Taking Control of Your Leadership Journey. Lessons From A Leader Who Got Himself Stuck ft. Mitch Greenfield
Alright. Thanks everyone. So this story is going to start in maybe a different place than you were expecting. Kindergarten. And you're probably thinking like, what are you talking about?
Mitch Greenfield:So I went to kindergarten twice. And I feel like that experience has changed me as a person in so many ways, right? The second time you go to kindergarten, they're like, you're gonna learn how to write your name. And I'm like, I got this. You're gonna learn your home address.
Mitch Greenfield:I got this. And I think it sort of set me up for this whole thing. My family's like, you never study. You never study growing up. And that just kinda set up my mindset I think for my life.
Mitch Greenfield:So maybe a different place to start. Oops. It carried on. My leadership some ways started at those two places. Like I grew up in New York, I've been in Louisville almost twenty years now.
Mitch Greenfield:But I worked at my dad's company when I was like six. Sorry dad that I'm outing you on video here. But I would take out the trash, I would file folders, I would do all those things on Saturday mornings with him. Then I worked at a camera store, which is maybe outdated now in so many ways, but I was actually doing digital restoration. So your really old family photos, I'd make them look good again.
Mitch Greenfield:But it was an interesting place. I was like 15, 16, 17 when I worked there. Pretty quickly I started closing the store by myself. Actually this is funny, as a security person now, so I couldn't close the store with my key code for the computer because I didn't have enough access. So my manager gave me his, which I have now memorized still to this day.
Mitch Greenfield:And it's my ATM because that number is totally unassociable with me in any way shape or form except if you know Mark. So yeah, that was an interesting one. So IU, that was kind of the next stop in my journey. And in college, I think I learned something that has benefited me my entire leadership career. And that was getting to know people, which is a common theme here today.
Mitch Greenfield:So I went to office hours, You go to some classes, there'd be really large classes. And would I consistently go to office hours. I wouldn't always have a question, sometimes I would just go say hi. This really benefited me when I was in graduate school. So I had a professor, it was my last course, my last final.
Mitch Greenfield:I got a 54 on the final. My last final of graduate school, A minus in the class. Because it validated my theory that relationships overpower everything else. So then the journey continued at PwC. I worked there for about a year.
Mitch Greenfield:Learned a lot about maybe how not to lead. About the experiences that didn't work for me. And then luckily enough ended up at Humana. I did pick the old logo on purpose because the Flying Man logo was the logo when I started almost eighteen years ago. So I started out as an individual contributor like all of us have.
Mitch Greenfield:And I just kept kinda doing things. So my first week there, this is a great story, I think everyone can relate to this. My boss was like, hey, we just bought this company, go do a review of them. And at the time my buddy Scott and I looked at each other and we were like, we got no clue what that means but we're gonna figure it out. So we came up with a plan and we went back and we said this is what we're gonna do.
Mitch Greenfield:We're gonna do an ISO 27,001 review because there was no NIST CSF. There was no high trust. Like none of these things existed to evaluate the security of a program seventeen years ago. And we're gonna do some technical testing. We're gonna scan their network for vulnerabilities.
Mitch Greenfield:We're gonna do web app assessment, you know, everything. We're gonna fire up Nessus, it's gonna be great. So we get their network diagrams before we go. We show up at this company, Comp Benefits, in Atlanta, Georgia. And Or Roslyn.
Mitch Greenfield:And we meet this guy, Tony. We sit down with him for a little bit and then we're like, yeah, we got your network diagrams, we got the scanner ready, you know, we're gonna scan the network. He's like, alright. So we set up the laptop and we go to lunch. Maybe not the smartest plan.
Mitch Greenfield:So about fifteen, twenty minutes later, Tony gets a phone call that the network crashed. And we're like, oh crap, what did we do? So we hurried back. Now the good part was, maybe, this was a vision company. So it was a vision lab, so all glasses and everything.
Mitch Greenfield:So thankfully the fact that we disconnected every phone call was not endangering people's health and well-being. So it turns out after some analysis they had a one arm DMZ, right? Which we didn't know from the diagram. So all internal and external connections went through the same firewall. We exhausted the firewall.
