Breaking Down That Much-Needed Career Toolkit With Mark Herschberg

There are some much-needed skills to achieving success and personal development that aren’t taught or explored well at school. Frustrated with this, Mark Herschberg designed a career toolkit to start an education shift in this area, which eventually lead to him being part of MIT’s Career Success Accelerator. Joining Dr. Diane Hamilton, he explains how they use peer learning groups to instill the required skills to achieve success and why millennials are much easier to grasp new ideas than boomers. He also delves into the best recipe in team building, detailing his interview tactics, how to embrace mental diversity, and the importance of self-assessment. Mark even touched upon his idea of successful leadership by talking about charisma, getting rid of unnecessary meetings, and eliminating work after hours.

TTL 844 | Career Toolkit


I’m so glad you joined us because we have Mark Herschberg. He is an instructor, MIT’s done work with Harvard and so many others. He is the author of The Career Toolkit. It’s going to be a fascinating discussion.

Watch the episode here

Listen to the podcast here

Breaking Down That Much-Needed Career Toolkit With Mark Herschberg

I am here with Mark Herschberg from tracking criminals and terrorists on the dark web to creating marketplaces and new authentication systems. Mark spent his career launching and developing new ventures at startups and fortune five hundred in academia. He has a book that I’m very interested in talking to him about The Career Toolkit: Essential Skills for Success That No One Taught You. He has a very fascinating background. I could spend all day giving your bio. I’ll jump into it.

Welcome, Mark.

Thanks for having me. It’s a pleasure to be here.

I was looking forward to this. Everything from MIT to Harvard in your background, I thought maybe you should give it because you a lot of people want to know what your platform is and your experiences that led you to this point.

I think about myself as having two parallel career paths. My primary path, I came out of MIT with a couple of degrees back during the dot-com era in the ‘90s. I began as a software developer, I wanted to become a CTO. As I began to understand what a CTO does, I realized that person isn’t simply the best programmer. I’m the worst programmer than when I was doing it 50 some hours a week. To be a CTO or any real leader. There’s a whole bunch of other skills, interviewing, team building, communicating, negotiating, leading, all these skills but no one bothered to teach them to us in college. I saw I had the skills gap and went out to start developing these skills in myself.

The World Wide Web wasn’t as well developed. We didn’t have wonderful podcasts like this. It was a little bit of a challenge. As I built up the skills myself, I realized these are not just for the leaders or for the C-suite. These are skills that all of us can benefit from. I looked for people who had these skills when I was hiring. I worked across the startups and the larger companies, I kept trying to hire for these skills but quickly realized they’re not getting it either. They suffered the same problem I had, which is that universities don’t teach it. I realized they had to build not by, “I couldn’t hire for this. I had to train it up.”

I developed some training programs shortly after I began doing that. MIT had gotten similar feedback. Corporations had come to MIT and said, “Your students are great but here are the skills that we’re trying to find.” It’s not just for MIT students. Similar feedback in other universities. This applies to people at all levels of experience. They want to see leadership, communication, teamwork, negotiation, strong networks, all these skills but they’re not being taught.

At MIT, they wanted to develop this program. When I heard about that, I said, “I’ve been working on this, happy to share some of my research some of what I’ve developed.” They said, “Yes, please do.” I helped develop this course known as MIT’s Career Success Accelerator and they said, “We’ve got wonderful professors but we can benefit from having practitioners like yourself.” I’ve been fortunate enough that for the past years, I, along with other people like me have been back to work alongside the professors and teach this class to MIT students.

[bctt tweet=”When you are teaching leadership, there is no formula. There’s no three-step process for communicating.” via=”no”]

That must be a fun thing to teach. A lot of what you’re talking about ties into what I’ve done with curiosity and they have incorporated my curiosity courses at Forbes School of Business. When you look at some of the skills, this fascinates me because I wrote my dissertation on emotional intelligence and I’d look at soft skills as something that I tried to incorporate into the courses when I was MBA program chair at Forbes. We hire for our knowledge and we fire for our behaviors in the working world. They’re not teaching these things in a lot of these business courses. It’s hard to teach some of this. I focus primarily on curiosity and perception in my last two books but you’ve mentioned so many other important things in interviewing, negotiating, the list that you were saying. What do you think of those skills? What is the hardest one to teach of all those skills?

I don’t think any are particularly hard to teach but we have to teach them differently. We traditionally teach the way we teach most courses at MIT, other universities in high school, a professor. A wise person stands in front of the class and says, “Do this, this, and that.” That’s fine when you’re teaching chemistry, “Here’s the formula.” You’re teaching computer science, “Here’s the algorithm history. Here are the dates.” When you are teaching leadership, there is no formula. There’s no three-step process for communicating. The best way to teach this, the way that we teach in the class at MIT, the way top business schools teach it, and the way we can talk about how you can teach this in your organizations. You want to create peer learning groups.

