Why AI Makes Self-Awareness in Leadership More Important

00:27Tolu Adebekun:Tammy, thank you so much for joining us on the podcast today. I'm

00:32Tammy Aguillon:So glad to be here and so excited that we finally made the timing work.

00:36Tolu Adebekun:Yes. And what is kind of ironic is that we were planning a podcast, then you introduced us to Kevin and we recorded with him really quickly and released his, Kevin Bailey, and then now we're doing yours. So yeah, a little bit funny. But thank you for joining.

00:50Tammy Aguillon:Yeah, absolutely.

00:52Tolu Adebekun:Rich, welcome.

00:53Richard Washington:Thank you, Tollo. Very appreciate it. Lovely to lovely to finally welcome Tammy. We're saying because it's it's really there's a lovely few links here for the podcast, like our our our three listeners, is first of all, Tammy was introduced to us by the one and only Jacob Warwick, who recently came on and did his fifth episode with us, which is unbelievable. And he's been doing amazing things out in the world, and he referred us Tammy as you a wonderful revenue leader and and human who would be a perfect person to go and have a conversation with. And we've both had pre-chats and gotten to know Tammy. And then you've obviously introduced us to Kevin Bailey at Dream Fuel, someone that you found, I'm sure we'll talk about on this podcast. I've then had a bit of coaching from Dream Fuel. It's already changed my life. So Tammy's already changed my life. And and I'm just really fascinated to learn a bit more about the career story of this wonderful human who's been on a journey to get to an incredible level in her career. And also very high sort of status that most people aspirationally would love to get to, but you're a human being like all of us and you've been on a journey. So understanding some of those big decisions, the bets, decisions that you made along the way, I think will be really fascinating. and just get your take on what you're seeing in the market as well.

02:05Tammy Aguillon:Would love that. Where should we start?

02:08Tolu Adebekun:We'll start where we always start, Tammy. what makes you tick? Oh

02:12Tammy Aguillon:Gosh. I knew just from listening to Past Cause that's where we're gonna start. And I was like, how do I How do I make this sort of like, you know, something really clean and packaged that I can just deliver in a soundbite? I think I've through some of my sessions, but also just through my own self-journey, I have a pretty strong sense of self-awareness. what makes me tick is I like doing hard things. It doesn't mean that I always like doing them in the moment. It doesn't mean that in the moment as we're doing them, that I am loving every second of it. But as I look through, as I look back just sort of like through my own career and life journey, the hard stuff has always been the stuff that has been defining and the most rewarding. So I think you know, and as I as I also reflect back, I realize that a lot of that has also just been chasing achievement, chasing goal, chasing goals. And that's how I used to sort of like define what makes me tick. It's like I gotta climb the next mountain. But really I think it's really just about like overcoming hard things. And the good the good news is that in corporate and in tech, there's no shortage of those things. No shortage.

03:21Tolu Adebekun:Would you be open to sharing one of the recent hard things that you've overcome?

03:25Tammy Aguillon:Yeah. I would say, you know, like I even just sharing like my own career journey, and this was very recent, and I I think what I've realized is the shoulds, the shoulds. and I always remind myself even of that now, is I'm not gonna do anything because I should. And I fortunately know myself enough and trust myself enough at this time where I know how to sort of like gut chuck j got check and head check myself on any sort of shoulds that I that I hear floating around. And it was a really hard decision to sort of like, is this the right thing? Is this the right time? And decide to make a move and certainly decide to make a move into a startup environment. Right. And I knew that was going to be a hard thing. I knew it was going to be a risky thing. We're still in it. We're still in it. And so far it's been it's been a tremendous experience. but I think for me, the way I always think about this is like if I can't do hard things, how am I gonna lead and coach other people to do hard things too?

04:29Richard Washington:I'm really fascinated to understand a bit about the how you you stopped doing shoulds. I know we we had a podcast probably a couple of years ago now, Tolly with Finley Clark from Google and a few other companies. And he talked about how he had some coaching where a coach told him that his head, his heart and his gut had to be in alignment around a decision. Yeah. But what does it mean for you and how have you figured out how to stop? Which I guess most people struggle with, particularly when they ask their loved ones and closest, you know. Trusted people for advice, everyone hits them with their version of what you should do, which is even more compelling sometimes. So, what what have you learned?

05:04Tammy Aguillon:What I so the thing that I ha I'm very, very, very blessed to have a very good support system, both professionally and personally. And so I know that even if I ask folks for like a what do you think question, everyone's always gonna have my best interests at heart. But yes, to your point, like they are gonna have their own bias around it. And so one thing that I've really sort of like picked up on over the years is I take the advice, I listen, but always with a grain of salt. And I think that's a wonderful way that Finley put it, which is like head, heart and mind. That's I mean, in a sense, like I think that's essentially what I do. And when I've overly listened to just my head and it just sort of like circles and it loops, that's when I know now, not always, but that's when I know now that it's not always the best thing for me. And I will feel it. I will feel it in my heart. I will feel it in my in my gut. I I know now that it's if I just listen to the shoulds and the voices in my head and folks telling me sort of like giving me external validation around it, it's not always gonna work out my way. It's it's not it's not done. The the work is still there, Richard. You know, like every day there are still things it's like I should do this. And I I, you know, also there's other decisions related to work and my team where it's like it's not about me. And that's the other thing that I take off of the table too, which is like it's not about my ego. So the should around it, it just takes another it just takes another variable off the table.

06:26Richard Washington:This is fascinating. You mentioned gut check. I wonder what that means for you.

06:32Tammy Aguillon:I I it's a visceral thing. It's a visceral thing. I can easily say that it's not always logical. That's what this is for and helps me through it too. But it's quite it's physiological. Quite literally, it's physiological. I can feel just like a sense of unease or I can feel it just feels not at peace. and I I've just learned to listen to that. And every time in the past, when I haven't listened to it, things just haven't gone the way that I've hoped they've gone. It's not it's not like a foresight or like fortune telling sort of thing. It's just like a it's right there in the moment. Is this right or is this not right?

