Jaime Diglio - Embracing Your Superpowers in the Age of AI

All right. Before we get started on today's podcast discussion, I got to do a little promo here and this one's a big one. So HubSpot's annual inbound conference is coming up September 5th through the 8th here in Boston. And it's right in my backyard. I go to it every single year. It's one of the marquee events that I absolutely put on my calendar. And even if I didn't live here in Boston, I'd come to this one because this gets some of the best and brightest across sales, marketing, customer success together to talk about what's happening in the industry and share best practices, tactics, and all sorts of different things about where the industry is headed and what we need to do to drive results in this crazy big world that we're all living in right now.

And with inbound, they get some super cool guests on this and speakers. I mean, including this year is going to be Reese Witherspoon. We got Derek Jeter coming up and I know he's a Yankee, but we'll let him come to Boston because he's actually one of the Yankees I like. And then we got people like Sam Jacobs, a good friend of mine who's going to be speaking. And myself, I got a speaking engagement. So they accepted my speaking engagement at this event. It's about sales-ready messaging where I'm going to be talking about a specific equation that we use to create sales-ready messaging that aligns sales, marketing, and CS. And you can use to implement into some of these AI tools to really drive some pretty impressive results.

So if nothing else, you're going to get some free training from me if you come to this thing. Now there's two types of passes. You can get the general admission pass that gets you all the speakers, trainings, and programs. And then the VIP pass, which is limited availability and gives you VIP lounge access, exclusive welcome parties, and access to some of the speakers that you might not have otherwise. So you got to come to this one again, September 5th through the 8th here in Boston. Sign up at www.inbound.com to get your ticket today. Let's make it happen. 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 Jamie Diglio. I've known Jamie for about three years now, and I've been a huge fan ever since we first met. She's the founder of InFirst Consulting, where she trains leaders and sales teams on how to win at work and in life through her win room programs. She's got a master's degree in industrial organizational psychology and over 20 years of experience in leadership roles at places like Gartner, Microsoft, Swalom, and various other high-growth startups. In our conversation, we talked about how many successful people think they're winning in life, but they're really actually stressed out, over-committed, and unhappy, and boy, do I know that. Throughout our conversation, she shares a surprising yet really straightforward technique that can help people move away from that mindset and that causes burnout and towards a mindset that produces success.

We talked about how to create a culture that focuses on the sales reps' unique value and what they need to thrive as their authentic self. And then we discussed topics like transparency and what leaders need to do to build trust in their teams and get the most out of them. Look, our entire conversation could be summed up as how we need to evolve in sales right now and really start moving in a new direction to address all the challenges that we're faced with in this evolving world. So I hope you enjoy this conversation as much as I did. Jamie, how are you? Welcome back to the Make It Happen Monday podcast. It's great to see you. It's Monday. I'm happy to see you. Yeah, we've actually seen a decent amount of each other recently with the Bryant College.

So I'm excited to kind of spur this conversation too, because man, are things going crazy right now. It's an interesting world to say. Yes. Breathe. Yeah. Well, I mean, we'll get into it. But I mean, that was the one thing that, you know, part of the topic down at the university was like, all right, we're teaching sales, which is great. But what are we teaching about sales at this point? Because things are moving so exponentially faster than they ever have before. So it's, we're going to get into resilience here, which I think is part of the bigger, you know, bigger picture answer to this question of what the fuck's happening right now. But Jamie, before, before we get into that, give the audience a little bit of context here, where you're coming from, what you're up to these days and what your background is.

Sure. I spent the last 20 years in sales leadership at Gartner, Microsoft, Slalom. And I saw a continuous over the last 20 years selling into organizations and with their technology transformation, I saw a continued gap with the emphasis on people and how to, you know, your competitive advantage is how you like, what, what's different about you and what brain, you know, how do you bring that to the table specifically with selling? And so I saw that that continued to get watered down more robotic. Like if you, if you don't, if you teach your sellers to not be like work like humans, they're not going to sell. So since, since that, seeing that breakdown, I have now have a company, my own company, where I go in and work with new leaders, new teams, new sellers, and help them with really bringing forward what their unique value prop is.

Removing, I always say it's like about keeping it real. How do you keep it real? You can tell when someone is not, when they're, they're not comfortable on their own skin. So the whole goal is to get people to feel really confident and sort of in sync in their headspace with how they show up because every conversation is a sales conversation. So doing these, these trainings and programs with different organizations and individuals. So yeah, been busy. Yeah. I was going to say, I, you know, now more than ever. And I think that's a good starting point for the conversation because I think there's a lot of people going through, including myself, by the way, uh, going through a crisis, crisis of conscience right now about what really does make us special in this world of AI.

I mean, I, I was, I was talking to Scott Lease, right. Who was supposed to be down there at the, at the speech with us, but he couldn't make it unfortunately. And I had done a, you know, I'm coming out with a, you know, I'm rebranding myself and coming out back out front. And I sent him in a video as a prep. And I said, Hey, you know, what do you think of this? And it was effectively like, Hey, we've gotten past 10 years have been easy in sales, you know, specifically in SaaS sales. And it's been great for us, but I think it's made a lot of us, including myself pretty lazy. And we've relied on the technology. We've tried to over-engineer the sales process. And, you know, I think we've skipped a lot of the fundamentals.

And so now, you know, and Scott was even saying, he's like, John, after I watched your video, he's like, I'm starting to question myself. He's like, I'm, I'm starting to question the past 10 years. And was I really as good as I was these past 10 years? Or was it because of the economy? Because it was a, because I was just in the right place at the right time. And quite frankly, I'm, I'm asking the same questions and that's why I'm, I'm glad I always sell. So I haven't like been talking about sales for the past 10 years and not doing it. So I'm like in the shit right now still, but it's still kind of like, wait a minute, am I, was I as good as I thought I was? And I am now having high anxiety with all the shit that I am seeing from an AI standpoint.

