Episode 505: Bringing Personality Back to Sales with Lauren Bailey

Brynne Tillman [0:02]: Welcome back to Making Sales Social. I’m Brynne Tillman, and I am so excited for you to meet our guest today. Lauren Bailey is a three-time founder, award-winning keynote speaker, and the driving force behind Factor 8, a sales training company she built over nearly 18 years to help BDRs and AEs hit quota faster and actually stay in sales. She’s also the founder of Girls Club, a movement dedicated to helping women earn their first sales leadership roles, and most recently launched Legacy Executive Club and her new podcast, After the Title, where she’s having unfiltered conversations with executives about what truly matters once you’ve climbed the ladder. Lauren has trained and spoken in over 30 countries, been named a Top 25 Most Influential Inside Sales Professional multiple times, and somehow still manages to give her kids a chore chart with a two-time OTE. We are glad to have you here, Lauren. Welcome to Making Sales Social!

Lauren Bailey [1:05]: Hey, will you write my Christmas card letter? Because that was fantastic.

Brynne Tillman [1:09]: Oh, it’s a combination of me and Claude, so I can’t take all the credit.

Lauren Bailey [1:13]: I did run it. It pulled up some good stuff. Some of that was news to me! I loved it. Thank you.

Brynne Tillman [1:20]: So, side note on this: it’s just a prompt, Claude, and your LinkedIn profile.

Lauren Bailey [1:26]: I didn’t even know that was in there anymore. This is why I need your social sales training. I’m so excited about the upcoming series that we’re going to do.

Brynne Tillman [1:34]: Well, let’s talk about you today, because this is what really matters. Before we jump into your genius—and there’s a ton to jump into—we ask all of our guests the same first question: what does making sales social mean to you?

Lauren Bailey [1:48]: Well, I hope it means making it fun for the buyer and for the seller, right? This is the hardest profession out there. It is nothing but failure, failure, failure, failure, win. It’s like golf, right? When we make it social, obviously that’s a strategy so that we are multi-channel threading and selling. But I think that in every interaction, we can and should be making sales social. That’s most important for leaders because we go out and hire salespeople based on their personalities, and then we do everything we can to strip them bare of it and hand them scripts instead. That pisses me off. So, let’s bring personality back.

Brynne Tillman [2:34]: Oh, I love that. People buy from people, not from scripts.

Lauren Bailey [2:37]: Or from AI bots, or from profiles, or texts, or anything else, right? We’re so afraid to just get real with people, pick up the phone, and share ourselves, but those are the natural abilities that sellers bring. I imagine you’re constantly doing the same and coaching people to bring their personality to their profiles and to their messages. It’s just even more important when it goes from what you teach to what we teach and picking up the phone.

Brynne Tillman [3:05]: Yeah, I love that. You know, I love all the technology and all the AI—I love all that stuff.

Lauren Bailey [3:12]: You’re amazing at it.

Brynne Tillman [3:13]: But the human side of it is still the most important when it comes to business development, sales, and all those fun things.

Lauren Bailey [3:20]: And Brynne, do you agree that it will become even more important in the coming years?

Brynne Tillman [3:26]: Yeah, the more AI becomes AI, the more human will matter.

Lauren Bailey [3:32]: The more human will matter. I love it. I’m starting to get early calls from sales leaders who are getting that. They realize that table stakes is the automation, the scale, the creation, and the AI. They recognize their team and their reps will be the differentiator, and they want to invest in them. I just want to stand up and applaud.

Brynne Tillman [3:54]: Yeah, I love that. It’s interesting, I have fun when I call in and there’s an AI bot there because I play with it. I think it’s fun. But one of the things that frustrates me with AI is engineered empathy. Don’t pretend to care about me; you’re a machine. It’s just frustrating. I prefer to hit 0-0-0 because I want a human being anyway.

Lauren Bailey [4:22]: We all do, right? We all do. I like the idea of automating some of the simple things, but there has to be a path to a human. Look at half of our banks and credit cards and that industry; first they offshored and pissed us all off, and now they’ve over-automated. You can’t get to a human, and when you do, you wait forever and they’re horribly trained. It’s like this industry that so many people have just given up on because it’s too frustrating. So, let’s be careful with automation and cost savings, and balance that in key moments with personalization, social connection, and personality.

