The Power of a Compelling Career Story

Anita Brick: Hi, this is Anita Brick and welcome to CareerCast at Chicago Booth. To help you advance in your career. Today, we're delighted to be speaking with Jim Signorelli, who is an advertising executive. And his career has been spent at major national advertising agencies. His clients have included Citibank, GE, Toshiba, Burger King, International Harvester and many, many more. Jim is the co-founder and CEO of Story Lab.

Crane Chicago Business has cited his firm as one of the top 25 agencies in Chicago, and it's been named to the Inc 5000 list for the last three years. Jim, thank you so much for making the time. I know you're super busy, and also thank you for writing a wonderful book, story branding.

Jim Signorelli: And I'm very excited to be here.

Anita Brick: And you know, when you think about story branding, if we can't do it for ourselves, we can't really survive in the world today. So just to get us started. What do you consider to be key building blocks for a compelling career story?

Jim Signorelli: Can I back up just a little bit and explain the basis for why stories in the context of seeking employment amassed a lot? Why stories? What's so great about stories and the scientific answer to that? Psychologists are proving our brains are really hardwired to think in terms of stories. They help us to process information better than perhaps any form of communication outside of that.

Anybody who's ever told a story and that's just about everybody here, would readily agree with the fact that stories are engaging. They help us to relate or empathize with the storyteller. But the biggest, best reason for using stories in any persuasive communication comes from a quote I wish I had written as it really sums up something I strongly believe in and underscores the biggest benefit of story.

Storytelling reveals meaning without committing the error of defining it. And it was by Hannah Arendt is a political philosopher, you know, and it's something we tell our clients all the time. It's one thing to tell people who you are, or to find for them how they should position you or think about you in their minds. Yet it's quite another to get them to position you the way you want them to do, by their own volition.

Another way of saying the simple way to lead them to water. But don't make them drink. Give them enough incentive to want to drink and get involved. And that's what stories really help do. So to more specifically answer your question, consider the key building blocks of a compelling career transition story, first and foremost, knowing why that transition was made and really doing the proper introspection to get at the reason why, and then to construct that in terms of a story.

I made a career transition. It was in promotion or function of marketing, just as advertising. I was with an agency that specializes in promotion. Here's the story. One day, while I was working on a project, it occurred to me that we were really missing some strategic opportunities, and for my employer, who ended up hiring me, I listed those off.

Got him to agree that, yes, those were some important issues. And I concluded by saying, you know, despite this, I wasn't able to do much about it. And I told my interviewers that I wanted to be at the forefront of the strategy. And I felt that promotion was more executional or tactical. And I'm glad I did get a taste of promotion because it helped me to understand its importance more than I could have otherwise.

But I did find out myself that I have this proclivity for analytics and the reasons why a given strategy was being used, as opposed to being handed a strategy to execute. That did me good, and I think it worked a lot better than had I said, well, I decided that I really wanted to do something different that was more in line with my skills and my talents.

I zeroed in on a particular instance that helped me to realize what the problem was, and I talked about, you know, the outcome of that realization. And ultimately why I made the change I did. The derailing comes from telling people and not showing them, not demonstrating.

Anita Brick: It sounds like what you did was you knew the why, but then you gave almost like a little glimpse into that pivotal point for you, where you allowed them to see from your point of view. Yes, it's relevant to them. An example of how you came to that realization, but also what it could do. So it was the why, but then also a real life example, a mini one. It was a good one. In addition to those, are there other things that need to be in a compelling story?

Jim Signorelli: Think about what a story is and there's lots of different definitions for it. But the one I come back to is a story. Is a character overcoming an obstacle to achieve some goal. Probably the most important component of the story is the obstacle itself. A story is in the story without a conflict, without something that has to be thought through, without there being a problem that has to be solved.

That's what makes stories a story. You know, when you're thinking about how to communicate your why, as I did in this case, think about the obstacle that you're trying to overcome. That's probably one of the most important things to do, because otherwise you're just telling it. Without that definition of the obstacle or the problem that you're trying to solve, you're just telling people by involving people in the conflict and explaining to them why you saw it as a conflict. You do a lot of things. You tell them how you think. You tell them the kind of person you are. You tell them what you value, and you do that without telling them. Yeah, I think that's key.

Anita Brick: Okay. So you talked about obstacles. I think some of the questions ahead of time, it seemed like most of the questions were around some obstacle then having to create a story that went beyond the obstacle. First of all, someone said, I've spent the last four years at home taking care of my kids while my wife established her legal practice. How do I create a solid story so that I don't appear stale?

Jim Signorelli: I would redefine the obstacle. The obstacle is, in this case, has to do with something that costs you to take time off. You know, I had a personal interview not too long ago. He had the same thing. He had a year and a half missing from his resume. When I asked him about that, he told me a story about his son who contracted stomach cancer and how he felt that he was, you know, in the horns of a dilemma and had to make a tough decision about what really was important.

And I decided, he said that, you know, I needed to be with my son at whatever cost. And yes, you know, 18 months missing from my resume will probably be the most important 18 months of my life. And I was blown away. Am I okay? You answered that very well, told me a lot about himself without telling me or explaining the rationale, and was really presented in the form of a story about his relationship with his son.

Anita Brick: Well, it's interesting because there was a question from a weekend student, it fits in really well here. It says, when is a story too personal for a business situation? So clearly you didn't think that this father talking about his son having a really serious illness was too personal? When is a personal story too personal to tell?

Jim Signorelli: Big one's a business, a religion, politics and sexual preference. So like everything else, I would tell anybody he was looking for a job. You're going to be hired not just for your skills, but you're going to be hired for your beliefs, your values, the kind of person you are. And you should feel free to expose yourself so that whoever you're talking to gets an accurate impression of the kind of person you are.

You have to use your discretion. Stay on the safer side, but at the same time, don't be so safe that you stick to facts only and avoid any personal stories to the point where you sound like just about everybody else is in there. Reveal your personality. Reveal who you are as a person. There's more risk in not doing that.

