Craig Wortmann, entrepreneur / professor / speaker, and Ben Freeberg, venture capital funny man, talk about sales. And how turning the practice on its head can help people make progress in their lives. 

Ben Freeberg: Hello everyone, and welcome to another episode of the new podcast series with TEDxAsburyPark. I am one of your MCs and a co-host for what is now the Spring 2021 TEDxAsburyPark conference. We are recording this right now in the middle of the coronavirus epidemic. I am here excited to be with one of my good friends, Craig Wortmann. Welcome, Craig.

Craig Wortmann: Hey Ben, how are you? It’s so good to be here.

Ben Freeberg: Thanks for joining. My friend Craig is a Kellogg professor. He’s an entrepreneur. He’s dabbled in venture capital, and he is here to talk to us today about the joy of sales. So Craig, can you start us off and tell us a little bit about the origin story of your talk today.

Craig Wortmann: You bet. Again, Ben, thanks for having me. This is really fun. I have come full circle on this thing called sales. I was super-lucky after I got out of college to have been hired by IBM to be a salesperson, although my business card said marketing rep. So I’m not sure what’s happening there. I was thrown from the federal government, where I didn’t know anything about business, technology, or sales into a territory of 13 ZIP codes on the South side of Chicago. As you can imagine, it was just an unbelievably terrifying and wonderful experience. It was a long time ago, right out of college. IBM gave me a tremendous gift by just trusting this dumb young kid to try to figure out what sales was all about.

When I say full circle, I mean, I’ve been through now in my career spanning, I don’t know, 25-plus years, I’ve stopped counting. I’ve been through multiple sales roles, I’ve sold multiple different kinds of things, run a few companies. As you say, dabbled in venture capital trying to help portfolio companies grow. So I’ve been looking at and now teaching sales, and I’ve been looking at this thing for years now from multiple angles.

It is so fun to have the chance to sort of step to the side of this thing and look at it and just see how sales has changed. It’s incredibly different than it was when I got started and what it was for decades and decades before that. I think it indicates opportunities for all of us in the way we think about what this profession actually is. So super-fun stuff.

Ben Freeberg: That is awesome to hear, and I’m glad IBM took a chance on you.

Craig Wortmann: I am, too. I’m very lucky.

Ben Freeberg: So what’s amazing is I’ve had the opportunity to hear you talk about sales quite a bit, when we both worked together with your role at Pritzker Group Venture Capital. What’s so funny is that most people do not really associate the process of sales with “joy.” It’s more the closing of sales. But when I hear you talk about the process and getting to that endpoint for them to finally say “yes”, you’re one of the people that I think finds the most joy in that idea and that process. So can you share a little bit more about that and how you turned that on its head?

Craig Wortmann: Yeah. That’s the perfect phrase, Ben. Turning it on its head. What I say to people is great, high-performing salespeople are actually sad when the deal closes. That just completely turns it on its head. One of the things, my friend David Schonthal, who you also know… I just admire David. He’s spent a lot of time thinking about ‘jobs-to-be-done’ theory and how people make decisions. One of the things that he said one time has just stuck with me and I’ve said it now a million times with respect to sales. He said, “Everyone you come across is trying to make progress in their life.” That is so true.

Craig Wortmann: What is so joyful about sales, I think that it’s turning into … The big idea here is that sales has changed fundamentally. And right before our eyes, it’s turned into the most joyful profession you can have. Why? Because you’re actually helping people make progress in their lives. Ben, it’s so interesting.

Ben Freeberg: Amazing.

Craig Wortmann: It’s funny because people in sales will probably roll their eyes like, “Craig, of course,” right? But everybody else coming to sales or thinking of their experience of sales can be kind of yucky and just weird. What I think is the big deal and what’s changed fundamentally, even just in the last 20 years that I’ve been doing this, is people come to conversations so much better informed. They come knowing their options. They come having, I don’t know, comparison shopped and read reviews. They get smarter, and that’s a fantastic thing.

