Why Your Reps Leave SKOs No Better Equipped to Sell with John McMahon and John Kaplan

0:00John Kaplan: If you're putting together an SKO and you do not have a point of view on how AI is going to help the sellers do something better, be more productive, make more money, help understand customers better, you're not demonstrating it, you're not practicing it, you're in trouble. Welcome to the Revenue Builders Podcast, a weekly show featuring B2B sales leaders and executives. Hosted by five-time CRO John McMahon and force management co-founder John Kaplan, the show takes guests in the barrel, behind the scenes with the people who've been there, done that, and seen the results. Revenue Builders covers best practices for scaling and growing your business while sharing the pitfalls to avoid.

0:52Johnny Mac, how are you?

0:54John Kaplan: I'm good, Cap. What about you? I'm doing pretty good, man. I'm doing pretty good. Can you believe we're going to have this conversation again, which means at least half the year is over. Have you been having a good year, bro? Good year, buddy. Good year. It went fast, dude. It's not over yet. No, no, but it really does seem to be going fast. So, look, we decided we want to talk about, just for planning purposes, around August, September, every year, we talk about the concept of, you know, getting your organization together in some type of sales kickoff mode. Right. Let's talk about some of the basics, Johnny.

1:42What are some of the best things when you think about an SKL?

1:50John Kaplan: What are some of the best things that you should be thinking about? And where are some potential pitfalls? For me, most SKOs that I've attended when I'm not running it myself, It's like too much inspiration and not enough execution. You know, it's loaded with, the agenda is loaded with the CEO talk and how we did last year. And they'll throw a motivational speaker in there that has nothing to do with, you know, selling. They have new product announcements and then they have all the awards. So the reps can leave, you know, energized because there's a lot of inspiration. but they're no better equipped to go out and win another deal, right?

2:39So I think like a strong SKO, you should be answering the question of what do I as a rep need to do different on Monday? And if you're not answering that question, based upon everything that you see in your sales force, where reps are getting stalled in deals, like where are the two to three areas? You know your reps get stalled in deals. your SKL should mainly be about that. Right? I don't care about having every C-level person get up on the stage and tell me about themselves and tell me about their org chart. Quite frankly, I don't give a shit about your org chart if I'm a rep. All I care about is what are you going to do to help me sell more?

3:26How are you going to train me so I can more effectively do my job? And if you're just talking about you and how great your organization is, but you're not telling me about how to compete more effectively, I don't give a shit. I don't care.

3:39John Kaplan: Yeah, I think you're bringing up a, I think the basic premise of your message is, if you don't think about this SKO in terms of the audience, and what do you want the audience to experience? What do you want them to take away? If you don't start there, which most companies don't. they just like we got an sko we got to get some product stuff done we got oh should we do training should we you know let's have a motivational speaker i think johnny what surprises me is the number of companies that um underestimate that probably more than 50 of that organization sitting in that room or sitting on that zoom and we can talk about that uh is making up their mind whether or not they want to be there for another year.

4:31John Kaplan: So I think some companies just think, well, we've got an SKO. This is our team going forward. I actually believe the team that goes forward happens after an SKO. Right. That's true. But in the SKO, just staying on this, I mean, they have a tendency to cram like 30 days, 30 topics into like two or three days, right? They're trying to cram an entire year into like three days. Instead of, like I said, focusing on two to three things, that you need your sales force to do better and focusing on training only on those things. So what they do is they do product training, the new pricing, the compensation, the messaging, the med pic, you know, prospecting more AI, you know, CRM hygiene, forecasting process, all of that stuff.

5:17And they jam it. And what they do is they jam the agenda with 30 things, of which no one's going to be able to retain 30 things. And then they're constantly trying to stay on time because they jam in the whole agenda. And they get too many things to talk about in too little time. Instead of saying, let's back up, let's figure out the two or three things our Salesforce really needs, and let's really bear down on that. And this way, you never really run over your agenda because you only got three things you're focused on. And if you think about the Uber theme of communicating to a sales organization, I just wrote this down.

6:01I think, you know, you have to hit some type of purpose. So you have to connect with a go-to-market organization of like, what's our purpose?