Anita Brick: Okay. Fair enough. So that alarm had a question, another dilemma, another obstacle. He said. I was fired from my firm after making a mistake that cost millions of dollars. I work in a fairly niche industry in which word spreads quickly. Given the enormity of the loss and the bad blood that now exists between me and my former employer, I feel like I'm walking around with a scarlet letter on my chest. How do you tell a compelling story? If a significant black mark is front and center on your record?

Jim Signorelli: That's a challenging question. I won't deny that. I would suggest, without knowing the specifics, that the story might be about what happened, of course, and what was learned as a result of what happened. I don't think you have to wear a hair shirt and tell everybody, I'm going to spend the rest of my life dealing with heavy guilt, but I think you need to be realistic, and you need to be straightforward, and you need to admit to whatever happened in a positive way, as you possibly can, with the understanding that you really learn something from it.

If there's a way to demonstrate that you've learned from it. The second time something occurred where this could have happened, all the better. But you know, if you're concerned about wearing a scarlet letter prior to and during the interview, unless it comes out, you will be trying to hide something the whole time you're employed. And that could be very stressful.

You know, you're always wondering when you're going to be found out. Better to face the facts and to tell the story in the most positive light you possibly can without casting blame or without sounding like you're not taking responsibility, but nevertheless come forward and be forthcoming.

Anita Brick: It's going to raise some kind of red flag anyway. We kind of know that.

Jim Signorelli: Think about it this way. I doubt if the first question you're going to be asked in an interview is, I understand you made a $1 million mistake. Tell me about that. Probably the first question you're going to be asked is tell me about yourself. You are going to be given plenty of opportunity to win the win over whoever you're talking to, with your stories about who you are, how you think, what you believe, what you value, and win that person over to your side such that they will be in a position to better understand the problem, empathize with you, and maybe even support you or your reasons why for it occurring.

Anita Brick: Absolutely. And then definitely be prepared for what's your reason for leaving. That undoubtedly is a question that virtually everyone is going to be asked. You know, there was another question, this time from an evening student. I recently left a company because they were doing things I thought were unethical. There were other reasons as well, namely general bad management. How do I tell this story? My biggest concern is sounding like I'm badmouthing a former employer, and I know that that is a disaster.

Jim Signorelli: Well, it is, and less trust has already been established. And in an interview situation, there's still a lot of not distrust but skepticism. So you don't want to bad mouth somebody right off the bat, you really don't want to bad mouth anybody. Anyway, I think the best way to go about doing that is to answer the question in a roundabout way with something like, well, let me tell you a little bit about myself and the kinds of things that I believe in.

Then express something that you've learned. I firmly believe in that. And I am pretty much dedicated to that and will be wherever I go. I think it's important for you to know that about me. If probing persists and the interviewer says, well, wait a minute, I understand that there was a problem with honesty, you know? Or tell me a little more about that. Turn the table. You'll get a lot more credit for that. You'll be seen as somebody who's very diplomatic, who knows how to handle a difficult situation.

Anita Brick: I would agree with you. I think that's in part a way of answering that question without saying anything bad. What I came to realize is that the values of the organization were just different from mine.

Jim Signorelli: Could just come right out and say that.

Anita Brick: You said it's all about taking responsibilities. People feel very uncomfortable when we say anything bad about a former colleague, a former employer. You and I both said it's treading lightly in this area and taking responsibility and then moving through it in a way that answers the question without derailing the whole interview.

Jim Signorelli: What's most important in an interview session is to help the interviewer understand how you think you will be judged in terms of how you dealt with it. Awkward situation, how you dealt with a difficult question.

Anita Brick: You know there was one other, one other obstacle question. A weekend student said my career progression to date has been fairly disjointed. I started as a news reporter, moved to recruiting at a middle market private equity firm, then took a marketing role in a startup and I'm now in PR. How do I tie together all of those things without making it sound like I'm a job hopper who can't make up her mind? And I guess the other part of it is, if it's an interview, the person has your resume. They can see all these different roles and functions and even industries and certainly organizations. How do you bring together a disjointed story explaining that?

Jim Signorelli: I learned early on that it was really important to do something that you really enjoyed doing for a lot of different reasons, because if your heart's not into it, you're not going to be as good at it as you could be. So I took the liberty of playing discoverer, and I'm really glad I did, because what I ended up with is blah, blah, blah blah blah. This is what I want to do and I am firmly committed to that. There's no question in my mind, based on the experiences I had, make it purposeful, explain the purpose for it, and in fact, it might even turn out to be, and probably should turn out to be an asset in your favor as opposed to a liability.

Anita Brick: And some of that is determined by if you feel comfortable or if you feel embarrassed by it.

Jim Signorelli: Don't think it's a problem because somebody else might think it's a problem. See it as something that really helped you to become the person that you are.

Anita Brick: Got it. So as an executive MBA student, it sounds like the issue here that he's having is that he's telling a story, but people are thinking he wants to do what he used to do. So here's this question. As someone who is seriously investigating embarking on a new career after a lifetime, in my current one, the feedback to my story has been that I seem to be hung up in my current profession.

I try to avoid reciting my resume, and it is a story I've been telling for years, but I seem to leave my audience with the impression that while I want to start on a new path, my story is all about where I've been. How do I convey a desire and an ability to change without disowning my past?

Jim Signorelli: You know, get out of the past real fast, I did this. What I learned is that I am this kind of person. This is what I really believe in. This is what I want to do. And here are the reasons why I want to do what I want to do.

Anita Brick: It's possible that there's also a translation problem if someone talks about their skill set, using the jargon of their current industry. That could also anchor the listener in the past.

Jim Signorelli: Just get out of the past as fast as you can. Explain it as a route to the end goal, as opposed to making it a complete story.

Anita Brick: Okay, so here's a variation of that. As another executive MBA student, I say, many organizations look for experience at the level they're hiring in. If you're trying to take that next step, which is a promotion, how do you overcome the challenge when a potential hiring manager says, we're looking for someone who already has 5 to 10 years of experience at the executive level, meaning you may be one level down from that job.

How do you ensure that you don't get screened out when someone asks you that question? We hear that a lot. You have too much experience. You don't have enough experience yet, but you're looking for a promotion. How do you leverage yourself from the past into a promotional opportunity?

