How to Run Evidence-Based Deal Reviews That Predict Revenue with Mark Siciliano

Hey everyone, welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I think make a positive impact on the world around us. Now today, my guest is Mark Sicilano, who's actually a really good friend of mine. The reason I wanted to have him on today's show is that he's coming out with a new book called Working Great, and I was actually honored to write the foreword for this one. Now Mark started out as a CPA at PricewaterhouseCooper. He actually got cut playing pro baseball and ended up at Oracle, where he helped build the Oracle Sales Academy. From there, he scaled enablement at companies like Marketo, Demandbase, Drift, and Sprinkler, all which are companies I've actually trained and worked with him at the majority of them.

In this episode, Mark breaks down what he calls the discipline gap. That's the distance between the standard a company announces at kickoff and the standard it actually enforces week after week. We get into why forecast calls turn into story time, why evidence beats confidence, and the one question Mark says tells you if a deal is actually real. I'm going to let you wait for that one. Then we dig into judgment. It's the one thing that AI can't touch yet, and we talk about how to pass it down to the next generation. I hope you enjoyed this conversation as much as I did. Let's make it happen. Hey, real quick. If you heard me last year, you know I stopped taking manual notes on all my sales calls.

Yes, I'm still using otter.ai, but now I'm using their desktop app, which means there's no bot jumping into my sales calls. And honestly, it's become way more than just a note taker. With the desktop app, otter captures all my sales calls and turns them into searchable insights that sink straight into my CRM. And then I can ask otter chat any question about any meeting or conversation I've ever recorded. The best part? Chat is now connected with all the tools I use. So if something's buried in tools like Notion, Google Drive, Gmail, Salesforce, whatever, I can still find it all without leaving otter. But here's what I actually love about it. The knowledge doesn't disappear when the call ends.

It lives in otter. I can spot patterns across my pipeline, remember exactly what was said, and walk into my next call way more prepared. The time it saves me is absolutely ridiculous. And that's before you even get into what it does for teams. I'm partnering with otter to give you an exclusive offer. Go to otter.ai forward slash JBSales to learn more and start selling smarter today. Mark, my friend, welcome to the Make It Happen Monday podcast, my friend. I was looking forward to this conversation. We were just talking a bunch of shit, but I just want to kick this thing off so we can actually record some of this and put this out to the public because I think it'll be value, but it's great seeing you, man.

How are you doing? I'm doing very well. Thanks for having me, John. It's always a pleasure speaking with you, for sure. Always, always. And you got this book coming out, which I'm excited about. We're going to get into it. It's called Working the Gray, Where Revenue Leadership Actually Happens. And you have been in this space for a while now, so I think you know more than most. But as my audience always knows, I love the origin stories, man. I love them. And you got some fun ones because you got your parents, the background. So talk to us about what made Mark Mark. And then I want to learn about the school and then the CPA and then the transition to tech. So all the fun stuff. But talk to us like growing up and where'd you get your morals and values and all the fun stuff.

It sounds your childhood and mine were pretty similar, John. I started, I'm one of five brothers, you know, grew up in one house where my dad and his and mom lived with my dad's brother and mom and family. So we were all in one house growing up and, yeah, I was just a sport kid trying to figure it out, you know, working under an Italian-Irish family, pretty disciplined, lit the candle at both ends, so to speak. But ultimately, you know, first in my family, going to school, I went on an athletic scholarship. I played basketball and baseball there and really thought that was my calling. I was going to be a baseball player, I figured. Obviously, a six-foot 180 wasn't really the size for somebody, as you see in the pros today.

So I did what my father told me I was supposed to do. You only go to college to get a accounting degree. And I thought, okay, I'll give that a shot. And so I actually started my career as a CPA at Pricewaterhouse. I used to do audits and read financial statements and do tax returns. And after a little while, I thought, oh, my gosh, it's great for those that are really good at it. But I must not have been that good at it because I was starting to get a little tired of it all. And, you know, fate is an interesting bird. I knocked into somebody that was working at a company that was relatively new, and it was called Oracle. And if I was interested to sell ERP systems. Sounds sexy, man. And I said, well, how much does it pay?

And they were saying, gee, tech is kind of lucrative. And I could read a financial statement. And I was always the person who would put things in plain English. And I had somewhat of a teacher's background. I was a graduate assistant in school. So I said, yeah, I'll give it a shot. I'll go do that. I interviewed and got a contract by a guy named signed by Larry Ellison. And I've always kept that. I started as a sales engineer at Oracle and then moved into sales and got very lucky. And became part of a group that built the Oracle Sales Academy. And so we were, because I could explain ERP and share industry expertise, I was able to educate reps and SCs how to speak value to the software that we were providing.

And so that sort of resonated in Mark Hurd at the time, was very interested in building this academy and growing it from a select number of schools. And long story short, we built it. And we built this academy, hired 500 people every quarter. It was just a rocket ship. And really enjoyed it. But when you're training 5,000 people, you know, over time, you got a little bit old. And I felt that I could add a little bit to those companies that were maybe growing from that 100 million to a billion number, where Oracle was already there. I was one of 130,000 people at Oracle. So I got an opportunity to work with a few people that started Marketo. And so we were the juggernaut from 100 people to 3,000 people.

And got acquired, moved on, went to demand base in the same vein, grew and scaled that ABM company and worked with some great people. And similarly, got opportunities where the PE firms came calling and acquired and moved on. And I felt I was an enablement person for hire, where I would come in, scale organizations, work directly with the CROs, because I had had very close ties to the leadership over at Oracle. So I was familiar with how to scale a business, but I was better suited as the consigliere for a CRO than trying to be a CRO. I thought I was better equipped to handle those emergencies or the things that were necessary in the short term to fix and build the behavior that the selling community could grow.

And so that model tended to work. And over the years, I've tended to find these companies that were really growth leaders from the Marketo demand base, Drift, Sprinkler, all of those really cool places that allowed me to really take over and drive the strategy that CROs were hoping were being delivered across their organizations. And the interesting thing I found throughout was that everyone had the correct strategy. Or at least it sounded correctly from the stage at kickoff. But it was really interesting how it would change. And maybe we'll get into this a little bit. But ultimately, my background story starts as just, you know, lower middle income kid outside of New York City, figuring out college sport business, and then got into tech.

