Beyond the Command Line: Transitioning from Individual Contributor to Leader

The one and only Leo is going to tell us to how to get beyond the command line.

So, it's funny. I spoke at another B-size conference a couple years ago, and I'll be honest, this is the largest group I've had in one of my sessions. Uh, and the last time I had a session this close, uh, they put Leah Pate outside on the door. Uh, and then everybody was very not happy with me that I am a male and not a female. And so, uh, with that it became like a running joke and then my handle turned into the real Leah 3 because I'm the third Leop. Um, but yeah, so uh, quick question. Who here has ever been asked to solve a problem and they've had no idea in how to do it?

Yeah. Now, picture doing that in a leadership role, right? So, you got no road map. Stakes are high if you mess up. Uh, and you're still expected to perform. So, that's where a lot of cyber security leaders start right now. >> Oh, good. >> Is that better? >> Oh, all right. So, that's where a lot of cyber security leaders start, right? They're high performing individual contributors or IC's, right? And they're thrown into management. And it seems pretty logical. The fact that you're great technically, you performed, you delivered, now go do this and make other people do this too, right? So, while that logic isn't totally wrong, the same skills that you made people high performing individual contributors also

tie into uh leadership, but it's dangerously incomplete. Right? Being an outstanding individual contributor does not necessarily mean that you're going to be a phenomenal leader, right? So without the right support oftent times that promotion kind of feels like a setup, right? And so that right there is the leadership gap. So we'll get into that a little bit later, right? But today for this talk I want to offer clarity tools and a real world roadmap for anyone stepping into leadership or you're thinking about jumping into it. So my goal is to not help you just survive that transition but lead in a way that's effective, confident, and sustainable. But before that, we can talk a little bit more about me real

quick. So, working backwards, uh I'm currently a senior director at Net Spy. I run one uh of our US uh regions, right? So, I have about 70 to 90 uh security consultants that report up to me. Uh and uh before that, I was a managing consultant at Invisium. Uh so, I was another smaller, it was a smaller significantly smaller boutique consulting firm. Uh I ran the consulting team there for about three and a half years and then Net Spy uh bought us. Uh and then before that I was a cyber warfare officer within the South Carolina Army National Guard and then the time before that I was a human resource non-commissioned officer as a full-time professional soldier in the

army. Um unrelated, I am a phenomenal latte maker, or so I like to think. And because I have the palette of a 5-year-old, uh I love cinnamon roll lattes, blueberry pancake lattes, but that's not what I make on an average day, uh I make just a simple vanilla latte cuz time. Uh and then lastly, you know what I look like cuz I'm standing in front of you. This is me as Clyde the Cougar. Uh so for those of you that do not live in Charleston, South Carolina, uh Clyde the Cougar is a mascot at the College of Charleston. So in this picture, Clyde just received his class ring. Uh and that's actually me. So I

was one of the mascots uh for the college for about two and a half years. So here's our outline for today, right? So we're just going to take a quick look. We'll start by framing the problem. So why cyber security needs better leaders, right? Then we'll talk about the mindset shift uh from an individual contributor to a leader and then break down the core skills that every new leader needs and then pitfalls to avoid. After that, we'll get into managing people, especially the challenge of leading your former peers, which is always fun. Uh, and then we'll also cover how to build your leadership style and then how to keep growing once you're in a leadership role. After that,

we'll wrap up some Q&A. Uh, and so for our Q&A session, I actually have two books that I'll be giving out. Uh, it's the Phoenix Project. If you've never read it, uh, it's extremely relevant to this talk. I don't want to ruin it. Right? So, start I like the upside down pyramid. You start very broad and then, you know, you kind of narrow it down. So, in prepping for this talk, I was trying to find some really cool stats uh that might like kind of shock people. Uh and the one I came across was Isaca's uh state of cyber security report from last year. So, 66% of their job of people that they interviewed, which is around

1,800 professionals, uh say that their jobs are more stressful today than or at the time this report was being the survey is being conducted than it was 5 years ago. And that's just not workload, that's leadership strain, right? So cyber security teams are burning out. Not because there's now more attackers today than there were 5 years ago, which could be true. There's more bugs today than there were five years ago. There's more alerts today than there were five years ago. But ultimately I found they found that leadership teams are under supported. They're undercoached and they're underled. And so when we promote people for their technical skills without leadership training, what do you get? Right? You get delayed projects.