You have some content and that content stimulates the discussion. That could be a case study, it could be using a book or podcast like this one. You have a peer learning group. In that group, you start discussing, “Here’s a communication challenge.” Here’s how I might think of approaching and you’ll share how you’ll think we’re approaching someone else. I never would have thought that’s a different approach. Maybe it doesn’t work as well for me but even becoming aware of how you perceive it, seeing a different facet of the problem expands how I look at it in the future. It helps me understand that person facing the challenge. When I think of, “He’s doing a terrible job. She’s doing your approach.” It’s not mine but I get what she’s doing. I expand my understanding.

How we need to teach this is by creating these peers learning groups and having a discussion. The other reason we need to do this. We traditionally teach in a just-in-time manner. When you go for corporate training, they say, “We have a new accounting system, we’re going to send you for training and learn how to enter expense reports. You’re getting promoted to this position. Here’s a two-day leadership seminar.” In school, we knew next Tuesday at 2:00 PM, and you have a test on this. That’s not how life works. No one says, “By the way, next Wednesday at 3:37 PM, you’re going to have a communication challenge.” We need these skills, not only to be taught in this manner but to be regularly top of mind. You can’t teach at once and think you’ll remember forevermore. Having these ongoing peer learning groups that’s going to help keep it Top of Mind, help reinforce it. As you get these spontaneous challenges, that is our work, you’re going to be ready for it.

It’s so important what you’re talking about because, in my research in perception, you’re talking about a lot of what I talk to companies about. We see things from our unique vantage point. We have our backgrounds, or gender, or our culture, every form of what we are. If we don’t recognize that other people have reasons for coming up with what they have, and what their ideas are and that they’re valid, whether you agree with them or not. You’re missing a chance of developing this big empathy piece.

I had Daniel Goleman, we were talking about the value of curiosity to developing this and how important curiosity is. You get in this status quo way of doing things. You don’t even recognize that there are other ways of doing things. One thing I found when I went to ASU in different schools where they had a lot of teams set up in your university experience. In a lot of courses where I’ve taught, you’ll get a few people on a team and education atmosphere who take over. They do all the work and then the other people on the coattails show up, they do the minimum. How do you get away from that? If you go to MIT, you’re more motivated maybe than some other schools. How do you get everybody to give the same level of effort in that setting?

If you’re doing one of these peer groups within your organization, you’re probably going to be looking at hoping people are self-motivated enough to participate, someone shows up and doesn’t want to speak. Once a person showing up in the first place, you can’t force engagement other you can’t have a dialogue about why this person is holding back. Is it fear? Is it imposter syndrome? Is it not feeling connected to the group? You can have that discussion. At MIT, when we do these classes, we do these small peer learning groups. We do a lot of hands-on experiential activities. We’re not lecturing to the students.

Some of the activities are specifically designed so that when one or two people in the group go into hero mode, “I’ll power through this, I’ll get it all done and you all can follow along.” They will fail that particular exercise because it involves having each person on the team engage in the activity, and they fail miserably. That’s part of the goal because particularly how we teach at this MIT program, we like getting that failure. These students are not used to failing they are used to get A’s on everything. Suddenly, they did the math right. They did the engineering right but they failed. At that moment, we say, “Let’s talk about why you failed. It wasn’t that you couldn’t figure out the complex part of it. It’s that you didn’t work together as a team. You didn’t communicate here, you didn’t engage. That’s where the misstep happened.” That’s where the learning happens. I say, “I get it. I have to make sure to engage to my teammates now and in the future.”

TTL 844 | Career Toolkit
The Career Toolkit, Essential Skills for Success That No One Taught You

It was John Couch, who was on my program from Apple, who wrote a book and he was talking about how he learned to be a great student for memorizing and doing all these things. He never missed anything. In one test, they switched it around to make him extrapolate in a way that wasn’t exactly a memorization way of doing things. It threw him. He recognized how he needed to learn in a new way. The CEO of Prisms VR and I loved what she’s doing there because she’s taking math and putting it in a realm where people see it through virtual reality glasses. If you wanted to see COVID spreading instead of hearing the problem that X plus 2 equals Y, you’re seeing what it means instead of an equation on a piece of paper.

What you’re doing is bringing life to something that a lot of people haven’t even thought about. To bring life to these soft skills, these different critical ways of getting along in the workplace. Are you finding in the real working world that this is easier for people who are newly out of school to get and learn this type of thing? How entrenched are Boomers in the old way the status quo way? How hard is it for them?

I’m hesitant to give it an exact answer because I haven’t taken the data in this age group. I would say in general and this is anecdotal. Younger folks are very eager to learn. They know what they don’t know in many cases for a Boomer. For people in their 50s or 60s, they’re starting to say, “I’ve I already know this stuff.” They don’t know what they don’t know or they’re not motivated. Some people are either motivated to learn in which case they keep learning or they say, “Good enough.” We’re seeing people towards the end of their careers starts to say, “You know what, I’m 55, you might be able to teach an old dog new tricks but this dog just got ten years to go, I’m going to get through it and be fine.” It resonates a little better for folks in their 20s and 30s. I don’t want to discount those in their 40s and 50s who are listening to Dr. Ruth Gotian’s podcast with you earlier. She’s a friend of mine. She says, “The top people know to continue learning and those of us who do no matter our age will keep learning.” Some of it is intrinsic to who we are.