And I've ridden the wave for probably about 25 years now. Love that, man. And I mean, the names that you got there, like Oracle, Marketo, Demand Base, Drift, right? You don't have any slouch either, though. You haven't noticed that. Well, I worked with them. I was kind of like the cool uncle hanging out with them. So I wasn't part of the family. But you wrote that each one showed you how fast a revenue system fractures when the discipline underneath it isn't real. Which fracture taught you the most? Like on each one of those rocket ships where it was most noticeable, that gap between, you know, hey, the vision and this is what we're doing to the execution of it, right? Where was the one you learned from the most where that gap was big enough and you learned how to fix it?

It was at Marketo because Marketo was a rocket ship. And Phil Fernandez was just a genius and understood those early days of marketing automation. But what I found, every time we tried to roll out a training based on a strategy, based on whatever it was and how we were going to hire exponentially to cover the revenue that we were expecting, what was being delivered was never being recognized even four weeks after something was being trained. Like training was on point. Strategy was associated with it. Everyone had buy-in. But no one really invented that system to check whether the standard the company had announced was the standard it actually enforced week after week. And over time, you know, I didn't have a name for it, but now I do.

And I called it the discipline gap. The discipline gap, yeah. Right. And so this discipline gap, it's like the distance between those two things. And you'll find it once you understand what the discipline gap is in every pipeline review, in every forecast call, in every kickoff, that didn't really change a single behavior two weeks later. And so at Marketo, what we found originally was we called it first-line manager assessments, where we would look in and go, you know, these are the closest people to the fire. And ultimately, if we can build behaviors, discipline, across the manager suite, that can exponentially improve with just a one- or two-point increase in win rates based on how they coach, reinforce, align with customer success and marketing and all those kind of things.

And so we created a discipline that made it a cadenced approach to doing things weekly. It wasn't a certification that ends. It wasn't a strategy that completes or a framework. This is a rhythm. It's a rhythm that's established weekly, and it never ends. But we can never define it, right? And over company after company, starting at Marketo, I saw, wait a minute, if we're able to create the discipline to allow people to use judgment, which is more important today than it was maybe 20 years ago when I started, we're able to build in those consistencies that we never get to see in a forecast call. Because I've always seen, as dashboards have improved, a fictitious one and a real one look exactly the same.

And it's the difference between evidence and confidence. And maybe that's where my CPA background comes in, because I've always felt that you had to reconcile things when you saw something. And great CROs, since the days of Marketo forward that I've worked with, have always been able to say the right question in those moments of silence. Because forecast calls today, you know, or pipeline reviews, they just go through. You want to ask the easy question. You want to get through it. You're not really validating. And now it just continued to progress. And we always addressed the problem differently each time a problem arose each quarter. And in fact, we weren't really measuring the true problem.

The true problem was the discipline and not asking the right questions soon enough so that we can course correct in week two instead of having an emergency in week 12. Why, I mean, there's study after study after report after report about how frontline managers are where everything lives and dies, training, and we got to get them to coach. And for almost 25 years at this point, I've been hearing about, oh, we got to get our managers to coach. And, you know, and it's still usually promote your best reps to be the managers, which is usually the worst things you could possibly do. And, you know, we think sales reps don't get much training. Well, managers get almost none. And then they get given tools like, you know, the gongs of the world and those type of things.

Oh, no, this is where you can coach. Well, not really, because first of all, they're not taught on how to coach. Second of all, it's usually subjective. Third of all, you know, the tools that we have now of being able to record a call and, you know, the value prop of, oh, you could just skip to the part where somebody says pricing. Bullshit, because what somebody said at minute three is probably going to dictate what happened at mini 27 when pricing came up. Or, oh, well, you can just listen to it at 2x, you know, 1.5. No, no, because tonality and inflection matter when you're asking a question. So, if you have a 30-minute call with a rep that you want to coach on, that's 45 minutes at minimum of if you want to do it right.

Multiply that by five reps by however many meetings that you have. A manager doesn't even have time to. So, that's why they revert to deal chasing because that's what they're good at. How do you fix and how do you delineate between managing and coaching? And should a manager be a coach? Or should we separate the roles at this point and just wave the white fucking flag and say, you know, just let managers do the deal chasing and let's hire a coach because this is absurd. Great question, but I'll put it this way. We will spend or companies will spend millions of dollars on the right strategy. They'll spend tons of money on figuring out comp plans and how to improve implementation strategy. There's no money spent on first line management at all.

But it's not about true coaching. It's actually building discipline that creates a cadence weekly where coaches, all of them, ask the same question to their reps in the reviews that matter. Not meetings for meetings' sake. Coaching happens in the immediacy. Coaching happens when it happens. No one learns anything in some scenario-based training where we create a fictitious company. Nor does it happen when you do a kickoff and you get in a room and everyone rah-rahs and tells you that this is what we're going to march toward. Because when the pressure is on and you're in the bottom of the eighth inning and that ground ball is to you, you're going to revert back to what your discipline has made you create.

So to your point, it's not coaching, in my opinion, that's broken. They are not provided the tools necessary, which I would argue are free. Tools like what we have to buy to grow in software, that'll increase exponentially as you scale. Recognizing the discipline gap and actually answering that question doesn't cost anything. And it doesn't even matter the size of the company. So whether you're Oracle or a 10-man sales organization, this is a cadenced, operational, almost military approach to how you drive appropriate sales acumen and delivery. And you do it by not allowing color, not allowing it looks good, I have a gut feeling, evidential, cadenced review, whether it's forecast or pipeline.