You get stressed out teams. And those two things turn into burnout, which you'll see a constant theme with those words throughout this presentation. Uh, and this talk isn't just about being a better leader, right? That's an entirely different topic. This talk is more about is more about being a sustainable one. So, as we look into the leadership gap, right, we'll start by framing the problem, right? So, the leadership gap is the mismatch between people being put into leadership roles and their actional readiness to lead, right? So in cyber security and tech this happens all the time. We promote high performing individual contributors into management without giving them leadership training or support right uh it makes sense from

a business angle especially in consulting uh where it's faster to promote somebody who already knows the ins and outs of the company. They know the culture, they know the TTPs, right? They know the stakeholders, they know the different teams, right? Than it is to bring someone external to the company who has to quickly ramp up to not only assume the role that they're were hired for, but then they have to go learn the tribal knowledge of the organization, right? So, however, while their technical skills are top tier, that doesn't translate into leadership skills, right? And so, being the best redteamer or engineer or analyst or developer, right, does not make you the best leader. it's a completely different

job. So, uh with that we see frustration from the new leader and their team and their manager when people are not prepared, right? We see micromanagement from leaders down to their teams. Like show of hands, who here loves being micromanaged? Loves having somebody looking over your shoulder critiquing everything, right? Like I surely don't, right? Uh and when you ask, well, why do people micromanage? Right? It comes down to a trust issue, right? the leader hasn't established that trust with that person to be able to say, I trust you to do the job that needs to get done. I don't care how you do it as long as it meets these things, right? Um and then we also see

miss deadlines and team stagnation, right? Progress slows, morale dips, and then people start burning out. And what happens when people burn out? They leave the organization. They go find something else, right? Which as a senior leader, good retention is great, but it's always great having some fresh blood into your organization. Bad like high numbers of people leaving your organization, there's clearly a problem, right? So leaders should be considered a force multiplier in my opinion, right? However, that force multiplication can go positive or negative, right? If a new leader is supported and there they're there's an emphasis on their development, right? then they multiply impact in a very good way. Right? If they're just thrown in, figure it out,

right? Some people will swim, others will sink, majority will sink. And then because of that, that's the bad uh force multiplying. And then the team suffers the most. So where do we go from there? The mindset shift, right? which I'm very proud of myself that I just said that term because I practiced this for the last couple days and I could not say those two words together. Uh but it's one of the hardest parts of the transition and it's one that nobody prepares you for. Like nobody when I moved into a leadership role, nobody sat me down uh and said this is what it means to be a leader now. Are you sure you want to do this? Right? I was in the

army and I didn't have a choice. I got promoted and it was like great here's five people figure it out. Right? Uh and so uh coming outside of a military and government world like as an individual contributor your worth is tied to how much quality work you personally crank out, right? So the top performers are the ones that are you know they always achieve results. They deliver either on time or early on those deadlines, right? They encourage people around them, right? But it's all about them, right? When you transition from an individual contributor to a leader, this bottom statement here, it's not about you anymore. And so uh so as a leader again that model breaks

it's not about you doing the work anymore. It's about enabling your team to succeed. So taking this taking this a step further uh that phrase the last phrase on the slide deck right it was one that was told to me when I was promoted uh to sergeant in Afghanistan in 2011. And it's something that over the last 14 years that I've kept to my, you know, it it's something that I still remind myself today and it becomes a perspective piece, right? And so I use it sometimes as a mantra when things are like going rough and I just feel like I'm just getting beat up by everybody and everything around me. You know, it's the the sacrifices that I make as a

leader is expected because I'm not it's not about me anymore. It's about the people that I lead and the people that roll up to me. my job is now to enable them. And so when you make it about your team and not about me, your entire perspective will change. Right? This is a piece of advice again that I share with every single subordinate leader that moves from a consultant role into a people leader role. Right? And we're going to spend some more time digging into this. So we often treat leadership as a reward for being technically excellent. But it's not just a step up, it's a pivot, right? You're not leveling up in the same game, right? It's not like you

started off as a network pin tester and then, you know, you started off on external networks and then you moved to internal networks and then you combined your powers together and then eventually made your way into red teaming, right? You're starting a new path altogether. You're making a career change when you move from individual contributor to leader, right? And so, you know, the the there's four pieces uh that kind of make this up that I was when I was putting this slide deck together. Being a leader doesn't mean you're getting more advanced technical work, right? In the consulting realm, you go from, you know, normally security consultant, maybe security consultant one or two, right? And then you move typically move into a

senior role, senior security consultant, then you'll move into a principal consultant where principal is the pinnacle of your career, right? you're seen as the technical expert in your domain or several domains, right? Being a leader though is not necessarily that, right? You go from being a very high performing uh individual contributor and now you're kind of like back you're you're moving up, but you're also moving back down because now you're typically start out a junior leadership role, right? It's an entirely different career change. And so because it's an entirely different career change, you're shifting from doing the work and to enabling others to do it. And so that requires different tools, different behaviors, and again a different mindset. So

strategy people process technology matter more than your individual keyboard time. You're moving from solving technical problems to organizational ones and you're starting to think bigger. So again, my experience is in consulting. So you go from I got to deliver this project on time. how am I going to do it? Uh methodologies, reporting, all that stuff to man, we have a capacity problem. How can I increase capacity without increasing my headcount, right? And the implications that come off of that. You're starting to solve more of those challenges, right? You're starting to take the blinders off a little bit more and see more of the picture, right? So the second block up there, managing people. So growing, maturing, developing people

is your new task, right? your new scope of work that you're trying to look for. One-on- ones, coaching, hiring, resolving friction, right? Resolving conflict, mediating those things, right? It might feel like a distraction, but it's what actually drives the outcomes, right? So oftent times you're like, man, I've got my boss told me to do something and I'm I'm involved in these other initiatives and I got to take care of this and uh now I got to stop my workflow completely and I got to go do, you know, 30 minute hourong one-on-one with people in my team. It might seem like a distraction, but that's another aspect of my of your job, right? And in the this hypothetical