07:12Richard Washington:Yeah, I love that. I can definitely definitely relate to those things. Just sometimes it's people, sometimes it's situations, sometimes it's places, sometimes it's decisions, but you you you feel it. Yeah. And and often it's hard to put that into words. Yeah, it really is. But you you do have a physical reaction. I think it is worth listening to it. Yeah. Really really fascinating fascinating.

07:34Tammy Aguillon:I was I was chatting with a friend the other day, a really good friend, and she, you know, she mentioned she's also she's like looking for her next her next role. and she's been incredibly successful, very, very successful CRO. and she told me, you know, the next thing I'm looking for, I'm gonna base it on vibes. It's gonna be based on energy because our mind doesn't always lead us exactly in the right way. And I was like, I get it. And she has a track record to prove it. and so I'm I'm very hopeful for her. I know she's gonna find the right thing, but I think if more people trusted their gut, just you know, I know it's all like people talk about pattern recognition and I know what this, this, and this looks like, but at the end of the day, to your point, we're all human. And those of us who know ourselves, like and can and lead ourselves and know our own journeys and know our own paths can help lead our own selves forward too.

08:27Tolu Adebekun:And and I think that's where often we see them as kind of opposites, right? Like either I go with the data or I kind of trust my gut. But it's almost like back to that alignment thing. Yes, you can absolutely have all the data and understand that, but you still like you still have to have the gut thing right as well. Because everything can look right on the surface. But you don't know that actually maybe that dynamic's not going to be right or this is like you just don't know, but your gut kind of knows. So yeah, they don't have to be, you know, they don't have to be opposing. They should be working together.

08:55Tammy Aguillon:That's that's why we interview too, right? Because everybody can look perfect on a resume or everyone can have a have have a beautiful LinkedIn profile. But that's why you talk to people and you talk to them multiple times and you have other people talk to them too, and you assess against a rubric or some sort of metrics-based hiring profiles because that matters. That matters. Otherwise we would just hire people based on LinkedIn profiles.

09:20Tolu Adebekun:And it also goes the other way too, right? Sometimes the C V might not be exactly what you think you're looking for, but you talk to the person, you're like, "Oh my gosh, like this is the person we need, you know?

09:30Tammy Aguillon:That's right. Absolutely. And that's that's gonna continue to evolve going forward too. Yeah.

09:37Richard Washington:Yeah. And and hopefully not not too many people or companies outsource their decision making to AI.

09:44Tammy Aguillon:Hopefully not. Hopefully not. Data data AI is great at providing data, data packs, analysis, but if that's your end all be all the how you're making decisions and and is what centers your decision framework, that can be that can be very misleading. because

09:59Richard Washington:It's there almost like that naivety part of AI, right? Like if I don't know much about a subject and I ask AI, it's very confidently tells me some things, you know, and tells you like almost what to go and do. And you go, "Oh, that sounds great, and you go and do it. But if you have experience of it, you go you call out the BS, you understand the blind spots, you know when it's hallucinating, all that stuff. and it the stuff that it doesn't pick up that's really important. On people that's really important because we're talking about nonverbal signs and the vibes and the energy and all those gut checks. I I wonder Because if we talk about gut check, my brain goes, how much of that is like instinct, based on like a sort of fundamental understanding of how it aligns to your core values versus it's triggering the patterns that we've experienced that we collect during our career. So like our gut grows stronger over time because it's based on past experiences. I wonder if you've got a take on instinct versus experience as it relates to gut decisions.

10:55Tammy Aguillon:I absolutely believe it's both. because if you don't have the experience, you won't have developed the instinct for right or wrong or what's worked for you in the past. And you'll just look to either AI to help you make your decisions or you'll look to other people. Right. So I I think the the experience part of it has everything to do. Like I there's no way I would have developed my gut or my instinct if I hadn't had both good and pat good good and negative past experiences to be able to support me through. Current and future decision making. I but yeah, I and then, you know, then then you have other folks who are like extremely data driven and that's all that they consider. But that's easier to do when you're looking at some sort of like work-related spreadsheet or some sort of work like in the moment related problem that you're trying to solve. But when it comes to like big decisions, like what you're gonna do with your career, what or if you're gonna make a significant pivot. there's there's gotta be some element of like past experience and instinct that will help guide you too. And I mean that's the energy that people talk about. Like they're like my energy spikes when I'm doing X, Y, and Z, when I'm coaching somebody. My energy dips when I'm just behind a Zoom all day and I need to be out and about with people. Like that's taking that understanding of yourself is is really critical.

12:09Tolu Adebekun:That's so interesting 'cause I would have actually personally I would have put experience in the data camp almost. So I think, okay, I've done this ten times, so I've got a bit of data, but it's really interesting that you've put it as kind of instinct can be developed almost as well by experience. So that's that's a really interesting take.

12:25Tammy Aguillon:Yeah. That's how it's worked for me at least.

12:29Richard Washington:There's a there's a book here on my bookshelf called Love and Work by Marcus Buckingham. I'm not sure if you've read it yet, Tammy. We'll send you a copy. We'll send you a copy. I'm not sponsored by Marcus, but he's an amazing book. In that book, he talks about something that you triggered, which is he talks about in our life we have red threads and grey threads. So it's very much based around like the Mihai Chick sent Mihai flow principle. And so red threads are things that you naturally volunteer for. As you're doing them, time runs away. And afterwards you feel energized. And it can be people, locations, activities, and jobs. So particularly in this context, he's talking about where you find love in work. You are it's full of activities that give you your red threads. But over a career, we build up a lot of things that we're very capable of doing that we are very good at. We can even get paid for them, but they're gray threads. And how he describes gray threads is we procrastinate over them. Yeah. before we do them. When we're doing them, time drags and afterwards we feel drained. And I just wonder in your career, what have you learned are your red threads? Oh