6:14John Kaplan: Like, does what we do matter or not? Like, so that's got to be hit in the SKL. And that's not necessarily somebody from the outside coming and talking about, you know, how do you create, you know, resilience or what have you. I'm not downplaying it. I do, you and I both do a lot of that when we come in and talk to organizations. But I'm always asking about the theme, like, does what you do matter? And then do you have evidence around it? So to get for people to get passionate about the company, there's got to be evidence of the purpose. So that SKO better have some evidence that the product's getting better, that we've got good proof points, that we've got, you know, a good strategy, that we've got, you know, what are the analysts saying about us, whatever.

6:58John Kaplan: There's got to be some evidence. And then I think another theme is going to be, where is this journey going to take us? And I call that like the vision, which is nothing more than what does purpose look like in the future. So not only do I want to understand, like, does what I do matter, but in five years, three years, what's it going to look like? And is that a journey I want to take? I think a lot more people are asking that. So you kind of go at the high up level and then you break it down to say, okay, if you're buying it, if you want to get to the summit, let's say, and this is what, you know, here's what it's going to take to get to the summit.

7:40John Kaplan: So first you got to paint a picture of what great could look like. And I always thought you did a really good job of this. And then you break it down to making sure they're very clear. Here's the strategy to get us there. And here's the expectation. here's the execution expectation that's associated with that i see it i see that hosed up it's not a very it's not a hard uh message when you think about it but think about how many people hose it up they talk about strategy that's all good but there's a big disconnect between that vision and what you what i'm gonna do tomorrow to become a better rep 100 that's why you got to break it down to the execution of but they don't ever do that they They don't ever do that.

8:26They don't ever break it down to this is where our sales force needs to get better because we've done this type of analysis and we know exactly where you guys get stalled. And this is what you need to fix it. And that's what we're going to train you on. And I think it's the other thing that happens is a lot of these organizations. They get inundated with, you know, product training. So we're going to come out with a new product, right? So the product teams kind of start to dominate the kickoff, and they're showing new demos and roadmap slides. But I can't tell you how many times I've listened to some product manager stand up there, talk about a product, and no one in the sales force actually understood what they were talking about.

9:09Because they don't care what the product does. They only care about how it solves problems for their customer, for who's the persona we're selling it to, why the problem matters. how the customer measures it, why they should change now. And when they can't answer those questions as product managers, the whole thing, that whole hour is just lost. You can see the sales force just sitting there looking at each other like I have no idea what the guy's talking about.

9:36John Kaplan: Yeah, I think that's really good. I like that. And I also think that when you do, because you have to talk about the product. When you do talk about the product, I think you also have to be vulnerable and realistic you have to talk about in a way that what's going to change like this has been really really hard for us to sell or this is what you've been struggling with in the marketplace this is the feedback we're getting for our from our customers when i think about the skos that i've been a part of and i've been a part of a lot of them the thing that gets the most energy in the room is when the rep understands how the suck is going away like how the company realizes something sucks and how And the customers realize, and that's been minimized, and here's what's been done about it.

10:23John Kaplan: I think that's pretty powerful, but some companies don't want to get vulnerable and say, hey, the product was wherever it was. And I think that's a big mistake. and the leaders, we had Thurman on earlier in the year. And one of the things I took away from his was, like, he thinks his job is removing friction in the sales organization. And he actually thinks about that from the CEO level too, but certainly from the CRO level. Things like redundant processes, you know. Johnny, when you were leading, how did you know? because there was redundancy. There was stuff that wasn't adding value. There were people that weren't adding value.

11:10How did you know where to address the friction in the sales organization

11:17John Kaplan: so you could be more equipped to stand up in front of them and say, hey, here's what I'm going to do about what you're struggling with, and here's what's going to change on Monday? Well, because to Mark's point, that's your number one job. Like your number one job as a sales leader is sales productivity. So what are you doing today to make sure that your sales force is more productive tomorrow? So you're constantly looking for things that are interfering with sales process, with sales productivity. So that could be, you know, I'm not training them effectively. I'm not constantly teaching them.