Brynne Tillman [5:02]: Yeah, I love it. We’re often saying that while everyone talks about work-life balance, we’re talking about AI-human balance.

Lauren Bailey [5:08]: We are, and “engineered empathy” is something I have to remember. That’s fantastic.

Brynne Tillman [5:12]: Thanks, I love that one. Alright, well, I’m really excited to talk about some of these amazing accomplishments you’ve achieved, but in a way that’s going to help our audience learn a little bit. I know you’ve spent nearly two decades helping sales reps ramp up faster and stay longer—turnover reduction is a huge thing. What’s the most common thing companies get wrong in the first 90 days of onboarding that quietly kills a rep’s confidence before they even get started?

Lauren Bailey [5:45]: Oh, the list in my head is growing. It’s like when you have to scroll up when ChatGPT is giving you answers, right? Which, by the way, could we just make those windows wider so I don’t have to scroll as far?

Brynne Tillman [5:58]: Please! Yes, right? Agreed.

Lauren Bailey [6:01]: All right. I figure, Brynn, with as good as you are at all of this, you have the connection somewhere to make that happen for me, so I’m just planting the seed. Listen, mistake number one: I used to audit new hire training programs because this was my “whale”—the Moby Dick thing—when I was in corporate America doing new hire training to launch call centers with IBM and SAP around the world. Nine out of 10 programs focus heavily on our product and our systems, and they leave out other critical areas like sales skills and process. Think Schoolhouse Rock!—how does a bill become a law in our company? What are the top 10 questions a customer is going to ask? How do you get things done here? Answering those builds confidence and speed to ramp, which is the whole goal. Then, the other thing we have to look at is acumen: industry acumen, customer acumen, and business acumen. Programs are grossly lacking there, and AI actually helps the most in that area. Finally, the bonus points come from the involvement and integration of the managers. When we don’t do that, we find that we either grossly under-train—meaning a rep understands the product, but the moment they actually talk to someone, they just throw up speeds and feeds all over them because it’s all they know—or we do the opposite and keep them in classroom training for six to eight weeks, falsely thinking they’re actually going to retain all that information. A well-balanced and synthesized program mixes each of these five to six categories daily and weekly for somewhere around two to three weeks, including live calling during this time. I call this “just-in-time training.” Think of new hire onboarding as preparation for their first one to two months on the job, and remember that training is not something you did, it’s something you do. New hire training gets them ready to leave voicemails, update CRMs, and do basic introductions. They’re not going to be negotiating a complex sale in their first two months, so why train it yet? They’re not going to overcome tough competition in the first two months, so don’t bring it up. The goal of onboarding is to keep that rep in their seat, and that means building their confidence and competence so they’re excited to get out and crush it. It’s actually better off that they don’t know what they don’t know yet, otherwise, you’re scaring the crap out of them because there’s no way to master it all at once. It’s overwhelming. Keep it short, keep it small, and build mastery and confidence in a couple of critical skills that they will face in their first few weeks on the job. Then, structure your programs so that you’re bringing them back a couple of times a week for an hour or two. Training isn’t once-and-done; it should follow a down-ramp that never totally stops, where time on the job and training complement each other.

Brynne Tillman [9:07]: I love that. You give them just enough information to implement, and then—

Lauren Bailey [9:13]: They’re like, “I got this! I can do the first 30 seconds of a call like a boss!” And then here’s the other bonus: once they get past that and they’ve had 20 or 30 conversations, they can’t wait to get back into training to hear how to do discovery better and bridge to the next call.

Brynne Tillman [9:30]: They are ready for what’s next.

Lauren Bailey [9:32]: They’re ready and eager instead of being a trapped, forced participant or trying to figure it out completely on their own.

Brynne Tillman [9:40]: Oh my god, I love this! And that’s only question number one, Lauren!

Lauren Bailey [9:45]: But let’s integrate what you do into this, right? Because we know that multi-threaded selling across channels is really important. It’s not just the first outbound call; it’s the connection request, the engagement on posts, and maybe message one.

Brynne Tillman [10:03]: What kind of value do you bring before you ever have an ask?

Lauren Bailey [10:06]: Exactly. When we don’t train reps on what to do in that initial outreach—be it on social, email, or voice—what do they do? They billboard. They become walking billboards. It turns into too expensive of an investment, and it’s no fun for the customer, meaning it’s no fun for the rep.

