Delivering the Compelling Career Story Craig Wortmann

Anita Brick: Hi, I’m Anita Brick, and welcome to CareerCast at Chicago Booth, helping you advance in your career. We're delighted to be speaking with Craig Wortmann, who is clinical faculty at Chicago Booth, CEO of Sales Engine, and author—and this is what we're going to talk about today—of What's Your Story? Thanks so much for doing this.

Craig Wortmann: Thank you for having me. I'm delighted to be here.

Anita Brick: “Story” is one of those words that sometimes when you say, oh, what's your career story? People feel a little uncomfortable. So let's just give it a little definition. How would you define a career story?

Craig Wortmann: I have a very liberal definition of story that you may find curious. I used to use this stupid acronym, CASE. So character, action, structure—meaning the beginning, middle, and end of a story has to have a structure—and the E stands for emotion. So CASE, and I still use that. But then I sort of make fun of myself and say, well it's not really CASE, it's just character.

So a story has a character because if you have a character in a career setting, and you set that person in motion, you've got a story because you have to have action. If you set something in motion that has action, it has structure and then you can't not have a beginning, middle, and end. And because it's a person, you have a motion.

It may not be high drama, high emotion, but because you are at the middle of that career story, you get emotion. It's one of the benefits you get from the story.

Anita Brick: Oh, absolutely. Because otherwise you have a bunch of facts and somebody else always has a better set of facts. No offense to you, but to me a better set of facts than either of us.

Craig Wortmann: That's exactly right.

Anita Brick: All right. And I actually like CASE, but it has to be compelling. So there was a question from an evening student that said, in switching careers, how can you spin your current story to tell the story that you would like to take in the future? For example, I'm moving from investment research into marketing strategy—not advertising, but marketing strategy.

So how do you spin a story? You've got all this kind of emotion and facts over on one side. You actually want to morph it into something else. How do you do that?

Craig Wortmann: It's a tough challenge. I believe that it begins with understanding what you want. And what's great about this person's question is they know what they want, right? So it's “I want to move from investment research to marketing strategy.” If that's true, the question I would ask, had that person been sitting here, is what do you want from marketing strategy? What interests you?

And then ask them to turn around and look into the past and say, what about the investment research process, the knowledge, skill, and discipline of becoming an investment researcher, did you find interesting? When you began to look at marketing strategy as a potential option for you, what did you find interesting there? And is there a way to marry those two things together?

Is there a way to say, if you were interviewing me and I wanted to make a move to marketing strategy, and you said, Craig, OK, but you're in investment research, why are you here? Why are you sitting in front of me? Is there a way for me to say, you know what, Anita? One of the things that I found really compelling about investment research is when I got to really delve into the inner workings. What makes a firm that depends on marketing strategy—what makes that work? What makes it function? Where is the story there? Where's the compelling nature of that business?

And what that drove me to understand, an insight about myself, is I really got interested in marketing strategy. And here's where I imagine that going. So if I could make a move into marketing strategy, here's how I would leverage obviously my investment research. I don't want to leave that behind. But here's what I would take forward in terms of marketing. And that's crafted in terms of a story. And I'm making that up because I don't know either field extremely well.

Anita Brick: But that makes sense, though, because if you think about it, you think about someone who works at a company like Motorola, right? Let's say Motorola Mobility, where they're, you know, they're making these phones and they really want to get into consulting. But often the bridge is that problem solving. They had to problem solve in an innovative way to bring a feature that hadn't been done before in the same way. And so I like that. So you look at the past not so much to extract the skills specifically, but where the skills and your interest in your passion merge because you get the emotion and the vitality there.

Craig Wortmann: That's exactly right. I mean, that—and that's what animates. And I love this word, right. It animates your interest in marketing strategy. So think about the converse. The converse is really instructive. So I come to you and I say hey and you say, Craig, why are you here? And I say, well, Anita, I've been in investment research.

So I really know how to look at financial statements. I really can, you know, line up and understand the profitability, or lack thereof, of a business. And now I want to move into market strategy. And what I find interesting about marketing strategy is I find, you know, the whole segmentation thing interesting. And I find trying to have a compelling value proposition interesting. All I'm doing is lining up a bunch of facts. You're getting no meaning, right?

Anita Brick: You're right.

Craig Wortmann: You're getting no sense of my desire to be that person.

Anita Brick: And you haven't convinced me that at least.

Craig Wortmann: Right? So I just said, well, fact, fact, fact of investment research, which are all great facts and they're wonderful knowledge and experience. And then I'm turning to marketing strategy and transitioning. What I do in my class called Pivot, I'm pivoting to marketing strategy and I'm giving you facts. Well, fine. But am I really going to differentiate myself on the basis of that?

I don't think I am. If I reach back and say, when I think about investment research and I think about the things that, when I looked at firms that were compelling, all of those bubbled up, Anita, to marketing strategy. Here's how I think about that now, and here's why I'm so intensely interested in being in that field. That's just a totally different feel.

