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How to Accelerate Your Sales Through Stories, with Craig Wortmann [Episode 362]

Joining me on this episode is Craig Wortmann, CEO and Founder of Sales Engine, Inc., a clinical professor of entrepreneurship at University of Chicago Booth School of Business, and author of the book, What’s Your Story? Using Stories to Ignite Performance and Be More Successful. Among the many topics that Craig and I discuss are why need to create a Sales Trailer, a sales version of a movie trailer, to very quickly capture buyers’ attention, how to create a story matrix; why stories of failure can be so persuasive and how to set your buyers’ expectations.

Key Takeaways

  • Craig worked in a Congressional office in D.C., and joined IBM about 25 years ago, selling the AS/400 in Chicago. Craig credits IBM with great training that prepared him to teach entrepreneurial selling to MBA students.
  • Craig teaches entrepreneurs how to survive, and then thrive, ‘in the wonderful chaos between time-zero and break-even.’
  • Customers will not beat a path to your door; sales is not a subset of marketing; and, the time to hire a salesperson is after you have a sales model.
  • Buyers will not work to understand your message. You have to work to be understood.
  • Create a Sales Trailer. It’s like a movie trailer for sales. You don’t have four paragraphs to tell a prospect about your brand. You have eight seconds to capture their attention.
  • Expectations start to get set in the qualifying phase. When does the qualifying phase begin, and how long do you take to qualify your prospect?
  • The best salespeople can recognize when there’s not a fit, will say so, and will offer to connect the prospect with other resources that may serve their present needs.
  • Entrepreneurial selling includes the step of resetting expectations, which is done in a short conversation after the close, preparing the client for customer success.
  • What’s Your Story? introduces the story matrix, a tool you can use to to develop important messaging themes.
  • Why do stories of failure affect in a positive way?
  • Impact questions uncover better information. They dig deeper, cut broader, and have harder answers. Ask something about the business, the client should know, but doesn’t. Don’t ask impact questions before a conversation is on solid ground.

More About Craig Wortmann

What’s your most powerful sales attribute?

Simplicity. Being able to give people crisp answers.

Who is your sales role model?

Keith Harrell at IBM. He had a profound influence on me.

What’s one book that every salesperson should read?

Give and Take: Why Helping Others Drives Our Success,

by Adam Grant.

What music is on your playlist right now?

From the soundtrack of Money Monster, “What Makes The World Go Round? (MONEY!)”, by Dan The Automator, featuring Del The Funky Homosapien.

Episode Transcript

Andy Paul (0:35)

It’s time to Accelerate. I’m your host, Andy Paul. Join me as I host conversations with the leading experts in sales, marketing sales, automation, sales process, leadership, management, training, coaching, any resource that I believe will help you accelerate the growth of your sales, your business and most importantly, you.

(2:23) Hello and welcome to Accelerate. I am excited to talk with my guest today. Joining me is Craig Wortmann. Craig is CEO and founder of Sales Engine Inc, is also a Clinical Professor of Entrepreneurship at University Chicago Business School, and the author of a book called What’s Your Story? Using stories to ignite performance and be more successful. Craig, welcome to Accelerate.


Craig Wortmann (2:44)

Andy, thanks for having me. I’m delighted to be here. I really appreciate the time.


Andy Paul (2:51)

So, I’m so curious. A clinical professor makes is sound like medical. Are you’re a psychiatrist or something? So, how’s the clinical play into entrepreneurship?


Craig Wortmann (3:01)

Or my students just think I’m clinically insane. It could be any of any of the above. It is it’s actually a designation that is meant to cause you to think of one or two things, which is, at University of Chicago and the Business School in particular, we have two types of faculty. One is a tenure track research professor, and one is a clinical. And in our parlance, clinical simply means a practitioner. I’m super lucky as a person, I have the best of both worlds. I’m a practitioner, I get to do the do during the day, and then I teach the do at night. Simply, that’s what clinical means. A weird word, but for a very simple concept.


Andy Paul (3:39)

So, how’d you get your start in sales? Maybe give introduction of yourself and how’d you get into academia?


