Episode 31 Leadership Lessons from a Mid-Level Bureaucrat

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Welcome to Executive Checkpoint, where security professionals gather insight to navigate the ever dynamic and changing world of physical and cybersecurity. I'm your host, Tino Urbina, and today I'm honored to bring one of our leaders in the industry, Christopher Stitt. He's the CEO of Crisis Lead and author of Scaling Pyramids: Leading Lessons from a Midlife. mid-level bureaucrat. He has 25 years of experience in federal law enforcement, diplomatic security, and crisis leadership. Christopher brings a powerful perspective on leadership, especially from the middle of a large organization. His book challenges the idea that leadership starts at the top and instead makes the case for influence, ethics, and impact. At every level. So Chris, I'm so glad you're here. Welcome to the show. Glad to have you.

Thank you very much, Tino. Fantastic to be here having a chat with you. I really look forward to the conversation that we're about to have and truly appreciate the introduction and all of your support.

Absolutely. So very excited to have you. And, you know, like we were talking about earlier, you're very accomplished now, author, communicator and speaker. But some people might not be so familiar with your background. Would you walk us through where you— what brought you to security, or in this case, your career in law enforcement, and just a little background?

Yeah, so for me, even growing up, protect and serve was something that I was very interested in. I was very interested in investigations, was intrigued by executive protection. different things like that. And as I graduated college and I went to work for the U.S. Capitol Police, I was planning to apply to the FBI when a friend of mine over lunch one day told me about the Diplomatic Security Service. And in short, I said, wait a minute, I can do investigations like the FBI, protection like the Secret Service, but my jurisdiction is the whole world? Where do I sign up for that? And Honestly, never looked back. Had a fantastic career. Um, I served in 5 foreign countries, uh, in a combination of Central America, Africa, and the Middle East. I traveled to about 40 others. Um, I was the regional security officer or chief security officer at 2 U.S. embassies, the deputy at 2 others, a senior manager at a 5th. Um, I finished my career as the Deputy Regional Director for International Programs, Western Hemisphere Affairs, so providing guidance and oversight to all of the embassies and consulates and the security programs there throughout the Americas and the Caribbean. I was also chief— you mentioned a little bit of crisis management, so I was Chief of Emergency Planning for the U.S. Department of State twice. So I actually rewrote the entire emergency planning handbook working across the State Department, the rest of the federal government, gathering lessons learned from private industry to create the policies and procedures that every embassy and consulate in the world uses to develop their emergency action plans, and oversaw the development of both generations of software that all of our embassies and consulates in the world use to take that enterprise-level policy and procedure manual and turn it into something that is viable, accurate, and usable for their operating context. Because let's be honest, your plan for Ottawa is not going to work in Ouagadougou. So we've got to be able to tailor it for them.

Yeah, and it's more, more mission-driven, right? For—

absolutely.

Yeah, it's not a budget, it's a mission. Yeah. And, and then, um, so now you move from your career doing that to today where you're running your own organization as the CEO. And how was that transition between the federal government and now private?

You know, it's interesting. So I retired from the federal service in April of 2023, but I still felt as though I had a lot to offer. And again, you know, service, protection, those kind of driving core parts of my being are really ingrained there. So I decided to open up my own consulting company. The other thing is, throughout my career, I learned that one of the things that really drives me is projects.

Sure.

I didn't want to go back into a job, you know, just join a company and be in a job where I'm doing the same thing over and over. I really like the variety, and I really like being a consultant where I can help different companies solve problems, work on projects for them, things like that. The transition itself was pretty interesting because You know, I knew a lot about security and crisis management and emergency management and leadership development. Did not learn— know a whole lot about running a business based on those things. But luckily, you know, through a group called the Kindness Games, and we can talk about that a little bit more if you'd like, and through just working on building my own network outside of the government, I found some really phenomenal mentors. who have really been very helpful to me. And, you know, honestly, it's one of the things I talk about in the book is that return on network investment.