Brynne Tillman [10:29]: Amazing. Alright, I want to jump a little into Factor 8 and how you are laser-focused on virtual selling. You were doing this long before the world was forced into it.

Lauren Bailey [10:41]: We did inside sales before it was cool, right? Before it was mandated. What I saw early on that most sales leaders were ignoring was what it actually takes to effectively sell through the screen. This is exactly why I built the company; I was an enablement leader and a sales leader looking for this curriculum in the market. You see all the usual suspects in the big training houses, but the big difference—which still exists today—is that they are training what to do in a face-to-face conversation. That covers 90% of the sales books you see out there. But Brynn, you and I know that the hardest part of selling is getting that conversation in the first place. They were ignoring that complete front end: How do I outbound? How often? What do I say? Do I leave a voicemail? How do I start the call? Do I send an email? What does the cadence look like? What’s the outreach? Big companies will try to shoehorn things in, saying, “Hey, we bought this curriculum, let’s just apply it to the inside team too.” It’s a huge turnoff and it just doesn’t work because these require special skills. For example, when we taught elevator pitches way back when to field reps who were packing a bag and getting on a plane, we were talking about what to do in person where you have the time of an elevator ride. We take these value propositions that marketing creates and give them to our sellers, but a prospect hangs up the phone before the rep even starts sentence two. It doesn’t work. The timeframes are shorter online; a successful initial call might only be three minutes long. If I read the value proposition marketing gave me, that takes up all three minutes!

Brynne Tillman [12:36]: Right! And it’s all about me, right? “This is how we help companies just like you.” The conversation is all about what I want you to know, but not around what you actually care about knowing.

Lauren Bailey [12:50]: Bingo. That’s our most famous module, called the SWIFT intro. SWIFT stands for: So, What’s In It For Them? We weave it through everything. It also serves as a reminder to speed the hell up—be swift. It’s a quick, 10-second or less introduction that perks their ear with immediate value regarding what’s in it for them, and then it ends with a very specific kind of question. The goal of the introduction is to get the customer talking. That’s another big misconception; the goal is not to earn the right or establish credibility upfront. The goal of an intro is simply to stay on the phone, and the only way you’ll do that is if you get them talking.

Brynne Tillman [13:36]: I hate to put you on the spot, but can you give us an example of what that might look like?

Lauren Bailey [13:44]: Yeah, absolutely. “This is LB calling with Factor 8. I’m calling to see if I can make the ramp time for your team a little bit shorter this year. Are you running AE teams or BDR teams?”

Brynne Tillman [13:56]: Oh, I love that. That’s awesome!

Lauren Bailey [13:59]: It’s quick and easy. There’s actually a scientific brain hack that goes into that called instinctive elaboration. It means that when I ask you a question, the human brain is literally proven to stop what it’s doing and start answering it. For example, listeners, right now: how old are you? The number immediately appeared in your mind.

Brynne Tillman [14:19]: Yes! Well, I think I was off for a second, I forget, but yeah.

Lauren Bailey [14:22]: I know! By the time this airs, I’ll be another year older. But the point is, it means the answer is already halfway out your mouth. What that also means is you are no longer processing the email you were reading when you accidentally answered the phone. If we can get them to turn in and answer that question, it breaks the distraction—but it doesn’t work with your typical open-ended sales questions. Nine out of 10 times, we’re training reps to do deep discovery and ask open-ended, value-based questions. All of that is great, but none of it belongs in the introduction. The intro requires a closed, easy, rote-answer question.

Brynne Tillman [14:59]: I love that it’s closed. You give them a clear choice: BDRs or AEs? It’s so easy for me to answer. Once I do, you’ve successfully established a real conversation, even if it started with just one word.

Lauren Bailey [15:16]: Here we are, we’re in a conversation. As a bonus, you’re usually getting your qualification questions out of the way early on. When you’re conversational, fun, and interesting, you can get three or four questions answered before they pause and think, “Wait a minute, what did I just do? I’m in a sales call. Who are you with again?” That is the exact moment you land your value proposition, because now they are actually listening. But when you start right out of the gate with, “Hey, I’m Lauren, and I’m the world’s leading provider of inside sales training,” it just screams “sales call, get me off this phone.”

