075 - First-time tech leadership advice with Heather MacDonald, Kevin Miller and Jason Alba

April 13, 2021

Three leaders in software development and IT share tips for making the jump from individual contributor to leader, including how to know when it's the right time, how to balance your workload, and navigating the slippage of your hard technology skills.

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Seth Merrill:

Hello, and welcome to All Hands on Tech, conversations with top voices in software dev, machine learning, cloud security, and leadership. I'm Seth Merrill. For today's episode, we're sharing the audio of a recent panel discussion focused on how to navigate making the move from individual contributor to first-time technology team manager. You will hear the voices of our moderator, Kevin Miller and our other two panelists, Jason Alba and Heather MacDonald. 

Kevin Miller:

So my name is Kevin Miller. I am an independent IT consultant and I got into management about 10 years ago for a full-time company. I was a full-time person for 15 years, went into management about 10 years into that. And the reason I did it was mainly because I was looking for more fulfillment, I was looking for a new challenge. I had been a programmer, a SQL DBA person for a very long time. And I wanted to expand. I wanted to challenge myself and try something new. Jason, how about you? 

Jason Alba:

My name is Jason Alba and I'm a Pluralsight author. Right now, I have 36 courses on professional development and soft skills in the library. I'm currently involved in two SaaS companies, one I own outright and the other I'm a part owner in. And I am an advocate for people and their careers. I love everything that has to do with careers, career management, networking. I love helping people move to the next step in their career and help job seekers land their roles.

So that's pretty much my world. I used to be a developer and through a series of weird events, I ended up managing developers and that was profoundly interesting and different than what I thought it would be, but I love it. So I'm still heavily involved with the developers that I work with and the IT teams that I work with, but I've gone quite a ways from actually being able to do any of it. So, anyways, that's my story. Heather?

Heather MacDonald:

Hi, everyone. I'm Heather McDonald. I'm currently the vice-president of Strategy, Change and Communications for Zions Bancorporation. And my role sits within our enterprise technology and operations division. I have over a decade of experience managing teams across multiple sectors, non-profit and for-profits. And it's just something I'm really passionate about, is helping people understand what are your options? How do you get there? How do you build the skills you need to be successful? My absolute favorite part of my job and the work that I do on any given day. 

But I also do, other things related to our strategies for the organization. We manage all of our workforce of the future and technology skills development initiatives. And we get to focus on our diversity, equity, and inclusion strategies as well. And to me, some of the leadership development is tie directly to our ability to impact that as well. So that's kind of me in a nutshell. Kevin?

Kevin Miller:

Thank you. So let's jump right in. Heather, the first question is for you. And it is, what traits do you think are the most desired in a manager? And why would someone with those traits consider making a switch?

Heather MacDonald:

I love this question first off. I want to preface by also saying, I don't think anyone should feel, if they don't have these traits or any traits on any list, that suddenly it's like, oh, I can't be a manager. I think these are just some general observations from my perspective that I think are important, but there's definitely no one-size-fits-all leader. And you'll probably see that through all of us as we move forward today. But for me, emotional intelligence is incredibly high on the list. It's that self-awareness, the ability to self-reflect and to listen, to listen to your people and actually hear them and understand what they're saying, knowing that sometimes that feedback is hard and it can hurt and be really difficult, but I think leaders who have the ability to hear their people and understand that and take that feedback to heart. That's one of those things that helps make you more relatable to your team. It builds trust and helps you be more successful longterm. 

I think adaptability is super important. We all have faced it over the past year. If you're one of those people who hangs on tight to that control and knowing what you're doing, life it's really hard as soon as anything throws you out of that rhythm. Some of the best leaders that I've seen are highly adaptable in dealing, not just with themselves, but with others. And honestly, for me, my best learning experiences have come when a leader gives me the ability to figure it out on my own.

And for someone like me, who's a recovering perfectionist, letting go of that and being like, I want to tell you what to do every step of the way, but for you to grow, you have to take ownership and do it yourself, that's really hard sometimes, but it's so important for you and for the people you're working with.

Accountability and ownership. I hear this all the time from leaders across the board, you have to be willing to... What are you going to say yes to? What do you say no to? Where are you going to push back? You have to be willing to own the work that you're doing and problem-solve to get things done.

You have to want to build and coach and grow the people that are working with you and for you. Growth and development for them has got to be a priority for you. If it's all about you, it makes it very difficult for you to find like... That trust from your team, if they see it on it, new every single day that you're taking credit for their work, that you're putting yourself in the high sit, they'll see it, and they can sense that. So it's really important to think about how you're growing and recognizing your people along the way. 

And a bonus one that I found because I've worked across multiple sectors in different types of roles is the ability to make connections. Both with people, so that relationship building side, but also the ability to say like, okay, Hey, we're having this problem over here in this specific part of our technology team, but maybe our frontline employees or somebody else or something in a completely different industry went through that. Let's go back and reference, find those best practices.

Let's not repeat the stuff that somebody has already done. If you can connect the dots and help people see kind of where that big-picture is and how you get there, I think that's just a really valuable skill that helps you go further, faster. And again, I think people with these skills, they're going to be able to take the leap. They're going to have the ability to grow through the really hard stuff and come out on the other side as people that people want to work for, that people are excited to be a part of their team. 

But again, I think like not having these traces into deal breaker. Some of them are things that you can work on and improve. And some of them, like people have completely different skills that they would probably put higher on the list than the ones that I've listed here. 

Kevin Miller:

Yeah. I would say, for myself, adaptability was one that I didn't have it when I first started as a manager. And I was told I was very rigid and I needed to change. And I had to work on that. You could be the best coder in the world, but if you don't have the soft skills, management is going to be a challenge. And I was told that I need to do adapt and become more adaptable and change. And so that's one that sticks out in my head that you mentioned. 

