2886: Dr. Zero Trust on the Toxic Talent Dilemma: Leading, Not Bleeding

[00:00:00] In the rapidly evolving realm of cybersecurity where new threats emerge with each passing day,

[00:00:08] leadership within this sector has never been more critical.

[00:00:12] And yet it seldom talked about.

[00:00:15] And today I'm honoured to host friend of the show Dr Chase Cunningham.

[00:00:20] He's been on three times in the last five years, it's always a pleasure to get him

[00:00:24] on.

[00:00:25] He's not really the talk with me, but he's a luminary in the cybersecurity industry.

[00:00:30] He's effectively known in professional circles as Dr Zero Trust and he's had an illustrious

[00:00:36] career dedicated to fortifying enterprises against advanced security threats.

[00:00:42] He brings a wealth knowledge and unparalleled expertise to our discussion today.

[00:00:48] And in the past our discussions have been largely technical, but beyond his technical

[00:00:52] acumen.

[00:00:53] Chase has ventured into the exploration of leadership dynamics within cybersecurity and

[00:00:59] also aim to pinpoint some of the pitfalls that often beset organisations.

[00:01:05] And his new book which is a cracking read is called How Not To Lead.

[00:01:10] Lessons every manager can learn from dumpster chickens and mushroom farmers and other office

[00:01:16] offenders.

[00:01:17] And let me tell you in that book there are few familiar characters that you've

[00:01:20] encountered.

[00:01:21] I know what I have.

[00:01:22] But not only that there's also a lot of conventional wisdom by laying bare the leadership missteps

[00:01:28] of what we can all avoid.

[00:01:31] So Chase has got to come back on here today to not only enlighten but also to equip current

[00:01:36] and aspiring leaders with the insights needed to navigate the complex cybersecurity landscape

[00:01:42] effectively.

[00:01:43] So buckle up and hold on tight as I beam your ears all the way stateside when my

[00:01:47] good friend Dr Chase Conningham is waiting to join me again.

[00:01:52] So a massive warm welcome back to the show, Chase.

[00:01:55] For anyone that's missed our previous conversations and we always have a lot of fun, can you just

[00:01:59] remind everyone listening with a little about who you are and what you do?

[00:02:03] Sure.

[00:02:04] So I'm currently VP for security market research at G2.

[00:02:08] I'm a retired US Navy chief and I worked at the NSA for a number of years as well

[00:02:13] as some other government agencies.

[00:02:15] And in the meantime, I've written a bunch of books.

[00:02:17] You've released a couple of books.

[00:02:19] I think you're up to like eight now.

[00:02:21] One of the reasons I wanted to get you back on is your latest book offers a unique

[00:02:24] perspective by highlighting what not to do in leadership, not just cybersecurity.

[00:02:29] We're talking leadership here.

[00:02:31] So can you share the moment or experience that inspired you to take that unconventional

[00:02:36] approach to discussing leadership?

[00:02:38] Because I kind of got a feeling there's a story here too, right?

[00:02:41] Yeah.

[00:02:42] I mean, I would say I definitely wrote it with a little bit of a chip on my shoulder.

[00:02:45] There's always some catharsis to doing research and publication.

[00:02:48] But for me, because I consult and I work with so many companies, I've seen so many

[00:02:54] organizations where the people that are in charge honestly shouldn't be.

[00:02:59] And I've run into so many times where folks were just almost hell bent on

[00:03:04] wrecking the company with their leadership style.

[00:03:06] I was like, there's got to be a book about the failure side of this equation.

[00:03:10] And I read and researched and looked around.

[00:03:13] And I couldn't really find a lot that were vectored specifically to what you

[00:03:17] shouldn't do as a leader.

[00:03:18] And I just kind of took it on myself as well.

[00:03:21] If somebody's got to be the guy to jump on the sword, it'll be me.

[00:03:24] And I learned a lot as a great, great project to research and write.

[00:03:28] But yeah, it was definitely written with a chip on my shoulder.

[00:03:31] And the folks that are mentioned sort of conversationally in the book,

[00:03:37] they definitely know who they are, that they should do better.