Those who are curious will continue to explore and develop their skill set. That’s why I focus so much on curiosity because there are so many things that hold people back from being curious. If we can develop that it helps build a lot of these soft skills, emotional intelligence, empathy-type things that we’re not getting and we haven’t received. What kind of data did you get at MIT? Did you do any research to see the before and after of what this course does? Are you in the process of doing that to see employability or any other data?

We’ve done it within the class itself. While they’re still undergrads, we’ve done surveys to see how they are in understanding and developing these skills. I have pressed MIT for years to do a more longitudinal study because we have alumni, nearly twenty years old. I have pressed MIT to try and get that data. Unfortunately, that has not been happening yet. I hope one day to get it.

I’ve been looking for a lot of data to see the value of curiosity to innovation and engagement. Novartis did some research on engagement which was good to see that curiosity improves engagement. We know they’re losing $550 billion a year here in the US, according to Gallup on engagement. If we can get more research done on how this ties in because we want to be able to show this is such a valuable thing for people to learn all these skills. In addition to your book, didn’t you create an app to go with this?

I did create an app as well. One problem that we have with books. You read a great book like yours, and they say, “Great tips.” A month later, you forget 90% of it because we’re on to something else in our life. We know that spaced repetition works. The app can be used in two ways. First, you download the free app. You don’t have to open it each day. It pops up one of the tips from the book. It’s that reminder comes up. That’s an alert, you look at it, and swipe it away. That helps reinforce the content. You can set if you’re focused on the chapter. One thing about my book you don’t have to read in order, you can jump to negotiations, maybe go back to career planning, and then the leadership. You can say, “I won’t focus on this chapter, one tip from this chapter.”

The other way it can be used and is the future of content. If you’re about to go into a networking event, “What were all those tips Mark gave me?” You’re not going to have my book with you, and you’re not going to say, “I carry this and reread the chapter.” You can open up the app and say, “I’m going to flip through what were those tips quickly. I’m going to search for it. He said something about handshakes. Let me see what he said.” You can open up the app and dive in and get a quick refresher. All of us as content producers are creating content. We sell you dead trees but we’re selling you ideas and putting them in a different useful format is the future publishing.

[bctt tweet=”You can’t force engagement. Instead, you can have a dialogue about why a person is holding back.” via=”no”]

You’re a programmer in the past. Did you create your app? Who do you use to do that?

I contract out to a company I’ve used in the past because the underlying of me writing codes these days is not optimal. I designed it, I patented the app and we’ve got a white label version coming out for other content creators that will come out later. I left it to them to write the actual code.

I’ve always wanted to do more apps. Some of my work is going into other people’s apps but I’ve never done my own. I’m always interested to hear experiences on that. When we were talking about the different groups of how different age groups, different things, and how would apply, when I was writing my book on reinventing your career, I was looking at not the new person out of college but the new person. A lot of people had golden handcuffs and they broke free or a lot of people have found that COVID has changed their concept of what they want to do. How would this book help them?

This can help people throughout their careers. For those who aren’t sure where they want to go, or even mid-career where you’re saying, “I need to change,” particularly as you note we’re seeing after COVID. Chapter one on how to create a career plan. How to figure out what you want to do and create a plan that you can execute to get it is helpful. The other chapters dive into these specific skills. If you want to get better at networking or negotiating, or learning to interview and that’s one. There’s plenty of content and as a candidate, how you answer these questions. Here’s something that surprises me, those of us who are white-collar workers at some point, we’re going to interview other people. Most people have had zero training in how to interview.

We always speak about how hiring the right people is so important and yet we give zero training on how to do that. Whether you want to learn any of these skills, you can jump to that chapter and say, “I’m going to brush up on these skills, I’m going to figure out what’s the approach to it and what are concrete, actionable items I can do.” I want to emphasize that first point because as I’m sure you say in your books at curiosity, you can learn to be curious, you can learn to be a leader, you can learn to be better at networking, all of these skills are learnable. Some of us happen to be inherently better at, some of us are inherently better at sports or music or math. All of us can learn these skills if we read about them and apply these techniques.

I agree with how important that is. The interviewing was interesting to me. When I’m interviewing somebody, I want to know what research they’ve done about my company. When you talk about interview questions, are there some particular questions that you find important?

The most important one is, “Tell me about yourself.” I like to start open-ended. What I’m looking for is less what they say and more their approach. How do they answer that question? Are they giving me a timeline? Are they giving me a story? Are they emphasizing certain points? Are they rambling on for five minutes? Do they have the sense to limit to maybe a 2 or 3-minute introductory answer? Are they tying it into the company or the role? I’m looking in a meta way. I even look at their grammar and word choice. That tells me something about the candidate. I asked a lot of open questions but I’m looking at that meta-level during the interview.