13:40Tammy Aguillon:Gosh, so many of them. you know, I feel very fortunate to be in the role that I'm in. And that is in and of itself hasn't been an easy journey either. but the red threads that I always I'm gonna use that analogy. The red threads that I always pull on, I have I have a truly like I really enjoy coaching and developing folks. For me, it really is about teamwork. you know, one of my past Bosses, shout out Enrique mentor, is that English was his second language. And he was like one of the first English words that he learned that he truly loves us together. And I've really embraced that because I think that was always something in undercurrent for me, which is like developing and coaching people, but winning together and doing hard things together and having a sense of community. Both those things drive me in a really intense way, which is why I think like sort of like the nature of sales and Even sales leadership, like that's the nature of what you're doing. We are always working in unison. And I don't even just mean like AEs and sales managers, but I mean like solution engineers, revenue operations, enablement, just all of these different fun finance, deal legal, like all of these different functions together. And if you're in the right environment, that can that it can it can be it can be really fun, even when you're not always winning. it can be really satisfying and really rewarding, at least for me, to to be part of this community and to be running at the same thing. And that's not always the case, right? That's always that's not always the case depending on what company you're in. sometimes that's defined as quote unquote culture. but for me, that's something that I've always sought out.

15:23Tolu Adebekun:How how did you end up on the your sales journey? How did you end up in sales?

15:27Tammy Aguillon:In a very meandering way and certainly in the beginning without intention. So I grew up in an immigrant household. My parents, my dad was a hardware engineer, my mom was a pharmacist, so also very STEM-based roles that I was exposed to. sales was not any sort of and certainly tech sales was not on either of their radars. and so when I, you know, graduated from school, I sort of went into like a marketing role at a tech company. At the time. And it was fun. It was fun for like a few years. did events, did PR, did sort of like a bunch, like did site, created the website, did like some sales support materials, and that was like my first exposure into the world of sales, interviewing a bunch of salespeople. certainly had just never crossed my mind that that might be something interesting for me. Also, because I just didn't have any role models. and there was also just a certain type of like persona that I associated with being in sales, and I did not self-identify with that persona. so it just wasn't on the radar. Eventually I reached a point, you know, I'll call it like my quarter life crisis, where it's like, well, is this is this really what I want to continue doing? Do I really want to continue down the marketing path? It's been fun, but I don't know if it's really ultimately what I want to do long term. a very good friend of mine said, you know, you have the personality of like somebody who could potentially do in your disposition, somebody who could really do well in sales. Almost took it like as an insult at the time. Again, like I was I what do you mean?

16:58Tammy Aguillon:Like I'm not, you know, I don't like to talk about money and you know, like I don't like I certainly don't like to ask for money or ask for things. I don't know why you would associate that with me. but I ended up shadowing. she invited me to her company and I shadowed her company for a day. And it was again, I think one of those like I wouldn't say it like changed my my my life, but certainly changed my view on what it could be. And I firsthand watched her as she was coaching people on the sales floor. And I was like, that's really interesting. The other part, I'll have to learn. and again, it wasn't like a I set out to do this, but then I just started, you know, applying at the time there was still people were still applying for jobs and it actually worked. And got myself into an SDR role. So I went from sort of like A mid-level marketing role started over completely as an SDR cold calling. and actually I was so green at the time that they wouldn't, I it wasn't technically an SDR like outbound calling role. It was the inbound SDR role where the hello at company.com and the if anyone called the company number, that was me, like answering the sales calls and answering sales emails. So I started as like an inbound SDR and then eventually moved into an outbound SDR role. And it was a lot of fun. What it really did for me is it exposed me to the whole like just working directly with an AE, sending leads, working with this the sales manager of that AE and seeing how that sales manager coached that AE and gave me a glimpse into that world.

18:37Tammy Aguillon:And that's when I was like, I can do that. I can do that. It's gonna be really hard and it's gonna be like unlike anything that I've done before, but I'm just gonna try it. I'm just gonna try it. You know, also like from a life stage standpoint, had a really low risk profile at the time where I was like, I'll just try it for a year and see how it goes. And if I don't like it, I can always go back into marketing or do something else again. So I think there was there was that naivete at the time that sort of was like, let's just do it. But that's also like what got me started and just haven't looked back since. Once I I rolled into the AE role, it was like like I had always it wasn't like I said, certainly wasn't easy, but I felt like this was the thing that I had been searching for.

19:22Tolu Adebekun:It it sounds like some of the coaching and some of the leadership aspect was something you were really looking forward to. When you got to that stage where you jumped from kind of IC to being a leader, was it what you expected or was it quite different? Oh,

19:35Tammy Aguillon:It was very different. I think I had this romanticized version of what it meant to be a sales leader. And and actually, by the time I was tapped for leadership role, I had been in the IC role, in an IE, I C AE role for about three to four years. And I was doing well and I was doing fine and I was independent and I was autonomous. At that point, I actually was not even thinking about leadership anymore because I just was like cruising. and then when the opportunity came up, I really had to think about it. Like I really had to consider and it was not like a yes, this is the thing that I've been waiting for. It was like a I, you know, things are good. Thing like this is I'm gonna have other people's destinies now in my hands versus like just being able to control my own day-to-day. And so there was a lot of consideration that went into it. And I same thing. I was like, you know what, I know this is gonna be challenging, but this these these types of opportunities don't come up very often. and I had worked from being in BDR to an SDR to an AE, and I was like, this is the natural next jump. I did feel a little bit of that I should in the beginning, but it was also like coupled with an excitement of like, no, I want to, like, I want to take on this challenge. and it was very hard. It rocked me. I would say like that first six to nine months as a sales manager, first time first line sales manager forecasting was really difficult because I didn't trust the sort of like framework that everybody else had. And so I had to learn how to set up a framework so that we were all forecasting the same way.

