Career Strategies for the AI Era

On this episode of Digital Squared, Tom is talking to Jeremy Schifeling, founder of The Job Insiders, which provides career technology training for hundreds of top universities and business schools around the world. He started his career as a kindergarten teacher but found his true calling in technology and innovation, where he went to work at companies like LinkedIn, Google and Khan Academy before venturing out on his own as a career coach and entrepreneur. 

His passion and focus is on helping people tap into the power of LinkedIn and ChatGPT, which he’s written about in several best-selling books. You can check out his latest career and AI hacks on LinkedIn. 

Transcript

Speaker 1  0:00  
Welcome to Digital squared, a podcast that explores the implications of living in an increasingly digital world. We're on a mission to inspire our listeners to use technology and data for good. Your host, Tom Andriola is the Vice Chancellor for Information Technology and data and Chief Digital Officer at the University of California at Irvine, join us as Tom and fellow leaders discuss the technological, cultural and societal trends that are shaping our world. On

Tom  0:29  
this episode, I'm talking to Jeremy Schifeling. Jeremy is the founder of the job insiders, which provides career technology training for hundreds of top universities and business schools around the world. Jeremy has a cool story. He started his career as a kindergarten teacher, but found his true calling in technology and innovation, going to work at companies like LinkedIn, Google and Khan Academy, before venturing out on his own as a career coach and entrepreneur. His passion is on helping people tap into the power of LinkedIn and chatGPT, which he has written several best-selling books about, and is an avid content creator. You should check him out and his latest career AI hacks on LinkedIn. Jeremy, welcome to the podcast. 

Jeremy 1:14
Hey. Thanks so much for having me here. 

Tom 1:16
Thanks for being with us now your story. I love your story and your progression. I know you're gonna take us through the story, but I'd also like you to talk about where this entrepreneurial bent that you have to your career progression came from.

Jeremy  1:29  
Yeah, so it's interesting, because I was thinking back about where did I get this spark, where did this Genesis of desire to create things come from? And I realized it didn't necessarily come from a college class or a specific teacher. It came from the experience of being a kid in Buffalo, New York who just wanted to do something in the world. I remember having a paper route, and then deciding, hey, what if I got together with the other paper boys and started a paper boys union, and we did that. And then I decided, hey, what if I started my own website? Maybe I can do that. And I think that the real thing that gets me excited about Gen AI and all the technologies we're going to talk about today is for that next kid growing up, whether they're in Irvine or Buffalo or Mumbai, the real the sky really is the limit in terms of what could they build with their hands today that wouldn't have been even imaginable 20 years ago. 

Tom  2:15  
Where did the decision to go into teaching come from? Right? Because then you made this incredible pivot that we'll talk about. But where did the path lead you to become a teacher earlier in your career?

Jeremy  2:25  
Yeah, great question. So I think again, comes back from that real deep passion to do something in the world. I was going to a small liberal arts college, and it was very academic, very ivory tower, and education was the one chance to get out of that tower and go out into the world and do something, do something for someone else. And what I ultimately figured out is that teaching wasn't the right thing for me, but that hunger was still very much there where I wanted to serve others, I wanted to leave that little dent in the universe that Steve Jobs talks about. And for me, having a chance to get access to that was the greatest gift I've had in my life. 

Tom  2:59  
Today, as you think about what you're doing, are there times when you reflect back to things that happen in the classroom that you're like, this is some of what's shaped me or shaped the way I think about situations or what's possible. I always find like, there are those moments in those experiences that define how you look at the world going forward. What are some of those for you? 

Jeremy  3:17  
It's so true. I feel like everything that we've lived through becomes a lens for what we're about to live through next. And it was funny giving these presentations here at Irvine today, as I stood on that stage, I reflected back on being on the classroom 20 years ago and all the things I learned the hard way about the fact that it wasn't enough just to get up and talk and have people listen, you had to earn their attention, even at five years old, especially at five years old. And so in the same way that I tried to really engage people on the faculty and the staff, it was all these things that I had experienced firsthand as a kindergarten teacher and then informed the way I do things today.