Are there no-win answers like the Star Trek, commonly the Kobayashi Maru? Is there something that we should look out for as being the interviewee?

TTL 844 | Career Toolkit
Career Toolkit: A month after reading a book, you forget 90% of it because you are onto something else in your life.


I don’t think I’ve seen a no-win answer. I suspect if you ever get a question like that where it feels like every option is a bad one, then you want to follow the advice of Captain Kirk and change up the problem and reframe the problem or look at it differently.

A hard one for a lot of people is, “Tell me a time you didn’t get along with somebody.” What’s the right answer for something like that?

As a candidate, anytime you’re being asked about something negative, it’s fine when you deny it, “I’ve never had a problem with a red flag.” You say, “Here’s the problem. Here’s what I tried to do. Perhaps it didn’t work but here’s what I learned from it.” Anytime you’re being asked about something negative or a failure, it’s okay to admit you’re not perfect. The key takeaway is that, “I learned from it, and here’s how I am different.” That tells the interviewer that you’re human and you learn from your mistakes. We know you’re going to make more mistakes. I always tell my team, “It’s fine to make a mistake. Don’t make the same mistake twice.”

That’s such good advice. You were talking about, “It’s okay to be different.” I was looking at some of the stuff you write about. You talk about different types of diversity in hiring. I’m curious what mental diversity is.

Firstly, there’s standard diversity which is great and wonderful and none of this takes away from that. Mental diversity, I distinguish this from a similar term called neurodiversity. One of the trends in hiring is people talking about neurodiversity. The most common example is hiring that Asperger quant person, whose skills are a little off but brilliant. They say, “Great, let’s put them in front of an Excel spreadsheet.” Mental diversity is recognizing that we all think and act differently. I am not surprisingly a very quantitative person in how I approach things. I like numbers and formulas and graphs and charts and I love playing with Excel spreadsheets. There are plenty of people who don’t. One of the things is when I’m engaging with those people, I can’t overwhelm them with numbers and charts. They tune out.

It’s good to have someone like me on the team because if you do quantitative analysis, I’m the guy who’s going to step up and say, “Let me add it.” What I am not good at is that Hollywood pitch is selling that big vision and game everyone inspired about the story in the future we’re going to. Other people are good at crafting that story about thinking that way. You want people who approach the problem from that perspective. As we all bring with our standard diversity, men, women, LGBTQ, we all have different approaches on, “Have you thought about from this angle?” It goes too with our perspective. How do we think about our education and background? Do we look at problems and opportunities differently and bring that in allows for a more diverse set of solutions?

As you’re talking about that, I’m thinking about a company I worked for. They have us take personality tests and we were assigned to colors, red, blue, green, and yellow. You had to put your color and your results on your cubicle so people knew how to interact with you. Red was direct. You didn’t want to bore them with too much detail. They want you to get to the point, they cut you off, they might hurt your feelings. The green was the extrovert who was chatty and would maybe get their feelings hurt by the red if they got cut off thing. The blue was more slow-paced. They don’t like to be rushed, they would be pretty calm unless you push them over the limit, which was hard to do. They would explode if you did.

The yellow was what you described yourself, they want lots of numbers and they read the manuals, and they’re more engineering type of thinking. I never like to categorize people into boxes that much, even though I do a lot of personality assessments, and some of them do that. It was helpful to think like that when you’re interacting with people. Is this person a yellow? Should I be giving them numbers? Should I be showing them in this way? If they’re red, they’re going to be annoyed and cut me off? How do you feel about some of those assessments? Should we be doing that in our heads?

[bctt tweet=”Getting feedback from others gives you a different perspective on your blind spots.” via=”no”]

What you describe sounds like DISC? I know you’ve written about DISC and Myers Briggs.

This one was managed by strings but it’s like DISC in the fact that there are four types. They are slightly different.

I’ve looked at a number of these models. There’s some controversy some people call Myers Briggs astrology for business. What I say in the book is, first, these are tools. If you find the tool useful, great. If you don’t, don’t use it, that’s fine. Any tool or really model is limited in scope. We’re not simply in one of these four categories or whatever level of complexity it does, it doesn’t capture us. If it’s a useful approximation, great. Let’s start with that. Let’s use that. I am a fan of these for the reasons you name, it helps me first start to get an orientation to the person. If I know nothing about you as I walk into your office, I see this I go, “I know you happen to be a green or red, I’m going to start orienting myself that way.” What you have to do is not say, “I have the color done, you have to get to know the person and adapt.” I see the red but I’m also picking up a little blue. I knew how to adjust over time. I happen to be a fan of these tools.

I do like to have that shared with other folks, “This is who I am. This is how to engage with me.” When I joined a new company, I do a larger version of this. When I show up, I sit down with my team. I say, “Here’s who I am. Here’s how you should engage with me,” not here’s how I like to think. You should email me versus catch me in the hallway. I want to see options and then have you recommend one as opposed to giving me the final answer. I try to help people learn how to communicate with me if all of us can do that with these tools and with other techniques. Think about how much better communication will go inside organizations.

