SG EP41
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[00:00:00] Richard Ellis: This year, AI dominated business conversations. So did speed, pressure, and the feeling that everything was shifting at once. But looking back, the hardest problems weren't new. They were just harder to ignore. AI didn't fix weak leadership or sloppy execution. It revealed them. Companies with real clarity moved fast.
[00:00:20] Richard Ellis: The ones faking it got buried in tools they didn't use Well. Purpose statements held up fine in pitch decks, but they fell apart under stress in leadership. It showed up in how people acted when things got difficult, not in the strategy document. 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.
[00:00:47] Richard Ellis: This episode is our year-end review. We pulled moments from past conversations to look at what 2025 actually taught us and what's worth carrying into the next year. Here we go. [00:01:00] This might be the hardest thing to accept this year. Tools don't fix confusion. They make it worse. Ai, MarTech messaging frameworks, strategy slides, none of it works if you haven't figured out what you're actually doing first.
[00:01:14] Richard Ellis: A lot of organizations grabbed new capabilities fast, but they skipped the slower work defining how they operate the underlying processes. What they believe, how decisions get made. Without that, even good tools just generate noise. Our conversations this year kept coming back to that problem.
[00:01:34] Ben Scoones: So I think understanding your own workflow really, it, that should be a basic requirement, I think for, for probably doing anything within a business.
[00:01:42] Ben Scoones: But I think it's particularly important when you're looking to, um, integrate AI technology. Um, because. If you think your workflow really is a, a series of steps for how you, how you do some job, or how you do some task within your company, and [00:02:00] even though AI is a really powerful, um, and impressive technology, it's can't do everything by itself, right?
[00:02:07] Ben Scoones: It needs some help, it needs some direction for you to be able to do that. Um, kind of just like a person would really, if you think about, you know, AI in some situations is maybe as just as good as a person. Think about those two interchangeably. If you can't tell a person what to do and expect them to be successful, um, if you can't define that person's role well enough for them or the task that's required of them, why would you expect them to do a good job with that?
[00:02:32] Ben Scoones: Um, and I think similarly, if you can't do that and you're just expecting AI to be able to do all the work for you. Uh, then you should expect the same results. You're not gonna see success there.
[00:02:41] Richard Ellis: No, no. That's a, that's a good way to put it. In terms of just kind of thinking what level of, uh, documentation or structure or, you know, um, process has been lined out for where you're going to apply?
[00:02:56] Richard Ellis: AI, or like you said, really needs to be, you know, processed [00:03:00] first before you overlay any kind of tool or technology. That confusion doesn't exist in your workflows and systems. It shows up in how you communicate your brand message.
[00:03:11] Stacy Leidwinger: My highest belief in anyone that talks to me. Messaging is so critical to everything the organization does, and where I see people often fall challenged is trying to come up with the perfect message.
[00:03:23] Stacy Leidwinger: Hmm, how are we going to stand out? How are we gonna talk about the value? How are we gonna say we're unique? How are we gonna make sure people really understand everything we do? And one of the things I often say is, you know what? It doesn't matter while words matter. It doesn't matter having the perfect words, it matters.
[00:03:39] Stacy Leidwinger: Being consistent. It means that what is on the website is the same words that sellers are using when they're engaging and SDRs are calling. It's the same words when an executive gets on a phone for an executive call. It's the same words in the RFP. It's the same words from customer success after you've acquired a customer and are retaining them.
[00:03:58] Stacy Leidwinger: When an organization all uses the [00:04:00] same words. That's when you get power of brand, power of message, and it's less about finding the perfect word. It's all about being consistent in your delivery of that. And yes, it will evolve over time. I think sometimes people seek out for the perfect message, and I say it's really about consistency that drives success for a whole organization.
[00:04:23] Richard Ellis: 2025 gave us speed. It didn't give us better judgment. Automation got faster information, got cheaper decisions got harder. Everyone had access to ai, but that wasn't the difference. The difference was knowing how to think clearly while using it. Judgment turned out to be the scarce thing. The leaders who struggled most were waiting for tools to handle the parts that tools can't handle.
[00:04:48] Richard Ellis: Prioritization, discernment,
[00:04:50] Ben Scoones: trust. Your employees are not just these, uh, automatons performing this one job probably. Um, they're gonna have a range of skills. They do a range of different [00:05:00] things in their job, and so. You know, you're probably not thinking about laying off a lot of workers necessarily, just 'cause everyone gets 10% more efficient.
[00:05:08] Ben Scoones: That doesn't mean suddenly 10% of your workforce is useless. You've probably got lots of other tasks that you could be allocating those people to, and now you get to do more of them. That's the thing. You, you get to do more with less, uh Right. Hopefully, anyway. I mean, I know. For certain applications, AI systems can be expensive to use and to maintain.
[00:05:28] Ben Scoones: But, but that's the goal. Um, you should be able to do more with less now. And probably a lot of companies want to do more and they just haven't been able to do it. Um, so, right. Like you said, it's, it's an opportunity. Right.
