Manage Your Manager: Creating Effective Culture and Communication With Mark Herschberg

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TBT 199 | Manage Your Manager


Learning how to manage your managers is a key factor in the success of any organization and the sanity of people at work. What does this mean exactly? Here to explain is Mark Herschberg, author of The Career Toolkit, Essential Skills for Success That No One Taught You. Mark joins host Penny Zenker to share important insight into how employees can communicate and engage with managers to meet results and expectations better and avoid frustration. He also discusses the unwritten rules of the workplace, career development, and the value of properly onboarding new hires. He emphasizes the importance of having the right culture for the organization and, most importantly, the right cultural fit for employees. Listen in for an insightful discussion on leadership, communication, and employee engagement.

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Manage Your Manager: Creating Effective Culture and Communication With Mark Herschberg

I’m excited to have Mark Herschberg with us. He is the author of The Career Toolkit: Essential Skills for Success That No One Taught You. 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 500 and in academia as well.

He has helped to start the undergraduate practice opportunities program, dubbed MIT’s career success accelerator, where he teaches annually. At MIT, he received a BS in Physics, a BS in Electrical Engineering and Computing and Science, and M.Eng. in Electrical Engineering and Computer Science. What does this guy not do? What is an M.Eng.?

It’s a Master’s in Engineering.

You are an underachiever. Mark helped to create a platform used to teach Finance at prominent business schools. He also works with many nonprofits and is serving on the board of Plant A Million Corals. That is a mouthful but clearly, you are pretty accomplished there. Mark, I’m excited to chat with you about what you have got going.

Thanks for having me on the show. It is my pleasure to be here.

On this show, we are looking to help people to work smarter. Also, to not just think about how they can work smarter but put it into practice. You could talk about it in your background but we said we would focus on helping people to manage their managers because when they want to build their careers, you talk a lot about career development. That is a key factor. It is a key factor to success in any organization and also to our sanity at work. What about this topic of managing your manager is important to you?

When we think about our careers and the many skills we need, we think about leadership, communication, networking, and negotiations. It is all-important but hidden among them are the unwritten rules of the workplace. That falls under the umbrella of managing our manager and fitting into the culture. Knowing or not knowing how to do this can make or break your job and even your career. It is not something we teach. There was no class on this back in college. Often, we figure it out only by stumbling.

Who wants to stumble? I would much rather know how it works. There is this culture that we all know in the organization that the organization fosters but there is that underlying culture, that communication culture that is unspoken. How do you uncover that? Maybe people are going, “I do not understand. Our values are integrity, productivity, and profitability.” That is what they understand as their company culture. How do we dig deeper into that to understand what that unwritten layer of culture is?

TBT 199 | Manage Your Manager

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

Let’s first understand what it is and we can talk about how to find it. Many companies, especially big ones, somewhere on their website have, “These are our corporate values.” I saw a Fortune 500 company spend two years making sure every employee went through their little indoctrination program to learn those values.

There was the way the company worked. I have a friend, not the company I referred to Fortune 500 but a friend once said at his company, “The way decisions get made is the loudest voice wins.” I guarantee you, that was not on their website but everyone knew when you are in the meeting, you scream longer and louder. Eventually, others give up, and that is how you get your way. That is the unwritten culture.

There are companies that believe in open debate. That is something I like about my team. I’m explicit with this with my team. When we are in a meeting, if you do not agree with what someone says, disagree, including, and especially me, challenge my ideas. I like that. Where other corporate cultures and some of this comes from different global cultures, where you do not do that. You do not say in the meeting, “I think that is a bad idea.” Instead, you will privately address it.

In some organizations, the meetings are effective for the show and the real decisions happen earlier. We see this with Congress. The debate they have on the floor is all for show and publicity. The real decision-making, and whether a bill would pass or not happened in the backroom meetings. Hay Street on L Street is where decisions get made.

Likewise, we know at some universities, when you defend your PhD, you are there and nervous. You do not know if you are going to get it, while at other ones, you have already spoken to all your advisors and met their objections and this is ceremonial. There is no right or wrong culture but it is important to understand the culture because if you are behaving in the wrong culture, you are not going to be effective.