And you specifically tell the manager how this is supposed to happen. So they're the first line of defense. I've worked in many companies where the CRO is the first line of defense. It's the CRO that is making all the decisions. It's why I wrote the book. Three to five of the best CROs that I've ever had the chance to work with were always able to ask the right questions. In those QBRs or in those deals that made the meeting stop. Because it wasn't comfortable anymore. It was asking the uncomfortable question when no one was willing to go one step further and ask it. And that's judgment. And I would argue in today's world where everyone has a technology that AI supports, everyone's going to have the same information.

In my opinion, AI creates time for judgment. And it's in those terms, the tonality that you speak in or the way the posture of the person was on the call or how quickly they answered the question or the nuance that seasoned CROs have shared. I stole. I thought, this is incredible. If you can drive that down and breed folks to go, you don't have to figure out how the coach, because we're all expecting every first line manager to ask the same things of the rep every day. They don't answer it. Meeting over. So help me understand one of those things. Because, you know, I call forecast review story time because that's what they are. Right? Like I always say, I always knew a deal wasn't going to close when a rep would start the conversation off with, well, John, let me give you a little background.

Like, as soon as I heard that, I'd be like, fine. Give me context. Yeah, and then I'd have to sift through all the bullshit. And some of my reps were better than others at telling stories. And as a manager, I hated listening to them. And as a rep, I hated coming up with them. Right? So I am wholeheartedly with you on, like, the objectivity. Like, I actually, for a period of time with my team back in the day, I took the words feel and think out of their vocabularies. I'm like, you cannot say the word feel and you cannot say the word think in our forecast review. I want to know what we actually have. Let's talk about the objective components of what we have. And now, then I'll care about what you feel and think.

I didn't really. But at least, you know, I listened to it. So how, A, how do you make it as objective as you talk about? Right? So the subjectivity is out of it. Because that's another piece of this is even if, right, and we can go back to talking generational things here. I think this generation, my experience at least, has a hard time with feedback. Right? And especially because they take it personally. And if they don't think their manager likes them, no matter how good the feedback is, so-and-so doesn't like me. And inherently, it's subjective. So, A, how do you make it objective? And B, what are some of those questions that everybody has to ask and gets uncomfortable with? As an aside, in this book that I'm pulling out, I have field sessions on all of this.

Who to speak to, when to say it, and at what times in the meeting to say these things. But I'll share it in one word because you've taught me this years ago. The word is evidential. Sometimes we validate based on what our rep tells us. We never go one step further to say, what did the customer say? What is the proof from the customer's side that this is legit? Not what you've said you've had. It has to be evidential. If it's not evidential, it's not real. You hear it today. If it's not in Salesforce, it doesn't count. I hate that saying. More important to me, if it's not evidential, don't come to me with something that you think you heard. Not what you heard. What did the customers say? AI actually helps with that.

But you have to have evidence. Remember when you used to do the give-get thing? Yeah, yeah. Still do it. Yeah, yeah. That whole thing is evidential. Yeah. Do I really have something? Actually, what's the key to that? And I'm curious in your perspective on this because, so yes, the give-get scorecard, right? The gives and the gets and what do you have? Now, the way that I used to make that what I call tangible or evidential is through the summary email, right? Where you and I have the conversation at the end. I say, hey, Mark, before we go ahead and do this, I'm going to briefly summarize what I gained and I'm going to send it over to you. Could you email me back to let me know if it's all accurate and if I missed anything, right?

When you say, yes, John, that's accurate, now it's evidential, right? Because now this is you are confirming what we just said. The problem that I've come up with recently is AI has made that summary email a commodity. And so now it's not, it doesn't nearly have as much teeth in it because now it's just, oh, it's this perfect summary email. The client sends it over, the client barely looks at it. So now for me, it's the evidential piece that I look for is like, did they agree to define next step? Do you have a next step like locked in on the calendar? Because I can see that on the calendar. That's one of the questions, absolutely. So where's your head at with like evidence? Like how do we prove evidential on things like, oh, the decision-making process and the timeline and the impact of the problem and all these different things that we have pretty good conversations with.

And the client might even tell us those in the conversations, but then three weeks later, that shit changes because I've never been in a sales environment right now that has been changing so fast that what they told me evidence this week is no longer evidence next week. Well, I mean, the process doesn't change. I mean, this hasn't changed the way we sell. However, what has changed is our ability to literally, I guess the best way to say it is when a rep doesn't have any next step in a conversation, they definitely are not driving the bus, they're riding in the bus. And so it's one of those, what did you used to call it, go-no-go times, where you got to figure out, is this really what it is? We're not ready, even our reps aren't ready, to ask the difficult question to the prospect.

We like easy discoveries. We like when they answer things correctly. But the learning is in the struggle. And I actually think the real deals are won in the uncomfortable question. And that uncomfortable question only happens if you know that you have a champion that's selling on your behalf. And that's ensuring that you recognize that you're attached to the economic buyer. And it's associated with executive priorities. But the uncomfortable question really is trying to pull out urgency, trying to decide, you know, what's the impact of this if you do nothing? Or, you know, that's nuanced. AI doesn't pull out that nuance when sellers have those conversations. But if a rep is hearing that from their manager in deal reviews, I think more times than not, that ramp that we give all reps are because they are making those mistakes that can be course corrected very early.

If we have what I call a disciplined cadence of events that don't allow them to move without these things. I think it's a human disciplined habit that we have failed to provide managers. You can't just tell a manager to go coach. That's not even fair to go coach. But I've had to go, look, you knew how great deals close. What did everyone have in common? These are the five things. Everyone should be asking these five things and have evidential backup for those. And you should have a next step because if you can't drive that train, you're actually being driven. And somebody else is taking charge of that opportunity, probably a competitor. And so that's why I've worked across all managers to go during forecast calls.

Before you sit down with your CRO when you have to do your own, ask these things. These are the things that will determine if it's likely or commit. Don't put commit. How many, I mean, I just had a situation happen today. Somebody was talking about building a business case and they had sent it over. So we have a digital room that we kind of have offering for customers. And I said, so they looked at it in a digital room and they went, well, I didn't make it. I just sent it via email. I went, okay, the big black hole. We have no idea if it was looked at, if it was viewed, if they passed it over to the competition. None of this. But if this was asked like, hey, we're going to have a deal review.