[00:03:40] I love it.

[00:03:43] And dumpster chicken and mushroom farming of vivid metaphors in the book

[00:03:48] that you described to what you used to describe certain leadership failings

[00:03:52] that you've encountered.

[00:03:53] So for people listening that have not seen the book, I don't know what to expect.

[00:03:56] Can you just explain the significance of those terms

[00:03:59] and how they encapsulate some of those common leadership pitfalls

[00:04:03] that will resonate with people listening all around the world?

[00:04:05] Sure.

[00:04:06] And I mean, we've all run into these sort of leadership styles.

[00:04:09] So dumpster chicken and the Navy we called seagulls,

[00:04:12] dumpster chickens because that's kind of where they were all at.

[00:04:14] And if you ran out of food, eventually you might have to eat one.

[00:04:17] I wouldn't recommend it, but it's possible.

[00:04:18] And the truth of the matter when you're looking at the leadership style

[00:04:22] is these are the folks that they kind of fly around squawking about things

[00:04:25] and then they'll land and they'll crap all over the problem

[00:04:28] and then they fly away and you're just sitting there going like,

[00:04:30] how was that helpful and why didn't you assist me really solving this problem?

[00:04:34] And that that's not something you want.

[00:04:36] It doesn't help.

[00:04:37] Some people call it like helicoptering or whatever.

[00:04:39] But I think the fact that people do this is still very troubling.

[00:04:44] And then mushroom farming, we've all been here as well

[00:04:47] where you keep your people in the dark and you feed them crap

[00:04:50] and hope that they figure things out on their own.

[00:04:52] There's a couple of problems with that.

[00:04:55] One, the mushrooms will actually communicate

[00:04:58] and that's where you get these gossip problems.

[00:05:00] And then two, people start to wonder why you're not telling them

[00:05:04] the whole story and the last thing that you want in a leadership position

[00:05:07] is people guessing what's going on.

[00:05:10] It's better to keep them informed and educated

[00:05:13] and be honest with your folks if you can trust your workforce

[00:05:16] to to empower them with knowledge.

[00:05:18] Why are they your workforce in the first place?

[00:05:21] And I really hope that people can tell just by listening to our conversation today

[00:05:25] that this isn't just another one of those throwaway business or leadership book.

[00:05:30] It is very straight talking and a certain amount of humor in there.

[00:05:33] And you discussed the concept of falling from your ego

[00:05:36] and hitting your IQ on the way down.

[00:05:38] So how does that phenomenon manifest among leaders?

[00:05:42] And why is it crucial for them to recognize and address this?

[00:05:46] We might be able to speak to some of those leaders directly into their ears, right?

[00:05:50] Yeah, I mean, it's interesting because in technology,

[00:05:52] we have this kind of weird phenomenon

[00:05:55] that you don't see in other organizational structures

[00:05:58] where someone can come out of college and they have a good idea

[00:06:01] and they can write code or something like that.

[00:06:03] They're very technically adept and they start building something

[00:06:06] and before they know it, they've got DC funding and they're in charge

[00:06:09] and they never wanted to be a leader

[00:06:12] and they never knew how to be a leader and they're up there

[00:06:14] because they're super smart.

[00:06:16] Usually the problem with that is typical type 8 sort of activity.

[00:06:21] They get pretty high on their own supply

[00:06:23] and they're really thinking that they are the best thing since sliced bread.

[00:06:27] And then they don't understand why everyone is not accepting

[00:06:30] of the same standard or the same operational leader, whatever else that they have.

[00:06:34] And they need to get knocked off that pedestal.

[00:06:36] And honestly, it's detrimental to the business and to the employees

[00:06:41] to deal with those types of people.

[00:06:43] I think Netflix has a really good book that they had somebody

[00:06:47] write called The No Asshole Rule and it's very, very applicable here as well.

[00:06:53] The book also mentions three non-negotiable currencies

[00:06:57] that every leader must have.

[00:06:59] Can you elaborate on these currencies and why missing even just one of them

[00:07:03] could be detrimental to a leader's effectiveness, not just in tech but in any business?