11:58Order processing has taken too long. You know, we can't get offer letters out. There's a whole bunch of things that get in the way of making new sales force more productive. And usually it's usually self-inflicted internal things. And that's your number one job as a CRO is to make sure that you're running interference and clearing those hurdles out so your salespeople don't have to run into them every day.

12:22John Kaplan: How were you gathering that information? I remember. You just know. You just know. You're at PTC. You just know. I remember at PTC, you calling me, and I was several levels below you. And you called me and asked, you know, how are things going? A very open-ended question. Did you have a cadence of going to the top sellers or to the up-and-comers? It's called going on sales calls. You go on sales calls with sales reps, and you're riding in the car with them, and you're asking them what's going on. They're telling you exactly what's going on. You know, you don't just, you know, you have windshield time with them.

13:02And then you also go out to dinner with them and have a drink with them. And, you know, they start to open up and tell you some of the things that are going on in your organization, some of which you already know about and some of which you're surprised to hear about.

13:16John Kaplan: How many of the companies you're advising or working with today are actually doing windshield time? Very few. So what do we do about that? Get out from behind your desk and get on an airplane and go make some sales calls. Let's talk about the data. You're pretty surprised about what you learned. I know. The data that we're, you know. Even separate from SKOs, sometimes, you know, in a growing organization, a lot of the ones I was in, we were growing 100 % a year. So you're always looking for sales reps that could move up to sales leaders. So you'd ask the sales managers, hey, do you have anybody in your district, region, area that can be promoted?

14:00No, we don't have anybody. And then you go out and make a sales call with a sales rep, and you're like, oh, my God. This guy is so good. This girl is so good. I've got to promote them. They've been hiding them, so they hide them from you, too, as your organization gets big. Because they don't want to lose this rep that's so productive. for them. So they think more about themselves and about the company. And there's these, you know, really good reps that are there that are easily can become managers.

14:27John Kaplan: That's a great point. Like if you feel like you're a CRO, let's say you're having one that's in person, we can talk about in person versus, you know, not in person, let's just assume in person. And you feel like a stranger. Like we all get to it at some point in an organization, when you realize how many people you don't know. And as the company grows and grows and grows, and I think if you're feeling, if you feel that, you're probably not getting out amongst the troops as you need to. I always use that as a barometer. When I'd sit down, I'd be like, hey, how you doing? I'd talk to somebody and say, how long you been here?

15:06And they'd say, like, a year.

15:09John Kaplan: And I didn't know who they were. That's a problem. depending upon the size of the organization. But if you feel like a stranger at an ESCO, or you feel like you have to really kind of let people know who you are and what you're about, I can tell when I go and I see CROs that are kind of, they're selling kind of who they are and what they believe in. Now, if they're new and the organization doesn't know them, okay, I get it. But when they should know them and they're kind of selling themselves, there's always another story going on. Yeah. Yeah. I think one other thing that other thing that people don't teach enough of is like how reps should create business cases, especially these days where you have to really sell value.

15:50And even, you know, some of the guests that we've had on the podcast that talk about how difficult it is for customers to truly see the difference in products and truly understand what type of value they're getting. If you're not really teaching your reps how to figure out current state costs, the future state value, the ROI, the payback, risk reduction, strategic impact of the purchase that they're about to make, then you're just really not equipping your sales reps with the ability to extract a lot of value for the customer and extract a lot of value for your company. And they just don't spend enough time telling reps and explaining to them exactly how to develop the skills and knowledge around building a very impactful business case.

16:43John Kaplan: and even a follow-on to that is they could do a great job of telling them about it but they don't let them practice it so there's there's not enough practice at skos there's a lot of talking and telling but there's not a lot of showing and observing do you agree yeah it's usually a one to many some bunch of people get up on the stage and there's you know a couple thousand people sitting in the audience and it's one to many. There's no real interaction. Like I said, it's boring. It might be inspiring. They might charge up a little bit with some vision slides or something or some motivational speakers, but it doesn't really do anything for what you're going to do the next day when you're trying to sell.