Heather MacDonald:

I love. 

Jason Alba:

Yeah. Let me, let me jump in here real quick. I'm thinking about my favorite boss. I came out of a government job, which was very structured very hard to move anywhere. And I went to work as a web developer for my boss who was a lady who was phenomenal. Actually, she was the best boss I've ever had. And one of the things I loved about her, this characteristic or trait was that she empowered me. She was like, "Jason, here's what we want. Here's your resources. If you have any questions, come ask me."

And that's exactly what I needed. My personality type and everything that I find fulfilling in a job is for them to point me in a direction and say go. Now, contrast that with some really bad bosses that I've had, who are like, here's exactly what I want you to do, and here's how I want you to do it, and here's when I want you to do it. And I just felt like I was just kind of pushing buttons and not contributing.

So I love everything that Heather said. I mean, every single thing there was great. For me, when I think about your question, Kevin, it really comes back to what did I love in my managers? What were the things that I really loved about them? And those are the things that I found myself trying to emulate as I moved into management. 

Kevin Miller:

Yeah. Definitely. Definitely. Actually, Jason, this kind of makes me think, what are some of the myths around management?

Jason Alba:

I think there's a lot of myths around management. I think, maybe the first myth is that you'll like it. I've actually talked to people over the years who are like, I was a developer and I wanted to go into management. Because that seems like it's what the path is if you look at a career path. And I went into management and I hated it. And so I went back to being a developer and I'm like, you know what? There is absolutely nothing wrong with that. 

I think when you look at a manager or a leader, executive director, whatever level, you think that those people have a lot of power and authority and autonomy, and that might not be true at all. They might just be passing things through that were pushed down on them. And so if you think you're going to go into a management role and be able to make a lot of decisions and be able to represent your team better than your previous manager did, you might be surprised that it takes a lot of work.

And that's really where a lot of those traits that Heather was talking about, the communication and the listening and the adaptability. Those traits help you earn and gain the power and authority with the peers. Right? I'm not saying that you're going to get put into a management position and you're not going to have any power or authority, it depends on the organization, it depends on the culture, it depends on so many things, but as you bring your soft skills to the table, which is really where you need them as a manager when you're advocating for people and projects and budget and stuff like that, as you bring those soft skills to the table, you're going to be in a better position to actually earn that power and authority. 

One of the things that immediately hit me when I became a manager was that I saw the rest of my team hanging out and playing magic or going to lunch together or things like that. And it was really weird that I was immediately not invited to those things. I was still friends with them, but I learned that it was kind of a lonely position, right? I was no longer in that club. I was still on good terms with everybody, but I think people were careful the way they treated me.

And I think that was one of the most surprising things about being a manager. On the flip side, I had people who immediately, when I became a leader in an organization, they kind of like sucked up to me and they're like, hey. And they became my best friends, which I didn't really recognize until I moved positions. And that best friend thing kind of went away. And I was like, okay, I have to be really careful how I work with and manage relationships. A lot of times we might feel like managers are disconnected from us. And there's a reason why they kind of put a barrier in between managers and non-managers. Anyways, those are some of the myths that I found in moving into a management role. 

Kevin Miller:

It's good [crosstalk 00:10:58].

Heather MacDonald:

I love those. I think there's another one. And sometimes it's that elephant in the room, but I think one of the myths that I, I even fell into this early in my career, was that management is easy and that the people above you do actually less work than the people on the ground, like the people who are boots on the ground, getting the stuff done. 

Early on in my career, it was so easy to sit back and be like, oh yeah, I want to be vice-president and C-suite and all of this, because it's like, they're just hanging out. They're going to meetings. They're going to lunches. And they're doing all these fancy things. And I think the thing that you realize, the further you get into your careers, you're like, oh no, the level of responsibility, the things that they're accountable for, not only do they get bigger and bigger, but they also, it weighs on you on a different level. 

When you're an individual contributor and you're on the front lines, you're responsible, this is my code, this is my thing, my project I'm responsible for. You get up a couple of levels above that or however many it is and suddenly it's like, oh, you're in charge of a hundred billion-dollar project that has a timeline. And if you don't hit that success, the board is going to be upset, people are going to lose their jobs, we could completely fold or get acquired.

I think there's that thing. It's really easy to sit on the outside and be like, oh, my boss sucks. I could absolutely do that better. And maybe that's true, maybe that person was terrible in their role, but I think there's a whole side of management that until you're there and you experienced it, like Jason was saying until you get there and realize people treat you differently, it's hard to imagine and fully understand exactly what that looks and feels like. 

Kevin Miller:

Yeah. I would say one of the things about management is you're definitely going to be under a little bit more stress because now you have other people to think about, it's not just you. And something about the stress is, over time, you can build your stress tolerance. Right? Everyone thinks, my stress is at this level and I can't take any more than that. No, you can build it over time. 

And as you learn and as you get confident with things, your stress level will build. But yes, it's definitely not not a cake walk, not a walk in the park. Let's, let's move back to you. Let's stay with you, Heather, actually. And let's talk about how management isn't for everyone and who should avoid seeking a manager role?

Heather MacDonald:

Even just based on what we just talked about, it's like if you're only in it for the money and the title, you've got to find a better way. Can you become the next level of a developer? Can you change companies? Can you do something different? Can you get into a different type of a roller? Upskill yourself to become more valuable? 

I think, honestly, if you're looking at it like, I just want to make 10 grand more, I want to get VP right before my name. I get, on some level, that can be very important for some people, but if it's the only thing that's making you consider management, it's going to burn you out. And I think the other thing is it's going to burn out the people under you. And to me, that's just hard. If you're dealing with the fact that you could be going in there in that space, you're literally could be destroying the careers in the time of so many other people, because they can get burned out on you as much as you are on them. 

