SG EP38
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Richard Ellis: [00:00:00] In 2025, the majority of executives attending business events say their main motivation was networking. This was not the case five years ago. 70% of senior executives admit to feeling isolated or lonely due to the demands and responsibilities of their role. The result executives that burnout. Missed opportunities for growth strategies that stall from lack of perspective and a negative impact on morale across the organization.
Richard Ellis: Welcome to some goodness where we engage seasoned business leaders and experts to share practical guidance to help today's go-to-market leaders, execute, lead, and win in a fast changing world. I'm joined live today by my business partners, Tim Cruz, mark Gatos, and Heather Easterday. We are in Nashville today following a great go-to market executive round table we hosted yesterday.
Richard Ellis: We decided to invite you to join us as we debrief about the event, share insights we learned, and consider how you can bring some of these lessons to life in your [00:01:00] business. Heather, mark. Tim, welcome. Well, why don't we start off with what the event is for those that may not know, and Heather, maybe you can give us a brief synopsis of what this round table is about.
Heather Easterday: Sure the round table was a chance for learning and networking amongst go-to market executives. Uh, the topic of the day focused on the shifts that are happening in go-to market. Uh, those shifts end up being, not surprisingly end up being about AI and just how, how technology and the speed of change is creating a lot of disruption amongst go-to-market.
Heather Easterday: Structures, uh, we see a lot of, uh, typical silos collapsing and that means that things look a lot different, strategies look a lot different, and we spent the day talking about it.
Richard Ellis: So really kind of focused on the intersection of AI with go to market and how that's [00:02:00] requiring us as leaders to think differently, reimagine processes.
Richard Ellis: And, um, I wanted to ask Mark A. Little bit about. I know for some of the executives you invited to the event, they were excited for a couple of the topics. What, what were a couple of things that they were looking
forward
Mark Gaydos: to learning? There's a, a lot of things on, on, on people's minds these days. Uh, when, when, when it comes to AI and go to market.
Mark Gaydos: So you think about being a sales leader and you think about, um, this disruption that maybe your team might have of, am I gonna be disrupted? Are we gonna use AI to replace me? And so there's a lot of fear. But yet, then also a lot of optimism like, oh my gosh, how can I be more productive? How can I be more efficient?
Mark Gaydos: So it's, it's how do you find the right balance to, okay, what is ai? What does it really mean? What are the practical, you know, we hear terms like agents and workflows and vertical stacks, and so what is that? But then really at the end of the day, how do we use that in our world [00:03:00] to practically be more productive?
Mark Gaydos: Get more scale, uh, but yet not lose the human touch. So just bringing all those together. That's the, the leaders that, that I know, that I talked to, that I connected with, they're like, I wanna learn more about that. I wanna hear more about that, but I wanna engage with my peers and see what others are doing and hear what they're doing.
Mark Gaydos: Absolutely. Tim, what would you add?
Tim Kruse: Yeah, Richard, just, you had said people are feeling isolated and so, uh, to have an environment that is with some of your peers, I think sometimes there's comfort in understanding that, uh, others are trying to figure this out as they go. Um, because everyone knows MIT that study, uh, that was released, uh, I dunno, about a month ago, stating that 95% of AI initiatives fail.
Tim Kruse: They all wanna learn, uh, from each other of, in some ways what not to do. Um, you know, you had shared some stats coming into this, uh, this preview here [00:04:00] and, uh, feeling isolated, uh, feeling, um, a little uneasy. But as Mark said, also getting excited about opportunity, uh, it's nice to be able to probably have a candid discussion outside of your organization at times.
Tim Kruse: So I think, uh, some of that was the, the value in having these type of events.
Richard Ellis: Exactly, and a lot of the responses I got from, you know, the invitations were about, Hey, I'm just, I'm just trying to figure out where am I. In this journey compared to others. Am I behind? Am I kind of on par? Are we leading the way?