17:25John Kaplan: Yeah. When I look at skill sets, you can add to these, but I look at three skill sets that I think always have to be addressed. You know, the first one for me is how do I help sellers attach to the biggest business issue facing a customer? So meaning, how do I take whatever we're doing technically and how do I, you know, uplift that conversation to include that conversation, but to include it to people that would care about a business outcome for that? And then, you know, how do we take our, this is a huge one for me. How do we influence the decision criteria with our differentiation? You know, help me be a better, you know, more voracious qualifier.

18:11John Kaplan: Like when I look at those three things, I would expect to see something at SKO around those three things minimally as a skill set. Do you have any others? Or do you disagree with any of those? No, I don't disagree with any of those. I mean, one of the biggest issues I see, too, is that CROs are really late in getting out comp plans and territories. So then what happens is, you know, the year ends January 31st. Most of the Salesforce knows that a lot of their territories might change and they don't have their comp plan yet. So then they do the SKO. You know, they ended the year, end of January.

18:52They don't do the SKO until like March 1st. So there's a whole month where these reps are just sitting there with, you know, sitting on their hands because they're like, I don't know my territory. I don't know my comp plan. So there's nothing for me to really do right now. Now, that's what a lot of the guys, the really good guys are still out there selling no matter what. But you're really hurting the productivity of your sales force when you haven't rolled all those things out, you know, before your SKO. shouldn't be something that they're talking about during the SKO.

19:24John Kaplan: No, that's a really good point. I think it's a kiss of death if you show up in an SKO and those things are ready. Because think about it, if the rep's not ready to decide, and that's one of the reasons why they're not ready to decide whether they're going to sign up for another year or not. And I don't know what my comp plan is going to be, or I don't know what changes there are going to be in my comp plan or how I can make the kind of money that I want to make. And, you know, what I'm signing up for is the responsibility for my franchise, for whatever that is, a number of accounts or geographies or what have you.

19:58John Kaplan: But can you imagine going to like a kickoff and they do it? I would say probably 50 percent of the people we talk to, John, they don't have that done by SKL. I know. It blows my mind. I can't imagine. You know, another thing for me is. where we are right now. Talk to me a little bit about AI and SKOs just in general. What are your thoughts on that? I'm thinking if you're putting together an SKO and you do not have a point of view on how AI is going to help the sellers Do something better. Be more productive. Make more money. Help understand customers better. You're not demonstrating it. You're not practicing it.

20:53John Kaplan: You're in trouble. If you don't have an AI point of view for this SKL, that's another kiss of death. What do you think? It should only be that you're using tools or implementing tools that are going to help the sales reps be more productive and sell more. It's as simple as that. if you were a CRO today, Johnny, I know this is a real, you know, this is a really appropriate... Putting me on the spot here? Not a little bit, but I think you're going to have a good point of view on it. Like, what would you be expecting a company to do for sellers as it relates to AI? What would you be expecting? I mean, at the highest level that you're going to make your sales reps more productive.

21:44John Kaplan: What are some of those things that are, we talk about productivity a lot. What are the productivity suckers? Like, what are the, you know. Well, the current productivity suckers is the current tech stack. It's awful. You got Gong and Outreach and Clary and CRM and Word and Excel and, you know, all these different tools that the manager wants the sales reps to pay. attention to. And then the sales reps keep their forecast and deal updates, you know, in Word or Excel or some other product. So where the big productivity losses are is when I got to update the entire tech stack all the time. So I'm wasting probably five hours a week updating the tech stack and updating my own tools.

22:34And then right after I update them at Friday at five o 'clock, it's outdated by Monday at 12 o 'clock. And then I made a sales call. My manager's calling me for updates on the call. Who'd you talk to? Do you have a champion? Who's the competition? Did you set the decision criteria? They're asking me all those questions. So I'm constantly updating them verbally, even though I put all this stuff in the tech stack and I'm wasting another five hours a week and five hours a week times 12 is 60 hours. I'm wasting basically almost two weeks at a time. And then another big time sink is my set. Let's say my sales cycle is six months.

