179. Sales Mastery & Storytelling at Scaling Startups (Craig Wortmann)

179. Sales Mastery & Storytelling at Scaling Startups (Craig Wortmann)

Craig Wortmann of Sales Engine joins Nick to discuss Sales Mastery & Storytelling at Scaling Startups. In this episode, we cover:

  • Craig’s background and how he became involved in the early stage tech community.
  • You’ve spent a lot of time looking at how companies make this difficult transition from the scrappy, do-it-all world of “Entrepreneurial Selling” to a “Professional Selling” organization. Talk to us about what you’ve observed and how companies struggle in this transition.
  • When is the right time to transition from ‘guerilla selling’ to a more organized, professional process?
  • When we had Tae Hee Nahm on the program he talked about three different types of sales leaders at different stages of a startup. At the beginning it was a Davey Crocket- like character, an independent explorer who will find their own path through the wilderness… then at the growth stage, Braveheart character- someone with that warrior spirit and finally at the scale stage he looks for the Dwight Eisenhower– someone with political savvy to align all the sales folks and move in the right direction… do you agree or disagree and how does your philosophy differ?
  • What do you do when a top performing sales person won’t use the tools, align with the culture or conform to processes.
  • How do you handle it when the product is broken… it’s clear that the offering is lacking and the issue is not with sales.
  • Situations where selling something that doesn’t exist
  • Storytelling… I see founders fail at this often and even I often failed in telling my story when raising Fund I. Where do most people go wrong?
  • What’s the story canvas and how should it best be used?
  • You talk about how folks should think about ‘capturing, distilling, and telling’ the right story at the right time for the right reasons. What’s your advice here?
  • One of the more popular things you teach at Kellogg is called the ‘The Perfect Sales Meeting”. Can you talk to us about how one should think, plan and increase their sales meeting effectiveness?
  • Between sales meetings or when a prospect is slow to make a decision… how does one create urgency and positive momentum toward a decision?

Guest Links:

Key Takeaways:

  • Craig outlines the differences between the “wonderful chaos” of Entrepreneurial Selling and the systematic approach of Professional Selling.
  • High performance sales stands on 3 mains pillars, Knowledge, Skill and Discipline. 
  • Craig characterizes Entrepreneurial Selling as high in knowledge but often times low in skill and discipline. At Sales Engine they work to translate that knowledge into skill and discipline to develop a repeatable sales process. 
  • Craig emphasizes, knowing how to structure a conversation is just as important as knowing what you’re going to say. He shares his process of creating a “Toolkit” that can be applied to build the framework of specific conversations. 
  • Craig defines the tools in his “Toolkit” as the specific ways you speak about yourself, or your business during a cold sales conversation. 
  • One mistake Craig has made and entrepreneurs frequently make is hiring talented sales people before having a sales process outlined with an understanding of how to apply it. 
  • Teaching your sales team how to handle difficult situations through role-play and giving real constructive feedback supports the growth of a strong sales culture. Role play is central to what they advocate at Sales Engine because it strengthens discipline when faced with objections in real life. 
  • The “Sales Sprint” is a technique Craig uses that has successfully helped companies rebuild and grow their pipelines. He dives into the methods he uses to keep a team motivated during the intensity of these sprints.  
  • In situations where the product is not yet ready to go to market, Craig advises to sell on the service of your team, ask qualifying questions early in the discussion and maintain full transparency about the product and it’s progress. 
  • Craig teaches a class at Kellogg called “How to Get People to Not Only Like You but Love you” that highlights the idea of selling yourself and building trust as a way to draw people to your product. He applies this methodology specifically to companies trying to sell a product that is not yet created. 
  • High performing salespeople are great story tellers but often don’t have enough of stories. Craig shares how he collects stories with a 3 step process, that allows him to apply specific stories in situations where they are most effective. 
  • The Story Canvas is a tool Craig developed that guides you in creating the architecture and emotional arch within the story.
  • Another tool Craig has developed is The Story Matrix, a spreadsheet that allows you to organize your stories by the situations in which they are appropriate and will be most effective.
  • The 7 disciplines needed for The Perfect Sales Meeting are being clear on the 3 main points of the meeting, “the purpose benefit check”, endorsements, pivot, closing effectively, ending early and following your shot. Craig goes into detail about each of these disciplines and why they are important.  
  • Craig states that stories are raw power and influence because of they’re ability to touch the emotions. 

Transcribed with AI:

welcome to the podcast about investing in startups, where existing investors can learn how to get the best deal possible. And those that have never before invested in startups can learn the keys to success from the venture experts. Your host is Nick Moran and this is the full ratchet

Welcome back to TFR today the high performance sales and entrepreneurship coach Craig Wortmann joins us. Greg is the founder and CEO of sales engine, a tools and services firm focused on sales growth of middle market companies. He is also a venture partner at Pritzker group venture capital, a Chicago based venture firm investing in series A and B market leading technologies companies. In today’s sales centric interview, we discuss the transition from scrappy guerrilla selling to professional selling where company’s sales processes fall down. The profiles of sales leaders at different stages of a startups growth, how to handle productive but non compliant sales folks, what to do when the product or service is broken, not the sales process, how to deal with sales folks that sell something that doesn’t yet exist. We talk about the value of storytelling and review Craig story Canvas, we review the key elements of executing the perfect sales meeting. And we finish up with Craig’s advice on reigniting momentum with prospects that have gone cold. Here’s the interview with tech sales guru Craig Wartman.

Greg Wartman joins us today from Chicago. Craig is the founder and CEO of sales engine, a tools and services firm focused on building and fine tuning the sales engine of middle market companies. Greg is also a venture partner at Pritzker group venture capital, a Chicago based venture firm with investments in Casper, the Honest Company, matte box and many others. He’s a professor of entrepreneurship at Northwestern University’s Kellogg School of Management, and the founder of the new Kellogg sales institute, where he developed the award winning course called entrepreneurial selling, ranked by Inc Magazine as one of the top 10 courses in the country. And of course, he wrote the book on entrepreneurial and professional selling, what’s your story, using stories to ignite performance and be more successful? Greg, I know you’re quite busy working with some of the leading tech companies in the world. I appreciate you spending some time with us today. Nick, thank you for having me. I am super excited to have this conversation, as am I so tell us your your background and your stories, sort of, you know, how did this path lead to working with startups and working in venture? Sure it’s, it’s a bit of a circuitous path, I really got my start. It wasn’t my first official job, Nick. But I got my start at IBM. I covered 13 zip codes on the south side of Chicago for IBM i was what was commonly referred to as a tip of the spear salesperson. And I sold a product line that’s still actually around all these many years later called the as 400. And I had a manufacturing and distribution territory. So it was I look back with fondness at those years, it was wonderful, terrorizing a little bit of chaos. And what I look back now with some Hindsight is IBM did me a really, really great service. They taught me how to sell and be unafraid and to walk into a room and talk to people. And it sounds kind of overly simplistic. I am forever thankful for that experience. It’s been. I mean, that’s what really got me going that has led to all these crazy fun things that I get to do. The big second pivot for me was in the late 90s. Starting helping start my first business I was not the original founder. But I came in soon after I got started to try to commercialize some technology and spent some years there with a few different businesses and entrepreneurship and got very interested in, in tech and in the growth patterns of young companies. And then third big pivot, I guess, would be getting the opportunity to teach I’m, again forever thankful to Chicago Booth, they gave me my first chance to teach and now I’ve moved that practice to Kellogg, but it’s you know, I love both places. So it’s a lot of fun to see and experience and experiment with these things from different with different hats on. That’s great. What industry or sector was the startup in?

