Mastering Go-To-Market Strategies w/Anne Slough

Brian Dietmeyer: Foreign. Welcome to another episode of, uh, Closed Mode, the Enterprise Sales Show. I'm Brian Dietmeyer, CEO of Closest Strong, the home of precision guided selling. And today I'm really lucky to be here with my pal and business associate, Ann Slough, who I've known for years. Anne's the head of Go to Market Enablement with Colibra. And if you're not familiar with them, they empower. See if this sounds like your. Your right speak. And empower data citizens to take command of data and AI transforming possibilities into progress. How did I do, Ann?

Anne Slough: That sounds great.

Brian Dietmeyer: Well, welcome to the show, by the way.

Anne Slough: Thanks, Brian. A pleasure to be here. I was really stoked to spend time with you today, so thank you.

Brian Dietmeyer: Yeah, over many years in many different roles for both of us. Like we have talked about, you know, an enterprise selling, and it's a subject, uh, we both live in and are also fascinated by. And it's funny too, because I was looking at your title, which I've seen not frequently, but have seen a few times, Go to Market Enablement, which I really like because it's like it screams of execution to me, right? Adding the Go to Market before enablement. And so that's a lot of what we're going to be talking about today. So, uh, my first question for you, and we were talking a week or so ago and you said, look, every year in the companies that you've been with, uh, you said a new methodology gets introduced. And from your perspective as head of Go to Market Enablement, uh, why do organizations keep pulling that lever? Because I will do a little spoiler alert. You also were frustrated with that. So talk to me a little bit about that.

Anne Slough: Yeah, you know, Brian, I think about methodologies like I think about the, um, billions and billions of dollars that we spend on the fitness industry, right? We pay personal trainers, we want a dietician, we want the latest and greatest workout equipment. Because we're searching like this holy grail for physical fitness or this image of what we think we want our bodies to look like. And methodology is kind of the same thing in go to market organizations or sales organizations. We want to create a branded experience for our buyers. And the most obvious way to do that, besides in marketing, is the one to one interactions our sellers are having with our buyers. The way we interact with us should create or live our ethos as an organization. It should feel different to buy from us at Calibra than anyone else in our space. And a methodology seems like a logical path to go down because methodologies basically are Teaching your sellers how the how, not the what, your sales process is your what, but how that interaction is going to feel when you're doing a good discovery call, what the skills are that comprise a good discovery call. So logically it makes sense. It also gives us a consistent language within the sales organization to coach around to gauge performance by. So all of that makes sense. So I think logically as leaders we think we need this, we need a common language, we need to be able to create this experience, this branded experience. Just like all those other things make sense when you want to lose weight or create the perfect body that you want, but they often, most of the time fail. You know, every, it's like we're on this two to three year merry go round of uh, buy a methodology, implement the methodology, try to measure this success, realize it's not working or a new CRO or new sales leader comes in and so he or she brings in what they like from the last company and here we go again, we do this all over again. And so it's, I think that's the why behind it. I think the intent is good. There's this deep desire to get it right. It just doesn't happen. Simple, I can have the training plan for my personal trainer, but if I never go to the gym, probably not going to get that ideal state achieved. Right?

Brian Dietmeyer: That's a theoretical response, right?

Anne Slough: Right. Yeah, yeah. Well and then I think the practical responses, even if we do those things well, we're dealing with humans and getting human beings to change their behavior is really challenging because they have to believe that changing my behavior is going to get an incrementally better outcome than what I'm doing today. And so if you have a seller who's successful doing his or her own thing and then you say, hey, I want you to do it this way, they're not going to adopt it and do it right.

Brian Dietmeyer: So did you just say caging their behavior? I love that statement. I've never heard that. You, you said something else, Ann, that I want to react to. That's uh, brilliant. You often say things that are brilliant. But you said something about kind of uh, brand equity, the Calibra brand. And years ago, people who listen and watch the show know I often reference Bill Marriott because he's a hero of mine, Marriott hotels. And he told us once that every decision we make is a deposit into or withdrawal from brand equity. And you built on that by it's brand execution. Uh, every deal that you're doing, every customer interaction you have and by the way when you see my LinkedIn post on this subject, you'll know where it came from. So thank you for that and I completely agree. So something else you and I talked about is, oh, you know, managers, uh, should coach more. So you've had rev ops and sales ops experience as well. So. And I'm just going to go direct to a question I know you're passionate about. Is it going to happen? We're all trying to get to this holy grail of frontline managers coaching this stuff or even coaching deals. What's your take on that?

