Hey, hey, welcome to the Summit Host Hangout Podcast where you'll learn how to host a high converting virtual summit that leads to your biggest signature offer launch yet. I'm your host, Krista from Summit in a Box and I have a guest today who I am literally giddy to share with you like, beyond excited, I couldn't even hardly like sit still long enough to write an outline for this episode. But more on why that is in a minute. We're gonna give some more background on a specific situation here once we dive in. But it's become very apparent to me that we have some people around here who could use a little boost in their selling mindset, which I know is no news to our guests today. But it's become very apparent to me. So I have a couple of questions I want you to think through when you think of selling through your Summit, do you instantly start to feel uncomfortable? Do you worried that you aren't allowed to make an offer throughout or at the end of your Summit? And heck, maybe you are even like me, and you've literally had people tell you when and where you can sell where you're allowed to sell and that feedback has you feeling a little uneasy. If any of that rings even the slightest Bell this episode is for you. To give you an introduction to our very special guests. She's a mindset coach and business mentor dedicated to helping her clients create more ease in their businesses and lives. Her support blends strategic thinking with inner work and a whole lot of self love. And this supports her clients to step into more alignment with their offers their business models, their values, how they want to lead and and even more so they can continue to grow their impact and income in a way that actually feels good. She has been in business for over seven years building to multi six figure businesses. She has trainings in NLP or RT Human Design and more. She's coached many six multi six and seven figure entrepreneurs and she just happens to be my coach who if you've been around a while you've heard me gush about a time or two, most recently in episodes 209 where I talked about creating space and owning my offers. And again in Episode 231. Were giving me your update. I even have a another episode outline sharing the top investments that have led me to the most growth and sustainability in my business and you can bet that she is at the top of that list. I am not exaggerating when I say that working with her has truly changed not only my business, but my entire life, the way I show up everyday how happy I am, how present I get to be with my family. Even my husband makes comments about how incredible she is and how happy he is that I have her in my corner so I could go on forever. Before I start crying now I'm going to stop. So let's dive in and talk with one of my very favorite people on the entire planet. Caitlin Kessler, welcome Kaitlyn.
Hello. I'm Kaitlyn. Starting it off with a little bit of tears. That's, I'm so happy to be here. Thank you for such a beautiful introduction. That's okay. Yeah, podcast, let's do it.
I didn't expect to get teary eyed either, but get the best and everyone's gonna they're gonna see that. So let's see. Let's let's refocus. Why don't you tell everybody a little about you and your business just like the pieces you want to share?
Yeah, yeah. So that little like blurb I feel like really encompasses so much of my work really well. At the end of the day, like, I really want people to feel good running their businesses, like that's my main goal, the main thing that I'm trying to do, and there's a lot of strategy that goes into that, a whole lot of mindset that goes into that. And I just feel so fortunate that I get to work with people who are at the point where they see the value of that, where it's like, okay, I get it, I get how to do business enough to like, pay my bills and things like that. But like, I want it to feel good, too. I want it to feel fulfilling, I want it to feel like this is something I can do for a long time. And so I'm just so fortunate to get to do that work. My clients are typically people who really are on a journey of finding more ease and more spaciousness, and like continuing to grow their impact and are ready to do it in a way that just doesn't suck life out of the for like the lack of a prettier way to say that. And so I'm so fortunate today, I've been doing that since about 2019. Before that, or it I also have a design business that have been running since 2015. And yeah, I just, I think the blur really covered my whole little thing. But that's, that's what I'm here for. I'm here for doing things that make you feel good in your business so that you can make a lot of money have a huge impact, and do it in a way that supports your whole life.