It was

I laughed because it well, I thought it was a SaaS company, which back in the day, you know, before the word the phrase SAS was invented. We call them application service providers. We thought it was that and what we ended up with was a consulting firm, which of course, in the venture business is not that’s not a great plan B to land on. It ended up working but it was a software company in the SAS business. And then I got a chance a really fun opportunity. Again, scary but fun to turn around a digital marketing agency in Chicago about 10 years ago now

Wow, okay, you’ve done it all. So when did the expertise sort of coalesce around sales? And when did you begin sales engine and really proactively teaching and working with tech companies.

It was right on the heels, Nick of that second company, what I sort of considered my second company, my second entrepreneurial venture, we had this digital marketing agency. And the realization that smacked me in the head as I got in there and sort of unpacked the issues that this turnaround was facing was that they didn’t have what I consider to call now a sales engine. They’re just they’re amazing people, a good product, not clear positioning, but they were doing the job. But they just couldn’t, they didn’t sell. I just got super interested as a career salesperson, mostly. I just thought, okay, maybe this is something I can help. And we got about the work of building a sales engine. And at some point, I literally, was having a glass of wine with my wife, who’s also a Kellogg grad and talking it over with her. And I said, we were sort of midstream in the company. And I said, you know, I just want to do this. And she said, What do you mean, what’s this, and I said, I just want to build, I just want to help companies build sales engines, that’s what I want to do. It’s super fascinating. I can’t find the bottom of it. And it’s, you know, it’s hard, which also makes it interesting. And that was what led me to about a year later, we sold that company, and I started sales engine, which that’s just what we’ve done, over and over big and small, really successfully, some not as successfully, but mostly gotten really good results for the last 10 years. So that’s where it really started it started in, call it 2008 2009. Great, great. I want to drill into this here, you know, I’ve got got a number of portfolio companies, they have a b2b enterprise SaaS offering. And they’re going through this transition, right from being an early fledgling company, scratching out some sales to more of a legitimate growth company with more of a sales engine, no pun intended. And I know that you’ve spent a lot of time looking at how companies make this transition from sort of the scrappy do it all world of entrepreneurial selling to more of a professional selling organization. So can you start off by talking about, you know, what you’ve observed and how companies struggle during this transition?

I sure will. And I’ll try to be concise about this. I call this transition that you’re articulating, Nick, the transition from entrepreneurial selling, to professional selling, and the way I describe the differences entrepreneurial selling is, and I have little phrases for all this stuff, just because I’ve been working on saying it concisely, the wonderful chaos from time zero to breakeven, where you’re figuring everything out at once. So you’re raising money, you’re figuring out the product, you’re figuring out whether you’ve got product market fit, you’re trying to, you know, stand up an online presence, you’re trying to get out in the world and tell your story. There’s this swirl of chaos around it. And I call it wonderful chaos, because it is wonderful. On some level. It’s yours. It’s your baby. It’s also chaotic and stressful as we all it’s we all well know. Yes. And there’s this just this sort of swirl around that. And then completely change your mindset. Now walk into an established professional selling firm, IBM, now Google, Oracle, any of those, you know, any the bigs, right, Salesforce, and you’ve got systems and processes and a hiring pipeline and a profile sales tools and technologies to support you and all that stuff exists. And the question that I love, and I just never get tired of exploring is how do you go from one to the other? How do you make this transition? Weirdly, I went backwards in my career. So I started as part of the IBM army, you know, which I’ve said, I’m super proud of and learned a ton. And then I thought, Okay, I’m going to start my first Sass company in 1999 2000 Crappy timing on my part, by the way, and I started this company, and I took a seductive, and I will admit, perhaps arrogant sort of attitude into that, or mindset, rather into that first company. I said, Well, I don’t know a lot about software, but I know how to sell. Turns out I was wrong. And what I mean by that is, I came from this professionalized amazing, large supported sales force into this chaos on my first company that I actually learned that I didn’t know how to sell and I don’t mean that literally, I mean, you know, I was fine in a meeting, I could hold my own, I knew how to sell. But when you take away the brand, and you take away the product, and you take away all the support, it gets really, really difficult. And so I experienced this transition in reverse. And of course, that’s what got me interested in thinking okay, well then how do I actually help companies cross this bridge? So

Let me pause there. Does that make sense? Yeah, it does. It does. I’m curious, what are some of those primary differences and maybe profile of the early folks that are just trying to get their first sales and these robust systematic organizations that, that have their pipeline down to a science?

Yeah. Well, interesting. You alluded to the answer in your question. So let me articulate this. So, or unpack it a little bit.

I strongly believe that highperformance selling stands on a really simple but powerful foundation of three things, knowledge, skill, and discipline. And as I’ve been thinking about this for a while now, and trying to teach it, I think entrepreneurial selling is best characterized by high knowledge. What I mean is, you and I are, you know, we started tech company, Nick and Craig. And we walk into Kraft trying to sell this food science tech company or sell our product to craft or whoever. And it’s a high knowledge sale in the sense that because the product doesn’t have edges yet, and the brand doesn’t have edges, we have to be really knowledgeable in how that product might work and fit inside craft. And there’s nothing wrong with that. But as we see entrepreneurial companies grow, and acquire their first customers, what worries me, and what we work on at sales engine is translating that knowledge into skill and discipline. And I can define these terms, but the knowledge is all the things you need to know, you know, where does Nick and Craig’s company fit in the market? What’s our value proposition? How might it work for craft or another client, et cetera, et cetera, all those things are super important. I’m not disparaging knowledge. But unless we can do that, with skill and discipline, over and over, it never becomes a repeatable sales process. And we see this at Pritzker group, I see it in my own practice. I see it at Kellogg, when students come out, I mean, over and over, we see it lag, entrepreneurs take way too much time to translate this into sales, tools, skills and disciplines. You know, my sort of provocative point of view here that I try to shake entrepreneurs with is, you have too much knowledge, that always starts a really interesting conversation I love to have with entrepreneurs, because they kind of go, you know, you’re out of your mind. And I’ll say, I don’t literally mean, I don’t mean get dumber, what I mean is, are you as conscious when you walk into craft, are Nick and Craig as conscious of the skills that they need to apply in that moment, and the disciplines, otherwise known as choices that they have to make in that moment, as they are knowledge. And if you think about a professionalized Salesforce, you know, one of the things one of the great gifts I got from IBM is they just made us do roleplay, over and over and over again, that’s discipline and skill, it’s not knowledge, you’ll learn it the first day. But 35 days later, you’re still applying it that over and over. And that repetitive deliberate practice, is what yields skill and discipline. So you become this is why I use this metaphor, build in tune your sales engine, but tuning is the repeated skill and discipline. And that’s what we see missing. But I’m so I get so excited helping companies try to help them transition there. Yeah, so I’ll have startup founders selling me often we run an early stage fund. So we’re not a customer, but they’re, they’re pitching us for capital, you know, the knowledge issue certainly can get in their way, particularly with deeply technical founders, you know, we can go down a rabbit hole for over an hour on some esoteric technical competencies are specific features that might apply to certain clients and not others. But it’s very easy. I think, at times for me to get lost in the discussion when it gets to this level, when it gets to maybe a too detailed level, especially when that’s led by the founder, when the founder kind of goes down these rabbit holes on their own, unsolicited by questions. Yeah, so a I totally agree. Be I think that’s the fault of the entrepreneur, if you’re lost, because believe me, Nick, I’m lost in these conversations to week by week, I find myself lost. So be that’s not your fault. That’s the entrepreneurs fault. And then, you know, what you just said is I’m not only lost, but you know, what’s the question I should be asking? Or what’s the question that they’re asking? The ability to ask the right question at the right time. It’s actually a skill. It’s based on knowledge, but it’s a skill. So if you think about it, you know, the entrepreneur, the best entrepreneurs are the ones who are deeply technical. But they’ll say, Hey, Nick, let me take a moment and describe some of the nuances of this product. Now. The minute I am blurring the lines or this is too complex, stop me. And I’m going to try to do a good job of sort of reading your body language and I will stop and I will ask you a question. Just that little, I would argue that

Just that little discipline of warning you that that’s how you’re going to structure the next minute or two of this conversation. If I’m trying to raise money from you, has a huge implication for how you receive me and my credibility. And just notice something that credibility doesn’t come from expertise. I haven’t said anything yet. I haven’t said anything about the technology yet. I’ve just said, here’s how I’m going to do this. Is that okay? Setting up sort of the the framework for the discussion? Correct. Rather than and look, I’m implicating myself here, too. I mean, I get excited, I can go way too deep. And then I have to discipline myself to pull back. And how do you do that? Fortunately, I’ve had exposure to a lot of your materials, and could have greatly benefited from those about a year ago before I started fundraising.

