Christina Brady: The Power of Empathy and AIs Impact on Enablement

Every day that you go by and you cannot measure proficiency, then you cannot lead to mastery. And every decision that you make is going to be a guess. It might work out for you. It might not work out for you. Good luck defending that at your next board meeting. Hey, everyone. Welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I think make a positive impact on the world around us. Today's conversation is with Christina Brady. She's the CEO and founder of Luster.ai, an AI coaching platform that helps GTM teams polish and shine through practice. She's also a former artist, musician, and improv performer, which is super cool.

And she has a genuine passion for building culture, coaching and developing leaders, and producing top performing sales and CS teams across small to enterprise organizations. So if you've been following me for a while now, you know that I think one of the areas that AI is going to have the biggest positive impact on sales is when it comes to frontline coaching. Managers don't get trained to coach, nor do they have time to. And when they do, it's typically subjective at best and rarely addresses the root cause of the problem. And Christina has been seeing this play out on the front lines for years, and it's what drove her to start Luster. And so we talked about the challenges with coaching and why it's so important to use a data-driven approach so that subjectivity is not as bad and you can be objective with this, but also have a people-first mentality and why empathy is a true superpower that AI is never going to replace.

We also talked about what mastery looks like and what you need to achieve it along with what we as sales professionals need to be trained on moving forward in this world of AI. So if you're wondering where the future of sales, coaching, and enablement is headed, you're going to love this conversation. Let's make it happen. Christina Brady, welcome to the Make It Happen Monday podcast, my friend. How are you? I am doing so good. I'm so excited to be talking to you. You're a magnificent individual, and I feel like we have so many things that we can just dive into and mutually feel the pain, but then also solve the pain, we hope. Yeah. I mean, that's kind of part of the, you know, hopefully some of that comes out of these conversations, right?

We're not just interesting ones, but we're trying to address some of the big issues that I think, to your point, like we're both seeing out there right now, specifically in sales and specifically in enablement right now. But, Christina, before we get to that, always love to know your origin story and not just the stuff that we find on LinkedIn, right? Because you got a really interesting background from a career standpoint and have done some really cool shit. But talk to us about like, where'd Christina come from? Growing up, family, like where'd you get now that you're a CEO, right? Like, where'd you get that bug? You know, was it nature, nurture, and help me understand a little bit more where you're coming from, and then we'll dive into the topics here.

Cool? Oh my gosh, I love it. If you, if you looked at my family that I came from, you would not have been like, you know what? I bet it's going to come out of that. Arrangement is a CEO, a tech CEO. You would, there's no way. My, uh, I am, I am one of four siblings. I'm the middle child. And like, very obviously you have a five second conversation thing. You're like, this girl's, she's a middle child. She's just screaming for somebody to be like, does anybody know that I'm even here? Like, this is a very difficult. My wife is the exact same way. She's the loudest out of all three of them. And there's no question she's a middle child. And nobody listened. Yeah. Or it's just kind of like, hello, I'm playing with fire.

Does anybody care? Like, I guess I'm just, yeah, we're all feral, all of us, because it's just kind of a part of it. And so, uh, and then I have a younger half brother as well. So, um, uh, my parents were musicians growing up. So my mom was the pianist of the Chicago symphony orchestra. And my dad was, was actually a world renowned opera singer. Um, yeah. So I grew up immersed in the arts and not realizing until I was an adult, how insanely cool that was, but also how much it shaped my brain. Um, musicians are typically really wonderful at things like mathematics and arts and problem solving and communication. It just develops that part of the brain very early. So when I was two and my mom plopped me down in front of a piano and started teaching me music theory, it really kind of stuck with and developed how, how I look and think.

And so I was always an artist. I even majored in college in theater and film acting. Um, I did some musical theater stuff. I was an improv performer for 12 years. Um, and now I do tech stuff. I did tech stuff intermixed in there as well, but, uh, I definitely came from a very, very artistic family. I love that. I, I, I have a similar, like, so my mom was an artist. She, she taught art for her master's, uh, art therapy and such. And so I kind of thought I was going to be an artist going into college. Right. And then I realized very quickly, I'm like, Ooh, um, nope. Yeah. I'm not that good. And, uh, I can't make any money doing this. So nevermind. But my dad was the engineer and funny you bring up like how artists are very, you know, in a lot of ways, really good at mathematics, you know, mathematics and stuff like that.

So he was, uh, uh, an engineer, um, uh, let's see, no, uh, electrical engineer, but played the saxophone in front of thousands of people, you know, solo artists type of thing. So that balance of like art and science, I think is a really good one and a unique one that we can dive into here a little bit as, especially as it relates to training, but now walk us through those careers, right? So you did improv for a while, but you've also had a lot of different sales roles and in different types of companies. So walk us through that too. Cause I think that's going to give us some more context here on this conversation. Yeah. At the same time that I was doing improv performing at IO Chicago and second city, I was also having to, to pay my bills and reality is the arts, unless you make it really big, you know, it's, it's difficult to make the kind of living that I wanted or needed to make.

And so I, I got my first job as, you know, what you would call an AE about 17 years ago. I was a, I was a insurance agent. I was fully licensed. I was able to be a financial planner for, you insurance folks out there. I have my life health auto six, 63, 22, seven, all of which I just gave everybody. If anybody is a listener who sells insurance, I just gave everybody a panic attack. You're welcome. Um, so, uh, I did that and I realized that I was really good at, at selling, but I didn't feel great about what I was selling. And that was a commission only position as so many, I don't know what they are today, but back then it was, it's commission only. There's no base salary. And so taking time off was filled with anxiety and you are constantly, unless you are a fiduciary and forced to do what is best for your customer, you're consistently looking at your policy and what you're selling based on what's going to give you the biggest commission.

