Summit Sessions with Bryan Schielke
Summit Sessions with Bryan Schielke is your go-to podcast for insights on leadership, business growth, and relationship-driven success. Hosted by Bryan Schielke, Co-Founder and COO of Summit Group Solutions, each episode explores the strategies, stories, and lessons from top entrepreneurs, business leaders, and industry experts.
Whether you’re scaling a business, building meaningful professional connections, or navigating today’s fast-changing market, Bryan brings actionable advice, real-world experiences, and candid conversations to help you elevate your potential and reach the summit of your career.
Tune in and discover how speed beats perfection, relationships drive results, and curiosity fuels growth.
Summit Sessions with Bryan Schielke
Lauren Bailey – CEO, Factor 8
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What actually separates a top sales rep from a great sales leader?
In this episode of Summit Sessions with Bryan Schielke, Bryan sits down with Lauren Bailey, a sales leader, trainer, and founder who has helped hundreds of organizations transform how their teams sell, coach, and grow.
Lauren breaks down why the jump from rep to manager is one of the hardest transitions in business, and why most leaders struggle to make it successfully. She shares how top performers often fail as managers, what companies get wrong about sales training, and why most training never actually sticks.
The conversation goes deeper into what real behavior change looks like, how to build coaching cultures that last, and what relationship-driven selling actually means when targets are high and pressure is real.
You’ll also hear powerful insights on leadership development, the hidden barriers holding high-performing women back from leadership roles, and how authenticity and community play a critical role in long-term success.
If you lead a team, build revenue organizations, or want to grow into leadership, this episode is packed with practical, real-world insight you can apply immediately.
So, Lauren, you've built programs that help reps hit quota faster and help new managers stop being super reps and start leading. What's the biggest shift that separates a top seller from a truly great sales leader?
Lauren BaileyOh my God, there's so many. And it's the hardest jump to make. I've trained a lot of people around the world. And the hardest shift is rep to manager. The second hardest, by the way, is inbound to outbound. And then third place is service to sales. So, right, you keep track of those big challenges so that people understand, like, oh, okay, what you're embarking on is a big deal. It's really common to promote our top reps into managers. Not because every sales leader in the world makes the same mistake on purpose. These top reps want that, right? They want to keep growing in their career. I was speaking to a room of about 10,000 sales leaders once and asked that question, right? Who's made the mistake? And Brian, every single hand went up in that room. So the biggest difference is here's here's where we struggle the most is what makes a top seller is a very different DNA than what makes a successful frontline leader. And by that, it's the W, right? The name of that genetic thread is the win, right? It's the win gene. Top reps are super competitive, right? We're kind of coin operated. It's me, me, me, me, me, right? If you've ever had a top rep, they're like a puppy, they need a lot of attention, you know, good job, a lot of that prick. Also, they're so good they don't know why they're so good, right? To them, it's an art, not a science. So those two things work against them because in that shift into frontline leadership, what happens then is it's not about winning the deal anymore. And it's not about you getting to be competitive. You have to be fueled by other people's wins. And they're going to do them differently. It's going to take them longer, right? It's a pass-through high, if you will. And that can be a struggle for folks. So what do they do? They jump on and close the deal anyway. They jump in to save the day because that fuels that need a little bit. And of course, doesn't necessarily help develop the rep behind them. That's the hard part. And, right, that art versus science, right? It's hard for them to teach. Coaching is sales manager's number one worst skill, cataloged year after year after year by CEB. And uh, it's a really tough skill to teach when to them it's an art, right? So instead, they just wind up saying, hey, be like me. Here's how I would do it, or taking over. And those are some of the most common coachastrophes that we catalog at Factory.
Bryan SchielkeCoachastrophes. I love that. That's fantastic.
Lauren BaileyThere are plenty. Yes, there are plenty. It's you have to kind of unlearn some behaviors, right? If you there's a really old book called The Leadership Pipeline, and it creates this visual that says, you're going up in your career. Awesome. Now, when you pivot, it's not more in the same direction. It's a different direction. And to be honest, you have to go backwards and unlearn some things in order to then go pivot. So we're unlearning the W at all costs, right? We're unlearning the let me do it, let me solve, let me do everything. And we're then we're learning the skills about giving feedback, having difficult conversations, delivering good coaching.