Anne Slough: Yeah, I think, you know, often, often people say, well, I don't have time to coach. I've got so many other things on my plate. I just think it's a cop out. I don't believe it. I know for a fact that human beings have time to do the things they want to do. It's really funny how that works out. And I understand as a sales leader that there are incredible pressures on that role, be it an executive or a frontline sales leader. They have a lot of things that they have to do in the organization. But I'm going to date myself, Brian, and I'm going to talk about old Stephen Covey, right, the seven habits of Highly Effective People. And he often talks about, you have these big rocks and if you put your big rocks first, everything else will fall around it. Well, that's kind of how coaching works. It has to be your number one priority and everything else fell around it and you have to make it a priority. But we don't because I do the same thing. We get consumed by the day to day activities that seem urgent and important. If we think about those quadrants, right, it seems like they're in the urgent, important quadrant, but they're just really urgent and probably not important quadrant, but they, they require. There's somebody screaming at us for something. I think we just don't make time to do those things.

Brian Dietmeyer: Yeah, it's funny. Two quick reactions. One, I interviewed a CRO uh, on this program and one of the things we talked about is this subject and he was like, make the time. But tell me if I have this wrong. When you and I were just offline chatting a, uh, week or two ago, I thought I heard you say, look, it's not going to happen. Did you say that or did I make that up?

Anne Slough: Uh, I think it can happen, but I think the odds of it happening are probably low because first of all, for a lot of managers, they've been put in this role not because this is their desired state. They don't really want to coach others. They don't really get satisfaction through others. You either get satisfaction through others or through self. Those are the two drivers. And good leaders get their satisfaction through others. And peak performers, like performer salespeople, they get satisfaction through self. Often we promote these peak performers to be in these leadership roles. And so now there's this um, there's these competing drivers that we're asking of this person. So I think it can happen. Yes, you can do it, you can learn to do it, you can better time manage. But in general it's probably not going to happen because it's not my natural state. I'm not driven that way. It's hard, it's squishy. I gotta deal with another human and give them feedback and they're gonna argue with me and then I'm just going to get irritated and I could be like looking at a pipeline report or crunching numbers instead. That's better and easier in black and white. I just think it's hard and I just think people path of least resistance and probably won't do it. I mean I think we've proven over how many years, 30 plus years that you and I have been around in the business world, if not more, they can do it, they're just not going to do it.

Brian Dietmeyer: Well, it's, it, it's uh. I keep saying this but you always say interesting things whenever we talk over the years. So what? One of the stats that comes to mind based on what you just said is like there's also, there's a timing issue and then there's a skills issue of the frontline manager. And I just read a report recently and I'm sorry, I can't reference the actual report. Reps said uh, I actually want more coaching. Which was a little bit surprising to me because I thought it was like get, get. I think about, I'm a huge fan of uh, Drive to survive, the F1 show on Netflix. And some of the drivers sometimes are like get out of my ear. Right when they're driving 200 miles around the track. Especially Yuki Tsunoda. He's mean with his handlers. But I thought reps were that way. Like get out of my ear, leave me alone, let me do my job. They said I want more. But they double clicked on that and said what I get however is fire drill auditing when deals are in trouble. I don't want that. What I want is preemptive strategic assistance. And so that goes to that skill issue. It's like do how many frontline managers. The auditing for the fire drill is reasonably easy. Hey, and you know, this, this or this. But the preemptive strategy stuff is uh, much harder.

Anne Slough: I think that's worth sitting on a minute because that's what I was going to follow up. It's the kind of coaching we give.

Brian Dietmeyer: Yeah.

Anne Slough: And where sales leaders tend to like to spend their time. Are pipeline reviews forecast? When I say like to spend their time, I don't mean they wake up and going, oh, I'd love to do a forecast call. But that's their comfort of coaching in the numbers. Forecasting pipeline review. Um, an urgent call from a rep going, hey, I need to close this deal. Let's talk about it and figure out what levers we can pull to get this deal closed in the next week because the quarter's ending. They, they like that adrenaline shot, right? They like the cortisol, they like the hunt. That's why we're in sales. We like the hunt, we like closing it. We like the hit we get from adrenaline. Um, we like that, we get condition to like that. And so listening to a recorded call or ride alongs or listening with a rep on an in person call, going with them to listen, stopping debriefing, giving targeted feedback, meaningful targeted feedback is exhausting. It requires a lot of mental energy from the coach. Right. And so that's the kind of feedback reps don't get. That's what they say they're hungry for. I just delivered a two day um, boot camp around a new go to market strategy that we're um, implementing and part of that was a day and a half of the reps pitching our new value prop and the way we're going to go to market and just pitching, pitching, pitching and getting feedback. And I was giving feedback to a rep and I have a very structured process. It's very specific feedback. And I had a rep look at me and she said that is the best feedback I've ever gotten in my career. Because you really honed in on the skill part and how I can get better now. It's not that I'm all that in a bag of chips. I am not. It's just that I had really good teachers, um, who taught me to put that energy into the feedback. But it's exhausting. I left that, I was exhausted. Mentally, physically, spiritually, intellectually exhausted.