21:06Tammy Aguillon:Even just how deals were run. You know, again, I had like my own sort of methodology and my own art and science to how I ran deals and being able to sort of like be open to other folks' ideas. It was, it was jarring in that first six to nine months. And even now when I have folks come to me who are looking to make that jump or they're looking to make a jump from like first to second line or even second to third. There is always just like there's gonna be a lot of what you've become accustomed to and know, but taking it to a different altitude. So I think for me that first that first six to nine months, I'll I'll always remember it. And I have a lot of empathy for folks that are making that move too.

21:41Richard Washington:What's the biggest jump you feel that you've ever made in terms of how difficult it was to go from one level to be competent at the next?

21:52Tammy Aguillon:Actually, I would so I've gone from first to second, to third, currently have a third line role too. I would say truly the fur the hardest thing was going from IC into leadership because not only is it supporting others, but it is also like you represent a different side of the company now. So not only are you looking out for the best interest of the customer, the AE, but you are also looking out for the best interest of what's right for the company. And that's that's a different dimension to take on too.

22:25Tolu Adebekun:There's also a lot more that you can't necessarily talk to everybody about. 'Cause I think when you're all ICs there's a level of, you know, we can be really open, but yeah, but once you go to the leadership, you're a little bit kind of us versus them a little bit. There's a little bit of a dynamic. There's stuff coming from above that you can't always pass down to your team. So it's a really it's a really big shift.

22:42Tammy Aguillon:That's right. There is a there's like a I I wouldn't call it a shielding, but there's like a buffering aspect to it, which is like you have to be able to really effectively filter what's coming from the top and be able to translate in a way that's gonna support the team and not exert downward pressure. But look, not everyone thinks about it that way too, because I've also just been a part of organizations where the pressure Yeah, just So it's just a different bar that people will hold leadership to.

23:10Richard Washington:I wonder about the this step from first to second to third. we skipped over it so quickly. And I and I just wonder like, what was it that was the fundamental driving force within you that made you continue to push when a lot of people do get settled into a certain level, or a certain level of comfort or a certain level of earning and the risk of going higher or what that would mean in terms of the workload or the expectations or the pressure or whatever, what was that fundamental driving force that has continued to propel you up through the through the ranks?

23:48Tammy Aguillon:For me, I I don't want to put it as, you know, having a seat at the table and just having a voice for the sake of just having a voice. For me, there's genuine interest in wanting to understand the company and understand the business at a more operational level. and I think like if if folks aren't interested in that and you like your day to day and you like running the deals and you like running a team, that is exactly where you should be. but if you have an interest towards looking into like helping the company and more strategy like just overseeing the business in a different sort of purview, that's certainly something to consider, right? That's the thing I would encourage people to do. You shouldn't force it. Again, it shouldn't be a should thing, but you know, and also some people sort of have a gift for it where they're already leaning that way in their current role. That's something that I would actively encourage people to look at and do. But for me, that's been the driving force, which is I can see all these patterns, patterns. I can see all these things happening across my team, across my peers teams. I really want to find a way to be able to bring these together. And sometimes, you know, fortunately, Sasha, unfortunately, it just requires stepping into a certain title or certain role at a company.

24:55Richard Washington:Yeah. Yeah. 'cause it's interesting because you talk about like you know, your love your love of coaching. There's obviously this clear sort of pattern we're seeing around wanting to do hard things and take on new challenges, but also just a very deep curiosity Yes. to want to understand and then and then impact it. And I just I wonder in your in your mind, like how do you think about that? Because obviously we talk about hiring for curiosity. We know it's something that businesses love to talk about, but in in your experience, what does that curiosity really mean in real life?

25:23Tammy Aguillon:I am and I and I share this very openly, I am highly optimized for learning. which is why when I even like think about career decisions, roles, there's always got to be the element of like, okay, I can help and I can make an impact because I've done the thing before, or I've seen it somewhere else. But for me, it's really about like looking for the thing I haven't done before because that is where the learning edge is gonna take place and that will what makes That is what's going to make it interesting and continue to make it interesting for me. So you're right. Like you pegged that exactly right, which is like there's just this intense curiosity that I have. And it's it's very much around this idea of learning. and it's not just for the learning sake of like career advancement. I just for me, that's what keeps the day-to-day interesting. And there are always, again, there's no shortage of things to learn, and certainly in this new age that we're entering into as well. Like, not just The market, the industry, but just a new way of working altogether.

26:22Tolu Adebekun:Is is there an approach that you have for doing the hard thing or doing the new thing? So, you know, when you're going into an environment where you know that, okay, I don't have that experience, what's your approach to that? oh

26:33Tammy Aguillon:This I was just talking about this with some with a peer yesterday too. it's you know, there's that, there's that, there's this parable of like the elephant and taking a bite of the elephant, like one bite, it's it's kind of a weird one. But I think about like when you walk into something, especially when you're new or when there's like companies are going through changes or there's always this like huge looming thing that you're trying to solve, or multiple looming things that you're trying to solve. For me, what I've also seen is like people get paralyzed by it. Like many people do, right? You get sort of stuck in this state of like paralysis. And it's like, where do I start? Where do I begin? What's the thing that I tackle first? Is this the priority? Is that the priority? And for me, it really is about you you do sort of have to go through a prioritization exercise. Otherwise, you end up doing all the things and you do all the things not well. my approach has always been to chunk it out. So identify the things first and stack rank them. Then If that is a if it's a big one and it's a big one that requires multiple steps, requires multiple stakeholders, you chunk it out into different steps. I mean, it's sort of like part of it is just the way like sales works too, right? Like a sales cycle. Like if you're trying to pers if you're pursuing a very large enterprise customer, Fortune 50, Fortune 10 customer, that's not gonna be done. We all know that that those are like long sales cycles, but there are micro wins along the way of actually winning the deal. Same thing when you're tackling something hard within a company. There are micro steps and wins that you can take on along the way while you're trying to solve this problem.