Craig Wortmann (3:47)

Yeah. Again, there’s some timing and some luck that plays. About 25 years ago, it’s receding into the past, of course; as I get older, but about 25 years ago, I got hired by IBM. I was a political guy, I was in a congressional office in Washington DC, and they luckily plucked me out of DC and put me into 13 fantastic zip codes on the south side of Chicago selling the “A” is for 100, some of your listeners will be familiar with it.


Andy Paul (4:16)

I remember the “A” is for 100 but seems like a tough market.


Craig Wortmann (4:20)

Well, when I say that to my MBA students, they kind of look at me like “what?” And so, it gives you– you have to be a certain age to remember the “A” is for 100, but it is still around. I sold a bunch of those on the Southside of Chicago and I had a blast. As I look back on that tenure, I was terrified, I was excited. All those things wrapped into one nervous twitching bundle. But I learned a hell of a lot. What I always say to people is, I am forever thankful for what IBM gave me. They took a scared kid from politics and they put me on the Southside of Chicago and said, “kid walk the streets until you figure out what you’re doing.” And they didn’t cut me loose, they gave me a ton of help, a ton of training, a ton of mentoring. And that’s how I got my start. And I was terrified, I didn’t know business, and I certainly didn’t know selling. And IBM helped me discover both of those things. It’s just really fun to look back on. And I fell in love with it. So, I fell in love with this notion of selling and solving people’s problems, and helping a company perform better and get up that learning curve and that performance curve. So, what I didn’t know then, is was sort of planting the seeds to academia. And I have to be really careful with you and your community. Because when I say academia, I don’t really consider myself an academic. I’m a salesperson, I’m an entrepreneur. Yes, I get lucky and I get to stand in front of the world’s most talented Business School students and talk about this. But what I’ve discovered is, at IBM seeds were really planted. Because I’m now eight years in at Chicago Booths teaching my crazy MBA class, I continually, quarter by quarter get to explore what actually persuasion is, what does it look like? What is influence? And how does that all roll up into sales? That was a long-winded answer. But it’s been a circuitous sort of interesting journey that’s led me to teaching this.


Andy Paul (6:28)

Well. So, one of the courses I teach is called Entrepreneurial Selling. Right. So that’s interesting, because obviously in Business School, a lot of focuses on startups, entrepreneurial-ism. But sales is oftentimes pretty foreign to that student body.


Craig Wortmann (6:47)

It is, and I will tell you, it’s even more foreign at the elite MBA level. And I hope this doesn’t come across as swagger. But you know, Chicago Booths been very fortunate, and we are often ranked either number one or top three in the world. So, at an elite institution, there is a–


Andy Paul (7:06)

They look down their nose at sales


Craig Wortmann (7:07)

They can. Thank you. I was trying to figure out a nice way to say that, but you said it for me. It’s interesting. Harvard Business School just launched a course on entrepreneurial selling. We’ve got Kellogg’s working on it, some fantastic business schools like McCombs and Foster. McCombs in Texas and Foster in Seattle, Washington are working on that, so the message is getting out. And it’s so fun to watch that happen and I get to help from the sidelines. A bunch of these schools, all the ones I’ve included, to try to launch these classes. But there’s some traditionalists and business schools who sort of look at this and go “wait, why are we teaching these people sales?” And I think people like you and people like me and your community, look at that and go “wait, what? Really?” We’re trading on the assumption that revenue is actually important to businesses. When you say like that, people go, “you know, that is true.” Let’s figure out a way that we can really teach this stuff and help our entrepreneurs, first survive and then thrive in the wonderful chaos, from time zero to break even. I’ve been there are three times over, I bet in that wonderful chaos I have failed, and I’ve succeeded. And I’ve felt the burn of that wonderful chaos, and we’ve designed a course that really tries to help entrepreneurs just kick some butt through that process.


Andy Paul (8:30)

All right, nice political reference, “feel the burn there.” We are recording this in the midst of the presidential election season. By the time people hear this we’ll know what the results of the election are. But you focus really on selling for a small business and for a startup. I worked for eight different startup companies in my career, before starting my own companies, nine if you count my own. Yeah, it’s an it’s a pretty distinct skill, especially if you’re selling something that’s relatively complex. So, how do you work with them to gain the behaviors and the skills they need to be successful selling the products of the startup companies?


