Zack Bubb is a long-time fan of the show with one hell of a career trajectory. Recently promoted to manager of a technical team, we talk with Zack about how to establish himself as a leader of his former peers. In this show:

• Why you interview for your next position every day
• Two questions every employee asks of their manager
• How to reset your relationship with an employee
• How to frame a 1-on-1 conversation as a manager
• What is the actual role of a manager?

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Watch the episode here

 

Listen to the podcast here

 

Zack Bubb – Finding Your Stride As A First-Time Manager

We have an awesome episode. We interviewed Zack B who is a new manager trying to figure out how to navigate with his team. We give him some advice. He has some great questions and he takes us through his career arc, what he’s doing, and what he’s planning to do next. If you are a new manager or you have new managers, you’re going to enjoy this one.

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Frankie.

Ian, you son of a bitch.

We got a guest. We got Zack in the house, whose last name will remain anonymous because he has big plans to take over the world. We want to make sure that the broad appeal of this show does not spread into all areas of his life and ruin some of his big plans.

Thank you. I appreciate that. Thanks for having me on. I’m looking forward to it.

We can just brand you as Carson Wentz. The first time I saw you, I was like, “He looks like Carson Wentz.”

I don’t know if that’s a good thing or a bad thing.

How did you find out about us? How did you end up here on our show?

It started with my wife, who works for NVR Mortgage, which you both used to work for. I was at a Maryland basketball game with her and a few other of her coworkers for a recruiting event. One of them mentioned that you two had a show together. I listen to a lot of podcasts, so I figured I would give it a shot. I was not expecting much, no offense, but it quickly grew into one of my favorite shows since then. You’ve mentioned a few times that you are open to having a guest. I thought I fit the bill for that, so I reached out, and here we are.

That’s pretty cool. We appreciate you following us. We’re excited to dig in with what you’re up against. What’s your background? Where did you go to school? What was your major?

My background is all in Engineering. I studied Computer Engineering at Virginia Tech, where I graduated in 2015. Since then, I’ve been in the professional industry. At that time also, I got my Master’s degree in Computer Science. I have a very strong technical background. Over the years, as I progressed through my career, I’ve been a programmer and software developer the whole time. I have been working my way towards leadership. That’s where I’m starting to get to now, which I would like to discuss.

I like that you said I’ve been in the professional industry. Frank and I have been in the jackass industry for a long time.

I feel like jeans have run their course. I feel like it’s time to go back to slacks, but slacks aren’t what you want anymore. I’m like, “Do I wear a pair of nice Lululemons?” These are the discussions that I have with myself internally about the professional world. Ian mostly takes conference calls in shorts and a dress shirt. His wife is like, “You’re on the phone with Asia?” He goes, “Yup.” All business in the front and party in the back.

It works out well for me. You go to Virginia Tech. You’re a Hokie. Out of college, I assume you went to some job fairs and did some interviewing like every other college kid and took a job at a big company.

While you're young, take the risk and join a startup. Click To Tweet

That’s exactly what I did. I started in college. I interned at this company because they were local where I grew up, so I knew them. I talked to them at a career fair, applied for an internship, got that internship, and did well enough that they asked me back immediately. I didn’t even have to worry about looking for a job in my senior year. I had it lined up the entire year and got to enjoy the last year of college.

Did you choose Computer Engineering? Are you one of these kids that was always on a computer as a kid messing around with Python and different programming languages, or did you do it because you knew it would pay a shitload of money after college?

It was both. I grew up a big sports fan, not much of a computer fan. Most of my coworkers grew up playing video games. I was not one of those kids. I did take intro to programming in high school, which introduced me to programming. I fell in love with it in high school. I knew going to college that I wanted to either be a computer programmer or something of that sort. I didn’t grow up with video games and computers as most of my coworkers do.

You worked for Hughes. It’s a big ass company. What did they have you do? Did you work as a developer?

I was a low-level entry-level developer. I was the lowest man on the team, taking the small jobs. I slowly worked my way up to learn the product and the system. I was developing new features and helping debug features in the system. I was also on-call for part of that time. They are an internet service provider. If something goes out, it needs to be fixed immediately. There were a couple of 2:00 AM and 3:00 AM that I was getting calls to look into issues.

Is it largely troubleshooting code for the most part?

Yeah. It was code that I wrote and broke and had to figure out.

You get used to a big company with a big company hierarchy and lots of layers of management.

They are a public company. They were the industry leaders. I learned a lot there. It was nice.

How long were you there?

I was there for about two years before I moved on to my next role.

You then moved on to a different-sized company.

I had no intention of leaving that first company. While I was there, I was getting my Master’s on weekends and evenings. Through that, I had a class with the guy who started a startup company that had a technology focus. He was looking to recruit engineers to help him build a product. He pitched me and asked me to join the startup. I said no at first, but he was persistent and eventually talked me into it. I decided that while I was young, that was my chance to try a startup. I joined a startup company as employee number four that had no product and helped them build that from scratch. It was quite a big change from an industry leader that has been around for twenty years.

 

How did you rationalize the decision to leave something very safe, a safe salary, 401(k) benefits, and a pretty clear career progression to something that’s a pretty big risk?

It was tough. I enjoyed my job but I had always been starting to pick up an interest in business-type things and people management. There was no clear path, at least anytime in the near future, at the large company to get there, whereas at the startup, I would have a hand in everything. That was one of the draws. I also had a fiancé at that time and a wife who was supportive both financially and mentally. I wanted to learn and I figured this was my chance to try something like this. If it went ass up and I was out of the job in a year or two, I can go right back to my original job. While young, take the risk, try it out, learn, and see what happens.

I believe the correct term for that is tits up.

That’s our favorite. There’s a sweet spot there. There’s a period in time where it makes sense to take a risk. You have two incomes. You have no kids. It’s the moment.

I was about to get married, so I could hop right onto her health insurance and not have to worry about that. That was the big deciding factor too.

That’s smart. When you’re employee number four, it almost feels like you’re one of the owners because there are only four people in the company. Everyone is doing a little bit of everything.

I hadn’t mentioned that earlier, but that was part of the upside too, as well as the pay cut. There was ownership of the company at stake, so I had the chance to grow something and profit from that. Also being able to define what the product would be was interesting since there was no product at that time.