It could kill your career. In context, I have heard people challenge their leadership in a way to develop a better solution. They were shown the door because that is not the way things are done there. Even if they have across their open communication as a value, they may live it in a very different way and that leader per leader can be different.

The culture could be in conflict with the written culture. “We value your input and open communication,” but do they really?

Sometimes it is team culture. Corporate culture is one thing and they are trying to establish an overarching corporate culture but in large organizations, very often, there is a team culture that revolves around the leadership and what that leadership is creating.

One culture is not necessarily better than another, but you want to make sure you have a cultural fit. Click To Tweet

We see this very commonly. I am an engineer by training. I work with lots of engineering teams. We even see how the teams engage with each other. Engineers are notorious for loving Slack. It is an instant messaging tool. Probably more people are familiar with it now that we have been working at home. Engineers will be sitting right next to each other but talking to each other on Slack. You do everything in the chat. They live and die on Slack.

Others in the company tend not to use Slack as much. What happens when you have engineers and non-engineers trying to communicate? Engineer says, “You sent me an email. I check that once every three days. If you want me, message me on Slack.” Every person is thinking, “I remember hearing about that but I never use it.” You have a difference in culture across teams, which could cause problems and discontinuity.

How do I discover what that unwritten culture is within my team and how do I work within that? Let’s take a scenario and you can help me. I get a lot of people who say that they are overwhelmed and overloaded with the workload that they have. Part of that is, how do they speak up? How do they communicate with their leader or with project leaders that they are overloaded when they feel like, “If I say anything, I’m going to lose my job. How do they identify the culture and communicate within that culture?”

The best time to do it is before you take the job. We will talk about that, and then we will talk about what to do once you are there. During the interview process, there are a number of questions you, as a candidate, should ask, or as a hiring manager, should bring up to make sure you are on the same page. We are not saying one culture is necessarily better than another. Some may be but others, you can say they are equally good but you want to make sure you have that cultural fit.

On the resources page on my website at, I have a list of those questions. If you read the blog post, the way to bring them up is to say, “Before we get to the offer stage or now we have the offer, I read this great blog post by this guy named Mark Herschberg. He says we should discuss this. You can blame me for doing this because it can be awkward.” You can put the blame on me. It is a good way to break the ice and broach this topic.

You want to ask questions about decision-making, communication, and culture, look for examples, not the words. Remember, when we are candidates, what happens? We say, “I’m good at running teams that are growing in size. What does the hiring manager say? Give me an example. Show me how. Do not just tell me. I want to see proof. We can ask the same thing politely. If they say, “We value employee input.” That is wonderful to hear. Can you give me an example of three things that you implemented because of employee input? Ask them to provide the proof.

We want to have this conversation ideally, while we are hiring someone. For many of us, while we are in it now, we are not changing jobs. How do we start to broach these topics? One thing to do is to create guidelines, especially if you are onboarding someone. You can start by saying, “As we bring Joe on next week, I would like to write up ideas for her on how she can be effective, especially now in the hybrid workplace and the virtual workplace where you are not around. It is harder to learn by watching others because we are not together.”

You can blame Mark Herschberg for this. We need to be more explicit about how these things work. When I start writing it down, can I write something and input from others? Now, you still might not broach certain topics like, “We all know the loudest person wins. Your boss might not want to hear that is the culture that she or he set but some of these other topics like we all like to use Slack or it is important to bring up topics prior to the meeting, that tends to be how we work. Let’s be more explicit about them.”

TBT 199 | Manage Your Manager

Manage Your Manager: Directly speak to your manager about their personal style or the team style.


I saw some statistics. I wish I could remember exactly but it was something like 60% to 70% of employees were deciding on the future with that company based on their onboarding. There were some specific things that were important to them onboarding, setting goals, understanding the guidelines and standards in the way the company works, and having access to leaders was critical. I’m 100% percent with you on the criticality of onboarding.

My question and I want to come back to it, is for that employee. Forget they have been long onboarded. They have been with the organization for several years and slowly over time, budgets have been cut. They are doing the work of 1.5 to 2 people as many people are seeing because of the pandemic that there is potentially more work that is falling upon them. This is why 63% of people are experiencing burnout symptoms now. How did they handle those discussions with their managers, managing managers so that they can alleviate some of the stress that they are feeling and be able to cope with the current workload that they have?