And last point before I hand it over to you is I just did this post right this morning on this AI bot that did that, that was the audio, right? And my producer took a bunch of my videos and podcasts, plugged them in, and then created this rendering of my voice. That sounds pretty close to my voice. And so with this, I mean, you talk about this, you know, your differentiator, if you will, right? Like, you know, knowing what your superpower is, what the fuck is somebody superpower coming into this world right now? I mean, authenticity, obviously, but authenticity without insights and without all these tools, where does that leave us? Well, the thing that a loaded question, I know the thing though, that you touched upon, uh, where I continue, you know, we've, we've sort of, we've built these, um, these sales processes and organizations around all these, the tech stack and just go over the process.

And what I see over and over again is there's this foundational layer that's missing. And the foundational is, I always say foundational over fancy in how we think about, you know, it's like, uh, my kid plays, kid plays baseball and basketball and like, they'll be like, oh, I just want to get out there and play. I'm like, dude, you don't even know how to throw the ball yet. Like, how do you catch it? Like all these basics that you build upon. And so everybody wants to be the superstar or whatever, like right away, but they, they skip this, they skip the foundational of like, why, why do you even work here? Right? Like, what are you about? Why are you in sales? Why'd you choose to come here? Um, understanding who they are, um, as an individual and tapping into that.

So that foundational piece, uh, when we, when we set that, it allows us to build and have more, um, confidence and strength in how we're showing up with all this adversity. So that's what it's a miss. It's missing piece right now. And so how do you build that confidence in, in such a world? And look, I feel extremely blessed that I was a Gen Xer. I had to figure it out as I grew up, you know, I didn't get a lot of guidance from, you know, my parents were great. Don't get me wrong, but it was definitely a, Hey, I mean, if anybody watches, it's funny. Uh, what is it? What's it? Stranger things. Did your kids into stranger things? The show? Yes. My daughter is. So if you go back and it's the eighties, right.

And you notice like the parents, like literally do not give a shit where their kids are at any time of day. Like the kids are literally in fighting aliens and they're not even hold. They don't show up for four days and the parents like, huh, what's up? Like, so we had to figure it out and we grew up without technology. Yeah. There was anxiety with what was going on, but we weren't inundated with 24 hour news and our iPhones and all that other stuff. So the anxiety level right now is an all time high. Right. So confidence is that I think, you know, I don't know if there's a statistic on this, but I think personal confidence is going to be an all time low right now. Cause I don't even know how to build it at this point with what's happening.

I mean, as soon as I start focusing on from like, I'm talking to myself, who I consider a pretty confident cat here, you know, I I'm like, all right, let me learn this. And then a day later, a week later, what I just learned is irrelevant now because of this new thing. And so what does that mean for me moving forward here? So how do you start to instill confidence in this, in this generation coming into work so that they can be resilient and can take feedback? And then how do we reflect that on ourselves as leaders? Hmm. Well, I think the thing we are just naturally wired to, uh, focus, like minimize the things we're good at and maximize the thing, like maximize the things that we're not good at.

And so we all have things that we are good at naturally, even if they're just coming out of school and going to their first job, there's certain things that you lean into that you're interested in. And so I I'm like, I'm almost, it's like a clean slate. Like it's like, like you stop listening to all the noise, right? Getting back to yourself. This is like back to basics. It's like the ABCs of life, like getting back, like literally, literally there's too much shit, right? We taught, there's too much stuff that, that are, we're pushing, and this is happening in every organization, just pushing information, pushing more and more and more. And that's not communication. That is not, like information is not communication.

It's just pushing it and drilling it down on people. Whereas, you know, we're, how to really build that confidence is sort of to remove everything and sort of get, get better about how do you think about your thinking, right? Everything around how you're showing up. It's like the basics of like, if you sit and worry about what you don't want to happen, you are never going to have, you know, succeed in what you want to happen. So learning how to train our brains to sort of manage in this crazy environment. Yeah. Yeah. It's like one of the things that I came across, you know, we talk a lot about, or I've read a lot about energy management, right? And a lot of energy management is about like when you do things during the day, right?

So in the mornings you have energy to do this and then you eat the frog and you block off things and all this other stuff. But I looked at it from a different perspective of like what gives me energy and what takes energy away from me. And I mean this with friends, family, activities, tasks, whatever, and put together this matrix of, of, you know, on the X axis is helps you achieve your goals, does not help you achieve your goals. And on the Y axis is gives you energy, takes energy away from you. And if you go through the simple exercise of putting everything that you do in one of those quadrants, you know, the idea is do, you know, people say, you know, fix your weaknesses. Bullshit. Your weaknesses are your weaknesses for a reason.

You don't like doing them. Right. So you want to minimize their impact on your success, but you don't want to focus on trying to fix them because then it takes away from what you're doing good at, right? Right. Right. Yeah. I mean, and that is, so if I think about, I just did a talk on a Ted talk and it was about, all about the war room to the win room. And we're the champ. One of the biggest challenges we have is that most of the leadership that is happening today is the way that we've been taught to lead over the last 30 years. And it's very traditional, right? It's like traditional versus modern leadership. So when I think about, when we think about war room and how I define it is that's where you work against results.

It's where you doubt yourself. You have uncertainty. You don't, you're not clear in what you want, what you need, uh, you self-sabotage. And what's happening is that we're using, we're using war room techniques to try to win, right? Traditional war room techniques, leadership techniques to try to win. And so when I talk about this win, what, what win stands for is what I need. It's where you're clear in your goals, your direction, what you're aiming at, your ambition, your strengths, uh, focusing on what you want, not what you don't want. And this, one of the bigger challenges is like that you said, it's like, like old school leadership. I mean, that happened to me over and over again. It's like, Jamie, yeah, you're great at selling.

You're amazing at selling, but you're not good enough at spreadsheets. And I'm like, no kidding. I just like don't like spreadsheets. Right. I'm like, that is somebody. So I'm like, there's someone else that loves spreadsheets. I don't let me be out there selling. So we've gotten into this, um, modern leadership is more around how do you double down and triple down on your people's strengths and you put the right people in the right seats on the bus. Yeah. Right. And like, how do you figure out how do you figure out where people are supposed, you know, where they're going to amplify their strengths in your organization? Yeah. That's, I mean, that's kind of the good and the bad thing about the segmentation of roles, right?