But, but now that I’ve seen them, there’s a lot of really good materials here. And you’ve honed in on the skill and the discipline set right now you know that one of the traps can be knowledge, but tell us more about how you apply some of these frameworks and other materials in order to arm a salesperson better before they get into the client meeting?

Yeah, we think about it in three ways people process and tools. And I’ll actually start with the end. So one of the things we really like to do with entrepreneurs and portfolio companies is build the toolkit, it may be interesting to you and your listeners, it may seem out of order, what I’m about to say, and maybe it is, but the way we like to do it is let’s build a bunch of tools. And then let’s embed those tools in a process that has tremendous skill and discipline. That’s sort of the first one two punch that we like to do with people, because our notion is that we will watch you apply these tools in a process of anything, any process, there’s a process for how to run a sales meeting, there’s a process for how to run a I want to raise money from NIC meeting from Nick and his firm meeting, there’s a process from start to finish for that meeting. And we like to build the tools first. And then have you or whoever, the early sales team, usually the founder and a couple other people. And you know, look, I was with a group, I was with one of our portfolio companies last week, but they already have 25 salespeople. So that was a good size group. But go through and say, Okay, this tool is used in the following way. And of course, the tools themselves are built on skill and discipline. And then let’s put that in the process. And let’s roleplay that such that you’re entirely comfortable when you walk into Nick’s office, and you’re gonna, you know that the ask at the end is, Hey, Nick, are you interested in putting, you know, seed money into this company? That’s the ask at the end? What is the journey that’s gonna get you there? What are the key skills and disciplines and knowledge, of course, that you are going to bring forth into that meeting? And how are you going to do it? Because the how matters so much as much as the what, Craig? If you start with tools before process, is there a risk that you’re trying to shoehorn a tool in the place where it doesn’t make sense? Yes, absolutely. We’ve made that mistake. The reason I start with tools, and I want to be careful and define tools, you know, a tool is a what our definition of a tool would be, it could be raising money, you go to a venture capital conference. So you go to a conference where there’s gonna be a bunch of investors, and I’ll pick on myself, I’m the entrepreneur, and I go to that, and I know, I know, Nick’s gonna be there. And I know that particular group is going to be there and a whole bunch of you know, 100 people are going to be in that room. A tool, so to speak, is how I actually have a conversation with you. When I walk up to you cold, and you don’t know me, I’ve got credit on my chest, you’ve got Nick on your chest, on your name, badge. And I walk in and we believe a tool and I actually we have names for all these tools. It’s the art of the sales conversation is what I call the tool. And it’s it literally architects are small talk.

What I say to you, when you asked me the most common question known to man, which is Craig, what do you do? I have an answer. The next thing you’re going to ask me is okay, what does that mean? So Craig, you help companies build into in their sales engine? What does that mean? And I say the next thing that I’ve got absolutely memorized, and then I know how to get into and out of that conversation, hopefully in an interest interesting way, that is a set of tools that are the foundation of which is skill and discipline. So that’s a tool. Here’s how we sales engine. Here’s how we Pritzker talk about ourselves at a networking event. That’s one tool. Got it that makes sense can be a value. So Sal doc, yes, conversation framework and responses, I get it. Yes, exactly. Right. And again, going back to my first point about this transition from entrepreneur selling to professional selling, I made this mistake when I started out, I would just walk up to you and just start talking about any if you sort of picture this a circle in your mind, I would just sort of enter that circle from anywhere and try to figure out how to tell you about my value proposition which was still not clear in my

My own head. And guess what you’re standing there doing, you’re going, you know, maybe nice guy, but I have no idea what

happens all the time. Gosh. And that’s a set of tools that we believe. And that’s why we love to get people get these entrepreneurs into the tools, I will absolutely admit that there’s risk to all of this stuff. It may be, you know, it may be risky to create a process

that is not yet clear, because you’re early in product market fit or whatever reason I definitely agree with, with that risk. And what I say to entrepreneurs is, take that risk, I’d rather have you try it, you can always rebuild, I always say to people, your sales process, your how you talk about yourself, it’s none of it’s a tattoo, you’re not tattooing this on your arm, they’re all their words, sales is about the words that you say, in the situation that you’re in, you can always change them, but lock them down for a period of time and try them with discipline, and then see what happens.

Gotta love it. So taking a step back here, you know, we talked about this transition from entrepreneurial selling to professional selling, I’m trying to get a sense for timing, you know, it’s always a function of talent and capital and some other constraints. But when do you think is the right time for, you know, an early stage startup to transition from this gorilla selling stage to more of an organized professional process?

That’s a really tough question. I have an answer. Being careful. I don’t know if it’s right. Your selling answered this question. I’m gonna reposition the question if it’s okay with you, and you tell me if it’s okay, please. How do you how do you know as an entrepreneur when it’s when it’s right to hire your first salesperson? Can I make it that specific? Okay, good as a proxy for building out a sales team. Is that okay? Yeah. So the way I answered this question is because the honest answer is I don’t know, because it depends on a lot of factors. But the way I square it is, you know, you’re ready to hire your first salesperson, when you go to a Starbucks. And you sit down with Nick, who’s got a really good resume. He’s a strong salesperson, he was@salesforce.com. And he was a high performer. So he’s got a good resume. And he sits down in front of you. And you’re and I’m the entrepreneur, and I, you know, we meet each other. And obviously, I, you know, I agreed to interview you for my first sales job and my company. And you sit down at that Starbucks with a cup of coffee, and you say to me, the following, and here’s how you know whether you’re ready to hire that person. Because if Nick is a true high performer, what he’s going to do in that moment, he’s going to ask you a bunch of questions. He’s gonna say, hey, Craig, tell me about sales engine, to who are your targets? And how have you filtered your target set down to the people who you absolutely positively know are your first customers? Tell me five stories of when you’ve succeeded in those sales and tell me another five stories about failures to articulate your value proposition. Help me understand when you’re at a networking event, how to talk about yourself crisply, can you say, Craig, in one sentence, your value proposition? Tell me the seven objections you routinely get in the sales process. And by the way, tell me the five or seven steps of your sales process, and how you know, to move from step to step to step? Tell me the list of 10 or 15 qualifying questions in priority order that you ask at those steps of the sales process. And Nick, I could go on and on, but you see what you see what I’m doing, when when an entrepreneur can answer. Most not all, we can never answer all those questions, but we can answer most of those questions with fidelity, you’re ready. And the reason I say that so strongly is I’ve made this mistake, where I’ve hired insanely talented salespeople, and they failed. And they didn’t fail because they weren’t talented, they failed, because I had no idea what our sales process was, what the tools were and how to apply them.