I think the other thing that I've learned over time is can you make the hard decisions and learn how to tough conversations but with kindness? Honestly, being a manager, it's inevitable. At some point, you will have to fire somebody. You're going to have to have a critical conversation with somebody, put somebody on a performance plan. If there's no money for raises or bonuses, you're going to have to have that conversation. 

And I think if you're one of those people who shies away from being direct and upfront, if you're not willing to make the decision on who gets what [inaudible 00:14:19]bill, who doesn't, there's going to be a piece of it that's going to be soul-crushing, potentially, at that point. And I'm not saying you can't build that. Because, honestly, I'm very non-confrontational, I don't like to be like in your face about stuff, but over time you learn that being direct and telling people the truth, and working through that with them, it's still hard and it still hurts, but it's better than kind of beating around the bush and then they wonder what happens when somebody shows up from HR with a pink slip and says, "Yeah, didn't your last day is today?" And they're like, "I didn't know it was that critical? 

So I think you have to be willing to have those conversations and make those decisions. And just repeating again, I think if you have no interest in growing or building others, if you are about you as the star performer, it's your career, your life, people can see through that. It's something that your team will lose trust over time, especially if you're taking credit for their work. You have to get okay with sometimes like you know behind the scenes that you were a big part of that success, but you need to learn when you can elevate your team members, help them shine. And sometimes that's hard when you want to get the credit and you did a bunch of the work, but sometimes that's not the point and you have to be okay with that. 

Kevin Miller:

And that right there is the fulfillment that I'm talking about earlier, right? It's, when you see your team thrive, you thrive. And you have to love that, right? And that's the type of person that it should take. Jason, what are your thoughts? 

Jason Alba:

Yeah. A hundred percent on everything. It makes me think about the first guy that I let go. I walked in kind of nonchalantly like, "Hey, you know, the writing's been on the wall." And I didn't say this, but I'm thinking, he clearly knows what this meeting's about. And he was broken. And I still hurt from that. That was years and years ago. It was one of the hardest things.

After he left the office, I left. And I'm pretty sure I went and bought a big ice cream and ate the whole thing. I was a mess that day. And it was really hard. But people do want directness, right? They want that honesty. And that's a skill that we need to learn. Whether we are in a management position or not, that's just a great communication skill. 

Let me shift gears just a little bit and go back to this guy that I was talking about earlier that hated his management role. Your question is, who shouldn't go into management? And I just want to give people permission. If you don't want to go into management, don't. The success of your career and your fulfillment, and even your pay, doesn't depend on you becoming a manager. There are ways where you can feel the success and you can feel the fulfillment and even make more money and not have a management role. If that's you and you're like, well, I really don't want to do this, but it seems like that's what I should do, I'm just going to give you permission right now. You don't have to go into management. 

Kevin Miller:

Yeah. And I would say, for those who don't like having the conversations, who would like to avoid conflict, the other end of that scale is someone who's very blunt, very direct, and that's not a great position to be in either. You need to be able to go to the extremes, but not live in the extremes. You need to be able to bring it back to the middle. 

All right. So, Jason, let's move on to another topic here. What are some of the steps and individual contributors should take to move into a management role? 

Jason Alba:

The easiest way to do it is to be in the right place at the right time, right? So maybe it's like your organization has certain needs and nobody can fill those needs or somebody just left or something like that. And I think a lot of people kind of luck into their management role. I like to think about how we can do things strategically. And so whether there's an opportunity you're right now, or maybe you're preparing yourself in the next few years, I would say absorb as much as you can. 

So I'm going to divide that into two areas. One is, talk to people, right? So go talk to your manager. Talk to executives at your organization. Talk to executives and leaders and managers in different organizations and ask them what their path was and what they like about being a manager or a leader. What they dislike about being a manager or leader. What they wish they would have known, or how they could have prepared for it. 

I love learning from other people. And I think this is a great opportunity for you to go out and talk to people. And as you do that, the side benefit is that you're going to expand your network. You're going to share your brand as someone who's interested in management and leadership. Your name's going to get out there. So this is a great strategy, overall, for finding those management positions. But I think you can gain a lot of information from people who are just a few steps ahead of you. 

The other thing I would say is read books. There are a lot of excellent books. There are books that founders of companies sleep with, right? They they're on their nightstands. Then they read them multiple times. I've heard of people... Someone's like, "Hey, I read this book every year. This is the book that I read every year to remind me." There's the basics like 7 Habits of Highly Effective People, Made to Stick-

Kevin Miller:

[crosstalk 00:19:19]

Jason Alba:

Good to Great, I love The Cheese one. In my MBA program, this is really old book and it's from a manufacturing plant, but it's called The Goal. Right? These are things that other managers and leaders have cut their teeth on. And the interesting thing is when you start reading these books, you start being able to think more strategically and think like a manager. And then you start learning the language of the manager. 

And when you're, when you're in those positions and somebody starts talking... If you're coming from a very technical role where you're good at the jargon of technology, and then you walk into a manager leader meeting and you're like, I have no idea what they're talking about. Right? I remember I worked with the vice-president once who was on stage and he kept talking about the physical year, the fiscal year. And we're all like, what's a fiscal year? He didn't know the difference between in language fiscal and physical, right?

And as you learn the language, definitely learn finance. I've been astounded to see the people that move up or the people that have real power in some of these meetings are the ones who understand P&L. They can talk financial things. And when you're in a meeting and you can't keep up with the financial part of the conversation, your opinions start to matter less. You have to be able to understand the language of business.