23:21So I need John Kaplan on the first call, John McMahon on the second call, Susie on the third call, Sally on the fourth call, Kaplan again on the fifth call, McMahon again on the sixth call, Sally and John on the seventh call. And every time that that happens, they're always asking me to update them on the deal and where the deal stands and what they should do and what I should do and who's the people involved and all that stuff. That sucks another five or six hours of my week. So I'm really losing probably three to four weeks out of a quarter, just updating everybody, updating the tech stack and updating everybody.

24:02That's where this huge time sinks. And it's all because the managers don't trust the data that's in the tech stack. So they're just hounding and pounding the sales reps into submission because they have to give an accurate forecast. So they're basically doing what I call chasing the forecast instead of effectively coaching and going on sales calls with reps and making them more productive. Yeah, I think that the productivity, the seller productivity, John, we would expect in 2026, 2027, that seller productivity

24:42John Kaplan: would be improving, but yet the data is actually telling us it's going the wrong way. So the amount of revenue per rep, the amount of reps that are making their number, all of those are going the wrong way. You see, as companies scale, right? Their productivity, when they're$10 million,$20 million,$40 million, their productivity is kind of going up. The ramp time for a sales rep is maybe six months. They don't really have much churn. And that's going up. They start to scale. And as they start to scale and they get close to like 100 million or so, then all of a sudden you start to see that the ramp times go from six months to nine months.

25:24The productivity starts to flatten and the churn stays about the same or goes up. Then the CRO is underneath the gun because the CFO goes to the CEO and says, hey, you know, the ramp times are going up. The productivity is flat. Churn is flat to increasing. So what are you going to do? Because your CAC is going up. So now what are you going to do to reduce CAC? And the CFO will offer guidance. Okay, there's three things you could possibly do. One, we can cut the number of SDRs. Two, we can cut the comp plan. Three, we can cut the manager to rep ratio. So what are you going to do? Pick one, Mr.

26:02CRO. So the CRO picks one or picks a combination of all three. Okay, so now the CFO got what he wanted because they cut the cost, but it doesn't mean that the productivity is going up. In fact, you might have made the productivity decrease more because you have less SDRs and you have the manager-to-rep ratio has gone up. So it's like, and it's all because no one, they're not effectively training and coaching reps. They're mainly chasing the forecast. So that's the biggest problem that I see inside Salesforce today.

26:37John Kaplan: I think so too, Johnny. And I think one of the symptoms of that is, I think the average tech stack just for go to market is 12 to 15 products. So when you think about the impact. None of which talk to each other. None of which talk to each other. Most have their own sign-ons. So can you imagine a seller to generate a forecast to generate their rhythm on a daily, weekly, monthly, quarterly basis? They're going in and out of 12 to 15. Well, they probably have some single sign-on package like Okta or something. But my point is it's a different interface. It's a different, I'm going out of one system that's not talking to another system.

27:20John Kaplan: And so that. They get tool fatigue. So, you know, big heads up to CROs right now. If you're not looking at your engagement model, which says, how is this buyer buying? How are we selling to this buyer? What are we doing in each one of these segments or each one of these stages? Who's doing what when? and then take it down a further level to say, how are we qualifying that business? What are the gates that we need to be able to create value and capture value, deliver value, and then start to map the tech stack to it? It's not a hard exercise. You start to map the tech stack to it. I think you're going to find out what's the cholesterol building up for the reps when they show up at an SKL because it's wearing them out.

28:20John Kaplan: I think it's wearing them out. So I would - I'd say on the SKL, I also think that there's no, what they do is they typically are training the reps. I mean, there's no differentiation typically in an SKL that you go to where there's, you know, the rep training, manager training, executive training, right? And the managers need to learn how to inspect things, coach the sales reps, challenge the sales reps, challenge customers, qualify deals, they can't be doing just the same thing and learning the same thing as the reps. You have to have manager training. You have to have sales rep training, right?

28:58Because you can train 500 reps, but if there's 50 managers that, or 60, 70 managers that don't know how to reinforce the training, how to hold people accountable to make sure that they're implementing the training, then it's all lost. And that's what you see at these SKOs. It's a big high, big inspiration, really low on execution. They talk a big game. And then one month later, all of that stuff's disappeared.