Bryan SchielkeThat makes sense. Absolutely. Well, thank you for that. That's terrific. All right. Uh, next question. Factory eight's been recognized repeatedly for training curriculum, but you've also been on the buyer side of training that fell flat. What do most companies get wrong about sales training RLI? And what is getting the setup right actually look like?
Lauren BaileyOh man, these are great. I got to change my background when we talk about that. Oh, it's factory eight. This is what happens when you're a serial entrepreneur, right? You've got so many different lanes. Um, but factory is my first baby. It's almost 20 years old now. Before starting Factory, like you said, I was a sales leader, but also an enablement leader. I was launching sales teams around the world for IBM and SAP. And I was trying hard to buy curriculum to help me, but it didn't exist out there. Virtual sales was new, right? And 90% of what you see out there in sales training is really still rooted in that kind of old model, right? The elevator pitch. You try to deliver that over the phone and you're getting hung up on it. It just doesn't work. You have to struggle, isn't the conversation where you can value or spin or challenge. The struggle is getting the damn conversation and inside sales, right? And so those tips and tricks to use the phones was what drove me to build the factory curriculum. But what I learned, right, is enablement teams, we all have a dilemma of build versus buy. Everybody does. I want the outside expertise and the speed of a vendor, but I want to own it and I need it customized. So I want to buy, I want to build, right? But my team may not have the bandwidth or the expertise. So there's always this struggle. And what winds up happening is we bring in an outside expert, they deliver their standard two-day program, everyone gets excited for a day or two, and by the end of the week, we're back to doing everything the way we used to do it, right? There's like five or six documented scientific phenomenon that prove people's brains are hardwired to resist change. They are. And so we have to throw the kitchen sink at it if we really want behavior change. We should be hiring psychologists, not necessarily sales experts and trainers. So I think that they built most of the industry builds the programs wrong. That's the truth of the matter. So what we built now over the years of learning, right? We started with the same old model everybody else did. Hey, let me come in for two days. Then, oh, I guess I'll just add one follow-up call. Now we work with the leaders ahead of time, we customize everything. The programs are a year long, stretched over time, not two days. We kick off with executive leadership, we pre-measure all the baseline metrics, we train the managers first, we do accountability sessions every single month post-training, and then load the managers with tools that make it fast and easy to do the coaching well afterwards. So, like the kitchen sink has been thrown at this thing, right? And there's five or six other ways we go in and help keep it alive because it's not, it's not just the magic in the classroom, right? And there's plenty of things we do wrong there. It's what we're doing to keep it alive afterwards that truly determines whether or not there's going to be any RLI. Whether you're building something internally or bringing in an outside vendor, you've got to look for the customization. You've got to look for the integration of the managers, you've got to look for what's in place. What is the process or system to keep it alive? Right. And access to online videos or one follow-up call is just not going to beat the brain's hardwire to resist change and go back to old habits. Does that make sense? Does that answer your question?
Bryan SchielkeAbsolutely. Yeah. And you gotta, yeah, you gotta keep those guardrails high.