Jim Signorelli: It starts, I think, by understanding the difficulty from your prospective employers position, you need to understand that anybody that person hires has to be justified. And that person was probably given specs. That suggests we're looking for somewhere 5 to 10 years or, you know, something with more experience than you. Ergo, when he goes and says, well, I hired Joe, who's only been doing this for two years, he's going to have some explaining to do.

It starts with understanding and appreciating the perspective of that employer, and then by helping that employer understand that you understand. I know it may be hard to see this on paper, but can I tell you why I would even attempt to apply for this position, knowing full well what you might be up against when asked. When you hire somebody who is allegedly inexperienced, I'd say yeah, tell me.

Tell me your story and then tell a story that indicates something from your experience that taught you what is most important to bring to this particular position. It's a crapshoot. I mean, if this person is very firm and I need somebody for five years and his boss is very firm and his boss's boss's is very firm, you know, you've got an uphill sell.

But I think the best attempt that you can provide is first starting with an understanding of their position, acknowledging your understanding, their position and launching into a story that helps them to see what you want them to see about you.

Anita Brick: Actually, that's quite brilliant because most people make a pitch.

Jim Signorelli: Yep.

Anita Brick: As opposed to showing empathy, to really understand. I think you put it so well. It's not only their decision, but they have to sell it up. The organization, both when they make the hire and if you don't work out, then they've eaten up a whole bunch of social capital that could negatively impact them. So that's a very, very good point to really dig in and think about it from the hiring managers point of view, okay, what could the consequences be of hiring someone that doesn't meet the spec?

Jim Signorelli: Right.

Anita Brick: Really, really. Excellent point. Another executive MBA student said, what's the best way to tell a story? We're on the face of it. What I achieved is commonplace today, but it was actually a big deal for the organization at the time. How can I possibly tell such a story that it's impossible to outline your own contribution without seeming overly arrogant, and to do it in a really concise way?

Jim Signorelli: I love that question. Well, the really big deal is the challenge this person faced in helping this company adopt whatever may be more commonplace in bigger companies. The question that I had to ask myself is, how do I help them to see you know what? In fact, they could do it? That was very different, especially in light of the fact that, you know, this is a I'm making this up, but this is a family owned company, or this is a company that's been doing things the way it's been doing for the last 30 years.

And it's not one that's very open to change as many companies are. And it's understandable. Okay. What I had to do was XYZ. Here's what in fact took place to get to the part about without sounding arrogant, without sounding like you're bragging in corporate. The fact is that once you were able to solicit support from various influencers within the organization, the job became a lot easier because I didn't have to do it myself.

In fact, many of them could do a better job of explaining and helping this change come about than I could. So I enlisted them to do that. That takes off the braggadocio portion of the explanation. Don't think in terms of this is going to make you look bad because you work for a company that was, you know, behind the times. Think about what your challenge was and how you can leverage that challenge to show this prospective employer how you deal with problems.

Anita Brick: Got it. No, that's a very good point. There was a variation of this. Another student asked a question: how should I rebrand myself or tell my story if I was entrenched in a certain career? And then I moved out, it didn't work out and now I have a gap.

Jim Signorelli: Well, in that case, it sound like somebody had to do some rethinking and retooling and really needed some time to take a good look at where they were going and how they were going to get there, so that in fact, they could make the very best decision possible. You know, for better or for worse, I took the time I really needed because it was that important to me to make the right decision. And when I did, I learned the following things about myself and then launched into some of the lessons learned that put me in this seat today.

Anita Brick: Its ownership and its ownership of. Yeah, back to responsibility, back to ownership for that time, and not creating additional obstacles because of the level of discomfort. You know, we've been talking about external obstacles. You know, we have this gap. There was the issue of ethics, someone getting fired because of the big mistake. But there was a question from an alum that was more about internal obstacles. And he said, I have a great story and I'm effective in sharing it with people I know. Yet when I talk to people I don't know, well, I get lost and lose my focus. Any advice?

Jim Signorelli: Well, a couple of things. One is to think of a story as a character overcoming an obstacle to achieve some goal. Just have that structure in your mind when you're developing the story, and then, you know, there are different ways to recall what you're going to say without getting lost. I typically rely on pictures. In my mind, I kind of put myself right back to where it was and I see it, you know, I feel it, I sense it, I smell it.

The more I'm back there, the better and the more passion I can put into my story and the more real I can make it. Too often we're thinking about the performance and not thinking enough about the content and the meaning that we're trying to convey. If it gets stuck on performance, authenticity is going to be lost. And that's the most important thing in storytelling. I think I should say the most. It's right up there.

Anita Brick: Oh yeah.

Jim Signorelli: People know right away when you're putting on an act or over rehearsed, or you're saying you're just going through the motions, they want to feel this is real.

Anita Brick: If you don't, then what else are you misleading them with?

Jim Signorelli: Right. Exactly.

Anita Brick: One of the things that you talk a lot about in the book, it was great. This is really toward the, I don't know, the last quarter of the book, you talked about how, yes, you need to know yourself and I think you've been talking about that. You need to know what you bring. Have real examples. Know why.

No, you know what you believe in your values and all of that. But you also need to know the other person. And you talked about two things that you can do, and maybe you can expound on it a little bit more, because ultimately you want to have empathy and you stand in the book. You said that there are two activities: observation and immersion. What is observation and immersion, and how could that translate into telling a career story.

Jim Signorelli: By observation, what we mean is the research that you can do on the company, everything from what's there that's already published, their website, their materials, what people say about them. Thoroughly investigate whatever you can to observe what kind of company this is. The observed piece is really the outer layer. What's this company doing? And you know, how does it want to be known?

And there's all sorts I wish, you know, 20 years ago when I was looking for work, that there were things like LinkedIn and the internet just in general, because there's just an amazing amount of information, plus the employer expects that of you employer, really I do, I do whenever I'm interviewing somebody, the worst thing you could do is tell me that, you know, give me the perfunctory explanation of what my company is about that anybody else could give me by just looking at the landing page of my website.

