom playing on his Xbox when I got the call.
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Chapter 3: How did Jim Knight start in the service industry?
And one of the interviews I had set up for that day was with Seth Godin, who is someone I wanted to have on my show for since day one. I mean, he's the world's best and biggest marketer. He's very difficult to get a hold of. And I had finally secured an interview with him that day. So wouldn't you know, that happens. And I first sat with my son for about an hour holding him.
And when I was able to get him calm, I came out to my computer to send out four emails to the four meetings I had back to back for the afternoon to cancel each one of them. And I basically said the same thing in each email. I said, unfortunately, my son has just suffered a tragic loss of his dog by a sudden unexpected drowning.
And I need to cancel my schedule for the remainder of the day so I can be fully present with him. I truly hope that we can reschedule in the future and that you understand. Thank you for your understanding. I sent basically that same email to everybody individually. And wow, you never know how people will respond, right?
You don't know who people are until they're thrown in the fire, until they're thrown into the unexpected. And A day or two later, I don't even remember anymore because this week is a blur. I checked my email and Seth had responded immediately. Oh, my gosh, this is horrible. I feel terrible for your son. I feel so much for what you're going through. Absolutely. We can reschedule whenever you want.
Sending hugs and like it was the nicest. Most supportive, understanding email. And it's interesting. I've never actually met him in person. I've consumed so much of his content. I've been to conferences where he's been a speaker and he doesn't directly know me. He knows people I know and I know people he knows. But it was so interesting to me to receive that message back. I was so grateful for it.
And just that gave me hope. There's good people out there. And sometimes they show up right when you need them. So that was good. So the next day, I actually I had a few one on one meetings with some of my clients that I really didn't want to reschedule with them. And they were late this next afternoon. So I said to my son, why don't you lay on the couch?
I have this one area that's my living room and the TV rooms, one giant room. And I sit in there to do my Zoom meetings. And usually my son's not in that room. And I said, why don't you just lay on the couch, watch a movie? I'll sit right here and record. If you need me, just wave your hand. I'll disconnect and get off the call. And he said that was fine. That would work.
So what was different was I was on these meetings, which typically it's complete silence in the background. And now you could hear that the TV was on. I didn't care because, listen, my number one priority is my son. And if anyone said it was an issue, I would just say, well, let's reschedule for another time. But no one said anything like that.
However, I was on one of these meetings with one of my clients who knows me well. And about 10 minutes into the meeting, he says, something's wrong with you. I don't know what it is. He said, you're off. You're upset. You're cold. I don't know what's what's going on with you. And I didn't want to say because my son was sitting right there. So I just said nothing. Everything's fine.
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Chapter 4: Why is edutainment the future of speaking?
If I had any energy in that moment, I would have laughed because I just know me and I know that, OK, I might be completely miserable right now and hanging on by a thread. However, I know that when the meeting launches in 24 hours and I have to go on and be the virtual guest speaker for this event, I will show up.
And this comes from lots of bad things happening and lots of difficult times in my life. I have had to show up and be at conferences where everything went wrong, where someone cussed me out, where, you know, where really difficult things were going on personally for me. But, you know, the show still had to go on and you still have to get on stage. And that's happened so many times isn't even real.
a thought that I wouldn't. Right. And it was funny. So the next day we were driving to the Keys and it was a really long car ride, four hours or something. And so I couldn't get any work done and whatever. It didn't matter. Anyway, I was just concerned about my son in the back seat and getting to the hotel, checking in, setting up so I could do the guest speaking for this company.
And so we're driving down and I'm just listening to music and listening, talking to my son and reminiscing about other trips we've had to the Keys over the years. And it was actually we had a really good ride on the way down, talking about what we were looking forward to on the trip and got to the hotel, got checked in, got set up.
I set the computer up, set the Wi-Fi up, set the microphone up, you know, got all situated. And then I said, oh, gosh, I got to jot some notes down about what the objective is. And what I always like to do is say to myself, what is the overall goal of this conversation, the speech that I'm going to give?
And so I thought to myself, based upon the feedback that I had heard from my client, because we had discussed it. the day before, he really wanted to congratulate and acknowledge the efforts of the team. He wanted to encourage them to move faster and achieve more for the next quarter, looking out Q3 and Q4.