Richard Ellis: We're doing some things around ai. What am I missing? And so that was really the spirit of the event, is just to kind of hear from others, learn together, provide some insights. And uh, the other thing I wanted to share about what was the event is it was a half day, uh, event in person. And this was our second event that we pulled off.
Richard Ellis: Right? We, we did one last month in Dallas with great success and we got a lot of positive feedback, so we brought it to Nashville [00:05:00] and, um, you know, I, I'll have to admit that. I was just wondering, coming upon the holiday season, we're asking for executives and leaders to spend a half day with us. Will they carve that out of their calendars?
Richard Ellis: And, and they did. Uh, and so let's kind of move into maybe why we've, we did this, right? Why do we put on the event in particular? Uh, and then specifically, why did we decide to do a half day in-person event versus a webinar, so to speak.
Heather Easterday: We've certainly tried webinars and, and I think there's a, there's a place webinars, there's a lot of goodness in being able to get some quick learning an hour.
Heather Easterday: You can fit it in your lunch, a lunch break. Um. But all of the things we just talked about of feeling isolated, feeling like I really, I really want the inside scoop about what others are doing. We miss that. Yeah, you miss that completely. And uh, for us, we we're a pretty authentic bunch. We want, we want that [00:06:00] connection.
Heather Easterday: And this seemed like, um, not that we're not gonna do a webinar again, but this seemed like a more natural, natural extension of why, why bring this. Face-to-face, why have a little more time. Um, with, with four hours you get better connection, you get a better chance to dive into topics. And people generous enough to give that time.
Heather Easterday: I hopefully think they came away feeling like that it was worth it. I,
Mark Gaydos: I, I think it was, I mean, the feedback that we got was, thank you for doing this. Yeah. Uh, they gave me a chance to get out in the real world, meet real people, make connections, network in my community. But even beyond that, it was. A, a juxtaposition of the topic, which is artificial intelligence.
Mark Gaydos: Yeah, let's get in the room with real people in an organic way. And so that personalization, we're talking about artificial things, let's be together as humans to discuss and debate and unpack and dream what that really [00:07:00] looks like for us.
Tim Kruse: We, even as a team, have gotten really good at delivering virtual events, but there's, there's nothing like.
Tim Kruse: Having a face-to-face event. Um, and the knowing that they were all amongst peers and leaders dealing and struggling with the same, uh, challenges, but uh, also learning where people have had success early. Um, I mean, that's invaluable to hear from someone. And, uh, you know. We made a bunch of new connections, but uh, we saw other new connections being made and I'm sure, uh, we have helped others, uh, to have some follow on conversations that'll be valuable.
Richard Ellis: Absolutely. Uh, a couple of people specifically said to me, you know, my team is not here in Nashville. Right. And so I'm always me working outta my office in my home and, you know, just the opportunity to get out and go somewhere locally. I don't have to get on a plane and fly somewhere, but I could go meet with other business leaders, [00:08:00] talk about relevant things, see what I'm missing, and do that in person.
Richard Ellis: They were like, I, I, I, I was looking forward to this all week. Yeah. And so I think you kind of in this disparate remote. You know, hybrid working world that we live in nowadays, you, you may be under appreciate, you know, the value of just sitting next to people and, uh, and not only networking, but collaborating, discussing, hearing different points of view, different perspectives.
Richard Ellis: And as
Mark Gaydos: you talk about different points of view, uh, the, the, one of the benefits that I heard from folks in the room is. Sometimes, you know, I, I may be in health tech or I may be in, um, you know, communications or manufacturing. So I'm in an echo chamber hearing from my peers and I'm getting mandates from the top AI first and AI this.
Mark Gaydos: But it was good to hear from cross industry. Hmm. Cross vertical, um, experts to see what are others doing and what are other challenges that they're overcoming [00:09:00] in, in their way, in their industry. So from what I've heard from, it was good for them to hear just different perspectives from different industries.