Yeah, I saw that. I love that. And, you know, it's so important. We talk always about the money and the quantitative benefit of relationships, but in reality, that's the small price for sure.

Exactly.

Talk about the Kindness Games.

So the Kindness Games was kind of a movement that was started by Lee Otten and Tim Wenzel back in 2020, kind of the dark days of COVID if everybody hasn't blacked that out of their memories.

Oof.

And basically, it started as a conversation between the two of them where they were recognizing that they themselves and others were feeling kind of cut off and isolated. And, you know, they said the best way, you know, to improve your own mood is to help somebody else. So what if we started a process where we gave video shoutouts to people who have inspired us, mentored us, helped us along our journey, shown us kindness throughout our lives, and let them know that they're not forgotten about?

That's cool.

And it became a thing where they each wanted to do 30 of these. I think Tim and Lee have both done several hundred at this point, but other people started joining in and I was one of those. They started in early September of 2020. I jumped in in January of 2021, did my 30-post journey, actually had a bunch of us who completed that. I was alumni number 21. And a bunch of us who completed that 30-post process then banded together and we each wrote a chapter for the book, The Kindness Games: How a Single Post Changed Our Mindset About Community. These days you still see some people that are jumping in and going through their 30-post journey, but also it's kind of morphed into an organization that when there's, you know, a major conference coming up, Something like that. We'll have in-person meetups. But more than that, it's about helping the people, showing kindness to the people who maybe it's their first time at one of these conferences. They don't know how to navigate it. It's very, you know, vast. You think of ISC West, ISC East, ASIS, GSX. You can very easily get lost and spend a lot of time spinning your wheels and not accomplishing much. But if you got a good guide, you can accomplish more than you ever imagined. And one of the things that the Kindness Games does is it provides guides for those events and WhatsApp groups to help coordinate communication and things like that. So, you know, still going, but, you know, changing in different ways.

Yeah, I would love to, you know, I'm happy to promote this. It's a good deed and obviously has real value. Professionally and personally, it seems like to me. So let me ask you, what is it in your personal life and career that brought you to this conversation about your book? What's the genesis of the book? Tell us a little bit about that.

Yeah, so the book—

By the way, if you haven't taken the time— Yeah, there we go. Get your copy. It's really good. I, I, we were just talking about this and I'm an avid reader, by the way. Not, we'll go back to it, but, um, I really genuinely enjoyed reading it. It was easy to read and so much is, uh, I guess, um, I agree with a lot of it. And of course it's a guiding, there's guiding principles and align with my view of the world. So for that reason, I definitely wanna make sure to get that. But let's go back to you.

Yeah, no. So, so the book, you know, it's kind of funny. I wrote— I started the book about halfway through my career, and I kind of started as a cathartic exercise to 2 kind of poor managers that I had. I won't call them leaders. They thought themselves leaders, but more people fled them than were attracted to them.

Oof.

And, you know, I was— I was like, I know so much more about leadership than these guys that I could write a book. So I And, but part of it is, you know, and I mentioned to you, uh, this to you a little while ago, you know, never hit send on the angry email. Wait till the next morning.

Mm-hmm.

And the same thing with the book. I actually didn't hit send on it for about 10 years. And as I went through the process of writing it, uh, one of the things I did was I said, all right, so what were some good examples of leadership that I experienced in my career? And then I also reflected on, you know, some of my own personal values of explore, collaborate, teach. You know, explore new concepts and domains, find communities of purpose around those communities and domains to collaborate with, and then teach others what I've learned. And, you know, to me that was really important, and the book is one of those ways to go through and give that, you know, teach part of it. I was introduced to the concept of being a student of leadership by a couple of my role models and, you know, actively pursuing the growth mindset, actively pursuing learning about leadership. And one of the things that I saw is that there's a whole lot of information out there for the people at the top, right? How to be a better leader, how to lead your organization, you know, things like that. But there's not a whole lot out there for the people in the middle or at the bottom. And I really wanted to have this book be a resource for those people, because here's the other thing. Even though I never made it to the top of my bureaucratic pyramid, Big surprise here. I have not yet been Secretary of State, but, you know, I actually left the organization, retired from the organization in the upper mid-level.