And he also wanted to address an issue that was new in their world, which was they had a new competitor show up that was just trying to undercut them and price was becoming an issue where it really hadn't been previously. So I wrote those three things down, recognize and congratulate. Number two was encouraged to move fast and break things. And number three was the price conversation.
And so that's how I prepared. I'm mentioning this to you because years ago, that's not how I would prepare. Right. Years ago, I would have sat down and. probably put together PowerPoints. And, you know, I would have been nervous and not trust myself. That's not how I operate anymore. I really trust myself.
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Chapter 5: What are Jim's core leadership principles for effective teams?
Again, in all fairness, I've been in sales and sales leadership now for 25 years, more than that. And so I have a tremendous amount of experience I can rely upon and trust within me. I will have the words, especially when I'm going into any type of an organization that is revenue generation focused, that's focused on sales teams and on innovating and driving revenue. That's that's my thing.
So sometimes you just have to trust yourself and stop overthinking because I see that happen with a lot of people. It used to happen with me, but it doesn't anymore. So I had my three bullet points. And I dialed in. And once, you know, it was on, it was on. So I just I was completely immersed.
And thankfully, my good friend had taken my son and her son out for they went to go parasailing while I was doing this. So they were doing something fun, which allowed me to breathe and not worry about my child. And I was actually excited for him because I know.
When you're really down and then all of a sudden you put yourself in a sort of new scary situation like parasailing, you get so swept up in that moment. You're not really thinking of anything else. So that was I was excited, actually. And I couldn't wait to hear how it went because he was a little nervous, which I thought was good.
You know, it's like one of those opportunities to step into your fear and see if you have fun, which, of course, he did. So the speech went amazing. And one of the things that I address that I want to share with you is, number one, everybody needs to be recognized.
And being in good company is huge because when you're around people that are pushing you to grow and showing you what they can achieve and do, it motivates and inspires you and holds you accountable. Right. Because nobody wants to show up on a team and not deliver when everybody else is. So I was acknowledging that, too. I was acknowledging that. move fast and break things.
And I went back to two different times in my career. One time when I did that and felt so proud and really felt I left a legacy behind. And one time when I didn't do that, where I sort of just played to the middle and wasn't proud and look back and feel like that was a loss of my time, not being my best, not growing, not innovating.
And life's not about that, especially these days where we know how fragile life is, the coronavirus and all the loss we've seen this year. So I talked about that. Then I got to the point, the conversation around price and how there is no conversation for price when you have a premium marquee product, which this company does. They have an amazing product.
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Chapter 6: How to handle working with a toxic CEO?
And I challenged them to shift the conversation. Don't have the price conversation. In fact, focus solely on product and creating disparity between your product and the undercutters because they're not in your league. And you even allowing them to have that conversation that they are puts them in your league. So we're not going to do that.
Instead, let's use some different analogies and talk about why there is a vast space between and create more disparity between them as well as people make decisions on emotion right and especially now people are fueled around trust and safety concerns and poking some holes in that or suggesting you know fast forward five years from now jim if you buy a product based on price
and find out that jeopardized the safety of your employees and or your customers. Can you imagine what that would do to your brand? The brand you have personally worked over 20 years to elevate, the brand that your company has had for 50 plus years, is that worth losing over saving a couple of thousand dollars? These are the questions we really need to ask ourselves.
So we really talked through how you could handle that price objection. And I felt really good about the direction I gave them. I got some great feedback and then I was off and done. And I was so,
so grateful to have that done oh my gosh because I really had a heavy heart and I would just went it all into that moment and left my feelings and emotions to the side so that I could deliver that talk which random is so bizarre but I've done it so many times now that I knew I could do it and you can do it too if you actually have to so hopefully you don't have to anytime soon because it's not fun to be having a week like this however we all have them and we will all continue to get through them so
hoping that your week is going better. Hope you enjoy this next interview. And I will be right back with you. Welcome back. I'm so excited. As I mentioned, we have Jim Knight. He is the certified rock star.
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Chapter 7: What advice is there for job loss during COVID?
And the craziest thing, Jim, as I mentioned to you offline, is that one of the gentlemen in my mentorship program told me I had to have you on this show because he was blown away in person by you and your speaking abilities. So I'm so grateful for you to be here. Thank you.