That was part of the allure as you were in the cap table. You were one of the equity owners.

The company had been around for a year before me, but mostly in a research phase. I’m not labeled a founder or cofounder, but I was one of the building members. I still own equity in the company.

What was the product?

It was construction management software. It’s a web-based tool to help commercial construction products manage all their documents and all their communications with one another. I had no background in the construction industry before that, so that was new to me as well.

I’m more of a construction guy than Ian is. Would it track everything from budget to schedule?

Exactly. It’s for commercial construction products, so a lot of RFI is going in and out of it, budget, all communications between owners, subcontractors and contractors, document changes, and all your standard document stuff.

One of the allures to joining a startup is knowing that you can help shape and define the product. Click To Tweet

You were there for three years. How did the product sell?

It sold okay. It took a year for us to even build a product, so the whole first year was heads-down building, meanwhile, the CEO was talking to potential companies. Once we got a product, we caught a pretty good break where the owner knew a construction manager in a big project in Baltimore that was about to start. As soon as we went to market, we were able to get one large product right away. That served as our experiment.

We didn’t push selling a lot after that so that we could focus on this one product to meet their needs and incorporate their feedback into our company. Over the next couple of years, we were on a slower sales path. By the time I left, we only had 4 or 5 projects on the system, but those were all million or billion-dollar products. The income wasn’t growing fast, but it was enough to cover our expenses.

What was your interaction with the customer? Was that your first time when you had heavy involvement with the customer?

It was. My interaction was that I would go to most of these meetings. The whole company did since there were four of us. I was mostly listening from a technical perspective to hear their feedback as to what features they’re looking for in the product, and for people who are already using the product, what they think needs to improve in order for them to sign a contract with us. I was in pretty much all the sales meetings to listen to that. It was my first direct interface with the customer.

I’m curious about your arc from when you start to when you leave and about the different jobs and the interfaces. I’m also curious how did you leave and remain an equity owner.

When I joined, it was just me and one other developer building from scratch. We didn’t have titles. We were just developers. That other founding developer left while I was there, so I assumed the lead developer role. We hired two other developers while I was there. We had a CTO. I never made it up to CTO. By the time I left, I was the lead developer. How I kept ownership of the equity is it’s in my contract. After being there for two years, that had vested. I already have them. I am not gaining any new equity. If they were to change their structure, that could affect me. It was vested at that time.

It would survive a sale though. There is some protection in there.

There should be. There was a lot of paperwork that I didn’t understand at the time.

I remember the first time I was presented with ownership docents when I was at NVR. I didn’t have a legal team back then. I didn’t know who to call. I remember I didn’t do anything with it for two weeks. Somebody called me and was like, “Are you doing anything with that?” I was like, “I’m too busy.” It was my way of not wanting to admit that I was overwhelmed by this. I don’t know who to talk to. You get a bit broader. Ian and I have talked about our counsels and the people we work with. You forward the email, they read it, and they give you the bullet points. It’s so much easier to digest than having to do it all by yourself.

That would be nice. I pulled up Google probably five times and then shoved the papers back to my desk before I shipped most of them out.

If you’re reading a legal document and you’re either going to Google or YouTube to figure it out, it’s probably time to use 411 or call one of us and say “Who should review this?”

Going to a lawyer and accountant probably would have been smart at the time.

 

You were there for three years. From the time you got there to when you left, how did you change? I look at every stop in someone’s career as they stayed the same or they got more valuable. It’s rare that you go down, but how were you a more valuable person after three years of working in such a small company?

When I first joined there, I was all technical. All I cared about was building the product and building the best product that I could. Once we got the MVP up and we got customers starting to use the product, I realized that our bottleneck wasn’t the technology. The bottleneck instead was finding new customers and finding a product fit. There was some disagreement in the company over that. Some people thought that we needed more features in order to sell more.

I quickly became more attuned to what features were needed and what bugs needed to be fixed. I started to make more pragmatic decisions based on, “Maybe perfecting the technology at this time isn’t what’s going to best help this company. We should instead look at processes or business management to help the company.” Over time, I went from completely technical-looking to taking a more pragmatic view from a product ownership type perspective.

In your opinion, looking back on it with the advantage of hindsight, did the company need more features, or did it need to be more aggressive in finding leads?

It’s hard to say. I would still say that we should have been more aggressive in finding leads. I see that as having two cons. You either get the contract and you get more money coming in or you don’t get the contract and you get feedback, and that feedback will tell you exactly what features would need to be added. We were going on insight at the time. The company is still around. It’s still bringing in money. I can’t say that the strategy didn’t work, but it was also still about the same size as I left it. If that’s what the CEO intended for it, then that’s great. That’s also part of the reason why I left. I was looking for more growth.

If you’re not growing in three years, you end up becoming obsolete anyway. Your intuition of, “Let’s get some business and figure out features along the way,” that’s what most great companies do. It’s called an MVP, Minimum Viable Product. You’re in the tech industry. You know that one. Go get the customers and then listen to what they wished your product could do more of.

A lot of companies get so focused on making the perfect product and thinking, “If we have a perfect product, everyone is going to come,” but it’s mythical. In my opinion, that’s procrastinating because you don’t want to put yourself out there and have people say no to you on a product that may be missing a couple of features but could still do the job.

That’s well said. I completely agree. That was something I learned over my three years there. I started with the technical-only mindset of making it perfect.

As a construction management software, what do you think of Excel?

That’s one thing that we’re trying to help replace. Honestly, Excel has some good features. It just gets slow when it’s got too much going on.

It’s an inside joke with Ian and me.

I went to this real estate seminar. Frank was leading some small group breakout sessions. The topic was software. For some reason, Frank is talking about software. There were twenty breakout sessions, and of all of the sessions, Frank shouldn’t have been in this one. He should have been in the other nineteen.

Ian’s memory is flawed. There were multiple things in the session, but the thing that came up where I stood out to be out of my depth was software.

You have to make decisions for yourself. The company is not thinking about your career, they're thinking about making money. Click To Tweet

They get into software. In fifteen minutes, they went down this rabbit hole of, “If we had better software, we would be running way better real estate companies.” They’re listing all these software that you should have. It was a list of twenty. It was outrageous. You could tell Frank was getting irritated with this group of owners.