I really want to know, you know, what we are about. Okay. That is observation. Immersion is it's really walking in the company's shoes. Now, how do you do that? Because you have never been there and you only know it from hearsay and what you've read and you know what you say. Well, what we do is we use this thing we call an I am statement and I am statement is like a one page manifesto, if you will, of the company based on your assumptions.

It can only be based on your assumptions. But I am Procter and Gamble and I am very rigorous in terms of the way I approach the market. And I believe that the customer must come first. And I believe this, and I value this, and my people are all this way, and these are the kinds of people that we look for to work here.

And here are the reasons why. And it's really trying to, as much as you possibly can, based on your observation, immerse yourself in terms of who they are, how they think, what they value and what they believe, and to write it down. And just the process of writing it down is important, because when you do, you'll often come up with information, needs or assumptions that need to be better investigated.

In fact, I think that's one of the biggest advantages of doing this, because it forces you to take a good, hard look at the assumptions you're making and to question whether, in fact, that you really should make those assumptions. We do that for our clients when we go to pitch an account or when we go to talk to somebody we haven't talked to before, you know, we write out this I am statement trying to empathize as much as possible.

Now we could find out we're wrong. We don't go in with a definite yep, I know who they are, but we do go in with some theories and some hypotheses and those could all be blown away the first time we say Kansas, somebody in the company. But at least we go in with some idea of what this person might be looking for and where that person might be coming from and what is important to them based on the experience we bring to that meeting, as well as what we've learned and observed about that particular company. So that's your question.

Anita Brick: Yeah, I think so, because what it's saying to me, and please correct me if this is wrong, the observation part is the research students and alumni at Booz have lots of different tools.

Jim Signorelli: Resources, right?

Anita Brick: You place things like one source where you get a bunch of aggregated data analysts reports to, like you said, LinkedIn, go talk to someone. That's part of their research too. But in some ways, it allows you to take it further than just what you read. It does help you have more empathy. There was a student. We were doing a focus group after our recruiting cycle, and one of the students said, and I think that this whole process would have helped him.

He said that he made a mistake, and usually people don't say they made a mistake in front of their, you know, their classmates and stuff like that. And so we all turned to look at him and say, well, what do you mean? He said, although he found a position that he liked, he felt like he could have landed something even better had he been genuinely interested and showed greater empathy for the people with whom he was networking, people where he had interviews.

And he said, I mean, use your words. But he said if he had done a little bit more research, he could have shown how he was genuinely interested and he probably would have developed a deeper relationship and gotten a lot farther. You're asking the person, you're asking someone who is going to have that networking call or that interview to write a story from the company's point of view or the hiring manager's point of view. And they could be right. They could be wrong. But the fact that they've taken the time, it feels like they're going to have an edge over people who don't.

Jim Signorelli: Exactly. And I want to add something to what I said. And reinforce what you just said. Think of the observation piece as what about this company? And think of the immersion piece as the why. Every company has a why. It may be amorphous, it may not be who all stated it. It may be fractionalized in that there are some people who think this is the reason why we exist versus another group that thinks something differently, but what you're really trying to do is use those facts in the what, to surmise the why, and to help you to understand why this company does what it does, why this company acts the way it does

to get to their motivation, to get to their beliefs, to their values. And for sure, if you're not able to get to all of that, you never will be, but you'll at least have a starting point. What you don't know would make for some interesting questions in the interview itself. I just was wondering, you do this and that and you really put an emphasis on x, y, z. And I'd like to hear more about how you came to decide that that was so important. That would be a great question.

Anita Brick: Sometimes it's really hard to come up with questions that you really want to know the answers to in an interview if you've done a lot of research, but that gives us another way to channel it.

Jim Signorelli: I love the question. I don't like questions like this. Where do you expect the company to be in five years? Who do you consider your major competitors? I mean, these are perfunctory. These are questions anybody could ask. I want my questions.

Anita Brick: Yeah. I mean, and they create dialog too. Do you have time for one more question?

Jim Signorelli: I do, I do, I love this think back.

Anita Brick: Think ahead. If you were advising someone who's sitting right in front of you, what are the top three things that you would tell someone who wants to develop and share a really compelling career story?

Jim Signorelli: Do I only get three? maybe I could do four that come to mind. One I use the past is Prolog without, you know, again, getting too lost in the past. But what you've learned about yourself, not just about how to do things, but what you've learned about yourself as a person because you are being hired more for who you are than what you do.

Once you make the interview and you know the short list, everybody there has a resumé that probably is not much more detailed than yours in terms of experience, because you've qualified to the point you know where you're now a candidate with knowledge of who is going to be important. So use that past as a Prolog to who you are.

I'd say to you know, be somewhat self-deprecating in telling the story. Don't always sound like you have to be perfect. Don't take yourself too seriously. So your sense of humor, the only thing true we didn't talk about it is use metaphors. Metaphors are short stories. You said something like, I felt like I was in a car race with the brakes on.

I just told you a story. You can't steal second base while keeping your foot on first. I just told this story in a very short way to get to the point and to make it memorable. Without getting into though, once upon a time there was a beginning, middle and end and the fourth would be. Or did I do 3 or 4?

Because I wanted to add this is to find out what their story is and relate to their story, and listen very carefully to what their story is and know how to ask what their story is. You know, one of the things that I do, like, when people come in an interview is they say, boy, the storytelling that you guys do, you know, how did you get started with that?

Probably can't tell. But I do like to talk. And, everybody does like to talk about themselves. Give them a chance to tell their story and pick up on what's important to that person through their story. It's as important to understand how to listen to stories as it is to learn how to tell them.

Anita Brick: That's great. You know, you've told us and taught us a whole lot in the time that we've had together. So thank you very, very much. And thank you for creating this really strong, powerful framework in story branding. And I know it applies to products and brands. It certainly applies to each of us as we go through our own careers. Thank you for creating a framework that is so relevant.

Jim Signorelli: Well thank you, I really appreciate it. And it was fun.

Anita Brick: Good good good. Well thanks again and thank you all for listening. This is Anita Brick with CareerCast at Chicago Booth. Keep advancing.