Craig Wortmann: But what’s actually happening is that the process is fundamentally changing the role of salespeople. Salespeople now, we have to enter that conversation with a much different, much more productive, positive, and growth-oriented mindset, such that, we ask the question, “Hey, I’m meeting this guy Ben or this person Susan. How can I help her make progress? What is my role here to help her make progress?”

Craig Wortmann: What’s so interesting is that whereas sales used to be like, “I’ve got something, Ben. I know all the information, you know relatively little,” I can pretty much do whatever I want in this conversation to see if I can get you to buy this thing. Well, of course, we have this notion that sales is yucky, of course we do.

Craig Wortmann: Now what I say is, sales is much more akin to parenting. You don’t tell your child what they want, you help them discover it. You cut through the noise. You help them see the options. Most importantly, you’re just there. You’re there as a trusted guide and you guide them. You’re a sherpa, right? You’re carrying a bunch of stuff up the mountain in support of the person who’s climbing, and you’re handing them what they need and getting the hell out of their way when they don’t need it. This is what is so incredibly joyful. That whole thing, helping every single day, basically all day long, except for the crappy paperwork that we all have to do, is helping people make progress. I mean, that’s just the coolest thing.

Ben Freeberg: What I love about your idea and how you go about it, Craig, is that it’s not just the joy for you as the salesman, but it’s bringing the joy to the person at the other end of the table and who you’re selling to, which is amazing.

I was reflecting today on some of the things that you’ve shared with me. One of the things I really took away was your love of writing letters, handwritten letters, even in today’s age. I know you’ve talked about how the sales process has changed. But can you talk a little bit more about, aside from helping them with progress, how little things like that help engage the person you’re selling to in a way that I think a lot of people going into sales, and people being sold to, don’t really feel?

Craig Wortmann: Well, I mean, yet another thing I love about you. You’ve nailed the …one of the things that brings joy in any relationship, forget the word sales, in any relationship, are the moments. Dan Pink has written about this. The Heath brothers have written about this. Some really smart people.

Ben Freeberg: I just finished the book, The Power of Moments, two days ago.

Craig Wortmann: Love, love that book.

Ben Freeberg: We’ll do a whole other conversation offline about that.

Craig Wortmann: I’m in, I’m in. Opt-in, as my friend Suzanne says, opt-in. Here’s the thing, there’s this sales process, right? So often we leave this sales process as this sort of generic, sterile thing, step by step. Look, it can be. Any process can be very sterilized. Like first, I do this, and then I do this, and then I do this. That’s fine, and we have to do that. That’s doing our jobs. But one of the things that we’re waking up to, and one of the things that really great salespeople understand is, how might I create a whole bunch of moments?

Again, I’m going to change the game. I’m going to be very counterintuitive. One of my favorite moments in sales is when I realize very early on that I’m not a fit. And I get to say, “Hey Ben, you know what I’m realizing in this conversation as I’m exploring some of the needs that you have and the challenges you’re facing? I’m actually not a good fit. My solution’s not a good fit. Here’s the deal. My very next move here is to introduce you to three people who will crush this for you, and I am delighted to do that.”

Ben Freeberg: I love that.

Craig Wortmann: I’m telling you that like my skin crawls when I even say that to you, Ben. It’s like people will…

Ben Freeberg: No, I hear it in the voice.

Craig Wortmann: It’s like this. There’s this long pause, and they’re like, “What did you just say?” And then you do it, and they’re so thankful. That is my job. My job is to help you make progress. It doesn’t matter whether I get the deal or not, because guess what? That love comes around. Believe me, it does. That’s one moment.

Another moment somewhere in the middle or somewhere towards the end is a handwritten thank you note. Another moment is calling someone’s … We talk a lot in sales about stakeholder mapping. One of the ways to use a stakeholder map is not just to get your job done and make the sale that is to be made, assuming you’re the right fit. Another way to use the stakeholder map is to say, and again, assume I’m selling to Ben, and I’m having this great time with Ben, and we’re clearing a bunch of crap out of his way, and we’re finding the right path. I’m being a good guide, and he’s being great. We get off the phone. I might look at my stakeholder map, and I might call his boss Susan. I might say, “You know what, Susan?” And I might just leave a voicemail. “Hey Susan, this is Craig Wortmann. You may or may not know that I’m working with one of your colleagues, Ben, on this project, blah, blah, blah. And you know what? I just want to say that he’s been fantastic through this process. He comes informed, energized, interested, asking great questions, and it is a pleasure to work with him on this project. You know what, Susan? I don’t know if we’ll get to the end, but I just want you to know, and I wanted to give you some positive feedback about this colleague.”