Tom  3:52  
I would say the average adult probably has the attention span of a kindergartener thanks to our mobile phones and social media. Okay, so you go from the classroom, you go through this journey. I want you to talk about each of the steps, and now talk about this amazing thing that you're doing now, which is really cold. And for our audience, we had Jeremy on campus today with us talking to several groups, but just take us through that journey. 

Speaker 3  4:16  
Yeah. So I think after I left the classroom, and I want to really call this out, like I was a terrible kindergarten teacher. I was the worst. My penmanship was bad. The kids were barely learning to read. And the reality is that learning what you're not good at can often open as many doors as learning what you are good at, because you say, Hey, I'm not going to focus on this path that's not right for me. I'm going to choose something that is true to who I am. And I realized that when I was working on the classroom blog, when I was helping the kids record MP3s. That's when I was in my flow moment, and I said, How can I get back to that? How can I do more of that? And that same passion for using technology to build things led me to work for nonprofits like Teach for America and Echoing Green, which was a seed funder of early startups in the nonprofit space. And then ultimately. When I ultimately graduated from business school and went out into the world, even though I worked for some big companies for a while, for LinkedIn, for Google, what really got me excited was, could I take everything I learned teaching in kindergarten, everything I learned working in the nonprofit sector, and just do it bigger, not just reach 10 kids or 100 kids or 1000 people, but hundreds of 1000s of people on the most important things to them, which are living a great life, having great access to a great career. And that's why I ultimately founded this organization, the job insiders to really try to scale up that impact. So the biggest career secrets aren't kept inside of business school. They're there for everyone to benefit from.

Tom  5:36  
Yeah, I want to go back to one thing you said, which is that you weren't the best teacher. I find so many people today, they worry about making that bad career decision, right? Taking a job that doesn't work out, but you talked about it yourself. It's part of your story. It's part of your journey. Sometimes the most important lessons are what we don't like or what we're not good at, because they open other doors. How do you explain that to people? And do you find that you have a way of bringing it across that people really respond to? Because there's a lot of people who are afraid to make that mistake.

Jeremy  6:05  
Absolutely and I feel like, especially if you're 18 years old today, and you've been sitting in this social media saturated environment for the last decade of your life, every signal you're getting from society is that you have to be clear about what you want. You have to pursue the same path that all your friends are going after. You have to go work for some big corporation, and that anything that deviates from that is dangerous and risky. And I get it. We've just lived through the Great Recession, the pandemic, all these different things that have us fleeing to safety. But at the same time, when you look back on any great career, it's never just a linear path up. It's always this roller coaster of trying this, failing at that, learning from that. And I think if you start to realize that there's any kind of pattern across the human experience, is that the diversity of experience, and even the diversity of success and failure, is the best predictor of future success, versus just I knew it all at 18. 

Tom  6:54  
Absolutely, it's one of the reasons I try to get young people. I learned it as the informational interview, right? How to look at someone who says, I love to understand how they got there, invite them to a cup of coffee, ask them questions. And what I found is that when you do that, people will tell you about their missteps. And it's always, always made me feel better, because it's that I think, where I learned I don't have to be perfect. Not every role is going to work out the way I thought it was going back. They usually don't work out right. It's like, you think it's going to be this and it ends up being something different and but you have to hear that it's okay to take missteps and sidesteps and double steps and all of that. Jeremy, where you and I are talking here at a time when there's a lot of interesting things going on in the world, a lot of people say, hey, it's all about AI, it's about more than that, right? It's we're going through these new tools are going to open up new possibilities. They're going to create a lot of consternation for people and a lot of change. How do you, how have you been bringing this kind of era of change and transition out in the audiences that you've been speaking to? 

