How to Help Students Build Their Career Toolkit with Mark Herschberg

Mark Herschberg - Author, Instructor, & Event Speaker


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In this episode of the Prep Period Podcast, Averon CTO and author Mark Herschberg covers the key learning points from his award-winning book, “The Career Toolkit.”
Mark shares how educators can help their students develop skillsets for career planning, explains how students can cultivate leadership skills in the classroom, and highlights the importance of teaching crucial skills such as:

  • Communication
  • Ethics
  • Negotiation
  • Networking

Narrator: [00:00:00] You’re listening to Prep, Period, the only podcast for teachers that’s focused on quick wins and actionable tips that can be implemented in your classroom tomorrow. Prep period starts in three two one. 

Brian Bean: [00:00:16] Hello, welcome to Prep Period podcast. My name is Brian Bean. I’m your host today, as usual. And today our guest is Mark Hirschberg. Man, Mark’s done a little bit of everything and a brilliant man taught at MIT for years and years and years. He is going to talk about three specific things that I think are very, very important to teachers and students in general. We’re going to talk about career planning. We’re going to talk about giving students opportunities for leadership and how to help them develop their interpersonal dynamic skill set. Super excited. So with that? Hey, Mark, thank you very much for coming.

Mark Herschberg: [00:00:54] Thank you for having me. It’s a pleasure to be here.

Brian Bean: [00:00:56] I’m excited. I tell you all of our teachers out there, a lot of our teachers that listen to this podcast are in career and technical education, a lot of business teachers on marketing teachers. So I think this is going to be, especially for them, very poignant something that they’re going to really look forward to. Before we dive into our questions and some of the topics we’re going to talk about today, I want to just give our listeners a little bit of background for you. Some context. Just kind of a little guest bio, if you will. So Mark is the author of the career toolkit Essential Skills for Success That No One Taught You. He was educated at MIT. He spent his career launching and fixing new ventures at startups Fortune five hundreds and as well as in academia. He’s developed new software languages, online marketplaces, new authentication systems, and he’s even tracked criminals and terrorists on the dark web. Mark helped create what’s called the Undergraduate Practice Opportunities Program. That’s MIT’s career success accelerator. If I understand, correct? Yep. And you then you taught at MIT for 20 years as well. And then you serve on the boards of numerous nonprofits like Tech, Youth and plant a million million. Is it plant a million corals orals?

Mark Herschberg: [00:02:20] Yes. Like Plant a million trees, but under the ocean?

Brian Bean: [00:02:23] Oh, that’s legit. That’s awesome. So real quick. Before we go in, I got to ask tracked criminals and terrorists on the dark web. So that’s awesome. I don’t think I’ve ever had anybody on the podcast before that quote-unquote track terrorists on the dark web can tell me just a little nugget about that.

Mark Herschberg: [00:02:45] My graduate work was in cybersecurity, and that’s certainly where I’ve done some of my work at this particular company. We were going onto the dark web and basically doing online intelligence gathering. Who are the communities of terrorists or cybercriminals? What are they doing? How are they working? And as we gather this information, we could share it with both certain government agencies, but also with corporations that we’re just trying to figure out who might be coming at us and how, when and why.

Brian Bean: [00:03:16] Wow, that’s that’s a jet man. It’s something, I mean, that sounds like somebody made a movie off of that, and that’s like your life. So that’s fantastic. Also, when we’re not doing a podcast, I’m going to talk to you. My son’s dream is to go to MIT, so I’m going to pick your brain. Maybe you could give me some tips that kind of help them out there.

Mark Herschberg: [00:03:36] Absolutely.

Brian Bean: [00:03:37] So now, besides the plethora of other endeavors that you’ve had throughout your career, you I started by mentioning that you wrote a book and that book is all about what you call the career toolkit. And one of the things that I really like about how you’ve organized kind of organized your thoughts in that book is you’ve categorized them into three main topics of career planning, leadership and management and then interpersonal dynamics. So if you’re OK with it, I kind of just want to focus our time on those three areas and discuss some strategies that teachers can take to incorporate those into their various courses, whatever they teach. So let’s do it. What right off the bat? What are your some of your thoughts about some strategies that teachers can use?