Finally, he was like, “I went from 3 condos to 300 doors in Richmond in three years with Excel. The software is not your problem.” Everyone stopped and looked around a little bit and I’m in the back giggling. It was hilarious. He took all of these guys at a task. He was like, “I built an empire with chewing gum and rubber bands.”

That’s a good point though. It is that joke where you have 20 software products. You get one more to replace them all. Now, you have 21 software products.

You have 21 software products and the same number of revenue. Nothing is better.

I was in an interview with someone. I asked them a question. I was like, “You seem like a job hopper.” He’s a salesman. I wasn’t sure he was a salesman until that very moment in the interview. He goes, “I’ve jumped a lot, but I can tell you every reason why I left.” I thought that was a great pivot and something I’m going to ask going forward.

It’s a great question. I would like to ask you that. You’ve left roles and companies. What we are going to talk about is you’re moving on with a promotion to a new role. Why don’t we talk about why you left? We’ve touched on that a little bit. What were the greener pastures you were striving for? In your current role, what do you hope to get to?

Let’s start with the tech startup. Why did you leave? You were there for three years. Was it stagnant?

It was pretty much stagnant at that point. I stopped learning and being challenged. I was hoping to hire more developers and increase my role a bit more, but since we weren’t generally selling more, that wasn’t on the table. I was looking for the next challenge at that point. I felt I wasn’t growing anymore. I joined the company to take a risk, to grow and learn. After three years, I thought I got all I could out of that company. That was why I started looking for what is now my company and job. That explains the first two. That’s a good question because my resume now shows I’ve been at each company for about 2 to 3 years before I’ve changed to other companies or roles.

Don’t worry about any of that. That’s a qualifying question. You said something that I want to stick in your head. I don’t even know if you know you said it. You said, “I got all I was going to get out of that company.” That is the right mentality for your career. I’m going to stop for a second and give you advice here. Too many people think that they owe the company something more than they do. You were hired to do a job, which is to build a product and help grow the company. In return, you would get some career growth. You would learn. Your skillset would get broader, and you would get paid.

For three years, you gave the company everything you told them you would. You built a product. You listened to customers. You built features. In return, you grew to an extent. When you stopped growing, you were smart enough to say, “I’m not going to stay here because of some misbegotten sense of loyalty. I’m gone because I’m no longer getting anything from this company.” That answer is fine. It is on the company to keep you. It is not on you to stay with the company.

I hope that mentality stays with you because that’s the way a career should be. As long as both parties are getting a mutual benefit, then you should stay and the company should keep you. Whenever that teeter-totter starts to go on either side, if you’re no longer providing the same value, the company will flick you out. If the company is no longer adding to your career, you flick them out. That’s the way this thing works.

There are two ways to go about that. In a four-person company, you don’t have the ability to do something else. I’ve worked with people who, on their resumes, look like they turn over every eighteen months. They’re good employees, so what I do with those employees is I have a conversation like, “I’ve seen this pattern. Why?” They’re like, “I get bored.” I’m like, “Do you like working here?” They’re like, “Yes.” I’d be like, “Can we help you grow?” They’re like, “Yes.” I’m like, “Maybe before you get bored, let’s have a conversation about what’s next.” You can continue to grow and hopefully, you find a place where you can do that. If not, I agree with Ian 100%. You got to look out for number one.

You bring up a good point there. Getting bored at roles is something I’ve thought of in the past, but that might be a little scary to say in an interview because, as you’re touching on that, you might indicate to the company, “I might be bored here in the next year or two.”

 

Take your wife, Emily. She joins the company and knows nothing about real estate or home building. She starts in a very basic role that’s customer-facing at the very end of the process. It’s exciting. She’s learning. She’s being organized. She’s learning how to work within a team and learn the business. She becomes the best at it in the office very quickly.

She does it for a while. It’s fun and exciting for her to get better at it. If we said, “This is your role,” she would have been gone a year later. Instead, we were like, “You’re talented. You could be doing more here. We are big enough where we could do that. What do you think about sales, loan officer job or underwriting?” We gave her a lot of different options because we were smart enough to see she would keep repaying us, but she would get bored because she’s super talented.

That’s how she stayed at that company for seven years. We found different things for her to do and identified her on a career path. A small company might not be able to do that. You have to make those decisions for yourself because the company is not thinking about your career. The company is thinking about, “How do we survive next month? What do we do?” They’ll tell you they’re thinking about your career, but the company is thinking about being a good company. You are the only one thinking about your whole career.

I’ll try to keep that mindset in place while looking at what I’m doing.

In this next role with the third company that you’ve worked for, you’ve been there for three years. How did you get the opportunity and how did you make the decision?

Once I decided to leave the startup, I was in full job search mode. I went on LinkedIn, Indeed and Google. I was going on interviews at a bunch of companies. After interviewing for a few companies and getting a few offers, this was what I thought sounded the most interesting. I found it off LinkedIn and ended up getting an offer to be a software developer. It’s still a similar role to what I had been doing. It was a government contractor, so that was also something completely new. It gave me the chance to get a security clearance. That was attractive as well.

Does a security clearance help get you into VIP areas and clubs? Is there any value outside of work?

I wish. It was probably the opposite. You’re not supposed to advertise it too much. If I’m using it for those purposes, I’m probably going to get into trouble.

You get to this company and you join it right after COVID. What is it like trying to fit into a culture and a new company right after COVID hits?

It was tough, honestly. Two things happened immediately. One is I realized that while I was at the startup, I pretty much had blinders on the whole time. I didn’t recognize the growth that was happening in my career while I was there. When I went back to a larger company that had a good mix of senior to junior developers, I realized that I was much closer to the senior spectrum than I had applied for.

Jumping back in, you realized your skillsets had changed pretty drastically. You’re in a vacuum. You don’t see that. You go back to the workforce and you’re like, “I thought I was a junior. I’m a lot closer to a senior.” That’s why movement is sometimes great. Keep going.

It was a surprise to me, but you’re exactly right. After a month or two of starting to get integrated, I started to get a lot of questions from the other team members. I didn’t have to go out and introduce myself to them a lot. Getting a lot of questions from them helped me to get to know them and the team a lot better. It was tough because we didn’t enforce having cameras on at meetings.