Right.

But there's things that I was able to accomplish in there, changes that I was able to lead that have had an impact on the entire organization. And that's not just me. There's many other out there. Many others out there that have done the same thing.

Yeah.

So if you're sitting there in that early part of the organization, the lower levels of the organization or the mid-levels of the organization, how do you navigate that? How do you get your idea up in front of decision makers? How do you get people to follow your vision?

Sure.

Right. And that is a lot of it, what I wanted to share in the book.

Absolutely.

And of course, there's going to be myths, right, in mid-level leadership. So what are those that you want to push back on?

So I think, you know, myth number 1 is that leadership starts at the top, right? And quite frankly, leadership doesn't start at the top. It actually starts with you. It starts with you getting A vision, an understanding of yourself, building trust, building integrity, building, um, a sense that you have ideas that people are interested in and that they want to follow you, right? But to get there, you can't just show up one day and say, I'm going to be the leader. There's some followership skills that you need to learn and understand as well. In order to get there, you got to have a pretty good understanding of yourself, your influences, your role models, your values, you know, things like that. Um, and then once you're even in the position where you're actually leading people, you need to understand that different people have different motivations. They're not all the same. You need to understand what it is that the different dynamics of working in teams, working in groups. You need to be able to take some of the things you've learned and build the other leaders around you, because ultimately that is the goal, right? Not just to be a leader yourself, but to build the other leaders around you. And that's something I talk about in the book as well. Is, you know, in the job I was in, we rotated every 1 to 3 years. And there was kind of a little inside joke where, you know, I'd show up in a new assignment and say, hi, I'm the new Mary. Because we were just— it's a bureaucracy. We're kind of like cogs that get replaced in the machine. Some of those cogs function better than others. But when, when I would leave, somebody would show up and say, hi, I'm the new Chris. And until they actually got settled in and, you know, people learned their real name, right, you know, it was just kind of this easily replaced piece.

Right. And you know what, to me, to me, leading is— some people have that natural ability to lead, but some others are maybe not as empowered because background, because experiences, why not? I feel this is a good guide to take that wanting to and feel empowered to, you know, start with you and then influence the people nearby you, and then you're building this, this, this tribe. How do you see your book influencing professionals in the security and cyber industries?

So I think there's a lot of folks out there with some really great ideas. And what's really interesting is when you think about it, and we talked about leadership at the top, Before, but it's really the people on the ground, on that kind of line basis that are dealing with things every single day, that are the ones that actually come up with ideas. And part of the question then becomes, well, how do I get that idea in front of the decision makers? How can I actually navigate this complex organization So that I can turn my idea into a reality. And the book has a couple of different strategies to use in order to do that. And it also has a couple of different points that you need to consider about whether or not your idea is actually worth pursuing.

Right. What will be the top strategies then you will suggest to someone in that position, someone listening and going, huh?

So there's, there's 2 things. First of all, is your idea worth pursuing, right? And you got to understand the combination of the problem that you're facing, the solution that you're proposing, the timing of your solu— of your proposed solution, and the audience for your proposed solution, right? So what I mean by the problem and the solution, number one, is the problem Something is just annoying to you, or is it annoying to a whole lot of people?

Right.

Is the solution something that is going to be easily adapted, that is going to be embraced by a lot of people so you can get across the you know idea adoption curve, right? Or is it something that is going to make things even more complex and more difficult to deal with, and people are re willing to put up with the pain that they have rather than having to embrace new pain, even though if eventually your idea will make things easier, right? Then there's the timing, right? Sometimes a problem is only so big right now, but down the road, that problem may actually become enough of a problem to enough people that they'll want to make a change. So even if you've got the perfect solution right now, right now might not be the time to try and implement it.

Yeah.