Mark Herschberg: [00:04:31] First, I have a problem with how a lot of career planning is done because it’s very much here’s a job. Do you think you want this job? Do you fit or not a binary choice? And unfortunately, we don’t even give kids an accurate reflection of jobs. So the best example for this, let’s think law because everyone knows what a lawyer does. Ask a 12-year-old. They understand what a lawyer does. Now we’ve seen lawyers because we’ve seen them on TV. Yeah, it’s always super dramatic. Yeah, it’s always that. Hence, courtroom scene and lawyer comes in and lawyer explains, Oh, we help people with conflicts and contracts. Now if you look at what a lawyer actually does very little courtroom drama, most lawyers will tell you they rarely set foot in a courtroom. Most lawyers spend their day sitting in a room by themselves, reading contracts, redlining contracts, looking through prior case law. It is very different than our image of law. And when we tell students about different types of roles, we talk about the highlights of them. But we don’t talk about, well, that highlight the solving the engineering problem.

Mark Herschberg: [00:05:39] That sounds great, by the way, you’re also going to be spending probably about two hours a day in meetings. That’s what it means to be an engineer at some company. Sometimes more. And so we really want to understand what are you doing? And by the way, when I interview people, this is a very explicit question I asked to make sure we have. The right expectations, how do you like to spend your time, how much time are you expecting to be doing this exciting piece, maybe going into courtrooms versus redlining contracts or sitting in meetings or doing other things? And let’s really understand what these components are. And you do so for two reasons. First, so the student doesn’t think I want to be a lawyer to have this courtroom drama, but also to understand, OK, there is a lot of time and meetings. So engineering, for example, it’s a lot more collaborative than most people realize because the homework we do by ourselves and school is done typically individually. But most engineering work, it’s collaborative, excuse me, collaborative.

Brian Bean: [00:06:37] So any words you want collaborative? Sounds great. I love it.

Mark Herschberg: [00:06:42] So, yeah, we’re so we’re going to teach them new vocabulary for these new

Brian Bean: [00:06:46] Career planning is not as important as can you pull off making up words mid-sentence,

Mark Herschberg: [00:06:52] But it’s understanding how much time do you spend in meetings, working alone in office versus out of office? And we want students to think not about jobs, but about specific activities. Do you like structure? Do you want a job that’s very nine to five and you have your plan and these weekly meetings and what you do versus so says I want to be on the field. I want to just set my own hours. I want to meet new people every week. And then you’re not saying, Well, I want this job or not. You’re saying, I want a job that gives me this opportunity or not. So sure. Bring in people, bring in the doctor, bring in the accountant and have them talk about their jobs. But make sure you look not as a holistic do you want this job or not? But what are the attributes of this job that sound interesting or not? And it’s not just do you do math or writing, but how you spend your days, and that’s what we want to focus on as we train students.

Brian Bean: [00:07:44] I love it. I think your word choice is just spot on to be like you emphasize planning for a career, not just preparing for one. Like, I think if you go talk to most teachers, they’re going to talk about how their job is to help prepare students for the real world, help prepare them for their future careers. And I don’t know how much individual teachers realize that they can have an impact on the planning part. And I think that’s I think it’s a very important paradigm shift that you’re discussing that you’re discussing here. You know, how do so how does the teacher go from, you know, this class is going to prepare you for x y z career? And how do you shift that to this class is important and is an important part of your plan for x y z career.

Mark Herschberg: [00:08:39] If you think about the other classes we have, let’s take science. For example, your high school science class doesn’t make you a scientist. There’s a lot more you’re going to learn in college, probably grad school.

Brian Bean: [00:08:52] I taught science for six years, and I barely even thought I was even close to a site. I wasn’t a scientist, let alone my kids sure weren’t. So this is a very good example.

Mark Herschberg: [00:09:02] If you’re doing it right, you are teaching them how to think scientifically because the problems they’ll eventually space in 10 or 20 years, those problems might not even be in existence probably won’t exist. Yeah, right. But we’re going to teach them the scientific method. And when you get the scientific method, the ask questions, hypothesize, do an experiment, learn that’s a universal tool that can be applied no matter what science problem you’re facing. And so with our careers, what we’re teaching them is not, if you know, x y z, you’re ready to do this career, but we want to teach them these metal tools, how to think about your career, how to approach it, how to recognize problems and figure out ways to solve those problems. Not what the solution is. But here is your toolkit for solving that problem. That’s what we want to teach them in our career planning.