Mitch Greenfield:We ran out of open connections. They also had the idle timer set at one hour. So these idle connections were just not pruning and we exhausted the firewall. We dozed it, right? And that was fun.
Mitch Greenfield:So we figured that out. They made some changes to the firewall. We made some changes to our scanner to slow it down and next morning we came back and we're like, we're gonna do this again. And we crashed the network all over again. It just took a little bit longer this time.
Mitch Greenfield:So Tony was really mad at me for a long time, we're friends now. But I thought that was a really interesting career experience. This was like my first major thing at Humana, right? And I totally screwed it up. But we owned it.
Mitch Greenfield:We were like, hey, this is what went wrong, this is why it went wrong. We had the right intention, we were doing our job. But as we know as IT professionals, things don't always go as planned. So we had clear communication and, we're able to work through it. Then, wait, did one of the slides hold on, there we go that's the slide I want.
Mitch Greenfield:So in 2019 after I've at Humana for a while, we brought in the McChrystal Group. So if anyone is familiar with General McChrystal, he was a leader in Iraq during a really challenging time and was able to really turn the war around. Was able to turn around because a lot of his leadership mindset. So we wanted to learn from him. When he went into private practice or after his military career, went into private practice with his own consulting group.
Mitch Greenfield:So the first thing they run is a diagnostic. See, they're fancied at these military terms, they can't just call it a survey. So run this diagnostic and one of the questions in there is like, who do you get your information from? And at the time, I think I was an associate director. And my name kept coming up.
Mitch Greenfield:Like way more than they've ever seen. So they called me in and talked to me. And the guy who called me in is Billy Don. Talk about a great military name for a retired I forget his role, maybe he was a colonel but he was a great guy. Really cool, could still email him, he still emails me back.
Mitch Greenfield:But they called me in and they were like, Hey, we've never seen this before in any of the companies we've worked with. Someone positioned where you are but with that breadth of influence. And I really attribute that to networking. So I mentioned that I worked for my dad growing up, so maybe a unfair experience, but I attribute a lot of my leadership skill and communication to that. But the McChrystal Group, we talked some more and it really came down to I think a few principles for me that I with them of why people come back to me.
Mitch Greenfield:One is I answer every email every day, which I'm a little behind now. But even I was out yesterday and by the end of the night everyone was replied to. That doesn't mean I know the answers, right? But it means I know the right people to connect people to on my team or other teams. So I really have this strong belief that if someone emails me, like actually emails me, not talking about a mass email, but actually emails me for help, I got a reply.
Mitch Greenfield:I think that of sets me apart. Yesterday morning I sent to my teammates a team's message and I asked them a question and the answer I got back was I don't know. And that kind of pissed me off. I was like, that's the wrong answer? You can say I don't know but you have to tell me who to go to.
Mitch Greenfield:So talked after and the answer was like, Go to Nick. And I was like, That's a great answer. Right? Just because you don't know I believe that people respect you a lot more. I don't know is a great answer, but it's only great if it's followed with how to get the right answer.
Mitch Greenfield:That's another part of me. I'll constantly redirect people to the right people. The other thing that I told them at Crystal Group is if someone asks me a question and I don't agree with the answer, I'll help them fix it. So if I think our policies are bullshit, I'll say it. And I'll work with them to get the right answer.
Mitch Greenfield:Whether that's a policy exception or updated policy or clarification. But I believe that's another reason that people come to me. The other thing I've learned is I could do a lot more in the middle than I can at the top. So having that network of people that will come to you and work with you, that's how you get things done. And I think that's been something that has really benefited me throughout my career.
Mitch Greenfield:I don't know why I keep skipping that slide. So then this thing came along, right? We all remember this, COVID. And I remember at the time I had three mentors. One I didn't really like the most and two that I really respected.
Mitch Greenfield:But I view mentoring as very important, Just like coaching, I view it as a form of coaching. And so my mentors kept telling me to do something else. And I didn't want to listen. So now we're talking about being stuck. So I was doing security architecture at the time and I had done security architecture for about eight years at this point.