I mean, the good thing is it allows you to focus. The bad thing is it might be a focus on something you're not that great at. Okay. You know what I mean? Like full cycle sales rep. There are some sales reps who are fantastic at meeting with clients and even if they're brand new, you know what I mean? Even if they're fresh out of school, they're just somehow they have the charisma, they know how to engage, they know how to be curious and ask good questions and engage. But we, but their starting point is SDR rolled and you got to make 50 dials and they might be horrendous at making those dials and staying organized and running cadences. And you might drown the creativity and their ability out of them because you're forcing them into this system that says, this is where you need to start.

Do you think we need to change how we look at outside of management? Obviously, I think we need to change. Do you think we need to change the overall structure of how we introduce people into sales? I think that there can be a way to rotate roles, different types of, you know, I saw your post, you did a post like the other day that was sort of talking about the, the need to sort of come back in, in the office versus hybrid. And then back what, you know, back when I was starting and I'm sure the same as you is like, we did ride alongs. We had somebody we were mentored with. And even before pandemic or whatever, though, a lot of that had gone away more. It would be more of, and back to my point about sort of automating everything, um, and seeing this transition of just in my years at Gartner and in Microsoft, seeing how companies were continuing to take learning and training and like modular, modularize it.

And so it was like, you're sitting in front of a screen. And so this idea of really driving the dynamic engagement in conversations, I mean, Hey, this, this new generation, I mean, this generation of, uh, of, uh, of young adults that are coming into the workforce, the thing they need the most is to learn how to communicate, right? Have conversations, right? I always say, it's like, it's all about connection. Every conversation is a sales conversation. So figuring out, um, and I use different tools, data-driven tools to understand where people's strengths are. Um, and so we can understand if this person, is this person better suited for an operations role? Are they better suited as a farmer or a hunter based off of the way that they, uh, you know, they're wired.

So you're, I, yeah, I do think that there needs to be, I don't have an answer for it in terms of, uh, like what that structure is. But I did like when I first started, there was more of a rotational type of, um, a segment of how you would go in for six months, you do lists and then you'd learn this and then you'd learn this and you would rotate. Yeah. I think that's, uh, one of the things I, I, that I've talked about this before, but I love the model. Cause I've been preaching for a while now that the predictable revenue model is broken, right? I just think it's broken. It's not customer centric. It doesn't. And it, it, it works if it works great for companies, if that sales rep stays for the next three to five years within your organization, it does not work when the average tenure of a sales rep is 12 months or less.

Right. Um, but the, the transition was a, uh, instead of SDR, and I do think SDRs are, I think it's good to get in. And that's why I read to that post. I think the first couple of years, be in, be in the room, you know, get your ass kicked because I go, and we'll come back to resilience. You know, that's going to show whether you're going to be resilient or not. Um, but then after that, instead of going to an AE closer role, you actually go over to customer success, you go over to account management and you learn how to cross sell, upsell and quote unquote, close, but you do it in a bit of a safer environment and you get use cases and understand how the client actually uses it, what the real value is, and then move into sales because it'll just give you empathy.

It'll give you understanding. It'll give you a better perspective. So I do think there are some shifts that we can make in the existing model to soften the harshness of the reality of each new role. But I also think that we're going back to full cycle sales full blown. And I just don't know how we get those sales reps back to being able to run full cycle, um, with where we're at right now. Right. Unless you're like change, like I said, changing the model where you are literally like partnering up with a more tenured, more tenured and a more junior. I mean, that's what I experienced when I first started. Yeah. Yeah. Yeah. Those, those ride alongs, but it goes back to those ride alongs. And now we're in this situation where, you know, it's not even just like the client or the companies who are hiring sales reps are, you know, are forcing this model.

It's the buyers, you know, they're, they're in a much more controllable position now when it comes to sales. They have all the information and they can dictate when and where and how we talk to them as opposed to us going on site and kind of building a rapport and having time and being, you know, being, it's super rude to kick somebody out of your office when you go over a minute or so. Like now it's like, sorry, I got to go click. Right. We're gone. So the buyers are getting more and more used to this environment. So I'm, I'm wondering from your perspective, we'll get back to grit and confidence, but what value, and I know this is a big question, but what value do you think a sales reps bring brings to the equation at this point?

I think being, um, the connective tissue between what they, the information they know or they have heard, um, and to get to that next step in, in the buying cycle is, and sort of, I think of the done well, it's, Hey, you know, I had this network. We were talking about brand, right? Like, how are you building your brand and who are you connected to? So when you do talk to the customer for the first time, be like, Hey, I know these four companies that I work with, would you like me to part, like connect you with them? They're using the technology. Uh, they're using the services, uh, to really be a conduit to help with like educating and connecting. Yeah. So to me, I feel like that, that was always what I did as a seller because I was not the expert in technology.

I was not the expert in financial services. I was not like, I wasn't, I was just an expert. I became, became over time an expert in sort of understanding what people's motivations and drivers were. And like, I don't want to waste your time. How can I be of help to you and really doing it in authentic? Cause it was real. Like I, like, I think I've always thought, I think as a seller too, is sort of thinking long game, which is one of the big conundrum sellers have because they've got leadership that are on their asses about short game, but like you want them to be a client for life so that you, I mean, I think about the clients I had 15 years ago that I'll, they'll call me up and ask me stuff and like, I don't know, but I'll help help you figure it out.

Yeah. But that being that connected tissue and sort of putting things in context. And I, I think that that's one of the biggest things as well as showing up as real because it's so uncommon right now. And well, really in a long time, it's so uncommon to show up authentically, um, as just a person with no like facade. Yeah. Right. I mean, it's like, hello. And so when you do that, people are like, huh, that was different. That didn't. And it's not even like, it's, it's like, they just feels different. Yes. Right. When you remove, you can tell when someone's not being truthful or just not comfortable in their own skin. So it's like, I always say, it's like, it's like, how do you get people in sync with, you know, like their own internal, like how they're showing up?