It’s interesting because I hadn’t cared about personality tests until I wrote my dissertation on emotional intelligence. When I got certified to give those assessments, I went ahead and got certified or qualified to give the Myers Briggs at the time. A lot of people look at that like that thing. What I found was helpful and interesting about that is they had a big movie about Myers Briggs all of a sudden which was weird timing. They have come back into being super popular in the younger generations. I didn’t recognize that until recently that was happening. What I found helpful in my training was self-assessment.

First of all, I’m always surprised when people are surprised by their results. If you’re self-assessing, you should know what you’ve answered because you’ve answered it. What’s helpful to me is not knowing what I am because I know what I am. What’s helpful to me is understanding the dichotomies and knowing the opposite of what I am. When we did the Myers Briggs training, they would put everybody that was a certain personality type. If you were a thinker versus feeler, the thinkers would be on one side of the room, the feeler would be on the other side of the room.

She would ask a question, “How many of you like to do this?” The whole one side of the room would put their hand up. The rest of us would look at them like, “What? Why would you like that?” It was helpful to me. The thinker versus feeler, the feeling side, they said, “How many of you liked when people bake you and bring you cookies or something?” They all wanted cookies, and I’m like, “I don’t want people to bring me cookies.” I couldn’t imagine why that was such a great thing because I was a high tea.

My personality was so different. I looked at them and I’m like, “Now that I know that if you have these certain qualities, you like people to bake you things or bring you things or do things that I wouldn’t care to do.” That opens up quite a possibility. It was in the interview process when you think about the introvert’s and extrovert’s dichotomy. If I’m an extrovert and I’m interviewing somebody and I asked them a question. If I don’t understand introverts, I might think they’re not listening. They didn’t hear me, they’re stupid, whatever it is, I’m thinking because they didn’t answer fast enough. They need time to respond. Do you get into those kinds of aspects of personality in your training?

TTL 844 | Career Toolkit
Career Toolkit: Many white-collar people will interview other individuals at some point in their career, but most of them have had zero training in doing so.


We do in the class I taught briefly in the book. The other way it talks about using these tools is for personal development. Years ago, I did I’ve done a number of these tests and I had done the Herrmann Brain Dominance Instrument. I was extremely quantitative. Anyone who knows me would not be shocked by that. When we do this at MIT, we skew slightly towards quantitative but we are not all in that area. We’re fairly balanced across all quadrants. We’re not the stereotypical people. I was extremely literally off the charts for quantitative. I was weak in my interpersonal aspect and interpersonal quadrate, which also probably wasn’t surprising. I never thought about it because I never thought about interpersonal skills, think qualitatively. When you use this tool, when you recognize, “Here are my preferences.” These are preferences. This isn’t the SAT’s it’s not a skill assessment. It’s a preference assessment. Preferences become habits and habits become strengths.

I like quantitative things. I used to do Math problems for fun as a kid. I would play chess and I got good at doing quantitative things. I did not like things that involved good EQ. Working on those EQ skills I wasn’t good at, I avoided it like I avoided playing Ice Hockey. I’m not good at either. If I want to get better at Ice Hockey, I start practicing if I want to get better, I have recognized, “Here’s my shortcoming.” I do need to get better at those interpersonal skills, I do need to get better at doing those Hollywood pitches. In those categories, I said, “Let me create a plan for how I’m going to strengthen those skills.” I’m never going to be the best in the world at them but I am picking them up so I am less weak and even moderately strong in some of those categories. We can also use these tools to recognize areas where we haven’t focused as much as a weakness for us.

I talk a lot in my courses about some of this stuff. The introvert-extrovert thing, I have the students read Susan Cain’s book Quiet because that’s a helpful book. I’ve had Tom Rath, talking about StrengthsFinder. That’s an interesting thing that you brought up. Do you focus on your strengths? Do you try to develop your weaknesses? There’s some debate on that one. I always had my students do personal SWOT analysis when I was teaching courses that dealt with careers. I taught a marketing course where they had to market themselves through the semester. Part of it was creating their SWOT analysis and determining how they’re going to get a job by the end of the year, they had to market themselves. How much do you focus on your weaknesses versus your strengths?

It depends on what we define as a strength or weakness. In general, I am a believer in weaknesses. Let me illustrate with an example. This will involve a little bit of math that comes from my friend, Professor Charles Lazarus at MIT. We’re going to do sixth-grade math. Imagine you have a rectangle that’s 4×10. You need to increase one of the sides by two units and you want to maximize the area. Do you increase the long side going from 10 to 12 or do you increase the short side going 4 to 6? We want to increase the short side, 6 times 10 gives us 60. We had a math refresher, why am I talking about this? What happens when you increase that short side or you go from 4 to 6, you’re adding two units. Those two units are amplified by that long side when we think about this in terms of skills.