Richard Ellis: Absolutely. We had banking represented, manufacturing, uh, healthcare, medical devices, uh, just the whole gambit really. And, uh, it was great to just see everybody just leaning in at small groups and, you know, sharing, uh, common struggles and challenges that they could all relate to, even though they were in totally different industries.
Richard Ellis: Well, how are you solving that? Oh, I tried that with my team and it didn't work. Oh, yeah. And so just see that dialogue. And that's something to, to your point earlier. You can't do on a 60 minute webinar.
Tim Kruse: No.
Richard Ellis: Right. You try to induce some kind of interactivity with some polls and chats and things like that, but you can't really double click and get deep.
Tim Kruse: And I don't know, we, we all know from, because in our work, uh, our trend is doing our working sessions, our sprints face to face, our content development, our, [00:10:00] uh, collaborative way of, of solving the next set of problems that our, our clients have, and then being able to. Then launch what we've built face-to-face.
Tim Kruse: There's just so much more you get out of it. And it's not just the, uh, you know, what we have organized for the day. It's the, uh, sidebar conversations. It's the hanging out and having a beer when we're done. It's the, uh, uh, grabbing a bite to eat before it starts. So, um, you can't replicate that, uh, over a webinar.
Richard Ellis: Heather, when we were designing the event, you know, one of the things that you brought up earlier was the perspective of we're, we're so used to like, you know, paying an entry fee for a conference and scheduling that three days out of your week to go to that, that share a little bit about the inspiration for kind of flipping the model.
Heather Easterday: Yeah, we definitely, I mean we, we've talked about as a team that for, for an executive to get this kind of [00:11:00] concentrated, I'm, I'm gonna get to talk to my peers, I'm going to get to learn new things. What do they have to do? They, they have to get on a plane, they have to pay, pay, probably a pretty substantial fee to get to go to that conference.
Heather Easterday: And, and, and then. They're in a different city, they're meeting people and then they head home. We flip that and say, let's offer it for free, and let's come to you. Let's come to your city and let's make it so those interactions that you're making are an interaction that you can, you can next week have coffee with that person.
Heather Easterday: And I think there's something really genuine about that. Um, you know, I think, uh, we even heard some folks in the session talk about how just we end up thinking that we have a lot. That separates us anymore in the world. And you come together in an event like that with people locally and you're reminded that whether it's different industries, whether we, we've got a whole lot more in common.
Heather Easterday: And, uh, bringing that, bringing that two executives in their own city, I think is [00:12:00] pretty special.
Richard Ellis: Really good. Well, let's, um, let's transition, if you guys don't mind, into a little bit of the how and kind of how we pulled it off and some of the things that we learned. Maybe there are some practical tips. To share with, you know, our listeners out there in terms of maybe orchestrating their own in-person events, whether it's bringing prospects and and clients together, or their team members, et cetera.
Richard Ellis: But I do know, you know, one of our design principles outta the gate was, we don't want this to be a commercial about ourselves. Right. Uh, that's not what this is about. We're, we're, we're gonna learn just as much from the audience as maybe, you know, the insights we share, uh, to them. And so we wanted this to be really business leaders go to market leaders getting together and learning from each other.
Richard Ellis: And so making sure it wasn't that, you know, Hey, we're, we're here to sell you stuff and was, was important to us, but what were some of the other design principles for how [00:13:00] we executed this that we think led to goodness.
Heather Easterday: One that really goes against, we're saying that our theme was all about how to leverage AI and go to market, and we kind of went against we, we made personal invitations.
Heather Easterday: We said that this was an invite only event. And we reached out individually to every single person that's that arrived. Um, we had some people that said, I get these invitations all the time. I knew this one was real. I knew this one. You approached us differently. So I think that's a lesson that everyone can take away, is that automation is wonderful.
Heather Easterday: It can, it can get us indoors faster, but there are times, uh, and this was one of those times where. The, the personal individual really made a difference.