Mitch Greenfield:I went from an individual contributor to a leader and kind of moved up leadership titles on the team. And Jeff was part of my team for a little bit, that was a lot of fun, we had a great time. And I wanted to do more, I felt like I could do more. I felt like I can connect the dots, technology has been part of my life, my entire life. Started with an Apple IIe, I still have it.
Mitch Greenfield:I want to get my son to start playing on the Apple IIe, I think he'd love it. Who doesn't love Oregon Trail as a way to start your journey in life? But I felt stuck. Like I And I felt like I wanted to have a broader impact on the organization and I felt like I could. And a lot of my impact had been through these relationships.
Mitch Greenfield:I call it planting seeds. I'll plant a lot seeds with a lot of different people around the organization about change that I want to see whether it's technology or organizational. Sometimes those seeds grow, sometimes they don't. But the more seeds you plant, the more likely they are to grow. So that's another one of my strategies when I want to drive technology change.
Mitch Greenfield:I'll just start telling everyone, we should be doing this. We should be doing this. And they'll have to listen to my elevator spiel on why. So interestingly, all three of my mentors, right, they're like do something else. And I kept saying no.
Mitch Greenfield:Yet at the same time I was complaining about being stuck. But I kept saying no. And I kept saying no because I loved the people I worked with, I loved the partners I worked with, I loved the work I did. But the lesson that I wasn't seeing, that I now can see very clearly, was I viewed myself as an expert. And while I may have been, everyone else around me viewed it as, can you do anything else?
Mitch Greenfield:Eight years in one role, granted different titles but majority one role. The organizational question has to become, can you do anything else? Now there's an interesting story along the way. I did try to apply for another job one time at Humana, so I wasn't trying to leave. But at the time it was an IT M and A leadership position.
Mitch Greenfield:And based on how I started the story with security M and A, I did that for about five years, I thought, shoo in, great opportunity. At the time our CIO and CSO were like, Nope, you can't interview. We like you where you are. So that really pissed me off for a long time because I just thought that was a great role and a great opportunity and again to make that impact on the organization because that's what I like to do, I like to drive change. So that was many years before this.
Mitch Greenfield:So during COVID, I'm talking to my mentors and I'm stuck. One of them actually offers me a job on her team. It was a role that was open. We talked about it. She's like, Cool, you got it.
Mitch Greenfield:Can I go tell HR? And I was like, let me think about it. And the next morning I said no. And I said no because it was in a enterprise logging role. And I was like, I'm just not going to love that.
Mitch Greenfield:I'm a cyber security guy. Yeah And logging is adjacent but nowhere near is fun. So I said no. And yet continued to complain that I was stuck. So then an opportunity came along to leave Humana and I quit.
Mitch Greenfield:I told my boss, I was like, hey, I'm done. I was really fed up at the time. There was a lot of internal change which is a constant but a lot of change that I wasn't aligned with. And I actually talked to him. I remember these conversations.
Mitch Greenfield:I was walking the dog on a Friday afternoon and I talked to him and I told him what the other opportunities were. Literally, told him short of the company, what the role was, why I was interested in it, and had a very transparent conversation. And he didn't really say anything. So two weeks later, I texted him on a Sunday night and I was like hey, can we connect tomorrow? He's like actually I'm gonna be in Louisville.
Mitch Greenfield:Was like great, I didn't know. So we were in the same meeting and an IT strategy meeting which was very interesting. Not the meeting and mindset you want to be in when your outcome is I want to quit. So those were the most awkward three days of my life, I think, professionally. So we sit in this meeting and our first break comes up in the morning and I'm like, hey, we go talk out in the hall?
Mitch Greenfield:And he's like, yeah. So I'm like, I'm leaving, I took another job. And he was like, Totally shocked by it. Which I'm like, how could you be shocked? We had this conversation two weeks ago.
Mitch Greenfield:You shouldn't be shocked. I'm just doing what I told you I was gonna do and you didn't do anything any other way. So this was Monday, midday Monday. Tuesday, I bring in all my hardware, all my undocumented hardware and return it. And they're like, what, what is this?
Mitch Greenfield:I'm like, don't worry, it's really yours. Wednesday comes around and I email our CIO. I'm like, hey Sam, thank you, I appreciate your leadership and what I've learned from you but I'm taking another opportunity. And his reply is like, Let's talk. So I'm like, Alright.