And I hated that misalignment with the people that I was trying to help. Um, when I would think to myself, this is actually probably the best policy for you, but I make 50% less if I sell you that one. And so if I sell you this one, it's probably okay too. I didn't want to do that. It's terrible. You know, and I'm young, right? I'm 21, 22. And, and I was like, this, this just feels so outside of me. Um, and at that time groupon was just starting to ramp up in Chicago and it was kind of the cool hit job. I didn't realize at the time that I was going to be breaking into tech. Um, but I wound up getting an interview there. Um, I had a friend who worked there and was like, you, you sell insurance.

It's the same thing. Come, come sell coupons. I was like, I can sell coupons. Like I would love that. Um, so I go there and it was a group interview. I don't know if you remember those or if anybody still does them. I've done one, but it was to get on the apprentice early days before Donald Trump went sideways. Like when, like it was like the apprentice three, I got to the final round of apprentice to be on the show and it was a group and it was a group interview. So that was my only experience with a group interview. Oh my God. Unhinged. Like it was, it was unhinged. There were, there were probably 30 of us in the room and they were just asking questions and you had to raise your hand really fast.

And if they called on you and you had the right answer, they were like, you move to the next round, which is where you had the honor of sitting in front of the VP of sales and you had five minutes to sort of sell yourself. Um, and I think the only way that I got through this was one, my comedy brain, it always chips in where I just sat back and I was like, this is ridiculous. This is the funniest shit that I've ever sat and been a part of. Like, I can't believe this is a, this is how people get jobs. This is what you do. And I think that just that attitude somehow carried me. And so I wound up getting, um, I started off as an account executive full cycle, a group on before there were BDRs before there were so all of that.

And this would have been 2000, 2009, 2010. Um, and I worked my way up from account executive to frontline leader to second line leader at Groupon over the course of about a half a decade. I was there when they went IPO. Uh, and then I was pulled over to Glassdoor to be the starting leader in what was going to become their Chicago headquarter. And so I was leading the growth team at Glassdoor, but then also spinning up the Chicago office. And so growing that office was from the initial 15 people to over 400 people and getting into, um, a senior director position there. Then going over to sales assembly where I was the chief strategy officer. I was building out the programming. I helped them go virtual.

I was an advisor to the portfolio companies. Um, and then I popped over to spec it where I was SVP of sales there for a year before jumping over and what no one saw coming being a CEO of a venture backed AI tech company. Like you look at the, like she's, she's doing what, you know, it's so again, like, like, like Christina who consistently until age, like embarrassingly, like maybe 17 consistently wore glitter somewhere. Um, and I still do. Right. Like, you know, it's funny that my company's name is Lusker because I had to bring that sparkle in somewhere, but certainly not what you would have looked at on paper. I'm like, you know what I bet she's going to do. I bet, I bet she's going to be a CEO in tech.

I feel like that's what she's wouldn't have seen it coming. Hey, I hope you're enjoying the conversation so far. I want to take a quick minute to share with you what I'm working on these days with my new JB sales membership. It includes live monthly training delivered by me on my two signature courses, which are filling the funnel and driving a close to cover all aspects of the sales process. It also includes monthly workshops that'll be running on specific sales skills and different tech skills like ChatGPT and how to leverage AI throughout the entire sales process. Finally, the membership gives you access to my entire online catalog with every course and every tip I've ever done. And as an exclusive offer to my podcast listeners, if you go to jbarrows.com, click on the individual membership link and use coupon code podcast at checkout, you'll get 25% off.

Now let's get back to the conversation. No, I think that's, and I love the journey, right? Sales is always a sales and entrepreneurship and that type of stuff is always just such an interesting journey. There's no defined path for it. Everybody's, well, how do you become? I don't know. You just keep fucking doing shit. You know, you just keep going forward and trying things out and failing miserably and then getting back up and trying it again until you kind of find something that clicks. Right, right. Exactly. So with what you're doing now, where'd you get the bug for, I mean, so the sales bug was there and I think it sounds like you, you realized early on that you couldn't sell something you didn't believe in, right?

Which is fantastic. And so then you got into, you know, the Groupon's like, okay, that's cool. Glassdoor, I could see that connection. Sales assembly, I could absolutely see that connection. Where did enablement or kind of training click in for you just saying, ooh, wait a minute. Instead of me going out there and, you know, carrying a bag and commissions and closing business, I want to help sales reps do it more effectively. Where'd you get that itch? It actually started at Groupon. So Groupon was one of the first companies that hired enablement and one of the first people that they hired, his name was Alex Zakakis. He's at Seismic now, I believe. He and I, our paths have crossed a few times.

And I remember his role was brought in and prior to having enablement, it was, we were responsible for all of that. We were responsible for training and coaching and curriculum. It was all on the managers. And they brought in enablement and there's this idea of like his entire job was to listen to what was wrong and be very, very prescriptive and sit with people. And it was this very interesting relationship of, I don't have to own that. I have to, I have to be able to help identify where the gaps are, but I have a partner in that right now. And that to me was always really, really interesting. I actually, when I was at Groupon was approached by the head of that department to be like, Hey, you should come and actually join the enablement team.

You're really good at this. You love training your team. You've trained all of Groupon at one point. Like I was just somebody that always loved this idea of like, here's a way to do things. So I always kind of had that sort of up-leveling enablement bug, but then I also, I'm a revenue leader. I love that piece of it. I love building go-to-market. And so it had always kind of been a bit of a bug. And then even at Glassdoor, when we first opened the office, we didn't have those resources initially that were there. And my job was to hire a lot of people and make sure that they were ramped up and ready to go. And it was actually while I was at Glassdoor that I first got introduced to Sales Assembly, where I was tapped to come in and lead a session for new managers, because one of the things I loved doing at Glassdoor was help new managers to onboard, because I identified that there was a huge gap in actually upskilling and up-leveling leadership, especially if they were promoted from an IC.