Brian Dietmeyer: Yeah, yeah, that's why it was good. But you just kind of segued into the next uh, question and that and your issue before about uh, Brand execution at the deal level, which again, I absolutely love and I'm stealing. But when you and I met, um, you were at LSA Global and you managed, I think it was the strategy and culture practice there. And with that experience, with that kind of targeted role that you had, where does strategy typically break down as it relates to being connected to the frontline rep and the deal level. And as we say, turning like your brand execution into behaviors by reps, what does that break down?

Anne Slough: Uh, well, what I love about what I think you're doing and you're tackling this problem is that execution gap. So, you know, executives sit in a room and they talk to consultants and they do market research and they look at their product or whatever they're delivering to the market, and they say, okay, we're going to create this strategy because this is where we think we can win, right? This is, uh, the niche space where we think that we can do this better than any of our competitors and where we can win. And they craft this strategy and then they start to cascade the strategy down. So that's failure, part number one, point number one, because every time you cascade the strategy down each level, research shows that we lose about 50% of the messaging. So when an executive communicates it down to the senior leadership team, about 50% of the messaging is lost. Because we as executives created the strategy, we know it inside and out. But when we verbalize it down, cascading it down, there are parts we may leave out or just assumptions that are made. And so the message gets diluted each level, it goes down number one. So that's one point of failure. Second point of failure is we don't do a good job in general of helping each role within the organization understand where they plug into the strategy. What is your piece of the pie that's going to be able to execute on the strategy, and how does that fit into the overall strategic picture? So we don't make good students of the business and organizations and helping people understand. The third failure point is around the culture. We don't judge culture good or bad. We just ask one question. Have we created the culture that is able to implement the strategy? That's the third point. You have these three major points of failure, I think. And that execution gap, Brian, which is, I think what you're really trying to tackle as well, is how do I, as an individual seller, understand the strategy of my organization, create the right culture, and then day to day, when I'm interacting with a buyer and the sales role. Let's take that role, how do I live that? How do I make it happen? It's really, really hard for those reasons. And so you need a scalable fail safe automated process that's aligned to the strategy that we execute against one.

Brian Dietmeyer: Yes, yes to all that. One thing that comes to mind again when you're talking about this is like the, you have your strategy and then we have the messaging. And where does the messaging fall down? One of the things that we're seeing, because you're right, we're deep into this and trying to figure out how to do it, is that uh, beyond messaging, there's a bunch of other smaller increments. When you look at your strategy, it's just like, okay, how should we be qualifying opportunities that are in line with what we want our folks doing? Right? And what new stakeholders do we need to be talking to and about what, like given our strategy, what KPIs should we be talking to them about? Let's get much more dialed into discovery. How do we find problems that are in alignment with our brand that we want to solve for and even solution configuration? And that's where I see some of this falling down is not breaking, netting out the strategy to say, all right, what pieces, uh, require a behavior change at the front line and then let's track it with the deal cycle from qualify to close. What should we be doing at every stage? Uh, not just messaging. So uh, another question for you, kind of back to methodology. You had mentioned, uh, that there's uh, a belief that it's table stakes. Uh, and you said even uh, for reps with tenure, people see it as table stakes. So what should the next layer of uh, enablement look like? We've talked about the problems with methodology and why people pull that lever. But if you could design a modern solution, what do reps need today that either you're using or doesn't exist that you would design?