Brian Bean: [00:09:54] It almost sounds a little bit like you’re you’re shifting the emphasis away from. And for anyone who knows me and my teaching model, they know where I’m going with this. You’re shifting the emphasis away from content and more towards a skill set. It is. It’s not as important that you learn this stack of facts, objective facts. What’s more important is that you learn skills of what, what to do with those facts and what to do with any new fact and information that comes in. It’s that skill set that’s really what’s going to be the important thing in the long term.

Mark Herschberg: [00:10:30] Absolutely. Right in my own field as a CTO, the languages I learn, the software languages I learned in high school. No one uses those. I use languages that didn’t exist. But by learning how to think like a software developer, learning how to think like an engineer that’s going to carry with me no matter what the particular technologies are. And when we think about the jobs of the future and we hear these things, most of the jobs don’t even. Exist today, they’re going to be new, they’re going to be different. We’re not teaching, here’s the information for the job, but here’s how to think, and that’s going to help you in this category of jobs.

Brian Bean: [00:11:08] And I think it’s important to emphasize that what we’re not saying is that the information you’re learning in school doesn’t matter because it’s going to be irrelevant one day. That’s all we’re saying at all. What we’re saying is that use the information that is current today to build the skill set up so that when if it becomes obsolete, you’ve got the skill set to adapt and evolve. But that’s information still important because it’s a tool like anything else.

Mark Herschberg: [00:11:37] Absolutely. These are general concepts, meta concepts, and they’re abstract. And if you don’t teach it to a student without the context of today’s world, today’s information, today’s circumstance, I think it would be hard for them to grasp. So do use today’s information jobs, but take that extra step and emphasize that meta to once they get the concept. How might that be applied to a different type of job in the future?

Brian Bean: [00:12:03] Yeah, not to mention, if you use the word meta, you sound smarter. And so your students are going to be like, Yes, I’m all meta. And so that’s just going to win right off the bat. I like it. Let’s let’s shift gears a little bit now. I love the emphasis on career planning. I thought the next part was very intriguing where you focus on leadership and management. Now with this. I think there’s a lot of opportunities to to explore this concept leadership and this topic, obviously, it’s near and dear to me. I’m literally getting a doctorate degree in this very topic right now. So let’s talk about leadership and its role in schools and what you can teach. So two questions. First, in your mind, what is leadership like? How would you define leadership?

Mark Herschberg: [00:12:58] To me, the best solution or the best definition of leadership is someone who has a vision for a positive change and positive just means an affirmative change. Changing something proactively could even be removing something and then convinces other people to buy in and go along with trying to create that change. That’s it.

Brian Bean: [00:13:22] I think the key there is that second part, you know, the definition of, you know, leadership is having followers, quite frankly, where you go with them and where you’re taking them is, you know, can be different with each person. But OK, so that’s our baseline, that’s leadership. So with that understanding that proactive engine of change, how can teachers give leadership opportunities to students? And let’s say we’ve got a business teacher out there listening. They’re like, Hey, I like that idea. How can that teacher give opportunities to that student to learn and exercise leadership skills?

Mark Herschberg: [00:14:04] Very importantly, for high school and even many college and some grad students is to emphasize the difference between positional versus influential leadership because a lot of students don’t get this. So positional leadership comes from authority. I am your boss. I am telling you to do this. Yeah, the military is the ultimate example. Yeah, for sure. Authority. It’s not even really leadership, it’s authority. And it comes from your role as a teacher. You can say you’re doing this homework. If you don’t like it, I’ll fail you.

Brian Bean: [00:14:33] Yeah, I’ve got. I’ve got leverage, so I’m in charge.

Mark Herschberg: [00:14:37] True leadership is you’re my peer at the company. I can’t order you to do it. I can’t cajole you, but I say, Hey, we really should do this project. We should go in this direction and convincing people on the quality of the idea of the pitch of how I inspire others, how I convince others. That is true leadership. And most students don’t understand a difference. They see leadership position. So you want to break this and get them to understand the difference between positional versus influential because otherwise they sit around just waiting to get the position.

Brian Bean: [00:15:14] Yeah. And that’s that’s well, that’s tricky for a teacher to do because that teacher is in an authoritative leadership position in the classroom and they obviously can’t vacate that they can’t abdicate that that leadership or can they? Is there a way for teachers to exemplify this influential leadership to their students so that the students can not only be given opportunities to exercise it, but also have a modeling behavior to be able to look at and learn from?