Anyways, I think those are some great ideas to talk to people, absorb, learn, read books. A final step I'll say is, you really need to understand where you're at on soft skills. You need to understand what they're calling now emotional intelligence. And you can practice this right now no matter what your title is, but become more aware of yourself and how you interact and react and all those things. And become more aware of others so you can understand how you might influence and help others. Those are things you can work on right now to step in as a strong manager or leader. 

Kevin Miller:

I would also add to that communication. If you're not someone who likes to have conversations, if you're someone who writes long emails, I know you want to get all the details across. I was the same way. And I quickly learned you got to keep them short. Which means you don't write something short, you write something long and then you trim it. You trim it to get to what needs to get out there. But communication is a very important skill. What about, and I'm going to switch over to Heather, what about working long hours? Is working long hours or requirement for management? 

Heather MacDonald:

Honestly, I'm going to say it probably varies by company. Because I know there are some companies that that kind of the culture is, we're grinding all night, people are working weekends. It's a hundred-hour weeks. I think you have to... This is a personal choice. You have to understand, number one, what you're willing to do, what you're capable of doing. If you have, obviously, kids, family, you've got caregiving responsibilities, or if you're going to school, you went back for your MBA, whatever that looks like, you have to understand what that looks like. You have to be clear and upfront about what you can and can't do.

So like if you're at a company where the management roles are expected to be in there long hours, and that's not something that's going to work for your life, either table that or look at other opportunities. I think I find that balance of knowing, because I am in a manager role, t's harder. If I let something slip, I'm potentially putting three, four, or five people behind schedule on their stuff and that's not fair to them. 

So I absolutely have days where... Like yesterday, I was working late until probably 8:00 or 9:00, maybe 9:30 last night, finishing up some stuff because I knew that this morning, my team needed to hit the ground running and take those things and get the work done. I think it's also figuring out how do you maximize your time during the day so you don't feel obligated to work late into the night. That is super challenging. I mean, I have two kids and I like to spend that time in the evenings with them when they come home. And sometimes it is like I'll spend that time right when they get home. it's dinner, it's bath time, we're hanging out. And then I'll come back on the computer a little later when it's quiet and I can get some stuff done. 

I also have given myself permission, and I'm really grateful science has been great about this, is I give myself the permission to say, hey, during the day, it's communications, it's the meetings, it's being super present with people and doing that kind of management-level tasks. Sometimes I need that strategic thinking. Really quiet. Nobody's going to bother me late at night time to do that. 

So I give myself the okay if I miss an hour during the workday because I'm hanging out with my kid, but I know I'm going to pick it up over here. I think you really have to work smart to figure out what works for you, what works within your company. And just be clear and transparent. I talk to my leader all the time and say, hey, here's what's going on in my life. Here's where I'm at. If you need me right away, I'll jump right back on. But I think it's being open about what that process looks like for you and understanding, at some companies, if it's an expectation, it's an expectation. And if you're willing to commit for a time. 

I think for some people, especially if you're early career, working 80, 90, 100 hours a week might work for you when you don't have kids, maybe you don't have a partner or a spouse. And maybe it's what you need to get ahead or get you where you positioned for where you want to be. Bu at this point in my life, it doesn't work for me. so I have to find that balance, too.

Kevin Miller:

Yeah. That's that's a great approach. So, Heather, let's stay with you. Why don't you tell me what type of people should a person surround themselves with if they want to become a manager? 

Heather MacDonald:

Oh, this is a great question. I think the thing that comes to mind for me is people who aren't like you at all. Honestly, one of the biggest things that you realize, especially as you get higher up is you're going to end up having to work with people who you have fundamental differences. Your cultures different. Your way of living is different. Your background is different. Maybe you don't agree with their values or how they approach the work. But you have to get okay with and get comfortable with.

And it's like you were talking about earlier that communication piece. If you can't speak their language and figure it out like, I'm an introvert, you're an extrovert, how do we work together to get this stuff done? It's just going to be really challenging in an unnecessary way. I think we all need to be comfortable challenging our assumptions, being open and upfront. And acknowledging that we have differences, but we're in a workplace to get something done, and that we need to either be willing to set those differences aside or be willing to sit down and conversation and figure out how to work through them. 

So it could be a piece of spending some of your personal development time. It's that balance of, I'm going to take that Pluralsight course and get some Python information, but I'm going to go on my social media feed and I'm going to add in influencers and people who are completely different from me. So maybe I've got somebody from the Native American community. Maybe it's somebody from an African-American business woman who's in there.

Just exposing yourself to people who think differently and see the world differently is huge. Because you're going to hit that point where you're maybe working with a board member or a C-suite individual who comes at you with something that feels like it's out of left field, but if you can't put yourself in their shoes and understand where they might be coming from and why they're requesting that thing, again, it just creates unnecessary friction that doesn't have to be there.

And I think in our global world, especially if you're working for a global company, you have to be able to understand and communicate across cultures and across differences if you want to be a leader. I think it will eventually prohibit you from moving up at some point if you can't do that effectively. 

Jason Alba:

Kevin, when you first asked this question, my immediate thought was, if you want to be a manager or a leader, surround yourself with managers and leaders. Learn how they think and talk and you'll find new opportunities and just expand your network there. But I was thinking just a couple of days ago, my family decided that we're going to be a puzzle family, like we're going to do puzzles on a table. 

And so we got one and it was pretty good. It went actually really well and fast. And we're like, oh yeah, we're really good at this puzzle thing. And then we got another puzzle and it was exceptionally hard. It was really hard. And so I'm sitting there at the table and my neighbor kids, I think they're six and 10. These two girls came over and they're looking over my shoulder and they just start putting the puzzle together. And I'm staring at this thing and I'm like, I can't do this. 