It was 100% remote. I worked a year to a year and a half without ever seeing coworkers’ faces and without meeting them in person. Through answering questions, I felt like I got to know them fairly well, at least from an online perspective. I was looking to go into an office. It was bad timing for me that it was during COVID.

Naturally take ownership of the people that you work with more closely on your team. Click To Tweet

You had mentioned to us before the show that your responsibilities started to grow pretty quickly once you got into the company. How are you able to earn the respect of people around you in a remote environment where no one sees anyone? How were you able to get more responsibilities, and how did that play out?

I always try to make my boss’ life easier. Along with me, we hired a few other people. My boss’ team was growing. He started to have too many people than he could account for at one time. Naturally, I started to take ownership of the people that I worked with more closely on the team. I didn’t ask for it from him initially, but he asked me to take official ownership, not from an HR perspective but more the day-to-day responsibility as a sub-team of our team to take things off of his plate. I was trying to help my boss out and take things off his plate to do what I could.

You said a couple of things there that are uncommon for someone as young as you are. One is making your boss’ life easier. Many employees don’t think about work like that. If you take it to its simplest thing, the beautiful thing is you’ve been in a startup. Maybe part of your mentality of that so early in your career is because you worked in a four-person office and you were the fourth. When you join a startup that small, what are you trying to do? You’re trying to make the founder’s life easier. He’s spending money on you because he’s admitting, “I’m stressed and I won’t have time to do some stuff.”

In a small company, the founder is throwing stuff around like, “Here, take this.” You’re almost pulling it off of him because he’s used to doing it all himself. It’s pretty cool that you learned that mentality right away to make your boss’ life a little bit easier to show value. Frank, do you have anything to add to that? Many people that start in huge companies and are there for a long time don’t think about work the same way that he’s mentioning it.

If you look at fictional characters, you think about the guy in Office Space with the stapler. He is probably the worst example of an employee out there. He’s like, “I stapled this and I moved it from here to there.” People fall into that. They’re like, “That’s what we do.” With my company, people sometimes struggle with our pace, how much we do, and what we get done.

What you said is something that I would have pulled out of you in an interview. I would have loved to know and would have gone into sales mode immediately. What you told me is you have big picture vision. I can see that. No matter whatever role you’re in, everyone has got a boss. If you’re making your boss’ life easy, what starts to happen for you? I won’t answer it. I’ll let you answer it. When you figured that piece out and you started to make that transition because it didn’t happen immediately, but it happened at some point in your career, what started to happen for you?

It helped me achieve my goals because it was my goal to become a leader in the company by taking that off his plate and him asking me to be a leader of a team officially. It was the quickest path to achieving my goals.

Typically, it doesn’t happen immediately. What starts to happen is there’s a progression. What was the progression like? You went from coding every day to what?

I went from being responsible to 1 person, then 2 people, and then 3 people to eventually where I’m being handed a feature predesign level. I have to do the design and pass off the coding specifics to my team members.

Is that formal? Is that something where your boss is saying, “Zack is the lead on this. You’re going to take direction from him. It’s your project lead on a number of things and Zack is leading it?” No one’s saying, “Why am I having to answer to Zack?” He’s clearly clearing the path for you.

It was formal. It’s common for software things to have morning stand-up meetings for fifteen minutes for everybody to report their progress. I was asked to split off from the main scrum and take my team and run my own scrum. They knew clearly that I was the leader of that team and that we were a little separated from the larger team.

I want to give you something here that is worth diving into a little bit. Ian and I have been here for a long time since at the other end of the spectrum of adding value, pleasing the boss, and that stuff. For most people who are younger in their careers, there’s a point where that was important. Inside the mind of a manager is this.

You’re just someone that HR said to hire. You come in. At first, there’s a very little value-add. How much time are they going to take away from my manager or me in order to become proficient? You then become proficient, and then what happens in most instances is as soon as someone is proficient, what’s next? You’re always an annoyance like children.

 

They start to realize, “This person is proficient. This person has a capacity.” What happens typically is you get better jobs. You get better things to focus on. You might get a bigger scope. Corporate America doesn’t necessarily pay the player. They pay the coach. The CEO is the coach. They make the most, but you go from player to player-coach, that’s when you get your small scrum. Once you get your small scrum, you get the whole scrum. You’ve gone from player-coach to coach. That’s it. Can you use your words and explain how that has happened to you?

That makes complete sense. It happened naturally. I was already starting to take on a lot of questions and help them out a bit. At some point, it became official. I got the title of scrum master and became a player-coach. That also helped solidify for these more junior developers to know that I am officially in that role and that I am officially the one they can trust to go to for some issues.

There’s a common employee that Ian and I both have. We have a couple of them. One of them came to me and goes, “I’ve come to the conclusion of what makes you and Ian special.” He told me what it was. I’m not going to tell you. I‘m going to make you figure it out. We’re going to get to it. You become a young manager. If you want to become a much larger manager or if you want to chase that path, what would you imagine the difference between a good manager and a great manager?

I’m trying to figure that out. At that time, even though I was a scrum master, my title was still software developer. I was still technical-based. Now, I’m officially taking on some manager roles from an HR perspective. What I’m learning pretty quickly about what makes a good and great manager is I’m having a hard time delegating tasks that I used to do that I can no longer do. It’s hurting my performance and it’s probably hurting my team’s performance. A great manager probably has trust in their team and could hand it off to them and then focus on the larger picture of things.

Ian, the person is Harry. What would you think he said about you and me both that made us different from anybody else he has worked for?

I wouldn’t guess.

We were mentors. You’re in this weird spot. You’re trying to figure out that crunchy spot between where you were and where you’re going, and what you’re going to find is a handful of Zacks, people who want to make their boss’ life easier. Those are the people you invest in. I’ve had this feeling where I looked up to somebody else and I was like, “I wish someone looked up to me that way,” but what you forget and don’t realize is people do. You don’t feel it because you’re the one they look up to.

I haven’t realized that or come to that realization yet. I don’t feel like there’s anybody looking up to me.

I’m curious about the transition. You’ve gone from developer to scrum master. Scrum master is an extra task you’re doing as a developer. Something you said that’s important that you should continue to lean in on for the rest of your career was, “I started doing things before they gave me the title.” That’s another thing that is uncommon that I find, especially in a lot of young people. They’re like, “Do you want me to do that? Are you paying me more? Do I have a new title?” I’m like, “No. Just do it.”