[00:05:40] Richard Ellis: As those expectations grew, so did the pressure on leaders, many of whom found themselves navigating uncertainty in isolation.
[00:05:48] Richard Ellis: 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? [00:06:00] Am I kind of on par? Are we leading the way? 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.
[00:06:12] Mark Gaydos: There's a, a lot of things on, on, on people's minds these days. Uh, one when, when it comes to AI and go to market. 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.
[00:06:36] Mark Gaydos: Like, oh my gosh, how can I be more productive? How can I be more efficient? 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 to practically be more [00:07:00] productive, uh, get more scale, uh, but yet not lose the human touch.
[00:07:05] Mark Gaydos: 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, I wanna learn more about that. I wanna hear more about that, but I wanna engage with my peers. See what others are doing and hear what they're doing. Absolutely. Tim, what would you add?
[00:07:21] 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.
[00:07:47] Tim Kruse: They all wanna learn, uh, from each other of, in some ways what not to do. And, uh, feeling isolated, feeling, um, a little uneasy. But as Mark said, also getting excited about opportunity. Uh, it's nice to [00:08:00] be able to. Probably have a candid discussion outside of your organization at times. So
[00:08:07] Richard Ellis: something else came back into focus this year.
[00:08:09] Richard Ellis: The fundamentals never went away. We just stopped doing them listening, focus, preparation, discipline. It's not exciting, but it beats novelty almost every time. When teams forgot the basics, problems showed up in places, leaders assumed were fine. For decades, sales leaders have lived and died by one number.
[00:08:30] Richard Ellis: The win rate, we present it in board meetings. We use it to stack rank our reps, and we often see it as the ultimate measure of our success in today's complex B2B sales motion. However, that win rate can be one of the most misleading numbers on your dashboard. What I find is that it often becomes a vanity metric.
[00:08:48] Richard Ellis: It tells you what happened, but it tells you nothing about the incredible cost of that win, and it can hide deep inefficiencies and lead you to celebrate deals that were actually unprofitable for the [00:09:00] business. There is a much better way to measure the true productivity of your sales engine. Let's start with the anatomy of a vanity win.
[00:09:09] Richard Ellis: So I'm sure we've all seen this once or twice. I've seen it dozens of times in my work with clients. The team lands a huge well-known logo. The announcement goes out, high fives are exchanged, and the win rate for the quarter gets a healthy boost. On the surface, it's a great success. But what did that win actually cost?
[00:09:28] Richard Ellis: In most cases, it was a deal that took 18 months to close, consuming hundreds of hours from your top sales rep. It pulled in your best solutions engineer for countless custom demos. Your product team was sidetracked with one-off feature requests, and then the final hour you gave up 35% discount to get it over the line.
[00:09:47] Richard Ellis: Everyone celebrated the logo, but no one calculated the cost. The win rate went up, but the business may have actually lost ground. That's the danger of a vanity win. The same principle applies to [00:10:00] storytelling too. Not just what happened, but why anyone should care.
[00:10:04] Jim Karrh: Why is story important? And you know, what we think about customer success stories, but what makes stories in general compelling?
[00:10:11] Jim Karrh: Well, they tend to have components and there's a path, uh, and people talk about hero's journey. They talk about other, other structures, but if you think about movies or programs that you like, they, they tend to have a very common, uh, sequence that they follow First. We, we set the scene, we're introduced to characters.
[00:10:30] Jim Karrh: And we get something about their environment. So maybe it's, you know, it's a, it's a couple with young kids in a suburban setting, and we hopefully, if it's written well, we like the characters or we, we are engaged with them in some point. And then once we kind of have an understanding of what this world is like, something happens, it's an alien invasion, it's a new, somebody coming into the uh, uh, into the neighborhood.
[00:10:56] Jim Karrh: It's, uh, the person loses their job, uh, [00:11:00] or they, they see someone that they're really interested in. You know, will the guy get the girl? Or will the girl get the guy? Or whatever. So something disrupts that. And then our, our, our person, our main characters have a decision to make. They have a, an uncertain path.
[00:11:15] Jim Karrh: What are they gonna do? What's gonna be the result? Do they have. Other people who are affected by this, a family or, or a community, do they have a guide? Do they have a Yoda that that's bringing, uh, helping bring them along? And then what's the result? And hopefully it's, uh, happily ever after. Uh, and so those are the, the parts of the story.
[00:11:34] Jim Karrh: And, and there are in what we typically see in, in case studies and the structure of customer success stories get most of that. So they'll, they'll have, here's the setting. Right here was the, here was the environment, here was the problem. Someone who was running a division or we had this unit, or we had a new solution, or we had a new customer.
[00:11:56] Jim Karrh: Right. And, and so we had to decide what to do. So there was some [00:12:00] sort of intervention. We, we bought something, we did something different, and here was the result. And, and to a degree, Richard, that that's pretty good, but it's not complete because what's missing in there? There's, there's not emotion. In most of them.
[00:12:16] Jim Karrh: And so they're, they're technically correct and we have most of the components. But I would say the challenge for a lot of customer success stories, however we convey that, is to bring that human element in. 'cause there was something that happened. It was, and usually a, a fear and anxiety, um, gnawing, uh, that.