And so you know, that you’re ready when you can really start to answer those questions, which means you got to be able to answer those questions. The entrepreneur has had to go through those those motions, him or herself, and figured out what are the top seven objections I get? And how do I how do I handle those objections, etc. Interesting, interesting. You know, as we take this to the next level, there’s different types of salespeople that may be right for different stages. I know that you’ve written about a couple different profiles in your books. I’m curious if this example here, if my my previous guests had gotten this from you, but we had a tea Nam on the program, and he was talking about these three different types of sales leaders at different stages of the startup. So he said like at the beginning, the profile of a sales leader is more of a Davy Crockett type character who’s an independent explore kind of finding their way through the wilderness and then the next stage is more of a Braveheart character. It’s someone with a this warrior spirit that help convert these leads and really drive a lot of progress. And then finally,

At the scale stage, it gets more like this Dwight Eisenhower character, someone with political savvy that can align all the sales folks in the right direction. Do you agree? Do you disagree? And what’s your philosophy about the mental makeup or the the sales leader profile at different stages of a startup? Well, that’s not my characterization. But I’ll tell you, I absolutely love it. And I agree with it. I’ve heard angles on that before but not stated that way. I really like it. Let me add a layer to a thing by trying to answer your question, what we look for, and what we try to help with. And you alluded to some work I’m doing now with one of the world’s largest tech companies, and we’ll let them remain nameless. But it’s super exciting project, over 10,000 salespeople, and 1000 sales leaders, and one of the things we’ve been talking a lot about with them, and I’ve been writing about some is how to build a strong sales culture. As you move from the Davy Crockett using his example and your example, the Davy Crockett to the to the Braveheart to the Dwight Eisenhower, as you move, one of the questions we like to add to that is, the obvious question is what are the characteristics of each of those profiles? But then, beyond the layer above that is what kind of sales culture are they creating, within the growing enterprise. And we we’ve got a bunch of notions about this. And none of this will surprise you, given the earlier part of our conversation around discipline. You know, we believe that a strong sales culture as in any in any one of those three personas, that a strong sales culture is where roleplay is harder than real life. And so it’s high discipline and high skill, and of course, high knowledge. The reason I keep saying and knowledge is that knowledge is going to come, it’s in the water, it’s in the air. So we don’t worry that you’re going to be smart enough on the product, because you got a much bigger problem. If you if you hire me, Craig, and I can’t get my head around the product, that’s a different problem. You’re gonna it’s in the water, I’m gonna learn the product. It’s the question is, can I apply that knowledge with skill and discipline? And so we think a lot about cultures and we wonder, Is roleplay harder than real life? How often is nick or I’ll pick on myself? The Craig, the sales manager, giving nick the sale, the high performing salesperson, how often is Craig giving him feedback? And I don’t mean, great job. I mean, feedback. I mean, you know, Nick, here’s one thing I think you really did well, in that sales meeting just now with craft. And here’s one thing I think you should do differently. And often that dude definitely hurts. That hurts because you are a high performer. And it’s like, oh, god, did I actually do that? Right? How these cultural elements and Nick, I’ll tell you,

you know, you can tell them a pretty intense guy, I get really intense about this, because we just don’t see it. We don’t see that. People say they do feedback. But I don’t buy that. And I’m being very black and white. Of course it exists. But at scale. And with entrepreneurial enterprises, we just don’t see where roleplay is hard. And I’ll give you an example of roleplay up being harder than real life.

Going back to IBM, again, there was a legendary roleplay at IBM. And they were sort of evil genius about how they did this. They would tell us at the beginning of our year, long year long sales school, one of the role plays you’re gonna experience somewhere in this year is going to be an irate customer, you’re gonna walk in a room, it’s gonna be full roleplay, full dress, roleplay, Suit Tie. And somebody they’re just gonna start screaming at you.

And we’re going to find out how you deal under pressure. And by the way, they would say, if you don’t pass that call that roleplay you’re in trouble. Like this could affect your job. So think about how what an evil genius that is, right? They put the fear in us right upfront, and then they wouldn’t tell us when it’s gonna happen could happen anywhere in a year could happen in three weeks from today could happen in seven months. Wow. And I will never ever forget walking I will never forget as long as I live. Mine was about seven months in. Every time I flew to Atlanta, Georgia for three weeks of training. I would wonder Is this the time Is this the one and one day full dress blue suit, red tie white shirt, walked into a room and they were so clever how they did this I walked in a tiny room with a guy who was one of our trainers who happened to be an ex Buffalo Bill national football player. Guy was enormous is like five times my size. And he showed he got up so fast the desk went flying across the room and he just started screaming profanity at me. It was completely an act good worked himself into a frenzy scared the you know what out of me. And all I did was stand there basically in shock and apologize. Which, interestingly was what exactly what IBM wanted us to do. They said just defuse the situation you’re going to run across

Things like this, all, you don’t even know what you’re apologizing for, you just apologize, you try to take the air out of the room, you try to take lower the temperature. And so that’s what I did. And I, you know, I pass the call and this guy, great, he gave me a huge hug. He was a teddy bear of a guy, but he was incredibly intimidating when he was fired up. And if you just stop and think about that for a second as an example,

you know, I never went into a difficult situation the same way again. And it doesn’t mean I wasn’t nervous, of course, I was nervous with conflict and difficult clients and stuff like that course, I was nervous. But I knew how to handle it. They decently they, they discipline me, they knew they knew that they would put us in these really difficult roleplay situations where there was some stakes, like, if you don’t do well, you’re in trouble. So it’s those sorts of things. As you move from the Davy Crockett through, that we would encourage that CEOs of entrepreneurial companies and sales leaders of all those personas think about.

So you guys get in you advocate this role playing then is that part of the program and the training that you advocate?

It is Nick, it really is. I mean, it’s central to what we advocate. And it’s interesting, it tells us a lot about an entrepreneur. And it tells us a lot about a company large or small about how they respond to that. And I’ll give you an example from a portfolio company. We went into beginning of last year, we did another thing that strong sales cultures are built on and that’s called a sales sprint. Their top line was suffering, the top of the funnel was suffering, they weren’t adding enough situations. So we did a sprint. And this is something I’ve done in all of my companies where we got together with the portfolio company and the sales team, very small five people. And we said for the next month, we are going to dial for dollars. It’s a b2b enterprise SAS company. And we said we’re gonna dial for dollars all day, every day. It’s a sprint, you’re not gonna like much of it. This is about the metaphor, Nick that I have for this is not very kind. But for a while in college, I rode crew, I was terrible at it, but I rode crew. And there’s this great thing with crew where the Coxon yells out power 10 in a race. And that means you pull that or as hard as you can for 10 strokes as a team. And not to be graphic here. But you often you know, when you actually do that, in a race, you often throw up over the side of the boat, because it’s that intense. That’s a sales sprint. And you just get after it, you know, and that what I’ve learned as a venture partner at Pritzker and with sales engine, is that I’m really conscious, you know, I’m very honest about what this is with a sales team. And you can imagine how this goes over in a conference room with a sales team. And, and I just say, guys, and I’ll help you, I will make calls with you. I never ask anybody to do anything that I won’t do myself. But we are going to hammer it and man, it is the coolest thing. Because they come out of that week, month. One time we did three months, which honestly, it was probably too much because it Damn near killed everybody. But they come out of there after a month. And guess what they’ve got, they got themselves a pipeline. And it’s just beautiful to see. And there’s all kinds of cool stuff you can do in that month, or that week, to reward people to keep the heat on to fire them up to give them support and inspiration. There’s all kinds of cool stuff you can do. But the bottom line is, this is a sprint, we are going to throw up over the side of the boat when we’re done. We just are

just make sure they’re updating their CRM, right. That’s exactly right. That’s part of it. That’s that’s actually part of it. Where we see reports on Friday afternoons, we literally do this that Briscoe we see reports on Friday afternoon, that are a pull from the CRM. And it’s just it’s so fun to watch because it’s like, okay, my God, we made you know, 600 calls this week. And last year, year, we made 200

Wow. I mean, that’s, that’s, that’s a sprint. Yeah, but I’m not. I have to be careful, because I’m not. I’m not accusing people of being lazy. But you know, look, we all get in a rut where it’s like, oh, God, you know, pipelines aren’t growing or trying everything. And the question is, okay, let’s you know, let’s get some support in here. Let’s build some tools. Let’s have a kick ass script, a kick ass voicemail, and let’s leave 600 this week. Let’s just do that. Wow, amazing. I used to work in aerospace. These guys, you know, they would sell, let’s say a subsystem on to a new aerospace platform like new Boeing or Airbus Airbus platform, and the sales would be, you know, as little as a million bucks, but as as much as $50 million sales. Once you get a subsystem on a plane, you know, they’re, they’re building that plane for the next 20 years. Even if it’s not single source, they, the ticket values could be exceptionally high. I mean, the sales guys were amazing people, right? You just love being around them because they’re so darn good, but I love that but at the same time

I mean, getting them to update a CRM was like a homerun teeth.