Brynne Tillman [15:52]: I love that. You’re starting with a challenge that a qualified prospect is actively feeling. You’re entering the conversation to help them solve a problem about them, not just to sell a product.

Lauren Bailey [16:08]: Yes. I actually have a hilarious keynote reel of all the intros we hear, like, “I’m calling to introduce myself as your new account manager.” It’s like, well, good for you, only your mother cares! It’s not our fault as sellers; it’s our fault as leaders because if we don’t train them to do it better, reps just pull scripts out of thin air. Those introductory skills are incredibly important, even for established sellers.

Brynne Tillman [16:50]: Yeah. We have a saying: stop telling them how you can help them, and start actually helping them.

Lauren Bailey [17:00]: Yeah, and the way I translate that is by delivering little nuggets of value during the conversation. Funny story: Factor 8 actually stands for the translation that happens between your product and the customer. I kept drawing this graph on the board while naming my company, representing the ability to translate technical features into customer value. Every time we teach a sales theory, my trainers’ job is to translate that theory into something highly tactical—not just the what and the why, but the how and the when. If you want to focus on helping them, offer a free nugget, a resource, or a benchmark. One of the greatest inherent values of sellers is that we act like honeybees. I talk to a thousand sales leaders in a year, whereas most of them only talk to one or two peers. Because of that, we get to cross-pollinate ideas: What’s happening out there in the industry? What are we noticing in the market? What are some things that might help them? Drop a little tip along the way.

Brynne Tillman [18:06]: So great. Speaking of helping, tell me about Girls Club and how you’ve helped thousands of women move into their first sales or sales management roles.

Lauren Bailey [18:20]: Thank you. The goal of Girls Club is filling the pipeline with future female leaders; we have to reverse the negative growth trends. I’m so sick of being the only woman at the table, in the room, or on the stage. About eight years ago, I realized I could help solve this because, like a honeybee, I had the privilege of training thousands of managers around the world. Most were men, and I saw all these incredibly capable female reps simply not applying for management tracks. As women, we tend to be perfectionists; it’s rooted in brain science. We often don’t want to apply for a role until we know we can check every single box perfectly, so we take fewer risks. Girls Club was designed to find women before they were actively thinking about moving into management to prepare them to raise their hands sooner and more often. It’s a combination of the management skills we train at Fortune 500 companies alongside confidence building, mentoring, and community. I just had a call prior to this with women who were coming back to advise the next generation, which we do every year. The stories they tell, the positions they hold today, and the love they carry for the community they met in this program are incredible. A graduate named Jess literally said this on our call, and I wrote it down: “Girls Club is like an oxygen mask for me, and I want all women to feel that support.” It gives me chills. People who graduated from our first cohort are at the C-level now. It completely holds my heart. We run a cohort every year. This is the first year we’re launching a 201-level course and making it co-ed, because our current administration focuses heavily on equal opportunity for all. Girls Club 101 will stay focused on that first-time move into management at the beginning of every year with a cohort of about 50 women. Then in July, we’re launching 201 for existing managers who want to keep moving their careers up, and we’re welcoming men into that program as well.

Brynne Tillman [20:42]: Wow. When you say administration, do you mean a board running the program?

Lauren Bailey [20:45]: No, I mean government compliance and administration. We actually lost clients because of the name of our program and the requirement that development opportunities be open to everyone equally. Organizations could not formally support a program restricted by gender; corporate DEI initiatives have shifted. So, we actually have a really cool, brave man in this year’s cohort of Girls Club. I love that someone is willing to join something heavily branded in pink; I just think that’s awesome, and he’s a total stud. But we’re leaning into equal opportunity. What we’re doing is magic, so let’s open it up for all current revenue managers looking to up-level their careers. I love keeping our groups majority female because in top leadership roles, if you don’t intentionally set a goal—like maintaining 60% or more women—it quickly defaults back to a traditional boy’s club simply because there are more men in revenue roles at the top.

Brynne Tillman [21:51]: Which was the whole point of starting Girls Club to begin with.

Lauren Bailey [21:53]: Exactly. We’re going to keep the heart of it alive while expanding the programming and the reach. I’m just thrilled—I think we’re close to counting 700 promotions now.

Brynne Tillman [22:04]: That’s amazing. I’m thrilled to hear you’re making that kind of impact. Tell me a bit about your new podcast, After the Title. It explores what leadership looks like after a leader meets their metrics and hits the peak of their career.