Lauren BaileyNo kidding. And then you gotta pave the road and then you gotta go buy a bus, get everybody on the damn bus, right? And have a really great driver throughout. And make sure your leaders aren't hopping off along the way, because the thing about being in the training and people development business is that it's never on fire, right? Like no sales leader gets a call at midnight about somebody not knowing something, right? We're gonna lose a deal or everything trumps this thing that we do. I used to joke, especially in down economies, that we sell vitamins. Like everybody knows they're supposed to take vitamins, right? It's good. It's good for you. You should be doing it. Keep yourself healthy, go to the gym, see your doctor. But when times are rough, we buy vodka. And so it can be difficult to do. We developed something new this year that is one other way that I think the training industry has been broken for a long time. You know, it takes a sales leader to come in and bust open a different industry, right? Because you see it from a different point of view. That build versus buy issue. We solved for it this last year by making our programs theirs. So in the world of training, IP is king, right? Everybody protects it. We give it, and we're the only company who does it. So when we partner long term, we've got a client that's got about 500 sales reps. We didn't the manager training first, right? Now we're in year two, we're working with the reps, and all along the way, the enablement team is shadowing and train the training with us. So we're passing over the subject matter expertise, but we're also passing soft copies at the curriculum. And that's the thing that nobody does. When a training and enablement team can get the soft copies, they can customize it, they can go roll it out to the other 200 people, they can push it back into new hire, they can build career paths. It will grow with them in their org long term. So when we give them the keys, right, their cost goes down to an annual license fee, and they have all the tools they need to expand the program and let it be part of their DNA. Because what you're training here has to be reflected in your conversational intelligence tool here or in your QA forums there, or in your AI role plays or coaching. And the access to the content sits outside. We prevent that from happening. But it's that integration that helps build, like we talked about, the systems around the new skills to support them and keep them alive.
Bryan SchielkeThat's fantastic.
Lauren BaileyI hope so. I hope I don't look back at this and regret it because nobody else has done it. Maybe that's for a reason. But it's been amazing. The results we're seeing are fantastic.
Bryan SchielkeOh, sounds like it's paying off. So that's great to hear.
Lauren BaileyThank you.
Bryan SchielkeAll right. Let's go. Next question here. You've trained and spoken in more than 30 countries. What is surprisingly universal about great selling and what changes dramatically based on culture or market?
Lauren BaileyReally good. I would say the surprise is um the same mistake that sellers make around the world. And it's, you know, the premature pitching or lack of discovery. And it happens because of a lack of confidence or nerves. We know our product so well. We talked for a minute or two. We're excited someone's actually talking to us. We're like, hey, here it is. And we just sort of, you know, pitch slap people. It happens everywhere, everywhere. Not deep enough discovery so that we're really uncovering values and tying to those. What changes country to country is the rapport dance. When you're working with folks in the UK, oh God, they're so kind.
unknownRight?
Lauren BaileyA rep will get, you know, brushed off or hung up on in the UK. And I was like, that was the nicest person I've heard in a year. And yet they're like, oh, they were pretty rough. So they don't want to be rude to each other. And in Asia, we take a long time before we get down to business. All right. A very long time before we get there. There's a lot of relationship building first. I teach in intros in the US and a lot of Western European countries that we skip the hi, how are you part? It's kind of a rote thing. I was married to a person from the Netherlands my first time around. And he was amazed when he moved to America how many people would ask how he was, but not care to listen to the answer. Little did he know that people thought he was strange when he would answer, like, oh, well, thanks for asking. Here's what's going on with me. They're like, we don't, we don't care, dude. But in France, oh, you wouldn't dare without jumping in and really uh like digging into that. So it's those the dance of rapport and social norms and how those show up in sales is what's the big differentiator.
Bryan SchielkeThat makes sense. Well, thank you for sharing that. That's definitely helpful. Appreciate that. All right. Uh, next question. You have a bold mission of helping at least 50 women get promoted every year. What are the most common and visible barriers you see holding high-performing women back from their first leadership role?
Lauren BaileyOh, buckle up, dude. These are fun. These are easy too. I started Girls Club, which is our program about helping individual contributors and revenue launch into their first management role, right? The goal is more women at the top. And to do that, I fill the pipeline. I can't help it. I'm a sales leader, right? This is my strategy. And so what I've learned through eight years of doing this is that super qualified women are waiting and not raising their hands to get into management because we're not so sure we're going to kill it. And of course we're not sure. We've never done it before, right? HP did a study about this. If there's a job posting, frontline sales manager, and there's 10 things, right? The candidate will. Man applies when he's got about six of them. Hey, I can do this. They'd be lucky to have me. A woman waits until she's sure she can crush all 10.
unknownWow.