Craig Wortmann (9:15)

Well, first we dispel some really seductive and pervasive and very dangerous myths. And you and your community will know immediately the first one which is– well, Ralph Waldo Emerson, his famous quote, “build a better mousetrap and they’ll be the path to your door.” And I sort of provocatively and somewhat meanly say that to my students on the first night of my MBA class, and I say, “no, they won’t. They just won’t. Lightning does strike, but I sure as hell wouldn’t count on it.” And if you are counting on lightning striking you probably wouldn’t be at business school in the first place, because you’re just super lucky. What we try to do is to say, “there’s a couple myths that are seductive and pervasive and dangerous. That being one of them.” A great product is a great product. And that’s wonderful. And you deserve tons of credit for it, but it will not, and cannot, and does not sell itself. The second one is, sales is a subset of marketing. If I just sit behind my cool new fancy laptop, and I found out a bunch of social media stuff, I’ll get a bunch of business. Again, does happen, can happen. I’ve been on boards of companies where it has happened. But it’s in dribs and drabs. And in the very early stages of starting a business, you know as well as I do, that is a myth that is pervasive because it’s easier. It’s easier for me to hide behind my laptop and not have to walk into a room and literally shake your hand and look you in the eye and say “hi, Andy. I’m Craig, I’d like to talk today about my business.” It’s scary. It’s uncomfortable. It’s awkward.


Andy Paul (10:51)

Yes, it is the refuge for many entrepreneurs, and I think one of the real reasons for failure is that marketing is easy, sales is hard.


Craig Wortmann (10:58)

That’s exactly right. So, I’m going to get to your question. One last myth that I love to share with you and your folks is, I got this cool thing, I got this growing company, I’m just going to hire some of those fancy, professional salespeople and they’ll sell it for me. And you know what? I’m careful with this one, because I hope you will. I hope you do, but you just can’t do it too early. And I tell you, I made an embarrassing mistake in my first software company. And it’s embarrassing, particularly because I am a salesperson, I went out and hired salespeople too early. And the reason that doesn’t work, and the reason it’s a myth, is they don’t know what to do. I took the highest performing salesperson I can find, this young woman based in New Orleans. I said, “here’s the territory. We love this product; you’re going to be successful”, and she went out and failed. And she didn’t fail because it was her fault. It was entirely my fault. We had not figured out the sales model. It’s not the business model, but the sales model.


Andy Paul (12:01)

I worked with CEOs and to your exact point I say, “look, before you hire a sales rep, you need to go out and sell it. You personally need to sell it. Because if you don’t know what they’re selling, you can’t tell anybody else how to sell it.”


Craig Wortmann (12:17)

Precisely. That is exactly what I say to my students, my executives, my MBA students. What’s so funny about that is, if you just stop with what you just said, “you got to be the first salesperson, you got to go out and talk to people.” What does that mean? It means literally go out and talk to people. Okay. If I’m talking to people, what do I say? What are the content of my words? How am I simple and concise? How do I distill it down with skill and discipline such that you can understand it? What we always say in the business school is, people will not work to understand your message. You have to work to be understood.


Andy Paul (12:56)

Exactly. And that’s a great phrase. I love that.


Craig Wortmann (12:58)

It’s a totally different deal, but it means that we have to start at the beginning. And we have to literally do this, we throw students in a room and they have to walk up to the Andys of the world say, “hi, Andy. I’m Craig, I run a company called Sales Engine, what we do is help companies build and tune their sales engine.” And then I shut my mouth. Because if I shut my mouth, chances are good things will happen. And sales will begin because you will naturally go, “oh, what does that mean?” And now you and I are in a conversation. It’s about what I can offer you or not offer you, that’s fine, too. If you’re not an opportunity, that’s fine, too. I have to qualify you out. And so, we just lay out the sales process step by step from the very beginning. When you’re looking at a cocktail napkin with a drawing of your potential solution on it, and we say, “great, describe what’s on that cocktail napkin and tell me why in a compelling way.” I should buy that. And it’s so fun because in our first week we assigned something that you’re familiar with Andy, called the Sales Trailer, which is the one-line movie trailer of the business. It’s like, “wait a minute, I’m in an elite MBA program and this crazy professor is assigning one sentence as the week’s homework? I’m going to love this class”, and then they come back in week two, and they go, “oh my God was that hard?” Yes.