I was like, there's no curriculum or third-party support for any of this. And I would love to be able to help people feel like they have some support there. And that naturally led me to being a speaker for Sales Assembly. And then Sales Assembly was basically all enablement, right? It was agnostic third-party skill development for go-to-market teams. And my job was to build the product that was going to deliver that and then also ensure that it was sticky. So going to spec it and then basically having a tech platform that was also enablement, it just, it felt like without realizing it at the time, it was sort of forming without me knowing it. Love it. And before I dive into my big question here, which, how do you, because there's a lot of reps, I'm sure you get it too, where, you know, reps might be kind of like, hey, look, the sales thing's great, but I think I might want to go into enablement.

I think I might want to go into coaching. What are some of the, I guess, pros and cons from your, like self-assessment, right? You talked, we talked earlier, prepping for this disc is big for you to understand personality profile types. I remember for me, for instance, like I didn't know I love training. I didn't know this was, but I had the opportunity, like I was always in sales. Sales is what I love true and through. And I had this opportunity to work for this Basho company. And I remember I asked my mom, who's been a career counselor since, you know, I was born and I've had a Myers-Briggs since I was five, whatever. And I had, I literally asked her, I go, mom, I got this weird opportunity to kind of be a trainer for the sales training company.

And I was just, you know, it's kind of odd. It's different. I was kind of, I'd love your opinion on it. And she literally starts laughing and she goes, John Michael, she's the only one who calls me John Michael. Uh, she goes, um, I never wanted to tell you what to do in your career. She's like, but if, if there was anybody I felt that was going to be a good communicator, it was you. And I was like, really? And so I legit went to, cause I had to, I had to train that I had to do like, as part of the interview process, I had to do some training and they didn't give me any guidance. So I went to Barnes and Noble and I legit got the book training for dummies and I opened it up and there was 10 characteristics on that front cover of how, you know, you're cut out to be a trainer.

And literally Christina, every one of them, I was like, holy shit. Uh, apparently I'm supposed to be a trainer. Right. And I took to it like a fish to water. So for those people out there who are thinking like sales, I love, I love the, the, but, but I like, you know, management or training in a lot of ways. Cause people feel like they have these career paths where they have to go be a manager. They have to go be this. And I usually tell them if you're one of the best reps, do not be a manager. You, you have to have something in you that, that likes working and seeing other people succeed because you're going to get paid less and there's going to be a shitload more on your shoulders and it's going to suck compared to you just being a lone wolf going out there and making it rain.

So how do you help people kind of guide them through that journey of their career and what to look for in themselves and then what pitfalls to look out for as they make that transition? The first thing is careers don't have to be linear. You know, we don't have to pick one thing and do that for the rest of our lives. I've seen so many people that have bounced in and out of enablement back into sales over to CS over to PMM and then back to enablement. And that is okay because all of them intersect with each other. And it comes down to what you want to do. And also there's understanding the difference between training, putting together curriculum, program management, and the coaching element that comes with being a sales leader.

And so there's a lot of people like, well, if I like training and I like working with people, then I should go into enablement because with enablement, I'm able to do that. Well, enablement rarely has the bandwidth or the ability to do coaching. Enablement's job is to look at the data that they have to determine where the entire team needs an up-leveling and how they build curriculum around that. So what is the consistent foundational knowledge that we have to give to our people and how do they deliver that and who does it come from? So it's much more of a program manager, executive level role that is ensuring that the foundational content, that teams need is available, and that you can identify where things are broken.

If you love working with people and really seeing them light up and watching the changes made with an individual person, like if you are the kind of person where I want to sit in a room and I want to watch the light go on, right? Like I want to coach you. I want to role play with you. I want to shadow on a call. I want to give you feedback. After all of that, you could say as enablement, that's actually coaching, right? And that goes more in line with sales leadership. And so it's what you want to be doing every single day and what kind of impact you want to make and what part of your brain you're going to be engaging. But I mean, enablement in sales leadership or enablement in being a sales rep or going over to CS, like they all kind of cross over each other.

And guess what? You can change and what you want to do can change. And you can decide that you're sick of holding a bag or you can decide that you want to hold a bag. I've seen more VPs of sales in 2024 that went back to being an account executive than I've ever seen in my entire career. And you know what? Love that for them. Go make a half a million dollars. You're going to be a great salesperson, right? So it's getting rid of this idea of like, I got to pick one and I get where it comes from, right? Companies do this to people where they make them think like, well, if you pick, you're going to get pigeonholed, right? If you've only ever been an enablement, who's going to hire you as an AE?

And that's broken too. Yeah, yeah, I agree. I think that it's interesting. I think a lot of the norms are being broken right now, specifically with all the AI stuff happening, which is where I wanted to kind of go to next with this, because your platform is, Luster is an AI coaching platform, right? Or with role play and all that stuff to help, you know, enablement. So like you said, like enablements really understands what the program is. And then coaching is where I think the least amount of effort is put because it's the least amount of time given to managers and enablement to actually coach, even though it's one of the most important things I think we can all do. So talk to me a little bit about like, first of all, tell me, tell us what Luster is.

And then I got one question for you that I want to kind of see. I'd love your feedback on because I'm going to tell you, I'm extremely excited about the potential of coaching, but I'm also very nervous, but I'll explain why. So first of all, give this context of what Luster is so that so I can take it from there. Oh, I'm excited and nervous too. I can't wait to dig into that, which is not something that you would expect to hear from a CEO of an AI company, but AI deployed in the wrong way, replacing the wrong things, I think is actually really, really bad. I don't think AI should replace coaches. You're hearing me say it right now. So, so, so what is Luster? So Luster actually uses AI role play and AI practice simulations to uncover a skilled proficiency map for everybody who is customer facing and go to mortgage.