Do you have the room built? Do you have the business case? Did you build it with the champion? Did you validate the number before you had the meeting with the economic buyer? Look, these are standards because they work. They're not standards because they're a process that we want to have. I would never want to process the slowdown and deal. The questions that I put in place or the sessions that we will create as cadences are things that move the deal forward. I have a current CRO who says something like, if you can have five meaningful conversations with customers, you'll reach your number, whatever the quota is. And those meaningful conversations have to be something that moves the deal forward.

And in those conversations, certain things have to be met. And so at times when a manager has eight reps and they're doing deal reviews or forecast calls, it's five minutes a piece. Quick, John, tell me what you got. This is where we are. This is, this looks good. It's illegal. It's having red lines. Well, does it answer the problems that they're solving for? Not sure. Did you ask the question? How, how does this line up with like, you know, standard qualification criteria, MedPic, Bant, whatever, right? Because I, you know, there, there does, there's the other side of this coin of being way too robotic and just looking for those things. So you can check off the box and tell your boss you got those, whether you have them really or not.

Like, you're, you know, it's the, are you the economic buyer? Are, you know, will you be my chance? Yes. Okay. And, and, and they go through, and I've always had a challenge with these, these, these qualification frameworks because they always talk about what we're trying to get from the client, but it never shares what we're giving away to get that stuff, the effort that it takes to those things. So how does the, these like five core questions, right? How does it, how's it different from a coaching standpoint than MedPic or Bant or any of that? It's, it's, it's actually a great question because the discipline gap that I explain is totally different than the MedPics and the Bants or whatever framework.

And they're fantastic because they create rhythms that allow a rep to understand how to move a deal through. These questions are unique. They're different in the fact that it's making the rep have habits that ensure that they're evidentially on par and have less risk of failure through their deal. That's the difference. It's not, hey, let me put MedPic in a first line manager checklist of questions and run through it. That, that would be silly actually, because MedPic is fantastic. Hell, John did it. McMahon did an incredible job building, you know, what, what, what he does. And hell, Sandler did it back in the day. But my point is we're talking about leadership decision-making and leadership decision-making set on expectations that you believe your reps should answer to tend to happen far too late in the deal.

And I want it to be lower in the process because if you can create that discipline with this sort of robotic way of driving to a best practice for a rep, your leaders are open for that judgment that is nowhere to be found in an AI or a framework. It is the opportunity to take a moment to ask that extra question. The questions that every CRO asks when I'm sitting in a deal review with a rep and a manager, and they just flub it each time. Because CROs are thinking about, how can we lose this? It's like prepping for a demo and not understanding what questions might come back from the customer. You have a great demo, but you shit the bed because you don't know how to respond because you didn't take the time to think about it.

CROs are thinking about it all the time and ask the question. I've built that catalog of questions so that it can be answered earlier. We have, we spend far too much time trying to forecast and it, it, it takes so much effort that we lose. I think we're more, more companies are losing in the late stages of sales cycles than ever before because the questions that are being asked that are important don't come to week 11. But if you have it at week two and three and you, and you don't accept optimism, you don't accept anything else. And that's a muscle to be learned. It's a muscle that you have to have every day. That's why a framework or a certification makes sense because that's knowledge base.

You understand what to do, but do you know how to do it when the pressure is most? Let's get back to like, so judgment, um, it goes back to the fundamental question, right? If AI is taking care of all the intro, you know, introductory stuff, then where does, where do the fundamentals come from? Judgment. How do you coach, teach judgment? Because with it, in lieu of experience, experience comes judgment, pattern recognition. Like I can, and that's why I think AI is fantastic for old dogs like us, because we have the context. We've been through the cycles. We can call bullshit on AI and not trust it and know what questions to ask to uncover it and use it the right way. But we have a whole generation of people that have grown up in tech that have grown up without the grind of having to do it and can get the answer at any time.

And so how do you teach, coach, implement judgment? The best way I can answer it is it's the main reason I wrote the book. I stole it from the great CROs that I've worked with and accumulated a catalog of the things that they did. And that judgment now will be able to be used with, at least from the best that I worked with, in those situations that they were able to ask the additional question when it mattered. You can't be trained experience, but you can definitely take what you've learned from the best. And I sat alongside them all in my history to take what I heard from them and put a name on it. And that's why everyone knows, oh, yeah, inspect what you expect. That's an easy thing. Why don't you go ahead and do that?

Well, if it's so easy, why do we continue to lose every quarter, quarter after quarter? It has to be something, right? There has to be something else. It's because it never had a name. I always find that once something has a name, you know how to attack it. It has a name now. And this judgment area is just the thing that AI does not, can't touch yet, right? But it's in that moments of judgment where you make your best decisions. And the sooner you make those judgments, the more likely you're going to have an accurate, I'm not saying increased, you're going to have an accurate view. And there's less sweat with more accuracy than on, you know, wishful thinking, optimism. Yeah, I think the key, and you had said it, I think one of the keys is in judgment is curiosity.

Because I think judgment comes with a lot of experience, right? But curiosity, I think, can be, anybody can be curious to say, you know, to question, like a deal is too good to be true. Well, it's probably, so why is it too good to be true? Like, let's talk about that. What are the things I'm missing here on this deal? And, you know, but it's tough to teach curiosity. And so I've kind of deferred down to interest in the sense that if I can get a rep interested in a company, in a deal, in a whatever, then they become curious. And then that curiosity leads to judgment. And so how are you kind of fostering curiosity from a rep standpoint without the, so that they can develop judgment as they ask more questions, right?

Because obviously the manager front line, okay, they need to, there's rigor to it. There's things that they should be asking on a consistent basis. There's a rhythm to it. But getting the reps to, you know, not just check the boxes and come up with those, you know, route answers because they know they're coming. Because that's the other side of this is, oh, yep, I know my boss is going to ask these things. So I'm going to come up with the answer for that, whether it's manufactured or not. How do you get them to be curious? How do you foster that? You know, that's an interesting question. Let me tell you what I've done at other companies. And it's actually been in partnership with our recruiting teams and how we hire in and characteristics that we have seen in successful reps and how that curiosity is.