Andy Paul (14:15)

I like to do is something similar. I, give one sentence and then they come back and say, “okay, now you get half that many words to explain what you do.”


Craig Wortmann (14:24)

That’s exactly right. And it’s funny because I’ve played with this class over the last eight years, and I’ve done it up six different ways, because I like to experiment and do a little A-B testing. And sometimes if I don’t explicitly tell them, it’s one sentence, I just say, “hey, you got to be clean, you got to be simple, you got to be concise. Here’s what I want you to imagine. You’re literally standing in a hotel lobby. You just met somebody, and they asked you what you do. What’s your answer?” And if I don’t say it’s one sentence, guess what they come back with? These are very smart, talented people, they’ll come back with four paragraphs. And then it’s a hilarious and uncomfortable moment because I literally stand in front of the class. I pull up a student I say, “hi, I’m Craig.” And they say, “oh, Craig, what do you do?” And then I read them the four paragraphs, and of course, by the end, there’s 70 people in my room sweating, because it’s so uncomfortable.


Andy Paul (15:11)

Because they see themselves in those four paragraphs.


Craig Wortmann (15:15)

That’s exactly right. It’s a discipline, and we know this, I did not invent this. Brand consultancies. I’ve known this for years and years, what’s your brand about? You don’t have four paragraphs to tell me about your brand. No, sales is the same thing.


Andy Paul (15:29)

You’ve got eight seconds to capture someone’s attention. So, nothing you talk about in the class is setting expectations. Because this is so important for entrepreneurs, is not to bite off something more than they can chew.


Craig Wortmann (15:46)

That’s right. There’s a couple primary ways that we get to set expectations in a whole bunch of different ways. There’s a couple primary ways. When expectations first start to get set, it’s in the qualifying step, which again, I’m kind of nuts having been a career salesperson. I’m not that, but about the second minute that I meet you, I should start qualifying you, I need to start asking you good questions, impact question and qualifying questions to determine, “who is this guy? What are his issues? Are any of those issues that I could solve?” And now can I share just enough with him to get him intrigued about what I might be able to offer. That’s it. But in that dance that you and I do, I’m going to ask you a whole bunch of qualifying questions, the usual suspects, time, budget decision maker, that sort of stuff, and then some longer tail qualifying questions that have to do specifically with my business. But that is in the spirit of setting expectations. And I’m always careful, especially with my MBA students, because my MBA students sometimes can misunderstand what it means to sell, and when I say that, I mean that they come to the class and this is not pervasive, but they come to the class and they think sales is a synonym for manipulation. And that’s why we go over the myths and why we unlock that, that sales is actually solving people’s problems and helping them, it’s not manipulating you to do something you don’t want to do. And when we talk about qualifying, I say, “look, the minute a customer is either disqualified, or you’ve done enough determining fit to determine there is not a fit with this guy, Andy and this guy Craig, you’re out.” And the best salespeople are the ones that say, “you know what Andy, this has been really interesting, and I really appreciate your insights. It looks like we’re not a fit. But you know what, I know of a couple other resources who are, and I’d love to connect you with them.” That’s what great selling looks like. It is “A”, the right thing to do. And “B”, it is something that– you want to talk about social love, and all kinds of things that accrue to you. And that’s not why you do it, you don’t do it for all that, but you get that. It’s exactly what you get.


Andy Paul (17:55)

And I’ve led my last book with a quote from Jeff Bezos from an interview he did in Harvard Business Review, I thought that was a great definition of selling. He said, “we don’t make money when customers buy things, we make money when I help customers make purchase decisions.” And if people understand that, that’s what they’re trying to do. And sometimes the decision isn’t you, as you just talked about.