Mitch Greenfield:I'm like, What do I have to lose at this point? I've got another job and I'm a New Yorker as I said so I'm pretty straightforward and transparent. I don't really hold much back. So we talked Thursday morning and I just laid out there like the changes I'm not aligned with and why. And then the conversation pivots into the opportunity I'm taking and we have a really great conversation.
Mitch Greenfield:Like a lot of mutual respect there around the role and why it could be good and why it couldn't be good. And he was like, What if we can change? What if there's another opportunity? And I was like, I don't know. At this point I was pretty checked out, right?
Mitch Greenfield:Mentally checked out of work. And by Friday night, I was an AVP. Now this was a really awkward time, right, because other people were watching this. And by the way, the hardware I returned, I never got most of it back. Like it got pillaged.
Mitch Greenfield:Like my chargers, I didn't get back. Was really frustrated by that. Because you know, a good charger is hard to come by, right? But that was awkward. Some of my peers at the time were like, I could go do this.
Mitch Greenfield:And I'm like, you can't. Like one other guy was like, can do the same thing. I'm like, you can't. You don't have the relationships. Fundamentally, these are relationships you need to foster and grow.
Mitch Greenfield:So that way when the time comes, can execute on them and take advantage of them. That wasn't my intent though. Intent was to be in a career place where I was happy and doing something fun. It was not to like sort of try to play them, if you will. But it worked out.
Mitch Greenfield:So I actually did some M and A work again there in that role. I was the Information Security Officer for Centerwell Home Health, which is Humana's largest acquisition ever. And spent about eighteen months, a little less actually, about a year working with them on transitioning their security program to Humana. And this is the last story I promise. So the last part of leadership journey for now, we'll see what comes next, is our SOC position opened.
Mitch Greenfield:And I was like, oh, that's an experience I want. But it's not a career I want. I don't want to live it forever but like I want to do it for a year. I want that resume builder, right, so I could go be a CISO. Because I felt like a SOC experience is really like the last thing I needed, if you will, to kind of put the whole book of work together.
Mitch Greenfield:So it gets posted externally, it gets posted internally, it's kind of wobbling back and forth. Then I talked to my boss, the same guy I had the conversation with before. And I was like, hey I want the job, I'm interested but I only want to do it for a year. And my pitch on only doing it for a year was then you could go hire externally. Right now the temperature is you can only hire internally, so I'll just be your filling guy.
Mitch Greenfield:A year from now, you hire externally, you're happy. I thought it was a great sales pitch, but I'm not a salesperson. So we had a conversation, he was like, you know that team's had a lot of change, this is gonna be the third leader in about four years. I can't really do that, I need someone like permanent. And I'm like, okay.
Mitch Greenfield:And just off the cuff, I'm like, what if we do an NBA style trade? And he was like what? And I was like yeah, know, like an NBA trade. You wanna make a change in IIM? Let's do it.
Mitch Greenfield:I'll lead IIM. Totally did not wanna lead IIM. It was nothing on my career desires or anything. Just kinda hit me in the moment. And he's like, that's interesting.
Mitch Greenfield:A week ish later he's like, alright, let's do it. And I'm like, shit, we're doing it? Okay. So here we are two years later leading IAM. So the last part of why I shared that last part of it was that's considered a lateral move.
Mitch Greenfield:Right? Like I didn't have a title change. In fact, you could argue my title went down because now I'm just AVP instead of a CISO. But I recognize in that opportunity Talk about one of the most critical business processes. Right?
Mitch Greenfield:Like if people don't have working identities, your whole business stops in today's world. It's a team of about 160 people. It's about a $33,000,000 budget. The team I led before was about eight people. The largest team I ever led before that was about 12 people.
Mitch Greenfield:And I was like, alright, let's do it. So it was a little scary. It's still a little scary. It's still a lot of fun but it's been a journey along the way. But I think the things that have always paid me well are trying to think big picture, tie things back to organizational strategy and network, network, network.