Imagine someone who is a genius, incredibly talented in some particular area but this person is nasty. You don’t get along with that, no one gets along with him. This person is incredibly shy and doesn’t have a strong network, no one is aware of these skills. This person is a terrible communicator who is all garbled and they’ve brilliant ideas but no one has the patience to listen to him, instead of investing more in trying to get even better in his area of expertise. He took some of that time, let’s say the 40 hours a year, we invest in improving your skills and put ten of them into communicating better. Ten of them into building a better network or being easier to work with. All of a sudden, you’re going to get a much better return on investment. You’re going to take that long side of that skill that you have and make it more applicable in the workplace. We all need to recognize there are short sides and long sides to us. There’s more than one of each. We have to work on some of those short sides to get the most out of our long sides.

I believe you and what you’re saying is important because it’s not all about strings. We have to consider some of the things. In my research was to look at some of the weaknesses. What I study is the value of curiosity. I went out there looking for assessments to figure out how to measure this. I’m a very quantifiable type of person too. I want to quantify things. The only thing they did was tell you if you’re curious, higher low levels and then I’m like, “If you’re low then what do you do?”

I tried to figure out what keeps us from being curious. You could look at that as a weakness but I look at it as something that’s shaped us into the things I found as fear, assumptions, technology, and environment, limit our curiosity. Once you can focus on the things that have held you back then you can develop them and turn them into things you would like to do. I was thinking of my conversation with Daniel Goleman on emotional intelligence. He felt that the best way to get a real true reading was to get a 360 evaluation. It’s the same thing if you’re getting input that you hadn’t looked at before. You can look at it as a weakness or as a new opportunity.

Getting input from one of these assessments or whether it’s from that 360 reviews, getting feedback from others, gives us a different perspective because we have blind spots when it comes to ourselves. That can help us identify those blind spots and work out to strengthen those short sides.

[bctt tweet=”Many of the best leaders get where they currently are because they began in the trenches.” via=”no”]

In your book, you write that people can practice leadership every day. I teach a few courses where we talk about the difference between leading leaders and managers and you touch on some of this. I was hoping you would address that because I do play a lot of these clips in my courses where I’ll ask them, how do you differentiate between a leader and a manager? What did you write about in that respect?

My favorite quote to distinguish it I put in the book is, “No one ever managed men into battle.” That captures it. In the book, I break it down into three chapters, one on leadership, one on management focusing on the people aspect, and one on management focusing on the process aspect. I’m not promoting Six Sigma or Agile or a particular process, I’m looking at some of the fundamental components. I wanted to break it down this way in a very much wax on wax off, let’s get to the fundamentals. When I conclude that section, I point out, most managers lead, most leaders manage, you’re going to do a combination of the two. It’s important to understand what are the different aspects. I would always encourage folks to develop both sets of skills because they do go together. All the skills in the book, the reason I put all these together because there are books on leadership and negotiations. I want to put them all in the book because these skills intertwine and even reinforce each other.

I have a lot of students say, “Leaders are more strategic and managers are more tactical.” How do you develop that strategic thinking?

I would say to a first-order that is certainly true, that the leaders are looking at that big picture strategy. That strategy comes from curiosity as a big piece of it because it’s learning, listening, and watching. My model of intelligence is based on pattern recognition. As you look at other types of strategic challenges, I’m using strategy here in a very general way. It’s, in general, larger problems. What are the different ways we can solve this? What are other things people solve? You’re going to start to recognize patterns and opportunities. The reason I came up with the app was that I had worked in digital media in the past. It has nothing to do with an app, nothing to do with promoting a book but I saw them and said, “I think there’s a similar pattern here.” I saw an opportunity to change how we create and market our content as authors. It’s that pattern recognition. If you want to work on the strategy part of leadership, that is spending a lot of time listening, learning, and digesting what you’re taking in.

I’m thinking about a leader I had, who was having great ideas, everything was an idea but he never did anything he had everybody else do it. Is that a good thing for a leader to not implement to have everybody else do it and come up with the ideas? Do you have a combination of that?

It depends. If you are the President of the United States, you are not an implementer. You are setting that vision and strategy. Jamie Diamond of JP Morgan, I don’t think he gets into the trenches much. Certain types of roles, larger organizations, yes. Smaller ones, the startup, and midsize companies on that, as the CEO you still have to, “We got to close this account. I’m going out there. I’m going to make it happen.” We’re stuck on this, “Let me roll up my sleeves and figure out what’s happening here.” Many of the best leaders get there because they began in the trenches.

When you look at Martin Luther King, he led a movement that changed America but he didn’t start out leading this large countrywide movement. He started out doing small local activities by saying, what are the challenges? What are the problems? How do we need to do this? Understand the tactics, the management, he had a good concept and didn’t come up with, “Here’s where we need to go.” The details ask for someone else to figure out, he understood it. The best leaders did come up through the trenches and have a sense of practically speaking, what are we going to face when doing this?