Anita Brick: Well, it does, but you have to do a lot of work and you have to be willing to be, dare I say, vulnerable. You say, well, maybe it doesn't fit. Maybe there isn't a good thing. But if you dig deep enough, there's usually a parallel to virtually everything.

Craig Wortmann: Well, you just touched on one of the key foundations of the power of story, and you use the word vulnerability. I use the word humility. Same deal.

Anita Brick: I like that.

Craig Wortmann: But you also pointed out another key thing in the career context of telling stories, and that is to point out the process. You just said, this may be a real stretch. If I'm trying to get into marketing strategy and I say, you know what, Anita? This may be a huge stretch for an investment research person to do this, but—and then I tell you why I'm interested in marketing strategy, chances are you're more engaged with me rather than less. Because I've shown vulnerability, humility. I've talked about the elephant in the room, which is why is this guy from investment research going into …. Like, what the heck? What is he thinking, right? I've addressed the elephant in the room.

I think so many times in our interview processes we fail to just recognize the process, recognize the big leaps that we're taking, right? And that's a huge piece of setting it up for me to say, OK, I know it's a huge leap, but let me share with you why I have such a desire to be there.

Anita Brick: In the whole differentiation, especially if you are stuck in a weakness in a sense. So there was an alum who had a question, which I think is a common question that I hear. I'm sure you've heard it too. I have more than 20 years of work experience, and I'm running into the quote unquote, you're overqualified objection.

What suggestions would you have for a seasoned professional now like myself? I'm a controller.

Craig Wortmann: It is a tough question. And this notion of being overqualified, I think we have a tendency— where I come back to humility. I think we have a tendency to— and it comes from a very honest place. So it's a wonderful thing that we have this tendency to say, you've got to know, first of all, how smart I am, right? My job is to demonstrate how smart I am.

I don't think that's true. You said it before: I'm not going to be any smarter than the next guy in the room. It's just I'm not. I mean, maybe in a way I will be, but in six other ways, they'll be smarter than I will. So this question of being overqualified, one of the ways I would get at that is to have that person with 20 years of experience ask what I call impact questions.

And impact questions are simply this: if I'm sitting there, I'm the guy with 20 years of experience and you're interviewing me, I may say, Anita, obviously I have a long background in things like this, and I feel like I have a lot of capability. I also feel like I could learn a lot from you and from this firm. Help me understand that. What would that look like? You know, give me a real sense of the work such that I can understand where both I fit in and where I still need to learn.

That begins to break down the overqualifying perception that you may be sitting there having as you're looking at my resume with 20 years of experience, right? It also shows humility. So it's back to that theme again. Again. And again. And it just builds a stronger connection between us that I'm not saying, “Well, let me share with you six more ways I'm really smart because of my 20 years of experience.”

Anita Brick: Another question that came up, this one from an Exec MBA student, which I thought was very humble of them to ask this question. He said, well, how do you answer the question, tell me one of your greatest weaknesses? And I think weakness and failure are very different. And I know we'll talk about failure, but someone says, tell me about one of your weaknesses. People were like, well, I work too hard. Well, if that's true, that's OK. But how would you address that?

Craig Wortmann: I run the opposite direction on this question, and I know it's provocative. I have a very controversial opinion about this. I've shared it in many places, at many different times. You don't answer that question with a success. Because when you say, I work too hard—and I know you're being facetious, and I use actually that one is a great example—what you're saying is, you know, I'm too good. That's not a failure. It's actually a success. And if you can manage me, maybe I won't just kill myself on this job. Right?

I run in the opposite direction. What I call it in my course and with clients is you relax into that question and you embrace it and you hit it dead-on straight up. You want to hear about my greatest weakness? Let me tell you about one of my weaknesses. Now you don't— you may not call it your greatest weakness because that's all relative, but you hit that one head-on because in the process of doing that, I believe you strongly differentiate yourself from the person that came just before you in that interview and just after you.

Anita Brick: So how do you do that and not shoot yourself in the foot?

Craig Wortmann: So I'll give you an example. One of the leadership failure stories, one of the leadership weakness stories that I tell about myself. So if you were interviewing me for the leadership position of an entrepreneurial enterprise or SVP of marketing for some company in Chicago, and you said, Craig, tell me your greatest weakness, I would say something like, Anita, that's a tough question. In my experience as an entrepreneur and as a leader, I've had plenty of failures.

Anita Brick: But there's a difference between failure and weakness. So a failure is an event, a weakness can persist.

Craig Wortmann: True.

Anita Brick: So how do you address the weakness? I mean, the failure, I guess.

Craig Wortmann: Yeah, it's a semantic question. I would address that question in terms of failure. If I had to answer it in terms of weakness, it would be the same story that I would tell, which is a weakness of mine, and it manifested itself in the form of a failure. But I would say in my first company, as the leader of the company, I decided one day that we were going to do 360 feedback because I believed that would demonstrate to the company how serious I took the leadership role, because I was going to get feedback, too. Wasn't just my employees, it was me.

