Organizations consist of different types of leaders because every enterprise has different cultures and needs to cater to. In addition to that, various skills are needed for a leader to be effective and execute strategies that would drive change. In this episode, Ben Baker sits down with Mark Herschberg for a conversation revolving around the future of leadership and excellent communication within the organization. Mark Herschberg is the author of The Career Toolkit: Essential Skills for Success That No One Taught You. He talks about leadership skills such as networking, interpersonal dynamics, ethics, negotiating, communicating, and planning. Dive into this and learn the ultimate guidelines for you to unleash the leader within and develop the fundamental skills you are meant to have.
Welcome back, my wonderful audience. Thank you for coming back, sharing my stuff, reading, downloading and everything that you guys do. I appreciate all that you do and how engaged you are as an audience. Keep on giving me those comments on LinkedIn @YourBrandMarketing. I love having you guys join me. In this episode, I have Mark Herschberg. He is the author of The Career Toolkit, an MIT instructor and a fractional CTO. We're going to talk about the future of leadership because we're about to reset and move forward and we need to be able to talk about this. Mark, welcome to the show.
Thanks for having me. It's a pleasure to be here.
I've been looking forward to this. We have been talking about this. I'm blessed enough to have guests lined up but I always like to make sure that I get good guests. I was asked, “Do you do know Mark?” I said, “I don't know Mark.” You and I had an initial conversation and we hit it off. I love what you talked about. I love your passion and the energy that you bring. I said we got to get you up on the show. Thanks for being part of the show. Let's start by getting the audience an idea of who you are, where did you come from and what brought you to where you are now.
I began my career as a software developer back in the 1990s in the dot-com era and I realized I wanted to become a CTO. To get that job, it wasn't about being a good programmer. There were all these other skills I needed, such as leadership, communication, negotiation, team building and no one ever taught me these skills so I had to start to figure it out for myself. As I developed them in myself, I realized these skills aren't just for people at the top level. It’s not just for the C-Suite. All of us can benefit from these skills. I wanted to hire people with them but I couldn’t find others who have these skills they weren't taught either. I had to develop them in my teams. I put together some internal training programs.
Shortly after doing this, MIT had been getting similar feedback. Corporate America said, “We love your students. They're incredibly smart and educated but we wish they have some of these other skills such as leadership, communication and team building.” This is not just true for MIT students but colleges across the US have gotten similar feedback. These are the skills companies want but they can't find. At MIT, we put together a program. We refer to it as the career success accelerator. I helped build that program initially and I've been teaching there for more than twenty years. Knowing that these skills can help everyone, not just our students, is what led me to put out the book, The Career Toolkit: Essential Skills for Success That No One Taught You.
It's true because time after time, you see people come into the workforce and they're extremely smart but they have no idea how to lead. They have no idea how to get the best out of people, communicate, be empathetic, listen and coach or mentor people. It's skills that are not taught in the school system. A lot of people don't have that skillset being taught at home and they don't have role models that can do this for them. It's important because I'm a big believer that leadership is a mindset and not a job title.
There are too many people out there coming out of university and say, “I deserve to be a manager.” “I deserve to be a director.” “I deserve to be a vice president,” without understanding what it takes to be great at any of those things. What I want to talk about is what are the skills that you see that are necessary moving forward? How has COVID created a reset? Where are we now and where do you think we're going to need to go?
I selected ten of the most critical skills, the ones we see over and over again. These aren't the only ones but the ten most important. I break them into three sections. They're each in a chapter in my book. The first section is on careers. How to create a career plan? How to figure out where you want to go in your career journey? Create a plan for it and then execute. The second is office skills, managing your manager, understanding corporate culture and corporate politics because an effective person who trips up on this is not going to go far.
The third is a surprising one, interviewing. We all know about interviewing and there's lots of content but we teach people how to be a candidate. I have met many executives who have hired many people and they've had zero training on how to interview or hire someone. If we claim that people are our most important asset, why are we not investing in how we attract and measure that asset as we bring them in? That's the first section.