29:30John Kaplan: I think that's such a huge, I think that's such a great point. At the SKO, like most companies, at the very most, will train everybody together. or at the very, let's say at the very most, like they'll say, we'll throw everybody in a room and we'll, but in order for that behavioral change to happen, it's never going to happen unless something has changed at the frontline sales manager level. And most companies never do it. They're like, hey, we trained everybody on a new value proposition. We trained everybody on a new tool, on a new product or what have you. and they've never addressed what is going to have to change for manager behavior in conjunction with seller behavior.

30:18John Kaplan: And they never give the, I shouldn't say never, but just think about it. If you're planning for an SKO now and you don't have a section in there for the managers just to be with each other to say, what's going to, you said, what are we doing differently on Monday for a seller, you got to have a section in there that's what are we doing differently on Monday as a leader? Exactly. Right. Yeah. What are we missing? Well, one other thing that I've seen at some companies is that they don't, they're not honest. They're not honest about competitive differentiation. Oh, yeah. which is just so tough on the sales reps because they want to believe that they've been trained effectively and that their company truly knows the strengths and weaknesses of their own product and the strengths and weaknesses of the competitive product.

31:18And then they wind up listening to what some product manager or product marketing manager has to say. and then they go out there and they say those words in front of the customer and they get the shit beat out of them and they find out that they weren't told the truth. Gosh, that's just awful. And you see it happen a lot at SKOs because they do a lot of product training from the product managers and product marketing people.

31:47John Kaplan: I think this is one for me is you can feel it in the room and your most experienced sellers, the ones that have what my father used to say have the most sand in their butt, which means they were hard to move out of the way, which means they had credibility and foundation. When those people are balking at something on a product, well, what are we doing about this? What are we doing about that? And if you don't have answers for that, like if you're a product person and you haven't tested that with some of the best sellers in the company and you haven't gotten that feedback, you're still going to get it in the room and there's nothing worse that can happen than a product or a strategy or whatever, marketing campaign, and it just falls flat because a senior seller stands up and asks some questions.

32:42John Kaplan: Not even rudely, just asks some questions that you don't have a good answer to. But this goes back to a tech stack for me, too, because for me, I want to know what the best sellers are doing. I want data on what the best sellers are doing. I want data on what the best customers are doing. I want visibility. And I want it at the workflow level. Like, I want it at the seller level. So I would also think about all this stuff that we're talking about, that if we don't have a plan to figure out a way to get people access to the best information in the company, I'm hesitating to say in a dynamic way because I know there's a lot of technology behind that, but that's what all of our customers at force management are asking.

33:39John Kaplan: What are the best people doing? How are they doing it? I know we said these were the differentiators. The reality is, Johnny, we just got off a podcast with Crunchbase, and the CRO there told us that 10 ,000, there's 10 ,000 AI companies now, 10 ,000, which are getting, what did we say, 70 % of the funding or what have you. But the reality is, is that there is changes that will be happening under our very feet. So whatever we kick off at SKL, the reality is in a month, two months, three months or what have you, those things could need to be updated. So I think having a plan for that, and I know you've always said, give airtime to the people that are doing it right.

34:31John Kaplan: Just let people see what great looks like. right and at your SKOs I always knew that you know the top sellers were going to get up not in a hey we're giving them a big bonus and making everybody but basically you're asking them and helping them giving them a platform to talk about what they do that's different that makes them great and I think that's a big component it's got to be on the agenda yes sir Mr. Kaplan what are we missing bro I think that's a good wrap it's a good wrap I have no other thoughts on SKO right now

35:06John Kaplan: All right, brother. I'm dry. That's it. Well done, buddy. Thank you, Mr. Kaplan. Thanks to everyone for listening to another episode of the Revenue Builders podcast. Thanks for listening to today's episode. If you enjoy the content, please subscribe, rate, and review the show to help us reach more people. This show is brought to you by Force Management, where we help companies improve sales performance, executing the growth strategy at the point of sale. Check out forcemanagement.com for more information.