Lauren Bailey [22:24]: You’re exactly right. The podcast is tied directly to our Legacy Executive Club. When we started, we had amazing executive women come in to act as role models for Girls Club. I reached out to women I deeply admired in my career but used to be nervous around—like Judy Buchholz, head of sales at IBM—and asked them to speak. As I got to know these women over the years, they shared with me that they wished they had a similar community, noting that it was frankly much lonelier at the top than it was coming up. We started creating informal groups of high-achieving women, which great men eventually joined too. The conversations invariably went in the direction of: “Once I reached my goal—whether it was President, GM, CEO, or VP—I realized I started defining success differently.” It’s no longer as much about the title, and it’s certainly not as much about the money. What becomes most meaningful is the impact you’re having and the careers you’ve shepherded. The conversation keeps spinning until you land on the word legacy. The podcast focuses on what truly matters, how that differs for all of us, and how we integrate that into our lives. There is a certain level of corporate brainwashing that happens as we climb the ladder. Brynn, you and I broke out to start our own things so we don’t see it as acutely, but I bet you see it with your clients and friends. It’s the mindset of: “Of course I’m working 60 hours a week and sacrificing my family, my health, and my personal life to chase this title.” But it comes to a point where you finally achieve it, you look at what you’ve given up, and you want to chart the next chapter with a little more intention. Those are the conversations we’re having.

Brynne Tillman [24:26]: I love that. That brings me to our mutual friend, Viveka von Rosen, who really champions this exact transition. I love what you’re doing and how well it bridges to her work.

Lauren Bailey [24:46]: Well, she specializes in helping women chart those exact chapters through deep coaching and retreats, and I’m just grateful to have her time and brilliance involved in Legacy. She facilitates our monthly personal board cohorts of peers. What’s great about the magic Viveka brings to these conversations is that while 50% to 60% of the discussion focuses on core business strategy—like go-to-market plans, using AI, and benchmarking—it’s the other 40% to 50% that I love the most. For example, a member shared that her husband’s personal board advised him to get an optional cardiac calcium test, which most people don’t know about, and it literally saved his life. We’re talking about the other critical parts of our lives: our health, our families, our dreams, what retirement will look like, and the long-term impact we want to have. That’s where the real magic is, and it multiplies when you share it with other brilliant people operating at your level. I have 10 amazing, really cool ladies living in my neighborhood who are my age, and none of them have corporate careers. They look great in their yoga pants, to be clear! But I can’t go to them with this specific corporate stuff. If I want to workshop what’s meaningful at this stage of life, I want to do it with you, Viveka, and Judy Buchholz, and learn from them. I’m enjoying it immensely.

Brynne Tillman [26:31]: Yeah, a high tide rises all boats for sure.

Lauren Bailey [26:34]: It really is key. As I’ve gotten older, Brynn, I’ve broken up with toxic people and said no to working with “SaaS-holes.”

Brynne Tillman [26:49]: That’s my new favorite line! Oh god, I love that!

Lauren Bailey [26:52]: We all know one or two! Other things become far more important, and I’ve realized how much joy is tied up in who we choose to surround ourselves with. As a working woman and a mom, I put so much of my soul into raising my companies and my children that when I hit 50, I looked around and realized I only had two close friends left. That was a wake-up call. I needed to do better.

Brynne Tillman [27:20]: Interesting. I’m very fortunate to have a few very close personal friends, but I also have a lot of wonderful friends in business. A lot of that comes from where I originally met you, which was Women’s Sales Pros—now rebranded as Women’s Sales Experts. That’s been an incredible opportunity to meet brilliant, like-minded people with whom I completely align.

Lauren Bailey [27:51]: That’s the key: you have to find your tribe. Legacy and Girls Club wouldn’t even exist had I not been part of that community. Being shown the way by role models like Trish Bertuzzi—who was my total idol when I first showed up—made all the difference.

Brynne Tillman [28:05]: And Jill Konrath, Lori Richardson…

Lauren Bailey [28:11]: Yes! They came in and openly shared their playbooks. I remember saying, “Trish, I know I’m a tiny company, but you know I’m technically a competitor.” And she didn’t care; she just wanted to help.

Brynne Tillman [28:22]: You are definitely not a tiny company, my friend.