Uh, because it, it resonates that's where trust, confidence, the sale happens. I agree. Like authenticity is just craving it right now. And everybody's using it though. Like they're like, oh, it's like, let's be authentic. I'm like, well, what does that even mean to you? Well, and that's what it was. Yeah. Like what, what do you, how do you know what your authentic self is when you're, especially when you're young? I think I, I've gotten confidence over the years and making a lot of mistakes and, and being pretty self-reflective on a lot of stuff, but you know, I've, I've had to go through some coaching, you know, understand your why and your values and all that stuff. So how do you, how do you know who your authentic self is when, when you're coming out of school?

Wow. So, uh, that, that is, um, when you're coming out of school, I think a big part of it is noticing. So one thing is, and this is not a one person job, like figuring out your authentic self. It's not just a you job. It's like, it's a combination of the people around you. But the first thing is noticing, uh, but what are the things that you have, uh, that you like to do, right? What are the things that you could do all day long and, you know, and enjoy it? Um, what are like looking for patterns? Now, one of the things you can do is this is a little, the little hack that, um, I give to people when I work with them is reach out to, and if you're just coming out of school, it could be the people you did your internship with or other fellow, um, professors or, uh, um, fellow students is reach out to those people and say, you know, could you describe, I'm doing some, um, either self-awareness work or, um, focus on my, uh, my skills and say, could you just tell me or just text me back the first three words you would use to describe working with me?

And so what you can do is like, it's super simple. You just text the person and say that, then you're going to get back these words, right? And so if you do it to like, you know, six, seven, eight people, you're going to get these words back and what you're going to start to see is a, like a theme and then you combine it with a, um, I use predictive index, uh, but like a personality assessment, which it's going to do is pull out your natural hardwired strengths, right? So then help you with framing that. So you're combining this data-driven assessment, uh, with how people are seeing you, right? So those are two steps. And then the third, the third thing that I always tell people to do is after any presentation or anything that you do and someone goes, Hey John, that was great.

That was really good. And to, instead of saying, Oh, thanks. You say, Oh, that's, that's great. Thank you. I'm so glad. I would love, what did you like specifically? I'd love feedback. Um, and, and so when you do that, what you, this is, we were talking about, um, NLP the other day, right? So like I do a lot of neuroscience and positive psychology work. Uh, so what you're doing is when I, when I asked that, like, Hey, what did you, what did you like about it specifically? You're forcing them to think there, and they're going to tell you what they liked about it while your presentation was really succinct. And I love how you pulled in these different ideas and it just made me think. So what's powerful about that is you're then getting the feedback.

You're hearing what they heard, right? Because what is sales? Sales is not necessarily what, what you say. It's about what people hear. So what they heard. And then, so you're using that for, you know, you jot it down, what they valued and what you did, but then it, it embeds it in their brain. So the next time, the next time someone says, Oh, Hey, what was, you know, how was John in that session? It's like, Oh, well, his, he was super succinct and he was able to talk and he, like, you literally have it ready at hand. So these are just like different techniques you can use to sort of start to build that I call it like your leadership language. So you start to have language that is yours uniquely, that you can build upon and practice.

And then like, that's, you're just, and it's coming from you. So it's naturally authentic. Like you might not necessarily have it nailed down, but it's like, are you showing up or what people, how you want to be seen? Is that how people are seeing you? Is there alignment? So to build this confidence, right? What do you think about fake it till you make it? Because my opinions of this have changed. Um, like I think it's appropriate in some areas, but not others. What are your thoughts on kind of the bravado or the fake it until you make it to kind of pretend like, you know what the hell you're talking about, or, or you pretend like you're that confident and then it kind of leads to that. Some people believe that, um, other people say, no, don't do that.

Cause it's not authentic. So what, where do you stand on it? That's so funny. I'm like in my, my head is like, all I keep hearing is my mom, like telling me, oh, just fake it till you make it. Right. And I'm like, but I actually have, I think it depends on, it depends, right? My core value is courage. And so one of the things that I, I say, um, what, with courage means that I'm going to speak up even when I'm uncomfortable. And the other thing is if I don't know the answer, I'm going to tell you, I don't. Um, but I'm going to figure it out for you. And so for me, uh, the fake it till you make it, I, I believe that I think it's an old, it's a bit old school. Um, then again, personally, uh, because even if you're, if you're faking it, people can tell and they can tell because they're probably faking it too, exactly.

It's like, yeah, I always know, like, it's funny too, because I almost did this post to call out a few people, but I did. I called myself too. It's a, you know, when you're late for like, you forget to do something right. Or like you had a great meeting with a client and then you, you know, you, you just straight up forgot to follow up. You forgot. I love the excuses that come out. It's like, oh, I'm sorry. This was sitting in my outbox, you know, my out, my outbox folder. And I just forget to hit send or I'm sorry. I was, I, you know, but, uh, so you come up with these bullshit excuses and it's funny because there's a laundry list of like five or six that we all use. And I all know they're always bullshit when somebody uses.

Right. Right. Right. So it's kind of takes, you know, takes a bullshitter to know a bullshitter type of thing in sales. Unfortunately, there's a lot of bullshitters in sales. Well, it was funny because you were actually talking about this the other day. It's one of the most, probably the best way to get a response or get a positive, like, is to be like, this is actually what happened. Remember, because you said something about when you'd screw up when, if you screwed up what you were saying and person would usually call you back because it shows that you're real. Right. Right. Because we're all trying to act like we're perfect. And that's like part of what I talked about in the, in the talk, which was it's about comparing.

And so you're, everybody's out there trying to compare themselves to everybody else. And they're trying, you know, we're in this world that's trying to, you know, everybody's like craving to be different, but also everybody wants to fit in. But then they're like, Oh, I want to stand out. Uh, but this sort of idea of authenticity, I believe it's just that you, you are consistent how you show up. Right. And you're a learn it all. Right. So you're constantly taking in, uh, different information, uh, and really being, you know, genuinely curious. Right. Uh, yeah, it's an ongoing process. Yeah. I think your, your comment of values is where I always come back to, right? I don't think you can, I don't think you can be truly confident unless you truly know your, your values, like your absolute core values.