Craig Wortmann (18:19)

That’s exactly right. There’s one other thought that I’ll share, and this is a little bit of a nuance, but I think it’s super important for entrepreneurs to know. This is one of those areas where entrepreneurial selling diverges from professional selling, having been on both sides of that fence. We also add a step to our sales process that I teach at Booth, that we work with companies when we consult with them, I call it “resetting expectations”, and your community may raise their eyebrows when they hear me say this. And by the way, they may fundamentally disagree which is fine too. We think resetting expectations is a distinct five’ish-minute conversation that you have with a client after the close, after you close the deal. And it’s almost as a transition to client service, or account management, or customer support, or wherever you want to call it. But it’s the conversation where I say, and it literally is less than five minutes 99% of the time, I say, “Andy, we are so delighted that you’re on board, we’re eager to get started. One more conversation I want to have before we get started, I want to make sure you understand exactly what we’re doing, and what we’re not doing.” And it’s the last half of that sentence that is really important. Because I’m on my game, and I’ve done a great job all the way through with you setting expectations. That should be a no brain conversation where you go, “yep Craig, I see the I see the balance sheet. I see what you’re doing and what you’re not doing. And we’re cool. Let’s get started. We’re excited. Let’s go.” And I say, “great”, shake your hand and we’re off to the races.


Andy Paul (19:49)

That’s funny that you bring that up, I love it because I write about something very similar in my books, and I practice this with my clients and companies I’ve worked with for years. Small companies, startups. Selling complex products is what I call the most important sales call. And it’s just the one you described as after you’ve gotten the order. I set the environment. So, if I’m in a competitive environment, when the customer signs the order, if you were to ask them what they purchased, what they’ve done is they’ve taken the best of everything they’ve heard from all the competitors and conflated into one solution. And so, that’s what they think they’re getting. And so, what you do is you meet with them after you’ve gotten the order, and you just sit down. And what I handle is just review, “this is what your requirements were, this is why we proposed what we proposed. This is what we’re delivering and when we’re delivering it.”


Craig Wortmann (20:42)

Well, I love that you and I are in violent agreement. Because I’m teaching a class for MBAs, I tend to give everything in labels, and so I call that “resetting expectations.” I had played with this over the years, it’s not the right label, and I’m still not sure it’s the exact—it’s not very sexy.


Andy Paul (20:58)

Well, that’s why I call the most important sales call. People might say, “what do you mean the most important sales call?” Because if you don’t have the customers’ expectations and align with what you’re delivering, as soon as you start delivering, they’re pissed off, or they’re disappointing, the worst way possible to start a relationship.


Craig Wortmann (21:17)

Well, not only that, I’ll add one tinier layer to this part of our conversation, and this is where I really differentiate. One of the many ways I differentiate entrepreneurial selling for professional selling, if you’re IBM, back to our IBM conversation, if your IBM and you as a buyer have completely conflated all these competitors, and I haven’t done a really clear job of telling you what you’re getting and what you’re not getting, and we go forward, and you completely get pissed off at me, guess what? IBM can survive that, it’s just it’s just $350,000, it’s not going to take the company down. If you do as an entrepreneur. Good luck. Because you could be in existential trouble doing that as an entrepreneur, and I’ve done it, I’ve been there.


Andy Paul (21:59)

That’s a great point. Excellent. Let’s move on. You referred earlier to the sales trailer. And we talked about that, and I love the metaphor of the sales trailer, you think about a movie trailer, sales trailer. You have this this concept of a story matrix. Then I talk about my related books, you need to have these 32 sales stories and you call them sales anecdotes, which I think is a great a great title, but very similar. So, talk about your story matrix.


Craig Wortmann (22:32)