Well, I appreciate it. And I will say that I'm mediocre at a lot of stuff. But one thing I have a strength is I can hold an audience. So at the very least in person, you know, our good friend Warren. Yeah, I'm super happy that he said that. Let's hope it translates to a podcast, right?
Well, I mean, I think you're underselling yourself a little bit knowing that you actually have your own podcast and have quite a bit of experience interviewing. So we know it's going to be good. All right. I want to start with, I grew up in the service business.
You know, I was busing tables, then I was working in fast food restaurants, then I was waiting tables, then I was bartending, ultimately leading me to sales. And I love that your story really begins and has that through line for the service industry. And I was hoping you could give us some insight in how you started out.
Chapter 8: How can you reinvent your business quickly?
Yeah, mine was sort of the same thing at an entry level. Actually, my very first job, although I will still say it's in the service industry, was at a local theme park. So I live in central Florida. I'm in Orlando. We have a lesser known theme park called Gatorland Zoo, which is an actual working gator farm. But, you know, for 14 bucks, you can go in there and there's a whole bunch of fun stuff.
I actually sold fish there. I drove a little miniature train out there. I worked in the alligator boa constrictor area where we would put like a snake around somebody's neck and you can hold on to a baby alligator.
What is this Joe exotic like in real time?
It sounds like it, right? I'm sure we probably crossed paths at some point. I doubt that actually. Mine was probably a little bit before his time, but I loved it. I mean, just having that service mentality, that work ethic really got me into working at a little Italian restaurant here in the States called the Olive Garden. And Olive Garden was a great run for me. I did that for a couple of years.
And although I went to school to be a musician and I was a middle school teacher for six years, my real love was in the hospitality industry. And I started working at a local hard rock cafe. And like you, I worked at a frontline position. I was just a host and loved it. But I got to touch basically 7,000 people a day doing something crazy like $35,000 hours, which is unheard of. hospitality.
But, you know, your skills grow real quick. And, you know, we can certainly talk about the service industry. But I think that that mentality, you talk about that through line has really helped me out in any position. And honestly, I get access to a lot of data.
And I'll tell you, the National Restaurant Association will tell you something like 65% of all Americans will work in that industry as a starting point. They may not end up there. They might not be their career. They're going to go on to whatever it is their school major was or whatever. But you think about in this country, 65% of all people have worked in that industry.
Man, it just really helps out, I think, when you go on to perhaps do something else in a different industry. So you and I have that in common. I absolutely love that industry.
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Chapter 9: What happens when you bet on yourself?
Yeah, it's been amazing and it's been really good to you. How did you transition from being a server, being frontline, being in the hosting position to ultimately leading Hard Rocks training?
I never really wanted to be a tipped employee, you know, which like you said, as a server, as a bartender, that seems to be a goal. That's where the money is. And then eventually you almost take a pay cut to be a manager, right? Because you're on salary and you're at the behest of whatever the general manager or the brand wants you to be. I never really wanted to be a tipped employee.
Like I said, I really, I liked being around people. I worked in probably the busiest restaurant in the world at that time in the early nineties. But I did think at some point I wanted bigger impact and influence and And so I did make the leap to be a manager.
And I think I was very cognizant of the fact that if I ever was to use my music degree, which I did get, performance and education, and the work that I had done as a middle school teacher, that educational piece, I wanted to pull all of those levers. I knew that I was going to have to be a manager at some point. So I did that really for only about a year, year and a half.
and then transcended over into the training and development world. That meant I came out of the cafes. I was working at the corporate support center. And ultimately, when my boss left to go do something bigger and better, I was just sort of a natural to move into that role and wound up staying out of, I think, the 21 years.
I think I can add up to about 16 being head of the training and development wing and loved it. And then from there, it was cafes, hotels, casinos, live music venues. It was global. And I got a chance to travel to about 60 or so different properties in some 30 different countries.
So, you know, just really, again, that work ethic, like you talked about, Heather, is it really kept me grounded when I became a manager and ultimately an executive. And now I got a chance to, I guess, see the world and hang out with some rock stars. And somebody was paying me to do that and look and be and say whatever I wanted.
So it was definitely a charmed life or at least a career, a lifetime career that I loved, just absolutely loved.
It sounds like you didn't know that that was going to be your career, though, when you started out, right? Because you were so interested in music. However, you've almost created this new arena, this edutainer type arena, which I don't see many people doing that.
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