Do you teach curiosity? I would argue no. I think there are people who have, I used to call it motor. And I don't mean speed. I just mean they have a motor. They're curious. They're diligent. They want to ask the additional question. It's why bartenders make good reps. They have a tendency to ask all the right questions. But that partnership with recruiting then creates a more exact and more accurate onboarding experience for somebody that's coming on board. I used to have 90-day, like, kind of, I hate to use the term, but come to Jesus moments where you were like, this is where we are. You're being, like, from day one, you are monitored. We're seeing how you advance. Are you doing the things?

So, to come back to your question of curiosity, if I have the right ingredients for my reps, which is a different story, does recruiting do their job and how do they bring in those people? I think only through example do they see what good looks like. Peer learning is 10 times better than my learning. Are you kidding? They'd rather listen to any of them all day long. So, I have to get my best reps to be doing the things that show that this is what lends itself to success and then replicate that. Back it with all the CRO knowledge that I've, not I've, we've, I've bastardized in my lifetime to actually create these things that we all know it's right to do. But in the moment, whether it's easier to do or it's, I got to get, this is the number they're, they're getting me to, I need to hit, et cetera.

That gap isn't a huge things that happens all at once. It's little pieces every time you, you allow something to get by. And that's just not on the, hell, the first line manager. That's on my role, the enablement team. It's on the CRO's pad. You know, it's on everybody and on the rep. But the rep is going to be dictated by what the culture of that rhythm is. This is a rhythm. It changes the culture of what's expected. Rhythm and culture changes businesses exponentially. MedPIC creates an environment or any qualification tool creates those things that make it more efficient for people. I'm not trying to be more efficient. I'm trying to be more accurate. I want to, I want to, a CRO would say, I'd rather see what's real.

Then be fooled every quarter. And if we could have stopped it in week two rather than week 12, we should do that. And it costs nothing. And everyone will say, yeah, that's right. That's what we should do. That's, let's go do it. Come on. Two weeks later, the thumb's on the, you know, on the number and people will stop. They'll just revert. You can't. And the only way that changes is if you break it down and do it again and don't accept anything less. And that's for the lifetime of the business. You look at the successful companies. You know, you work there. You were at Salesforce. You get it. I mean, when you have a discipline combined with a culture that that's the expectation, they're weeded out very quickly.

And, and, and look, there are good reps all over the place, but why is it that only 20% of the reps are making their number? What are the other 80% doing? We're giving the company a chance to, to, um, set the expectation higher sooner. Um, I always tell my, my students, onboarding should never train you to the floor. You should be trained to the ceiling and the expectation should be 10 times more. And I should be 10 times harder on you so that when you're out there, you can have that badge of courage that said, yeah, I, I ran through Mark's program. It was a pain in the ass, but thank goodness, because I have this now. Yeah. It's funny. Like Tom Brady says that, uh, that him and Bill Belichick in the heydays, they, you know, Monday, Monday through Friday were hell right for them.

So that Sunday would be easy. Right. Cause where most other people like, oh no, Sunday's game time. Like I'm, I'm, I'm amped up. Let's, you know, let's chill this week and let's make sure that we get our stuff together and, and, you know, not, you know, not have to hurt ourselves. Don't practice too hard. And they practice 10 times harder than they played because by the time they played, it was like, okay, yep. We've seen this before. I got this. I've hit every single thing. I've gotten the shit kicked out of me for a week and now it's easy to play games. Well, similarly, when I was playing college baseball and after I'd get hit 500 ground balls a day from 20 feet away, bullets at shortstop bullets.

So my muscle memory was immediate. Didn't matter the time. I didn't have to guess the footwork. Didn't have to guess anything. Why did that happen? Why was that correct? Because they set a standard. They held to that standard. Didn't accept anything less. I think that's why we laugh at it, but that's why sports are the best examples of successful organization. Because of that, there's no settling. You don't give. Everyone has their role and you go about doing that. If it can be done at that level, the muscle memory should take over for itself. Let's talk about the AI factor here, right? Because you have a line, I think, in the book. It says, AI can prepare the hitter, but it still can't take the at-bat, right?

And so there's a yes and component to this because AI is starting to take some at-bats, man. Like it's like you even said it earlier. It's like yet, right? It can't do this yet. So with this rigor, right? Somebody, I had a podcast, I forget who it was, just Dr. Gleb, who has done a ton of research on AI and the impact. And I had the question of like, where do the fundamentals come from? Because all the grind and the shit work that I did is now being taken over by AI. And he goes, well, if you really think about it, like all that grind and shit work, like the vast majority of it was just shit work. Like there was 20%, there's about 10 to 20% of that work that was really valid, right? For you to do that gave you the context.

But the rest of it was just dog shit work, right? Like research, all these different things. So he's like, what every company shouldn't do is figure out what that 20% is, you know, go all in on that and then automate everything else, right? So where are you with where the line is of AI and what it should do for reps and what reps need to, and how they need to use it so that they don't, they don't outsource their thinking to it. They don't outsource their, you know, the responses. Because my whole thing, you know, we've gone from the search engine to an answer engine and that's a dangerous thing for people that are lazy. And unfortunately, the vast majority of people are lazy. And so what's the line of leveraging AI and how do we use it to create the discipline that you're talking about, to create that rhythm that you're talking about?

Well, AI, who said it? It might've been John McMahon. He used to say there's this thing called the seller's deficit disorder, where every customer has a belief that has been true for 50 years, they don't trust you and they think you don't know their business. And so given that AI can bring all the contextual things and potential next steps, they cannot deliver it. It cannot be delivered because we're still in a human to human selling experience to some level, regardless of how much they've looked and did their investigation for the first 70% of this, of their cycles, not even ours yet. You have to deliver it. And that only is based on the trust that you've built with that customer. And so I love that AI provides everything, but in this AI world where everyone will have that information, will have all of that, how do you deliver that in the best way?