Second, leadership and management. I break down management to the people management and then the tactical process management. Here, we go to the fundamentals and the skills that people can use from day one. It's not just for people with a leadership or management title. It's the basics of how to interact with other people. The third section is interpersonal dynamics, communication, negotiating, networking and ethics. These are the skills companies keep asking for and those are the ones we need to develop in ourselves and our teams.
Let's try to break those down. We may not go through all ten of them but what dawned on me is the fact that you're right. A lot of leaders, when they sit down in an interview, have no idea how to interview a candidate. They don't know what they're looking for. They have this gut feeling but that's about it. It's a matter of sitting there going, “What does good look like and what does great look like?” What are we trying to achieve as an organization? How do we as people learn the skills that it takes to be a good interviewer, be able to listen, be able to go get that beyond that fluff and get beyond that resume information? Find out more about the human being and say, “Is this human being going to be an asset for our organization? Are they going to be a hindrance?”
This is an example of in the land of the blind, the one-eyed man is king. You do not have a far journey to go. Putting in a little effort already puts you ahead of most other organizations. It begins by thinking about, “What is this job?” When we write job descriptions, we typically create a long list of, “Here's the knowledge or the skills that we want to see.” It’s certainly important. Keep that but think about a few things. First, how much of each of these? Every task that this person does is not done equally. You could imagine two jobs.If we claim that people are our most important asset, why are we not investing in how we attract and measure that asset as we bring them in? Click To Tweet
For example, let's take a director of marketing job. They might be responsible for social media marketing, event marketing and lead generation. At some companies, it might be 1/3, 1/3, 1/3. At some companies, that might be 80/10/10. Recognize there's some weighting or some value metric to each of the things that you need and they're not all equal. If someone's equally good at all three, that's great for that first job and that's what you want. If you're in that 80/10/10 case, find the person who's strong in the 80. If they're not so great at the 10, maybe that's okay. Maybe we can hire other people to the team or learn it. Think about what matters.
We also want to focus on values and attributes. This is where we generally leave it off other than to say strong leadership and communication skills. First, that's a pet peeve of mine. What does that mean? There are lots of different types of leaders. There are growth leaders, turnaround leaders, leaders who can inspire a team and leaders who are like, “I'm going to roll my sleeves and be hands-on.” What type of leader do you need for this role?
Maybe you need someone who is a good negotiator or a good politicker who can help get different coalitions all aligned. That might be important to the job or not to find these attributes. Once you have all of them listed, we know how to say, “You need knowledge of this particular skill or tool.” Ask questions about it in an interview. When you decide that you need someone good at coalition building, great, that's important. Now it’s like, “How am I going to elicit that? What types of questions or evaluation will we use to do it?” By being a little more conscious in our hiring, we can do significantly better.
This is where a lot of leaders and a lot of people who interview fall because they don't sit there and say, “What do we truly need?” More than 25 years ago, I got hired into a company. What I didn't realize at the time is they needed a turnaround transitional person. They were bringing me in to be that turnaround transitional person. They wanted me to break everything, make a mess, fix it and then they wanted me gone but they never articulated that. What they did is they came to me with a whole set of objectives and a whole bunch of things but what they wanted me to do was to break things, fix it and be able to move forward.
If they had come to me with that objective, I would have said, “If normally you would have paid me X, you pay me X plus 20%. The understanding is I'm going to be here for 24 months.” I'm good with that. A lot of companies are afraid to have that conversation with people and say, “This is what we truly need. We have this particular problem and we need this particular skill that's going to enable us to do this for this amount of time. Can you do that job?” That's where we get into the fractional world, where it might be better not to hire an employee but also to hire somebody who is a fractional person, somebody that you bring in on contract. I'd love to know your thoughts on that.