They’re so good at what they do, they could kind of go rogue to a certain degree. Well, and we, you know, again, we see that even that’s a very high level, sophisticated sale. We see that everywhere, though. And again, I’m back to my foundation. That’s just a discipline. That’s an embedded discipline. So it’s a way to measure the strength of a sales culture. Are they disciplined about just doing the hard sometimes yucky work of slamming stuff into the CRM? So what do you do when you walk into a situation with, you know, an established, let’s say, is an established sales leader, or were an established Key Account person, and they don’t want to change it aligned with the culture, but at the same time, they’re driving a lot of top line for the organization?

Oh, boy, I mean, that’s a fantastic, very tricky question. I’ve been on all sides of that. One of my favorite stories is having a pretty much of a screaming match with a CEO who has a friend who has now become a friend of mine, The Story Ends Well, but you know, saying this guy that you have running your sales team is a high performer, salesperson, he’s not a leader. So you have a decision to make. And again, I’m really careful with folks like that to just say, you know, I’m a consultant, I’m just, you know, I’m here, my role is to speak the truth, you may not like it, and you can absolutely just not take any of my recommendations. But here it is, you know, this is a person who is bringing in top line revenue, we find Nick out in the real world that this that is often because he or she can sell well not as a leader, then the CEO has a tough decision to make them to, in essence, demote them to an individual contributor, by the way, we sometimes find that those people are delighted by that move, because they really, you know, they don’t want to be a leader, they don’t want to deal with all the management leadership stuff that comes with it. Oh, interesting. Sometimes, though, you know, honestly, sometimes the work results in that person gets removed, sometimes that person gets religion. And it’s again, this is one of the many reasons we start with a sales toolkit. We have seen sales leaders that have been sort of lukewarm on this come to life as a result of having this a literal book, to walk into a room with and you know, it’s digital, and all that cool stuff. But it’s literally a book that they walk into a room and say, This is how we sell. This is our motion. These are, you know, this is 120 pages of how we do every single thing that we do, and they start to get fired up, and they get religion about it.

But at the end of the day, the sales leader, him or herself, or that group, like this tech company, there’s 1000 of these people more than 1000. We’ve gone 30 at a time 50 at a time, day by day with them to help them develop the knowledge, skill and discipline of both the sales motion and the sales leadership motion.

Got it? Got it. Yeah. And, you know, I’m sure you’ve encountered this situation before, I know that I have, but how do you handle a situation where the product is broken? Right, you get in there, you’re in there to help with the sales process and the sales culture and creating a sales engine that performs but it becomes clear to you that the product or service, the offering itself, is just lacking. And maybe in your estimation, the issue isn’t with sales, it’s with, you know, the fundamental value proposition.

I don’t have a good answer for this. And it’s probably obvious what I’m about to say we actually have a situation like this right now. And it’s frustrating. And what I’ve said, and it’d be interesting to know whether you think this is good advice or not. But what I’ve said is okay, the product is not there yet, we’re learning from the market, the product is not there yet. And the way we know we’re learning as the sales team is doing their job. They’re really out there attacking the market, and the market has started, you know, shrugging his shoulders and going yeah, okay, that’s not very interesting. So you have a couple of choices. And my advice has been and I did this with my first company had to make this tough pivot. My advice is, wasn’t is teach your salespeople to be incredibly disciplined in these early conversations with customers around managing expectations. And what I mean by that, I’m probably getting too granular in your question, but what I mean by that is, I would say something I meet you for the first time, and I’m selling you what is in essence, a product that I’m worried is broken or just not right. I need to be honest and transparent and incredibly deft or agile maybe as a better word at handling managing expectations in that conversation to say something like, you know, Nick, one of the things we’ve been experiences and pushed back in the market on the product. And here’s what I think’s going on. We’re in a sprint from a product development, assuming that’s true. We’re in a sprint at the product development standpoint to do some of the following things

With the product to make it right, what it means for you is, what I would like to offer is as that transition is taking place, that we have an agreement with you where we can go above and beyond for you

in different ways that are on the top that overlay the product, better service, more responsiveness. And again, I’m making some of these up, Nick, because I don’t know, you know, I’m making up details, but just a way that the sales team because if you’ve got a broken product, it’s not good business to sell that knowingly sell that product. But as you transition, hopefully, you know, you either gonna shut the company down, and you’re gonna say, okay, it didn’t work, or you’re going to transition to a better product. Yep. And what I want people to do is just get on board and say, Okay, I just made a tough conversation, ie the sales conversation even tougher, because now I gotta have a sales conversation about a product that’s not really ready. But I can do that. I can do that I can say to Nick, let’s look holistically at the product and the service that surrounds it. Here’s what I can toggle, Nick, I can increase service. I will be more responsive, my team will be more responsive. Wow, the product crosses this bridge.

I just I think that’s I don’t know a better answer. I’m sure there is one. I don’t know a better answer to that situation. Well, there’s definitely a to your point, there’s different ways to compete in different value propositions for different types of customers, right? It might not always be best in class software, it could be more highly attentive service, more guarantees along a different paradigm, every customer is different and their needs may differ. I know that personally, if I can, if I can get in touch with my financial advisor. That’s something really important to me, if I use Wealthfront, or betterment, and there’s nobody to call had that, that makes me a little uncomfortable, even though I know that the robo systems are are really valuable. There are different ways to compete. product performance is not the only differentiator. Well, I love it. I think you’re absolutely right. And just because I’m such a nerd about sales, language and tools, what you just articulated is what I would label as a series of qualifying questions, which is a skill. It’s a skill to suss out early in a relationship, what’s important to this guy neck, right? What’s truly important, because if look, if he comes back and says, Look, I just want everything fully automated, Greg, I want the product to work first time, every time we’re done, you’re qualified out, I’m done because that my product is not working. So it’s not going to happen. Like if I get down to the bottom of that, and you’re a product guy, and then we got nothing to talk about. And I have to be super honest. And just say, Nick, you know what, to tell you the truth. On our product roadmap, we’re just not there yet. And I’m just telling you, may I call you when we’re there, May I stay in touch with you? I’ll drop you a line every month. But we’re not there yet. And the best thing I can do for you is recommend a different product right now. We think that’s what great high performing salespeople do, they pivot to the next best option, that’s not your own. But you what you’re pointing out is the nuance skill of saying, Hi, let’s get to the bottom of this guy, let’s see what he’s really interested in. And whether we might have a deal that’s a little less product and a little more service. Love it. Love it. Yeah, one stop. One of the sort of fun situations I found myself in. So most recently, before I started investing full time, I was a product manager and spent a few years, you know, taking a concept from a piece of paper to mark it. In the process of that not only did I I have to work with customers intimately. But I had to work with our engineering team, our science team, and of course, the sales team. And one of the funny and healthy tension points with sales, is when the sales folks are over selling, or selling things that don’t quite exist, either yet or at all.

A part of me loves it. I love the guy, that or gal that goes out and knows what needs to be built and can sell it and come back and say we need this. But that can also, you know, create a lot of tension for the organization. So have you come across situations like this? And what’s your advice?