Seriously, you're so good at and think back to like, you know, it's funny to think of your goals when you first start out in business. And it's like, I want to make this much money. I you know, okay, now I need to make this much money. And then, like, for me, I got to a point where it's like, okay, I'm making the money, but this sucks. Like, this is the worst. And you fix that. But no, it's to the point where whenever something new comes up, I'm like, Oh, this doesn't feel good. I go running to Caitlyn. And that's, that's where the idea for this episode came from. And I want to kind of set the stage by sharing a little of that story. So a couple months ago, as of recording this, I hosted a three day workshop. I felt so wonderful about the content. I poured everything I had into that. I went back and looked after what I'm about to tell you about what happened. It's a 48 page content out line like very detailed content, I did not hold anything back. And throughout the topic, it made sense for me to mention our accelerator program here and there. And again, I went back and counted on the day one outline, I mentioned it two times in passing, I literally like said the name of the program when I was given an example of something. And that's it another two times in passing on day two. And then because of all of the questions that were coming up around it, I did end up making a full offer for it. On day three, so many people were asking about it asking for details on the exact strategies we covered during our q&a. Like, it just made sense. And it felt so alarmed that I didn't think anything of it. And I am really sensitive to that stuff. We actually hosted another workshop style thing last year. And I had planned to make an offer, it did not feel good to me on the final day, and I didn't end up making it. So like, it's not like I just pitch, any chance I get it's like if it doesn't feel good, I'm not going to do it, it felt so good. I thought nothing of it was like that pitch serve people so well. But then the feedback forms came in. And you know, most of them are wonderful, but you don't focus on the wonderful ones, you focus on the crappy ones. And I had two responses that really threw me for a loop. And one was basically along the lines of Why are you such a broad marketer. Your programs are so great. Why do you do that, and then another person literally going through reasons why I shouldn't have been allowed to do that. And pointing out where I am. And I'm not allowed to sell in my business and just like nitpicking everything and tearing it apart, and man, it threw me off, I felt I was feeling so good at that point. And I was just crushed by those things. Because someone might call me eyebrow marketers like my worst fear, like, I sell confidently, but I don't want it to feel gross, you know. And so I brought that to Kaitlyn. And she she coached me through it wonderfully. And the next time I deliver that workshop, I will do what I did before. And I will feel just as confident about it as I did before. But it opened my eyes to just how much people in this audience specifically need to look at selling differently. And that's why we're here today. So Caitlin, I'm curious, like with you thinking back on that story, what are some of your initial thoughts around it? And that can be like, in any direction you want to take it?
I think what we had talked about and what felt really clear to me when when you brought that was just the idea that if somebody was feeling that way, about their experience of going through that workshop with you, that it probably spoke more to their own qualms about selling rather than you actually selling, if that makes sense. Like almost like just it was more about them than it was about you kind of thing. And I thought that can be like an answer that is like, Oh, well, that's nice, but it still kind of feels bad to receive those forms. But I think you were so brilliant and being able to understand that. And then to use that as a jumping off point to help your clients and your customer base through this journey. Like I just think that you're so brilliant for like being able to say, Okay, let's remove like the, you know, the hurt feelings from it, we can we can work on those, and we can work through those two. But there's a real opportunity here. And like using that and creating content around that, and really helping your people start to understand that selling does not have to be this like gross, icky thing, even if they're going to project it on you just a little bit. But that's my initial thoughts. And then, you know, there was a little bit of my, my sassy Kaitlyn Thoughts where I was like, You know what, but we don't go down that path too much. But I did get a little defensive because I know you and I know that you are like, just not a bro marketer, and you give so much value. And you like asked me I saw the outline for that workshop, there was just so much goodness there that how could it not lead to the next steps of coming into that program. And I think that that's what is really interesting when you think about selling and why it might feel icky, and why it might not feel like something you want to do. And it's probably because either there's not a lot of value being given, but probably more likely is that you don't realize how much value you're giving, like you're not giving yourself enough credit for how much value you're putting out there. And I see this with clients all the time in various offers like, well, you know, I do have a podcast, and I do post on Instagram all the time. And I do do this. And I do do that. But I just don't know if I can really sell it. I'm like, Oh, so you're just like value vomiting all over everybody. But that's not enough. Like when is there enough that you get to say now, would you like to take the next steps with me? You know,
I love that. And I'm curious, you mentioned like your one of your initial thoughts as well. It's more about them than about you. And I remember when we were having this conversation you had pointed out like they had some experience in the past that put them in a place that they have very negative receptions to any type of selling. Do any examples come to mind for you of what that might have been? That kind of puts people in that place?