We have to be honest with each other. It's like when you get into a relationship. If you're dating someone and someone wants kids and someone doesn't, it might be a great relationship but there is a fundamental problem. Have that conversation sooner rather than later and either resolve, “One of us will change or we're wasting our time here.” The same thing during that interview process, be clear about what this is. Be honest about, “Here's the job.” If the job involves, “There are some difficult people here or we're in a difficult position,” be honest upfront because you don't want that employee to show up and then suddenly find they were sold a bill of goods. If you're honest, some people love the challenge.
As a candidate, we can do this, too. I had a large media conglomerate try to hire me to be the head technology officer in their business division. This is an old-school, well-known media company. After a couple of rounds, I said clearly to them, “I tend to be a startup person and I've helped Fortune 100s do certain technical initiatives. I can do it here but I want to warn you, I will be a bull in a china shop. I'm going to go in. I don't have patience for red tape that serves no other purpose. I'm going to break things and move things. I will make a lot of changes and move you forward but I might ruffle feathers for a conservative company that likes to do everything in triplicate. You need to decide, is that a fit for your culture? If that's what you want, I'm happy to do it. I'll fight those fights and I'll get bruised. If that's not right, it's not going to be good for either of us to bring me in.” Candidates and companies both need to be honest about who we are and what we bring to the table.
It's knowing who we are, not just as organizations but as individuals. Knowing as a leader, “If I hire somebody underneath me who is a maverick, somebody who's a rule-breaker, someone who is going to push boundaries and stuff like that, that's not something that I can deal with.” You shouldn't hire that person and vice versa. If you are a person who wants to come in and break the rules and challenge, you need to be honest and open when you're coming into an organization to say that.
We are all leaders in our own space when we can be open and honest to say, “This is who I am. This is what I do. This is what I don't do. This is what I'm good at. This is what I'm not good at,” and be able to own it all. With that conversation, you become far more valuable and far more trusted. It enables you to be better at what you do. We start talking about the second layer, technical leadership versus emotional leadership. I call it human leadership versus technical leadership. How do you make sure that people have the right combination? Nowadays, you need to have some level of technology and understanding of technology to be a leader. It's almost a given unless you are in an absolute rudimentary business. I can't even think of one that wouldn't require some level of technology. How do you get people to be comfortable in both roles?
We need to recognize the development of these skills is different in those different aspects. The first side, the technical. By technical, that both means technologies and tools but even the mechanics. If you need to go learn Six Sigma, you get sent to a class. They say, “Here's the Six Sigma process. Here are the terms. Here's the methodology.” You sit there, write down notes and memorize them then you've learned it. That is knowledge transfer. It's how we've learned throughout most of our lives. We sat in school and the teacher said, “Learn this. Here are your multiplication tables. Here are the dates of the American Revolution.” Memorize it and learn it.
The way we learn what you're calling the emotional part of it, that is a different type of learning because there is no formula for leadership. There are no three steps to remember to all of a sudden always be able to communicate. These are complex, subtle areas, subtle skills. The way we teach them at MIT and the way they're taught at top business schools is through peer learning. We sit in a group and we talk about some situations. As we talk about it, you're going to tell me how you might approach it. I'm going to explain how I might approach it and then we realize, “Ben, that's an interesting idea. I would never have thought of that. Maybe I can adapt that to my own type of leadership.” I might say, “It's not for me but I have a deeper understanding seeing how you understand it and approach it.” You can implement this yourself in your organizations.