28:07Tammy Aguillon:And bring people along with you along the way. Again, the together and team aspect of it. You're not certainly not gonna be able to win alone as an exec.

28:18Richard Washington:I was going to ask you about that because what we're seeing a lot in the market from a talent perspective is businesses making large cuts to team blame. I say blaming the the rationale for that is that AI is being used more. So they don't need so many staff. Maybe there's a massive investment into developing AI products, maybe the business model's changing, but AI is causing disruption of workforce. And we all see the rise of, you know. AI SDRs and the promise of AI lead generation, fixing all of our pipeline worries, all that wonderful stuff. which is, I think, causing a lot of people, particularly at the breaking into tech and kind of like IC level, to be pretty concerned about what the future looks like. And you've mentioned about the role of a leader being to bring people on the journey with you, which I I love how you've described that, because it's exactly how I think about it, which is probably why I love it. But it's because what I've learned is AI will tell you everything and it will like help you make decisions. But we all know how to be fit. We all know how to be healthy. We all know we know it. But we don't do it. And it's because we've be told what to do, we just naturally like resist it. and knowledge isn't like result. There's a massive gap in between, which is like someone actually wanting to go and do it, or maybe like breaking through the barriers they've got or or breaking through a blind spot. And I just I wonder like when I'm talking about those kind of topics around the impact of AI, but also about the role of leaders moving forward, what comes to mind? Oh,

29:52Tammy Aguillon:You touched on a few things there. I first of all, I just want to comment on the you know you need to be doing certain things. Like I've I'm intimately familiar with that, and I call it the knowing doing gap. which there's also a book written around that too, which is yeah, we all know the things to do, but doing them and doing them regularly and consistently is a is a different thing altogether. I would say like AI is very good at the knowledge piece of it. Sure, you can set up an agent to help you do the Doing part of it. But again, the discernment between the knowing that there's like a third element, which is like the discernment of like a should you, right? Is this the right thing to do? And it maybe it was for six months, but perhaps it's not the right thing to continue doing, is is a different thing altogether. I would also say, like, going back to sort of like your your point, Richard, around like how do we, how do we think about this in the context of like teams that are expanding, teams that are You know, downsizing. The thing is, is like AI is such a panacea right now. To your point, like it's whether the business model is changing, whether it is replacing people quite literally with AI, it is gaining efficiency with AI. I think where I'm starting and this is a glimpse, this is just a glimpse, and I'm hoping it's a glimpse of a trend to come, is using AI not just to cut and to gain efficiency, but using AI to expand. Like, can we use AI to expand? And and people are already doing this, right? They're helping to like. Streamline their go to market model. And yes, sometimes that might mean like AI SDRs versus human SDRs, but also like using it to ideate on like pricing and packaging changes.

31:29Tammy Aguillon:Can you use it to minimize the number of tools and workspaces that your AEs and your reps have to go to? Right. Doesn't mean you're cutting back on the number of teams, but you're helping or the number of people in your team, but you're helping them to become more efficient. Like I I'm starting to see more of that. And I hope that trend continues, but I think that's really where people are going to gain the most value is using AI as a thought partner to volley back and forth like ways in which you can use your existing team and either up-level and upskill them or make them more efficient in the way that they are now.

32:01Tolu Adebekun:I I wanted to ask, as you kind of look to the future with all the changes that are coming, what is the the hard thing that you see coming that you're starting to prepare for? And how are you kind of on that learning point? What are you learning at the moment to prepare for for what's to come?

32:16Tammy Aguillon:I think like in the most immediate sense, there is still a lot of different types of tooling, right? Like I sit on Fender calls, I listen to podcasts and talk to peers about what their tech stack looks like. Where does I AI fit in? What is just an AI wrapper that eventually I can just use an LLM for? I think that's sort of the thing. And again, that's short term, like 2026, 2027, is figuring out how all of the tech stack and tooling comes together so that we can do that. And I and then part of that is also related to the workflows, right? Like which part do we want AI playing a role in? And then which part do we actually want our human brains to be the human in the loop and be able to to propose you know, adjudicate any judgment against it? I would say like as a profession, you know, as a more sort of existential like meta topic going forward, it's it's really hard to say. I think there used to be this this sort of like concept where I would hear people talking about like, well, yeah, like maybe you know, enterprise will enterprise selling will be more difficult to replace. Maybe that's true. Maybe that's true. I think that's probably true for the most part. but I think, and we're already seeing this now, a lot of that early buying period or early evaluation period, they're they're already using LLMs. They're using community threads to do that. A lot like it used to we already said this like 10 plus years ago, which is like By the time your buyer comes to you, they're already 60% of the way through their buying journey. I think it's gonna be closer to like 80 or 90 by this point, right?

33:52Tammy Aguillon:Even for enterprise selling. And I think where enterprise selling is really gonna come in is gonna be that last mile of like negotiating contract terms, really digging into the product more to make sure that there's like security and compliance and everything that like a large enterprise company would need. But it's really gonna be like on that forward-deployed side.

34:13Tolu Adebekun:Yeah. It's really be on that forward deployed side.

34:16Richard Washington:Yeah. I wonder what you think about the pipe gen side. Because it's one of the big like you can't open your inbox or anywhere without seeing someone promising that AI will just, you know, flood your sales team with perfect ICP leads all day, every day. I wonder like how you see the role of humans within the pipe gen part of of prospect of you know business development.

34:38Tammy Aguillon:This is, I feel like this is going to be one of those controversial takes. I for now I still see the role of humans playing an important role. mainly because like if you're trying to achieve both scale and personalization, I just haven't seen AI come through in a way that's been very effective. Yeah, Maybe someone's cracked it, but I haven't seen like, you know, exciting examples of folks who have been saying like this is this, like we've cracked the formula. Because the hard part is that whatever works is usually fleeting. is what I've usually seen, right? And I've heard this from my peers. we've seen it ourselves. Like everything that works does until it doesn't. And then it's on to the next thing. You know, for we all remember this. Like in real life events, they're back. Like, and for a long time they weren't, right? People weren't leaving. People forgot how to talk to people in real life and forgot to have a like how to have a an actual real life conversation. And now IRL is it. I mean, I personally love in real life events and the opportunity to be able to go out and see people in person.