I'm going to give a pass to the why factor here because I just, I think I love why I love Simon Sinek and I genuinely believe in it, but I don't think it's fair to tell a 20 year old kid, like, Hey, you should know your why, like you have no way. It's good. It's kind of like the bad advice I hear people say all this. Oh, follow your passion, follow your passion. Like those are the dumbest fucking pieces of advice I've ever heard in my life. It's like, you know, if you follow, if I followed my passion, I'd be a stoner artist sitting on the sidewalk painting murals, right. And I'd be dead broke, but fall, find your passion, then follow it. Right. It's the same thing with, with, uh, with values.

I'm sorry, with, with the why, but the values, I think you can do, you can nail those down at any age, right? Oh yeah, absolutely. And so one of the things I do with the people that I, uh, I coach and train is figuring out, figuring out their, uh, what is their core value? They might be, they, they might join a company because they value the values of company, but that's not enough. We need to be very specific because what happens typically is your core value nests within the core values of the company. So there's alignment there, but until you actually drive that connection, um, it doesn't stick. So it has to be. And so one of the things about, um, the values exercise is it, it gives you specifics.

Like I think I said to you, because mine's courage. Now there's a bunch of other words that would fall under there. Authenticity, trust, connection, all the things. But if I think about the thing that I do continuously, kind of like we up and leaving my job, uh, just, uh, is courage. And so what that, and what that specifically means, because, because courage can mean different things to different people. So what we're trying to do is drill down meaning. Yeah. And if we don't have meaning to it, it doesn't matter. So we want meaning. So what does courage mean for me? Because that might be in a different, have a different distinction for you. So what that means for me is blah, blah, blah, right?

Like I'm, I'm going to be willing to say, I don't know the answer. I'm going to speak up even when I'm uncomfortable and like give a specific example of how, how, and when I do that. And what's so powerful about courage. This is a little hack that I do with people is you think about somebody you admire, right? Yep. And if you think about that person you admire and then why you admire them, what is it about what they do that you admire? And this is something that you can do at any point when you're sort of struggling with a decision. So if you think about that person, like for me, it's my mom and because she, um, you know, was courageous, started her own company when she was young. Um, and she's just all about just pushing through and being resilient.

Right. But when I think about, if you think about the person that you admire, typically there's an alignment in your, in your values. Right. So if you're like, at some point you're like, well, I don't know what to do instead of going, I don't know what to do. Say, what would that would insert person you admire do? Cool. Right. It's a really cool way to think about. So whether it's someone personally in your life or some other like leadership figure, somebody that you, um, are, that's a way to really start to, again, get a sense of, cause there's a lot of other people you don't admire. Yep. So we want to get to what is it that you like, what's this pattern, what's this sort of data we're learning about ourselves and then be drawn in that direction.

It anchors us. And if there's someone that you just do not get along with, and this usually happens a lot with team dynamic work, usually there's a complete misalignment of your values. And so when you actually understand and do each other's values and you see that my, you know, yours is courage and then this person's is, um, predictability or, you know, um, authority, I don't know. Yep. You, you start to see, oh, this makes sense, but then you can peel back and go, okay, it's not that they're just being an a-hole and you, it's just that this is what they value. Yep. So you start to understand and sort of have self-awareness and empathy of how, you know, understanding how people think. All right.

We're going to take a quick break here to highlight the HubSpot podcast network, the audio destination for business professionals. And I love listening to the podcast on this network and specifically another bite hosted by John Dick, Jory Monroe, and Ariel Bosworth. And the reason I love this one is because they focus on one of my favorite shows on television, which is Shark Tank. And what's cool about it is they take the episodes and they break them down and talk about how they can apply to our own businesses and real world application of it. You know, a lot of us, you can look at it for entertainment for that show, but what they do with another bite, they talk about how it applies to us, which I absolutely love.

And one of the episodes that they had recently was called when community is more valuable than unit economics. And this was with the magic five spike ball and you're a kayak. And they talk about magic five's value and human data and problems to scale spike balls, community building tactics and targeting issues, and also you're a kayak social proof problem and missing customer acquisition costs. So again, all super applicable to all of us in the startup world. And I absolutely love listening to their analysis and dissection of these shows. So listen to another bite, wherever you get your podcasts and keep supporting the HubSpot podcast network. Now let's get back to the conversation. Yeah. And I think with that, you could also reverse engineer it to like what you don't like.

Yep. Right. I know because that's the easy part you can look at is like, what do you have a visceral reaction to when it happens from somebody else? Well, then the opposite of that is true for your value. You got it. Absolutely. Right. So it's like, I have a problem with people being late for meetings, right? It really bothers me when you're late for a meeting. And so I look at that and I'm like, well, why is that? I'm like, well, because I think it's disrespectful because it's my time and your time. So therefore respect, you know, is a value of mine. And I can unpack that further if I wanted to, but it's a good way of looking at it as well. So. Well, and when you do that, so if respect, that's your core value, that was that like, is that not, well, it's kind of, it, it, it peels back from where mine are family first freedom, right and fair.

And I think that's, that's part of it. Earn it gratitude and creativity. Those are mine. Oh yeah. I love it. So what's so cool about it, when you do this exercise is like you learn about, you understand way more about the person and you could, and you could work with somebody for three years and not understand what, like what drives them, but this starts to not peel back, like understanding what drives them. And then from there, that's how you learn how you can motivate them. Yeah. Totally. Yeah. So let's go, let's, you, you brought it up. I'm, I want to circle back on it. You, I mean, there was a couple of inflection points in your career. Um, and, and the one that you, you just mentioned was the confidence to like literally walk away without a plan B, uh, from a pretty, um, solid job, not even solid, like later leadership, you had, you had moved up through the ranks here.

Talk us through that because I think there's a lot of people sitting in a position right now thinking, Oh my God, I, I, you know, this company doesn't align with my values, but I, I need a job and I, you know, and I'm making okay money and I got to pay my bills, but this isn't something I want to do. And I think I should change or whatever it is. So what, walk us through what got you to the point where you said, I need to make a change and bet on yourself and have the confidence to take a, take a break without even having a plan B. And well, so, and I, I had my sort of leadership burnout moment, which I talk about in the Ted talk, but that was a big, uh, that was a big aha moment for me where I shifted.