So I’m smiling because yeah, I mean, of course I’ve been in situations like that where it’s a little bit of vapor that you’re you’re selling. I’m going to come back and I hope this is where you want to go. But I’m going to come back with this notion that I believe that if you’re magnetic as a person, and you’re incredibly disciplined and incredibly skilled and incredibly knowledgeable and that shows up in a room you know, I always use this phrase show up, stand out and break through in every room you’re in. Then I think you have earned the right to to say to somebody I’m a little bit back to your last question.

But to say to look someone in the eye and say, what I’m selling you is not fully realized yet. Here’s why this makes sense for us. You know, I’ve truly listened to you. And I understand I believe I understand your needs. And here’s why I still think even though this thing is still being built, that we belong together, we belong doing business together. I think it’s just an incredibly high integrity thing to say, I’m in a lot because I teach sales at a, you know, at an elite business school. There’s a lot of a lot of pushback and some really interesting mindsets in that room as we begin every quarter because they’re like, going through their mind and having done this for 10 years, we’re going through the mind is okay, salespeople are trained to be manipulators. And so I’m with questions like this, I like to bring it back to you know, are there are manipulators in the world? Of course there are are they all salespeople? God? No, there’s manipulators everywhere. But when we’re selling, what selling really is, is really good at you know, really the ability to ask great questions, really hear the responses, really manage expectations, and draw people towards you like a magnet such that you build that trust, and you can say, Okay, I’m gonna just speak very plainly this product is not there yet. Let’s, let’s still do this. Here’s why it makes sense. And you can actually win those situations. Because then you I mean, God, all kinds of good things happen. As you know, all kinds of good things happen. From there, people fall in love. You know, I literally teach a section in classic Kellogg called Let’s fall in love. And it’s about how to do that stuff such that people they don’t like you, they love you. Like, I’m going to stick with this gal or guy, because they just tell it to me straight.

Sign me up, Greg. So fun to watch. I bet. I bet. You’ve got a reputation and have developed a lot of quality material around storytelling. To a certain degree life is in sales, of course, is a series of stories. It’s a series of narratives, it’s connecting with people in a way that that makes sense and can compel them to make a decision. Can you talk to us about, you know, where you see, maybe founders or people that are leading sales within early stage tech companies? Where do you see these folks going wrong? And what advice would you have with regards to storytelling?

Two answers, two perspectives, Nick, my experience of entrepreneurs and sales leaders is that most of the time, they’re really good storytellers. But if so that’s one perspective. They’re good storytellers. They, you know, the, the entrepreneur usually can tell what we call the origin story, the business, you know, why did you start new stack? If I said that to you? I bet you’d have a really good story. And look, can we all improve our storytelling me included, of course, especially when we’re learning new stories, I mean, I always say to my students, guys, I’m a story connoisseur the first time I tell a new story. It’s terrible, like all over the place. So and we all laugh about that it takes practice to do these things. But my other perspective is a little more controversial. What I don’t think we do is collect stories, we need to become collectors. And it’s a three step process, we need to capture the stories that we see all around us, distill them, that’s make them tight. Sales is about the word, just say, Make it super tight, and then tell them and tell them in a compelling way that connects to people’s emotions. So I sort of get to that to try to unpack that perspective a little bit. I always say to salespeople, sales leaders, entrepreneurs, I always say to them,

are you as conscious? When you walk into a situation? You’re raising money from new stack? And Nick, you’re selling craft, whatever that situation is? Are you as conscious of the emotion that you’re going to leave in the room as you are the data that you’re going to share with that customer? Or person? And you know the answer, I mean, people I got way more, you know, I’ve got my charts, I got my stuff. And again, nothing wrong with that nothing wrong with knowledge.

But if we know and we do know, this is knowledge, we know that people are influenced we as human beings are influenced by our emotions. Danny Kahneman wrote, Thinking Fast and Slow, the entire is five decades of research. And the Nobel Prize show that we’re influenced by emotions, we ought to have the asset that connects to people’s emotions, and I call those assets stories. The metaphor here that I don’t think we’re good at is what I always say is I want you walking around with a quiver of arrows on your back. Each arrow is a story there should be 30 to 50 of them, that you can literally pull out in a nanosecond because you’re that practiced with them. And I find my perspective number one,

people generally good story

tellers. They just don’t have enough stories. You need real say, Craig, tell me a story about your value proposition. And I just pull that arrow straight out and just bow it up and let it fly. No problem.

Greg, tell me about a time that you failed. I got dozens of stories like that.

Stuff like that. And we’ve got to be able to do that. I’m on a mission. And I wrote that book, Nick for a reason. I’m on a mission, to have people, my Kellogg students, our clients, our portfolio, collect, and distill, I call it a story makers collect and distill that quiver of arrows so they can tell them in a compelling way.

Greg, can you tell us about the story canvas and how you suggest that folks use it? Sure. The story Canvas is a tool that Carter cast, and David Schoenthal. And I worked on a couple of years ago for what we call a story bootcamp at Pritzker, where we get our portfolio CEOs and leaders executive teams in the room and we walk them through what we just you and I just talked about, and those two guys are amazing. And colleagues of mine at Kellogg, colleagues of mine have Pritzker and we got in a room as we were preparing for the story boot camps and said, how might we

create a tool that will help this process of captured distill Intel? So what the story Canvas is, Nick is simply it is the architecture of a story, left to right, or west to east. So you know, every story has a narrative arc from left to right. It starts with you know, I tell you a story that starts with context. You know, Nick, I was walking down the street and I got on the bus. That’s context, right? The next as the arc begins to climb, the next C is conflict, something happens and conflict doesn’t necessarily mean bad. Just something happens. So context, conflict, climax, closure, the four C’s left to right, that’s the narrative arc of the story. What the story Canvas does is have you lay the story out, as you build that origin story of new stack, or the origin story of sales engine or a failure story around craft, whatever it is, you get those four elements, that’s the left, that’s the west to east, then you turn it over that story, Canvas, and what it encourages you to do is stretch that story north to south. And what that means is north to south is the emotional arc of the story. Interesting now, okay, now, Nick, add emotion to that story. What happened? How did you feel? What did Kraft say that shook up the room. And we try to embed those elements. So there’s north to south motion in that story as well. That’s what the story Canvas is trying to do.

Love it, love it. And you also talk about, you know, during the process of capturing, distilling and telling these stories that you got to figure out the right time, and the Right Reasons to tell different stories. Do you have some thoughts or some wisdom on that for the audience? Wisdom? I’m not sure I’ve got a thought. It’s. So this notion of the tool that I outlined in my book called The Story matrix. I mean, it’s, you know, it sounds kind of fancy. It’s not it’s just a grid. It’s a Excel spreadsheet of rows and columns. And so the way I try to tackle this challenge is, the columns are the types of stories that you and I should always be able to tell as leaders, entrepreneurs, investors, salespeople, whatever, we should be able to tell success stories, failure stories, fun stories and legends. Legends are teaching stories. You tell me a story about Steve Jobs, I tell you a story about Anita Roddick of the body shop, whatever, right? They’re legends, because they are legends.

Those are the columns across the top of the matrix, then the rows is more difficult. So the question you’re asking is actually more difficult it is, the rows represent

where you need stories, the use cases, the situations, the occasion. So let me give you an obvious example you might have, I might have a row of stories successfully upon legend, a row of stories about raising money

and going out to raise money. I know you’re gonna ask me a bunch of questions about my business, my business model, my value, prop product, market, fit, target market, all that stuff. I should be able to answer those questions with facts and stories. So I’m going to collect a row called raising money. The roll is called raising money. And I’m going to collect a whole bunch of stories in that row, some successes, some failures, maybe a fun one, maybe a legend of you know, I’m trying to think of somebody you know, a legendary person who went on Shark Tank and raised a bunch, you know, a legend about going on Shark Tank and raising a million dollars from Mark Cuban something like that. Yep.