35:39Richard Washington:Yeah. how much of your your sales team's time is is belly to belly selling. So how much how much of a a pro how much

35:49Tammy Aguillon:I haven't heard that one. Is that an English?

35:52Tolu Adebekun:I don't want to hear that ever again. I like it. I like it.

35:55Tammy Aguillon:Is that a Richard term or an English term? Okay, Tulu's laughing, so it must not be an English term.

35:59Tolu Adebekun:That's not English.

35:59Richard Washington:I often I often say these things to to he laughs. He laughs. But I heard it the other day and I was like, I really like the term. I'm gonna use it in real life from now on. But but whe where do your sales team get get the most effective result from relationship, from belly to belly selling?

36:21Tammy Aguillon:Yeah, it is. I mean, it's it's it's gonna sound it's exactly what I just said. We see the most effective cycles being run when there is some element of an on-site and face-to-face interaction. So that is a huge priority for us to get people on site, doing meetings, events, dinners, all and this is not just for customers, but it's also for partners too, right? Especially if you have a really thriving and big community and and partner ecosystem like It applies across both worlds. so I it is it is it is like we're we're seeing like a there's like a four X multiplier on our win rate whenever we see people getting out and meeting people in person.

37:01Richard Washington:Interesting. We had Brent Adamson on the podcast the other day and he was talking about how one of the big things was his like the whole challenger thing Yes. that he's come up with a new framework now around frame making, which is about building customer confidence rather than necessarily challenging their worldview the whole time. And obviously in the challenger model, relationship sellers were some of the least effective. And I just wonder your take on how much you care about. people's ability to build relationships and be a relationship type salesperson as part of the criteria of what you hire for.

37:36Tammy Aguillon:Yeah, I I am that's very cool that you had Brent on. I loved the Challenger methodology and challenger selling methodology. I've also, you know, we've also done force management, medpick for qualification, very familiar with value selling and Sandler. The thing is, I think, I mean, Challenger is it's effective, but I also think it's a bit of a misnomer for me. The way that I've always interpreted Challenger is it's not necessarily just like, challenging them so that you can be right, right? Or like it's the whole idea behind it. Again, I'll go back to it's it's about teaching. And that's one of the three principles of Challenger, which is like commercial teaching. And for me, the way it's less about just playing golf or like being a buddy with a customer. It's really about like, hey, every time they have an interaction with you, are they taking something away and learning something besides the product and what it does? Are you giving them insight? Like that's certainly what interests for me. And that's partly because like Like I said before, an optimized for learning and I'm highly curious. So if someone is going to give me insights and things that I didn't previously know, I find that valuable. And I think many people do, right? We're all sort of like in our day-to-day worlds, like stuck in our, in our Zooms and in our company four walls. Anytime someone is able to maybe not challenge, but give me a new perspective and teach me something, that always lends value. And that's that's very much like, the way I see challenger selling is it's always coming with the point of view, whether it's right or wrong.

39:02Richard Washington:I wonder if that's what people saw within you at that very early stage when you to you know took offense to people saying that you'd be a good salesperson. Cause there's the very charismatic salespeople and then there's the maybe more like introverted type personalities who are like highly intelligent, who really take the time to study sharp, well prepared and and teach tailor take control, all that good stuff more naturally than someone who just relies on my relationships, my black book, I go golfing with these people. La

39:30Tammy Aguillon:Absolutely. That was that was like yes, that was the old school way of like what we all thought sales was and certainly tech sales.

39:38Richard Washington:Yeah. exactly. So is that how important? Do you think that that's because it's how you were very successful as a salesperson is because you you did have this much more like intellectual I want to show up with value, I want to do a great job in this process. Do you think it that's how you were successful what's your take?

39:57Tammy Aguillon:Yeah, I think it was that. I think it was like I I want to show up and not just talk about my product. I want to have more of a conversation around the industry. And also that's what's interesting for me too. the second thing was so when I was in marketing, I was essentially like a project manager. And I found that to be highly valuable when I moved into being an AE, which is like there's a beginning and there is an end to their evaluation. And I am going to support them along the way by hitting milestones. And if they pass a date that they were supposed to that they were supposed to take an action on, I'm gonna remind them that we were gonna have a decision on that date and that these were all the steps that led up to their decision date. I just for lack of honestly, like lack of early sales training, I just relied on it being and thinking of it as a project as a project that had a beginning and an end and helping them along that way. And then yeah, I was consulting with them along the way too. That's sort of how I thought about my job too. I'm my job is to help them make the best decision. So I would say like those two aspects are what really helped me in those early days. And even now, like I see the best reps that I work with and I've worked with literally hundreds over the course of my career. Even if they don't think about it that way, I've seen them run deals that way.

41:13Richard Washington:Yeah, exactly. And the ones who don't typically get stuck because they just can't handle the next level of complexity or or or volume or or you know, importance. That makes sense. I wanna talk about the So I'd love to talk about the the mental side. I know we've had a lot of talks offline. You always introduce us to Kevin Bailey from Dream Fuel. So you you take a lot of interest in this topic and then you've gone and sought out help and now you're sharing that with your team, with me, with with lots of people. Why do you care so much about the mental side of the profession of leadership and sales?