I mean, I think depending on you know, different industries that people are in, I can speak to the coaching industry a little bit, but I'm sure you have an audience that's in different industries too. But there can be the experiences of investing in something and it not being delivered to the expectations that you had for it, or the promise kind of not being fulfilled. And I think that that is a concern in the online business space. But I also think if they've been in your world if they've ever speaking specifically to you, but also I think people could apply this to their own their own Summit, or or anything, if they come into your world, I know that they're getting so much value, they're getting value from this podcast, they're getting value from your Facebook group, they're getting value from all these different things that they should already have this understanding of like, the quality to which you deliver the testimonials, the client experiences that you share, like they should already have that kind of understanding that you're not swindling them, even if they have been swindled for lack of a better word. In the past, like, I think you can show people that you're not another one of those experiences by sharing about testimonial sharing about what's inside of your programs, saying, This is what you're gonna get when you log in and see everything or this is what you're gonna get when you come to this summit. Like, you can just kind of just like answer that question calm that concern by showing, you know,
yeah, I love that. And I feel like, I got a lot of my confidence with showing up in those ways from you like both from your pep talks and your coaching, but also from like, watching you model it. Like, I feel like you are such a confident seller, but anyone who called you a biomarker would like literally be silly in my eyes. So like, we're Is there a line for you? I guess, is there a line for you with selling where you're like, This feels good versus this feels
gross. We've both been in the online business space for a really long time. And I think I mean, I'm speaking for you, so correct me if I'm wrong, but like we've seen kind of that rise of like the bro marketing staff and seeing it work and seeing a lot of success stories, and then being on the end of like, kind of feels gross. Like, I don't want to do that. And so when you check in with it, for me, what comes up is, it feels gross to to, to think of people not as people to think of people not coming in with their whole human experiences into my world into my offers. And to just think of them as like, a number or a data or a statistic point, like something like that, that feels really, really gross. And so if I ever find myself, and this is normal, right? Like, I'm not like, there's no judgement here. But if I ever find myself in a thing, where I'm like, I really want to make this sale, I really want to hit this milestone, I really want to hit this goal. If that starts to take over the like, oh, there's a human here, that's like thinking about making a significant investment with me. Like, if I gotta check myself, I gotta like, pause the conversation, I gotta be like, let's go back to like, connecting with what we're actually doing here and how we're actually showing up for people and who we're actually serving. And that at the end of the day, like, while I like tracking the data, and I like knowing the numbers, and I like hitting the milestones. That's, like less important to me than serving the human because I know, the human, all those other things are gonna fall into place.
Yeah, absolutely. That can like guide, how you show up in every other way. Like throughout your whole funnel, I feel like something else that you've helped me with that has helped me show up more confidently when it comes to to selling is you've helped me see the fact that talking about my programs, and putting them in front of people is truly doing them a service. And I want 100% believe that when we started, I could have said that I believed that and like Matt, actually, but now I 100% believe that I can serve them so much better in our accelerator program that I can hear on this podcast, or that I could in that workshop that I did, or by giving little tips here and there on social media or to my email list. So I guess I want everyone to hear a little about your take, as selling as an act of service.
I think how you just kind of like lead into that is a brilliant thing to think through, we can give so much value through our different platforms right through our podcasts, or even through our summits, like we can give so much value. But at the end of the day, it's not going to compare to what it's like to have that like very personalized touch, to have someone that's like in it with you like going through with you like line by line, which I know you do for your students, right like to actually be reading the different pages and giving the feedback and things like that, like it's just incomparable. Right, the tips can help someone could listen to your entire podcast and listen to all the episodes and take all the notes. And they could do something on their own for sure. And they probably have a great experience. And they would have a significantly different and probably better experience. Being in mind your programs and having you like with them, helping them kind of like holding their hand in a way not like in a you know, what's the right word like infantile lysing. But like, no, just like I'm here with you. Like, I know what's coming up for you right now. I know that mindset stuff is coming up. I know the concerns that are coming up, like helping guide them through it. And so for me, it's a service to say, Yeah, you could do this on your own and it'll be better if I can do it with you. Like it's, it's a kindness. It's like, I'm someone who has no problem asking for what I need. I can cook for myself a more adult human who can do that she like make the food that she needs to eat to survive. It is so much better and more fun and I better experience better results for sure to say hey, will you help me with this? Can you teach me what it means to last night we took we braise something we glazed like it just, it's, it's better to have someone there with you to help you guide through it and like to get you that personalized attention. And so to me, it's such a service as a yeah, go do it on your own totally. And I could help you, I could take this a step further. I could really guide you through this, I could be there with you through the highs and the lows of it. I don't know any other words. Besides that, it's such a kindness to say like, I got you, you know.