Well, sure enough, as 360 goes, everybody gets feedback and I got feedback. And one of the pieces of feedback I got from one of my employees, this is all anonymous, of course, was Craig, you use the word “awesome” way too much, and if everything's awesome, nothing is awesome.

And this is a story I tell in my book. And the reason I tell it is, of course, I was horrified and appalled and I went through the shock/anger/rejection model that we all go through with feedback when we don't like what we hear. And I finally got to the acceptance phase of the feedback model or the grief model. The woman approached me and the actual person because it was anonymous and said, I gave you that feedback because I mentioned it in a company meeting and that I was trying to learn from it, and I was trying to take the word awesome out of my vocabulary.

The reason I tell you that story is the weakness is I tend to be a very enthusiastic person. I see the glass as 95% full. That can be a problem because when you go to lead people, if your enthusiasm gets the best of you and you begin to paint everything a certain color, nobody can make any distinctions and you lessen your effectiveness as a leader because there's no gradient, there's no sliding scale, everything's either great or horrible.

And so I had to learn to take that out of my vocabulary. Now you can learn from that, but I would consider it a leadership and management failure on my part. And I own it. It happened, I learned from it, but I definitely am an enthusiastic guy.

Anita Brick: Well that's great. And then the weakness aspect of it, as you said, is that there is that tendency to paint everything really positively, which in many cases is a good thing, and in some cases, because people can't differentiate. But to me, the progression is there. You are open to it. Is it a weakness? Is it a tendency that you may have to be aware of? Sure. But you've also made progress.

Craig Wortmann: You learn how to manage it. But notice that I did stop short of adding that piece. And this is where the controversy comes in, because most of my students and most of my clients will say, Craig, that story's not finished. You have to tell how you made it a success. And I say, no, you know, because I would much rather have you look at me and say, you know, you notice the last thing I said was, I own it.

I own that failure. It's my own weakness. I own it, right. I just want you to know that I can acknowledge that and then I'm open to it. You have to be so careful and delicate when you spin a failure into a success. Because 99% of the time when I have somebody do that to me, I say, that's great, Anita, that's a great story. Now tell me a failure story. Now give me a weakness because that was a success. That wasn't a failure.

Anita Brick: Got it. It is a little controversial because some people feel very uncomfortable on both sides. Both the investor and the interviewee, like, well, it's still a weakness with him. I don't want him to fail on my front.

Craig Wortmann: Right. I think embedded in the story is that it's clear that I did learn from that.

Anita Brick: Oh, absolutely. And you took action on it. Absolutely, you did. Along with the differentiating, sometimes people differentiate themselves in a negative way. Yeah. And there's someone here who is a weekend student, and— but he's aware of it. He said, when I meet someone in a networking situation who I want to work for, I have a tendency to want to tell that person everything to make my case.

This doesn't seem to be working for me because I rarely get an interview in that situation. How do I tell just enough in the first meeting for them to want to talk to me again? I think that is a universal challenge. I only have 10 minutes of Craig's time. I’ve got to get it all in.

Craig Wortmann: It is a tendency and we all have that, all of us. There's a framework that I think is useful that I use to tackle questions like this. And I mentioned it in this podcast before, called knowledge, skills, and discipline. We tend to over-rely on our knowledge, me included, right? We tend to walk into situations like that. And just as you said, I got 10 minutes, I got to pour it all out.

If we tempered our knowledge with the appropriate balance of skill and discipline—and I'll give you definitions of those in a second—I think that person who asked this question would be much better served. That is, to determine what is the requisite knowledge that I have to share in that moment such that this person will be interested in me.

Maybe it's a little piece of bio, you know, in my bio, my background, what I'm interested in, why I'm at the conference; could be anything, right? When you're selling or when you're trying to convince somebody to listen to your entrepreneurial business, then it's more about your company, obviously, or your product. But if it's you, you may just capture your short bio in a very tight piece.

And this is the discipline. The example I use is the tool that we talk about in my class called the sales trailer, and the sales trailer is the movie trailer of your business or yourself, but in a sentence that takes both skill and discipline to do not knowledge at all comes from knowledge, of course, but it's got to be distilled and the discipline comes in is just distilling it in a sentence.

So you walk up to me at a conference and you don't know me, and I want to get you interested in what I do. And you say, so, Craig, what do you do? And I will say something like, I'm Craig, I run a company called Sales Engine. And what we do is help firms build into their sales engine. And there's an appropriate long, awkward pause here. There's silence and the silence is enforced discipline. Because guess what? I want to tell you all about it. Because I'm a nut about it. I'm enthusiastic.

Anita Brick: Well, you told us before that you were.

Craig Wortmann: And— but I stopped because that's a discipline and a skill that I've learned. So I have to stop and let you into the conversation. Such as, you say, Craig, what does that mean? Well, Anita, and I can go to the next three clear points, only three. And then I stop again, and then you may say, well, so why are you here? Or how does that look in practice? Or you may ask me any number of questions. I always begin with a question. So you say, well, how do you do that? And I say, how do you think about these things now? Because now we're in a conversation.