I'm creating, right? Because your job is to enable those around you. Uh if your people are raising their hand and they're like, "I'm drowning. Can you give me a life raft and you're like, "Sorry, I got to go take care of this." Uh and you come back and you know the water's now up to their chest and they're like, "I'm still drowning by the way." I don't know if you realize this. Uh you know, like, "Oh, I got to go do this other thing, right? Eventually that person will drown, right? Hopefully. Hopefully not, right? But, uh that person will drown." And then by going that path what that you know translating that that person's going to leave your

org right and that person could have been very detrimental to your overall team and you missed it because you didn't spend the time uh to dedicate that time to them right so the the third block in there emotional shift and this is probably one of the hardest ones that most new leaders come into right uh letting go of the work that you love right watching others struggle with something you can fix in five minutes right? Uh you're sitting there and you're watching, you know, having to coach somebody through something and it's like, man, in your head, you shouldn't say this to them, but in your head, you're like, the amount of time it's taken me to explain how, you know,

what I needed, I could have already have done it. The problem with that, though, is that that's only one task. And you might have a hundred, right? And you can do all 100, but you're not going to get all 100 done when they need to get done, right? And so therefore, you're going to have to enable these people and allow them to struggle. But there's beauty in the struggle, right? Because you're enabling your team to grow. You're enabling them to tackle a problem, tackle a challenge that they've never had to deal with before, and they're having to navigate and figure that out for themselves. You're there to coach them. You're there to provide direction, but at the end of the day, they it's a

task you assigned, and they got to get through it, right? So, at that point, you're no longer concerned with getting a task done. you're now concerned with enabling them to make it happen. Right? Then the last one, outcomes over input. You're no longer judged by what you get done, but what your team achieves. Right? So, as an individual contributor, performance is personal. How do I move forward? How do I get what I need? I need this training. I need to go and do this. I need I need I need, right? And then as a leader, it's collective. My team needs more time. My team needs time to react. My team needs training. My team needs resources. they need X, Y,

and Z. Right? So, some of the things in there that you can ask yourself to determine if they're actually growing, are your people aligned? Are they growing themselves? Are they delivering? Right? Those are your metrics for your scoreboard now. So, in short, you're not the star player anymore. You're the coach, you're the strategist, and you're the advocate. And the shift in that, that's the promotion. So now we'll spend some time talking through some core leadership skills needed, right? So when I was thinking what are there's so many skills that like good leaders need. How do I make it I don't have a slide debt big enough. So these are the four that I kind of

consider the foundation. If you do these four things and you're able to do them very well, then you have a higher likely of success in being a leader and serving as a leader in an organization. So starting with communication, right? Communication isn't just uh verbal. It's not just how you're able to deliver a message and talking to somebody on the phone, right? It's also written, right? And so it's adapting your message for the audience that's in front of you, right? So if you're a consultant and you deliver, you know, you did a web app pin test and you generate the report and then you deliver the report and do the readout call, right? There might be a

siso on the call. There might be an engineering manager. And there might be somebody from that team. Each three of those people are receiving the same message, but they're going to take away different things from that from that message. The syso cares about the overall risk. The engineering manager cares about the overall problems and the individual person may only care about a certain piece of it, right? But you have to be able to write that report so that all three of those groups are able to pull extract the information they need and then conduct actions on top of it. Right? And the only way you're able to do that is if you know your audience,

right? So when you think of the best or raators in history, right? You got Churchill, Roosevelt, Martin Luther King Jr., Lincoln. You know what do all these people have in common? They were all considered leaders of their time, right? And so in short, it doesn't matter if you have all the answers. If you cannot clearly articulate your message and thoughts so your audience can understand and act, your words are going to be useless. I don't care how good of a pentester you are or a redteamer that you are on my team. I don't care if you found every single vulnerability alive in an environment or on an application. If you can't communicate the risk to

your to the people that need to understand that risk, your efforts are useless. Right? So, uh next piece is delegation without micromanagement. Right? So delegation isn't dumping. Some people may think, "Oh, well, you know, my boss isn't going to take care of this and they're just dumping it on me and now I have to deal with it." Right? But really from a leadership side, it's not just dumping things on other people. Uh it's assigning outcomes. It's trusting people and you're getting out of their way to do what you ask them to do, right? Uh and so I encounter this a lot. Leaders today have too much to do and not enough time, right? I wish I had more time. I