Mark Herschberg: [00:15:46] You certainly can now, I think a good way to teach this leadership is something you can’t just teach by lecturing at the board. No, like playing sports, you have to do it and try it, experience and learn. So I would recommend create small groups within those groups, give different people a chance to be a leader. So maybe throughout a semester or a year, you might have four different projects. And if they’re in teams of four people, each one gets to lead a project. But here’s the key. It’s not just, well, guess what, you’re going to lead for this module and then she’s going to lead for that module. What you want to do is have during that leadership experience, before, during and after, have some discussions, have them talk about their experience, whether it’s keeping a journal, whether it’s talking to others, but you want them to think about, reflect and learn from their own experience and from others. And that’s what’s going to help crystallize some of these nascent leadership experiences for them. Now, as the teacher, you bring up a good point. How can you model this? Perhaps some of what you do is letting students lead some of these modules. You have a module coming up say, OK, you’re going to be in charge for the class for next three days. You’re going to run us all through how we’re going to learn this module.

Brian Bean: [00:17:08] Yeah, no, I like that. My first thought, as you were describing, I was like, Well, if I just assign a kid to be the leader of the group, then that kid has positional authority in the group and it undermines exactly what we’re trying to do. But as you get talking, I like the idea of giving the student the. Responsibility often can breed leadership and putting a student in a position of responsibility to be in charge of this over the next few days, kind of a thing gives them an opportunity to step up, you know, and as long as you give them the resources and the opportunity, I think you have a better chance of fostering that kind of environment that would cultivate that leadership skill. So I really like that idea.

Mark Herschberg: [00:17:50] I do think it’s OK to do some of that. I am endowing you to be the leader of this group right now. This is leadership, influential leadership with training wheels. There will be a little of this, but but it’s saying, OK, Brian, you’re going to be in charge of this group of you and your fellow students for the next two weeks. They do the module but remember you’re in charge, but you can’t force them to do anything and you even make it clear. And if your group says, you know, we don’t like what you’re doing, we’re not going to do it great, you can all fail that module together.

Brian Bean: [00:18:23] Your choice? Yes. Yes. Along with leadership, we’re going to talk about consequences. So you just do as you please. I like it. Kate thing we want to talk about. We’ve got a few more minutes. I want to I really want to dive into this concept of interpersonal dynamics. So again, we’ve got a two-part question. I’ll just give you both of them and I’ll let you run with it. Ok, so first. Why is that such a valuable skill set for students to learn early on these interpersonal dynamics and all? Have you kind of expound on what you mean by that as well? And then to, you know, first, why is it so important to learn early and then second again? Do you have any advice for teachers on how to approach that subject?

Mark Herschberg: [00:19:09] What I cover in that section, communication, negotiation, networking and ethics, this is how we relate to other people.

Brian Bean: [00:19:20] Really get dynamics of interpersonal relationships?

Mark Herschberg: [00:19:22] Yes. And I really get to where the fundamental pieces of all this. So let me give an example using negotiations. Imagine you have a student who is graduating college has a job offer for fifty thousand dollars, but instead of taking it, this student goes to negotiate and negotiates a $1000 increase. Two percent. It’s not a big lift if you didn’t run, does nothing else for the next 40 years of her career, she just earned $1000 more for 40 years. One negotiation five minutes of work got her forty thousand. Yeah, but of course, you’re not just going to have one job for 40 years, you’re going to have raises and promotions and other jobs, and it’s going to be bigger than a thousand. And if you use that same negotiation skill, if every time she changes a job, she gets a thousand more. Think of the cumulative effect. This can actually add six figures to your income easily. Now we’re just talking about income. In fact, we know it’s not just about getting more money in your job. We negotiate with our peers all the time, our co-workers, our fellow students. And it’s not just about money and something numerical. Coming up with better solutions because we have better negotiation skills is going to be rewarding us over and over and over. Now I use negotiations because it’s easy to do the math and see how it applies if you start off being a little better at networking. If your network grows two percent faster than someone else’s network each year. Do the math on that you get again, exponential growth if you are slightly better at communicating, even leading or one of these other skills.