Lauren Bailey [28:24]: Not anymore! But I was then, and I was nervous just to be in the same room with those women. They shared and they helped, and it was the first time I had experienced that environment. Usually, being the only woman in the room within a corporation, you encounter a completely different dynamic. Let’s be honest, there were other women in my past corporate lives who were not supportive at all because the culture was cutthroat. I think we’re doing better now as an industry.

Brynne Tillman [28:46]: Yeah, what I love about Women’s Sales Experts is that everyone is genuinely there to make things better for one another. It’s entirely about elevating each other. It’s wonderful because it’s historically been hard to find women in sales leadership. It makes me a little sad that Girls Club has to evolve its structure, but I know it will still bring tons of value. It’s amazing to be around peers who understand our unique corporate journey. Most men will never experience what we experienced coming up through traditional corporate sales infrastructure; it’s just a different reality. I’m not saying it’s inherently harder or easier, but—

Lauren Bailey [29:33]: I will straight up tell you it’s harder. I will die on that hill. It was harder because of the lack of representation, role models, and systemic relationships. One of my favorite milestones with Girls Club involved the VP of Sales who made my life a living hell when I was a sales manager. I had joined his “boys’ club” and disrupted it, and he was not happy about being told he had to hire me. I was the most miserable I’ve ever been in my life working under him. Fast forward 20 years, and he became my very first corporate sponsor for Girls Club. He had daughters, felt a little retrospective guilt, and reached out. I told him, “Let’s do better than just throwing money at this, Rob. Why don’t you join me for a fireside chat called The Unintentional Boys’ Club?” I asked him straight-up questions: Why is it that leadership teams only seem to hire men? How does that happen natively? Do you treat female leaders differently? Do you talk about us when we’re not in the room? I was so impressed by his vulnerability. He is a lovely human being, and his honest answers were surprising. He admitted, “Yeah, we do treat you differently, because I can aggressively lay into the rest of my male managers, but my absolute biggest fear is making a woman cry at work.” And the flip side of that is that almost every woman in corporate life has experienced that exact moment where they are holding back tears because of how we process stress differently. Men also generally haven’t experienced the discomfort of being inappropriately hit on at a company happy hour.

Brynne Tillman [31:11]: And if they were, they probably saw it as a pure compliment!

Lauren Bailey [31:14]: Right! In nine years of running Girls Club, we do an anonymous straw poll every year asking the percentage of women who have been inappropriately targeted at a company happy hour. Do you want to take a guess at the result? It is 100%. Every single year. So, the experience is just fundamentally different. But when women work together and actively support each other, everything becomes easier; there is massive power in that.

Brynne Tillman [31:38]: I love this.

Lauren Bailey [31:39]: The most important thing to remember is that we don’t make men the enemy. There are so many incredible men on our calls who mentor, advocate, and do fantastic work.

Brynne Tillman [31:49]: They are also being educated by listening to what women have to say as a united front, rather than viewing it as an isolated incident.

Lauren Bailey [31:59]: Exactly. Every time I keynote about what women want at work and we have these open conversations about structural differences, the line of people waiting to speak with me afterward is entirely composed of men. They say, “Oh my god, I genuinely didn’t know. What else can I do to support my team?”

Brynne Tillman [32:18]: You are creating allies!

Lauren Bailey [32:21]: We do formal ally training every single year. It’s super cool and rewarding.

Brynne Tillman [32:25]: I am so excited about the impact you’re making. To really hear the scope of it gives me literal chills.

Lauren Bailey [32:38]: The impact these women go out and make afterward is what is truly inspiring. They always come back to mentor, pay it forward, and speak. They mentor within their own organizations, hire more women, and give them real opportunities. The next frontier for me before I eventually retire is making a real dent in the wage gap. Women still earn roughly 81 cents to the dollar compared to men, and as women, we own a piece of solving that through negotiation. It requires asking, “Can you do better on this offer?” instead of just feeling grateful to receive it. Men will frequently negotiate three rounds or ask for off-cycle raises, whereas many women don’t speak up once. But it’s also on us as leaders. I would be willing to bet that every sales leader listening to this has inherited some form of pay inequity within their team and is completely unaware of it. We have to actively check the data.

Brynne Tillman [33:46]: Such great insight. You are so inspiring and fabulous, and I’m so glad I got to tap into your genius today. I know there’s so much more to cover, so we might have to do a part two. As we start to wrap up, is there a question I should have asked you that I didn’t?