wish there were 40 hours in a day instead of 24, right? But the only way that I'm able to actually achieve the things that I need to achieve at my level and my leaders at their level is they have to provide purpose, they have to provide motivation, and we have to provide direction. Right? Those are the three things that we owe our individual team members. Right? And so we discussed it on a previous slide, but you're paving a path and allowing others to struggle in a safe manner and enabling them to grow. You're giving them some left and right limits, right? You're not letting them drive the car off a cliff, right? But you got to you got to teach

them how to drive, right? You got to provide some coaching there. Uh, next one is decision- making under pressure. So, something I learned early in my career is the higher you go, the smaller that spotlight gets on you, right? So, when you're an individual contributor and you're standing on a stage with all the other individual contributors, depending on the size of the org and the function, you can kind of hide, right? But as you start to move up your leadership ladder, right, that circle gets smaller and smaller and smaller until possibly one day you're standing up there by yourself and there's nowhere to hide, right? And so, uh, something that I kind of coach my

team members through, my leaders through is there's a time to gather information, there's a time to debate, but ultimately there's a time to decide on the path ahead, and then you have to execute. And the I we'll get into this a little bit later, but newer leaders typically spend more time gathering information and debating instead of actually executing, right? So they spend all this time discussing and validating and doing all the things that they need to do, but then when it comes time to execute, it's like, I need this done by tomorrow or I need this done, you know, within, you know, an unreasonable time. Not saying that that's always the case, but I've seen a lot of new leaders make this

mistake. And so I when you do decide and execute on your own decision, right, it should be something that you truly own, right? Ownership is a huge part of leadership. You own the successes of your team. You also own the failures, right? It's pros and cons. The goal though is to have more successes than failures, right? Uh but I will tell you in my career when I have failed, I have failed spectacularly, right? I like I I failed like nobody has failed before, right? because if we're going to do it, then we're going to do it big, right? Uh so then the the the last one on this slide is giving and receiving feedback, right? A lot of

leaders think, you know, a lot of people moving into leadership thinks that they have to have all the answers. I'm here to tell you, you don't. I don't have all the answers, right? When I'm talking to my team, but and in that they have to be able to constantly give feedback. That is an expectation. But another side of that that I think some people might have problems with and I'm talking to myself uh is receiving and taking that feedback, right? Uh but giving and taking it is not optional, right? It's how your team improves and it's how you continue to grow and improve as an individual leader, right? So at the end of the day, your teams are looking for

you to guide and coach and train and mentor them. They're looking for you to hold them accountable and the rest of the team accountable to establish that standard and that baseline and everybody has to meet it. And then lastly is consistently provide feedback and updates on their performance. My company we use one-on ones and I use this very heavily. Uh it's a way that I can manage expectations but it's also another way that I can keep my finger on the pulse and enable the people on my team. Right? Okay. I constantly ask my my team members, both principal consultants that report to me directly and my managing and senior managing consultants, what can I do to help you? What challenges

are you facing today? What is it that I can do to enable you in your role today? Right now, I will tell you, I've already mentioned it, but I'll tell you again. I'd be a hypocrite if I told you I'm great at receiving feedback. Right? It's not easy hearing someone tell you where you failed or you've made a mistake or you didn't do something well enough. Right? And then if you ask my wife uh how good I am at receiving feedback, she probably laugh at you, right? So take away take away the professional in the personal life, every time my wife says, "You probably shouldn't have done that." I turn not nice, right? Uh but this is a

weak spot for me personally and it's something I try to work on every day. So how do I handle that? I try to remind myself that the person that is bringing me this feedback is not necessarily attacking me. the person, they're most of the time attacking the idea. They're attacking the behavior, right? And sometimes new leaders kind of confuse those two and they think they're attacking them, the person. And then that's one piece. The second piece is that we're all moving towards a common goal and that person is also trying to move towards that goal and they're calling out perspectives and they're calling out blind spots that maybe I didn't even know existed, right? And so

not all the feedback will be relevant. Not not all the feedback will be good, right? But the feedback is needed in your overall career growth. So this is a fun one. Leading former peers. Are there any leaders in here has had to lead people that were the homies? Right. Yes. Uh it is it is not fun. It's it's kind of weird, right? because it's like, man, I I was just hanging out with this person the other day. I were grabbing beers and now I'm this person's boss and I'm now responsible for their career, right? So, I mean, these are four things that I like tried to instill and try to narrow down like what can we

actually nail, right? And so, first you got to acknowledge the shift, right? Like I don't know, I'm somebody who just let's tackle the challenge head on. And so in this case, the the challenge is the elephant in the room, right? I'm now your boss and you have to listen. You have to do what I ask you to do as long as it's not illegal, immoral, or unethical, right? And so you I've seen some people be like, "Ah, well, nothing will change. Everything is good, right? But you're wrong. It will change because there will come a time where that person messes up and now you've got to go correct it." There will come a time for

promotions. There will come a time for payraises. there will come a time for evaluations, right? Where you have to be critical of this person, right? And so the longer you wait to have that conversation, the harder it is it's going to be for you, right? So, how can you do it? You just acknowledge it. Hey, I'm your boss now. We can still be homies. We can still be cool. We can hang out. Our families can hang out, right? We can play video games. We can do whatever, right? But when it comes to the business, you report to me. And and so it's not just from the leadership side to, you know, the individual contributor, the subordinate, right?