Anita Brick: Hi, this is Anita Brick and welcome to CareerCast at Chicago Booth. To help you advance in your career. Today, we're delighted to be speaking with Jim Signorelli, who is an advertising executive. And his career has been spent at major national advertising agencies. His clients have included Citibank, GE, Toshiba, Burger King, International Harvester and many, many more. Jim is the co-founder and CEO of Story Lab.

Crane Chicago Business has cited his firm as one of the top 25 agencies in Chicago, and it's been named to the Inc 5000 list for the last three years. Jim, thank you so much for making the time. I know you're super busy, and also thank you for writing a wonderful book, story branding.

Jim Signorelli: And I'm very excited to be here.

Anita Brick: And you know, when you think about story branding, if we can't do it for ourselves, we can't really survive in the world today. So just to get us started. What do you consider to be key building blocks for a compelling career story?

Jim Signorelli: Can I back up just a little bit and explain the basis for why stories in the context of seeking employment amassed a lot? Why stories? What's so great about stories and the scientific answer to that? Psychologists are proving our brains are really hardwired to think in terms of stories. They help us to process information better than perhaps any form of communication outside of that.

Anybody who's ever told a story and that's just about everybody here, would readily agree with the fact that stories are engaging. They help us to relate or empathize with the storyteller. But the biggest, best reason for using stories in any persuasive communication comes from a quote I wish I had written as it really sums up something I strongly believe in and underscores the biggest benefit of story.

Storytelling reveals meaning without committing the error of defining it. And it was by Hannah Arendt is a political philosopher, you know, and it's something we tell our clients all the time. It's one thing to tell people who you are, or to find for them how they should position you or think about you in their minds. Yet it's quite another to get them to position you the way you want them to do, by their own volition.

Another way of saying the simple way to lead them to water. But don't make them drink. Give them enough incentive to want to drink and get involved. And that's what stories really help do. So to more specifically answer your question, consider the key building blocks of a compelling career transition story, first and foremost, knowing why that transition was made and really doing the proper introspection to get at the reason why, and then to construct that in terms of a story.

I made a career transition. It was in promotion or function of marketing, just as advertising. I was with an agency that specializes in promotion. Here's the story. One day, while I was working on a project, it occurred to me that we were really missing some strategic opportunities, and for my employer, who ended up hiring me, I listed those off.

Got him to agree that, yes, those were some important issues. And I concluded by saying, you know, despite this, I wasn't able to do much about it. And I told my interviewers that I wanted to be at the forefront of the strategy. And I felt that promotion was more executional or tactical. And I'm glad I did get a taste of promotion because it helped me to understand its importance more than I could have otherwise.

But I did find out myself that I have this proclivity for analytics and the reasons why a given strategy was being used, as opposed to being handed a strategy to execute. That did me good, and I think it worked a lot better than had I said, well, I decided that I really wanted to do something different that was more in line with my skills and my talents.

I zeroed in on a particular instance that helped me to realize what the problem was, and I talked about, you know, the outcome of that realization. And ultimately why I made the change I did. The derailing comes from telling people and not showing them, not demonstrating.

Anita Brick: It sounds like what you did was you knew the why, but then you gave almost like a little glimpse into that pivotal point for you, where you allowed them to see from your point of view. Yes, it's relevant to them. An example of how you came to that realization, but also what it could do. So it was the why, but then also a real life example, a mini one. It was a good one. In addition to those, are there other things that need to be in a compelling story?

Jim Signorelli: Think about what a story is and there's lots of different definitions for it. But the one I come back to is a story. Is a character overcoming an obstacle to achieve some goal. Probably the most important component of the story is the obstacle itself. A story is in the story without a conflict, without something that has to be thought through, without there being a problem that has to be solved.

That's what makes stories a story. You know, when you're thinking about how to communicate your why, as I did in this case, think about the obstacle that you're trying to overcome. That's probably one of the most important things to do, because otherwise you're just telling it. Without that definition of the obstacle or the problem that you're trying to solve, you're just telling people by involving people in the conflict and explaining to them why you saw it as a conflict. You do a lot of things. You tell them how you think. You tell them the kind of person you are. You tell them what you value, and you do that without telling them. Yeah, I think that's key.

Anita Brick: Okay. So you talked about obstacles. I think some of the questions ahead of time, it seemed like most of the questions were around some obstacle then having to create a story that went beyond the obstacle. First of all, someone said, I've spent the last four years at home taking care of my kids while my wife established her legal practice. How do I create a solid story so that I don't appear stale?

Jim Signorelli: I would redefine the obstacle. The obstacle is, in this case, has to do with something that costs you to take time off. You know, I had a personal interview not too long ago. He had the same thing. He had a year and a half missing from his resume. When I asked him about that, he told me a story about his son who contracted stomach cancer and how he felt that he was, you know, in the horns of a dilemma and had to make a tough decision about what really was important.

And I decided, he said that, you know, I needed to be with my son at whatever cost. And yes, you know, 18 months missing from my resume will probably be the most important 18 months of my life. And I was blown away. Am I okay? You answered that very well, told me a lot about himself without telling me or explaining the rationale, and was really presented in the form of a story about his relationship with his son.

Anita Brick: Well, it's interesting because there was a question from a weekend student, it fits in really well here. It says, when is a story too personal for a business situation? So clearly you didn't think that this father talking about his son having a really serious illness was too personal? When is a personal story too personal to tell?

Jim Signorelli: Big one's a business, a religion, politics and sexual preference. So like everything else, I would tell anybody he was looking for a job. You're going to be hired not just for your skills, but you're going to be hired for your beliefs, your values, the kind of person you are. And you should feel free to expose yourself so that whoever you're talking to gets an accurate impression of the kind of person you are.

You have to use your discretion. Stay on the safer side, but at the same time, don't be so safe that you stick to facts only and avoid any personal stories to the point where you sound like just about everybody else is in there. Reveal your personality. Reveal who you are as a person. There's more risk in not doing that.