For too long, we've said, “Let's take our top 5 or 10 people, whatever the budget allows and send them to a two-day training course.” You come back and now you're a leader. Perfect. It doesn't work that way. It's not like, “Here are the three things to remember. By the way, at 2:37 next Tuesday, be sure to apply this.” “I know when to apply Six Sigma.” You go, “Here's the process.” “What do we do?” “Six Sigma says do this.” Here's the obvious, now do the leadership thing, now you don't.We can do significantly better by being a little more conscious and careful in our hiring. Click To Tweet
What we want to do is create these ongoing peer learning groups. You can create groups in your organization. You can do small groups of 6 to 8 people. There are ways to scale it up if you want to do larger groups of 20, 30, 50-plus people. Within this group, you take some content, read it and discuss it. If you want to use my book, you can chop it up into little pieces. I have a breakdown. You read these ten pages and then you come together and talk about it. If you don't want to use my book, you certainly don't need to. You can take other books that you like. You can take articles, webinars or a great show like this one. Have the group listen to it every week and then discuss these topics because it's depth discussion. That's where you're going to get the richness and the learning.
By doing this, a number of things happen. First, you're going to train up your team. When I say team, this isn't just for managers or executives. This is for everybody. Instead of taking those top five people and saying, “You're the lucky one,” everyone gets this training. There is a near-zero cost. Maybe you buy a book or maybe you don't. There's not a lot of cost to it. You're also increasing your employee engagement. Especially as you have people remote and semi-remote, this gets people together. In fact, if you mix it up with people from different groups, you're going to increase internal relationships and networking. Finally, what you're doing is creating a common language because everyone will have read that article or read that book. They can reference, “It's like the Hedgehog model,” because everyone's read Good to Great. They go, “Hedgehog. Got it.”
It's a common language within the organization.
You get all these great benefits from creating a peer learning group internal to your organization.
It's funny because we do similar things. I have the Developing the Leader in YOU course, which years ago was a two-day course that I came in. I beat the leaders up for two days and then left. I realized it was absolutely useless because on day three, 70% of that information was gone. It was outside of their head. They had no ability to apply it. They had no ability to do that. What we did is we turn that into case studies that ended up being, “On a monthly basis, Ben's going to have a Zoom call with you. We're going to talk about it and we're going to figure out, where are you today? How have you applied it? What are the challenges you face? Here's some information. We're going to talk about it next month when I come back.” We've been able to convert that into an online process.
It's that ongoing communication, learning groups and figuring things out together that not only builds better leaders but it builds better cultures and teams and it creates more symbiosis within organizations. It allows organizations to understand what the goals are, how people fit into those goals and how they're important for everything moving forward. Let's talk about the 3rd part of that you were talking about and you're going to have to remind me because we've gone through the 1st and 2nd sections. What was the third section? Let's get into that.
The third section is communication, negotiation, networking and ethics.
Of those, where is the best place to focus? They're all important. For me, it's communication. I always start with communication. I find that people communicate poorly. It's something that you could always get better at because if people don't communicate well and people don't understand well, goals don't get achieved and leadership breaks down. There are all sorts of things. Where do you see as the secret sauce that helps leaders become better?
All of these skills build upon each other. Great leaders know how to negotiate, great negotiators know how to communicate and good communicators have an extensive network where they get different types of ideas and understanding. They all build on each other. Particularly for the time we're coming into as we go into the new normal, whatever phase we're on, of the semi-remote workforce, communication is going to be a key issue for us to focus on. When we were all in the office, there was a natural communication that happened. We could replicate the meetings. We've sat on Zoom and we've had the calls and go, “This is a meeting.”
It’s that other communication, the communication that happens from the watercooler conversations, going to get coffee together. It's a communication of you walking into the office, “Why does everyone seem upset? Something's going on.” You can feel the energy. You don't get that when you're remote. Now we're going to likely be semi-remote but still, that vibe is going to be different. All of us need to be conscious about this. It is important for us as managers. The essence of management is making sure the right people have the right conversations at the right time. It is managing information flow. Some of that might be formerly, “We're going to meet every Monday and get a status update,” but some of it might be, “Are you aware this key partner is not happy and we might lose that partner?” That might not be in a formal meeting that might be you walk in. Why all the long faces as you're walking past a cubicle?
That cubicle is empty.