Jeremy  8:00  
Yeah, I think a lot of it is trying to pull back on the mystique that's built up with our internet over the last two years. One of the things that I've noticed, and if you look at a recent New York Times article on this, all the big consulting firms are making like, 40% of their incremental revenue off Gen AI consulting. And what does that tell you, but that there's so much happening here that's based on hype a CIO, a COO says, what's our AI strategy? Better ask McKinsey. And then there's a big sort of project based on it, and all this money spent, when, in fact, everyone would have been so much more well informed had they just got their hands dirty like my kindergarteners did 20 years ago. If you want to learn something new, if you want to understand what it can do for you as a tool to accomplish a goal. It's way better to use it see what it's good for, what it's not so good for, and that's what I'm trying to do with students. Say, Hey, AI is not here to replace your career coach or to do all of your job search for you. But if you start to play around with it, two things are going to happen. Number one, you're going to be more effective with your job search, because you're going to be able to get through some of that friction a little faster. And then, number two, you're going to be unstoppable once you get to the workforce, because you're going to have the superpower you can use, whether you're a marketer or an engineer or a copywriter, to be maybe more effective at what you do. And so I really want to give people a sense of possibility, versus create even more mystique. This is something that only the experts understand.

Tom  9:20  
Yeah, I think that's super important, right? I used to start my conversations with everyone has to experience these tools, right? Exactly the point you're making. You need to get your hands dirty, put them in there, figure out what it's good for, what it's not good for, and they're evolving so fast at things they were not good for three months ago. Now they're actually a lot better at now, I actually even say that you have to develop your own relationship with these tools, because they are becoming like our colleagues in some ways, if you understand the power that that and the capability that's now in them, and it's really interesting, because people give you this weird look. It's like a relationship with them. I'm like, Yeah, try it. It was a big stepping stone for me learning to go from something I thought was just another way to do Google searches to something that I would say I've been thinking about this problem I'm thinking about like a, b and c. What do you think? And then it would come back and give me a completely different perspective of what I could be looking at. How do you explain to people what these tools are capable of and how to experience them? 

Jeremy 10:25  
Yeah, I love that example you just laid out, because I think that is the best use case. I think this is why it's so hard for us to grok, especially for younger folks out there, is that most of us have been basically on our own, making these big decisions in our life, trying to figure out what to do career wise, what to major in where to go to school, and then all of a sudden, you don't just have a magical gene that's going to do everything for you, because AI won't do that well, but it is the sounding board. And maybe if you're an executive and you're used to having a research assistant or a team of assistants to support you, you're used to that mental model. But for a lot of us, the idea that we don't just have to be locked in our own mind with that analysis paralysis, we can actually start to offload some of that sort of friction that stops us from living our best life, get feedback, break through that moment of stagnation. I think that's the best use case where people can do their best work if they're unburdened by having to feel alone in everything they do. 

Tom  11:17  
And for the person who says, It's I've had Google to do this. How is this different? How do you handle that question?

Jeremy  11:23  
Yeah, I think as an early Google user, I loved Google, because all of a sudden, all these obscure sources were unveiled. If you wanted to find out how the 1957 Chicago Cubs did, there was a web page for that, but I think that still was a limited range of the things that we're curious about as humans. Just trying to find facts is nice, but actually getting opinions or second opinions, that is where you really have breakthroughs. And I bet again, if you look back at some of the things where we've had our greatest accomplishments as a species, it's probably been a founder and a co founder, or an engineer and a business person working together, bouncing ideas off each other. And if we all had that co founder in our life, that maybe we can actually be more successful at everything we endeavor to do. 

Tom 12:05  
AI is co-founder. I like that. I like that. Okay, so you and I are sitting here on the UC Irvine campus in Southern California today. We're surrounded by about 37-38,000 students. All of them are here, and the surveys would tell you that either their number one or number two reason for being here is for their future careers and job prospects. Let's talk about your perspective, because this is really, this is your strike zone. What a careers for the future look like, and how are you trying to get people to prepare for the future that we're walking towards? 