The best way is how we think deals should be structured and managed. It's why every day, you probably do it with your reps. When you talk to a customer and you see they're a little bit engaged and there seems to be a potential thing here. Hey, when I work with customers like yourselves, the way we are, we seem to be successful together is if we create a mutual close band and we do this and we do that. Well, it's again, it's, it's open for you to be better at your craft. You take time to prepare better for that call. Heck, you were, you were smart. You were, you were ahead even when you just had LinkedIn to spend 10 minutes, you were ready for a call and can deliver. But with AI, I have the players, I have the calls, what people said, but there still is preparation and how do we kind of, Hey, this is what we heard.

Anything changed since we last got together? All those other things, but we, we prep for what we're going to do next. Not what we're going to do today. That AI is helping us with what we have today. And I love that it provides reps and the team of folks, because there are SEs involved with this, you know, customer success at times. You can plan accordingly and you plan it the best on the way we see every company is different, how they sell accordingly. So AI, fantastic, but everyone's going to get it, but they will not, everyone's different in their delivery of doing it. There are people who know how to ask the question, when to do it. And this is why I've taken it from the, the highest level in the organization.

I want to know as a rep, the CRO questions to ask. I don't have, I don't have time in a, in a world where I only get a certain amount of moments in, you know, to provide something that AI has not. It isn't canned that. And that's the thing. It's like, I tell any rep who doesn't think they're in trouble with this stuff is, you know, do yourself a favor, go into AI and pretend like you're a customer and, or a potential customer and just, you know, didn't ask the question. Like for me, I'd go in, I'm like, I'm a VP of sales of a 50 person sales team. I got 20 SDRs. I got 30 AEs. I'm looking at the JV sales sales training. Tell me what I need to know. How does it compare against the other top three vendors?

How does this align with my strategy? And when you realize in a five minute conversation, you get more info than some dipshit little 22 year old kid who's going to ask you Bant questions and then flip you over. Like it's, it's not the AI tools that are going to take over sales. It's when the client wakes up and realizes the value that we bring is not that much for the most part. I think we have to be careful there because what happens then we forget we're there to solve the customer's challenge. We are not trying to sell them anything. We're trying to help them make better buying decisions. And if, if I built a trust that I'm supposed to, and that customer is as up to speed as you suggest in that example, I have to be extremely credible and serious about how this helps them.

And the questions I ask them are only driven from what we believe is going to solve their problem. Because I guess they have checklists themselves, right? They have a budget, they have a number, but I'm telling you, I have found historically, even though in most recently, but the last two companies I've been with where AI has really been taking off. It's still the reps who know what to ask that decides it. Right. I couldn't agree with you more. My, the, the only, you know, this goes back to my optimism, pessimism of AI. You know, I am, like I said earlier, I am insanely optimistic for creators right now, for people who are curious, because if you are curious and you're a creator, oh my God, the world is open to you.

You can, you can build and do whatever you want to do. Um, but if you're not, this is going to be a tough road for you. And, and unfortunately, I think we're living in Pareto's principle right now. And I am going to be very generous with Pareto's principle here on the 20%. The 20% are the ones that have the judgment that, that do know the questions to ask that are curious, right? But there's a, there's a very large part of our population that are not curious that go through the motions and quite frankly, not even to their own fault. I mean, they're, they're, they've been put into a process. I mean, it's like everybody always argues and yells at the, you know, the trophy generation, all these kids and, well, who gave them the fucking trophies?

We did. You know what I mean? So it's, it's our fault that we created this mess. And, and I think there's a generation of sales professionals that are just like, yep. Okay. Let me ask these questions, check that box. And I just had a great experience of it. Not a great, I had the, one of the worst sales experiences I've had last week was Salesforce and Cloudforce. It was honestly that like, there was zero need for a human to be involved in that. And I had to wait a week and a half to get an answer that I didn't even want. It was, it was such an awful experience that, and it tells me like, okay, on two, I was actually, I was somewhat optimistic actually after that experience. Cause on one side, you'd think that a company like Salesforce would Cloudforce and everything like that.

Like they'd be leading the way. Well, AI is nowhere near where it needs to be if they are right. Cause that process was ridiculous on the flip side, you know, so therefore sales reps are still like, okay. But then on the flip side, the sales rep that just went through the motions, didn't even ask me a question. Just gave me a, like, don't you think that they're look, you've lived it and I've lived it in the past and sales techniques are kind of like the way the classroom is today. It hasn't changed in 25, 30 years. And in a era when software was coming into its own and established itself as the standard, all you needed was a great product. You could show up, do the niceties. Don't, don't stub your toe.

And then you got a 40% chance of closing the business and hire enough reps and get enough equity capital. You can get ahead of it. Oh, wait, you mean we have to make income as well. There needs to be a bottom line to this. Oh, profit matters. Right. But right. It's changed now. Maybe not that long ago, five years ago, PE firms were looking at growth. Now they're looking at- Right. I remember it well. That's what happened when it came to a screeching halt for me. I remember, I actually remember the day it happened. Well, yes. And so if we're improving the technology, shouldn't we improve this profession? This idea that says there's, there's a human actionable step that can't be replaced by AI.

And you better do it in the best light because those that will, will succeed. And if a company wants to see it, why not establish that standard? This is how we roll. Period. And it's not do it or, or else that's an ultimate goal in all of this, maybe, but, but it's a standard you, you live by. Again, this discipline gap that, you know, I call it an operating system, but it's really just a rhythm that suggests we are going to attack and partner with customers and be there. What, honest uncle? I'm going to ask the question that mom or dad wouldn't ask, you know, like, come on, what are we doing here? I mean, you can, you have a bunch of choices. What I understand is here is your use case. Let me show you how we can solve that.

Let's ensure that we are level setting using all the great things that you've trained in your, your past and all the other great frameworks and certifications. Again, which are great. This doesn't replace any of that. But I am defining something and driving something. No one has spent the time to take it seriously. And it's not just generic, go coach them. It's not just generic, inspect the deal to ensure. It's asking the right questions based on really mature, smart people who have grown the largest companies that we've known in our lifetime, who asked the questions late. That made everything stop. Let's bring it down a level because I do believe without guidance, first line managers would just want to move up to the next level because it's just a difficult thing.