41:45Tammy Aguillon:Yeah, I I think I well, I I took sort of like a personal interest in this because I think again, it just behooves all of us as humans to be able to sort of like elevate our own thinking. And I just have, like I said, had a personal interest around the topic of neuroscience. why is it so important for us as leaders? Because we are we have teams under our purview. We are making important decisions for the company, we're making important directional decisions for the business, and very often with Imperfect data with shallow level analysis that we may or may not be getting. and we're making decisions with uncertainty every single day. All of us are. AI can help and can and and is outpacing us intellectually and in many, in many cases, cognitively, right? It can solve many of those sort of like analytical problems that we might not been have been able to. But what Helps us and remain human and to lead human teams is to support people who need a little bit of support when it comes to their own performance. And for me, you know, I shared this earlier, which is it's if you don't have your own mental state and your own nervous system under control, or at least like under some sort of state, it's really difficult to help lead a team if you're constantly context switching, if you're not able to get your own regulated. nervous system under control. If your emotions are wildly switching from one minute to the next, like there's it's very difficult for you to be able to bring your best self into your company and certainly to help lead a team through that too. And even showing up for your cross functional peers. So you know, I think and and I think like even just being able, like I shared with you before, like this sort of like new skill that I've been able to develop, which is around sort of like this metacognition state and being able to like and analyze my own thoughts from a third party perspective has been game changing.

43:43Tammy Aguillon:And it's it's one that I think a lot of leaders can and should look into and benefit from. I myself have seen a ton of improvement around it. But I also think like again, in the age of AI, things are gonna keep, they're only gonna get more advanced. And with in the state that AI is right now and in the in the in the way that it's gonna continue to advance, the models are only going to get smarter. The only way that we can really keep up even with the pace of it is to help center ourselves. Although I think there's speed and pacing part of it too.

44:16Richard Washington:What do you mean by that?

44:18Tammy Aguillon:It's just the advent of how quickly AI has moved. and it means that we are still running to catch up to it. Yeah, We're still running to to catch up to it, to even see how we can work with it, how we can mold it, how we can bend it. It requires a new way of working. It requires a fundamentally completely different shift than all of us in tech were doing, even just like two years ago. And it can be, you know, while you're trying to balance all the other things, like I mentioned before, decisions, company, forecast calls, pipe pipeline generation and figuring all of that out too. Like that's that's really where having a centered mind and centered nervous system can really help with just sort of like capturing and and just just sort of like settling the day to day so that you can make good, smart decisions.

45:11Richard Washington:You said something about like AI being a thought partner and also about like, you know, being being centered in terms of your decision making. And what my session with Dream Fuel showed me was that when I hadn't been before I started that, I'd been getting frustrated and I'd start to lose some of the creativity and some of the problems felt bigger. And so my ability to think clearly and therefore like what I did next and the results that I were getting, I wasn't really happy with. And as soon as I started to like practice some of this stuff and reflect on it, my creativity flooded back and my thinking became clearer. And like if you've got this tool which is AI, which is a thinking partner, if our thinking's not right and we're not creative, the questions we ask, like what we ask it to go and do, will be poor. But if we've got this amazing tool, it's like and we're coming to it with great intentions, great questions, great thoughts, it can like massively accelerate those things. I just wonder what your take is on on that.

46:03Tammy Aguillon:I think that's ex I mean, I think that's a lot of what I've gotten out of it from my own from my own coaching coaching Richard. Like because it sounds like you, like many others, coming from a place of scarcity, feeling frustrated, feeling overwhelmed, you know, sort of like making quick, uninformed decisions. And I think AI actually plays a really good and and helpful role, at least it has for me too, right? Because it can help me analyze maybe some data that I'm looking at. It can help me sort of like determine directionally where I might want to think about this and help me explore ideas, but I'm using it in a way that is helping me expand creatively. And but that's that's the thing, is like if you're sort of like in tunnel vision and can only see the bad and don't have this expansive mindset around it, it's really difficult to make like the best decisions possible in that way. So I think there's room for all of it to sort of sort of come together.

46:56Would you had you ever had any even access to things like that in your career before? Never. I didn't even know things like this existed. Like Tolu for you seems like you were an athlete, an athlete for a very long time and competed at a certain level. So I did not do that. but I I didn't even know things like this existed and certainly not in the corporate world. So I mean I think you sort of like always hear about it in like the sports and athletic world for really like professional athletes. No, it's been I mean if you'd like I can share how I found Dream Fuel and how I even got into this. I like it all kind of started quite honestly it started at the beginning of this year I think like there was just so much happening in the world of tech so much changed like the headlines were very dystopian and a lot was happening within companies a lot was happening in the market and I just I felt like I I think I need someone to sort of like go through this and I that I can talk to openly was it a therapist is it an exec coach and I've done like variations of both in the past and I just felt like I I don't it's not I don't think that's what I need but I couldn't define what it was that I needed either and so I sort of went down the path of exploring those two worlds again and for various reasons like I said just couldn't put my finger on it didn't know what it was and then I found dream fuel and it was I I did like one session just first I talked to Kevin conceptually it sounded great I'd also been listening to just a bunch of podcasts on my own about neuroscience science and listening to other subject matter experts.

48:31So I just had a general interest in the topic itself and then yeah met Kevin then had a session and that session was like immediately it clicked for me and I was like this is what I've been waiting for and this is what I've been needing and so immediately signed up for. Can I ask what what did it change for you? Like what do you what do you do differently because of it? Oh, that's such a great question, Tuloo. So, the thing and again part of this is like my own consumption of the topic too is it helped me and I I use the term selft talk. I don't mean selft talk necessarily in the way of like looking in the mirror and saying I'm I'm beautiful. Yeah. Yeah. more like I did when I too that works too like affirmations and mantras those all work too whether you're journaling them whether you're speaking them out loud but for me my the selft talk I that it helped me with was being aware of my thoughts almost from like a third party perspective and it's like hey you're getting into that mode again pull yourself out of it and talk yourself through it and I just had not been able to do that in the I think the the other thing that it really helped me was like just in the moment like breathing just like sematic work knowing that it's not just up here in my head that I have control over my thoughts even just through my body and that I can control that at any time anywhere.