Jeremy  12:36  
Yeah, I think that one of the things that Gen AI is laying bare is that a lot of the stuff that we assumed would drive careers of the future, like knowing some obscure coding language, knowing some macros inside Excel, are actually become more like commodities over time, because anyone who knows how to use chat GPT can replicate that same thing relatively quickly, versus some of the more traditional things that UC Irvine may have taught 50 years ago, Things like how to communicate well, how to be a great team player, how to build relationships. Those things are going to be more important than ever in a world where AI can handle all the technical things, but you still need someone to actually interact with other people, understand other people, build those bridges to other people. And so if I was giving advice to a current anteater, I would say, hey, absolutely, geek out on whatever that technology is that you're excited about, or study what you're excited about, but don't forget to get hands on experiences working with people in the real world, because that's going to be the meat of your job for the rest of your career, no matter what you do.

Tom  13:34  
Yeah, I was listening to a presentation earlier today. It was a presentation by OpenAI, by their product management team, talking about how they use the generative AI tools to do product management. And so much of it was about rethinking what product management is. And so I want to get back to so to get people to do differently, we got to get them to think differently. How do you challenge people in your seminars to think differently? 

Jeremy 14:04  
Yeah. So the number one thing that I say, and this goes back to your point around, hey, I want economic opportunity I came to use here fine to get a good job, is I want you to understand who controls that hiring decision. Because a lot of times I think students anthropomorphize it as there's this mysterious black box where my resume goes to die. That's what I'm up against when, in fact, going back to what we were just talking about, it's just other people, it's the recruiter, it's the hiring manager. What does their experience look like? And when I pull back the curtain on that and say, Hey, imagine reading all these cover letters that all begin the same way, because they were all generated by chatgpt, now you can see right away why this strategy is not working. This is why you're not getting interviews. But on the other hand, put yourself in their shoes with a resume that speaks their language, the exact keywords from the job description speaks directly to the culture of the organization and why you'd be a good fit for them. Imagine that how that would feel if you were on the other side of the hiring decision. And I think when students see that humanistic take on what's happening over at Google or over at the other employer company, and they say, Okay, I'm actually not going to focus on doing the same things that my friends are doing, because that makes me a commodity. That makes me exactly the same. I now have a little bit of the courage to stand out and really connect with that person on the other side of the screen.

Tom  15:17  
And there's such that's such a great example, because when you think about when you're customer centric, it's all about understanding that customer and finding a unique way to meet that customer's needs, right? That's where innovation comes from. When we talk about product innovation or customer intimacy, it's really the same game, isn't it? 

Speaker 3  15:34  
It really is. And I was just having lunch with your amazing marketing team today, and I have to say, I am just blown away by the fact that there are so many parallels between marketing and job searching. Now there may also be parallels between marketing and dating, and that's a whole other podcast. That's a whole nother podcast we can do. But I was gonna say that if you have that marketing mindset of I am here to serve my audience, and that service starts by understanding who they are, what they care about, what they need. All of a sudden, this process is not a black box. It's downright obvious. Because if you were in their shoes, this is what you would want to make your hiring decision easier. And so my number one challenge is come back to that core human skill, the thing that chat GPT will probably never be good at, which is empathy. If you can burst through that screen, if you can do a Vulcan mind meld with the person on the other side, you have a way better chance of getting that job, whether you've taken all the courses or not.

Tom  16:26  
Yeah. Okay, so I want to ask you about a question that you probably don't get a lot somewhere over the course of my career, and I've done a lot of different types of projects, and so change management has always been like a part of the equation. And someone along the way said to me, Look, unlearning is much harder than learning, Tom. And I think the older I get, the more I realize how just rote repetitious we get in our lives, we get into our patterns, and even if we like our patterns, don't like our patterns, we just follow them. And I've always really tried to push myself to evolve and change, but the focus has been I gotta let go of the past. I gotta unlearn even if it's been very successful for me, I don't learn to what's the role of unlearning as we walk towards this new world where the tools are giving us chances to really rethink and learn, to go about things in a different way?