Anita Brick: So how do you make that sound conversational as opposed to all right, I have my one sentence. Then I have my three points and it ends up being a bit robotic. How do you create that fluid, real conversation?

Craig Wortmann: I will admit it's clunky at the start. It's a bit robotic. It's like practicing lines as an actor. I mean, you have to just learn—you know, what the folks listening are not getting the benefit of is you have your physicality, so you have your eye contact, and I may reach out and grab your shoulder at some point.

You know, I may just do things, gestures and the way I stand. If I square my shoulders to you, that indicates that I'm really interested in what you're saying, and you should be interested in what I'm saying. So it's all those visual cues that you do, but the pauses. I really am a nut about that, because I believe that it is the best solution that I have found to solve the problem of talking too much.

Anita Brick: Good point. And someone's going to fill in the space, so if you don't, the other person is going to jump in because most people don't like silence.

Craig Wortmann: That's exactly right. So take those tools. There's a skill here. It's part skill, mostly skill, part discipline. And it comes, of course, everything we do comes from knowledge. And that is in these impact questions. So I would walk into— if I were that person who asked this question about how do I stop just sharing 10 minutes worth of stuff? I would have three really good impact— impact questions are just questions that gain you a lot of insights. They’re big questions that people have to think about.

Anita Brick: Usually how and why questions, right?

Craig Wortmann: How and why questions. Absolutely. Open-ended big questions. And I would have those and discipline yourself to say, Anita, I'm interested in knowing why are you here? What are you hoping to get out of this conference, or what are you hoping to get out of this event? And ask a question, and that literally prevents you from saying too much. Because now I have to stop and listen. I just asked you a question. So those two things together, I think, can be powerful.

Anita Brick: There was a follow-on question if I may ask. It was from one of your students. During your entrepreneurial sales class, you talked about the importance of using sales trailers, which you referenced. Would you recommend using the sales trailer tactic in our professional lives, specifically in networking and interviewing? What adjustments, if any, would you make and how do you keep it PG-13?

Craig Wortmann: What I mean by PG-13 is have a little edge to you. Use words or metaphors that are provocative so you're not just the same as the guy that came right before you two minutes before, right? OK, that's what I mean. This is a really good question. When you're networking, I believe you should be PG-13. You shouldn't be like, I'm just making this up on the fly. But let's say I walk into a conference and you're standing there and you've got Anita on your, you know, near your shoulder. I've got Craig near my shoulder, on my chest. And I say, Anita, how are you? I'm Craig Wortmann from Chicago Booth.

You're not even mildly interested, and you say, hi, Craig, I'm Anita, good to see you. And you're, you know, trying to get a sandwich or a glass of wine or whatever. I might say, I'm delighted to be here. I really was looking into this conference because I found X and Y interesting, and I'm really interested in pursuing marketing strategy. What's your thought about that, or is that similar to why you're here? So you know a couple things. You know that I'm interested in marketing strategy. Right. And I share with you some insights or not maybe insights, but just some perspective on why I'm here.

Anita Brick: And then you're asking me.

Craig Wortmann: And then I'm engaging in a conversation. There's three things happening in one quick sentence that I literally just made up. But there's three things happening. So often when people I can tell they're networking with me, they never ask for anything. Why? If you're networking, why wouldn't you ask for something? I do lunches with people where a full hour goes by and we sort of limp to the finish and I'm enough of a jerk to say, well, is there an ask here?

What do you need from me? How can I help you? Because I want to push people to ask for something. And it's not, you're not asking for the sun and the moon. You're just saying, Anita, what do you expect to get out of this event?

Anita Brick: They’re not going to say, Oh, I noticed your company. I want to work for you. I mean, you're not going there. You're asking for something that they can answer and that they probably want to answer.

Craig Wortmann: Right? But let's just play that out. So let's just assume I want to be in— like this earlier question. I want to be in marketing strategy. And you're in, you know, marketing strategy, you work for a marketing strategy for a digital marketing firm, right?

Anita Brick: Yeah.

Craig Wortmann: I might say to you, I'm a Booth student. I've spent a lot of time in marketing and investments, and I've gotten really interested in marketing strategy. So what I hope to get out of this conference is this and this. How do you guys think about marketing strategy?

Anita Brick: And then that opens the door for us to— for me to say something.

Craig Wortmann: Just say something or you walk away. I mean, you know, look, this can go bad. This stuff doesn't work for me yet. You might say, Craig, go, go fly. Right. And that's OK. But I will say the exact same thing to the next person. That's the discipline of this. So the discipline of this is let's just play out the worst case.

You go, Craig, you know, I'm going to go grab a glass of wine. I'm not interested. And you walk away. The next person, I'm going to say, Tom, and I'm going to say the same thing because I'm networking. You don't leave these things to chance. It drives me crazy.