And what I realized eventually was that I was looking for patterns of the image on the puzzle pieces. And they were looking for patterns of the cutout of the puzzle, right? And it just hit me, in our circle, we need to have diversity to understand. And it's great to network and talk with other managers and leaders and learn how they talk and think and all that stuff, but we need to not discount anybody at any level because people that are at, let's say the bottom, the entry-level positions, they're doing roles that you've been away from for years and decades. And they're faced with challenges that you don't even understand because you're not doing it. And they have creative solutions. Right?

And so as a manager and a leader, you have to be open to bringing in as many diverse thinking or thought processes as you can. So who do you surround yourself? Well, surround yourself with people that you want to become, but make sure that you're not discounting input from anybody. 

Kevin Miller:

Yeah. I think that's a great way to look at it. I'm actually looking at the Q&A section here. And this isn't so much a question as it is a statement. But someone anonymous stated, "I'm always afraid of moving up the ladders. I will miss out on the technical skills and I will become disposable if I'm not able to take credit for my job."

And to that, I would say, along with what Jason just said, right? As you move up in the ladder, you're gaining new skills and you are getting away from the technical skills, there's no doubt about that, but you're going to surround yourself with people who have those technical skills. So there is a shift, right? As you start here and you start to move into management, you're not looking to surround yourself with solely management people. Yes, of course, you still want some, but you also now want to surround yourself with some of the more technical people so that you can stay connected to those roots. 

Let's jump over to another question here. Daniel, if you could pull up those questions and kind of ask last two, that would be great. 


Okay. First one, how important is deep technical knowledge to being a successful technical leader for a small development team specifically? 

Jason Alba:

I'll jump in on that. I've managed small technical teams. And I remember... I don't think you have to be extremely technical. Okay. You don't have to. It really helps though. I remember one time we were white-boarding a problem and my developer was up at the whiteboard just kind of walking through this issue and they're like, "This actually is impossible. We can't do what we think we want to do. So we have to figure out what our objective really is and do something else." 

And I was like, "Why can't we do it?" And they're like, "Well, because you can see, logically, a, B, C, D. And this just breaks right here." And I was like, "Well, actually..." And I stood up and I got a marker. And I was like, "Well, actually, here's how I would do it. And I had been a programmer and I loved... My forte was in database design and stuff like that. And I loved it and they didn't know that. I think they didn't understand that.

So my ability to be able to stand up and say, "Actually, here's how you can do it and here's how it can work." And they were like, "Oh yeah, you're right. And we're going to think a little deeper the next time we present a technical problem as being impossible." I don't think it's a requirement, but man, it really helps to able to speak the language that your tech team is talking. 

Kevin Miller:

I was a developer as well for a very long time. And I switched into project management first. I remember going through a couple of tough scenarios with a developer of mine who was just running into a roadblock left and right and couldn't figure it out. And he was racking his brain over it. And I said, well, show me the problem. May maybe I can help. And he was a little surprised because he didn't know I was a developer for as long as I was. And so he did the same thing. He put it up on a whiteboard. He thought I was just wasting his time. And I said, well, have you tried A, B, and C? He said, I never thought of it. He tried it. And it worked. And he said, how did you know how to do that? I said, well, I come from an IT background.

So it does. It's not necessarily a requirement, but if you don't come from an IT background, if you don't have the coding experience or the database experience, you should at least talk to those people, try to learn their language a little bit. You want to have conversations so that you're not a complete outsider. Go to lunch. It'll come up. It will absolutely come up. As developers, I can tell you, we talked about it over lunch. So just go to lunch and have those conversations. It'll spark your ideas when you run into a problem. 


Next question. How do you manage one-on-one conversations with your team members without it feeling like you are calling them to the principal's office? 

Heather MacDonald:

I love this question because we all have been there. You've been there where it's like, do you have a second? And your heart starts racing. You're like, what did I do wrong? I'm about to get fired. You're like something... Your mind is like I think just because of like, even as good of a relationship as you can have with your team, there's always that slight level of fear when somebody's like, do you have a second? And it's coming out of left field that you're like, ooh, panic.

I think one of the things that I try to do, and maybe, Jason, maybe I was reading one of your tweet threads that I saw this on, but it's giving people context. So sometimes they'll be like, hey, I need to discuss this with you for a minute. It's about X. Or I need to talk to you about this. Don't panic. It's not a big deal. If you're busy, we'll catch you later. Giving people a little bit of a cue of either like, here's the actual context of what I want to talk about. Because usually, you're going to know what you're talking about. 

So say so. Or at least let them know that it's not panic-worthy. Maybe it's a good thing. Maybe you're calling them in because you're like, wow, we got an extra bonus and I'm giving it to you. You can just tell them, "Hey, it's a good thing. Nothing bad. Just whenever you a second hit me up. So I think giving people a little bit of a heads up just helps diffuse that situation and it can keep people from losing their cool. 

Jason Alba:

Yeah, I agree. That was actually in a course that I did. I don't remember which one. It was recent one. But giving people that heads up even saying, hey, here's what we're going to talk about and we'll talk about it in a few days. Give them time to think about it. The other thing to answer that question, why don't you normalize one-on-ones? Right? 

I worked at an amazing, for me, it's the benchmark company of how to set up a company culture. It's called BambooHR. They're out of Utah. They do HRIS software. And we had one-on-ones every week. And it was a lot of work, right? There was a lot of work for the managers, especially as they had bigger teams. They spent a lot of time in these one-on-one. They were up to an hour. But if you normalize one-on-ones, then it's not getting called into the principal's office. It's just having regular and good communication with your boss. 