“Something happened here.” Making sure we get that information flow that happens in-office, out-of-office, that happens to the right people no matter where they are. This is important. We have to be a little more conscious about it in this new type of workforce.When there's a fundamental problem, you have to have a conversation with your people sooner rather than later to resolve it quickly. Click To Tweet
Let's talk about that. This is the new normal, new to the third level that we're getting into. A few years ago, we sent everybody home with a lick and a prayer and hope and promise. Few of us knew what we were doing. We probably didn't have the Microsoft Teams set up and do a Zoom call properly. We probably didn't even send people home with all the stuff that they needed from their desks. We've built systems and processes and did things out of necessity. A lot of it done was done with duct tape, Scotch tape and Band-Aids. It's time that those Band-Aids and duct tape get ripped off.
We have to go back to a point where we're saying, “Good enough is not good enough anymore. We need to build new processes to be able to move the company forward and be able to understand how we're going to succeed moving forward.” Where do we go from here? Where do we go as leaders not only to become more effective leaders within this hybrid world environment but also to build that next generation of leaders and to enable teams to succeed? We need to be more resilient, adaptable and creative.
Lots to unpack in those set of questions. It begins by thinking about management. It’s completely different than leadership but management is about making sure the right people have the right conversations at the right time. It’s starting with that. A common mistake I see working in technology is people say, “Here's some software. We're going to buy the software. We're going to have to change how we work to fit into the software.” You should never change how you work for the tool. You should make the tool work into your process. This assumes you consciously thought about and made the best process for you.
Make sure to take this time to reset and say, “Going forward, what is the right process?” By process, this could be anything from how we communicate in our little team of five to how the company handles its entire logistics and supply chain. Think about the right process, information and physical movement of things. What's the right process? Create the systems to optimize for that. By systems, it might be the software you buy, it might be your meeting cadence, when you're going to use email versus Slack versus phone calls when you're going to be in the office versus out.
If you know you have a crunch at the end of every month then set your cadence of, “We're always in the office the last week of every month. That's the time for us to be together. Other times, not as critical.” Make sure that your processes reflect what your business process is. You also noted that we put things together with spinning duct tape. That was totally acceptable because that's where we were in the world. Our customers, suppliers and partners all understood because they're doing the same thing. They’re like, “No worries.” “You forgot to send me that. We'll figure it out.” This is where we need to say, “Let's replace it with something stronger. Let's build it with concrete. Let's do the right thing.”
In technology, we talked about tech debt. We often are like, “We got to get this out so let's quickly hack this together.” We know it’s been duct tape. It's not going to work long-term but it's good enough for the release. You have to pay down that debt at some point. This is when we have to do it. Unfortunately, what happens with tech debt is going to happen here. The CEO is going to say, “Great. We're all back in the office. It’s been a crazy time. Great job, everyone, for getting us through it. Now we have all these new initiatives, quick run forward. Don't worry about what the duct tape is holding. Run forward and run fast. We have all these quarterly goals we have to hit and we're not going to do what we need to do. Try to put into your operations a certain amount of time per month or per quarter where you're going to be replacing each of the strands of duct tape with something stronger.”
Would you assign that duct tape role to a person or a team? I'm sure you're going to say whether you’re a team of 25, 2,500 or 25,000. There needs to be somebody that has ownership of saying, “This is where we are today and this is where we're going.” Be able to take a look at those systems and the processes and be able to build that cement structure. How would you, as a senior leader, find that person? Is it a cross-pollination of different departments? Is it an individual person that acts as a czar? Let's pick a 1,000-person company and go from there in terms of moving forward.
The answer is always it depends. What are some of the factors? What do you want to think about? This comes right from the top. This should be all senior leaders. First, have a real heart to heart with yourself, the other leaders and your team. “What is the process we should have going forward.” Make sure that it's clear because if you don't have a clear process, whatever you're doing, it's wrong. When you're pouring the concrete and you don't have clear blueprints, you're not going to like the house you wind up with.