Anita Brick: Well, true. And if I do give you something, when you go and talk to Tom, you may have some new insight that you can then add to it to make that question even more interesting.

Craig Wortmann: That's exactly right. And I want to go way back to a little while ago when we talked about making the process explicit. If you do engage with me, I may at some point say something like, Anita, this may be way too forward to ask, but I mentioned that I'm interested in a marketing strategy. We've been talking about this. Is this something that you all are hiring for? Do you know of other firms that are hiring for this? Because as I've been sharing with you, I'm tremendously interested.

So I'm not saying “give me a job”—that would be really forward and clunky—but I'm making the process explicit by saying, this might be forward of me. I'm saying, Anita, warning: it's coming. I'm about to ask you a full-blown question here.

Anita Brick: And that will work if you and I have connected.

Craig Wortmann: If we've connected. If I walk up to you cold and do that, you're going to throw something at me.

Anita Brick: But see, you and I could have talked for 10 minutes and not connected. So part of your responsibility, or the person doing that networking, is to make sure that a connection has actually been made. Usually that question will fall flat if the connection is presumed but not made.

Craig Wortmann: Exactly. So the question becomes, how do you make a connection? You make a connection through what I call the art of conversation. I am asking you questions. It is very strange. It's counterintuitive. I walk into an event. I'm looking for a marketing strategy job. You could have a marketing strategy job for me. That conversation between you and me should be mostly about you, not about me. Because I know what I'm selling. I'm selling me.

Anita Brick: Right. You're right.

Craig Wortmann: So I need to have a conversation. And not— and please don't misunderstand. It's not about manipulation. It's about genuinely peeling back the layers to discover whether there is a marketing strategy job for Craig at your company. And I need to do that by engaging you in a discussion of marketing strategy. How do you guys think about that? When you work with clients about marketing strategy, where are the pitfalls? Like, what do you think about, how do you work on that?

Do you work in teams? Do you work as individuals? How do you gain that knowledge? I mean, there's four million questions you can think of in the moment.

Anita Brick: And pay attention to see if they still are interested.

Craig Wortmann: Correct. Yeah, right. And I should be pausing between each one of those to let you in. But it's a series of questions. And if we get through 10 minutes, and if I've asked you all those questions and you're still not engaged, guess who should walk away? Me. A, you're not interested in me, or B, we're just spinning our wheels.

Anita Brick: I've got something else on my mind.

Craig Wortmann: Yeah, you got someplace else to be, and that's OK.

Anita Brick: There are a whole bunch of questions about differentiation. Let's pull a couple more. One was from a weekend student and he said, I have a PhD degree in engineering, and I'm currently pursuing an MBA degree in finance and entrepreneurship. How can I sell myself as a person who's both an engineer and has finance knowhow? People seem to be strongly oriented toward the PhD and aren't even considering me for finance positions. How do I better communicate the combination, the amalgam of the two?

Craig Wortmann: If I'm getting a sense in talking to him or her that he or she is from an engineering sense, something is giving me that sense.

Anita Brick: Oh, good point.

Craig Wortmann: Right? And so and I don't mean to— I'm not sort of blaming the person here, but my point is that at the beginning of our conversation, it is how you shape that conversation. So you may say something like, you know, I'm Craig, I'm having this fantastic time at Chicago Booth pursuing finance and entrepreneurship. What you should know about me is that I come from engineering. That experience has really informed the way that I think about finance. And as I think about finance at your company, Anita, one of the ways I would think about it is X, Y, and Z.

I'm acknowledging my background, but I'm not talking to you as an engineer, right? I'm projecting into the future and saying, you know, what's great about my engineering background is I'm very— I don't know, I'm very process oriented, and I love to break things down into its constituent parts and look at it.

Now what's been fascinating about learning at Chicago Booth and finance is how to do that in the finance field, and it's the same process. It calls from some of the same disciplines we have in engineering. But here's what I find interesting about finance. Do you look at it the same way, or when you think about your company and the finance roles in your company, is that something that's needed? Is it something that's missing? Notice I always default to impact to try to get the impact question. That's what I'm doing.

Anita Brick: Well, and it makes sense. As long as you use finance language rather than engineering language, they'll probably see you've already begun to make the transition.

Craig Wortmann: That's right. And that's what you want them to perceive. And again, back to humility, right? You say, look, you know, I have a lot of engineering experience. I have less finance experience, but I'm learning. And is this a place that would help me realize, really embed all the stuff that I've learned?

Anita Brick: And where I can contribute the perspective that I bring from that engineering?

Craig Wortmann: Exactly right. Yeah, yeah.

Anita Brick: So a couple more on that front, OK?

Craig Wortmann: Yeah, please.

Anita Brick: You've been in the industry in the company you want to be for a long time, but not in the exact role. Say you are passionate about the sector and have just graduated from Booth after developing the necessary skills. How do you deliver your story about why you want to take the leap and why you're the right person to deserve this when you're competing against people who have loads of relevant experience? So it's kind of like the last question.