Jeremy  17:20  
Yeah, I think the number one thing we can do is to understand what is the point of a tool? Why do we invent fire? Why do we invent axes? Why do we invent electricity? It was not just to wow our friends and have a cool parlor trick. It was to accomplish something. And so I think the number one way to break through that stagnation of, I don't know this seems scary, maybe it's dangerous for society is just think about, does this tool actually help me get closer to my goal? Yes or no. And I think with AI, as with every tool, there are good use cases and poor use cases. Obviously, if you're using AI to make yourself more similar to every other candidate, because you're using AI to generate the same resume, same cover letter, that's a really poor use case that gets you farther away from your goal, where, if you're using it to figure out who you are, what you really care about, what's the perfect fit with that passion out there in the world. Now that differentiation, that specialization by definition, helps you stand out, helps you get closer to that goal, which is the best use case for any tool. So rather than focusing on the tool itself or the hype surrounding it, focus on that end goal, that target at the end of the room, and is this actually going to get you there? 

Tom  18:24  
Yeah, I really like the AI for differentiation. Is it really I think we have a lot to learn from that, right? I think a lot of people just focus on we can make these things that we used to do, and we can automate them, and that makes me more efficient, so I can spend more time on something else versus how actually use these new, very powerful tools now to differentiate what I do or how we interact with our customer, that there's a big frontier for us in front of us. I think it's gonna be very interesting as more people become more comfortable in understanding how we might use these tools. So we had you here on campus today. You met with different some different groups, in addition to coming into the studio with us today, tell me, tell our audience about what those conversations were like. What were the messages you tried to leave with that because those who are working with our different staff, who are working with our students, so what were those interactions like? 

Jeremy 19:14  
Yeah. So I think one of the really big opportunities for anyone who's listening to this, whether you're a student, an academic leader, or business executive is that no one's figured this out. I work with 300 universities around the world. There is not one career center, one university that says we have the AI master plan. We know exactly. How do we lead on this thing? And so my sort of throw down the gauntlet moment is, could you pick up that opportunity and say, Hey, we want to be the leaders here. Now it's obviously hard to lead. You've got to figure out how to work through the ambiguity, figure out the best use cases, figure out what's right for your culture, your talent. But I really think that this is an opportunity that is still wide open, and the biggest opportunity is not making chips at Nvidia or building large language models, it is the application. Is the figuring out how to synthesize what this technology is brought to bear with the problems that we have to solve in society. And if you're a leader or a future leader out there, my challenge to you is, don't let this opportunity pass you by. 

Tom  20:13  
And so those that are those people that you got to interact with who are working with our students, what's the message that they have to take to our students. 

Speaker 3  20:20  
So I think that the big message is that I really want them to lead on this issue, because otherwise we revert to default based experiences. And again, the default that I've seen for hundreds and 1000s of students around the world is lowest common denominator thinking, commodity thinking. Let me just use AI to check a box, and in doing so, it might seem easier at the time, but I'm hurting my chances in that black box that we were just talking about. And if we just let students resort to their usual devices, we're gonna get the usual results, or even worse, results. Whereas, if there's a brave career leader out there, and you can be a career leader in a Career Center as a faculty member, as a staff member, basically anyone who works with students has a chance to be a career leader. I think this is the biggest opportunity to lead on, because this is the stuff that students won't just be using to get the job, they'll be using it to get the next job and to keep that job. And that's why it's so important that we have to model those best practices starting today.

Tom  21:13  
Yeah, so we were talking earlier about that we've run this large scale class here, really to help our students experience get their hands on. We had students from every major come into that class. Some were very comfortable with these tools. Were using them on a daily basis. Others were very open. This is the first time for me, but they were curious. And yeah, I got up on day one of that course, and I told them a couple of stories about where I was, when the internet happened, right? So this is a set of students who do not know a world without the internet, without Google, and here's this middle aged guy getting up and talking about but what I told him is what I realized, and the opportunity, it was a unique moment in time, right? And my career just jettisoned forward because I jumped in early, before the rest of the crowd was and I got to do things that today. These things may seem almost ridiculous now, but at the time, the internet wasn't a certainty. There were a lot of people who thought, other than exchanging emails with each other, there was not going to be any use case for the internet. And so I told them a few of these stories, and I said, this is your moment in time. I don't know what the future is going to look like. I just know that from here, there's going to be so much opportunity that is undefined, that it just lean in and that and I said, this is why we created the class, because we want you to walk out of here not just with your diploma, but with a understanding and an optimism to you can create whatever future you want, is your message similar is when you sit down and talk to students?