Kevin Miller:

Yeah. And I would actually say, I remember a comedy special. I think it was by Wanda Sykes, but she said the two words that will put fear into every employee's heart are see me. And that's the truth. Right? When somebody said, see me, it was my boss, it was, oh my gosh, you always think the worst. And so as a manager, something you can do is say, "Hey, we need to talk. By the way, it's nothing bad." Right? 

Now, if it is something bad, yes, you probably want to approach that a little bit differently. You might want to set up an agenda but you don't have want to give someone so much time that that's all they're thinking about, right? So don't set it up a week in advance or three days in advance. Try to say, "Hey, by the way, do you have a minute? Come talk to me." And we'll walk to my office together this way. They're not so anxious. 


Next question. Bridging the gap from individual to tech leader, it usually takes a lot of emotional intelligence. How have you grown this skill in your own career and especially within the tech space?

Kevin Miller:

I'm going to take this one to start. I'm going to sound like a company man here. Right? But I took courses. I took Pluralsight courses. I went to seminar, live seminars, back when we could do live things. Right? I talked to other friends. I found a mentor. And I can't stress the importance of a mentor because when you'd have someone who's going to point out where you are lacking, right? I'm going to call them weaknesses, right? Where you're lacking, where you need to improve, and that person's going to be honest with you and then say, "By the way, here's what you can do to help that." It means a lot. It means a lot to get that honest feedback in a positive way and to have someone who's who's got your back. 

So I would say find a mentor. And don't just go to someone and say, "Hey, can I pick your brain and ask questions." Actually say, "Will you be my mentor?" Right? Be upfront about it. Be direct about it, because then they know what's expected of them. And they're going to push you a little harder, right? They're not going to hold back. And so I think that's important. And of course read. Jason mentioned reading, and watch courses, learn.

Jason Alba:

There's a good rate course in Pluralsight by Shelley Benhoff. It's called Moving from Technical Professional to Management. It's the course for this topic. She talks about a lot of this stuff in there. When I was doing my emotional intelligence course, like I said earlier, the first pillar is self-awareness. So that you're even asking that question. It puts you in the right path. Right?

So think about where you're at and how you communicate. And when somebody gives you feedback on your communication or your relationships, internalize it. Not in a harmful way, but internalize it in a way that you can go back and say, "Okay, I actually need to work on that. I thought I was really good at this thing, but I need to work on that." So just being aware of where you're at and that you can improve is going to help you with that transition. 

Heather MacDonald:

I agree. And sometimes it's getting out of your comfort zone. I think you build your emotional intelligence and your adaptability by being out of spaces that you're normally in. So if you're very comfortable in your developer group or with your specific team members, I'd say go volunteer somewhere, go sit on a board, go get outside of what's normal and typical for you. Because you'll start to gain exposure to other people and how they work. You could start to see what resonates with you and what doesn't. 

And you kind of have to do exactly what Jason's saying. You have to self-reflect on that. So if you're in a different situation and somebody is rubbing you the wrong way, you've got to sit back and go, "Why is this triggering me? Is it because this person is everything I'm not and that feels weird to me? Is it how they're doing something? Is there mannerisms?" 

Sometimes it's just it's getting that exposure to something different. You can start to adapt your personality, not your personality, but how you come across too. It's one of the ways that I've found is very effective is just being in different places. Because then you can learn by example. Sometimes it's watching those people who do it differently and going, "Okay, let's think about how I can apply this to myself and learn from there."

Jason Alba:

I love to watch people and it's either, "Ooh, I like that. I'm going to emulate that," or, "Whoa, never do that. That landed really bad."

Kevin Miller:

So, Jason, let's go with you. How can a good manager avoid becoming a bad manager? And how can a bad manager turn themselves into a good manager?

Jason Alba:

This is a huge question. So I'd like to take the next four hours and walk through this. We talked about so many traits and characteristics of what management and leadership is. For me, I think that listening is so critical in a manager role, right? So even if you're... Not even if, but let's say you're a product manager and you're working with a customer and trying to figure out what you need to develop. If you listen wrong, if you don't understand what the problem is that you're trying to solve, you're not going to come up with the right solution. Right?

And so you need to be able to listen well. My most popular course is actually on listening. I didn't think it would be a hit, but there's a lot of people that have really resonated with how do I become a better listener. Now, here's the other part of that. Step two or part two is you need to help your team feel heard and feel understood. It's not just that you're a good listener, but they need to feel validated. And I think it's really critical as a manager, if you don't want to be a bad manager and move into that good manager space, when your team feels heard, they're going to respect you more. And I think you're going to make progress towards being a good manager.

A couple other things we talked about, I told you that I love being empowered. I love it when my boss kind of lets me run. Part of letting your team go and do things is letting them fail and helping them through the failure, right? And so excellent managers allow failure to happen as long as improvement comes from it. Like, what did you learn from that? I remember walking into my first postmortem with software team and I wasn't sure exactly what to expect, but the whole culture of that postmortem was, we're here to figure out how we can do this better the next time. 

And when we help our team understand that it's okay to make mistakes, because that's what happens when you risk. You risk ideas or you risk new processes or systems for improvement. That's the goal. Sometimes we're going to stumble. And if stumblings okay, and they know that they're not going to get punished for that, you're walking into excellent manager territory. 

Heather MacDonald:

Do I have just one more thing to add? It's tactical, but it ties to everything we're talking about. You have to have the self-awareness to know what your limit is. I think, honestly, and I've had this conversation with people on my team is like, what is your limit where you're like, I'm done, this isn't for me, I don't want to do it anymore, I can't do it anymore. 

You have to have that self awareness to know like, am I having a bad day or is this a bad choice? And you have to know when to be like, okay, I need to wave the white flag. I need to go talk to my manager and say, "Hey, I really don't think this is a good fit. I really don't think this is going to work out for me. What are my options to either go back to being an individual contributor, to re-assess what your roles and responsibilities are. 