Sure. This is a tool that comes from my book called What’s Your Story? And it’s a book that I wrote some years ago, it tries to get at, how we as leaders and salespeople tell stories that really ignite performance and just connect to people, engage people in a different way. So, I was running a software company and we actually told stories and shaped them out of large organizations, and then redeployed them across an organization to connect them to important topics like sales negotiations, ethics, ethical dilemmas, leadership, product development, that sort of stuff. I got really interested in why stories work and the psychology. And again, this is sort of my nerdy academic side coming out. Why do stories actually connect? Why have we as humans shared stories over the millennia? And so that’s a whole different part of our conversation we don’t have to have today. But it’s fascinating. And I continually learn how the psychology of stories actually works. In my book is I said, “okay, if we just accept that, if we all as salespeople on this podcast accept that look, telling a great story, telling them the right story at the right time for the right reasons. If we accept that, that’s powerful and influential, and convincing”, then the question becomes, “okay, what story are you going to tell?” And this is where I’m a classic salesman, like, give me the tools. Where are the stories. Tell me the five stories I should tell about this company so I can go tell them, so I can go into that hotel lobby and tell them, because you got to have them to tell them. And I came up with this story matrix. It’s not the matrix from the movie, it’s much more boring and simpler than that. But it’s literally just a spreadsheet. It’s a grid. And it has four types of stories across the tops in the columns. And each row is a different situation where you would need to tell stories. So, I’m early in a customer relationship that might be a row, or I’m hiring people for my cool team that might be a row, hiring and onboarding might be a row, leadership, boil it up to high topics, like high level topics; leadership culture, you’d have a whole row of stories on culture, and the columns across the top are important. And we explore this a lot in my book What’s Your Story? Where I’ve looked at the four types of stories, leaders are telling, success, failure, fun, and legends. And I think those are all obvious definitions. Legend is, I tell you a story about Steve Jobs, he’s a legend. Or I tell you a story, 300 years ago a man was traveling across the world, sort of a historic mythical, religious spiritual teaching story. That’s another definition of a legend. But you know, salespeople tell fun stories, we should tell successes, obviously, we should also tell failures, which is a really interesting topic when you start to unlock the psychology behind it. If I tell you a failure story, why does that actually impact you and affect you in a positive way more than a success story? That’s often counterintuitive for salespeople and executives. I work with a lot of CEOs in my executive education and Executive MBA teaching at Booth, and that’s often counterintuitive for them to because they want to be– they are already successful and we want to channel those.


Andy Paul (25:40)

They want all five-star reviews, and they don’t understand that these days people look with suspicion on five-star reviews if that’s all you have.


Craig Wortmann (25:48)

Well, that’s right. The best example I have in my personal life of that is, I got my second opportunity to lead a company, it was a turnaround about business that was struggling. And when I interviewed the final time for that position with the main investor, who was in a major force in Silicon Valley, I told him my failure stories for my first business, I said, “here’s all the things that I screwed up.” Some of them were embarrassing, just really dumb decisions. And his reaction to that was so interesting and why failure stories are so important. His reaction was, “well, at least you won’t make those mistakes this time”, because you’re able to articulate them. I had walked in there with my chest pumped up, and I did tell them some success stories that I’m super proud of, but not many. But if I’d walked into my chest popped up and said, “hey, I’m the smartest guy in the room.” I never would have gotten that job. Not in a million years.


Andy Paul (26:46)

You’re basically letting the prospect know that you’ve learned the lessons, you’ve gone through the difficult periods, and maybe the competitors haven’t, by virtue of not telling those stories, perhaps they haven’t learned those lessons.


Craig Wortmann (27:02)

You learn the lessons from experience, that’s exactly right. What I always say is, failure stories do a lot of things, but if you boil the psychology down to its reason, what I think is the essence, they demonstrate that you are a learner, which is really important. And then they demonstrate the ultimate, which is humility. If I’m able to look you in the eye, and I it’s got to be authentic, I can’t be just making it up, it’s got to be an authentic failure. And by the way, we’ve all failed, so, it can be authentic. And you asked me for an example, here’s an example of how I screwed that up six ways to Sunday and I really regret that. And you’re going to ask me naturally, you’re going to say, “Craig, holy crap, what did you learn?” And I’m going to get a chance to tell you how I sort of turned it around or what I learned after I lick my wounds, “I figured this out Andy”, but it’s only then that we should be telling the more successful side of that story. I always say to my students, “sit down into your failures. It’s okay.” You will actually connect and be magnetic to people if you do that.


Andy Paul (28:12)

Because you’re, right? People buy from people, but only if they’re human. Before we get to the last leg of the show, I want to touch this because you brought it up earlier. You talked about the impact questions. Describe what impact questions are here. Because this is another area I’m sure we’re in violent agreement on. In my book I call them killer questions. But it’s the same concept and you talk about in a recent video, and I love the way you expressed it, because that’s exactly what I agree with. So maybe talk about impact questions.