Mark Gaydos: Heather, talk about how you balanced, uh, as you thought about the agenda and who was gonna be the speaker and how that was gonna flow. 'cause I think what surprised a lot of [00:14:00] people, at least, uh, the people that I knew that I invited that came, they were like, okay, a ai, I kind of get it at a high level, but, but really, what is this?
Mark Gaydos: What am I gonna learn? And they were surprised by the level of depth, but yet practicality. To the, the agenda and the topics and the discussion. So talk a little bit more about the agenda and like the speakers and all of that.
Heather Easterday: So we knew that these are go-to-market leaders, that for the most part, I mean, we had people that were there from AI companies that had some technical skills.
Heather Easterday: Uh, for the most part, these, these are people that, they're not speaking tech as they're, they're a first language. So, um, so we wanted, we. I think if you're going to do an event like this, you have to make sure that there is this consistent flow and that you have someone that's making sure that that, that, that is executed throughout, throughout the session.
Heather Easterday: Now, Richard, you were, you were kind to step up to the [00:15:00] plate and be that for us to be that kind of, uh, that through line, uh, for, for all of the topics, but in both, in the case of Dallas and this Nashville event, we made sure that we had. Local people that we're talking as well to get the perspective of what, what technical, what.
Heather Easterday: The impacts of AI look like because it's, well, it's impacting all of us. It's unique city to city. And I think that that came, that came through, uh, where, where we had, uh, A CEO in Dallas talking about those impacts. We had a CEO here in Nashville talking about those impacts and, and even had a, uh, someone talking from a technical perspective, because I think when we're, when we're looking at this, the build and the sell side of things.
Heather Easterday: That used to be really, really distinct. That line is blurring now. And so being able to have, have people that could speak to both and us help connect those dots between it, uh, was a helpful tip.
Mark Gaydos: Yeah, it was super helpful. I mean, the back, I mean, [00:16:00] what you did, um, in the session yesterday, Richard, uh, in Nashville, you know, starting with the macro, the big picture.
Mark Gaydos: Then taking that down to, okay, what does this mean for go to market and all the different elements of go to market. And then, okay, now let's talk about us as humans. How do we bring in the human element? Um, I thought that was just well done.
Richard Ellis: Yeah. Well, thank you. Um, so as we were kind of crafting the agenda for both of these events, uh, a couple of things we want to keep in mind.
Richard Ellis: One is we want it to be highly valuable, right? We respect everybody's time. They're gonna carve out half a day. With us. We need them to go, you know, walk away going, wow, that was worth my handwriting. So, uh, where does that value come from? We looked at a couple of dimensions. One is just in our talking to prospects and executives and, and other leaders that we know, uh, everybody's in different places in the continuum of AI fluency.
Richard Ellis: Right, and so just kind of grounding where are things [00:17:00] headed with ai, you know, and just getting to that next level of fluency was important. But then also the so what to a go-to-market leader, right? If I'm a marketing leader. CRO, et cetera. Well, what does this mean to me? I mean, it's easy to kind of get lost in just all this magnitude of AI stuff, right?
Richard Ellis: And so gimme some practical things to think about as a leader that I can take back to my team now. And something that I could go do this quarter. Right? And so we wanted to kind of have some of that strategic discussion and insight and, and foster your, your AI fluency, but also ground it in practical takeaways.
Richard Ellis: Mm-hmm. And, and to Heather's point, we. Wanted to also, you know, back that up with local leaders. And so when we leave and go back to our respective cities, they have new connections, you know, in their city they can, uh, reach out to collaborate, you know, continue to brainstorm, et cetera. Alright, well one other [00:18:00] key design principle was that we, and we talk about this a lot, right?
Richard Ellis: We didn't want this event to be death by powerful. So we had a couple guest speakers. Uh, we presented a couple topics, but we didn't want to be just PowerPoint after PowerPoint and speaking at the group instead, you know, we limited to the presentations to about 15 minutes, 20 minutes tops. And then we followed each of those with round table discussions and, and, and not just open discussions and dialogue, but guided exercise to drive that application.