And I think, honestly, that's a really hard place to be. You work so hard to get there and you think this is going to be the thing, the ticket for you that is going to make you feel fulfilled and excited about work. But I think it's just as noble to know. And we talked about it earlier, is when you've reached your limit when it's too much, too much, and to be able to step forward and say, I've reached that point and I need to do something different, I think that's...

You'll save your team too. If you can get to that place where you can have that discussion with your manager, you've made a plan, you can go back to the team and say, "Hey, this has been hard. I'm transitioning into something else. It's for the good of all of us." People will respect that more than you continuing to burn yourself out and be a bad manager and to make feel life's miserable. You don't want to be miserable. You don't want them to be either. So no one to hit the button and be like, I'm out. And that's fine. It's totally fine. 

Kevin Miller:

And I would add that that's not failure, right? You tried something new, you took the chance. You had the guts and you took the chance. You tried something new, didn't work out, and you made a decision. You moved on. That's a whole lot better than never taking the chance. Right.? To always be afraid to say, I don't have what it takes. Take the shot. And if it doesn't work out, that's okay. Right? That's your path. And your path is just that, your path. And that's okay. 

Heather, I'm going to stay with you for the final question here. Did you ever think you made a bad decision by moving into a management role? 

Heather MacDonald:

Yes. All the time. It's funny because even though I have plenty of time in as a manager, but you can sit there as an individual contributor, you kind of you know your role, you know what you're supposed to be doing, you know what's expected of you. Oftentimes, you can be like, okay, I've done my project. So I'm done. It's onto the next person. We shipped. It's somebody else's thing now. But I think as a manager, the thing about being in a leadership space is you start to see the holes and the way that you do things and the way that you come across, the way that you work with others that you might have been able to hide behind as an individual contributor. 

So being in a leadership role is that constant assessment of, oh my gosh, could I be better? Could I be doing something different? Am I really just not clear? Maybe I'm super successful as an individual contributor, because in my mind it makes sense. But as a manager, maybe I come across as really convoluted, I don't give clear instructions, I don't know how to give people the balance between here's the project, go run with it versus the people... There's going to be some people who are going to want you to say, I need you to do A, B, C, and D. If you can't ever figure out the difference, that makes it hard. 

And so yes, absolutely, there are days where I'm like, I quit. I just want to do something else where I could do a job and go home. But I also think the thing is I allow myself to have those moments where it's really tough. And then I go back to it, but I'm like, but it's my team that makes it worth it. Every single day, if I help them be better, if I can help us be better together, if we could move the work forward, that's what pulls me through the really hard stuff.

Kevin Miller:

Same question to you, Jason. 

Jason Alba:

When I was in that room, letting that guy go, I really questioned it. When you have to do hard things, and like Heather said, it's inevitable. The hard conversations are going to come. And in those times it's like, I don't want to be here. I'm feeling all the wrong feelings right now. And it'd be a lot easier if I was just an individual contributor. 

I also questioned it a lot when I realized that I very quickly lost my technical skills. And I think that's one of the bigger concerns that a lot of techies have is, if I move into management, what's up into my technical skills? And that's real. There's ways that you can protect that. Like maybe you code 10 hours a day or... Not a day, sorry. 10 hours a week or something like that where you still are involved a little bit. 

But I wasn't, and I didn't. The thing is I always wanted to be a leader. I always wanted to be C-suite or lead a team or build a product or build something huge. And so this was my childhood dream and goal. So what I realized was I moved, I transitioned from building really cool things to building really cool teams and building leaders, building people and building careers. And I get a kick out of building that. I love building companies, but I love it. I love doing it as I help people grow. So yeah, have I ever questioned becoming a manager and a leader? Sure. But but I love it. I do love it. O

Kevin Miller:

Okay. So let's jump back over to some questions. Daniel. 


This question I thought was really good. It kind of related to what Heather said. They said, "I'm transitioning into a management role and I find myself juggling a lot of things and getting all these random questions and requests throughout the day. Do you have any tips for staying organized and dealing with kind of the constant random?"

Heather MacDonald:

That is the thing, isn't it? I feel like once you get into a manager role, and especially depending on where you sit in the organization, sometimes the stuff that comes outta left field, you're just like, I don't know what to do with this. To me, I will self admit I'm not the most organized person, but it's also my personality to just kind of fly by the seat of my pants and get stuff done. It works for me. I know it doesn't work for everyone else. I think it's knowing yourself and know you have to do to set your boundaries. So it might be blocking out specific chunks of time to do those really simple tasks like answering emails where you can just get through them. I know that there are different methodologies of like, "Hey, if you can do it in five minutes, you do it. If it takes longer, you got to put it in a pile and schedule time."

I think also just setting clear expectations for your team. Like, do you have those service level agreements where you can be like, nope, it's going to take me two days to act you on this? And that's fine. And people know it. If you communicate clear expectations of what people can expect, it's easier for you to create that space to be successful. But if you're letting people come out of left field and you're just dropping everything to do everything that comes up, it's not necessarily going to be the most impactful thing. Sometimes it's looking at what's actually important and you need to do to move the work forward versus this might be urgent, but it's really not that important. Or there's 20 other people who could answer this question.

Get good at delegating, get good at setting boundaries and expectations. And then understand it's never going to go away. I don't think I've ever worked in management role where there wasn't some level of, ah, so much random.