Craig Wortmann (28:41)

You and I are definitely in agreement. You call them killer questions. I think Google calls them killer questions as well. There’s a great consulting firm out of Boston that calls them high gain questions. So, I’m just trying to be different and fancy with my little impact word. I just like the word impact, because I want you to come out of a meeting having had an impact in that meeting, and one of the ways we animate that impact, or manifest it is in the questions we ask. Here’s what we know. We know that high performing salespeople get better, more actionable information from their customers. Why? Because they ask better questions. And so, the question about questions is, I’m going into a sales meeting, you’re going into a sales meeting tomorrow. What I always like to ask is, are you conscious and deliberate about the questions you’re asking? Or are you going to ask all the average questions? And let me be super careful here. There is nothing wrong with asking the average questions. There’s nothing wrong with me walking into your office tomorrow. You don’t know me very well. You don’t know me at all. And we’re having a sales conversation and they say, “Andy, how’s your quarter shaping up?” There’s nothing wrong with that question. That’s a really good question. It just isn’t an impact question. Why? Because the answer is right in front of your mind. The definition of impact questions are that they go deeper, they go broader, and the answer is not right on the front of your mind.


Andy Paul (30:08)

You have to stop and think.


Craig Wortmann (30:10)

You have to stop and think. And the cool thing is, every single person listening to this podcast has asked a gazillion, what I call impact questions. You know you have, because somebody went, “Hmm, let me think about that’s a good question.” We’ve all gotten that reaction. I’m just saying, okay, prepare for that reaction, prepare to get that reaction. Walk into that CEO’s office and not in the first minute, it would be like me walking into hugging you. That would be too close, right? That’s just too weird. But 20 minutes in, great time for an impact question to say to Andy the CEO. “so, Andy, you’ve been painting a picture of this year, and it’s really interesting and compelling. Let me ask you a question. If we get to the end of this year, and that picture has gone completely to hell, what does that look like? And what does it feel like?” That’s what I think is an impact question. The cheesy version of that is, “what keeps you up at night?” I think it’s a better way to get at a little edgy. I said the word hell, I don’t think anybody will hold that against me. I’ve literally asked CEOs of Fortune 20 companies that question, and it stops them in their tracks. And that’s exactly what I want. I want them to go, “let me think about that.” Then they start to unspool all this really interesting stuff, and that is better, more actionable information for me. Whether it benefits me or whether it doesn’t. Again, that’s back to our qualifying. It might qualify me out as a solution, but I will understand, after that 40 minutes with that CEO I will get much farther and deeper than the usual person if I’m on my game.


Andy Paul (31:53)

Yeah, and for people listening and I brought this up a couple of times before. Another way to think about these impact questions or killer question is, you’re going to ask the prospect something about their business that they should know.


Craig Wortmann (32:06)

Right. That’s a great way to frame it.


Andy Paul (32:09)

If you think about, it is something they should know, but don’t. That will cause them to pause and think. And that gives you a level of credibility and perception of you having some insight into their business that you can build on.


Craig Wortmann (32:24)

Yeah, I love that. That’s a great way to frame it.


Andy Paul (32:27)

Well, now, Craig, we move into the last segment of the show where I’ve got some standard questions I ask all my guests. And the first one is a hypothetical scenario. And you’ve probably been in the situation and you’ve just been hired as VP of sales at a company whose sales have stalled out, it is time to hit the reset button, get things back on track, the CEO, board are all anxious for it to happen. So, what two steps would you take in your first week on the job that could have the biggest impact?


Craig Wortmann (32:51)

I love this question. Let me think about this for a second. I know the first step. I know both steps. So, I did this in my turnaround company, and this is the reason we turn the company around. One of the two things I would do right off the bat is, quickly assess the three things of each person on the team and each person that surrounds that sales team, their level of knowledge, skill and discipline. And I like those three pillars, they serve as a foundation for my MBA courses and everything I do in my consulting work. I like to look at and assess the knowledge, skill and discipline. And I believe strongly in my reading of the sales research and my experience as a salesperson entrepreneur, that it is the proper balance of those three things that makes up high performance. So, I’m going to want to know is, “is Andy strong and all three factors? Is he not as knowledgeable?” Which by the way, would not concern me at all. It would concern me if you were not skilled and disciplined, that would concern me. Knowledge we can fix, skill and disciplines we can fix to but it’s harder. So that’s one thing I would assess, one thing I would do. And then the second thing I would do is what we did my turnaround company, we started really putting those three things to action by doing a blitz. So, I would I would put us into a sprint, we would cold call, generate as many leads, qualify, push prospects as far into the sales pipeline as possible right off the bat. The reason I do that is not to make people uncomfortable, although it does, and not to be sort of a tyrant, the reason I do that is to figure out what I’ve got. So, do I have people that will come in and make 70 calls before lunch? We discovered goods and bads in our turnaround company, where we had people that said, “this is so far out of my comfort zone, I’m not doing it.” And that tells you a one story. And we had people that said, “god, I hate this, but I’ll do it”, and that told you a different story. And usually those are the people that that were incredibly successful.