Richard Ellis: I thought that was. Really helpful and a couple people as they left and they were taking their notepads and their playbook that they got from the event they were thanking us for, you know, that table discussion said, I loved your presentations, but I also love those exercises. So that, that's one thing that, uh, kind of resonated that I thought I would.
Tim Kruse: It's, it's, you know, it's the cycle. We always follow a little bit of a tee up and teach, [00:19:00] uh, set up an exercise or a, a collaboration as we are doing here for, um, the different tables and then have that discussion. And then what I always appreciate, um, is the last quick movement is the, the big room debrief because, uh, you know, we had a lot of smart people in the room and if something really.
Tim Kruse: Insightful came out of a table I wasn't at. It's good to be able to hear that too. Absolutely.
Richard Ellis: Any other how to tips or, um, or practical takeaways that you would mention?
Mark Gaydos: Uh, I would just say, as Tim alluded to in any live setting like that, where people in the room, um, just making it experiential meaning.
Mark Gaydos: Bring it down to the ground level, bring it down. What am I gonna do with this? What's the practical takeaway? Uh, make it engaging. So I'm, you know, it's not just one way, [00:20:00] but it's two way, it's conversation and then energetic, uh, just with, uh, the videos or the music or the surveys or the exercises. It's bringing energy, uh, in, into the, into the conversation.
Richard Ellis: Yeah. That's really great. Well, I think we're about at the end of our time, so why don't we wrap up. It's SKO season is upon us, right? Yeah. Uh, lots of companies are thinking about and planning for their sales kickoffs at the beginning of the year, which is one of the biggest in-person events that, uh, people are gonna experience.
Richard Ellis: What are some key takeaways or application insights you might share for those that are thinking about how to pull off an SKO that's meaningful and valuable and gets a lot of return from their investment?
Tim Kruse: Well, you know, the first one you started with, it's not death by PowerPoint. It's not, let's take this as a day and a half to make you more product experts, or it's, it's, what am I gonna do when I get [00:21:00] home from SKO that's gonna help me get off to a fast start in the new year?
Tim Kruse: So I always love, and I think one of the biggest, uh, strengths of ours as a, as a team is making things practical. So when you can leave. And you get home and you know what to go do, that's what you want to get out of it. That's how you help people get off to a fast start. So,
Mark Gaydos: yeah.
Tim Kruse: Um,
Mark Gaydos: and even not just what to do, but how Yes.
Mark Gaydos: How to do that. Um, so thinking SKO think more how and connecting the dots between strategy and vision and execution. So how, what's that bridge? What's that connection point? So just thinking about leaving enough room for exercises, whether it's practicing a new message or, uh, trying out a new strategy or thinking about your, your, your tiering, your accounts for the upcoming year, whatever that is.
Mark Gaydos: Um, think practically of the how.
Richard Ellis: I like that. And as you think about [00:22:00] that practicality, uh, and, and the how I love that. 'cause I'll always, you know, if you know me at all, you, you've probably heard me say this way too many times, and that is. We need to focus on the how, not just the what. And, and we've experienced a lot of sales kickoffs where this is the sales priority or here's your sales play, or here's, you know, how our roadmap or our products be enhanced with ai.
Richard Ellis: And it's all a little, a lot of what to know and what we're gonna do and what we expect you to do, but they don't reserve enough time for, you know, what does that mean for the audience? And then how do they go execute what you are. Um, what your play is or your strategy is, and, and we got that feedback from this session.
Richard Ellis: It's like, I love that, you know, you taught us how to think differently and how to apply it to my team and my business. That can certainly be integrated into Esko.
Tim Kruse: Yeah. And our final movement was talking a little bit about how you're gonna lead your team through this ever changing and accelerated, uh, pace of [00:23:00] change and.
Tim Kruse: Gotta tell 'em how to do it. But we also talked about you gotta give some of the, the why, so people are looking for purpose. Um, if, if executives are feeling isolated, think about those team members that are, you know, yes, a lot of people are returning to the office, but those that aren't even more isolated.