Anita Brick: Okay. Fair enough. So that alarm had a question, another dilemma, another obstacle. He said. I was fired from my firm after making a mistake that cost millions of dollars. I work in a fairly niche industry in which word spreads quickly. Given the enormity of the loss and the bad blood that now exists between me and my former employer, I feel like I'm walking around with a scarlet letter on my chest. How do you tell a compelling story? If a significant black mark is front and center on your record?

Jim Signorelli: That's a challenging question. I won't deny that. I would suggest, without knowing the specifics, that the story might be about what happened, of course, and what was learned as a result of what happened. I don't think you have to wear a hair shirt and tell everybody, I'm going to spend the rest of my life dealing with heavy guilt, but I think you need to be realistic, and you need to be straightforward, and you need to admit to whatever happened in a positive way, as you possibly can, with the understanding that you really learn something from it.

If there's a way to demonstrate that you've learned from it. The second time something occurred where this could have happened, all the better. But you know, if you're concerned about wearing a scarlet letter prior to and during the interview, unless it comes out, you will be trying to hide something the whole time you're employed. And that could be very stressful.

You know, you're always wondering when you're going to be found out. Better to face the facts and to tell the story in the most positive light you possibly can without casting blame or without sounding like you're not taking responsibility, but nevertheless come forward and be forthcoming.

Anita Brick: It's going to raise some kind of red flag anyway. We kind of know that.

Jim Signorelli: Think about it this way. I doubt if the first question you're going to be asked in an interview is, I understand you made a $1 million mistake. Tell me about that. Probably the first question you're going to be asked is tell me about yourself. You are going to be given plenty of opportunity to win the win over whoever you're talking to, with your stories about who you are, how you think, what you believe, what you value, and win that person over to your side such that they will be in a position to better understand the problem, empathize with you, and maybe even support you or your reasons why for it occurring.

Anita Brick: Absolutely. And then definitely be prepared for what's your reason for leaving. That undoubtedly is a question that virtually everyone is going to be asked. You know, there was another question, this time from an evening student. I recently left a company because they were doing things I thought were unethical. There were other reasons as well, namely general bad management. How do I tell this story? My biggest concern is sounding like I'm badmouthing a former employer, and I know that that is a disaster.

Jim Signorelli: Well, it is, and less trust has already been established. And in an interview situation, there's still a lot of not distrust but skepticism. So you don't want to bad mouth somebody right off the bat, you really don't want to bad mouth anybody. Anyway, I think the best way to go about doing that is to answer the question in a roundabout way with something like, well, let me tell you a little bit about myself and the kinds of things that I believe in.

Then express something that you've learned. I firmly believe in that. And I am pretty much dedicated to that and will be wherever I go. I think it's important for you to know that about me. If probing persists and the interviewer says, well, wait a minute, I understand that there was a problem with honesty, you know? Or tell me a little more about that. Turn the table. You'll get a lot more credit for that. You'll be seen as somebody who's very diplomatic, who knows how to handle a difficult situation.

Anita Brick: I would agree with you. I think that's in part a way of answering that question without saying anything bad. What I came to realize is that the values of the organization were just different from mine.

Jim Signorelli: Could just come right out and say that.

Anita Brick: You said it's all about taking responsibilities. People feel very uncomfortable when we say anything bad about a former colleague, a former employer. You and I both said it's treading lightly in this area and taking responsibility and then moving through it in a way that answers the question without derailing the whole interview.

Jim Signorelli: What's most important in an interview session is to help the interviewer understand how you think you will be judged in terms of how you dealt with it. Awkward situation, how you dealt with a difficult question.

Anita Brick: You know there was one other, one other obstacle question. A weekend student said my career progression to date has been fairly disjointed. I started as a news reporter, moved to recruiting at a middle market private equity firm, then took a marketing role in a startup and I'm now in PR. How do I tie together all of those things without making it sound like I'm a job hopper who can't make up her mind? And I guess the other part of it is, if it's an interview, the person has your resume. They can see all these different roles and functions and even industries and certainly organizations. How do you bring together a disjointed story explaining that?

Jim Signorelli: I learned early on that it was really important to do something that you really enjoyed doing for a lot of different reasons, because if your heart's not into it, you're not going to be as good at it as you could be. So I took the liberty of playing discoverer, and I'm really glad I did, because what I ended up with is blah, blah, blah blah blah. This is what I want to do and I am firmly committed to that. There's no question in my mind, based on the experiences I had, make it purposeful, explain the purpose for it, and in fact, it might even turn out to be, and probably should turn out to be an asset in your favor as opposed to a liability.

Anita Brick: And some of that is determined by if you feel comfortable or if you feel embarrassed by it.

Jim Signorelli: Don't think it's a problem because somebody else might think it's a problem. See it as something that really helped you to become the person that you are.

Anita Brick: Got it. So as an executive MBA student, it sounds like the issue here that he's having is that he's telling a story, but people are thinking he wants to do what he used to do. So here's this question. As someone who is seriously investigating embarking on a new career after a lifetime, in my current one, the feedback to my story has been that I seem to be hung up in my current profession.

I try to avoid reciting my resume, and it is a story I've been telling for years, but I seem to leave my audience with the impression that while I want to start on a new path, my story is all about where I've been. How do I convey a desire and an ability to change without disowning my past?

Jim Signorelli: You know, get out of the past real fast, I did this. What I learned is that I am this kind of person. This is what I really believe in. This is what I want to do. And here are the reasons why I want to do what I want to do.

Anita Brick: It's possible that there's also a translation problem if someone talks about their skill set, using the jargon of their current industry. That could also anchor the listener in the past.

Jim Signorelli: Just get out of the past as fast as you can. Explain it as a route to the end goal, as opposed to making it a complete story.

Anita Brick: Okay, so here's a variation of that. As another executive MBA student, I say, many organizations look for experience at the level they're hiring in. If you're trying to take that next step, which is a promotion, how do you overcome the challenge when a potential hiring manager says, we're looking for someone who already has 5 to 10 years of experience at the executive level, meaning you may be one level down from that job.

How do you ensure that you don't get screened out when someone asks you that question? We hear that a lot. You have too much experience. You don't have enough experience yet, but you're looking for a promotion. How do you leverage yourself from the past into a promotional opportunity?