Then you've got to consider the audience. How are you going to get it in front of the decision makers? And there's 2 strategies that I lay out in the book. The first is just 6 degrees of separation, sometimes known as 6 degrees of Kevin Bacon.

Right.

Who do you know that knows someone else that knows someone else that can get the idea in front of the decision maker? Now, in a bureaucracy, this may simply be pushing it up your own chain of command, but sometimes, for whatever various reason, as you push it up your own chain of command, it may stall. They don't have, you know, they're dealing with other things. They don't have time for your idea. They don't have time for your solution. So then in 6 degrees of separation, you know, how can you kind of go around the point where it is stalled? Or as I talk about in the book, you know, manage sideways first and then up. So who knows who That can say, hey, you know what? I'm hearing that somebody in your in your sub pyramid has an idea to solve this problem. You should really take a look at that. The other strategy that I talk about is frankly a grassroots campaign. Can you actually talk to others at your own level and say, hey, are you having the problem with this you know particular policy process whatever procedure as well? I have this idea that's a solution. If you get a groundswell of support for it, it makes it harder for managers above you to ignore.

Absolutely. So what do you think from a leadership perspective, someone that is sitting on the top of the pyramid looking at the book thinking maybe this is a good way to develop new leaders? What, what, what would be your conversation with someone sitting on the top of an organization referencing Your, your book?

Yeah. So I think, you know, it's actually a very useful tool to help leadership development throughout the organization. And part of that becomes what senior leaders need to understand is that while they're out there setting the vision and setting the direction, it's actually the mid-level leaders who are incredibly important in ensuring that that vision and program actually gets acted upon. And not only that, but it's those mid-level leaders that are interacting with the lower-level line managers and the staff themselves that actually hear what are the problems with the vision, what are the solutions that are potentially out there, what are the realities as they try to implement it on the ground. So making sure that you've done a good job of developing those mid-level leaders that have these skills to grow networks, to work in teams, to work to bridge the silos between the organizational units is incredibly powerful and useful to the thriving of the overall enterprise.

Right. Because you want to have people that follow operations systems and orders, but at the same time, you need them to have some level of initiative And, you know, so amplify, you know, leverage the existing potential leaders you have and empower them. That, that I really love that. What shift do you hope to see in organizations treating this as a good process, you know, with their mid-level leadership?

What I'd like to see, I think, is, you know, We talked about a little bit about bureaucracy itself. And as you just mentioned, you know, you've got to have the policies, the procedures, the standard operating procedures, you know, the chains of command, the chains of communication. But especially if you want your organization to thrive, what you've got to make sure that you're doing is always preparing the next generation of leaders. You've got to make sure that they are ready to step into that next level of responsibility and that next level of care for their teams. And more than that, they've got to understand not only what is their own tiny little pyramid that they're operating in.

Sure.

But they need to understand what— how their tiny little pyramid affects the operations of the larger pyramid. And the only way to do that is to actively engage in some cross-collaboration, to actively engage in some different project teams, to actually engage in discussion groups and personal development initiatives. So I think what I really hope to see that comes out of this book in the corporate world is a stronger recognition of that and some adoption of some of the principles in the book to help facilitate it.

Absolutely. So what, what would you like to see after someone finishes the book? The Monday morning after finishing the book, what would you hope the reader starts?

Or— So I would say if it is somebody who has no leadership experience whatsoever, right, I would hope that Monday morning after they start the book, they start with that section on leading yourself, and they start to really figure out what about them is valuable as a leader. What is their background? Who are their influences, their role models, their values, right, that they can then help to tell their leadership story. Then I would like them to start with the idea of leading others. How can they use some emotional intelligence, some kindness, some empathy to build the trust, to build their integrity? How can they make sure that as they make decisions, they reflect on the importance of integrity, and they reflect on the importance of what is good for themselves and for the organization and for those around them as they are working to actually make decisions, implement policies and procedures and things like that, and start to think, hey, is this the best way to do this? engage that creative mindset to try and figure out, are there better ways? Because while we gotta have the policies and the procedures and the SOPs and things like that in order to ensure the efficient operating of the organization, every good bureaucrat out there is always looking for ways to make sure there's efficiencies continue to improve. And quite frankly, in this era, With the rapid adoption of AI, with the rapid acceleration of integration of technology, that is way more important than ever.