Your foundation is going to be in the wrong place.
Make sure you are clear on this process going forward. Start from scratch. Forget what you're doing now. Forget what you did before the pandemic and say, “Going forward, what does this need to look like?” Start with that clean whiteboard and build it from scratch. It might look similar to what you have now and that's fine but you don't want to be a constraint. I would set a timeline. Maybe it's 3 or 6 months. If you're a large company, maybe it is a year. Have that timeline for where you define your processes. We know this isn't set forever. It will evolve but you want to be evolutionary and not like, “We completely built this wrong.” Add that addition to your house. Not, “We can't even build on this land.”
Once that is clear then you say, “Part of our task is we have to build out this partnership and up our production,” whatever your metrics are on that monthly, quarterly report. You probably have something where you present, “Here's how we're doing each of the projects.” One of those projects should be, “How are we doing on replacing the duct tape and building the appropriate infrastructure?” That should be visible to every one project where you have clear progress and someone is the owner. That's probably the senior leader, the manager of the department. They might assign someone else to be dealing with it day-to-day and they might have 100% responsibility and their job depends on it. As the manager, department owner, senior leader, you still need on your project list and you need to be evaluated on that. Your bonus part of it needs to be tied to that like any other project. You don't want to be an afterthought. You want to be a first-class project like everything else you do.
It's not off the side of your desktop project. It's got to be something that is like, “This is mission-critical like every other piece that you're working on.” It's got to be something that sits there going, “No, we've got twelve projects going on. This is 1 of 13,” not, “It's an afterthought.”Excellent leadership is recognizing the skills that are necessary in moving forward. Click To Tweet
Otherwise, it always gets pushed to tomorrow. It's like we see with software with tech debt, eventually, it's going to come up and hit you where you're trying to do the next project. You can't support that next thing because you never build that solid foundation.
Let's talk about what are the skills that you think that leaders need to be focusing on in order to be successful moving forward?
It is all the skills we spoke about. Learning how to interview effectively gets you the right people, which is the basis of having an effective team. Learning how to communicate effectively to build those relationships inside the organization, in your larger ecosystem and industry. In general, building out an extensive network is important. Knowing how to communicate within your team, your department and with others in the world at large is a critical skill. Learning how to lead, how to deal with corporate politics and learning how to fit into the corporate culture, which might be changing. What worked for the past ten years or so at this company is probably about to change. All these skills matter.
At any given company, how much one might matter versus another, that's going to be an it-depends situation because each company is going to evolve in a specific way based on the type of business they’re in and how they're going to act post-pandemic. Even the fact that do you have people who’ve all worked together for a long time. Are you having lots of turnovers? All that is going to impact which of the skills might be important in the short term versus the long term.
It's a matter of prioritizing them for what works best for your company. Mark, this has been phenomenal. What I want to do is I'm going to ask you one last question then I'm going to let you out the door. People need to know Mark Herschberg. The book is called The Career Toolkit.
If you want more information, you can go to my website, TheCareerToolkitBook.com. There, you can learn more about the book but you can also download free resources like how to create these peer learning groups in your organization. There's also a free app you can download for Apple and Android and a whole bunch of other material all available at TheCareerToolkitBook.com.
Here's the question I ask everybody as I let them out the door. As you leave the classroom, a meeting, get in your car and drive away, what's the one thing you want people to think about you when you're not in the room?
“He helped me see a larger view and let me recognize new opportunities and new ways I can advance my career to have an impact in my company and the world at large.”
That's the true definition of leadership because it's allowing people to understand not only what is but why it is and how they can succeed. Mark, it's been a pleasure having you on the show. Thank you for being such an amazing guest and thank you for your generosity.
Thank you for having me.
Thanks for all your help. I enjoyed having you on the show.
Thanks for having me.
From tracking criminals and terrorists on the dark web to creating marketplaces and new authentication systems, Mark 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!