I teach a course where we discuss the value of charisma to leadership and I have students give me examples of how charisma has led to successful leaders and maybe they’ve used it negative ways and they always bring up Martin Luther King Jr. as a positive example and Hitler is a negative one. How important is the charisma of being a successful leader?

TTL 844 | Career Toolkit
The Charisma Myth: How Anyone Can Master the Art and Science of Personal Magnetism

I think it helps a lot. Charisma, it’s another skill. Some people are naturally charismatic, and they are but you can learn it. My friend Olivia Fox Cabane wrote a wonderful book, The Charisma Myth which can teach you to be charismatic and it certainly helped me. As a leader, you need to be inspirational. You need to put out the vision, the future state you want to get to and convince people to follow you in getting to that goal. If you’re not charismatic, it’s going to be a harder approach.

It’s also helpful for someone like me, I very much want to see what’s the plan, what the numbers are like, that’s a great idea. I’m not convinced until I see something concrete. For other folks, they want to say charisma, and for most people, when you are leading, you have to get that emotional connection. If you have a plan, it’s not enough. The emotional connection without a plan for people like me is not enough. The plan without the emotional connection for most people, that’s not going to work. You start with the emotional connection that comes from charisma and then back it up with some of these other components.

I met so many people who plan the plan to plan the plan and never do anything but plan. You see that in meetings. “Now, we’re going to talk about the minutes from the last meeting, and then the next meeting, we’re going to talk about this.” Nothing happens beyond that. How do you get out of that?

That was a challenge that we faced when I was working at SUNY, State University of New York back during the Great Recession. We were helping people who lost their jobs. We’re trying to find them new ones. The job losses back then were coming from large corporations. In New York, in particular, we had lots of people from these large financial service companies. The job creation was happening in these tiny startups. We faced the problem that people had that planning to have the pre-meeting, to plan the meeting, for the meeting, at a startup. You turn around and say, “Bob, I’m thinking we should do this.” Bob says, “Sounds good.” That was six months of meetings. It comes down to changing the mindset and understanding what and why.

When I worked at Sears, is consulted as they built our labor marketplace. Sears is a company that got sued every day of the week. You’d have product liability, a slip, and a fall. These weren’t major lawsuits. I don’t want to paint Sears as a horrible company. They’re used to being sued. They had a large legal team and everything was thinking about, “How do we make sure we minimize how much we get sued or liability?” At my startup companies, we’re not worried about getting sued, no one’s going to sue us for one thing, we’re broke. Rule one is only a few people have money. That’s not an issue that we focus on. Once we get larger, once we start doing $50 million revenue, let’s start thinking about people who are going to come to us. We have to change the mentality.

When you’re going from these organizations that are all about planning, there is a reason they are that way. They perhaps have things to protect. They have a process for a reason because without that process, things go wrong and you get bad consequences. When you’re in a different organization or a different part of that organization, then you might want to behave differently. I was brought in to help them do a startup inside the company.

We wanted to do it where let’s move fast and break things. That’s how you succeed in a startup. At times we bumped up against this other culture. Both cultures are good, that six months of planning do make sense. NASA rocket launches took them six months to change a single line of code. That does not work for most startups, even most companies. Given what was on the line, the lives and program risk, it made sense. You have to recognize what the organization is. What are the risks and the payoff? Have the right process to work for that.

A lot of people are on Zoom meeting after Zoom meeting. Every day somebody is telling me, “They do eight hours of Zoom meetings and then they’re expected to do their work after hours.” What do you say to companies who expect that?

[bctt tweet=”A manager must make sure the right people have the right conversations at the right time.” via=”no”]

I have a whole write-up on meetings in the process section of management. As most people do, I think they get far too abused. Ultimately, as we think about working in the 21st century, many of us live in a digital world. In the old days, you go back to the Industrial Revolution. We were creating physical goods and physical products. We are creating digital goods and digital products even if we only manufacture something and sell some physical goods. It’s all being controlled by digital information.

Companies need to focus on the management of digital information. As a manager, our job is to make sure the right people have the right conversations at the right time. That’s the essence of management. This can be done by standing in the hallway, by email, instant messaging, or meetings. As a manager, you need to think through what is the information flow and then create the appropriate structures, typically meetings but also email lists or processes about what to announce how to whom. If you look at your meetings through that lens, you can start to figure out whether all these meetings are helping you or impeding you.

A lot of them complain that the meetings could have been handled in one email, and yet we wasted an hour, “You could just send an email and then we’re done.” I’ve had people read me their email and read it in this snarky tone and I’m like, “I don’t hear that because I don’t know the backstory.” Sometimes, you’re getting miscommunication if it’s in written form. Do you find that’s a challenge for a lot of people?

It is and I also speak about in the book, recognizing each channel has a certain amount of bandwidth. In an email, for example, you might include pictures, you’re less likely to include pictures by texting, and certainly, by phone, you’re not going to include pictures. On the other hand, you get the tone of voice. With instant messaging, as opposed to email. Some people who know each other well can get a sense of mood by how they’re responding, the speed of the response, and a few other subtle things that don’t come through easily in an email.