And I can think through your stuff in the same way I buy everything. Kaitlyn sells just FYI. Whether it's $5, lots of 1000s of dollars, if it's a free thing, I'm there, sign me up. But you can bet no matter what other things I'm going through, like, I'm going to still be a part of her one on one coaching, because I have seen like, it was such a kindness of her to be talking about that offer, over and over where she did on social media on her podcast until it hit me at the right time. Like, oh my gosh, I need this. I am so thankful for all of that selling that happened. Now I'm hoping that people listening can kind of start to see that with their offers, how their offers serve their people better, what would you say to someone who just feels uncomfortable in general talking about their offers?
Yeah. So I think this is a really good question. Because it opens up, like if somebody came to me, they're like, I'm just uncomfortable with this, like, I'm uncomfortable with this idea of selling this offer. I think there's like a lot of avenues that it could go down. And I think it's a really great entry point into, okay, is it about selling? Or is it about your offer? Is it about your competence, like, there's so many kind of doors that we could open. And what I find a lot of times is that when people feel really uncomfortable selling, it's actually about confidence around their offers confidence around their ability to deliver their offers competent, that their offers are good enough and things like that. And so those are kind of like easy things to work through. Okay, what's your offer? Like? What needs to be changed about what needs to be tweaked about it? What, like, where are you? Like, I think back to that, like InDesign days? And I'd be like, yeah, I could totally go into your WordPress website, I didn't want to sell that package, because I didn't want to go into your WordPress website. Right, like, that's, that would be much harder for me to sell. Because as your confidence isn't there, and there would be a part of me that knew was like almost out of integrity to sell that, right. And so I think there's a check in there, like, Are you good with the offers, and you can always tweak and change your offers to make sure that you feel really confident about it. With a summit and like selling things in that I feel like there should be so much competence there because you're selling, it's not like you necessarily hand delivering something or right most of the time. And so there's so much room for competence there. Because it's like something tested and tried and true. And they can take it and work with it and like run with it. So I would start with that. Like what's really the problem here it is really just selling like, it's hard to say, I have this thing to buy, it's time to reconnect with the benefit of that for the person buying it. What's in it for them? Why is it so good for them? What is it going to change about their lives, about their businesses about whatever it is that you're, you're supporting them with? Like, stop making it mean for a little sassy, believe stop making it about you. It's about them and what they're receiving and the benefits of them. And that's really where we are attention?
Yeah, absolutely. So like it starts kind of like with almost a gut check. And that might be simplifying a little too much. But like, I would imagine most people can fairly quickly kind of identify what piece of the puzzle is making them feel most uncomfortable.
Yeah, like, I think the question is, let's, whatever the thing is, whatever they're selling, if you sold like whatever number is like dramatic, 10 of them, 100 of them 1000 of them, like depending on how high touch it is right? Like, would you be okay with that? Or would you be like immediately in panic, because you can't actually do that, or you don't know how to do that. Or you don't know how to hold that like, okay, maybe time to just check in with the actual like, thing that you're selling and make sure that you feel like 100 on like the integrity check on that, that gut check on that. I'm assuming if they're in your world and all of that, that that's probably like, good. And so if it's really just about the selling thing, then it's like, Okay, why don't you want to help people? Why
don't you want people to go through this experience with you? Why don't you want people to have the result of this or the outcome of this? And I say that like kind of like jokingly mean, I hope that that comes across as a joke, but like, why don't you want to help you? And then coming up with okay, it feels like it's not actually helping people. Okay, how can you make the selling experience even more, like valuable even more helpful? How can you really lead from this place of like, I know this is gonna serve you if you're this kind of person. If you want this kind of result. I know this can help you get there. Like just, it sounds. So it sounds so simple to say like this, but if there's parts that feel really a year out of integrity, those are just opportunities for you to do it a little bit differently to say it a little bit differently. Like I don't use a ton of scarcity because for me personally, I have not under way to do it, that doesn't feel a little bit like that's not to say scarcity is bad, and that it can't work for other people. But like, for me with my own gut check, I haven't mastered a way that feels really, really, really good for me. So I just don't do it. I create urgency in other ways, you know?