Jeremy  22:47  
I love that so much. Tom, because I really do feel that same way, and I want to be clear that it's not like a gold rush thing. It's not, oh, this is your only moment. Take the internet. For instance. Netscape Navigator comes out 1994 Google's not created until 1998 we're only two years into chatgpt as we record this, and so I think there's still tremendous opportunity out there. But it behooves students who are not even thinking about starting a startup or having a tech job to at least get their hands dirty, as we were talking about, just be fluent and conversational in this technology. So you know what it's useful for, where it's limited. And then as you start to go into any endeavor, whether it's social impact, work, environmental work, policy work, you're gonna start to see these applications. Because unlike everyone else who was scared and putting their head in the sand, you had the guts to at least get out there and see how this thing worked. And if you can figure out that application in that specific space, then I think you get to be the Google of this time for whatever that space is.

Tom  23:39  
Absolutely. okay. Prediction time. Jeremy, one bold prediction about what careers will look like 10 years from now, from the unique vantage point in which you're looking at this opportunity in this time.

Jeremy  23:52  
So I'm gonna take that challenge Tom, and I'm gonna actually double down, or quintuple down, as you see my drift here. I'm gonna argue to you that in two years, not 10 years, two years, there will be more job descriptions in the world that call for Gen AI experience than call for experience with Microsoft Office. 

Tom 24:12  
Whoa, Satya. All right, okay, yeah, keep going with that. That's awesome. 

Jeremy  24:16  
I was gonna say the reason for that is that as a hiring manager myself, and I was leading the marketing team at Khan Academy. We were a small nonprofit trying to do big things in the world, and people said to me, oh, we can't use AI. It's going to be unethical. It's going to have all these rad implications. I said, How can we not use AI if we are trying to do the most with the least? How could we not take advantage of the best tools available today? And I think if that's the way that Khan Academy thought back in 2022 by 2026 every CMO, every CEO, every COO, is going to be demanding the same with their staff. Get more done, use the best tools, drive the best results. And again, if you want to get ready for the future is not that far off. The future is now.

Tom  24:57  
and then has the progression of these tools surprised you at how fast they're progressing?

Jeremy  25:02  
In some ways, I think it's actually how slow, and the reason for that is less about the technology and the size of the windows and tokens and all that stuff, but actually the fact that there's this very uneven distribution, where in any organization, I meet people who are way deep in AI and they're getting all this stuff done, but they're not telling anyone. There's still this kind of stigma of, oh, maybe it means that I'm not really good at my job, or I'm cheating somehow, or they're gonna give me more work. Exactly, there you go. And then, as a result, I think it slowed the spread in a way that wasn't a problem for the internet, because the internet was more social. By default. People were sharing links and emailing back and forth and all that stuff. And so I suspect that as word gets out and there's a little more top down intervention, more and more employees are gonna get on board, more and more students are gonna get on board. But I think right now, a relatively small slice of society is getting outsized benefit from Ai, but very few people know about it.

Tom  25:55  
So you don't think we've hit that asymptotic curve yet? 

Jeremy  25:59  
no. And I think if the stats bear that out. If you even look, even in universities something like, I don't know, a third of students say still haven't really used AI two years into the experience, they're scared. They're where they're gonna break something, they're where they're gonna get in trouble. And I think the fact that there's still this sort of cloud over this ambiguity creates opportunity for others, whereas Warren Buffett says when other people are fearful. That's when you rush in and seize that opportunity that's awesome.

Tom  26:23  
All right, Jeremy, I want to thank you for joining us on the podcast today. Want to thank you to coming down to our campus here, and I hope you had a wonderful day. 

Jeremy 26:26
Thanks so much, my pleasure. Thanks, Tom.