Craig Wortmann: It is the flavor of it.

Anita Brick: Yeah, flavor of it. And— but it sounds like the difference is that there's a level of intensity in terms of competition here that maybe wasn't with the PhD.

Craig Wortmann: The question here is what makes up for a level of experience. So you're going to interview me and I'm going to have one level of experience, and then you're going to interview the next person who has absolutely direct relevant experience that is four times what I have. How could I possibly win that battle, is the question here.

Anita Brick: It really is a question.

Craig Wortmann: Yeah. And I think the question comes down to you. I mean, this is what we talk about constantly in our entrepreneurship program. It is desire. You have got to make a case that what you've seen in your past, what you've seen in your education, has lit a fire underneath you such that you will be a high performer in this role.

Just to put brass tacks to that, one of the ways I would talk about it is if I were in an interview process and trying to make that leap into a new role in an existing company, the first place I would go—This is very specific to this question. So I'm at an existing company. I'm going to a new role at that same company. The first place I would go is why I'm recognized in my role. So I'm making a big assumption here. I'm making an assumption that this person is really good at the role he or she does right now.

Anita Brick: Well, let's make that assumption.

Craig Wortmann: Let's make that assumption. I'm going to assume that that's true. That's certainly true of I think most of my students. So if that is true, I wouldn't even be able to tell a story, Anita, about how I did that, which is, you know, Anita, when I came into this organization, you know, we didn't know each other. I did not have a lot of domain experience in what I'm doing now.

And the way I got that was a combination of just a lot of enthusiasm and desire on my part. Some book learning, and I rounded up the top three people in my division who I could learn from—mentors, if you will—and I studied them. And, you know, one thing has led to another, and I've had a little luck and a lot of things have come together, and I consider myself a high performer in that role. I would intend to do the same thing here.

So where you may trade with me experience in the exact relevant thing that you're looking at, you will gain in those other forms of performance, which is just getting in knee-deep, you know, chest-deep learning on the fly. I am a quick learner. I've demonstrated that both in this current role that I'm in and at Booth. That's where I would go with that one, with shifting roles within a company.

Anita Brick: And it's a really good point, because if you have that credibility, they're going to assume that you can make that switch. The challenging part was all the political stuff. Well, you're really good in this role. You're so good in this role. How can I possibly let you go do another role? So I think, how do you play that kind of story? So now you have to kind of unsettle where you are now in order to sell where you want to go. This is probably more of an issue inside a company.

Craig Wortmann: That's a tough one. I mean, my default on that one is that you make it clear that this is a direction for you. You are in command of your own career. And so to the extent that politics are going to get in your way, I would have the tendency to say, if you challenge me and say, Craig, well, you're too good for the— yeah, we can't let you out of that role, I would say, you know, Anita, it's really wonderful of you to say. I have decided that I need to move on. Now, it is about me. It's. I'm okay. That's fine. I appreciate you saying that, but I'm moving on. So let's make that clear.

Anita Brick: And I want to stay at the company.

Craig Wortmann: Help me get there. Right. Help me continue to be a benefit to this company. It's in the same company. That's pretty straightforward because you could literally name names. Yeah. You know, you should talk to Terry because I think one of the things he would say is Craig's a guy who blah, blah, blah.

Anita Brick: Do you have time for two or three more questions?

Craig Wortmann: Sure, sure, sure.

Anita Brick: So a weekend student said, this is a little long question, but I’m going to read it: In my current position, I interview a significant number of highly qualified interns. Many of them had solid grades and community involvement. But this information alone will not sway my decision. I value an inquisitive mind, someone who is determined to answer those personal questions and follow through so it’s apparent in their life.

A simple question I ask when I consider association is how will this person influence me? How will they encourage me to take more action? Anyway, I'm in the process of shaping my own story to change career paths. I would appreciate your suggestion on how to articulate personal interests that align with career paths, and to what extent we should present personality in the story.

So I think we talked a little bit about the shift. You know, you build on what you've done, whether it's inside or outside the company, how personal do you get?

Craig Wortmann: You probably already know this: I tend to be pretty personal. And the reason I do, it's not just because—and it is, by the way, I will admit, honestly, it's part of my nature, but I also do it consciously. Meaning if I show my personality and that does not resonate, that is not a place I want to be. I won't be successful and you won't like me, and I won't like it either.

I tend to coach people to show your personality. That doesn't mean jump up into a song and dance. That would be inappropriate. So there is a line. It's like joke telling. There's a line, right? You know, you get halfway through a joke and you know, you're out over your skis, right? That's not a good thing. And so you know where that line is. It's like we teach ethics here. You’ve got to know where the line is. Right?

I think this person's question comes from a great place, which is should I talk about my personal influences? Yes, you should, as long as they're appropriate. Right. But if you love kids or you are influenced by your family or taking care of people or community involvement, that's something that people should know sooner rather than later. In fact, they should know that before you walk in the door, because that is a key part of you. And if that's not going to resonate, neither party is going to be happy.