We then use that proficiency map to look at the actual customer and prospect engagements that you have on your calendar. We predict mistakes that you're about to make and then proactively help you solve them by suggesting additional customized practice or additional training done by enablement or additional coaching done by your manager. And so the idea of Luster being this crystal ball where I can see because I can actually now measure reps and CSMs and BDRs at their level based on their proficiency, I can now predict where you're going to step in mud because of that in real time. And so think, so we're actually coining the term predictive enablement. So for every individual, I can now predict where I'm going to make a revenue impacting mistake and not just predict it, but I can do something about it and I can inform enablement and leadership to understand where they now have to engage and use their human equity outside of the AI.

So it's meant to be kind of a hero for elevating human enablers and human coaches, human coaches. So it's in my, it's in line with, right? I mean, I guess the nervousness of sales right now, I mean, after I came out of dream force and those types of things, I was like, holy shit, like these agents are doing the majority of what sales reps do. And I walked out of there basically saying like, where, what's your average sales rep going to cope, right? Like when these things are better and I'm looking at enablement and, and, and for, I mean, you, you probably saw, but I, I, you know, I, what scared me was for my profession, for what I personally do, right? Train and coach and, and that mainly training, you know, I do some coaching obviously, but you know, when I had Guy Kawasaki on, on the podcast and I, and I actually asked his GPT the same questions I asked him during the interview and his, and his answers were better.

And he had said it. So I kind of challenged him. And then I said to, I said, Guy, you know, I, I already had this conversation with you last night and you were right. Your, your, your answers last night were better. And my, my question to him was, well, he's like, why am I not out still surfing? Blah, blah, blah. And I was like, Guy, that's my question to you. I'm like, if I can get better answers from your GPT, what the fuck's the point of this conversation? And so what it really got me to be nervous about was when it comes to one way content delivery, right? Like you were trying to learn a subject, you were trying to learn a concept. You know, my, here's another example. My daughter, she was struggling in math.

This was last year. Um, her teacher was teaching in a way she didn't really understand. So we got her a tutor. Her tutor taught her in a different way. Then I opened up my version of ChatGBT and I said, you could act as a teacher, the, an expert teacher for a 14 year old girl who's, you know, learning algebra, algebra one. I I'm about to hand you my laptop and I need you to walk her through these problems. You can't give her the answer. You only can ask her questions and give samples. And I said, and she was kind of like, well, I go, don't ask me any questions, ask it. And at the end, you tell me good or bad, if it didn't work, it didn't work. But if it did, it did. And at the end, she got her homework done faster and it was a better experience.

And so even on that, like coaching on, on homework assignment, I'm looking at these AI tools going with most kids growing up in a digital world. So they're used to avatars. They're used to, and also the human factor here of not, a lot of kids right now don't like feedback. They don't know how to take feedback and they get very offended in a lot of ways when they get it, even if the feedback is totally valid because they might think their manager doesn't like them or whatever it might be. And quite frankly, managers suck at giving feedback. So, so there's a duality to that. So with that, it seems like AI coaching and training is way better than John Barrows standing up there trying to connect with 30 reps who all learn differently on different things.

So help me understand where the human element does fit in the training and enablement world when these tools can coach and listen and give you nuggets and training and all that other stuff in line immediately and way better than any individual person ever could. Yeah. The big thing that I still have a job in a year is basically what I'm asking you. Yes. Yes. But you know what you've been missing? There's an element that you, and again, I, I, I have an LLC where I have also been a trainer, a speaker and a coach for the last 12 years. And same thing where it's like, are the people like me suddenly obsolete because we're so subjective and we have our one point of view, what people like you and me and any other trainer, enabler coach out there has been missing is something that they actually can't do without the tool, but the tool doesn't replace them.

And what I mean by that is if you actually had the prescriptive data to know exactly what to train on for that group of individuals, you would always be more impactful than AI. But you don't have that because no organization has the ability to understand down to the skill level, what is the proficiency of my team and what do they need to be trained on right now? Because the other piece of that is the forgetting curve that we talk about a lot in enablement is if I am trained on something and I don't make that kinesthetic, meaning I'm doing the thing that I was just trained on within 48 hours, it's gone. So even if you deliver the most impactful objection handling training that you've ever done, you walk away, people are like, that was amazing.

If the majority of the people in the room aren't going to use that in the next week, then it's not going to stick. And they look at you and they go, yeah, nobody's really using it. It was really good, but we can't really measure it. Versus what if you had a prescription where you said the average proficiency of objection handling for this group of people is at a 42% and 90% of the people that I'm about to train are going to have to use this skill in the next 48 hours. You better believe I'm going to train on that. Or the data could tell you, well, you've got a great objection handling training and the company hired you to do that. You look at the data and you say the needs of your team right now, based on how they have to perform, not based on their gaps, based on how their gaps are going to impact them this week.

They don't need an objection handling training. They need a negotiation training. They need a rapport building training. They need a value propositioning training. They need a cold call training, whatever it may be. So if you were able to train prescriptively based on understanding where that group is and how their gaps are impacting them now, then you would actually need to train more. Because in real time, you would say the gap that the majority of these people have today is this based on what they have to perform. But then next week, based on the calls and interactions you have coming up, we got to do a training on this, right? Train before you perform. There's this interesting thing where I'm sure when you were in school and I was too, like I was a crammer before a test.

I would cram the information and then I would always do really well on the test. Statistically, people who cram before the test outperform people who just pay attention the entire time and don't cram. And it's because we have this much space to house what we need. When you cram before you perform, you perform better because you're focused. If you had a prescription for doing that every time you trained, you better believe you can't be replaced. So, but let's talk about the training so I get it, right? So it identifies very specifically, these people need this help, right? Why isn't the training from the AI better than me? So going back to like, okay, well, they need objection handling. Well, and you're talking groups consensus here.