Mark Herschberg: [00:21:09] It’s not that someone says here’s a thousand more, but you get more opportunities, you get more success and success begets success. So we really want to emphasize these basic skills. And here’s the secret you don’t need to be the world’s best negotiator or communicator or leader. We really run a race, not an absolute time trial. And so we are competing against our coworkers, against other applicants for jobs. As long as you are doing better. You are going to win. So all we have to do is be just a little bit better. And one of the keys to that, when we emphasize these skills and we get this mindset shift negotiation isn’t how do I get the most for me? It’s how do I figure out how to enlarge the pie? How to make something that is palatable to you? Well, still trying to get as much as I can for myself, but I don’t just think about me. I think about us. You are not my opponent. You are my negotiation partner. And so all of these have different mindset shifts. And once you get that shift forever more when they walk into negotiation, they’re not going to think, How do I take as much as I can from you? But how do we work together? And so each of these areas, when you get that mindset shift, people see opportunities in a new way. They see opportunities for their own self-growth, and that’s going to help them accelerate their learning. So the earlier we can do that, the faster and further they will go.

Brian Bean: [00:22:38] Yeah, for sure. I love it. It it reminds me of, I’m assuming you’re familiar with Chris Voss.

Mark Herschberg: [00:22:44] I know of him. I haven’t read his book.

Brian Bean: [00:22:47] Oh man, it’s fantastic. You would love it. You would. It’s going to be right up your alley. I would highly recommend it. It’s a great one.

Mark Herschberg: [00:22:54] I’ll note about his book, and certainly he’s a very smart, capable negotiator. I’ve looked through summaries. I’ve heard him speak. He does a very certain type of negotiations. When he shows up. It’s high stakes. There’s no pause button. When you have a hostage situation, you’re there till it’s done. Exactly a lot of the negotiations we do in business. This happens over days or weeks. That’s not to say people don’t get emotional, but there’s not this, you know, Oh, we’re here across the table. We can take a break. I can, you know, I’m tired today. I’m going to sleep, I’m going to respond to your email tomorrow. And there are other techniques. He emphasizes a lot of interpersonal emotional techniques, as opposed to classic negotiation techniques that we see out of research from a lot of business schools.

Brian Bean: [00:23:44] Yeah, that’s awesome. Well, thank you so much for coming on. I. I got about 14 other questions that came to my mind. Maybe we’ll have to have you back for another episode, but for now, thank you so much for spending some time with us. I know our listeners are going to appreciate it. Real quick to just to kind of wrap up and close if somebody wanted to get a copy of your book or learn more about some of these concepts and principles that you’ve shared with, where would they go to do that?

Mark Herschberg: [00:24:13] You can go to my website, the career toolkit books, and there we can take you to Amazon or many of the other places that sold. You can follow me on social media or get in touch. There’s a whole resources page with lots of free resources online. Oh, great links to other websites, some free downloads. All of this. It’s available on my website. The Career Toolkit Books.

Brian Bean: [00:24:34] Wow, you said the magic word for teachers out there. So yeah, free resources is the way to go. Well, thank you very much. Appreciate it.

Mark Herschberg: [00:24:42] Thanks for having me on today.

Brian Bean: [00:24:44] Thank you very much, Mark, for coming on to our show. Another great guest. Another great episode. As usual, if you know anyone out there or you yourself would like to be a guest, please shoot me an email at and [email protected] it’s Brian with an “i” bean just like a vegetable. And if you are interested in learning more about some of the concepts that Mark likes to utilize and what his philosophies are, go to and you can get lots of free resources there. If you want to buy you the book, you can, but he’s got a tremendous amount of resources for teachers that you can get for free at

Brian Bean: [00:25:28]  Thank you very much, and we’ll catch you next time.

Speaker: Mark Herschberg - Author, Instructor, & Event Speaker


Mark is the author of The Career Toolkit, Essential Skills for Success That No One Taught You.
Educated at MIT, Mark has spent his career launching and fixing new ventures at startups, Fortune 500s, and academia. He’s developed new software languages, online marketplaces,
new authentication systems, and tracked criminals and terrorists on the dark web. Mark helped create the Undergraduate Practice Opportunities Program, MIT’s “Career Success Accelerator”,
where he taught for twenty years. Mark also serves on the boards of non-profits Techie Youth and Plant a Million Corals.


The Career Toolkit