[00:07:07] Yeah, it's a three-legged stool and my research

[00:07:10] uncovered this that it's really time, trust and respect.

[00:07:13] And what we mean by time is if you're in charge,

[00:07:16] you should really think about the currency of time, not just time as a thing,

[00:07:21] but the currency of it.

[00:07:22] And everyone here on this planet only has a certain amount of time allotted to them.

[00:07:26] It's just the reality of where we are.

[00:07:28] And any time that you as a leader are coming up with things that are taking people's time away,

[00:07:33] if there's not real value to it, you're literally robbing them of their time on planet Earth,

[00:07:38] where they could do other things.

[00:07:39] And that filters its way into a lot of organizational structures.

[00:07:43] You see it where organizations will have in the military,

[00:07:46] we used to call it mandatory fund.

[00:07:48] Nobody wants to be there.

[00:07:49] It's a waste of time, but people show up because the boss says so.

[00:07:52] And it just eats away at the spree decor and all those other things.

[00:07:56] And then that filters into the trust and respect side of if you're stealing my time,

[00:08:03] I'm going to lose my trust that you actually care about me as a person.

[00:08:06] And by that factor, I'm going to stop respecting you.

[00:08:10] So these things are dependent on one another.

[00:08:14] And really leadership in my opinion should look at these as currencies in the bank.

[00:08:18] And if you're not investing in those currencies, you're taking away.

[00:08:21] And sooner or later, the bank total comes to zero.

[00:08:24] And I think even though it is what nearly 5,000 miles difference between is and everybody listening

[00:08:30] around the world.

[00:08:31] One thing that we're all sharing common is we've all had to deal with difficult people.

[00:08:35] And I think very often this such a big focus on the next shiny big new technology or shiny

[00:08:41] big new solution, but we don't focus on the culture and people in your book.

[00:08:46] One of the areas that you deal with as well is dealing with as you turn the brilliant jerks

[00:08:51] and it's a challenge that you address.

[00:08:52] So what strategies do you recommend for managing highly talented but equally

[00:08:57] occasionally toxic employees without stifling their creativity or or harming overall team

[00:09:03] morale because it's quite a balancing act, isn't it?

[00:09:06] Yeah, it is.

[00:09:07] I think one thing to be really careful of is those folks that do display those types of

[00:09:12] tendencies should be seriously evaluated for leadership roles.

[00:09:16] A lot of times they kind of wind up in them and they would tell you that they don't

[00:09:19] want to be there but they like the kind of ego bump of being in that spot.

[00:09:24] It's not that they're actually enjoying it or necessarily that they're good at it.

[00:09:27] The reality of what you're talking about with a brilliant jerk is they can be very,

[00:09:31] very valuable.

[00:09:31] They can do awesome things for the company.

[00:09:34] They can grow revenue and all those aspects.

[00:09:36] But many times the business, the people, the culture, the entire organization would

[00:09:42] be better if you just kind of put them in their own space and let them do their thing

[00:09:47] and weren't using them as a go-to market or somebody that's out there as an evangelist,

[00:09:53] whatever like that is not their thing.

[00:09:55] They don't enjoy it and honestly they're usually the type of people that don't do

[00:10:00] well interacting with a lot of folks so don't make them.

[00:10:03] It's not going to help anyone.

[00:10:06] And your extensive background in cybersecurity and leadership, I think it uniquely

[00:10:10] positions you to speak about everything we're talking about here especially around

[00:10:13] the intersection of technology and leadership.

[00:10:16] So I've got to ask, how do you see the evolution of leadership in the tech-driven world

[00:10:21] especially with the rise of remote work, hybrid working, digital communication tools,

[00:10:26] everyone going all in and AI and everything?

[00:10:28] How do you see this space evolving?

[00:10:31] Man, I think really what we're getting to is a space where we should be allowing

[00:10:34] the organization and the people to kind of grow organically instead of trying to force

[00:10:40] folks down different roads towards a future that is determined by a spreadsheet or past history.

[00:10:47] If your people do great working remote, let them work remote.

[00:10:51] If they do better whether in an office then bring them to the office.