Group consensus, like you learn differently than I do. Sarah learns differently than you do. So for me to try to, you know, we can get into neurolinguistic programming and making sure that people are kinesthetic and making sure they're writing shit down and listening to things and seeing stuff. So it connects with all the senses here. But at the end of the day, there's an AI bot that, you know, and I'm, here's an example. I, I, as, as all in it on AI as I am, um, I still haven't upgraded my iPhones at iOS 18 because I don't want that AI to now connect to literally everything about me because it's going to know every, I mean, it's right. And so because it will know everything about me when I'm having a good day, a bad day, when I'm open for information, when I'm not open for information, it theoretically could create training that resonates with me so well compared to John Barrows standing in front of a room of 20 reps who need objection handling, even if that is the deficiency it was highlighted.

So let's take the desire for humans to have human connection out of the equation. Cause I think that's the ultimate answer to all this AI stuff is I think for those of us, at least that grew up without a lot of technology, we're always just going to crave the human interaction here. But when your avatar, Christina looks as good as you do next to you and you're talking to me in a very tailored, very thoughtful, personalized way to me that helps me get it. I'm still trying to wrap my head around why John Barrows is better than that. It may not be for everybody, but then I think about why do we crave human interaction? We crave human interaction for a few reasons. One is empathy, which I think actually can't be discounted.

Human beings are biologically wired to connect to each other, to trust them and then be able to learn by recognizing empathy, right? If you are listening to me and listening to understand, I now feel like I am safe. I now believe you. I now trust you. AI inherently and will likely always, or at least for a long time, right? Like we're dipping into some, some real, like it could get crazy where they become self-learning or they become, you know, like Skynet, Skynet shit. But your empathy as a human being is one of the reasons why people enjoy that kind of human connection and hearing from another person. Also, your ability to tell a story as to why what you're saying is relevant based on your life experience is huge.

Again, and how adults and humans connect to other humans. Being able to tell a story and say, the reason that I am telling you what I am telling you is because I had this experience and let me tell you about my experience. And there is something about when a human being is training you, you don't have to take that as fact. You don't have to say, you know what, that human being gave me a tip and now that tip is the way. You actually still have the ability for autonomy in a relationship where you're being trained by somebody. Whereas this idea, if the AI is doing the training, the AI is never wrong. Like you're going to disagree with the AI. It's pulling millions of data points that inherently makes people very, very much lean out.

And also your ability to infer what is actually needed versus deliver the script that you've been given is the third magical piece of that. Somebody could come to you and say, I'm having a really hard time with rapport building. And if you're an AI, you're going to train them really hard on rapport building. If you're a human being, you ask more discovery questions. And you're like, why are you having a problem? Where is it showing up? What does that look like? Actually, you're not having a problem with rapport building. You're confusing rapport building with small talk, which is actually diminishing your value as a seller. And so we have to work on value selling and actually making the most time out of what you have with your prospects.

And AI is not going to do that, at least not for a long time. I don't want to say never, but your human brain that can infer and switch a topic based on only the experience and knowledge that you have, you will always be better than an AI. So I like that. I mean, I think the, you're right. There's just something about it's almost goes back to like the LinkedIn posts that I see out there generated by AI or the emails that I'm getting. And look, they're better than the SDR templated shit that they throw out with their cadence tools. But I still, no matter how personalized these AI bots get, I still, I, the only way I describe it to people is they just don't have a soul. Like the message doesn't have a soul.

There's something missing and I can't put my finger on it. And to your point, maybe it'll all of a sudden in the future, it'll be unrecognizable. But right now, at least there's, I can pick out every AI comment on my LinkedIn posts. It's, it's hysterical. Every one of them. I'm like, nice to stop using AI. And I comment on everyone. Stop using AI to post on my, on my fucking thing. That's right. So I do think there is just this, I just wonder like in the future when, with my daughter who's 14 years old, who grows up with a digital world, whether that's going to, you know, that transition of this AI coach is going to be so much better than the typical one. Because again, we're losing the ability to, to learn how to do it the right way, which leads me to my another, my next question, which is where are, I, I used to be asking the question, like where the fundamental is going to come from because I'm seeing AI take care of a lot of the grunt work, early career stuff.

Like a lot of the stuff that you and I did early in our careers and like just a straight up shit work we did. You know what I mean? Like updating this and taking notes and fucking making the calls. Like everything like, and it, but it, but it put us in a position to have context, to have business acumen, to be able to understand things. Whereas now a lot of that AI is taking care of those, that front end. And so my question was, well, you know, where are the future sales reps going to come from? But I've altered it now to what are the new fundamentals we need to learn and, and are they different, right? When I, you know, when you and I was the fundamentals, we learned the sales process, we learned how to qualify, we learned how to do these things, we learned how to, then we learned how to develop rapport along the way, you know, those types of things and business acumen.

I'm just curious, like have the fundamental, are the fundamentals changing of what we need to teach people? Or do we need to go back to the fundamentals to give people that foundation so they can leverage AI the right way? You know, it's tough because it's hard to tell who is actually also had the fundamentals. Yeah, that's true. Like a lot of people haven't even been trained on the fundamentals. You and I both know we run across folks that have, have never had a methodology training or have never followed a sales process, or they've kind of always gone off the cuff, or they came from a completely different industry and they've never sold this product to this type of buyer. And so the first is, it goes back to can you actually measure where people are?