Tim Kruse: And if you don't bring them together and give them some, some why and some purpose along with the how, uh, you know. You're gonna have disenfranchised employees, you're gonna have people that, uh, aren't getting a lot out of their work, and that's not how you wanna start the new year.
Heather Easterday: And I like what you bring up there, Tim, is that I think it's easy at this time of year for someone to kick themselves and go, oh, we're too late for planning a great SKO because we haven't had time to book that.
Heather Easterday: Astronaut speaker, whatever it is. Oh, [00:24:00] and, and what you get at, those are the things that are really gonna matter. Yeah. Is not, not the astronaut speaker, not the professional football player speaker. It's those real connections. That real why, and then how that they're gonna come away with. And it's gonna actually not just impact the year for the company, but impact those, those individual team members when they, when they go back.
Heather Easterday: And I think the thing we learned that we can really apply from. What we've done with these round tables is that authentic interaction makes a big difference. So if you can build that along with the why and the how, it's pretty amazing.
Richard Ellis: One other thing that I would mention is, you know, and one of the things that we spoke about in our round table yesterday is the fact that the workforce these days is running on empty.
Richard Ellis: Yeah. You know, they're, they're lacking motivation, optimism, agency. Right. There's frustration and anxiety out there. And so, uh, you know, they're running out of this quote unquote psychological [00:25:00] fuel. And so if you kind of think about SKO as, uh, an event as a refueling station, right? It's an opportunity to reinvigorate your.
Richard Ellis: Teams, your employees, and look at that as a, a, an intentional way of getting people together, impact teams together, uh, to, to really drive, you know, some meeting, high agency, more motivation, et cetera. And I know, you know, most s ks are, they tend to be energetic and rah rah, but I, I think there's, uh, an opportunity for all leaders today to say, Hey, we need to lean in specifically around.
Richard Ellis: Our employees and the lack of motivation or the anxiety around, is AI going to take my job, et cetera, and use this as an opportunity to, to refuel it.
Tim Kruse: You know what, Richard it when you're saying that, Heather reminds me of one of our favorite, uh, leaders we worked with of Louis and, uh, so if you think about SKO being a, a [00:26:00] refueling event, well, he used to say when he'd be talking about someone's funnel or pipeline, you can.
Tim Kruse: Fill it up in essence with junk. But his analogy would make is you can fill a gas tank with water, but you're not going very far. And so if you're fueling them the right way, that's what everyone wants. I mean, I don't think you come across a go to market leader that, uh, doesn't want to use SKO to get their team off to a fast start.
Richard Ellis: Right.
Tim Kruse: Well guys, we
Richard Ellis: are, I think, out of our time here. It's been awesome. The yesterday together and with all the, uh, attendees was awesome. Great to debrief you with you guys and, and record it in the process. So hopefully that provides a little goodness to, uh, to our readers. And of course, you know, I'm gonna ask, you know, we don't have to have everybody answer, but, uh, I always like to ask, what's some other goodness that you've.
Richard Ellis: Had in your life, in your, in your day recently that you might share that [00:27:00] has nothing to do with what we were talking about today.
Tim Kruse: Anything
Richard Ellis: come to mind?
Tim Kruse: Well, I always have something 'cause I always tie it back to my kids. So, uh, I like to give this, this shout out. So my daughter started running cross country this year.
Tim Kruse: She's a freshman. And, uh, I have always appreciated sports 'cause you get to see, when you put effort into something, you improve And, uh. That goes with, uh, the real world that goes with, uh, work careers. And so, uh, watching her work hard this year in practice and as a freshman, uh, making varsity and getting to run in California, what they call, uh, CIF championship was, uh, was a lot of fun.
Tim Kruse: So that was, that was some goodness around our house. That is some goodness.
Richard Ellis: Well, with that, let's bring it to a close, and thank you all for listening and we'll see you next time.
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