Lauren BaileySo it's that perfectionism through line that keeps a woman sitting on her hands instead of raising it. So I had that perspective after training hundreds of managers around the world, mostly men, most of them, did not know what the hell they were doing, right? And I thought, all right, if I can bring some of these skills and insight to women before they get the job, we could get more of them to apply. So we do frontline management skills, we do confidence building, right? To get us to raise those hands and lower perfectionism to raise risk taking because they are mutually exclusive. Then build community. They get a mentor. Anyway, it's the secret sauce, and the women take off like freaking rockets. We're celebrating almost 600 promotions. Some of our first graduates were SDRs when they started, and we have them at the VP, SVP, and C level now.
Bryan SchielkeThat's incredible.
Lauren BaileyYeah, it's super exciting. So the number one invisible barrier on the women's side is feeling as though we have to be able to do the job perfectly before we get the job. And so taking the risk on ourselves and speaking up and volunteering when we don't feel 100% ready, that's the biggest barrier. On the flip side, on the hiring side, the big barrier is thinking, okay, well, right, I don't have enough women applying and I've done all I can. I'll interview all the candidates who raise their hands, and the best person will get the job, right? There's so many amazing male allies that are like, look, if you could get more women to apply, I'd hire them, right? And so what we can do on the hiring side is number one, go and ask the women on our team to apply. That almost every single woman who's in a girls' club and got the promotion told that story. Well, my boss said I should consider management, that he thought he saw something in me. Boom, makes all the difference. The second thing we can do is be careful about that laundry list of what the ideal candidate will have. Not only do long lists preclude women and other diverse groups from applying, right? The list is often written in male or aggressive language. Women don't want to crush quota, right? We're more inclined to want to build customer relationships, which is why women dominate in sales. So you can watch the tonality there and encourage more women to apply and keep the list short to just the requirements. Doesn't mean you aren't looking for other things, but you'll see more women apply that way.
Bryan SchielkeThat makes sense. Wow, that's fantastic. What a great impact. That's huge.
Lauren BaileyOh, it's been so inspiring. I've learned so much from these women. Absolutely. It's a really neat community. And that's what inspired Legacy, which is the brand you saw me showing at the beginning. So many of the amazing women leaders and men leaders who came in to mentor and give back and be thought leaders in the girls' club community shared, damn, I wish I had this coming up. And frankly, I could use it more now. It's lonelier at the top. You know, as an entrepreneur, that can be the case. So Legacy brings together senior executives in corporate and founders in a community that, again, is about supporting each other, showing up with authenticity. It's that room you don't have to prepare to be in, but you can go in with questions and come out with clarity and honest feedback where you can workshop ideas and talk about not just work, right? We we got a session this month about planning on retirement and what's that next chapter? That shift that happens somewhere in our senior career where we're less about chasing the title and the money and more about chasing the significance and the legacy we're leaving behind.
Bryan SchielkeThat makes sense. Well, terrific segue, because we're going to go back to talking about legacy now. Uh, for our next question. You're building legacy executive club around belonging and giving back. What gap did you see in traditional executive networks that made you say, we need something different?
Lauren BaileyWhat a super question. You're great at this, Brian. No wonder your business is so successful. You get to the heart of who people are when you're matching them with your clients, I'm sure, very quickly. I was part of a women's entrepreneur group that the first couple of years fed me in a way of knowledge, but not confidence. Everybody was so busy proving they were successful, right? Their value props were all polished and they presented as just these. I was, I would go back to my hotel room and cry. Let me just tell you that, right? Because my business sucked and I don't know what the hell I was doing. And the third or fourth year, the woman who founded it came to me and said, you know, LB, I think you've got the biggest business here. And what was missing for me was the authenticity. I wanted a place where I could go and say, I'm pretty sure I effed this up. Or I have no idea what I'm doing when it comes to social selling or, you know, all the different things you have to learn as an entrepreneur. And it wasn't a safe space to do that. Everybody was so busy pretending, right? And when I dug into it, I went and did a final session with this group. And I had them, you know, I'm a trainer, so I had to get people out of their seats, but I had them go in the room according to the size of their business and their goals. And nine-tenths of the women there had lifestyle businesses, right? And they were happy if they made 100 grand in a year. And I was trying to scale up to 3 million. So I wanted a place where you could be authentic and transparent and come in messy. But I also wanted a place where we were attracting the givers, right? Like we've all found the energy vampires in our lives and the people who are like super smart and successful, but kind of assholes, right? And this is not their group. And it's when people get into a room with the other legacy members, they're blown away. Because to be in a room with just the lights, it's very different. So it's a place where we get to collect our favorite people, Brian, like clients from 20 years ago, people who used to work for me, their favorite people and their mentors, and they come together to help each other across corporate and founder. You'd be surprised how many of our corporate folks, that's their next chapter.