If you want to get promoted or if you want a title, or if you want to get paid more, start doing things that the next highest-paid person in the company should be doing, and then when that position comes open, it’s a natural fit for everyone in the office to be, “Zack is already doing it.” There is no, “We got to go out and find someone. Let’s find a recruiter. Let’s have a panel.” They’re like, “Zack can do it.” It sounds like that’s what happened. Your boss quit and your company was like, “Zack is doing a lot of what he was doing.”

My boss asked me for a one-on-one call and told me he was about to put in his two weeks. The next thing that came out of his mouth was, “I’m going to recommend you to take my job because you’re the most qualified to do it. You’re already doing a lot of my job on the team.” He went to his bosses and told them. There was a bit of an interview process but they took his recommendation and that’s how I ended up getting his role.

I can’t count how many times we’ve promoted someone in an office, and someone who didn’t get the promotion asked to have a meeting with me. They were upset that they were picked over or not chosen, or not even asked to interview or panel. The question is always, “How much of that job have you been doing? Who comes to you? If you want to be a manager, tell me about the people you’re mentoring right now. Tell me about the last person you onboarded. Tell me about the last time you raised your hand and said, ‘Let me mentor you.’ How long is the line at your door from the new people asking questions? How patient are you with them?”

They stared at you and said, “I’m in a different job. I’m not in the management job.” I’m like, “The person we gave the job to could answer yes to everything I said and they were in your job too. They just did it without the pay. You only want to do that job because it pays more and you want the title. You’re not willing to do it unless you have those two things.”

Start doing things before people even have to give you the title. Click To Tweet

Companies don’t work that way. You interview every day for the next job. You don’t interview once and say, “Here’s what I think I would do in this job.” You interview every day, sometimes for two years, and then a position comes open. What are you going to tell me in an interview that you haven’t shown me eight hours a day for two years? Nothing.

To what Frank was saying, I should probably look at myself as more of a mentor because even though I hadn’t realized that, that was probably something that helped me get this position.

There’s a crossroad you’ll come to on your next spot with the people under you. I wasn’t on the mortgage side. I was on the operations side of the home building side, but there was a role that I interviewed for. I come to the company. I’m a project manager. I moved to costing. I moved to sales. It was easy peasy. Whenever they interview, no problem.

I was going from sales to sales manager. The first time out of the shoot, they gave it to somebody else. I lost the interview. The second time on the shoot, they didn’t give me that job. They gave me a production manager job. They were like, “We have a curve ball to give you.” The third time on the shoot, I got the job. Now that I’m removed from it for years, I look at it. The first time, I wasn’t prepared. I did all the homework, but I wasn’t good enough in the role. I wasn’t good enough at leadership in the role.

The second time, I was probably qualified, but they didn’t understand it, so they gave me a lesser role. When I realized that I didn’t get the job because they didn’t know that I’m good at it, that’s where I figured out the mentor piece. That’s where I figured out, “I got fourteen people who report to me. I’m not going to make one good. I’m going to make ten of them great.” The next time around, they were like, “We’ve seen what you’ve done in this role. Can you do that here? If so, how?” The question starts to change. The roles are different. The evolution might be slightly different, but the process is the same.

I won every single interview by talking about this. When I transitioned, I went from being crappy and understanding I was crappy at these things, figured out who was great at it, mimicked it, mirrored, it, implemented it, succeeded, and passed it down. I worked at the Outback. I love the Outback. We talk about this all the time. Whenever I got promoted to a new job, I was terrible at the new job. You feel bad at it, but then you have to master it, and then you have two jobs you are good at. You do that the 3rd time and 4th time. It’s no different in your career.

That’s good to know because I feel closer to that first interview situation you said you were in. Even though I did get the role, I don’t feel great at it. I feel pretty unprepared, even though I was doing some of it in the past. There were aspects of it I didn’t see coming, and it has been tough.

Here is a piece of advice. Don’t tell your bosses that, but be brutally honest with yourself and say, “I have a little bit of impostor syndrome here.” Stay humble and keep working those angles. What will happen in a short period of time is we will forget that you were once a newbie because you’re being tenacious in your own development.

That comes back to what we talked about earlier about the company no longer serving you. You’re going to find yourself bumping up against glass ceilings if you continue to do that. Ian and I did. We moved up a bunch. We were like, “There are greener pastures,” and that’s what we ended up doing. You can pick your path, but those are some of the things that could be in front of you.

That’s well said. That’s good to know.

Your boss recommended you. Did you get the job or did they interview you?

There was an interview process but it felt pretty informal. We were just going through the motions. Pretty soon after that, I was told that I would be taking on his role.

Did you get a new title out of this?

 

I do. I went up. That was another point of contention. He was titled manager. However, HR at a large company didn’t feel my resume was ready for that. They pushed back and wanted to bump me to the next software engineering level. That’s where I’m at. I’m still having some conversations, but HR blocked the manager title even though I’m doing manager roles.

Companies are so stupid. I’ll give you an example. I went through this. I was your age. I was maybe 27. My boss’ title was vice president of sales. He left to go to a different business, so he was out. He recommended me. I interviewed for his exact same job and everyone liked me. They all wanted me. They wanted me to move to Atlanta. I got the offer and was paid 1/3 of what the VP of sales was. My title was going to be general manager of sales. It was the same job, the same number of direct reports, same revenue, same profit center, same everything, but a different title and way different pay.

I was pissed because I knew they were going to do this because he was older than me. I do the job for a year and a half. I kick ass, but I’m still way underpaid and still have the stupid title. I leave. That’s when I left to go to NVR. The day I told them I was leaving, they were like, “Would you like a different title?” My boss said that but HR was the one that gave me the dumb title in the first place that started making me bitter with the company and the pay.

Immediately, they offered to match what NVR was paying in the salary. They offered the money I asked for a year and a half before, and they offered me the title the second I said I’m leaving. I said no. I left. They put an older guy in the job and he gets the same title and the money. The short-sightedness of companies is obnoxious a lot of time. Sometimes, you have to be a little bit forceful to get where you want. Don’t let HR control your career because they’re people with crappy careers.