Um, I didn't leave the job right away. And I think this is what's really important for people to know is, you know, I made the decision, you know, the next job I did leave. Um, but, uh, but that the same problems and continued, um, challenges are going to follow you. If you don't think through how you're thinking about things, like, you know, you don't, you can't, you can't run away from it. It's just going to happen again in your next role. If you're not like grounded in your foundation, right. Or your, your values, who you are, how you want to be seen, not necessarily following what everybody else is doing, which is a huge thing, what you're supposed to do. Uh, but for me, it was, it was in, I had a very intentional leap from when I went from Gartner to Microsoft was because I had been a Gartner for 13 years and I had been very successful.

Uh, but, but what continued to happen was I like, I burnt out and it was because I was sort of, um, um, I, I had lost all of my, um, who I was. Right. Like I was, I was trying to like hold up the shit umbrella for like, you know, and, and, and try to like protect my team and I would continue to have, you know, successful teams. But a big part of the success I had with them was because I was focusing with each of them very specifically on what made them different, what inspired them, what, what, um, what made them, um, unique. How do they be when we, I think we talked about this. How do you be, what's interesting in you about you? That is what makes you interesting to others. But if you show up to meetings, you show up to things and you've got nothing to give.

So it became this like practice for me to sort of figure out, find my footing and figure out my why and my, like, I was, I had lost it. And I like, that's how I totally relate. Cause I, whenever I talk to people today or over the last seven years and they're this in that same position. And so it's like removing all of this stuff that you think you're supposed to do because everybody tells you, you gotta have the house or you gotta have this or you gotta do this or you gotta do that. And it's all just made up. Like we think we're, we're following this path. This is why people, uh, we, I think we talked about this. People are, you know, I was, I was successful on the outside, but I was freaking empty.

I was like done. And I'm like, this is their life. And I think that that, so that's where I had to learn these techniques to how to ground myself and then build that confidence to do what's next. So then that's what prompted me is I knew that I was going to eventually have my own business and be helping companies thrive through change and disruption. But I knew the only way to do that is if I did it. So I disrupted myself and left and went to Microsoft and went there because they were looking to reimagine their sales organization. And they were in a major, I was, it was a great learning environment for me because we completely had the biggest sales transformation ever in the history of the company while I was there.

Yeah. They like basically like took all the roles and threw them up in the air and here you go. Um, right. But one of the things that I continued to, I, I continued to notice is like, I'd sit around the room. I'll just share this to kind of funny. I would sit around the room and there would be, you know, with all the executives at these companies doing these like $50 million projects or whatever, everybody'd be like, I sell this thing. I do this thing. I sell this widget. I do this thing. And it would come to me and I'd say, well, I help you work with the, you know, get your people bought in. How do you get people bought in to where the vision of where you want to go? And then every single time the leader would be like, the leaders, people would be like, we need more of that.

We need more of that. Yeah. And, but that wasn't like, that wasn't the thing. Like nobody spoke, everybody's focusing on the technology. They're not focusing on how do you use it? How do you, how do you, um, you know, build the, um, build the buy-in? How, you know, how do you actually maximize your investments? And that's where I continue to see, well, wait a minute. Like there is a, there is a missing piece here that nobody's focusing on the people. Yeah. So it's just the, every conversation helped me build the confidence to go like, this is something that nobody's talking about and it has to come, we have to bring it back to people. Yeah. I mean, I think more now, more than ever, right. With all the automation and everything else.

Um, did you, did you have kids before or after you made that decision? Uh, no, I had kids before, before that. Okay, cool. So you ended up having, you were, had kids and you were at, you know, kind of a peak in your career doing great job. And you said, even with kids, you said, you know what, screw it. I'm, I'm going all in. Yeah. Um, I want to kind of just finish up on, on the woman confidence piece of this, because, you know, the more I, uh, you know, I mean, it's obvious, right. As, as boys, if you will, I mean, I don't know about what's happening these days, but what, you know, it was all about go, go, go. And, you know, like, and we get promoted for our aggression and our confidence and, you know, we'll show up to a job offering that's, you know, if we have 60% of the skills necessary to do the job, we're going for it.

Whereas a woman needs a hundred percent of the skills to go for it. All the job descriptions are written for men and hit the gong and we're going to crush it and all that other stuff. So, you know, it's, and then you add in kids to the, you know, to the mix. And there's just obviously, I mean, with my wife, she's got her own business and she's an entrepreneur as well, but I noticed that the, the difference in stress, if you will, when it comes to family, because there's just nothing there as, as connected as I am to my daughter. And I would, I would jump in front of a bus without even thinking about it. Right. I'm not that connected to my daughter because she didn't physically come from me. And so the guilt factor of a mom and always wanting to be around her kids and, you know, that balance and everything.

So, you know, it's a, it's, I think it's a topic for a much longer podcast, but I wanted to kind of get your perspective on kind of how we need to change focusing on the people for women right now, because it's, it's, it's challenging for everybody, but I see it. I'm, I'm hoping it's getting better because we're having the conversation out loud more often than not. But the more women I talk to, the more I hear that, you know, okay, you know, we're getting marginally better, not, you know, exponentially better. So what do we need to do to hear to keep promoting that component of, of learning and evolution here for the workforce? Yeah. Well, and is your, how old's your daughter? She's 12. Okay.

So mine's 13. So we're like in the name. Um, so the first step is defense. Like if you're, if I'm talking to the leaders, uh, we have to know is, do they really, do they really care about having a diverse Salesforce or is it because they're trying to check a box or hit a, hit a target? Do they actually care? Yes. There's all this data out there that having more diverse teams brings more profitability and reduces risk, all the things, right. Um, but fundamentally do they give a shit if they have more women or are they more comfortable with just a bunch of men? Now that's your own prerogative, but I'll tell you right now, the women, I mean, I get, I get, I'll get calls from people will be like, Hey, I'm thinking about this company.