[00:10:55] If they need more time, work with them to get that time and make it available.

[00:11:00] There's in today's world with all the technology that we have and all the capability that every

[00:11:04] single person has, I don't think that we should be trying to pigeonhole people based on past experience

[00:11:11] and on kind of the current understanding and thinking of what the market says has to happen.

[00:11:16] It is detrimental to the overall efficacy of the org and that's not what you want as a business

[00:11:23] leader. You want growth, you want happy people, you want operational capability.

[00:11:28] Doing things the way we did even five years ago is not a good way to do things.

[00:11:32] At the start of our conversation today, you were talking about your own book with somewhat of a chip

[00:11:38] on your shoulder, right and a few wrongs and all the things that you'd seen throughout your career.

[00:11:43] But the book also does include some real world case studies of leadership disasters.

[00:11:49] I don't want to give away too many spoilers here in this podcast for people who are going to

[00:11:52] check that book out. But can you share maybe an example and the key lesson that it might offer

[00:11:58] to current and aspiring leaders too? Yeah, I think one of the ones that stuck out to me and I

[00:12:03] never known this was everyone looks to Steve Jobs as the guy that kind of reinvented Apple and he did.

[00:12:09] But what you probably don't know is that when Steve came back after he was fired by the board,

[00:12:14] he came back from next computer's part of what he looked at was the P&L of the company and

[00:12:20] the current structure of the products that they were pushing. And he actually went up

[00:12:24] and drew a quadrant on a whiteboard and said, here's the four things that we're going to do.

[00:12:29] Any product that we have, and I think at the time Apple computers had like 37 products,

[00:12:33] he said anything that doesn't fit in these four quadrants is done as of today.

[00:12:37] And that sounds like a woe type of moment. But what he really did immediately was

[00:12:43] was move efficacy towards profitability. And it changed Apple computers. If he hadn't

[00:12:49] done that, Apple computers probably wouldn't exist as it does today.

[00:12:54] Wow, incredibly cool. And arguably could fit into the brilliant jerk category as well, right?

[00:12:58] Oh, he definitely was a brilliant jerk. Yeah.

[00:13:01] And finally, for anyone listening looking to reverse negative leadership traits or maybe

[00:13:06] avoid developing them in the first place, I think self-awareness is such an important

[00:13:11] trait. But what initial steps or mindsets ships do you think that they should embark

[00:13:15] on their journey to becoming more effective leaders and not make so many of those mistakes

[00:13:20] or end up appearing in your book? Yeah. I mean, I think really what there's a

[00:13:25] chapter I had in there about the types of lenses you should look through and the biggest one in my

[00:13:29] opinion is the lens if you will of the mirror. If you wouldn't work for you, why would somebody

[00:13:35] else? And if you look at yourself in the mirror and actually go, am I the one who should be

[00:13:40] running things? Am I doing things for the good of the cause? And is my ego the issue?

[00:13:47] You should know more about you than you do about everyone else. And that,

[00:13:50] I find that to be difficult for a lot of folks, especially people that are in leadership positions.

[00:13:55] It's never comfortable to look at yourself in the mirror and go, you know what,

[00:13:59] I might not be the person that's best for this, but I can make things better by choosing to

[00:14:05] figure out a different way, even a different person to do this. And me, like I run my

[00:14:09] own organization, I don't seek leadership roles. It just is, I think there's people

[00:14:15] that are better suited for it. And that's a key thing that you have to keep in perspective.

[00:14:21] Now, before I let you go, I think the pace of technological change at the moment can feel

[00:14:26] incredibly overwhelming. There's a real pressure on everyone to be in a state of almost

[00:14:31] constant continuous learning. So as someone that has got his own company, he's written eight

[00:14:36] books. You're always pushing the boundaries of technology and you've got your eye on the next

[00:14:40] big thing and future threats, et cetera. I've got to ask, where or how do you self educate? Because

[00:14:47] it's very challenging for a lot of people, but you seem to have mastered this. So any tips

[00:14:52] or advice you can share on how you keep up to speed with everything? Well, I'm a long way