Jim Signorelli: It starts, I think, by understanding the difficulty from your prospective employers position, you need to understand that anybody that person hires has to be justified. And that person was probably given specs. That suggests we're looking for somewhere 5 to 10 years or, you know, something with more experience than you. Ergo, when he goes and says, well, I hired Joe, who's only been doing this for two years, he's going to have some explaining to do.

It starts with understanding and appreciating the perspective of that employer, and then by helping that employer understand that you understand. I know it may be hard to see this on paper, but can I tell you why I would even attempt to apply for this position, knowing full well what you might be up against when asked. When you hire somebody who is allegedly inexperienced, I'd say yeah, tell me.

Tell me your story and then tell a story that indicates something from your experience that taught you what is most important to bring to this particular position. It's a crapshoot. I mean, if this person is very firm and I need somebody for five years and his boss is very firm and his boss's boss's is very firm, you know, you've got an uphill sell.

But I think the best attempt that you can provide is first starting with an understanding of their position, acknowledging your understanding, their position and launching into a story that helps them to see what you want them to see about you.

Anita Brick: Actually, that's quite brilliant because most people make a pitch.

Jim Signorelli: Yep.

Anita Brick: As opposed to showing empathy, to really understand. I think you put it so well. It's not only their decision, but they have to sell it up. The organization, both when they make the hire and if you don't work out, then they've eaten up a whole bunch of social capital that could negatively impact them. So that's a very, very good point to really dig in and think about it from the hiring managers point of view, okay, what could the consequences be of hiring someone that doesn't meet the spec?

Jim Signorelli: Right.

Anita Brick: Really, really. Excellent point. Another executive MBA student said, what's the best way to tell a story? We're on the face of it. What I achieved is commonplace today, but it was actually a big deal for the organization at the time. How can I possibly tell such a story that it's impossible to outline your own contribution without seeming overly arrogant, and to do it in a really concise way?

Jim Signorelli: I love that question. Well, the really big deal is the challenge this person faced in helping this company adopt whatever may be more commonplace in bigger companies. The question that I had to ask myself is, how do I help them to see you know what? In fact, they could do it? That was very different, especially in light of the fact that, you know, this is a I'm making this up, but this is a family owned company, or this is a company that's been doing things the way it's been doing for the last 30 years.

And it's not one that's very open to change as many companies are. And it's understandable. Okay. What I had to do was XYZ. Here's what in fact took place to get to the part about without sounding arrogant, without sounding like you're bragging in corporate. The fact is that once you were able to solicit support from various influencers within the organization, the job became a lot easier because I didn't have to do it myself.

In fact, many of them could do a better job of explaining and helping this change come about than I could. So I enlisted them to do that. That takes off the braggadocio portion of the explanation. Don't think in terms of this is going to make you look bad because you work for a company that was, you know, behind the times. Think about what your challenge was and how you can leverage that challenge to show this prospective employer how you deal with problems.

Anita Brick: Got it. No, that's a very good point. There was a variation of this. Another student asked a question: how should I rebrand myself or tell my story if I was entrenched in a certain career? And then I moved out, it didn't work out and now I have a gap.

Jim Signorelli: Well, in that case, it sound like somebody had to do some rethinking and retooling and really needed some time to take a good look at where they were going and how they were going to get there, so that in fact, they could make the very best decision possible. You know, for better or for worse, I took the time I really needed because it was that important to me to make the right decision. And when I did, I learned the following things about myself and then launched into some of the lessons learned that put me in this seat today.

Anita Brick: Its ownership and its ownership of. Yeah, back to responsibility, back to ownership for that time, and not creating additional obstacles because of the level of discomfort. You know, we've been talking about external obstacles. You know, we have this gap. There was the issue of ethics, someone getting fired because of the big mistake. But there was a question from an alum that was more about internal obstacles. And he said, I have a great story and I'm effective in sharing it with people I know. Yet when I talk to people I don't know, well, I get lost and lose my focus. Any advice?

Jim Signorelli: Well, a couple of things. One is to think of a story as a character overcoming an obstacle to achieve some goal. Just have that structure in your mind when you're developing the story, and then, you know, there are different ways to recall what you're going to say without getting lost. I typically rely on pictures. In my mind, I kind of put myself right back to where it was and I see it, you know, I feel it, I sense it, I smell it.

The more I'm back there, the better and the more passion I can put into my story and the more real I can make it. Too often we're thinking about the performance and not thinking enough about the content and the meaning that we're trying to convey. If it gets stuck on performance, authenticity is going to be lost. And that's the most important thing in storytelling. I think I should say the most. It's right up there.

Anita Brick: Oh yeah.

Jim Signorelli: People know right away when you're putting on an act or over rehearsed, or you're saying you're just going through the motions, they want to feel this is real.

Anita Brick: If you don't, then what else are you misleading them with?

Jim Signorelli: Right. Exactly.

Anita Brick: One of the things that you talk a lot about in the book, it was great. This is really toward the, I don't know, the last quarter of the book, you talked about how, yes, you need to know yourself and I think you've been talking about that. You need to know what you bring. Have real examples. Know why.

No, you know what you believe in your values and all of that. But you also need to know the other person. And you talked about two things that you can do, and maybe you can expound on it a little bit more, because ultimately you want to have empathy and you stand in the book. You said that there are two activities: observation and immersion. What is observation and immersion, and how could that translate into telling a career story.

Jim Signorelli: By observation, what we mean is the research that you can do on the company, everything from what's there that's already published, their website, their materials, what people say about them. Thoroughly investigate whatever you can to observe what kind of company this is. The observed piece is really the outer layer. What's this company doing? And you know, how does it want to be known?

And there's all sorts I wish, you know, 20 years ago when I was looking for work, that there were things like LinkedIn and the internet just in general, because there's just an amazing amount of information, plus the employer expects that of you employer, really I do, I do whenever I'm interviewing somebody, the worst thing you could do is tell me that, you know, give me the perfunctory explanation of what my company is about that anybody else could give me by just looking at the landing page of my website.