You may be able to directly speak to your manager about her or his personal style or the team style. One thing I do when I join a company and I go, “Hi, everyone. My name is Mark.” I introduce myself to my team. I’m explicit about expectations. Here is how you can bring things to my attention. I do want you to disagree with me. I set what the ground rules are. Whenever I hire someone, I’m explicit with that new hire, “Here are my expectations.” That is something, as hiring managers, we can do.

In this case, you are not the hiring manager, and you are trying to get this from your manager. If you do not have a relationship where you can say, “Can we sit down and want to go over expectations?” This is where you do it as part of the onboarding process. You say, “Whether Jill is coming on next week or you say for when we hire someone. I want to get this set, so we have it for the future.” Now you are not saying, “I’m going to you because I have an issue.” You are saying, “I’m doing something that is helping the team.” It opens the door to this conversation.

You are doing it in the guise of helping someone else who is new and starting. Let’s get some of these things down and clarify.

“We created this document. Blame me.” That gets you doing it without raising any feathers.

Nowadays, people are going back into the office or doing this newly into the hybrid, we have a change that could give that opportunity or that excuse to bring that up again and say, “Now that our working situation has changed somewhat, let’s sit down, reevaluate and rediscuss the expectations in how we handle the workload and communicate certain things.”

Whenever you get an opportunity or an excuse to bring it up and have it check-in, I think that we should always look to take advantage of that so that we can reset expectations and the way that we are working together. I’m a big fan of continual resetting to make sure that we are growing and focusing forward together based on where the circumstances are now.

If your manager cannot give you their preference, the odds that you’re going to meet it are pretty slim. Click To Tweet

If you are at one of these inflection points, if we are all going back to the office or going back part-time, I have a blog post on this topic that we need to be explicit in the rules for the new normal. When we all went virtual in March of 2020, it was quick. We said, “We will shift. We do not know how long this will be. We are making came up as we went.” Now it is a lot more intentional.

We are intentionally bringing people back to the office 2, 3, and 5 days a week. Let’s be explicit about what that means. Especially, if we are not there five days a week, we need to be more explicit about what is happening because not everyone is there to see it. We can’t all learn by having that shared experience in the office. Being explicit help and anyone in HR should be saying, “We need to do this across the company at the company levels but at the individual department levels as well.

What do you think is one of the biggest myths when it comes to managing your manager?

I would say that they are opaque, that they are hard to understand. Most managers clearly signal what their values are. There might be some who seem capricious but if you pay attention to motivation. It could be that they listened to the last person to speak to them. That is their value and you have to recognize it is a timing issue.

With managers, here is the technique you could try. This is one that we teach in negotiations. Would you rather question when we negotiate with someone? Some people do not know if it is about the money or the timing. I can say, “Would you rather a lower price or would you rather earlier delivery?” I give them a choice because now they are going to show by their preference what their values are. If your manager isn’t going to be pinned down, say, “Would you prefer that I send this to you in an email before we meet or do you want me to come by and walk you through it?” Give them that, would you rather, choice and that will allow them to express their preferences.

That is a great suggestion because that still puts the choice back in their hands but like you said, “You get clarity on the values.” I think for that same person that I said was overwhelmed by many different things coming at them, that would you rather is perfect as well. Would you rather me do this or would you rather me do this?

At the current moment in my priorities, I need clarification as to which one is more important for you or has the greater impact. That will give you some feedback on that. You can have a discussion about that. If you rather me do this, I’m happy to take this on. You know that means that this is going to need to be put back until tomorrow or next week. That, would you rather, opens up the potential for that conversation. People can reset their priorities with their managers.

There is an edge case I will bring up and this is a personal story. I had a new CEO. I showed up and the CEO berated me a few weeks in saying, “Why don’t you have a plan for this project?” I said, “I’m sorry. I thought the consultants planned. The vendor provided a plan in my first week that they had been working on for months. The plan made sense to me. I thought it was good but do you want me to have my own plan?” He said, “Yes, you need to provide a plan.”