It's now to a place of there needs to be mutual respect between the two, right? And so, but it's not that person's job to tell you where the lines are. You have to have you have to tell them where the lines are. And in fact, I would take it a step further. You have to have the dialogue with them to establish the the the boundaries and where those lines are. Right? So uh the second one leading into that is set expectations early, right? Uh something that I try to do is I try to get away from ambiguity. I hate ambiguity. I hate gray areas and I like a playbook for everything. I like roles very clearly defined, very clear

expectations. And the way that we do that, the way that I found to do it is formal documents within the company. Right? Uh when I first came over to Net Spy, it took two and a half years, but we finally got role charters established that outline the responsibilities, the training, the expectations of a role for every single one of our consulting positions. This removes the need for me having to come up with this off the top of my head, right? And also, as your team continues to scale, I don't scale in that way, right? So the message I might deliver to one one person might differ from when I'm delivering the same message to another to another, right?

And so by having in this case having a workg groupoup established that you know is comprised of multiple cross functional teams that are having input and say into it once you get to a final document it's a hell of a lot easier to point to that and be like these are the expectations of your role and then at that point as a leader you can add to but you cannot take away from right. So that's I I try to you know it's our policy. I don't know to tell you here's where we are. Um you know it makes it a lot easier for your leaders to have those sorts of conversations right and so in that something too when you're

trying to lead uh your friends right uh don't assume that they'll read your mind right they're not going to know. They're looking for you to establish where those boundaries are that we already kind of already talked about. But you as a leader, you set the tempo, you set the pace of that conversation, right? Like that's your conversation to have. And then you have the burden of providing the clarity of how both of you are going to navigate, you know, this new dynamic that's there, right? So for me, fairness is everything, right? Favoritism, even perceived, will crush your credibility. If you lose credibility with your team, you've lost their trust. If you lose their trust, you're no longer effective.

it's just it's just not gonna happen, right? Uh and so by establishing those roles, by establishing those expectations upfront and then applying those expectations to the wider group, to your entire team, right? You're removing that bias. You're removing even the perception that, oh, that person just got promoted because they're friends with Leo. That person just got that pay raise because they're friends with Leo. That person was able to go to Bides because they're friends with Leo. Right? The moment that creeps into your team, it's poison and it'll run through your entire organization. Right? Last part. I tell all my new leaders this. Just because you're the boss now doesn't mean that you doesn't give you

the right to be a jerk. Right? You're not a dictator. I don't allow that to happen on my team. And in fact, in the training program that we've established for individual contributors coming managing consultants, uh at the six, it's a fourmonth program. at the six they're assigned uh three to four indiv uh consultants newer consultants to the org uh and their job is to effectively lead them right they're they're cutting their teeth on leadership on day one uh and so at the 60 and 120day mark when I built this program I established uh there's an there's a conversation that their direct leader will have with every single person individually where they're essentially grading that leader on I

think 12 topics right and they're asking these probing questions. Um, you know, it it spans from communication to morale, uh, to how well they feel their needs are met, right? Uh, it's through that not to get the leader in trouble, but it's meant to establish where that person needs to grow, where what are they doing that does not work. And the way that I communicate it to our team members is this is the one time that I want you to just be as hyperritical of this person as humanly possible. And this isn't you're they're not going to know you said it. We've got mechanisms in place to provide that anonymity, but I don't operate with them on a daily

basis. And therefore, I need to know where they're not succeeding and where they're failing because if you don't tell me, I'm not going to know. And you're going to feel the pain, right? And so because news flash, when you're done with the program, they're still going to be your boss, right? So now's the time to tell me. So because we're focusing on it, so I can help correct those behaviors. Right? So last part, it's a marathon and it's not a sprint, right? Don't fall into the friend trap. You're their manager now. It's your job to lead them and they're looking to you to provide that leadership. So next we'll talk about imposter syndrome. Who here has imposter

syndrome? Yep. Yep. I have it right now as as we live and breathe. Uh, and so, uh, you know, if you ever thought I'm not really a leader, like, welcome to the club, right? Like, I didn't think that either. Uh, especially being promoted in a wartime environment and now it's like, oh, this got real now. I'm responsible for these people's lives. Like, this is, and I think I was 20, 21, and I think I had five or six people assigned to me. Uh, but, you know, imposter syndrome is almost universal in first-time managers. I felt it. I'm sure many of you that are in leadership positions have felt it. And if you make a jump into leadership,