So it's not coach or be let go. It's coach based on this framework that allows you in the skill set that I've determined that make you a director or a first line manager able to handle this responsibility. Because if a 3% improvement creates $15 million of revenue, I don't need to have 10 hero sellers. I can have a system that scales. That's why those adages, what got you here, what got you there, make sense. Because up to the first $100,000, you know, it's the product. Between $100,000 and $250,000, it's the product with some fancy service and embellishment. But you get to a billion, now you've got to separate yourself. There is professionalism. And you, more than anyone in our industry, probably preaches this idea of a professional seller.

We complain that we don't want to be vendors. We want to be professional sellers. Well, act that way. There's a new definition of what it takes to be in this role. We were lucky. We could go in at certain times and make a very nice living comparative outside our bubble. And I'm practical enough to know, as a child, what it was like with a guy that worked a lathe machine for 45 hours a week. That knowledge doesn't, you know, doesn't get passed down. I've been lucky enough to work with, I mean, really good people at Sprinkler, at Drift, at Marketo, at Demandbase. And these guys took the time, because I was, what's the, consigliere, this is what I'm trying to capture, Mark. This is the things that, why am I the one that, why am I here as the last defense before this goes up?

We can't commit this number. It has to be asked sooner. And I just think there are steps for that. All right. So let's finish on this. And from coming from the book, if you could force one weekly habit on every revenue leader right now listening, and it, you know, with no tech, with no rollout plan or whatever it is, like, what would that, if you could force it, the one weekly habit, what would it be? It would have a cadenced deal review process for your reps. And what's the one question that you think is one of the more, if you got like five, you said, you know, things that you ask, what's the one question that for you really helps determine if the deal is real or not? What's the business problem we're solving for?

You can get economic buyer, you can get budget, you can get all the, what are we solving for? And no marketing answer. Use the customer's language. What did they say? What are we solving for? And then that person who asked it in a position to know. Does he have the most pain? Well, that's why, like, one of the ones that I, we tested this out with my team a while back and, you know, because we test questions and, you know, everybody asked one question this week just to see what happens. And we got to the impact scenario. And what I, what I realized was we were asking the standard question of like, what's your decision timeline, right? That's always, what's your decision timeline? I realized I don't give a rat's ass what the decision timeline is.

I couldn't give a shit. Like, what's the go live date? What is the go live date on this? There's, there's three questions I ask in succession. What's the go live date? Why does it need to go live that date? And what's the impact of the business if it doesn't go live by that date? Those three answers dictated our forecast. Because if there was no impact, if they didn't go by a certain date, I said, leave it on the pipeline all you want, but do not forecast that deal. And that, those, the, the, the three indicators for me were those three questions. Did you have a defined next step on the calendar scheduled? And have you met with power? At least somebody, they don't have to be the decision maker, but they were executive enough to be a champion and fight for you.

And you didn't even have to make them your champion, quite frankly. You just had to at least have an audience with somebody that was at the top who was, who was going to dictate one way. Those things, those questions and those two things was pretty much, if they were there in the forecast review, we closed like 90 plus percent of those deals. If they weren't, we were at a 32% close rate. We, we, we went one step further. We wanted three influential people in the account at certain levels of the business, financial, business, and IT. And if you had those three, that was something. And the next step was something scheduled in the calendar. We went one step further. Was it accepted? Did you send, didn't you send an agenda?

Did you tell them what the objective of the, of the meeting was? We, I, I, I, I work with someone now and, and, um, he'd probably be embarrassed if I said this, but he's a huge fan of spin. Spin selling is his, and the thing that I got most out of his, his, uh, his lectures to me, because I was like, spin, are you really sold? He goes, implication, Mark. It's always about implication. Everyone's really good about understanding the situation and the problem. They have no idea. A rep has no idea how to frame an implication question that leads to the need payoff. Oh, what's the implication of X? Let's say I was able to correct that implication. What would that mean to your, you know what I'm saying?

That's just an example, but no one asks those. Well, it's the same thing with like Bant, right? Like, I don't give a shit about budget. I don't give a shit about timeline. I don't give a shit about authority. I only care about need because if there is a genuine need there and there's a problem that you are trying to solve, I can, I can find budget. I should be able to get to power and I should be able to expedite a timeline. But if there's no need, if there's no real concrete problem, impact, all that stuff, then the rest of that stuff doesn't matter. And so, like, that's why I look at all these frameworks and say there's, okay, there's one piece of that that I agree with. Other stuff is great.

You can, you know, if you get it, fine. But there's always that kind of exit, and we talk about this in sales stages in the sense that there's, you know, there's always that one exit criteria to move to the next level. You don't have to get everything at all the different stages, but there's usually that one that if you don't get that, it does not get to go into commit stage. And I think those are the ones that we need to highlight for people to say, like, and learn from to say, hey, let's analyze all these deals and let's watch what the accelerators and decelerators are, right? Because there's definitely things that once you get them, they accelerate deals really fast. And there's other ones that if you don't get them, they kill deals almost immediately.

And we've got to figure out what those are. And I think AI is actually a great tool for that these days because it can analyze it better than anybody else ever has been able to. I used to have an old saying that you have to move slowly to go fast, which meant that if you could spend most of your time on the front side of a deal and iron out those things that are necessary to progress it, those forecast calls become much less stressful because there's some reality and trust in the number. And I'm trying to gather those things that will allow organizations to scale in their reality, not to scale to always come back to go, we missed again, or we weren't there again. And that's powerful when you see it occur.

And I don't, you know, at some point we'll get enough data that will allow that to occur. But in this mid kind of spot, this is a very, I think it's a big opportunity, not just for first line managers. This is something, this is a, like I wrote this book purposely to be like something I would talk to a CRO about over a drink. No fluff, no anything. It's for the enablement person who understands the real deal and all this and doesn't have the power level to make it happen. You know, I've lived their life. I understand where they sit. And then ultimately the first line manager, if they want a power opportunity to separate themselves from others, a rhythm or a rhythm beyond the cadence calls, there is a rhythm, and I talk about it in the book, of a variety of four different things you do.