TBT 199 | Manage Your Manager

Manage Your Manager: We need to be more explicit in what’s happening because not everyone is there to see it. We can’t all learn by having that shared experience in the office.


I said, “No problem. I will come up with a plan. Just so we are clear, what are you looking for? Do you want some pros to write up, some word document? Are you looking for a budget and timeline? Do you want me to give you a PowerPoint? I want to understand what you are looking for.” I gave him a, would you rather with a few choices. He said, “I don’t know.” At that point, I knew this was not going to work because if my manager could not give me, in this case, his preference, the odds that I was going to meet it were pretty slim. That is fine. It is time to leave.

I agree with you in that context. That is why you ask those questions. For those who are reading, I want to highlight how important those questions are that you ask because many people would say, “I will go away and do a plan.” They stay in a state of assumption and make all these assumptions about what is being expected or what is wanted of them in terms of timing like, “When do they need that plan by? What is it that they want in that plan? What is most important to them?”

We get afraid to ask questions like, “Maybe they will think I’m stupid. I do not know what I’m doing or they will think that I’m not bringing the initiative.” It is the opposite. When we ask questions, we are getting that clarity. We are knowing what is important to the people that we are working with, whether it is a client or manager. We need to take back our question asking authority. The authority to ask questions because we are putting ourselves in a position where we are not managing our manager if we are not asking those questions.

The only time you would ever get in trouble is if there is a clear policy and if your boss has said, “Your weekly report always needs to send by Friday. This has been the rule for months. When is it due?” “Friday.” “This has been clear for months.”

That might not be the right question but if they are overloaded and the boss has given them fifteen other things to do that they have stated as a priority, I endorse that somebody says, “This is what you have given me to do this week. I want you to know that if we are going to make sure that this report is done on Friday, we are going to have to only be able to do 2 of these other 5 things.” Open up the door if you wanted it to be an exception that this was done on Tuesday or something else. You could still open the door to say that maybe this report, if it is not as important as this thing, could be pushed off, eliminated or whatever the case be for the situation.

Anytime it is new, different or an exception, we should always feel empowered because it is not the standard practice. Even in your example, the standard practice but in unique circumstances, “We have many other things this week, something has to slip. Anytime it is slightly different, feel free to ask.”

Is there anything else that you feel when it comes to managing your manager that we have not covered yet that you think is essential that people know?

There is a whole bunch of other things we can get into but simply to recognize that when you think about our training and what we learned in school, for example, they taught us how to do Accounting and Chemistry. On the test, they said, “Here is the answer box. Put your answer here.” That is how we were trained but that is not how it works in the real world.

Anytime it’s slightly different, feel free to ask. Click To Tweet

There is a whole bunch of other things and we were never even taught to think this way. We were taught to answer the question given but we have to be more proactive in asking our own questions, whether it is, “Would you rather, or understanding how your boss or how your team likes to behave and make sure you adapt to that particular culture.”

Thank you so much, Mark, for being here.

Thanks for having me on the show.

What is the best website for them to go to find out more about you and your resources?

You can go to my website, You can see where to buy the book, follow me on social media or get in touch with me for speaking or other things. You can also see more content on the blog page. There is a free app. I know you have one as well because reading a book or listening to a podcast is a good start but if you want to make that time efficient, you want to have some type of recall of the content.

I know your app and my app provides that. Free app from the Android and iPhone stores and the link from the website. The resources page has a number of free resources, including the question you should be asking during that interview process about the culture. All of this is available at

Thank you so much, Mark.

Thank you all for reading, whether you have a manager or not, this is about communication. It is about asking questions. It might be in the way you manage your customer, clients or kids. These applicable strategies are cross-contextual. Think about if you took nothing more away than empowering yourself to ask those questions, gain clarity, be able to reset the expectations, and create clear priorities that are communicated. That is a way to manage your manager, kids, and customers. Whoever you are managing, even if you are managing yourself, use that technique to be able to help you to work smarter.


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About Mark Herschberg

Mark Herschberg is the author of The Career Toolkit, Essential Skills for Success That No One Taught You. 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, currently serving on the board of Plant A Million Corals.