[00:14:56] from mastering, but I definitely, I try and stay engaged. I think I actually didn't like Audible,

[00:15:02] but I'm a big fan of Audible now just because I can listen to the books while I'm reading or

[00:15:08] driving or on a plane or those types of things. But I've also found that it's very valuable to set

[00:15:13] a goal for the year of how many books I'm going to read and then vary what I'm going to read by,

[00:15:20] I don't stick into the same topic twice if I read one book about leadership, the next

[00:15:25] one's about finance. So a lot of folks would do well to expand your horizons and

[00:15:31] the way things are today, it really, there's no excuse not to continually learn. So I would just say

[00:15:38] stay engaged and pick your kind of level that you're willing to operate at and then do it.

[00:15:43] It's not that difficult. Just make it happen. Love that. It's been a huge pleasure as always

[00:15:49] having you on the podcast. We've talked about everything over the last few years from cyber

[00:15:54] security to technology to now leadership. Anyone that would like to check out your

[00:15:59] current book or indeed check out your back catalogs, you've got another seven out there as well.

[00:16:03] What's the best starting point for everything? Yeah, everything I've got is on Amazon like

[00:16:08] everybody else. So I would say check out there. This last book was published by Wiley W I L E Y

[00:16:12] publication. So if you're looking for that one that's there and then we do have an Audible

[00:16:17] version and I'm actually working on it, an Audible version recording with my own voice

[00:16:21] because it was my book. So I'd love anybody to check the book out and please provide me

[00:16:26] any feedback you have. Oh, I'll be checking that out. I must admit it makes a huge difference

[00:16:31] when you listen on Audible when it is the order the actual author and not just some actor guy

[00:16:36] somewhere it makes such a difference. It feels so much more authentic doesn't it when you listen?

[00:16:40] Yeah, to me it's way more engaging.

[00:16:44] Well, absolutely love chatting with you. We covered so much again. Anything else coming

[00:16:48] out on the horizon? Is there a book number nine or have you just you scratch that

[00:16:53] edge and you leave it alone and walk? I'm taking a little bit of a break from

[00:16:56] authorship right now. But you know, there's always more in the tank what it amounts to

[00:17:02] I don't know yet but eventually I'm sure I'll crank out another one.

[00:17:05] I'm sure you will and I'll be waiting to get you back on here to learn more about it. But as

[00:17:09] always Chase thanks for joining me today. Hey thank you love it. I think it's clear isn't it that

[00:17:14] the journey to exemplary leadership in the cyber security sector or let's be honest

[00:17:18] any field for that matter is fraught with challenges that demand not only technical prowess but also

[00:17:25] profound self awareness and a dedication to continuous improvement. And I love how Chase

[00:17:32] brought it to life today with his vivid metaphors and candid exploration of leadership missteps

[00:17:38] and ultimately helping provide a compass for anyone navigating the stormy seas of management

[00:17:44] and offering actionable strategies that foster an environment of trust, respect and efficiency.

[00:17:52] Sounds simple right? And I think as we close today's episode we are reminded that the path to

[00:17:57] leadership is not about failing it's about learning from it embodying the key currencies

[00:18:03] of time trust and respect and most importantly having the courage to lead differently. But hey

[00:18:09] I'd love to hear your thoughts on this one. Have you come across any dumpster chickens and

[00:18:13] mushroom farmers in your office? Or brilliant jerks? I suspect you have. I'd love to hear

[00:18:18] your stories if you don't want to share them with me on the podcast. Feel free to slide into my DMs

[00:18:24] on LinkedIn, Twitter and Instagram I love a good gossip because you can find me just at

[00:18:28] neil chews or email me techblogwriteratoutlook.com because the conversation doesn't stop here.

[00:18:35] Let me know what steps you would take to transform your leadership approach

[00:18:38] in the face of evolving threats and opportunities and an increasing pace of technological change.

[00:18:45] But that's it for today so I'll be back bright and early tomorrow morning we've got a completely

[00:18:50] different topic today I can't tell you what that is but if you join me I'll tell you all about

[00:18:54] it. So thank you for these figures always and until next time don't be a stranger.