Because if you can't measure where people are, anything you do is going to be a guess. And I would go so far as to say too, that we have been too rigid with AI or AI aside, and in non-buyer customer centric selling. Like we sell the way that we want to sell and it's about our product and our story and our dazzling. And like that is something that I think AI aside needs to go in the garbage. And AI has gotten more popularity because people are so sick of the rigid human processes that we put people through, right? You want to talk about robotic? I'd love to see your product. Great. I have 27 questions for you first, because I have to fill them out and put the information in my CRM or my manager is not going to approve this moving to a stage three deal.

Like literally heard that. You want like, yeah, AI is going to be better than that. Like because that's robotic and soulless. And so we have to not be so rigid as well. Yeah, I think that's, I mean, that's why I'm positioning 2010 to 2022 as the golden age of sales. Like we are way over engineered the sales process. We taught these kids on technology and process. We didn't teach them how to sell. We didn't teach them how to have a conversation. That's right. And now because we turned them into robots, they're getting replaced by robots and it's, and it's obvious, right? I mean, again, I tell reps all the time, I go, if you don't think you're in trouble, pretend like you're a customer going to chat GBT and, and qualify, you know, for me, I'd be like, Oh, I'm John, you know, I'm a, I'm a CEO of a sales training company, or I'm sorry, I'm a, I'm a VP of sales of a 50 person sales team.

I got 20 SDRs, 38 E's. This is what I sell. This is who I sell to. And I'm looking at training for this. I'm looking at the JB sales training. Tell me what I need to know. And when you realize in a five minute conversation, you get more value out of that than some dumb ass kid who's going to ask you bant questions and thrown through a piece of shit demo. Yep. You realize how in trouble we are, right? Or the vast majority of the sales profession is 100%. We don't listen to our buyer. And, and it's also, this isn't, this isn't the sales reps fault. Like they're, they're doing what they are being told to do. And a lot of times, like even, even as a sales leader, I have been tasked to hold my people to process that I know is damaging the buyer relationship.

I've been in that seat where I've been like, you, we really need them to do that first. Like they have to qualify for a demo, but their wallet's out. Like this goes against human buying theory. Like why would we do that? Right. And yet it's like, this is our process. This is what we do. Right. Like that rigidity is why to your point, it's like people like, I'd rather talk to a robot. If you're going to be a human acting like a robot, at least for a robot, I can quickly click through the boxes and just get to the demo. Right. Like, so we've kind of done it to ourselves a little bit. I don't think that that means all hope is lost and we're all going to be replaced by an AI because the overwhelming majority of buyers, I don't care what generation they're in, don't actually want to be sold to by a robot today.

This could change. Yep. Absolutely. So I think that gets us to the sales reps that care, right? And, and, and want this to be their profession, not the ones who are just kind of, Oh, I, my degree sucks and I try to, I need to make some more money. Um, what is, you brought this up before we, uh, in the prep, let's talk about mastery. And I mean, first of all, I always say sales is like golf, right? You can never be perfect. You can't, you can't shoot a zero, right? You can always get better. It's ups and downs and everything else. So, you know, mastery, I think is a, is a, I don't think anybody can master sales, quite frankly. I think there can, you can master components of it, but what does mastery look like to you?

And then why is it so difficult to attain right now? It goes, I mean, it's like, I feel like a broken record. Nobody can measure anything. Right. When I think about the fact, like, so when I think back to being a sales leader or a CS leader or a go to market leader, there would often be times, especially in the last five years where surprise, we're not hitting the number. We're not hitting the metrics. Our velocity is slowing down where our win rate is rapidly dropping. NPS scores are tanking. Churn is going up. There's all of these lagging indicators that something is broken. And so the CEO goes to the revenue leaders and the CS leaders and they say, what is wrong? What is the problem? Fix it.

And then what tools did I have at my disposal to figure out what the issue was? I could listen to a thousand gong calls or look at the sum of those and try to identify, is it a skill issue? Is it a behavior issue? Is it a will issue? Is it a product market fit issue? Is it an ICP issue? Do we have the wrong sales reps in seat? Are the sales reps properly trained? Which ones are good? Which ones are bad? I can't tell based on the numbers. Was this performance a standard deviation or not? So I'm left with all of this guesswork and I have to continue performing. So my options are, I can either take some people off of their day-to-day job and have them do an in-depth analysis to identify what are the gaps that are stopping me from actually hitting my number.

And that's probably going to take three or four months, right? And then I'm going to get that answer. It's going to be subjective. And then I just have an answer as to what's broken. No idea how to fix it. Or better, why don't I go pay somebody six figures to come and run that analysis for me from the outside? And that'll take six months. And at the end of six months, I now have a map that tells me everything about my business, according to them, by the way. Who knows if that's accurate or not, on what's broken. And then great news, because it's high growth tech, after six months, everything has changed. So the issues that we had six months ago aren't even the issues that we have anymore. So now we start all over again.

So we don't even know what mastery looks like. If you go to 10 tech companies and you find three people in every organization and say, how long is your new rep ramp? None of them are going to give you the same answer. How do you measure a new rep ramp? None of them are going to give you the same answer. Nobody knows. Nobody's measuring it. Everybody is guessing all the time because there is no quantifiable, accurate, objective data that tells us what is the denominator by which mastery for this role in this segment at this company actually looks like. And now that we can identify what mastery would look like, how do we know where people's gaps are to achieve that mastery? We don't have any of that.

We don't have any of that, right? And so that's why, that's why. So are we ever going to be perfect? No, perfection is boring. We don't even know what good looks like. And so then we lean on, well, I guess good looks like hitting your number. If you're not hitting your number, I'm going to pip you and you're going to be gone. And then we're going to hire somebody that'll slam through this and hit the number, probably making our customers collateral damage in the process of that. But that's just the way we're going to function. Yeah. It's, it's funny. It's the same, it's the same mentality. I have a, for like ROI, right? It's like when customers ask me about, John, what's the ROI of your training?