you too will feel it. Right? But what is it? Right? It's that voice that says you don't belong. It's a voice that says you're not good enough. Even when you do belong and when you are enough, you care and you're growing, right? And how do you combat it? Right? Well, the first thing that I always do is I get feedback, right? I ask myself why. I do the self-reflection. Why am I not good? Where do I think I'm failing? What where do I suck? Right? And then I write those down and then I go talk to my peers. I go talk to my boss. I get feedback from my direct reports and even their direct

reports, right? Because their opinions matter too, right? And I use that to challenge my assumptions to be like, "Oh, I didn't think I was good, but either everybody's lying or they think or I truly am doing a at least a decent job. Right? And so as individual contributors, success is clear and it's measurable. Right? As leaders, it's slow, sometimes extremely painful. It's messy and it's shared, right? But again, your successes aren't as a leader aren't really yours. It's the teams. It's not about you anymore. It's about your team, right? And then lastly, confidence, right? Confidence isn't a requirement for leadership, right? Uh it's a result, right? So, how do you gain confidence, right? How do you build to be, you know,

in your head when you think of a leader as somebody strong and resilient and, you know, willing to lead from the front and those sorts of things? Well, what I've learned in my career is it's knowing the material, knowing the environment, knowing the stakeholders, putting the time in to understand how things work and that sort of thing, right? So, uh, common mistakes leaders make, right? The first thing is uh trying to stay too technical. This is something that people most definitely love to be. They don't want to give up the technical work, but here they are, right? And so the way that I describe it is when you're an individual contributor doing technical work, you're sitting at 100%

and at 100% you were successful. But then you move into a leadership position and you're still trying to be technical while in a leadership position, meaning you're doing the job of somebody else while also trying to do your job. You're you the best you can do is 50/50 in either or, right? And then I would personally would rather take somebody who's a 100% good at one thing than 50% good at two things, right? Uh next is avoiding harder hard conversations, right? Like this is another thing that it's it's uncomfortable being a leader, especially when you have to let somebody go from a company or you have to tell them, "Hey, you're not meeting the standard." Right? But the way that I've

phrased that is you're not meeting the standard. Here's what you're doing. Here's where the standard is. here's how we're going to get you there. Right? Here's where we need to help you. Right? That's the second part. It's easy to call out mistakes. It's easy to call out when people are not doing what needs to be done. But it's even harder having to come up with a plan and a road map to get them there. Here's how we're going to do it. What do you think about this? Do you think this is feasible? How do you feel? Right? I might be wrong. Right? I might think that you're not meeting the standard when in fact you

truly are. Right? But again, I try to challenge those assumptions to make sure it doesn't happen. We've already talked about micromanaging everything. I think it's kind of agreed leaders don't have time to do it. I, you know, I hire adults. I hire professionals. Your job is, your job is to do your job, right? Failure to do so will result in negative consequences for you, right? Like at the end of the day, like I'm not trying to be a jerk, but that's just where we're at, right? So, when you're struggling, raise your hand. When you're needing help, raise your hand. when you need something, raise your hand, but failure to do those things, I I don't know. I'm not a mind reader,

too. Right? And then lastly is seeking approval over impact. So, new leaders often try to be friends with everybody, right? They try to be friends. They try to win people over in that regard. Oh, they're a friendly person, right? But, uh, people instinctly could take your kindness as a weakness, right? Oh, I don't have to go tell this person that I'm going to go do something because, you know, what are they going to do to me? yell at me, whatever, right? And so again, by setting those expectations early, by having those conversations early, by being the standard bearer and establishing those standards, right? You kind of help prevent all of that. So next is building your leadership style,

right? So this is the fun part. So how do you do it? Well, it starts with your values, right? So once your values is what is the core, it's what grounds you. It's what you feel is important versus not important, right? And then through your values, right, you'll learn to discover what are your strengths in enacting those things, right? You'll also discover what your weaknesses are, right? And so when you are discovering these strengths and weaknesses, right? Lean into your strengths, right? If you're great at talking to people, don't do a lot of your communication over written form, right? Go talk to people, right? Otherwise, you know, if you're I kind of tell my consultants this all the

time. It's like you've got to go do thought leadership things, right? blog posts on various topics, conference attendance, right? But some people were like, "I don't like public speaking." I'm like, "Great, go write something, right?" Or, "I'm a terrible writer." Great. Go speak. Like, I'm bad at both. Well, pick one and I'll help you. Right? That's kind of where we're at, right? And so from those strengths, like you'll lean into them. And then with your weaknesses, you also figure out these are the things that I need to work on, right? Uh lastly is the feedback. That's how you can also put that into, excuse me, that's how you can also put that into your strengths and weaknesses to

help figure that out, right? And then lastly, there's several frameworks out there that you can utilize. Servant leader, coaching, what's the other ones? Uh, situational leadership, right? But that doesn't mean that you fall in just one bucket, right? You you should be adapting and you should be changing your leadership style to the person that's sitting across from you. I've got people on my team that sometimes I'm slowing them down by, hey, let's do a one-on-one. And they're like, can we do like 10 minutes instead of like 30 because I got a lot to do, right? These are typically my high performing people and it's like, I just need to make sure you're good. Are you good? Not good.