Yeah, I think, I don't know, I've definitely been guilty of this. And you've helped me through it sometimes, like, I've definitely been guilty of following other people's strategies so closely, because I want to do something that's proven something that works, then ends up feeling terrible. It's like, oh, my gosh, this is the worst. And it's always like, Okay, you just need to make this tweak that goes from that makes it go from their way to your way. And I just feel so much better. So that's probably a huge part of it. For people too, and it's definitely helped me. Something else you helped me through with it was a challenging quickie. So you should tell people a little bit about quickie. And I don't remember exactly what challenge it was. But basically, you made me cell for every single day for a month in different capacities. And you get really used to it, when you have to do something like that.
We I don't remember, which hasn't been a selling specific one. So you must be it was
some kind of discomfort type. Oh, fun.
I love that cookies is fun, because it gives you the opportunity to do the things that you're kind of like about and like, I think a kind of fun creative way. But yeah, I am someone this is something that is still true for me. Now, as soon as I say, Oh, I'm launching something, there's like a little clique in my brain where I'm like, I've got to sound smart, I've got to do good things, I've got to like, there's still this like little, little tiny like thread in my brain that hasn't quite been rewired. And so I don't think about it as launching, because that word just kind of like makes me kind of do something weird in my brain. I'm just like, Oh, I'm just gonna talk a lot about quickie right now, or I'm just gonna talk a lot about these mastermind right now, or whatever it is. And that just feels so much lighter and easier. And then suddenly, I am a human again, who knows how to talk like a human. Just share about my offers, right? And it's not like in this offer, you will get this, this and this. I think there's a time and a place for that. Like, I think that those emails are important, right, like and helpful. Because there's people that just need to know, you know, the facts of the offer. But for me, like it's easy to sell daily, because I can just talk about things that I like talking about. And turns out my offers talk about this same thing. That's like, a no brainer to say, Oh, if you're someone who you know, struggles to sell daily, like inside Quickie, we have challenges that you do every single day and a selling one is coming up soon. So you could join ASAP.
I'm not looking forward to that. But it's gonna be awesome.
Yeah, but I think it's I think I've gotten away from your original question. But I think if the word selling is like, kind of has a weird connection for you, maybe it's just like, oh, I talk about something to do with my offers. I talk about something to do with anything that I'm doing. Like, I'm trying to think of how this could fit into a summit specifically. And I'm sure that your audience is capable of like applying it. But like, if there's something that's in, you know, one of the All Access Pass, or whatever it might be, if they're selling a course at the end of it. Like, if there's a relevant moment, when you're talking about something to say, oh, and we cover this in my course. Just say it.
Like, just, that's all you have to do. Yeah, doesn't have to be weird. It
doesn't have to be weird.
I love that. Yeah. So I think I think we've given people a lot to think about from that standpoint, like, how you can if you feel uncomfortable selling right now how you can start taking the steps to feel more comfortable. I'm curious if you have any thoughts for people, kind of on the flip side here who tend to view other people selling as something negative? So maybe they heard us talking about quickie just now and they're like, or if they would have been on that workshop, maybe they were one of the people who filled out those feedback before. Like, what would you say to them?
I think this is very mindset II what I'm about to say, and I can poke holes in this theory. So this isn't something that I like capital T truth, but I do think it's an interesting idea to play with. What if a lot of those things were you like the things that kind of trigger you or make you kind of like roll your nose or whatever, like, what if those are just opportunities for you to investigate how you feel about something investigate if you want to continue to feel that way, etc. So like that example, if it felt really gross for you just now to hear me say anything about Quickie, okay. Why is that how you feel about talking about your offers to? Is that serving you, your business, your audience, your clients, your potential clients? Or is there just like room there to do a little bit of digging and a little bit of investigating into how that I fully believe that that program can really help people? I have a lot of evidence, but that program can really help people There's nothing gross about me saying, hey, I can help you. Likewise, there's nothing gross about you saying, hey, I can help you. Like, let's just take it out of business for a second. If there was someone right now like, Okay, I'm sitting, I can see out my like, the front of my house, if there was someone, like, suddenly, like stumbling when they were walking, because it's really hot outside, like, I would go help them, I wouldn't bring them water, I would be like, do you need to come into the it's like really hot today? Do you need to come inside? Do you need air conditioning? Like whatever it is like I would help somebody if I can help them. And that's how I think about my programs, I would they can help people. I'm going to offer them, you know?