So if I explain the problem, tell what this cadence rhythm solves for. And then more importantly, the biggest thing, which we haven't really touched base on yet, is what happens when the system doesn't give you the answer? That's the gray. And that's the judgment part that I'm trying to share here. It's that judgment that comes down from the CRO that I've captured that says, you know what? These guys knew what to ask. You know, you know, now with AI, that judgment should be allowed further down much more quickly. I mean, we've always known what's best to do, and if you've found from the best, I don't take hardly any credit. I was part of that, and I was successful with it because I was with some smart people, but you pay it forward.

I mean, at the end of the day, this thing I'm rolling out is more for me than for anybody else. I just enjoy this idea of, I wish I had this when I was, you know, working my way through sales. And we'll end on that because, you know, the thing that I, you know, the older I get, the more like, oh, my dad, you know, I feel like talking about my dad. But, you know, right now, judgment should be at a premium. And I see all these young tech bros start up, you know, and they're discounting. You know, the ageism is real. You know, I talk to a lot of people who are my age now, and thank God I have my own company, and, you know, I do my own thing. But, you know, there's a lot of people that I know that have so much knowledge and experience that is gold in the world of AI because it is that judgment layer that says, okay, yeah, you can have all your agents doing all this crazy shit, but here's why that's not going to land with a client.

Here's why we need to use it this way. And they're still relying on kids who are uneducated and don't have the experience and have no judgment, but they're, you know, hey, let's go. And there's a balance here of using this knowledge and judgment. And what you're doing with this book is hopefully translating that to the younger generation so that they can skip a few steps, not have to skip them all. They still got to go through the pain, but learn from the experience because I would pay up. If I was hiring right now, I would be paying a premium for senior experienced people with judgment. But, you know, we're just not a society that rewards that here in the United States. Well, if you're worried about age bias, how about me?

Yeah, trust me, man. Like I hit 50 and, you know, 50 is a weird milestone, as you know, right? It's like you're at that, like, holy shit. Like when I was 30, I thought 50 was ancient, you know what I mean? And now I'm at 50 and I'm like, wait a minute, I don't feel like as old as, like, I feel like I'm still like 30, right? But there is that, the point where you get to in your career where you like, you know, pattern recognition and I've seen this before and here we go again. And that is just so, I wish we were different as a society because there's other societies that praise age. You know, you ever know that, the challenge where if you're on a boat with your daughter, your wife, or your mom, and you can only save one, and every society does it different.

Like here in the United States, you're saving your kid, period, right? Because the kid hasn't had a chance to go. But if you go to Asia, they save the grandparents, like period. Like screw the kid, the kid's going to die, we can have another kid. But like, you know, they value experience. And so I just wish we would, and I had to learn this at an early age too, because I remember this one quick story where my buddy who had Patriots tickets, you know, seen, I've taken his, you know, his season tickets and his dad had them since the 70s. And his dad was sat there every tailgate. We would go every single Sunday and he would just sit there, Joe, he would sit there with his, you know, his newspaper and read while we drank and got hammered and threw the football around, right?

And then unfortunately he passed away and I read his obituary and I looked at his obituary and I almost started crying because this man, he had started three venture capital companies. He had been startups. He had, he had run a small business. He had done all these things and I'm like, holy shit. If I had taken 30 minutes during my drunken stupor every Sunday to just sit down with him and pick his brain about business, about investment, about this, like the knowledge that I would have been able to gain from that man. But he was my buddy's dad, Joe, what's going, you know what I mean? And I just, we got to learn from this experience because I personally think we're going way too fast right now.

And the inexperience is running a fucking train straight off of a cliff right now. And, and it's scaring the shit out of me, quite frankly. Well, well, I'll tell you lastly, before, before we go, in essence, what this book will do is bring that experience to as much a CRO as it does to a first line manager. CROs have so much pressure on them that many of us have no idea. And I've sat next to many, um, where the impression is far different than what's reality. And to have what I'd call a little black book that would help kind of kickstart a rhythm or a cadence for the organization. I think they would have liked to had that. Or a little gray book, if you will. Yes. Awesome. Well, tell, tell people when it's coming out where they can find out more information and all the fun stuff.

Yeah, it'll be coming out. I'm going to be teasing a little bit more on LinkedIn. It'll be out, um, October pre Halloween, I think will be the time. And so just excited. It'll be out on all the things, whether Barnes and Noble, it'll be out on Amazon. It'll be in paperback. It'll, it'll have a nice forward in it. Um, we'll be excited. Um, and, uh, I, I just, uh, you know, I just, uh, hope some of my friends read it. And then me too. And then they should. And, uh, and like, so we'll put this out around that time. So everybody go out and get that book. And again, I think you can, you know, there's a certain amount of judgment that you just have to live to, to, to gain. But there's, there's, there's a lot we can learn from the people who've been there before.

And so I'm hoping that a lot of the younger, uh, generation and even older generation learns from this. And, you know, like I said, you know, can skip a few steps, not all of them, but skip a few and, and, and try to expedite where they're going right now. Cause we're moving faster than ever. Well, this has been great. I do appreciate it. You've always been kind to me. So. Yeah, absolutely. And everybody, um, you know, like I always say at the end of all these podcasts, go out there and make somebody smile today. Cause no matter how bad your day is going or how bad you think it went, if you make somebody smile today, you know, you had a good day and the world needs a lot more of that right now.

So thank you all very much. And I will see you on the other side. Hey, thanks again for listening to the show and for all your support throughout the years. This is one last reminder to check out my training programs at jbarrows.com or leave a five-star review on your favorite podcast platform or G2. If you've already gone through my training or sign up for my newsletter, any of those will help ensure I can continue to bring you free content. And great conversations like the ones you just heard without having to annoy you with sponsors. Again, let's make it happen in 2026 together.