How's life? You know, great. All right, get back to it. Right? I have other people that require a little bit more attention, right? They need more support. They need more coaching. Right? So, uh, the last part of all of this is if you nail all those things down, eventually you will come out being authentic. Your authenticity will be there, right? And so your lead, your team members will be able to snuff out when you're not being authentic, right? It's very important. All right. So, how do we lead from the long haul? Right? Well, the first thing is you got to set boundaries, right? You got to set boundaries in your work life. You got to set boundaries in your

personal life. The second thing is you got to invest in your team and you got to invest in yourself. Uh lastly is avoiding burnout and then planning for your long-term growth. And the way that you do that again is by feedback, grabbing some mentors, bouncing ideas off people, learning to grow, thinking about what your next steps are and then working towards those next steps. Right? So the key takeaways right leadership is not is a mindset shift. It's not a title. You don't become a leader when someone changes your job title. You become a leader when your focus shifts. You don't need all the answers. You just need clarity and intention. Right? You grow through the feedback, not

perfection. And you lead in a way that's authentic and sustainable. I kind of rushed through this last couple slides. I'm running out of time. Right. So, now we'll move into Q&A. And now I'm going to go into hot seat. Who has questions? Yeah. >> Oh, she's gonna help. >> Um, yeah. Thank you. This is not on. >> Okay. Uh yeah, this is exactly where I'm at. So I I appreciate the talk. Um so earlier in the the slides you were talking about um the the trap of I could do this so much better when you're looking at delegating. And so I was I was wondering, you know, that ties into the micromanaging of if you have a a

product, a deliverable for a client and it needs to be up to this standard, how do you >> like if if I could do it to, you know, 95% quality and then the person that I'm leading would do it to maybe 70% quality, how do you um how do you avoid micromanaging with the back and forth of this is how you need to do it. this is, you know, some of that's this is how I would do it. Um, but how do you effectively lead and and shape that person to be able to increase the the quality to what the expectation should be for the deliverable without getting into that micromanagy territory? >> Yeah, for sure. So, with any given task,

there's a time and a place, right? If the client is standing in front of me and they're like yelling at me, now's not the time to go allow a consultant to go and talk, right? like now I need to not push them aside but step in front of them and handle it, right? However, if you have a deliverable and it's not due for a week, that might be a good time to let them do that, right? And then maybe you're check, you know, it's Monday, you get the assignment, you check in with them on Wednesday, see where they're at. You might need to get your hands dirty a little bit because maybe there's a gap

or shortage there, but you're still enabling them, right? At the end of the day though, it's all about enabling your people and allowing them to grow, right? and what you don't you want to ensure that you're establishing the trust with them, but you also got to make sure the job gets done. So, there's a way that you can handle that. Whenever I find myself in that situation, it's like, "This looks really great. I'm going to bang out the rest, not because I don't trust you, but because this is due tomorrow and it's 5:00 and I got a wife and a kid and three dogs, right? So, I need to go take care of this." So, I you know, and then we'll do

an after action review after it, right? Here's the changes I made. Let's walk through it. Let's talk through it. You know, again, there's a you got to meet the deadline, right? Hope that helps, >> Leo. Great talk. >> Enjoyed it very much. Um, in the transition from going from technical to leadership, >> a lot of us may have apprehension about over time losing those technical skills. They're eroding as we're focusing on leadership. >> Yep. What type of suggestions do you have for that? >> Oh man, I'm in this right now. Um, yeah. So, it's about managing expectations with your boss, right? So, if you you should still maintain some level of technical knowledge because you're leading

technical people. You can't just ignore it, right? But at the same time, you kind of shift your focus to what is actually do I need to be doing? Is it my job to actually deliver the pin test or do I need to coach people on how to do the pin test? Right? And so uh but at some point your individual people are going through their journey as well, right? So you're not going to have all the answers. So you be like you need to deliver a pentest. These are the core areas of delivering a pentest. I challenge you to go figure out what these areas are. Right? Now when it comes to being personal and having to

maintain your own skills, manage expectations. I I'm one person. I got 90 people on my team, right? You're asking me to do a pin test. I will do the pin test. But if the client comes back angry, you can't yell at me, right? Uh I I haven't done a pin test in two years. Little rusty. I'mma grab people I need to make sure like double check me, fact check me, right? The people that I trust to know that. And I think when you do that, it shows humility. And I think it also shows that you trust those people that you grab because you're like, "Hey, go look at my work and like red ink it

up, right? I don't care what it looks like. I don't care like make it the best product possible because if it's not and it passes it, if I use my title and position to bypass the quality controls that we have in place, the client is the one that suffers and then you know I'm it's going to come back. The client's going to be angry. You know who's going to solve that problem? The problem's going to go to me, right? It's typically how it goes. And so I I was like, you know, I so I try to grab people that I trust that I know that are very knowledgeable that can just give me the cliff notes to do what I need to do to