And I'm like, Nope, don't want to go there. And so there's this whole undercurrent of, of we know the ones that are like the bro fest. And so there's a few different things about specifically about women and how they sell differently, right? Men and women sell differently. Now I'm going to say all the time, I don't want to like make it like totally gender, but, um, it's funny when I was at one point I was working and I had a team of 15 and I had two women, right. Um, and a team I had inherited. And guess who the, my boss wanted me to get rid of out of all 15 because of the way of their, well, yes, this is true story. Um, because of their, um, their lack of certainty in their pipeline and they're, uh, needing help.

Now, number one, I will tell you right now, if you have women, anybody who's listening to this and have women on their, their team, I have not done a study on this, but I'm curious if some maybe one we should do women, the way they forecast is different than men. If women, if women have, um, they for, if they have a $500,000, uh, deal on the pipeline, they're going to forecast probably 250, right? Now, if men have a $500,000 deal in the forecast, they're going to, they're going to forecast $500,000. Women are only going to forecast things if they're almost certain that it's going to happen. This is over and over and over again that I've, I've seen this. So what happens though, is in the pipeline call, well, it's like, well, by Sally, like, what do you not, you know, you don't have a growth mindset.

You're not this. No, because she wants to deliver what she's committing to. Whereas Johnny, uh, he is like, yeah, I'm going to be the one that's got the top pipeline in the, in the forecast call. Well, come the end of the quarter, who's delivering, right? So does it sound good or are you delivering? And so this is something that continuously I've observed and noticed, um, and sort of when I'm coaching male leaders on, you know, noticing these differences with the, how their women are going to, uh, going to forecast. So if you're putting that measurement on them, look holistically at actually what they're bringing in, bringing in versus what they're necessarily forecasting at the front of the beginning of the quarter.

The second thing is women are more, um, we've heard the statistic about it. There's more women on boards that they're the company's less risk averse, right? They're there. They actually perform better. And, um, did I say that right? They perform better in, um, turbulent time. So if a company has more women or a distribution of women on their board, they do better because they've been able to identify risk. Yep. Right. So what women are really, really good at is identifying risk in a deal. Makes sense. So what they'll do is up front is they'll say, hey, yeah, this seems like this might be, um, like a blocker or something. And they'll introduce it up front thinking, hey, like I have a team here that can help me.

But for a lot of the traditional leaders, what happens is they then hear that as well. Sally doesn't, you know, can't get the deal done. She needs help. Yeah. Right. Versus, hey, this is like, I'm trying to expose that this is a risk in the deal getting done this quarter. So this is a continuous thing I see, um, in differences in how women sell. So women look at it more like more, uh, and again, I'm being general here with the whole observations I've had, I've seen, uh, the majority of, um, now, so now how to change that is no, is just making aware, like even those just first two things, being aware of that as a leader, a male leader, um, or a female leader too, of the, of the females versus the males on your team, where they're coming from.

It's just naturally ingrained in women. Uh, and then the other, um, what was the other thing I was going to say? I forgot what I was going to say. That's all right. With the, so can I ask on this one that I think there's, there's blinders that men have period. I have them, um, just because of how I've grown up, how I've been treated, whatever. And it's kind of this privilege, uh, this whole privilege thing I talk about, right? Privilege isn't you, you know, uh, you, you were born with a silver spoon in your mouth. Privilege is, you know, I'm a white male that doesn't have to worry about what I dress like in the morning. And so for, for somebody like me, you know, there's, there's a, there's blind spots.

How can, you know, and I'm going to use one very specific, uh, example here, you know, asking for feedback and like, Hey, I w I, I want you to push back. I want you to ask for help. I want you to do all this stuff. Right. And to me, I say it, and I hope that that's the case. And this is both for males and females, but I want to have this more of a female, you know, considering myself, what I think is a pretty approachable person and always asking for people to come, Hey, I'm here to help whatever, but yet they don't. So what can I, what can somebody who might have blinders on do to foster a more open environment and, and, and not just say they're welcoming feedback and insights and people coming to them for help, but actually showing it so that people do.

Cause I think that's one of the bigger things. It's like, if you don't think you're good at something, if you, you know, you're afraid to go talk to your boss about it. You're afraid to go talk to leadership about it because you don't want to be seen as somebody who's not confident. You don't want to seem as somebody who's always having issues or looking for risk and that type of thing. So how do you, as a leader, open up those doors without just telling everybody you can come in my door? Right. So great question. And then I did remember what I was going to say, but I'll come back to that. It is that you, you want to, whatever behavior you want them to, to, to practice, you need to practice it as a leader.

So as a leader, like being, we talked about being like a learn it all versus a know it all. Like you're, we're all continuously learning. So taking different people from your team or even in a team meeting and saying, Hey, this is something that just came up and I'm curious. I'm kind of like, I'm kind of struggling with how I think about it. What does everybody think here? Does anybody have any ideas? So adding that in and sort of showing that you don't know it all, like you can't possibly know it all. It helps them like putting that in as a practice ongoing or noticing another thing you can do with, this is sort of like grounding where people's strengths are. So you could be like Sam, you know, Sam, you know, you, you're really, I find that you're really good at, uh, uh, sort of understanding what's going on across other industries.

Uh, you know, I've had this challenge. I'm curious what you think about it. I value your opinion. Right. So they'll, it's like follow the leader. So when you do that and you add that into a practice within your team, you're wanting to see that there's going to be more reciprocation and how they communicate back with you and ask you questions. So one more, one more question on that though. Like there's this balance of confidence that you need to inspire as a leader in you as a lead. And then there's the openness of what's going on. What's the line of transparency that a leader has to have in order to retain confidence. And there's this, there's this movie that I, I always reference as you five, four, seven with Matthew McConaughey and it's, it's about, you know, two submarines, you know, or it's American and Russian submarines and whatever.

And the Americans take over the Russian submarine, but it's a nuclear submarine. And, and all of a sudden the captain gets killed and Matthew McConaughey is the next in line. And the whole crew looks at him when the captain dies and says, what do we do? And Matthew McConaughey gives a very honest answer. He says, I have no idea. And it is the worst example of leadership in that scenario, because, because people need in, especially in times of crisis, they need confidence that a leader can get them through. But as somebody speaking from experience myself, like, I don't know what the fuck's happened. You know what I mean? Like, I have no idea what to do right now. Like I'm figuring out just like you.