[00:12:37] Jim Karrh: That goes with the decision to buy something or to intervene in the first place.
[00:12:44] Richard Ellis: One theme kept coming back in very different conversations this year. Execution isn't neutral. How leaders act under pressure, how they handle wins, losses, accountability, conflict, that tells you more than any value statement. [00:13:00] Culture isn't what's written down. It's what gets tolerated, what gets rewarded.
[00:13:05] Richard Ellis: What gets repeated over time, execution becomes a moral act.
[00:13:10] Steve Graves: Lots and lots of scientific research has been done the last decade for sure, but it was done before that. But you know, lots more has just really piled into the market into the last decade or so. Around this idea of both dopamines and stuff that you mentioned.
[00:13:23] Steve Graves: What can happen with us when we win, when we succeed is that we get a shot of Red Bull. We get an internal juicer effect about all things. I mean, nobody's making the case that that's all negative because that's not true. We all need to win in some things. But what happens is, is I've gotta be careful A, that I don't get over addicted to outcomes.
[00:13:47] Steve Graves: Results that are only wins because I don't care who you are, nobody wins every time, every day with every encounter. You just don't. [00:14:00] Most of life is built around somebody winning and somebody losing. And in order for somebody to win, often somebody has to not win and call it whatever you want. Right? And I've gotta get used to that.
[00:14:11] Steve Graves: So there's kind of an expectation that can begin being built. And then as something you mentioned earlier, which I couldn't agree with more, is often what happens is I begin to allow myself to change the way of how I think about my own sets of boundaries, my own sets of values, my own sets of expectations.
[00:14:35] Steve Graves: And that's where actually a lot of people begin to have moral failure in their own life. Um, because they didn't set out to say, well, let me just be a failure. But they set out. Becoming more relaxed with some boundaries or some convictions in their own life. And a lot of that ties back to when we won.
[00:14:54] Steve Graves: When I was successful, I began to think I'm somebody, I'm better than you, or I'm bigger than [00:15:00] you, or I'm immune from, from any kind of danger or challenge or whatever. And that's just not true. And that's the reason why it's so important through life. We take our wins and our losses, we take success and our failures, and we let all of that kind of help make and form who we are as individuals.
[00:15:20] Richard Ellis: That moral dimension shows up most clearly in how leaders invest in other people, especially when it comes to mentorship and shared decision.
[00:15:29] Chris Strammiello​​​​: In any good organization, there's typically a lot of intellectual horsepower around you, a lot of experience around you, and some very different mindsets. And very different approaches.
[00:15:41] Chris Strammiello​​​​: And you know, if you are humble enough leader and you're really focused on driving great outcomes. You gotta find a way to bring those perspectives and insights into the mix for you and your team. I certainly never believe I have a monopoly on good ideas or even my best team [00:16:00] members do. And so I, I wanna bring in people's perspectives.
[00:16:04] Chris Strammiello​​​​: I wanna bring in the wisdom of the broader organization. And then, you know, and maybe this is just growing up in a Sicilian family, I wanna argue things to the finish line, so I wanna debate it. I wanna interrogate people's conclusions, and I wanna have a little bit of maybe even disagreement until we get some alignment on what we feel is the best perspective.
[00:16:27] Chris Strammiello​​​​: And everybody feels good that they can rally behind it.
[00:16:31] Richard Ellis: Trust is the one thing leaders can't automate. It doesn't come from dashboards or declarations, it comes from behavior. The small repeatable actions that show what actually matters. In 2025 employees were watching, they noticed whether leaders lived the values they talked about...
[00:16:50] Larry Sweeney: Newsflash.
[00:16:50] Larry Sweeney: Nothing else is more important than you and the relationship you have with your manager. It's M and mss, Richard, money and managers. That's what keeps people in their [00:17:00] jobs. They're making good money, they got a good manager. Then all is well in the world m and ms.
[00:17:06] Richard Ellis: Before people follow a leader's vision, they decide whether they trust the person standing in front of them.
[00:17:12] Chris Blocker: Leaders have to, to show up, not just competent people, but also the kind of people that I wanna follow, right? And so. Um, a, a younger generation is looking to leaders to say, okay, who are we really? Mm-hmm. Who are, who are you? Can I can, I believe you know, that we are who we say we are. Um, and so there, I think there's, there's an entire generation that is looking for leaders to, to tell credible stories mm-hmm.
[00:17:40] Chris Blocker: About the organization, about who we can be, about how we can create greater impact beyond. Simply, you know, growing and uh, and succeeding for financially.
[00:17:53] Richard Ellis: Looking back on 2025, the lesson is simple. Leadership was never about the newest tool or the loudest trend. [00:18:00] Clarity before action, judgment before speed, fundamentals before novelty.
[00:18:05] Richard Ellis: And showing up consistently and with integrity, especially when it's uncomfortable. That's what we're taking into the year ahead,
[00:18:16] Narrator: some goodness is a creation of revenue innovations. Visit [email protected] and subscribe to our newsletter.