Mitch Greenfield:You never know when those connections will help you out in ways you didn't plan. And to me networking isn't always hey let's go talk. It's helping people, right? It's deeply helping people. That to me, the relationships you form by helping people are way better than the nonsense conversations you have in the elevator.
Mitch Greenfield:Obviously those are important too. But yeah, it's kind of how everything comes together. I've been doing I'm for about two years and I'm about to cross eighteen years at Humana. Most of this wasn't planned. I didn't plan to be there that long.
Mitch Greenfield:I've said for a long time as long as I was having fun, keep showing up. We've now established there was a period of not fun, where I decided I didn't want to show up anymore. But I think that's also part of a career, right? Every day, can't be fun. There are some days that are just work.
Mitch Greenfield:But yeah, that's my story. Hopefully there's some helpful tidbits in there.
Audience:Couple of questions. Yeah. 33 in your current team, are all those direct reports?
Mitch Greenfield:So my current team's 160.
Audience:Okay.
Mitch Greenfield:And I have nine direct reports.
Audience:Nine direct reports. At
Mitch Greenfield:one point I had 11 direct reports and that's just way too much.
Audience:Do you think you influence less across business units while you you manage and lead those groups? Or has that changed at all?
Mitch Greenfield:Oh, I think I still influence quite a bit. Yeah. I have the right relationships to text people and talk to them and reach out and just kind of share my opinions. But I also like to believe that I'm building other influencers along the way. Hopefully more better outcomes than social media influencers.
Mitch Greenfield:But encourage my people to challenge and have fun and share their opinions.
Audience:Great. Any other questions for Mitch? I've got one. Yeah. So you are the the leader probably the most get it done leader I've ever worked for, honestly.
Audience:Like, if you've ever worked with that person, somebody goes, oh, we'll we'll check-in with somebody, and we'll circle back. He gets right there while you're in the meeting clears the roadblock. Did you
Mitch Greenfield:get the And
Audience:things move in this group, which I love. How did you get the courage to do it? Because not everybody I learned a lot of that courage. A lot of the stuff I do now is because I've watched you do it and get away with it. How do other people do that in companies where it's not quite well regarded from security?
Mitch Greenfield:Just roll with it. You've to change culture one way or another. You know, I think maybe it's a little bit the New Yorker in me, like I said, just kind of being forward. But I've learned that sitting back doesn't get anything done. And the other thing I'll do But I think it's this sort of cross relationship of like, because I help people, I could bother people.
Mitch Greenfield:Right? So like, you know, get things done. I'm an inbox person. So as of this morning there are about 45 emails in my inbox. That's it, all read.
Mitch Greenfield:But like 45 things I need to follow-up on. Right? And one thing I've gotten better at in the last year is scheduling emails and scheduling Teams messages. Before I would just let them rip at like 4AM. And now I wait till about 8AM or 07:30 some days depending on how important it is.
Mitch Greenfield:That's been another thing. But I think it's also about finding that balance of when to push and when to let ride. It's kind of like a little bit of a gut on where I push and when. But I think part of the reason why I'm was attractive was that enterprise impact but also that need for change. So we've transformed the entire organization from an operational risk organization.
Mitch Greenfield:For the longest time, a lot of I'm teams were very operational risk managers in the sense that you need this access, we're gonna get you this access. There was not a lot of questioning of is that appropriate? We got the approval, it's cool, let's go. We followed the process, everything's fine. And I think we've started to change that mindset of like, is it the right access?
Mitch Greenfield:We've been very identity protection focused so one thing I'm excited about is I believe, and maybe some of the other security professionals out here will agree, we'll query Jeff in a second, I believe IAM is the only team that can protect the company. Right? That's a very bold statement. But think about it. Your SOC, they're the firefighters.
Mitch Greenfield:They come after the fire starts. Yeah, they monitor some logs and look for the smoke alarm going off. Overall, if I design my program correctly and structure it correctly and have the right conditional access policies and right identity threat protection, I can prevent a lot of bad things from happening. A lot of identity misuse, right? Identity misuse is every breach has a marker of identity misuse.
Mitch Greenfield:So that's been a large mindset shift in my team that I've tried to instill for the last two years is that we have to protect the company because we can protect it like no one else.
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