Jason Alba:

Yeah, I would agree. There's always going to be a little bit of chaos at times, but if you're living in 24/7 chaos or what I should say is 5/40, right? All eight hours of your day in chaos, you got to work on that. Because chaos usually leads to not getting things done. And Tommy van Schaik actually has a great theories on time management. And it talks about what Heather just said, urgent versus important. You want to focus on important. Urgent, sometimes needs your attention right away, but you want to focus on important to get the things done that are most important. So you want to take a look at the time management. If you find yourself being always living in chaos, you're going to burn out. Eventually, everyone does. And the people below you will burn out because they can never get in touch with you. They can never count on you. And so that usually just does not work. 


I think we have about time for one more question, if that's okay. I'm at a smaller company that doesn't have management openings very often. And I'm likely have to step into that role with a new employer. Our company is willing to take a new person without management experience. Any tips to like how to find a position that is outside of your current job?

Kevin Miller:

I'd actually like to take this one first because this actually did happen to me. It was during the financial downs turn of 2008 to 2010. My company simply was not hiring. They were actually letting go of people. And I knew there was no opportunity for me, but I wanted to move into management. And so I went to another company that had an opportunity. But it was made very clear, and I was very appreciative of this, that I wasn't going to take over a team with 10 people, right? That's too much for a brand new manager. 

I started with one, one person. And so it was a team of two, him and I. And then we started to grow that team as time went on. And I think that's a good way of approaching it. And that is something I think you should be looking for if you are just stepping into management. To take on a team of six, seven, eight, 10 people, you're taking on a lot. And I know you may be ambitious, but just slow down, right? You have your whole career ahead of you. And so just slow down, try to take maybe one or two people to start things out, to see if you even like it. And then build from there. 

Jason Alba:

[inaudible 00:49:27]So a career coach would say that what you need to do is figure out what your transferable skills are, right? So what does it take to be a manager of number of people or type of organization or team or whatever? What are the skills that you need to be successful in that role? And then really sell those skills, make sure that you work on those skills, that you can talk about those skills. Maybe you need to go into a volunteer position at a non-profit where you are managing teams, even though they're volunteers, right? But they're still teams. 

So take what you want to be and figure out how to write that script. So you can say, oh yeah, I've done this here. And I've done this there. And I've done that over there. And put all of that together to show that you can step into that role. 

Heather MacDonald:

I agree with that. You've got to be able to articulate the connections and translate that for people, because I'm one of those people I've jumped across industries, sectors, I've done a whole bunch of different stuff. Part of it could also be a tactical thing. Is there something even in your job where you can actually own it and work on it? Is there a project you can own? Is there some... Even if it's like, I'm going to run the committee for employee appreciation week, or I'm going to run the committee that's going to do something. Can you get some level of leadership experience there? 

I absolutely second the volunteer thing. That was the most recent career I had before what I'm doing right now. And honestly, managing volunteers is a million times harder than employees because they don't have to show up. You can think you're going to get 200 people to that relay race and two people show up that day. You're going to learn really quickly how to adapt, how to be effective. So I absolutely think, can you be in a space where you can get those skills? You just need to spell it out. 

I've gotten resumes from people who I'm like, I can see the connection, but if you're not going to spell it out for me, I can't assume that you can make that connection for me. So sometimes it's just being able to talk about your story and how you can make that jump that somebody's going to be willing to give you a chance. But I do second what Kevin is saying, start small if possible with a really small team. It becomes exponentially harder the more and more people you manage. And if you're not already effective with one, it's going to be really, really challenging to be effective across five, 10, 15 people. 

Kevin Miller:

And remember you can be a leader without being a manager, right? What does it take to be a leader? A follower. That's it. So someone thinks that you're a bright person and they really like your ideas and they like your approach to things and they like how you handle difficult situations, you are already a leader. Period. And if you get enough of those people who think that way, people are going to want to make you a manager, right? And so then it's just a matter of opportunity. Right? I actually just wrote an article on this. It's called chair management. And it's all about, fill your chair with someone who you can help to basically to get into your position and then you have the opportunity to move into another. So I would just say, just remember, you don't have to be a manager to be a leader. And that's important.


I wanted to give you the opportunity as we close out today, if you'd like to leave kind of a final takeaway, a final thought, or plug anything that you'd like to as well. 

Kevin Miller:

Sure. I'll go first. I'll say this becoming a manager was very fulfilling for me. And I'm still friends with some of the first people I started to manage. And that was a decade ago. I'm still very close friends, I should say, with a lot of those people. And so the friendships and the fulfillment and seeing them grow and knowing that I helped them grow, not all of them, but most of them, it's just so rewarding. It just made it all worthwhile for me, even if I did lose my technical skills, which I might be a little bitter about because I was techy, but it was just so great.

And I would say if you a question on here that wasn't answered feel free to reach out to me on social media. I am on LinkedIn. I am on Twitter. Find me there and let's get a conversation going and I'll try to help where I can. 

Jason Alba:

My final thought will be management is about people, is about people. And the success of the company, the sales, the optimization, the systems, the processes, those are great, but when it comes down to it, you have families that you're impacting. So if you like people and you want to impact people, then management could be a great place for you. 

Heather MacDonald:

I agree with both of those things. It's definitely about the people. That's the best part of being a leader. Honestly, it's the thing that I live for, is to see people get better. I want to see people surpass me. I want to see them do more and bigger things than I ever could have done, especially by myself. So I absolutely adore that.

I definitely think if there's questions that I can answer, I'm always happy to I'm on LinkedIn. You can find me there. But this has been great. I hope people have some really great takeaways that they can work with and really kind of self reflect on some of these things. There's never a shortage of really great leaders. And I think sometimes you do have to just give yourself that chance and take the leap and see what happens. 


That's it for today's episode. If you're interested in viewing other Pluralsight panel discussions live, visit pluralsight.com/events for a calendar of upcoming webinars and live events. To listen to more episodes of All Hands on Tech, visit pluralsight.com/podcast.