I really want to know, you know, what we are about. Okay. That is observation. Immersion is it's really walking in the company's shoes. Now, how do you do that? Because you have never been there and you only know it from hearsay and what you've read and you know what you say. Well, what we do is we use this thing we call an I am statement and I am statement is like a one page manifesto, if you will, of the company based on your assumptions.

It can only be based on your assumptions. But I am Procter and Gamble and I am very rigorous in terms of the way I approach the market. And I believe that the customer must come first. And I believe this, and I value this, and my people are all this way, and these are the kinds of people that we look for to work here.

And here are the reasons why. And it's really trying to, as much as you possibly can, based on your observation, immerse yourself in terms of who they are, how they think, what they value and what they believe, and to write it down. And just the process of writing it down is important, because when you do, you'll often come up with information, needs or assumptions that need to be better investigated.

In fact, I think that's one of the biggest advantages of doing this, because it forces you to take a good, hard look at the assumptions you're making and to question whether, in fact, that you really should make those assumptions. We do that for our clients when we go to pitch an account or when we go to talk to somebody we haven't talked to before, you know, we write out this I am statement trying to empathize as much as possible.

Now we could find out we're wrong. We don't go in with a definite yep, I know who they are, but we do go in with some theories and some hypotheses and those could all be blown away the first time we say Kansas, somebody in the company. But at least we go in with some idea of what this person might be looking for and where that person might be coming from and what is important to them based on the experience we bring to that meeting, as well as what we've learned and observed about that particular company. So that's your question.

Anita Brick: Yeah, I think so, because what it's saying to me, and please correct me if this is wrong, the observation part is the research students and alumni at Booz have lots of different tools.

Jim Signorelli: Resources, right?

Anita Brick: You place things like one source where you get a bunch of aggregated data analysts reports to, like you said, LinkedIn, go talk to someone. That's part of their research too. But in some ways, it allows you to take it further than just what you read. It does help you have more empathy. There was a student. We were doing a focus group after our recruiting cycle, and one of the students said, and I think that this whole process would have helped him.

He said that he made a mistake, and usually people don't say they made a mistake in front of their, you know, their classmates and stuff like that. And so we all turned to look at him and say, well, what do you mean? He said, although he found a position that he liked, he felt like he could have landed something even better had he been genuinely interested and showed greater empathy for the people with whom he was networking, people where he had interviews.

And he said, I mean, use your words. But he said if he had done a little bit more research, he could have shown how he was genuinely interested and he probably would have developed a deeper relationship and gotten a lot farther. You're asking the person, you're asking someone who is going to have that networking call or that interview to write a story from the company's point of view or the hiring manager's point of view. And they could be right. They could be wrong. But the fact that they've taken the time, it feels like they're going to have an edge over people who don't.

Jim Signorelli: Exactly. And I want to add something to what I said. And reinforce what you just said. Think of the observation piece as what about this company? And think of the immersion piece as the why. Every company has a why. It may be amorphous, it may not be who all stated it. It may be fractionalized in that there are some people who think this is the reason why we exist versus another group that thinks something differently, but what you're really trying to do is use those facts in the what, to surmise the why, and to help you to understand why this company does what it does, why this company acts the way it does

to get to their motivation, to get to their beliefs, to their values. And for sure, if you're not able to get to all of that, you never will be, but you'll at least have a starting point. What you don't know would make for some interesting questions in the interview itself. I just was wondering, you do this and that and you really put an emphasis on x, y, z. And I'd like to hear more about how you came to decide that that was so important. That would be a great question.

Anita Brick: Sometimes it's really hard to come up with questions that you really want to know the answers to in an interview if you've done a lot of research, but that gives us another way to channel it.

Jim Signorelli: I love the question. I don't like questions like this. Where do you expect the company to be in five years? Who do you consider your major competitors? I mean, these are perfunctory. These are questions anybody could ask. I want my questions.

Anita Brick: Yeah. I mean, and they create dialog too. Do you have time for one more question?

Jim Signorelli: I do, I do, I love this think back.

Anita Brick: Think ahead. If you were advising someone who's sitting right in front of you, what are the top three things that you would tell someone who wants to develop and share a really compelling career story?

Jim Signorelli: Do I only get three? maybe I could do four that come to mind. One I use the past is Prolog without, you know, again, getting too lost in the past. But what you've learned about yourself, not just about how to do things, but what you've learned about yourself as a person because you are being hired more for who you are than what you do.

Once you make the interview and you know the short list, everybody there has a resumé that probably is not much more detailed than yours in terms of experience, because you've qualified to the point you know where you're now a candidate with knowledge of who is going to be important. So use that past as a Prolog to who you are.

I'd say to you know, be somewhat self-deprecating in telling the story. Don't always sound like you have to be perfect. Don't take yourself too seriously. So your sense of humor, the only thing true we didn't talk about it is use metaphors. Metaphors are short stories. You said something like, I felt like I was in a car race with the brakes on.

I just told you a story. You can't steal second base while keeping your foot on first. I just told this story in a very short way to get to the point and to make it memorable. Without getting into though, once upon a time there was a beginning, middle and end and the fourth would be. Or did I do 3 or 4?

Because I wanted to add this is to find out what their story is and relate to their story, and listen very carefully to what their story is and know how to ask what their story is. You know, one of the things that I do, like, when people come in an interview is they say, boy, the storytelling that you guys do, you know, how did you get started with that?

Probably can't tell. But I do like to talk. And, everybody does like to talk about themselves. Give them a chance to tell their story and pick up on what's important to that person through their story. It's as important to understand how to listen to stories as it is to learn how to tell them.

Anita Brick: That's great. You know, you've told us and taught us a whole lot in the time that we've had together. So thank you very, very much. And thank you for creating this really strong, powerful framework in story branding. And I know it applies to products and brands. It certainly applies to each of us as we go through our own careers. Thank you for creating a framework that is so relevant.

Jim Signorelli: Well thank you, I really appreciate it. And it was fun.

Anita Brick: Good good good. Well thanks again and thank you all for listening. This is Anita Brick with CareerCast at Chicago Booth. Keep advancing.