This is where mentorship comes in. If there’s somebody under you and you fight for them, this is how you build a real team of people. We refer to one of my very best friends since middle school a lot. Ian knows him pretty well. I talk about my team here. He’s in a big job. He’s like, “These are my guys.” He has had fifteen years with these people and he has been able to promote them and move them to different jobs. They’ve also gone to different countries. Now he is on this huge account. He got his guys with whom he has built a relationship. You can do that.

To Ian’s point, we’re going to lose this up-and-comer. This is your conversation with HR or a senior. They’re like, “We’re being imprudent here. We’re going to underpay this person.” You don’t have to say, “I went and fought for you and got your raise.” They’re going to feel it and know it. There’s a line from a movie I love, which is, “I’m the hand up Mona Lisa’s skirt.”

You’re controlling the strings by doing these types of things. It builds incredible loyalties and it keeps great people, which if the person had fought for Ian, Ian doesn’t leave NVR. He doesn’t know your wife. He doesn’t know me. He stays in that lane and he flourishes there, but they were imprudent. You can influence that. That’s one thing about leadership.

You said they would feel it, and that’s exactly right. My first boss out of college at my first job is the only boss I’ve had so far that I can say I felt fight for me, even though he had never said anything of that sort. Unfortunately for him, it didn’t work out. That was a weird circumstance.

You’re in this weird spot. You talked a little bit about delegation. You’re starting to achieve through others. It’s a very different sensation to achieve on your own. I don’t do shit. Someone was in my office and was like, “I can’t see you sitting at a desk alone.” I don’t. There’s no reason. With the exception of the time I’m with Ian, that’s the only time I don’t have somebody else in this office with me. That’s how I work. I work in concert with others. I don’t do much. You probably can’t even sense it. It would be many years from now, that’s the type of stuff that happens and you have to embrace it.

That’s something I would like to talk about because that has been one of the biggest challenges for me. There are two challenges there. One is learning to trust my team members a bit more because they are good team members and they deserve trust. The second is since I was an engineer my whole life, it’s hard to pass down these tasks that I want ownership of and tasks that mentally I’m curious about, and passing down those tasks that I want to do in favor of tasks that excite me a little less like paperwork and things that I’m being asked to do. That’s my biggest struggle. It has taken a lot of my time and I feel like I’m less effective because of that.

You’re given new responsibilities. You have seven people on your team. You don’t get the title you want. They change your title, but they don’t call you a manager. You’ll get that at some point. Did you get a pay increase at least?

I did.

You got a pay increase for doing extra. How was your team told that you were the new boss?

You have to be a little bit forceful to get where you want. Don't let HR control your career. Click To Tweet

When my boss left, he didn’t tell my team until about a week after he told me and went to HR. At that point, things were already at work. He indirectly mentioned that I would most likely be taking over. About two days after that, his boss sent out an email to the entire program announcing my boss’ departure and that I would be the one to take his position after that. There was an email to the entire program.

That email comes out and seven peers look up to you. You’ve immediately changed in their eyes from a teammate, a peer or a buddy to the boss the second they read the email. Some people’s behavior doesn’t change, but I’m assuming some do. That’s how it works.

In some sense, the more junior people already looked at me as their boss. Their behavior didn’t change much at all even though it now is official, but there are more senior people on the team than me. Even though they mostly didn’t want this job, there was no resentment in that sense. It’s gaining the respect from them that even though I’ve been a leader for a while, they have 10 to 20 years of experience than me. They now have to listen to something that I tell them and they might think they know best. All the junior people are pretty easy. It’s the senior people that are a bit tougher.

People ask two questions about their boss on whether they like to work for them. Do I like this person? Do I respect this person? If you can answer both of those questions, it’s very important. Do you need the like? Not as much as the respect. I would say respect comes first, but you do need the like a little bit. If I don’t like my boss, I’m probably going to end up going somewhere else.

There’s a fine line. What I see with new managers is they tend to either focus all on one or the other. They want to be liked, so they become pushovers and get dumped on by the people working for them. They don’t lay the line down, so they’re not respected. They are so focused on respecting them and their title that people start to think they’re an egomaniac and a prick.

You want to try to find some balance there where you’re liked but respected. What you say goes, but people like working with you. That’s the role model boss that any of us have had. You’ve got to think, “These seven people who report to me, those are the two questions they’re asking themselves right now. I’ve got to answer those over time if not today.”

That’s good to know because I focus on the like a lot more than respect. I’m more looking to be liked. As I progress, I should probably transition and try to focus on garnering respect a bit more.

Did your company give you any formal training or any management training in this role to start?

There were a few online courses that they provided to me but nothing more than that. It’s a yes and no.

That’s typical. You get some crappy HR training. It’s nothing like the in-depth training that Frank has been through. That’s why he’s such a good manager. You get into this role. Did you have some one-on-ones with each person about how they would like to be led and how this is going to work? Did you sit down and try to get to know people and your relationship?

I generally did not. That’s probably one mistake I made early on. It was interesting timing that the company had done its performance review cycle. Officially, all these people had done their performance review with my past boss. Since my boss has gone, it was something that came to my mind. I should probably sit down and have a one-on-one convo with them to see if they like their jobs and to see how that performance review went and where I can help them go for next year.

How long have you been their boss?

About two months.

 

This is perfect. You’re 60 days in. You haven’t let this get too far. You could do this soon. Are you all in an office together or is it all virtual still?

About half of the team is in the office full-time because of the security clearance nature of it, but half of the team is still working from home full-time.

Get into everyone’s calendar. We can help you out with the list of questions you can ask. Talk to them and say, “For one hour, I want to talk to you. I’ve had 60 days to observe. Here’s what I see your strengths are,” and then list them. “Here’s what I see as your strengths. You’re hardworking. You’re smart. You’re a good problem solver. You’re a good teammate. Here are a couple of examples where I saw you’re a good teammate.”

Go through their strengths and say, “What have I missed? What strengths do you want to share with me that you think I’ve missed? Here’s what I’ve seen in 60 days. What do you think I’ve missed? Here’s where you’re performing. I’ll give you some tangible things that I’ve seen in 60 days. Forget the performance review. That doesn’t matter. That’s the old boss. He left. I’m here.” They care about what their boss thinks of them and how they’re doing. “Here’s a few things that I’ve seen that you’ve done well on a couple of projects. Here are some things in the scrum that I’m seeing that I like about you. Here are some things you’ve moved along with. Here are a few things that you could be applying your strengths better.”