Andy Paul (34:49)

Yeah, that’s a great answer because you get to assess the level of commitment to the mission going forward, which is really important.


Craig Wortmann (34:55)

You find out so much stuff. We did a series of sprints over weeks. And it was hard for all of us and I did it right alongside them. I didn’t I never asked anybody to do something I won’t do. I was making 250 calls a week and we were just pounding. And I was terrible at it for the first couple weeks until I really learned what the heck I was talking about. But you learn a lot about the culture of that company in that sprint.


Andy Paul (35:19

All right, excellent answer. We got some rapid-fire questions. You give me one-word answers or elaborate if you wish. The first one is when you, Craig, are out selling your services for a sales engine, what’s your most powerful sales attribute?


Craig Wortmann (35:31)

Simplicity. It’s what we’ve talked about. It’s people who give people crisp answers.


Andy Paul (35:39)

So, who’s your sales mentor?


Craig Wortmann (35:40)

A guy named Keith Harrell at IBM who came in to talk to us and had a profound influence on me. He was a golden circle winner, which means the top of the top at IBM, big boisterous guy, incredibly talented. And I looked at him and said, I want to be that guy.


Andy Paul (35:59)

Great answer. Other than your own book, what’s the book every salesperson should read?


Craig Wortmann (36:04)

Give and Take by Adam Grant at a Wharton Business School.


Andy Paul (36:10)

Okay. Maybe a new one for me.


Craig Wortmann (36:12)

Fantastic. One of the best books I’ve read the last five years.


Andy Paul (36:15

Going on my list with that recommendation. And last question. That’s always the tough one. What music is on your playlist these days?


Craig Wortmann (36:23)

I just heard a great rap song, and I’m not a huge rap guy, but I love this song. I love rap, but I just don’t listen to it a lot. I don’t know what the name of the song is but I can tell you how to find it. There’s a movie that was just made. I think it went straight to Netflix or whatever. But it’s George Clooney and Julia Roberts.


Andy Paul (36:51)

Oh, the financial one?


Craig Wortmann (35:52)

Yes, the financial one. It’s the song that plays over the credits right at the end. I’m sorry that I can’t be more specific.


Andy Paul (36:57)

We’re going to research that; we’re going to find out what that is.


Craig Wortmann (37:00)

That was such a lame answer. But it’s a great song. And I’ve been rocking for the last week.


Andy Paul (37:04)

Okay, great. Well, Craig, thanks for joining me and tell people how they can connect with you.


Craig Wortmann (37:11)

Thank you for asking. I’m on LinkedIn @SalesEngine, or @CraigWortmann. And just to clarify my name, it’s, W-O-R-T-M-A-N-N. So, @CraigWortmann, @SalesEngine is probably the best. My website is super simple at salesengine.com. So, we’re on LinkedIn, and we’re on twitter @SalesEngine. And obviously, you can hit me on LinkedIn. And I’d love to be part of the community.


Andy Paul (37:42)

Excellent. Well, thanks again. And remember, friends make it a part of your day, every day, to deliberately learn something new to help you accelerate your success. And one easy way to do that is take a minute and subscribe to this podcast Accelerate, because then you won’t miss any of my conversations with top business experts like my guest today, Craig Wortmann, who shared his expertise on how to accelerate the growth of your business. So, thanks for joining me. Until next time, this is Andy Paul. Good selling everyone.

Thanks for listening to the show. If you like what you heard and want to make sure you don’t miss any upcoming episodes, please subscribe to this podcast on iTunes or stitcher.com. For more information about today’s guests, visit my website at andypaul.com.