Bryan SchielkeOh.
Lauren BaileyRight? They want to be you, Brian. Right. And you want them to refer you and help you to build your business to attract leaders like them to buy from you, right?
Bryan SchielkeAbsolutely.
Lauren BaileySo, yeah, there's no handing out of business cards and selling at each other. It's not about that. It's about helping each other. And it's so fulfilled.
Bryan SchielkeLove that. That is fantastic. Well, that that ties in well. Last question here. Summit sessions is all about leadership, business growth, and relationship-driven success. In your world of revenue teams, and quotas, what does relationship-driven selling actually look like in practice when pressure is high and targets are real?
Lauren BaileyYeah, well, we skip that part pretty quickly, don't we? I think that in a lot of ways, in I I specialize in virtual selling. And those are very short conversations. They're phone-based or video-based. There's not an in-person dinner in a 90 minutes before and after the presentation, et cetera, et cetera, right? So we have to learn how to do that fast. And unfortunately, we are teaching the younger generation bad things when it comes to this, right? We teach multi-threading with email, phone, and social, but we don't teach value first relationship first. Now these are just three pitch channels. And I'm I'm not here for it. I was building a class on relationship building and value-based selling and went into my LinkedIn messages looking for one that didn't lead with a pitch. And I went through 300 before I've gone. It's painful. You know it, you get them too, right? So, what does it really look like? Is the art of bringing not personalization but personality. And unfortunately, we give people scripts instead. We hire you because you have a great personality. And then we ask you not to bring it and we hand you a script of what to say. So we've got to teach people to pick up the phone, right? Because teenagers that are entering the workforces aren't really sure that these things dial, right? It's just for texting. We've got to teach them to show a little bit of themselves, be a little vulnerable, share a story, not try to come in, like you said, perfect and glossy. It's not about what you're showing. It's about who you are. And so we have to pull that out of people. And that's how you build up the trust scale. Salespeople naturally start at the bottom, right? About 3% of people trust salespeople. Yeah. Which is higher than politicians. So that's the positive news. But when we're going to build a relationship, we need to move up through the distrust to the conditional, to the, okay, yeah, I conditionally trust this person. This could be good, right? All the way up through a trusted advisor. And we do that by helping people see who we are, share ourselves, share our stories, give advice, be honest, spend more time talking about them than about us, and doing what we say we're going to do consistently.
Bryan SchielkeYeah. It's amazing how much feedback we get on people saying, wow, it's the conversation. Or the discussions are really different because we're not pitching and we're not selling. We're asking questions and we're trying to add value, right? And even if it's not value through us directly, it's a referral or some information or some market data. But, you know, there's always an opportunity to add value to alms to everybody you talk to.
Lauren BaileyAnd salespeople, especially, Brian, because you have a chance to work with leaders in 20 different industries in a given month, I bet, right? Or 20 different companies at least. And most leaders don't. We're kind of siloed in our own companies and or industries. So even if you're just being a honeybee and spreading around a little knowledge about what you're hearing from other places, that's valuable to folks. So I think that that's it, it it's something that's not taught often enough. What people do value and then how to pull that out and be confident in delivering that to them. And that's what we try to teach at right. And it's it's a joy when we find companies and people like you to work with who do that on a daily. And it feels different.
Bryan SchielkeYeah. It's just an easy connection, right? It just it feels natural. Yeah. Yeah. Love that. Should that's fantastic.