I literally always, I'm like, really? You want to have this fucking conversation? Oh, what do you want me to say? Okay, fine. What is your current conversion ratios for your pro your personalized emails to your tier one target accounts at the executive level? What's that number? Well, uh, or okay. What are your cold call conversion ratios when you do a power hour to this persona using a message like this? Or, uh, I don't know. Well then how about your cadences? What's your best? Like, here's an easy one. What's your best performing cadence? And, and tell me why it is, right? So we can use that as a baseline. Well, or, uh, okay. So then please shut the fuck up about ROI. Because if you don't have a baseline number for us to measure against, how could I possibly give you a number?

30%. That going to make you feel good? Put it on your list, right? And it's the same thing to your point with measuring a baseline of where a rep is at a certain skill set, right? And so this goes back to the science and the art. I think the science of, of laying the foundation in that framework of, okay, let's understand the metrics and where people are, but then the art of, okay, now how do we get them there? And, and outside of enablement and that type of thing, what I'm trying to do is empower individual sales reps to take it upon themselves to, to upskill themselves. Because I just don't unfortunately rely on organizations to provide the right training, the right coaching, or any of that.

And there's so much free content out there and so many cool tools out there. So if you were to advise an individual sales rep out there of how do you lay a baseline to figure out where you are and then where to start working on the different components to start seeing a measurable impact, what would that look like? The first thing you have to, it's, it's what we're talking about. You have to have a denominator by which you're measuring everything by. And I have bad news for all of you. The denominator can't be resulting metrics. The denominator can't be whether or not people are hitting quota because John, you and I both know that when you start to do a deep dive on who people think their top reps are, they are not their top reps.

They are often reps that were inherited a really, really large deal, or they got a great look of business, or they had a lower quota that month, or like whatever it may be. I'm not saying that all top reps aren't top reps, but what I'm saying is most companies don't even know what the makeup of a top rep is even. So if you don't know what you are measuring and you are defaulting to who is hitting quota and who is not, what you're going to do from there is you're going to look at the people who are hitting quota and you're going to go, my God, Christina, you're so great. What do you do? What's your process? Do you want to be a subject matter expert and train the rest of the team on what you're doing without even identifying if what Christina is doing is great for everybody or great for the customer because we don't know what good looks like?

So I get you have a business you have to run. You have to hit the number right now. You have to do something which is better than nothing. But every day that you go by and you cannot measure proficiency, then you cannot lead to mastery. And every decision that you make is going to be a guess. It might work out for you. It might not work out for you. Good luck defending that at your next board meeting. Yeah. Say that again. If you cannot measure proficiency, you can't achieve mastery. I like that. All right, cool. And I think, you know, achieve mastery. I think that's the thing right now where I'm telling reps, like I get so frustrated with reps when I, when I tell, you know, when I'm up there taught training and I'm like, Oh, you know, chat GPT, you know, use this or do that or use this tool and whatever.

And they're like, well, our company doesn't invest in that. We don't have that tool. I'm like, pull out your fucking credit card and put 10 bucks a month on the goddamn thing. Like if you can't invest in yourself, then why would, why would somebody else invest in you? And I, in a lot of ways, right? I mean, I could give you a tech stack for like legit, like a hundred bucks a month that will make you one of the best sales reps on the planet if you use it right. And if you're not willing to put that money on your card and invest in yourself or take a training or just scrub YouTube for a little while and pick different components and start testing different shit out, then you're, you're not going to be one of those reps that survives.

You're going to be one of those reps that gets replaced by AI. And that's where I'm trying to get reps to is just wake the fuck up. Like it's the information is out there. You just need to go figure out what components of your process need help and then start split testing and trying different things and, and really just constantly be evolving. Cause you had said it, what worked six months ago, shit just ain't working anymore right now. No. And the sooner you realize that and you're okay with it, but people also don't want to call their own kids ugly, right? People get so connected to the bad processes and bad training that they build, right? They're like, I know it's crap, but like it's my crap.

And it's like, but now everybody is crap, right? Like we're all so comfortable running marathons with pebbles in our shoes. And you're like, why don't you just take the pebble out of your shoe? And I said, well, my company says I have to keep the pebble in my shoe. And it's like, take the, take the pebble out of your shoe. Like it's, it's like, what do you mean? Like, I don't care. Like your company wants you to hit the number. So to your point, spend the money on the tech stack, write it off, open up an LLC and write it off as a personal business expense. If that's going to help you hit the number, find a way because you know what AI doesn't do, find a way. Human beings are resourceful. We are scrappy.

We push back. We break the rules. And without a rule broken, nothing has ever been invented. And so if you let yourself be replaced by AI that can't do all of those things, maybe you deserve it. I don't know. Yeah, no. And I think that's, I mean, quite frankly, I think there's a lot of people that do deserve it because they are just going through the motions and they don't give a shit. Now, I agree with you. I don't think it's a lot of these kids fault. I think we've put them into a system. We've, we've allowed them to not care and we've spoon fed them a lot of stuff. And again, put them more into an assembly line versus, uh, you know, a career that they can learn from. And I think we need absolutely need to get back to that from a coaching standpoint and everything else.

So long way to go, but it's an interesting time to real quick, Christina, one more. Let's talk a little bit about, um, uh, you're with, what is it taking the lead podcast, right? Yeah. Talk to me about that. Cause you're, you're a huge, um, proponent and obvious supporter, women in sales, women in business. And it's talked to me a little bit about kind of why you decided to start to really kind of have a megaphone for women specifically in business and in sales. And what are some of the things that you're seeing? Cause the, I'm, I'm worried that we've, we've taken too many steps back, um, over the past probably four or five years and everybody thinks we've made progress, but it, it, if you really pull under the covers, it doesn't feel like we have.