So the role is the hard part of this, as I’ve been working on this for a dozen years now is helping people articulate their occasions. We literally were talking about this last week in class at Kellogg, you know, Kellogg, our students, and so they’re thinking about use cases like getting a promotion, getting assigned to the next big project, and they need stories, so they can sell themselves into those situations.


You can’t just go up and say, Hey, Nick, I’ve got the best resume, you should put me in that project. That’s not going to work. either. They’re interviewing for what post MBA high level positions, right? And interviewing would be a whole row or even a set of rows. If you unpack it. Yep. Yeah, the great question and tough to get at it takes you know, again, all this stuff takes practice and discipline to get get good at that. But man, it’s so fun when you start seeing that story matrix become populated with stories. And I say to my students, by the time you graduated from Kellogg, I want 50 stories on your story matrix, you’ll decide I can’t make you do that you’ll decide whether you take this seriously or not. But stories are raw power and influence. Why because they touch the emotions and love the framework. You know, I probably have 3030 stories that I pull out on a somewhat frequent basis, but I’ve never organized them and thought about them in such a strategic way. And I’m sure, you know, to add your your discipline and skill elements that would make me a much more effective teller of the stories if I if I were to do that.

Well, you just have at your fingertips, I mean, that’s why the quiver of arrows metaphor works. So well, you just reach back and grab it. Yeah. Like, oh, you know, you wanna hear a story about my first business? Sure. And you can reach out and grab a dozen if you want. No, not. And I always careful to say, like, you don’t, you don’t tell a dozen stories in an interview for an hour, you know, that would be overkill, but you tell two or three, but they better be good.

Better be good. So, to that end, you know, you also have this approach in this tool called the perfect sales meeting. You know, it’s it’s one of the popular things that I know you teach at Kellogg, I’ve heard a number of folks talk about it in a very positive way. Can you tell us how one should think plan and increase their their sales, meeting effectiveness and utilize this perfect sales meeting technique?

You bet. Again, I’ll use this framework that you and I have been playing with this in this chat that we’re having, which is so fun, knowledge, skill, and discipline. So I’m going to take knowledge and move it aside, because it depends on the meeting, but you’re clearly going to have your act together, you’re going to know why you’re there. And so the knowledge, I’m just I’m gonna leave that aside, because it’s hard to talk about that with any specificity. But there’s one skill and seven disciplines that I would love for people to take away from this conversation. I’m gonna go through them very quickly, I’m gonna do the disciplines first. Remember, at the beginning of this conversation, Nick, I said something about, you know, you should have a sales process for raising money or a sales process for how you actually run a meeting to the point where you could actually brand your meeting. Yep, we’re doing this at the major tech company that I’ve been alluding to, where we are going to create a branded way that they do a meeting. Well, what does that mean? What it means is, you know, a brand has edges, a brand makes promises a brand does things and does not consciously do things. So what I like to do with people is, and I love this question you’ve asked, because I want to cause people to think about and break down just the disciplines of running a hot what I call a high impact meeting. So the first discipline is in the preparation, and I realized there’s lots of prep that you have to do for a meeting, and I’m ignoring most of it. But I’m suggesting that one of the last things of prep that you do is articulate your three clear points for yourself. What are the three clear points of this meeting? It’s, you know, it’s on top of what does success look like for the meeting, what’s the agenda, all that sort of stuff, that’s all important. What I want you to do is be able to sell yourself at any moment in time, which which necessitates having the three clear points such that I show up your office and you know, this is true, because you live in reality in real life. I show up at your office and you say, God, Craig, you know what, we had an hour, we’ve only got five minutes, or Craig, you know what, we had an hour, I’m so sorry to do this to you. I got called into another meeting. Can you walk me to my next meeting? And you know what? I’m ready? I say, Sure. Nick, let’s talk about three things, the three clear clear points in this meeting that we were going to have was this, this and this, at least I get my point across. So the discipline and if you have the full 60 minute meeting, then at least I’m concise and clear and articulate about my three clear points. That’s one.

Second one, I always ask people, and I’m a little snarky about this, I always say what do you bring to a meeting? And people usually say, Well, you know, an agenda. And I say that’s great a written agenda is let’s agree that that’s a best practice. I realized that our meetings were that would be weird, but let’s just go with it, let’s say a best practices and agenda. That’s actually not the discipline, that is a discipline. It’s not the one I’m talking about. What I’m talking about is the verbal discipline of starting a meeting properly. And I call this the purpose benefit check. The purpose, the purpose benefit check is something that you say verbally towards the beginning of the meeting, I walk into your office, we make a little bit of small talk, and then we start the meeting and I say, Nick, the purpose of this next hour is to become as efficient and effective and effective as possible at running high impact meetings. What I hope we gained from this time together is that you pick up seven disciplines in one skill of running high impact matrix. How does that sound?

That’s a purpose benefit check that I just did you, right. And it’s an insanely simple verbal discipline. But what it does is it adds credibility. It’s the verbal exposition of your agenda, such that I gain credibility in your eyes for knowing what this meeting is about. And again, contracting by you being able to say, you know, no, Craig, I want to talk about something else, or Yeah, Greg, we’re right on, let’s go.

And finally, and most importantly, it puts me in control. I always say a meeting is a show, run your show, your show, run your show. And it begins with a purpose benefit check. Let’s get this thing going the right way, the first time.

The next one is endorsements. Let’s now say this happens to entrepreneurs, Nick, all the time. And we think on many pitches you’ve seen, where there’s the entrepreneur, the co founder, and the head of tech are the co founder and the marketing person or whoever you’re seeing.

There’s, it’s now a team situation, if you’re in with a team, I always talk about sort of the next thing in time that often happens in a meeting is an introduction, Craig introduces Nick, and I’m whoever you’re the CEO, and I’m, I’m the guy who had the connection to new stack, and we walk in and I’m introducing you as the CEO of this company. And I can introduce you, I can say, hey, you know, Carter, this is Nick. He’s our CEO, and he came from Food Science at Kraft and we’re, you know, excited to be here. Nothing wrong with that. That’s an introduction. In my way of thinking about skill and discipline, an introduction should be an endorsement.

I can say the exact same thing with a little emotion. Hey, Carter, this is Nick Nix, the CEO of our company. He came from Food Science at Kraft and we’re really, really excited to be here. You know, it’s interesting, as Nick has worked with our clients, Carter, there are two words that clients routinely use to describe this guy. Amazing. And fun.

Nick, over to you. That’s an endorsement. I just endorsed you, you must have heard a lot about me, Greg.

I have in real life. So but you know, it’s we endorse each other. And you know, of course, it’s got to be authentic. And all these things. People push back on this like, well, what if you don’t believe that it’s like, well, then you don’t say it if you don’t believe it, right. But you find something, you find something interesting about me that you can endorse me on and I find something interesting about you, it just adds a little color and context and emotion to the meeting. So endorsements

for pivot, we’ve all been in hundreds, literally of meetings where somebody’s run away with our meeting. And it could be good energy, it could be bad energy. Doesn’t matter what kind of energy it is. But somebody else Craig gets energy, he just runs away with a meeting. You have to bring me back. And it’s a pivot. And it’s the simplest discipline. When we do ride alongs, Nick, with sales teams and sales engines, we see this we see bad behavior, people just let people ramble when they should say, you know, Nick should say to Craig, hey, Craig, this is a great point you’re making, you know, it reminds me that a couple other things we want to talk about is x and y. Let’s go there now. And you just go. Or you say, Craig, you know, I’m glad you’ve got energy about this 20 minutes ago, and we started this meeting, you know, we talked about our purpose being talking about x and y, we talked about x, let’s move to y and you just move it’s almost a physical pivot, you just move. That’s how you run your show and stay in control of your show. So that’s the pivot.

Number five, closing a meeting.

We see the most weak, one of the most weak parts of a sales engine is the closing of a meeting.