Anne Slough: Yeah, well, I'm um, designing, I hope what I'm designing right now, my current role is kind of what I would like to think is the future of enablement. And it's got a couple of components, right? So number one, I believe that. And let's just stick with the sales role, like what sellers need. We could talk about the whole go to market organization, but we're going to stick with sellers. I believe they need a personalized curated experience. Just like in marketing. Marketing talks about personalization, right? Like you can't do mass marketing. You have to personalize the message. It's got to really resonate with that particular Buyer, not even Persona, but that particular buyer. Well, I think sellers are the same way. When, when we have sellers come into the organization. The vision that I'm trying to create is, hey, Ann, um, tell me about your experience. Tell me the markets you've been, the verticals you've been selling to, how long you've been selling, where do you think you're really good? Where do you think you need some, um, reinforcement? And let's assess the seller. Number one. Then let's create a curated experience. So, you know, if you are a, um, let's just. I'm not a golfer, but let's take golf. If you're a golfer and your long game is really good, do I need to spend hours and hours with you teaching how to drive the ball? No, I probably need to focus on your short game. Well, sellers, that's the kind of experience I want to create for them. Number one, a curated, personalized experience. Then I want to be able to use technology in order to amplify their ability to be successful. That can make them more efficient than, you know, maybe it frees up time. We use technology and AI to do research and automate and write back to their CRM. And we can also use technology to enable them to have better conversations, whatever that looks like for that seller. So personalized curated technology is an amplifier. I also think we need to deliver enablement just in time and in the workflows where they work. So if I primarily use a CRM, or I'm using conversational intelligence, or I'm using a sales engagement platform, whatever tech I primarily spend my time in based on my sales role, that's where enablement needs to be delivered just in time. I'm in stage two of this deal. What are the skills, knowledge processes, and tools that I need to implement to move this deal from stage one to stage three based on my experience. So that kind of enablement, I think, is the future. And I think finally technology is catching up to allow us to do that. And I think that's really where we need to go instead of this she dipping. Everybody gets the same thing. We spend three days teaching a big sales course, and then off you go. Like, I think those days are gone or should be gone, rather. I would like this new vision, but

Brian Dietmeyer: I love what you just said, and I would add a piece to that about, like, how do we do all those things in line with strategy? And I feel like that that's been the missing link. It's like, how do we do those things generically? Right? But no Given what it is we're trying to get done here, how do we do those things? So have you seen any data, again, Revops sales ops go, uh, to market enablement? Any data to point to how well we're executing a strategy or how well it's being communicated to reps? Or is it mostly just kind of what you seen and been frustrated with?

Anne Slough: Well, I know there's a ton of like the McKinsey's, right? The Deloitte I know, Gartner, Forrester, they consistently put out data that I, uh, think is somewhere between 75 and 80% of all strategies fail. Um, or the execution of it, rather. I shouldn't say the strategy fails, but the execution of the strategy fails. And I think it's consistent around that for the many of the reasons that we've just talked about. You know, you either don't have the right culture, you don't have the right talent, you don't have the right systems, you, you don't have the right change management in place. I mean, I think strategy, typically, that's why it fails. I mean, that's, uh, why we have, that's why we have the big consulting firms that make all the money because they can come back in and say, oh, I have the right strategy, but they typically fail.

Brian Dietmeyer: Yeah, yeah, you. And thank you for reminding me you do have that Forrester experience as well, which is. And I think what was your vertical expertise there?

Anne Slough: So I was in the Rev Op service at Forrester.

Brian Dietmeyer: Yeah, yeah. So you have that question I just asked. Now I remember why I asked you that question because you have some insight into that, given what your role was. So I really, uh. Man, I feel like we could go on forever, but I know people don't watch forever. But, um, I'm glad to have this conversation with you and a couple of professionals in your role where we're beginning to look at this kind of execution layer of saying, all right, how do we go make this transition from methodology, which is generally how to sell, to maybe the next leap and enablement is how do we execute our strategy one deal at a time. Like, let's train people in how to do that. And it's tricky too, because our strategies are shifting. But that, that I think, and I know you and I agree, we've talked about it, that that's like the next level is. Yeah, yeah, enough with generically, how do we sell? How do we get this done? You know? Yeah, I'm really happy to hear your insight on that. You've been super, uh, generous with your time and your ideas and planning. For folks who watch this show, we spend time up front getting ready for this and you spend time on your own and it's appreciated. I think of closed mode as like this body of knowledge for those of us who live in this space and I love continuing to add to this so people who are in roles can say, hey, what are my peers thinking about? So you're awesome as usual. Thank you so much for this.

Anne Slough: Well, thank you Brian. It's always a pleasure to spend time with you and um, just trying to figure it all out. Right. We're all driving to the same goal. We want people to be successful in the roles, companies to be successful but also do meaningful work. And so I think if we can figure that out, executing the gap between strategy and just day to day what we're doing to align to it. Um, I really appreciate the opportunity. Thank you my friend.