I mean, that’s just a moment, right? But it’s something that I can uniquely do, because I’m in this fight with you. I’m in this discovery, this climbing the mountain, whatever the heck metaphor you want to use. This is another angle, Ben, in our conversation. It’s what we’re just starting to teach in business schools that is so exciting. Because as you say this stuff in a classroom and you have 70 students … I have 70 students, another great source of joy. I have 70 students look at me like, “Holy crap, I never thought that sales was that. I thought it was this manipulative game that you play where it’s like you’re holding something behind your back.” And it’s like, “Oh my God, guys. No, no, no. That’s not it at all. It’s just helping people make progress.”

Ben Freeberg: Right. Why I love that is because you’re taking away the formal timelines and the nudges where you have people fall into certain parts of your pipeline and then it comes back up. And, “Oh, it’s been two weeks, we should nudge them.” When you change the way you think about the whole process and creating like a little phone call like that. That’s better than three pings.

Craig Wortmann: Oh, my God.

Ben Freeberg: So it’s just being more efficient, which is amazing. 

Craig Wortmann: Well, one of the ways to capture that, Ben, when I was researching my book on stories, my What’s Your Story book, I read a book called The Story Factor, one of my all time favorites by Annette Simmons. She has this great quote that had jumped off the page at me, and I use it in this context all the time. She said, “You are not a bulldozer, you are a magnet.” I’d love that because if we do these things well, and we treat this as helping people make progress, and then we go above and beyond or do it in a really bespoke and joyful way, you don’t have to really nudge people. Yeah, sometimes you do, of course. Life intrudes and people get busy, and they ignore you. Whatever. But sometimes you have to nudge. But many times you’re absolutely a magnet and people come to you, because you’ve created all this joy through the process.

Ben Freeberg: Which is amazing. That makes so much sense. Craig, I am so sorry to do this, but we promised our listeners that we’re going to keep these to under 15 minutes, and we’re already so close. That flew by.

Craig Wortmann: No worries. It did fly by.

Ben Freeberg: But before we let you go, a few more questions. One, if our listeners want to do more, engage more with your idea, what are some steps they could take?

Craig Wortmann: Oh yeah, well the usual suspects, Ben. I am quite active on LinkedIn. I’m active on Instagram. I dabble in Twitter and in Facebook obviously. Then, there’s a lot of people doing a lot of cool stuff. I mean, we mentioned a couple of them already, Dan Heath, Dan Pink. Why is everybody named Dan?  

Craig Wortmann: Daniel Kahneman. All talk about this.

Ben Freeberg: Dan Ariely

Craig Wortmann: Even folks like my friend Linda Hill at Harvard. She is the go-to person on becoming a manager. I reread that book lately; and in between the lines, it’s all about these touches, right? There’s a lot of people thinking and writing and talking about this stuff.

Ben Freeberg: Awesome. That is great to hear. To our listeners, you’ll be able to hear more about Craig, his story, and the joy of sales. Hopefully, it made you guys think about it in a little bit of a different way. Hopefully, you can all apply this to your daily lives. We’re starting to do some online salons over the next few weeks. So keep an eye out. For those of you that are subscribed to TEDxAsburyPark, you’ll see some notifications coming in the mail.

So Craig, thank you so much again for the time today. We’re excited to hear the rest of your talk, and thanks for changing the way we think about what seemed at first like a very traditional process.

Craig Wortmann: Well, you bet. Thanks for the opportunity. Great spending time with you, Ben, and I hope this was helpful to everybody listening.

Ben Freeberg: Awesome. Thanks, everyone.

Share This