Anita Brick: Very, very good point. Because if you go in and you pretend to be a certain way, no matter how great a story—because you can convince most people, can convince many people of things—but you may sell yourself into a job that you absolutely hate.

Craig Wortmann: That's exactly right. And so let me just attempt to put a finer point on this. When it comes to the use of story, one of the ways I use stories in this exact context is I tell stories about my family, or I'll tell a story about my friend Danny, who's a real guy, who's very close to me, and I have a tremendous amount of respect for him.

And every once while, Danny and I will read the same book and then we'll debate it because he is a very smart guy, but he also has opinions that are very different from mine, and I find that it's such an intellectual challenge to talk to him about this, because I learn so much about the subject matter, but I also learn about myself and my own biases, and he does the same thing.

And so we have this wonderful relationship. I will tell a story like that just to demonstrate to you that A) I have friends, B) I'm totally up for an intellectual challenge, and I'm willing to change my mind if you can change my mind because I actually look for that. I engage this friend because I know he's going to come at me from a completely different angle that I can't defend, and I'm going to be forced into a situation to really make up my mind.

You know, back to this guy's question. That's a personal influence, a story that I would share at the right time in the right context of a meeting.

Anita Brick: Actually, that's a great example because it demonstrates so many different things. Like you said, you're social, you are open minded, but you also have a strong opinion yourself, so you're not easily swayed, but you may be convinced based on the facts and other arguments and stuff like that.

Craig Wortmann: There's some flexibility there, right. And, you know, that can manifest itself in all kinds of ways. Back to that person's question, I would encourage him or her to just share that type of stuff. Be your own judge of appropriateness. Don't get out over your skis. But yes, if you're going to err, err on the side of sharing personal stuff too, why not?

Anita Brick: And you should know enough about what is in the range of appropriateness if you've done some homework to have fun.

Craig Wortmann: Absolutely. What underlies this whole conversation is what you just said. And that's homework. We struggle with this in my class because we have so much to cover and so little time. But we talk about stories. One of the underlying assumptions I'm making is that I'm preparing. So when I go to this event and you're in marketing strategy for some digital marketing firm and I walk up to you, I know that. Or I may not know you, but I've prepared the impact questions. I'm ready for that.

There's always wonderful room for improv, but I really like people to prepare for those. And even if it's a little clunky and robotic at the start because guess what? By the time you get to the third person in that conference, you're smooth. You can't help it. But that's why I encourage people to say the same thing over again. I also—this is the crazy tool that I use—not a tool, but just a suggestion I make to everyone: practice this stuff out loud.

Anita Brick: I would agree.

Craig Wortmann: I mean, in a sense and you know what you and I are doing right now is practicing, right? Yeah, we're practicing. And so when people go to a conference, I get a lot of young entrepreneurs in Chicago who call me because they've heard about the sales trailer or they heard about the art of conversation. And I don't know these people—they’re literally on the phone and they say, oh, that's OK, Craig, that's interesting. That's a good idea. I'll do that at the next conference.

And I say, great, let's do it right now. Right now on the phone. And they, you know, they're clunky and horribly awkward. I say, great, say it again, say it again. And we just go over it again. Because if you don't say it out loud, you can't hear yourself say it. And if you say it out loud, oftentimes it's too long. And that's where the discipline kicks in. It's like, Craig, stop. Get it shorter.

Anita Brick: No, you're right. Here's an interesting question from an Exec MBA student. And he or she said, what is the story that impressed you the most, and what are its key attributes? So if you ever run into someone who had a very compelling career story that you thought was really great and why was it great?

Craig Wortmann: I'm a story guy, right? So I have a million examples. The one that occurs to me right now in the moment is the most recent. For obvious reasons. My brain needs to retain all the stuff. But, there's a guy who is a Booth entrepreneur, and so he graduated a couple of years ago, and I have the great fortune of knowing this young man.

He started a company out of Booth that's becoming very successful. And he spoke to my students and he told a great story. A student of mine said, how did you raise all this money? You just had this little idea and it wasn't a world-changing idea. It's— on its face, it's pretty straightforward. I wouldn't call it mundane. It's cool, but it's not Google cool.

It's just another company and the economics are not huge and the scale is not—this is not gonna be the next IBM. And the students said, how did you raise money? And he said, you know, I went and socialized this idea. I found a bunch of investors, a bunch of angels in Chicago. I networked with them. I went to them and I told them my story, and I told them explicitly that I was not asking for anything, but that maybe someday I would be. And a year later—because I knew I was starting my business and I knew I was going to need some capital. And a year later, I went back to them, and every single one of them invested in my company because I had laid the groundwork.

That's one of the best stories I've heard in a long time, because it answered the question that my students had: to raise money. So he broke it down to a tactical process that he followed. But it's such a great story because this young man was very prepared. He knew what he wanted. He knew he was going to need money. And he started 12 months before he thought he would need money, getting the market ready to receive what he was selling. That's beautiful.