enable me. Uh and then I try to establish that bar and then I grab those people early enough so that way in case I thought I hit the bar and I surely did not, you know, I got time to react to that. >> Yes, sir. >> Hey, I appreciate it. Great talk. Um, so I'm kind of at that point where trying to decide, do I still want to be a star player or do I want to officially make the jump into leadership? You had to wrestle with that. >> Yeah. >> How did you weigh that decision? How did you agree to give up being the star player? >> Yeah. So, I knew early on that I liked

being the guy in charge. Honestly, like if if I'm just being honest with you, I felt like I had a unique experience in the various units in the in the army I was assigned to, the various missions that we did, the operations I was a part of, that I brought a unique perspective uh that the average person did not. And so I wanted to take those skill sets and utilize those in a way that I can be a force multiplier across not just my company but across our industry and bring those insights to help other people be better. Right? And I found that I enjoy watching people grow and develop and do hard things because not

because of me but I enable them to do those things right. Uh I found more joy in that than wrecking a client's environment honestly. Like that's fun and that's great and that's cool that you're able to do all those things, but you're one person doing one task whereas I can have an impact. You know, there were 30 40 people in here. 40 people might become leaders today, right? So that's a that's a better that's a better way that I looked at it and viewed it. Uh but ultimately I like being the boss. I don't know. I like I like calling the shots. I don't like being told what to do. Honestly, I'm an Inagram 8. So, if

you don't know anything about anagrams as a naturalb born leader, like I'm all about justice and equality. Uh, and that's part of that whole thing. Uh, and so I just enjoy like being the guy. >> I get that. Thank you. >> Yeah, you're very welcome. >> Hey, a great talk. Thank you. Appreciate it a lot. Um, kind of all along the same lines. So, uh, you talked about how you were essentially thrown into leadership to a certain extent and then you learned that you liked it, right? A lot of times I think in the workplace um it looks like it's inevitable that I you've got to go from this individual contributor to leadership but that's not necessarily

the case. People have told me you know you don't have to build your career of like going to leadership eventually but do you think that that even if you are somebody who is an individual contributor I should be looking for opportunities to manage and try that out and be an individual contributor and try that out. I've had a lot of opportunities where I've been the guy with senior leadership being their technical hand and I also had an opportunity where I chose to try that leadership thing and sank instead of swam and learned that maybe I'm not that guy. >> Yeah. >> But what's your position on developing that those two prongs? >> Yeah. Uh so I man I whenever at my

company whenever I have people looking to move into a leadership position like my leaders tell me like hey this person's a good candidate we should go consider them. I personally go have a conversation with them and I give them the reality. I'm like all right so you want to move into a leadership role that's great but it's not the only step that you can take at this company. So why do you want to be a leader? Right? And there's no right or wrong answer to this, right? I'm just we're having a dialogue. And sometimes I find that, oh well, I mean, it's just the next thing to do. And it's like, okay, well, it's not the next thing to do. These are

going to be the expectations of you now. These are going to be the things that you have to do and and do well. You don't have to do it alone. You have an entire leadership team here to support you, right? But if you feel like you're doing it out of necessity versus you want to do it and you're interested in it, then you're probably not going to succeed. And so I'm somebody that if it's going to if the answer is going to be a no, I want to get to a no quick so we're not wasting each other's time. And again, just because I've had people be like, I see what you do. I don't want to

deal with people. I just want to go in a dark room in a corner and solve a hard problem. Perfect. There's a place for people like that. 100%. Right? So you don't necessarily need to feel like you need to move into leadership because there's no other avenue for you. I would say maybe your company, you should challenge your company and try to see is there other ways that you can leverage my skills and abilities to where I can have a greater impact on the organization, right? And if not and you're mastered your role and you're not feeling challenged, that might be an indicator that it's time to go find the next thing, right? Uh but at the end of the

day like I try very hard to make sure that we are my leaders know what's expected of them and they go in they go into the decision of yes I want to do this with their eyes wide open and also through the training program that we created at our company our people uh our team members are also like they get four months to cut their teeth and at any point they can remove themselves from the program. This isn't what I thought it was. I'm not really liking this. uh I want to go back to just being a consultant. That's okay. But if you get past that point and then you're promoted, then you're held to that

standard. And now if you can't meet that standard, which is what the program is supposed to be, if you can't meet that standard, then I have to hold you accountable just how I would hold any other managing consultant accountable, right? And so if it's not working, probably a PIP is going to have to happen. But again, that's a whole other topic. I don't really try, A lot of people view pips as I'm trying to fire you from the company. I view PIPS as I'm trying to rehabilitate you. I'm trying to get you to that place. I've tried the informal manner. It just ain't working. Now I'm going to try the formal manner. Right. Um and I view it as a good tool

versus a negative. Spot on. Thanks. Yeah.