We need to recognize the limitations and benefits of each channel are. It goes back to how do we use each of these tools? Emails are tools, meetings are a tool, and instant messaging is a tool. How do we use each of these tools to best foster that flow of information? Once we start with thinking through the information flow, we can apply each and having clear rules. The other problem in companies, sometimes it’s an email, it’s a meeting, it’s on instant messaging. Let’s be clear about when all of us are going to use each tool for what purpose.

In some of the first courses, we taught netiquette. That was how do you speak in a way that’s a proper and online course, and that type of thing. One thing that always surprises me is some of the emails you would get from people that I used to work with who would send Warren Piece emails in 3 or 4 a day. You’d respond with, “Thank you,” or something really quick. Trying to get the hint that maybe I don’t have time to read four pages four times a day of this stuff. How do you get those people to get the clue that they can be more succinct?

This goes back to two of our points. The first is about introversion extroversion or entail diversity. Some people would much rather write and send an email, especially introverts who want to, “Instead of the meeting, I’ll sit here and think through this instead of being put on the spot to have to respond at the moment.” That might be a preference that someone has. The other is the use of tools. For some people, particularly if they come from an environment, maybe at their prior company, emails were the way to go. That’s not true at this company. There are no explicit rules and so by default, this is their learned behavior. This is why we need to be explicit about how we want to use each of these tools. We want to recognize that we all have our preferences which may or may not align with the preferences of other people.

That’s such a good point. I guess I should have been clearer. The type of things I was talking about is people chatting more and not giving any value to what’s happening in the working world but look at my emails. I’ve seen people who do a lot of that. They need congratulations or whatever from people that weren’t even their leaders at all. I’ve seen people copy and paste the same content to twenty people on the same day. They fill up their email box. How do you deal with those kinds of situations?

TTL 844 | Career Toolkit
Career Toolkit: Anytime you’re being asked about something negative, it’s okay to admit you’re not perfect. The key takeaway is that you learned from it.


You’re referring to the less work-related email.

They’re not. This isn’t something we’re working on together. It’s like, “Look what I’ve done. I’m busy doing this and this.” It has nothing to do with work.

Potentially work-related not relevant. This goes to what I speak about in chapter two, which relates to politics. A lot of that was influenced by a great book by Seldman and Brandon called Survival of the Savvy. People have different political approaches. I happen to be a less political person. I am very much heads down, do my work, and let the results speak for themselves. Other people who tend to be on the more political side of the spectrum are a lot more relationship-focused and making sure they are visible in their achievements.

I’m not saying they are bad, extreme people on one side or another could be extreme political people who backstab you. Some folks take more of a relationship and communication-oriented approach while others take to get the right best answer and let it speak for itself. It could be a difference in perception of style. What I have to do is make sure people are aware of what I’m working on because that’s their preference. They grew up going to some organizations in which that was encouraged and rewarded. We have to be explicit about what the norms are, and how we’re going to use these tools, and where it’s inbound and outbound.

Its expectations are so important and poor communication costs so much money. Anything that you can do as a leader to make that clear, it’s critical. I could ask you a million more questions, but we’re out of time. I love all the types of things that you cover in your book and I think many people can get so much value from this. If somebody wanted to follow you or find your book, do you have a link or something you’d like to share?

You can go to my website, You can learn more about the book, download the free app for Android or iPhone. You can go to the resources page, where it lists lots of other great books and resources, including a free download of how you can create these peer learning groups at your organization. All of this is available at the website

It’s a great book. Thank you, Mark. Many people can benefit from this. I enjoyed our conversation.

Thanks for having me. I’ve enjoyed it as well. 

You’re welcome.

I’d like to thank Mark. He’s just a great guest. We’ve had so many great guests on this show. If you’ve missed any past episodes, please go to You can read them on the blog if you want to listen to him there as well as on am FM stations and podcasts were everywhere. Hope you take some time to check them out.

Important Links:

About Mark Herschberg

TTL 844 | Career Toolkit

From tracking criminals and terrorists on the dark web to creating marketplaces and new authentication systems, Mark Herschberg has spent his career launching and developing new ventures at startups and Fortune 500s and in academia. He helped to start the Undergraduate Practice Opportunities Program, dubbed MIT’s “career success accelerator,” where he teaches annually. At MIT, he received a B.S. in physics, a B.S. in electrical engineering & computer science, and a M.Eng. in electrical engineering & computer science, focusing on cryptography. At Harvard Business School, Mark helped create a platform used to teach finance at prominent business schools. He also works with many non-profits, including Techie Youth and Plant A Million Corals. He was one of the top-ranked ballroom dancers in the country and now lives in New York City, where he is known for his social gatherings, including his annual Halloween party, as well as his diverse cufflink collection.

Love the show? Subscribe, rate, review, and share!

Join the Take The Lead community today:

Leave a Reply

Your email address will not be published. Required fields are marked *