And we always say closing should have five steps. Number one summarize, Nick. We it was this was a great conversation. We talked about X, Y and Z. Now let me ask you a second second step of closing the check. Let me ask you, Nick, did this meeting deliver what we set out to deliver? Yes, no, maybe that’s the check. Great. So accountabilities, action items, and accountabilities. I’ve got three things that I owe you. I owe you an introduction to Carter. I owe you that white paper that we wrote on food science, and I owe you whatever.

Do I have that correct? Yes, no. Great. I’ll get that to you tomorrow morning. fourth element of closing, scheduled the next meeting, if appropriate. Yep. Sales, raising Monday lose momentum scheduled the next meeting. And finally, the most common one that people do do well is thank you, but they often only do thank you. And so closing is five elements quickly to the end here. Following your shot is the sixth discipline. Or sorry, let me jump to let me jump to the sixth that’s one that’s the seventh the sixth one is and early. If you have 60 minutes and then start closing and 50 If you have 2030 minute call or meeting start closing and 25 Interesting. Why? Why because it it shows that you are in complete command of the meaning and the content and it’s your show. You give people five to 10 minutes or four to

Eight minutes of their time back their day, people appreciate that an insane amount.

And if you can’t say it in 60, you probably can’t say it and 50. So just and early, it’s a discipline. And then finally follow your shot. And that what I mean by that the example is write a thank you note, a handwritten thank you. No, I’m huge on this. Wow. And I just think it differentiates you. And what really differentiates you is those seven disciplines put together and run with consistency.

People respond to it. They say this guy, Nick, I don’t know what it is about him because they don’t know the purpose benefit. Check it. I don’t know what it is about this guy. But we always get it done. When he’s in the room, we just get it done.

And then finally, just a mention of the skill. And we’ve talked about it already. The skill of asking better questions, I call them impact questions. They go deeper and broader than other forms of question. The reason I characterize it, Nick, as a skill is it takes a lot of practice to ask the right impact question at the right moment. We’ve got to have better questions. Most people ask the same questions over and over again. We need to ask better questions.

Couldn’t agree more in IE, you know, to a large degree, I feel like the sales process, a huge component of it is selling yourself. You know, it’s not just the product or service. But the more confidence that the prospective customer has in you and your ability, the more likely it is that they’re going to have confidence in, you know, what you represent, from a product standpoint, I love it. I’ve been one of my MBA classes is called selling yourself and your ideas. And it’s for that reason that you just said, we are selling ourselves, if you’re magnetic, I’m going to do business with you. I just am

I’m going to trust you that you’ll get that product, right? Or I’m going to trust you that you’re gonna be there for me if you’re magnetic. If you get it done in every meeting, you’re gonna get it done for the business. You just will. Yep. Yep.

There are libraries of books about unproductive meetings. It’s just sick. And it’s not this is not rocket science, it does not take you a Nobel Prize, to be able to run a great meeting, right? You just have to do with discipline and some skill.

One question that seems to come up a lot with with my founders and and I’ve noticed it myself, during the sales processes, you know, sometimes between meetings, you know, you can hit this rut, with prospects. You talked about before, how you should set up the next meeting, you know, before the end of the original meeting, which I love. But, you know, sometimes the prospect just wants time to make a decision and momentum slows, you know, how do you advise folks on creating urgency and continuing positive momentum? When you’ve got kind of a lead? That’s that may be stagnant?

Yep. There’s a tool for this, that I say that a little bit tongue in cheek, but there is I mean, one of the tools that we always build in a sales toolkit is something that looks like the following. And again, I have a loose definition of tools, right? Because it’s actually a way of it’s a discipline, disciplined way of managing expectations.

We will talk about what you and I just talked about the disciplines and skill of running a high impact meeting, and then we’ll say, Okay, now there’s a very specialized type of meeting. It’s the first one, the first one you have is where a lot of things are happening at once. People are asking, Can I trust this person? Is he competent? Or is she competent? Can I trust her? And one of the things that you that we as professionals need to do in that first meeting, is anticipate what the question is anticipate the reality of the question that is asked, which is I have, so I’m just going to use the examples I get in front of the deck. Next, the decision maker. And we’re in our first meeting, we’re just getting to know each other. And I’m sitting there, if I’m a true high performing salesperson or entrepreneur thinking, Okay, this guy’s a good guy. But this thing could bog down for any number of 1000 reasons. So what am I going to do when it bogs down? Well, what we like to do there is we like to insert a discipline in that first meeting that goes something like this, and I’m not doing this in the first minute, I’m probably not doing it 20 minute, but in the 45 Minute, I might say something to you like this, you know, Hey, Nick, at sales engine or at new stack, we follow up a very organized and disciplined sales process. One of the parts of our philosophy of sales is that as we’re getting to know you, we want to be careful to hear from a bunch of those around you and really get the full understanding of the business such that we have a better sense of it, and we can we can be a better partner to you. And what that means functionally is I’m going to want to talk to folks around you, number one, and number two, Nick, I would love to understand how best to communicate you. If we begin developing relationship I’m saying I’m not saying

When I’m saying.

And if you do a full stop there, there’s sort of two expert moves, that we always talk about expert moves, there’s two expert moves there. One is I’m putting a caution flag in front of both of us as we get to know each other that I’m not going to get stuck at you. If you if you bogged down, I’m, I’m on record saying, I’m going to go to people around you. And I’m going to talk to them, because that’s part of my sales. It’s part of my very sales process. And the second thing I’m doing the second expert move is to say, is to ask you, how would you like me to communicate to you?

You know, may I? May I follow up with you, you know, on a bi weekly basis, Nick, just to update you one on what I’m working on and to, to request information from you as we go along. It’s very rare that somebody says no, Craig, you can’t do that. And if they say yes, which they very likely will, it is much harder for that person to go dark on you. Much, much harder, interesting. And if they do go dark on you, you’ve got an escape hatch, you got other people. And look, obviously, none of this is perfect. But if you can set that expectation in motion in the first meeting, or maybe the second,

you build some bridges to you get you get your deal, you can get your deals unstuck.

Love it. Love it. I’m going to use it.

Yeah, I mean, that’s a great question. And it’s a nuanced question. It really is. That’s these are the, you know, this, you’re putting your thumb on some of the 1000s of really deep nuances of high performance selling. Sure. I don’t mean to get in the weeds by any means. But I know that everyone has suffered with that situation, right? Whether it be in the meeting, dropping the ball or being ineffective, or in between meetings, and not appropriately managing your funnel, letting leads go cold, or maybe it’s just a natural byproduct of the sales process that you know, some of these, some of these situations can slow and it’s hard to reignite them. So to speak. Exactly, right. Yep. And you always are trying to find a way to do just that without being cheesy or overbearing, or you know, sending you an email every day. That’s yucky on on any day. Yep. Great. What’s the best way for listeners to connect with you? Well, we are the best way to connect with us is on LinkedIn or on Insta, you know, we’re pretty active on both platforms. So that’s always a good way to connect. And then of course, I’m, you know, I’m at Kellogg, people can find me at Kellogg via the faculty pages, or just Craig at sales. engine.com That’s the probably the easiest way to get a hold of me.

The man is Craig Wartman. The book is what’s your story using stories to ignite performance and be more successful? Craig, thanks so much for the time today. This was a really enlightening interview and, and imagine it’s gonna make me a much better salesperson. Oh, it’s such a pleasure. And I’m honored. So thank you for having me. All right. Thanks, sir. Appreciate it.

That we’ll wrap up today’s episode. Thanks for joining us here on the show. And if you’d like to get involved further, you can join our investment group for free on AngelList. Head over to angel.co and search for new stack ventures. There you can back the syndicate to see our deal flow. See how we choose startups to invest in and read our thesis on investment in each startup we choose. As always show notes and links for the interview are at full ratchet.net And until next time, remember to over prepare, choose carefully and invest confidently thanks for joining us