Absolutely. I like that. I feel like that one's almost would almost be trickier for people to overcome than the other way around. But maybe not. What do you mean, I feel like it would be trickier to change a negative mindset that you have when you're thinking about other people selling than if you just kind of felt uncomfortable about your your own. But maybe maybe the two are always intertwined. I don't know,
an exercise could be I love this exercise. If that's true for you, if you're like people selling I hate that that's so gross. I would love for you to think about like, five things that you're really grateful that you were sold. It doesn't have to be in the business context, right? Like, I'm so grateful that I was sold on the like Revlon round brush blow dryer thing. Like it's a game changer, right? Like, I'm grateful. But I saw so many people on Instagram, promoting it like two years ago or however long ago, because it like makes blow drying my hair is so much easier. And like, it's kind of like fun to feel like I know what I'm doing even though I don't know what I'm doing and kind of makes me feel like I'm getting myself a blowout even though I don't know what that actually means. Like, I'm grateful that I was sold on that. And that might sound really silly. But like, I know, people have experiences and things that they're really grateful that they were sold on. So look at that, like look for that evidence that it can be a good experience, it can be a good thing.
Oh, I specifically love your example. But that's, that's really great. You know what I'm talking about? Yeah. And I also do not know what about is so I really appreciated that comment also. Oh, my gosh, well, okay, I think you've given people a lot of good stuff to think about here. You know, whether you're someone who feels uncomfortable when other people smile, or you tend to be triggered by it, or you just kind of clam up and feel a little anxious. You get butterflies when it's when it's time for you to make a sale. And especially if you're hesitant when it comes to selling in the in the summit context. I hope we've given you some steps to start thinking through here. Kaitlyn, I'm curious to hear what's the biggest takeaway you'd like people to get today from what we talked about.
I mean, like really simply that that selling doesn't have to be this like negative bad thing. But maybe more specifically, is that you are doing good things in your business. You are doing good things in your summits, like you're, you're here to help people. And the more that you can stay connected to that the easier selling is going to be.
I love that. And yeah, everything you do is so helpful with locking people through that also, and I secretly not a secret anymore. I just want everyone to be as obsessed with you as I am. So please tell the world where they can go to learn more about you and connect with you and see your offers and all that good stuff.
Oh, I love that. I love that. I'm obsessed with you. So yeah, I'll take Oh, I'll gladly have more views. And so I'm mostly on Instagram. Caitlyn s Kessler there. I have my own podcast. And I was asking Krista when this episode is gonna come out versus when we were recording it because the podcast is evolving and changing. And this is my first time like saying that even though this won't be released yet. And so I will I have a podcast, currently at time of recording called effortless that has like almost 200 episodes, and they're all really good. By the time you are listening to this, there'll be a new podcast, we're between two names. I don't know. Should I say both of potential ones that
weird? No, go for it. I love it. I'm curious. So either gonna be I'm curious to
see your reaction. It's either going to just be the word spacious, or it's going to be the spacious CEO. I'm not fully committed to either of them. But the gist is the same. Really helping people create like that ease and that spaciousness in their life and business. So I'll have that podcast, there'll be probably, I don't know, 20 episodes by the time this episode airs. So I'd love more up there, my website, Caitlyn kessler.com.
And like, seriously, go check out all of her things because they're all incredible. You will not like go in a bad direction. When you go check out Instagram, her website, her podcast, her old podcast, any of the things and we'll link to everything in the show notes too. So thank you so much for being here. Caitlin. This was so fun to get to chat with you. And thank you so much, everybody for tuning in for shownotes and resources mentioned links to everything that Caitlin mentioned, head to summit host hangout.com/ 248. Now go out and take action to plan, strategize and launch your high converting virtual Summit.