49:57It just gave me this huge sense of agency that I hadn't been feeling or hadn't been able to feel. Yeah. Fascinating. Yeah. I love that. Fascinating. We definitely talk about that because I found it really fascinating because I like my sister passed away when I was like 33 and she was only 37. Left a 5-year-old daughter behind. It was really traumatic and I had some grief counseling a few months later when it was all like falling apart. I didn't really realize it was but it kind of was. And it was just like online through betterhelp and it was really nice but it wasn't like a worldclass counselor or or therapist and it helped me but I remember thinking being very conscious of like the techniques at play and kind of like what was happening rather than it being like a sort of really transformational experience. Yeah. It was more like a sort of like a a nice person to talk to. Whereas I think with Dream Fuel, what I've observed so far, just from my limited exposure so far, is the most elite coaches, yes, who really understand what's going on in your brain and help you to like find new parts of your brain and physiology and thinking that you would never have access before. Whereas I think then it's not their fault. But the majority of people who do therapy and therefore the people that we go to when we're in crisis and we need help just haven't had that level of of training and expertise. But I also don't think that that's all geared for high performance if that makes sense, right? Like I feel like what Dreamfield doing is like let's get you optimized so you go and absolutely crush it in whatever it is you want to do whether that's life or business or whatever.

51:33But I think especially in England as well, we don't like that high performance part of it. It's not really that's not really there in therapy, you know. So, I actually I had a sports psychologist. So, I got injured, right? And I had surgery and all that stuff. And I had like this really nice Irish lady sat me in a dark room and she just like talked me through stuff. And that was my first like real experience of this kind of thing. But this is like a whole that was just for me to not freak out when I was playing basketball. But this side of stuff just sounds amazing. Yeah, you should give it a go. give it another try. Yeah, it's it's been I mean, sure, I think it sort of like delves into therapy and those were some of the questions that I asked about like what is the difference between performance coaching, therapy, and executive coaching. And I know I don't know if I can really sort of like academically define it the same way that they do. But what I do know to your point, Tolu, is exactly what you just said around performance coaching. Like it's just given the jobs that some of us have, the roles that we our jobs are our roles outside of work. it's just it's it helps you do what you need to do in certain high stakes environments without freaking out. And look, the reality is is I feel like and maybe this is something that I've just become attuned to, but I I think a lot of folks in tech really need this right now. There's a lot of disregulated nervous systems that I come across, people confide in me. and I can see it. I can see it. Yeah. Exactly. Yeah. Yeah, I was speaking to Joe actually today and he the partnerships guy and he was talking about how like a lot of the people that come to him are kind of in that like they're totally burned out or they're really stressed.

53:11I'm like that's literally my job. My job is to speak to people at that point where they're either actively looking because they got rifted and they're you know maybe they've been searching for a while and they're really really low and totally lost or they're just really uncomfortable where they are and they don't have much certainty and and confidence in the future which is an equally sort of bad place to be. or leaders who are carrying that weight of responsibility while trying to stay optimistic and be a good leader for their teams. It's so so complicated. So it's very rare I speak to someone they're like I love it everything's going great people are exactly there's always something there. So I think there's I was saying to Joe I think there's just so many people that I could like bring their way because it's really hard and there's no real coaching around career let alone mental performance. And and not only for us as individuals but when we have that responsibility of others in our care as leaders. That's right. Being able to help people as they go through crisis and those sort of inflection points in their career. Totally. It's the whole oxygen mask thing. And I don't think I've even shared this with the both of you, but I recently brought my coach in person and had him do a session with my entire leadership team. Oh wow. It was a surprise. I just I told my team, you know, we had an off-site planned. We I just told them there was a guest speaker. Did not share anything much more than that. my coach showed up, let a session, and it was it was it was really cool. It was really cool to and ever since folks had been asking me like, "Hey, same questions as you guys.

54:41What do you get out of this? What's it been like?" just a lot of curiosity around around the topic in general. So you you can see very quickly like there is a need especially like you said burnout a lot of uncertainty lack of clarity about what the future's going to look like or hold and then yeah people just looking for a different way of moving through their dayto-day without burning out and showing showing up for their showing up for their for their teams but also showing up for their families and for themselves. That was what I needed too.

55:16Richard Washington:Yeah, absolutely. I was gonna ask one last thing, which is you mentioned the sort of rhetoric in the market being about, you know, very dystopian, which kind of led you on to this like wanting to go and learn more about the neuroscience and and take control. I just wonder what you're most optimistic about in terms of the future.

55:35Tammy Aguillon:It's a little bit of what I am experiencing and and and playing with now in the example that I just shared, which is I there is absolutely like I I use AI more than just in a way to ask like yes, no questions. I use it in a way that's truly like a thought partner and will ask expansive questions around it. But I don't take it for its word. Sometimes it can really lead me down a path where it's like I had not thought about that before, which is this is very cool. Sometimes, as we all have experience, it gives me ideas that I was like, what is this? This isn't possibly anything that I can that I can even further expand on. but I think the future is one where we can use AI in this very creative way to help us create, to help us produce, but to help us think differently than we might, and then still our use our own judgment. And as everyone's been talking about judgment, taste, discernment around the topic to really like choose your path forward, but be able to reason through it and how you got there too. Love that. Love that.

56:33Tolu Adebekun:Tammy, this was this was wonderful. Thank you so much for being on the podcast and sharing. your journey.

56:37Tammy Aguillon:I had a great time. It Was a lot of lot of fun.

56:43Richard Washington:Wonderful. Thank you so much. Everyone else, we'll see you on the next episode.

56:46Tammy Aguillon:I'll see you.

56:48Thanks so much for joining us for the What Makes You Tick podcast. I hope you enjoyed listening as much as I enjoyed having the conversation. Yeah, there's so much value in hearing other people's career stories. And if you're someone focused on growing in your own career, check out our Growth Magnet newsletter on LinkedIn. We'll put a link in the show notes. And we will see you on the next episode.