That’s the second part of this. This is not, “Here’s what you’re screwing up, and here’s where your weaknesses are.” Screw weaknesses. We all have them but don’t focus on them because we can’t change them. “I told you your strengths. I told you what you’re doing well. I think you can be applying your strengths better in this area.”

I’m doing it with you. You’re a new boss. I’ve spent the last 30 minutes talking to you. You’re a very easy guy to get along with. You’re competent. You have a degree in Computer Engineering and a lot of good in-depth experience in smaller companies with authority. You’re 60 days in and you’ve not used it. You’ve not sat down in front of someone and used some of your authority to say, “Here’s what I’m seeing. I’m the manager. Here’s what I like. Here’s what I would like to see more of out of you. Is that fair?”

You can ask them, “60 days in, how am I doing as a manager? What do you want to see more out of me? What do I do that gets you motivated? How much more available do I need to be? Do you like to communicate by email, by phone or by Zoom?” There are all of those questions. There’s no reason you can’t reset. It’s a very logical time. You could say, “I wanted to observe for two months and I want to tell you.”

As an employee, especially if you have young people, I always want to know what my boss thinks of me at any given time. I want to know, “Where do I stand with this person? How do they see my performance? Do they know my strengths? Do they even understand what a catch they have in me because of how hard I work, how much I care, and what I’m good at?”

As a manager, I’ve always tried to be hyper cognizant of the fact that people wanted to know what I thought. There’s nothing worse than a passive-aggressive boss that doesn’t tell you what they think. You should share the good, the bad, and the ugly. Tell them, “I want us to have an honest relationship. I’m going to be honest with you and give you a lot of feedback, but I want it right back. I don’t have all the answers.”

This is another great time in this little 60-day checkup where you say, “Let’s get this on the table. I’ve been a manager all of 60 days in my life. I’m not perfect. I have not been to Harvard Business School to learn how to manage people. I’m learning as I go. If you have anything you can give me in feedback to get better, I promise to incorporate it. I promise that I’m going to keep getting better, but I don’t know how to get better if you can’t give me feedback. I’m going to keep learning and get better at this. You should expect that I’m also going to be honest about how you can get better in doing your job.”

To make your life easier, there is the Collaborative Strengths Interview. Somebody gave me a version of this when I was a young manager and I used it. Between days 60 and 120 is the absolute perfect time. You met with all seven people and went through this. The other thing is you can manage tighter. If you came in a little loose, you could manage tighter.

We’ve got to wrap this up in a second, but one of the things that are prudent is this. Ian gave me this advice years ago and I wasn’t ready to hear it. He said, “If there’s a non-performer on your team, petition to get rid of them.” What it does is very quickly it shows I’m likable, but I’m also firm. If there’s nobody on that, but there is somebody who’s maybe not performing incredibly well, you can say, “I’m likable. I’m easy to get along with, but you must perform.”

There’s an axiom in this. Ian and I were raised by school teachers. School teachers always think that every kid is great. What I realized in the last downturn is that if I’m not great, I get fired. That’s what happened to a bunch of people. If your people aren’t performing great, as a manager, you get fired. You have to hold people accountable and you have to hold them to certain standards. If you don’t do it, they don’t come for them. They come for you. To me, this is the first step in that process of acclimating and doing a great job of understanding it.

If there's a non-performer on your team, petition to get rid of them. Click To Tweet

The other piece is this. When you interview again and you say, “On my own, I went and researched how to manage. I talked to people who are great managers. I found some tools and I used those tools. These are the things I did on my own.” You’re showing initiative. You’re showing a plan. You’re going to then calibrate off of it. These are great things that you can utilize throughout your career. When it’s time to sell yourself, you go walk into that room to interview for whatever that next role is and you pound your chest. You’re like, “These are the things that I did without any guidance.” That’s gumption. Those are incredible things to talk about.

That’s great to know. You’ve added a few points to my talking list of what I want to talk to my peers about, but also what I can talk to my boss about as I do my performance reviews and talk with them.

On the delegating front, it’s worth spending another five minutes to get into this because I know you want some help on this. This is from a consulting perspective. There are many reasons why people aren’t good at delegating. Usually, with a new manager, one is you want to show your team your chops. You want to show them you’re pretty good at this stuff. Two, it’s all you know. You know the individual contributor stuff, so you end up doing stuff that should fall on your people’s desk. You’re like, “I don’t know what else to do. I’m getting paid this new big salary, so let me jump in and grab some stuff.”

There’s also a little bit of control freak of not wanting things to go wrong. You’re like, “I’m feeling a lot of pressure to get results for the whole team and I don’t quite trust them to do it all well.” Regardless of what the reasons are, something you should understand is that as a manager, you’re paid more. You’re overhead. You are a luxury. In a four-person company, there is no luxury of managing over two of them. You are all doing stuff.

You are a luxury. Your job is to get results from a team of seven people. What I want you to think about is how much stuff is landing on your desk that is below your pay grade, which is a higher pay grade than the people who report to you. Whenever that happens, you have to ask yourself, “Why is that? Am I trying to add value to my team? Am I trying to get them to like me by taking things off of their desk? Is it just habit that these things have been landing on my desk for six years and I’ve done them, but now I’m a manager, I’m not behaving any different?”

It’s a very counterintuitive position that you need to be thinking about things that are your pay grade. You have to have your boss define it. In my pay grade, what should a manager be thinking about, paying attention to, and managing strategically? In order to do those things, you can’t be doing individual tasks anymore. I’ll give you an example. I work with a home builder in the south. We did my delegating module from my training course. This guy had started managing construction managers. They made him the region manager of all the CMs underneath him. He had maybe ten project managers under him.

He had been promoted up by one of their peers. He struggled to delegate. I asked him, “Give me an example of something you keep getting dragged into.” He was like, “One of our window suppliers has been late on everything and they’re not responsive. I have a relationship with the owner of this window supplier. I’ve known him forever. The first time it happened, I called and got an answer from him right away and got them to jump through hoops for us.” Now, it’s at the point where anytime they don’t answer a phone, my guys are asking me, “Can I help get the window supplier involved?” The more we were talking, the more he realized like, “Oh shit.”