Anita Brick: And I think it is absolutely essential, because people start a nanosecond before they need whatever they need, whether it's a networking contact or funds or in a company or a job. So that's a very big lesson.

Craig Wortmann: What did I do in my first business? That. And guess what I did? I raised all the wrong money from all the wrong people for all the wrong reasons. I didn't know I was doing it. It wasn't malicious or ill intended. I just started yesterday and so I needed it, and I needed it now. And so you get money from—and they're not the wrong people because they're bad people; they're just the wrong investors.

What he did is he was much more deliberate, prepared and thoughtful about how he did it. But there was an ask. It's sort of weird. It was an explicit—not ask, but in this, in the sense of him saying, Anita, I don't need you now, but I want to tell your story in case I ever need you, because this thing's going to be amazing. I mean, talk about the way to raise money. Twelve months later, boom! They're all on board. They're all still on board. All he has to do is write an email. If he needs money, he gets money. Well, that's the way to raise money.

Anita Brick: That's great. That's probably hard to top. Maybe our final question will be this: people listening are listening to this specifically because they want to tell a story. They're in transition. They're starting a company. They're doing something where they need to convey. What are three things you would recommend that they sit down and do now to begin crafting that compelling story?

Craig Wortmann: Thing number one is to begin to recognize the stories of your experience. Your best stories come from your experience. I guess the first thing I would say is relax. You have the stories. I think so many people have trouble with this notion of telling stories because they think, OK, so OK, great. So I'm sitting down with a blank piece of paper and I write once upon a time, and then I don't know what to write.

No, that's not what we're talking about. You have thousands or tens of thousands of stories already inside you. And what I try to propose that people do is—suggest that people do is reflect on all of the key decision points in your career. How did you get your last job? What happened in the process, getting that job? When you had a blow-up with your boss in that job, what did it look like when you had your first big win? What did it look like? These are all stories. When you gave a junior employee feedback and it blew up in your face, what did it feel like? What did it look like when you told your mom and dad that you were leaving IBM? This is a personal story. To start a company: What did that look like? How did it feel?

But it's all those key transition points of your entire life, and you don't have to go back to when you were three, but go back the last five years. What are the key points about Chicago Booth? What are the stories? Here's another way to get at that. What are the stories that you'll be telling in 20 years when you're at your Booth reunion about your Booth experience? Those are stories.

Anita Brick: How do you structure the stories? This—OK, so I can think of a story. How do I then—what questions do I ask myself to get all the details that are going to make it robust and vital?

Craig Wortmann: The first one is character. Ideally it's probably you, or it might not be you. It might be your boss and some employee at your firm. That was a story that you witnessed or heard about, that informed the way you do what you do. You don't have to be first person. So the questions you ask are: Who was it? What was the key? What is the core truth or moral to the story? So every story has a moral to the story. What is the core truth?

When I discovered I said the word awesome, every other word. What was the lesson? Well, the core lesson is, Craig, you're over enthusiastic and people can't discern what you're trying to tell them because you're using the same terms over and over again. So that's the core truth of that story, and then there's the story around it. So it's the core truth of the story. So what do I want people to take away from that about me? What should you discern about me based on that story I just told you? I'm smart. I'm stupid. I've made a bad decision. I recovered from a huge loss. I had a great victory.

There's all kinds of different things you would take away. I tend to characterize them in four types. So success stories, failure stories, fun stories. Because there are just fun stories too; we have experiences that are just fun and fun to relate. And then legends, which are a different brand of story, which is, we all know stories about Warren Buffett or Steve Jobs. We know these stories because we all operate in the same culture. That's the fourth type of story.

So the first thing I would suggest is go back, look at those key transition points. The second is, ask these questions. Who, when was it, and what's the moral of the story? The subordinate one is categorize it. Is it a success generally? Is it a failure or a fun story? It was funny because—but it was a failure. Is it a legend? And then the third one you're going to know already. And that's just practice. Tell the story. Tell it to your dog. Tell it to the mirror. Doesn't matter. Do it in your car.

I am—part of new stories, every week, I get in my car and I tell the story to myself because I always tell the long version of the story first. Because I don't have access to the short version. I'm not good at it yet. If I walked out here right now and a student said, Craig, what have you done for the last hour? I can tell a story about recording this with you and having this great conversation, but I would tell the long version because I would tell what color you're wearing, what stupid thing I said I didn't mean or, you know, I was confused, or you had a great question over there, or … I would tell a story, but it'd be long. I have to practice that to get it tight. And that's the use of stories in the career context is get them tight. And the only way you can do that is through practice, preparation.

Anita Brick: That makes sense. Thank you so much. This is great.

Craig Wortmann: Thanks for thanks for having me. It was fun.

Anita Brick: It's really fun. And Craig has great stuff on his site, which is salesengine.com. And thank you all for listening. This is Anita Brick with CareerCast at Chicago Booth. Keep advancing.