Um, so help me understand why for you, um, you're passionate about it and, and what are some of the things that you are seeing out there that are good and some of the things that you're a little worried about so that we can kind of get people to pay attention to that as well. Yeah. I I've always been a big believer that a company makeup should reflect the world makeup, right? And if you are missing anybody's thought processes or anybody's experience, um, or anybody's acumen or background, then you're forever going to be handicapped by that. Um, and I've been lucky enough in the last couple of years of my career to be able to have a bit of a louder voice. And one of the things that I always say is what are your stairs made out of, right?

Like, like, what did you climb on to get where you were? Did you climb on top of other people? Did you miss an opportunity to help someone and take them with you? Are you using the privilege that you have for good? Um, as much as you possibly can. And that doesn't mean that you can't do things for yourself. It doesn't mean that you can't want to make a whole lot of money, but I'm also a big believer that I want all the voices in the room as much as possible. And I think the pendulum can swing too far on both sides of that, to be honest, because I've seen a lot of diversity initiatives that take certain folks who are, uh, not as diverse and say their voice is not important because there's been too much of that.

And I said, but that's not truly equity or equality. Equity or equality is that there's room for everybody at the table, including folks who have always been there. I don't want to remove people who have been at the table. I want to add more people to it so that we achieve more balance. Um, I also never believe in talking in a room that I don't belong and I don't have a right to belong in. So I am a woman. I am a mother. I am a lot of these things. So I can speak up for other women and other mothers and help them to identify and help to bring their voice to the world, but then also encourage the people who don't look like me. I don't want to speak for you, but I want to make a space for you.

And if I can make a space for you, or I can relate to you, or I can help somebody discover what you've done. My goal is to change the face of tech, not eliminate some faces, but just change it a little bit so that everybody feels like this is a space for me that I can succeed in. We talked at the beginning of this podcast about the fact that nobody would have anticipated that coming from where I came from, that I would be where I am. Right. And where I am happened because a group of folks saw something amazing in me and gave me a shot, right? Like that's what happens so often is you need someone to see the magic and give you the opportunity. I want to pay that forward. Yeah. I think that's the, that's the thing that's, you know, going back, you know, it was really interesting.

You know, we all have these implicit biases, right? Just the way that we grow up and everything else. And I think I remember, let's go back to your, you know, your dad being symphony and you said he was a professional. What was he again? He was an opera singer, opera singer. So the symphony, I remember the, the Boston symphony orchestra here in Boston. They started a while back doing blind, um, uh, interviews effectively blind tryouts because they found that when they didn't do a blind tryout, right, when they saw the person up on stage, men were, you know, recruited 10 times more over women. But as soon as they put the curtain down and they just listened to the music, it was well over 50% women because they didn't have that bias.

And I'm trying to, you, you brought up the word privilege and, you know, I, you know, I have a tattooed on my arm, right? When you're accustomed to privilege, equality feels like oppression. And I'm trying to figure out ways for people to not be offended by like, not, Oh, Oh, look at I'm not, but, but just recognize their privilege and recognize the lens that they look through and how it's just not the same as everybody else. And maybe just maybe try to try a different lens on every once in a while, because the more feedback you get from the different types of, you know, people out there and diversity in the background and stuff like the more creative your business is and can succeed. The data is undeniable, but it's, it's so hard that you look at the data and the facts and there's, there's still not that shift that, that reflects those facts.

And it's because of this implicit bias, I think that we have. And so appreciate the work you're doing with the podcast and just trying to get the word out there too. So thank you. Thanks for that. Yeah, you got it. Anything else that's, um, uh, that's, well, let's talk about, well, let's wrap it up and talk about where people can find out more about what you're doing, uh, both with, um, the company and also with the podcast and also all your social stuff. So how can they connect and where they, where can they find out more information about what you're working on, Christina? Yeah. So you can find me on LinkedIn. It's Christina Brady. You can learn more about Luster. You can reach out to me on LinkedIn, send me a message.

You can go to our website, luster.ai. Uh, a lot of the principles that I talked about today around how do you actually get that data that allows you to inform those decisions. That's, that's what we do, you know? And the reason we do that is selfishly, I struggled with it for so long that I said, I'm just going to build, I'm just going to build it because with AI, I can now. So if you want to hear more about that, you can find me there. Um, the podcast is where you stream any podcasts. We've taken a pause on new episodes because I've dedicated a lot of my time to evangelizing Luster and getting this company off the ground because I owe that to my customers and my employees, but all 80 episodes are still out there.

You can find it anywhere. It's taking the lead. It's got a cool graphic of what I hope I look like. It's a beautiful photo. So it's, it's, and you could find that. Awesome, Christina. Well, thank you so much. It's great seeing you. And I'm, uh, hopefully we can see each other again. Not, I think we see each other once a year at like dream force at the very least, but it's like a random run in life. We got to fix that. Yeah. So I, I haven't, I haven't been on the tour as much recently since COVID hit. So I've, I've kind of become a homebody cause I, I think I, I think I overdid it for about 10 years there. And so now I'm, I'm very happy in my own little attic here in my little corner of the world, but I do get out every once in a while.

So let me know what the next conference you're at and, uh, and I'll see if I can swing by and say hi. I will. I will. This has been awesome. Thank you so much. Absolutely. Thank you so much. And everybody, I hope you enjoy the conversation as much as I did. Like I say at the, at the end of all these podcasts, go out there and make somebody smile today. Cause no matter how bad your day went or how bad you think it's going, you make somebody smile today and you know, you had a good day. The world needs a lot more of that right now. So thank you all very much. And I'll see you on the other side. Hey everyone. I hope you enjoyed that conversation as much as I did with your support and our incredible guests.

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