So what's the line of being open and, and showing and leading by, hey, I'm open. So therefore, I want you to be open, but then being, but still instilling the confidence that you as a leader, at least are leading us in the right direction, or we have confidence that whatever you do, we're going to be following you. Hmm. Well, yeah. And now I'm like, I want to watch the movie. I don't think I've seen it. Uh, so I always think of it as like leadership, leadership, um, followership. So in every situation, there is someone, uh, you know, and I do this all the time, because like, if there's somebody in this conversation, if we start talking about like working specifically with SAS companies, uh, immediately I become the follower and you, the leader, because you've been working primarily with SAS companies, um, and sort of this idea of when you know how to shift and make everyone feel like they're a leader and a follower in your team, uh, based off of their strengths.

Now, with that said, it's about sort of going and getting your guardrails. Right. So like getting back to, I keep saying, getting back to the foundation, the basics, simplifying, what do we need to execute on by when, what is our main focus right now? You know, what are our critical priorities? How are we, you know, what are we looking to drive, um, short-term, long-term and just kind of getting back to that. Okay. Let's make sure we have our focus. And then from there, you know, embracing it for, you know, people to bring ideas in, but you're sort of creating, you know, and continuing to sort of, okay, this is the direction we're going in. This is why we're going in this direction is what we're trying to produce.

Who's got ideas? Right. Does that make sense? Yeah. Well, I mean, I think it's, it's collectively, right. I mean, it's all about focusing on strengths at the end of the day. And I'm a big fan of that. It's just, there's always that, like, you know, fake it till you make it as a leader. In some cases where you're just like, I know that right now, if I like, I am scared to death of what's happening right now in the, and I don't know the answer, but I also know that if I say that to my team, they're going to lose it. And so as much as I disagree with fake it till you make it, and I've evolved from that, I do think there might be a position from a leadership standpoint where you do have to stand up and say, find your confidence.

It's almost like giving a speech, right? Like there are certain times where you're giving a speech and you're like, I don't know what the fuck I'm talking about. I'm going to anchor on this one thing that I know I'm confident on. So let me just build it around that. And I think that's the way that you can kind of bridge the gap between fake it till you make it and not knowing what you're doing. Right. Right. Faking. I mean, I think the faking piece is not like, I don't think you're going to get anywhere with the faking, but it's sort of, it's like, uh, yeah, like leaning into the thing that, you know, you know, the direction that you, that the thing, you know, for sure. And again, this, it, it just keeps coming back to our grounding ourself and what we're doing here.

Why, you know, what we're, why we're doing it. Uh, yeah, everything is, is moving at a rapid pace and we're like taking it day by day. Um, for sure. Uh, the thing, the thing I was going to say, uh, about the, the women piece was around building confidence. So one of the most important things with women, women in sales specifically, is just being there as a support and letting them sit, know that you believe in them and then giving them the confidence that they're doing the right things, because that piece that typically is missing, uh, in sort of what women need to hear, obviously, if they're not doing a good job, like let's unpack that, but giving them the confidence that you see that they're doing a good job and that, you know, the direction that they're going in.

So instilling that, uh, in, in, you know, my husband is a coach, so he, he coaches men and women. So I've also observed this with him over the years too, uh, girls and boys, he coaches in high school. And so the way that he coaches differently men and the girls versus the boys, and it's like, I mean, kids, adults are the same as kids. Yeah. Uh, adults are just big kids. Yep. A hundred percent. Yeah. I'm still about, you know, I think probably at best 17 mentally right now. Physically is told totally different story, but maturity level definitely on the lower. Yeah. Well, and that's what we see a lot. We see, I mean, Hey, listen, go into, and this is one of the things about having kids too, is sort of, you get to re, you know, relive and re-see things in through their eyes and you're re-earning.

Right. I love, and this is sort of one of the competitive advantages I feel like parents have, you know, because they're seeing things, you know, kids have no filter and they just sort of, right. Get rid of all the BS. Exactly. All right. Well, let's, uh, let's finish up here. We're coming up on the hours. So, um, uh, Jim, where, where could people find, I know you got a lot of stuff going on. You got your Ted talk, which I highly recommend everybody take a look at it. Cause it was a really, really cool one. And congrats on that, by the way. Yeah. Uh, and you got the org and you got the everything else. So talk to me, talk to the audience about where they can find out a little bit more about what you're doing.

Yeah, absolutely. LinkedIn, LinkedIn's the place, you know, you can, uh, connect with me, send me a message. Uh, let me know, you know, what we talked about, what stood out. You can see my Ted talk there. Um, yeah, love to hear people. Perfect. And for anybody listening, it's Jamie J A I M E and, uh, D I last name D I G L I O. Go look her up on LinkedIn. Connect with her. Go listen to that Ted talk. It's actually really, really cool. Listen to it the other day, uh, before we met up. So I was glad I saw that before we actually saw each other. Yeah. But Jamie, thank you so much for coming on. It's really, really awesome talking to you. Yeah. Great to talk to you. Thanks again. Absolutely. And everybody, look, I hope you enjoyed the conversation as much as I did.

Nick, you can go out there and focus on some of those fundamentals and getting back to the basics to build your own confidence out there. And like I always say at the end of all these podcasts, no matter how bad your day's going, or you think it went, go out there and make somebody smile today. Cause, uh, if you make somebody smile, you know, you had a good day and the world needs a lot more of that right now. So thank you all very much. And I will see you on the other side. I hope you enjoyed that conversation as much as I did with your support and our incredible guests. We're one of the top sales podcasts out there right now. And I can't thank you enough now to keep the momentum going. It would mean the world to me.

If you could go and leave a five-star review on your favorite podcast platform and share some of your favorite episodes with your network. Also check out my new website at www.johnm.com where you'll find even more ways to engage. There's a ton of free content and you can also get trained from me directly as an individual or for your team. Look, I'm out there selling every day, just like you are. And I'm doing my best to stay on top of all the latest trends and technology. So if you're looking to level up and you give a shit about this profession of sales, let's connect and let's make this happen together.