Yeah, absolutely. And, you know, it gives a point of reference for some individuals that might have not seen themselves as leaders to instead have a nagging conversation about the things that are not happening because they have no control. Now they have at least something to lean in and say, okay, just gonna trust the, the, like you said, the, the trust the process and then start implementing that. I can see a lot of positive coming out of it too.

Absolutely.

So Chris, let me ask you, um, being in the industry for as many years and, uh, obviously now sitting at the top of an organization and accomplished, you know, author, why not? There's a lot of people out there that are At the beginning of their career, what would you tell your younger self at the beginning of your career that now you know that will definitely help younger Chris to achieve where you are, maybe more, who knows?

I would tell myself to surround myself with good people. Good role models, good inspirations, those that will speak truth into my life to help me, to let me know where I'm going wrong earlier in the process before I go way down the road. I've had some of those. I've had others that I wish would have said something to me sooner.

Sure.

And I would say, learn, grow. You know, you've got to— one of the things that has really benefited me is my continuous learning mindset. And one of the things that has, you know, really benefited me is my growth mindset. That here I am today, but this is not where I will always be, and I can continue to learn. I can continue to grow, and I can continue to achieve. Yeah, there's it's it's fascinating to me. There's there are people out there that all they want to do is their little thing, and. They're going to focus on that, and they don't want to be bothered with anything else. But when you talk to them in reality, they may want to focus on their own little thing in their job. But outside of their job, when you look at whole-of-person theory, right, they have many more things that are going on.

That's right.

So how can you encourage them to, you know, take that larger whole of person that they are and incorporate it into what they're doing so that they can grow— excuse me— their skill set, you know, within their job as well.

Absolutely. Well, Chris, I know we're coming closer and closer to the holidays. You were telling me it's already snowing back, you know, home. So that's more, more to the season, right? A little snow doesn't hurt. Where can people find first you professionally and then of course your book? Where can people get it?

Yep. So my company is Crisis Lead LLC, helping you navigate risk and prepare for what's next. That can be found at www.crisislead.com. They can certainly connect with me. I encourage people to connect with me and follow me on LinkedIn. I'm trying to put out some valuable content there that helps in the security, crisis management, and leadership spheres.

The—

you can contact me via email at cstitt@crisislead.com. I've also got, you know, since I've published the book, I've got an Instagram page. The book itself has its own LinkedIn page, Scaling Pyramids. There is a new website, scalingpyramids.com, which right now is just a landing page to help people find where to purchase the book. But it is going to be built out. I'm really excited about building out a lot of these concepts into speaking opportunities, training opportunities, workshops, etc., for corporate organizations that are looking for help developing their entry and mid-level leaders. So scalingpyramids.com, and then also about to be launched is christopherstitt.com so that people can find me for speaking engagements, executive coaching, leadership coaching, you know, different things like that. So a lot of different irons in the fire there, I know. But so Scaling Pyramids for kind of the leadership umbrella of things. I'm sorry, Crisis Lead for the leader, for the security umbrella kind of things, scalingpyramids.com, specifically about the book and training programs based on the book, and christopherstitt.com for engaging with me personally to speak at your event or, you know, help do some executive or leadership coaching for you.

Absolutely. Well, Chris, thank you so much for joining us and sharing your leadership journey. Your insights are a reminder of why it's important to continue expanding your knowledge. And here's a book that you should put on your bookshelf and read it, of course. So I will put a link to it.

Awesome.

So Chris, thanks so much. If I don't talk to you before the holidays, have a wonderful Merry Christmas and New Year. Maybe we have the chance to do that before that. But until next time, stay informed, stay secure, and we'll see you in the next one. The next checkpoint.