What has happened is his team delegates up all the time. They’re like, “Barry at Windows-R-Us isn’t responding again.” He’s like, “I’m on it.” He jumps every time his team says, “We need your help.” I said, “Let me ask you a question. Would you have ever called your boss to call a window supplier when you were managing a backlog of homes?”

He was like, “No. I would be horrified if they had to do that for me.” I’m like, “That was your job.” The next time someone calls you, say, “What have you done to get their attention? How many phone calls have you made? How many different approaches did you take to get it done? Why are you asking me to do your job?”

I’m giving you a basic example because that tends to happen in every management job. You start by being helpful to show value to make them like you, and then you start to become their crutch. Pretty soon, they’re delegating everything from their job to you. That’s not to say you don’t do things to help your team. You should be doing things they’re not in control of to help them.

Taking resistance out of their way, getting them more resources, and getting rid of dumb policies that are slowing them down. That is your job to help them in those ways because they can’t control those things. The things they’re in control of that they should be doing as a course of their job and the things that you did when you were in their job, you should not be doing for them. You should go out of your way not to do those things for them.

I’m going to put you on the spot. There are two things. First, with what Ian said, how does it make you feel? Be honest.

I feel uncomfortable. It’s a perspective I hadn’t thought about before. I’m going through my head and thinking about how this might play out.

 

Let’s play this out for a minute. What’s a way that you could say something to somebody if they bring something that’s below your pay grade? What’s a way that you could set the table prior to me coming to you with it? What’s in the strengths interviews that you’re going to go do? How could you set expectations? I’m putting you on the spot. I’m going to help you, but what is your immediate reaction?

My immediate reaction would be to dig into it and take it on myself. One easy thing to start doing is what Ian said. I should ask them, “What approaches have you taken before coming to me?” I should set that expectation that they should take 1 or 2 approaches before coming to me.

These things don’t come to me. Nobody comes to me and asks me to do their work because I don’t let it. It doesn’t go that way for Ian. I’ve got a much bigger staff than Ian, but what I do is I talk about what I’m focusing on and how that affects their day-to-day. I’ve got eight different divisions of people. I went through it and I did a roll call of what my eight days look like. All these different things are big. I talked about what the perspective was.

They don’t want to bring me a roofing subcontractor because they know it gets in the way of the bigger picture. Once they start to see that this is what Zack is working on, they can’t bring him these piddly things. They need to bring the big stuff, “I’m hitting a roadblock. Can you help me move it?” These things don’t happen immediately. They happen over time.

People take the path of least resistance. They know that if you get promoted, you’re good at it. They’re like, “Let me ask him to solve my problem,” but it’s not good. It has a three-year-old that wants to eat sugar in every meal. You can’t let them do that. That’s your job to prevent that from happening. How you do it long-term is you build yourself into a go-to for the higher level stuff, for career development, for the big picture, and for planning. They sit down with you once a quarter over coffee and talk about what their next twelve months look like. That’s how you become a mentor. You don’t get mired in the crap. You get to look up.

Those are two great points. I tend to hide many responsibilities from them because I didn’t think it was relevant to them, but to say it like that and have that take some things off my plate is a great point.

I’ll give you another example of this. The guy that I’m starting a technology startup is much more experienced. He’s very talented. He worked for me right out of college. He was one of my first hires. As a new sales manager, I had him in the field. He was going and meeting with customers all the time. He sucked at sales and he knew it. He wasn’t good. It’s because he didn’t have the skill yet. He hadn’t learned the skill like any skill.

He would get out in the field and would go see a customer and nothing would happen. He would ask me to come on visits with him. I would come and I would listen, but what I was doing wrong was I would take over the meeting. I was still in my early twenties. I was a brand new manager. I would start asking the questions. I would start closing. I would get orders, and then he would be like, “When Ian comes, I get sales. When he doesn’t come, I don’t get sales.”

What I was doing inadvertently was I was there to help. I was there to listen to see what he was doing wrong and I would coach him afterward. This went on for months and I didn’t even notice it was happening. Every week, it popped up on my calendar because I was local. My guys were all over the Midwest, but he was a local Chicago guy. He’d be like, “Can you pop down to Exxon with me? Can you come out to US Steel? I got that on Friday.” I would be like, “Yeah.” I wanted to add value. I wanted to help him but I became a crutch.

What I realized after a little bit is I’m stunting his growth. By me being there, he is not forced to look like a clown. I didn’t have anyone to do that for me. I would go to these meetings and not get sales and be like, “I better get better. I better learn how to do this.” He wasn’t getting better because I was going to every meeting with him. I was doing all the selling and he was sitting there taking notes and saying thank you.

I had to sit down and say, “I’m not helping you by going to these. I feel like I’m taking over these meetings. You need to grow a little. You can go to these meetings. You can call me before and you can prep, but I can’t do this for you anymore.” Part of the reason I had to do that is I had twenty sales guys working for me and I was spending all my time with one. He wasn’t one of the best salesmen.

I needed to be spending my time with the top five to see what was in their way or how do I help them sell more. Two things happened. He became a better salesperson by me saying, “Training wheels are off.” I became a better manager because I started spending time with all of my team and learning about a broader set of problems they were facing than just spending all of my time with David on the front line.

It’s not just you’ll be a better manager by delegating. Your team will grow more by you saying, “I know you’re asking me to jump into this, but let’s go back to what I told you a couple of weeks ago. I think you could solve this better than I could. You’re an incredible programmer. Why don’t you go do this? Come back and tell me if you get stuck but I trust you.” After a while, they’ll quit coming to you with those things. They would be like, “We know how Zack’s going to respond. He’s going to tell us to do our job.”

Those are good points. I relate to that first scenario. It might be tough, but I’m going to put these in place and give these a shot.

This has been a blast. We had a lot of fun. We could have talked to you for three hours about this. You got our email address. You got us your contacts. We won’t charge you if you send us an email and ask for some help on this. You’ve been an awesome guest. It’s pretty impressive what you’ve done in your career so far. We’ll be watching and rooting for you to go start your own company soon enough.

Maybe. I appreciate you guys having me on and giving all the advice.

Keep us posted. Best of luck.

I will. I greatly appreciate it. Thanks.

 

Important Links

• Zack Bubb – LinkedIn