Lauren Bailey [34:06]: You know, we started talking about core selling and then I got a little too comfortable on my soapbox about the power of women in sales! I think the question we should tackle together to bring it home is: what is one thing all sales leaders can do to make sales more social, more fun, and more successful?

Brynne Tillman [34:32]: I love that. Let’s do it: what is one thing sales leaders can do to make sales more fun, social, and successful?

Lauren Bailey [34:41]: Because all three of those pieces go together, my answer is: celebrate small wins. I would say 50% of the organizations we work with have a great scorecard tracking KPIs and core metrics, and the ones that have it dialed in manage to those metrics like crazy. But there are probably 10 critical micro-opportunities that happen before a Stage 2 conversion ever shows up at the top of your scorecard. To celebrate a small win early on during confidence building, change the questions you ask your team. Instead of asking, “Tell me how many meetings you booked today,” switch it to say, “Tell me about the most interesting conversation you had today.”

Brynne Tillman [35:30]: Oh, I love that!

Lauren Bailey [35:32]: Look at how that simple shift changes the team dynamic. Focus on, “Tell me what you learned about the customer’s industry today,” or “What did you learn about their macro challenges this week?” Count those insights as foundational wins because it forces the rep to focus entirely on the customer. It’s a critical baby step. When a rep gets to the end of the day and can tell their manager, “I had the coolest conversation today,” you are actively rewarding the right behavioral inputs.

Brynne Tillman [36:02]: And when a rep knows that specific question is coming at the end of the day, they spend their hours actively working to have cooler conversations.

Lauren Bailey [36:07]: It stays top-of-mind. Reps know exactly what is important based on where their leaders spend time and what they talk about. The downside of virtual selling in metrics-driven environments is that, like baseball, we can measure absolutely everything, so we fall into the trap of only talking about bottom-line results. Let’s not forget the customer, the conversation, the learning, and the personal growth along the way, because those are the baby wins we need to celebrate. You can even celebrate horrible calls and create a team library of complete failures—and put your own mistakes into it! If we are all hiding from failure, we are sticking our heads in the sand regarding 90% of our actual sales day. Reps come into isolated remote environments thinking, “Oh, it must just be me. I’m the only one struggling with this or getting hung up on,” and that is a massive confidence killer.

Brynne Tillman [37:01]: Oh my gosh, I could not count the mic-drop moments in our time together today. I love that. To wrap things up, I didn’t even realize I was doing a version of what you just described with my own family. My boys are 23 now—they’re wonderful young men—but growing up, they were not natural talkers. At the dinner table, they both had to answer three specific questions every night: What was the best thing that happened to you today? What was the worst thing? And what was the kindest thing you did?

Lauren Bailey [37:31]: Oh, that gives me chills. My family’s third question is always, “What did you learn?”, but I am absolutely adding the kindness bomb into rotation. You are raising beautiful humans, Brynn. I love that.

Brynne Tillman [37:40]: My oldest has a serious girlfriend now, and she actually thanked me for it!

Lauren Bailey [37:48]: I didn’t even know I had that milestones to look forward to! Mine are still teenagers. Yes, they still have chore charts with performance multipliers—this is how saleswomen parent! But I’m actually meeting his girlfriend for the first time tonight, so I’m a little anxious.

Brynne Tillman [38:04]: My absolute advice to you: as long as she makes him happy and is kind to him, you love her unconditionally. Nothing else matters.

Lauren Bailey [38:12]: Brilliant. I promise to do so. Thank you for that advice. We covered a lot of ground today.

Brynne Tillman [38:35]: I know! This was honestly the most fun thing I did all week. This was amazing.

Lauren Bailey [38:45]: I’m so happy to hear that. I can’t wait to come to your training next week. Thank you.

Brynne Tillman [38:50]: I’m so excited to have you there. Thank you so much. For all of our listeners out there, how can they get ahold of you?

Lauren Bailey [38:57]: Find me on LinkedIn under Lauren Bailey. Factor8.com is where you’ll find our core training, and for executives who are intrigued by entering a new professional peer room, check out legacy.vip.

Brynne Tillman [39:08]: I love that. And guys, when you’re out and about, don’t forget to make your sales social!

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