G-9J8XZFK1NF Breaking into Cybersecurity Leadership - Jeffrey Wheatman - Breaking Into Cybersecurity

Episode 2

Breaking into Cybersecurity Leadership - Jeffrey Wheatman

Breaking into Cybersecurity Leadership - Jeffrey Wheatman

Jeffrey Wheatman on LinkedIn - https://www.linkedin.com/in/jnwheatman/


Sponsored by CPF Coaching LLC - http://cpf-coaching.com


The Breaking into Cybersecurity: It’s a conversation about what they did before, why did they pivot into cyber, what the process was they went through Breaking Into Cybersecurity, how they keep up, and advice/tips/tricks along the way.


The Breaking into Cybersecurity Leadership Series is an additional series focused on cybersecurity leadership and hearing directly from different leaders in cybersecurity (high and low) on what it takes to be a successful leader. We focus on the skills and competencies associated with cybersecurity leadership and tips/tricks/advice from cybersecurity leaders.


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_________________________________________


About the hosts:  


Christophe Foulon focuses on helping to secure people and processes with a solid understanding of the technology involved. He has over ten years of experience as an experienced Information Security Manager and Cybersecurity Strategist with a passion for customer service, process improvement, and information security. He has significant experience in optimizing the use of technology while balancing the implications to people, processes, and information security by using a consultative approach.


https://www.linkedin.com/in/christophefoulon/


Find out more about CPF-Coaching at https://www.cpf-coaching.com


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Mentioned in this episode:

CPF Coaching: Cybersecurity Leadership and Talent Development Consultant

CPF Coaching: Cybersecurity Leadership and Talent Development Consultant

Thank you to CPF Coaching for Sponsoring

Transcript
Christophe Foulon:

Welcome to another episode of Breaking into Cybersecurity

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Leadership, where we talk to leaders

within the cybersecurity field to

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learn about the skills and competencies

needed to develop the next generation.

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Today we have Jeffrey Wheatman,

who's on the show, and he'll

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be sharing his insights.

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On what it takes to become a great leader.

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But before we get there, this is a

reminder to share this episode and

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others, with anyone that's interested in

breaking into cybersecurity or breaking

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into cybersecurity leadership so that

they could see the different skills,

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competencies, and approaches that'll be

successful in advancing their career.

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Jeff, before we jump in, give us a

little bit of background about yourself.

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Jeffery Wheatman: Yeah, absolutely.

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Hey, Christophe, how are you?

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It's a pleasure to talk to you again.

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So I have a little bit of an interesting

career in cyber because I actually

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started out, believe it or not, in retail.

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I managed a hardware store in

New York City when I was, when

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I first got outta college.

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You know what?

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But I hated it.

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I hated being in retail.

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I hated I hated that whole thing.

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And I, and

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so I put myself through a training.

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I'm dating myself.

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I got certified in Novell

Network three point 11 to show

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you how long I've been around.

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And I did a bunch of technical

things and between you and me and

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all the people listening, I was never

super great at a technical person.

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But what I.

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To.

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So that's really driven

a lot of what I've done.

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When I finished my, my network

certification, I actually

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went to go work for a company

that installed color printers.

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I ran a team that installed these

raster image processors that were

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built on the old Silicon Graphics

pizza boxes, if you remember those.

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Flat blue things.

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I sorta, I moved around quite a bit.

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I ended up in consulting where I ran a lot

of teams and I built consulting practices.

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I ran security and network

operations for Martha Stewart in

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New York City for a number of years.

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And before anyone asked, yes, I was

there during the investigation, I was.

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The thing that was super interesting

about that is back then the lawyers

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didn't have paralegals that knew

anything about cybersecurity or tech.

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The FBI didn't really know a lot about it.

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They didn't know about things like

MD five checks, sums on files.

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I sent them files and I sent them all

the MD fives and they said, what's that?

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And the response would.

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I went, oh, okay, I'm gonna,

I'm gonna keep this here.

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And I did that for a while.

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And then I went and I built another

I built a consulting practice.

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I had my own company for a little

while, and then I, stumbled into

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the job at Gartner where I had

the opportunity to work with.

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Tons of Fortune 1000 CISOs and Chief

Risk Officers and CFOs, and I learned

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more about leadership and managing

people and working with people from

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watching other people do it and seeing

what worked and what didn't work.

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And I did that for 15

years and I love that job.

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I love the.

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At Black, I.

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And now I'm closer to the problem.

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So we work in the third party

risk intelligence space.

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And I work with a lot of CISOs.

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I work with a lot of people in sourcing,

procurement and vendor management.

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And one of the things that I do

a lot of with them these days is.

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I help them engage with their non-IT

non-technical partners where people

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tend to struggle when this gonna a,

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and they had two breaches,

very significant breaches.

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The CISO got fired.

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The CEO got a raise and became

the chairman of the board.

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They put out their annual report.

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They didn't talk about cybersecurity risk.

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Yes, they railroaded the ciso,

but at the end of the day.

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Did the CISO do a good job

of communicating the business

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impact of those cyber risks?

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And they probably did not.

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So that's kinda kind of my story.

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I love to talk to people about coaching.

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I love to mentor people.

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And I'm a big fan of helping

people become people, become

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leaders as opposed to manager.

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Christophe Foulon: Yeah, absolutely.

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I think helping new leaders switch

from a tactical hands-on approach to a

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more strategic holistic approach when

working with the business is critical.

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I.

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As they move up, but

let's take a step back.

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In your career, you pivoted from, at

some point, from being an individual

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contributor to starting to lead teams.

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whAt in you decided that you really

wanted to lead teams versus just

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controlling your own workload?

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Track 1: That's a great question

and I think it's I'm gonna

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paraphrase a famous quote, right?

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Some some people seek out

leadership, some people have

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leadership thrust upon them.

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And what happened was people

started coming to me and asking

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me, Hey, how do I do this?

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Or struggling with this?

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There I have conflict with someone on my

team and I just really started doing a

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lot of the things that leadership does.

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And when when the leadership role opened

up it, I just stepped into it without even

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really thinking about it, and they did

gimme more money so that, that was good.

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But what I realized was I enjoyed

mentoring and leading and working

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with teams and building teams, and.

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As much, if not more as doing

pen testing and doing incident

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response, because those are a couple

of things that, that I was doing.

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I got more satisfaction outta it

and it, that just propelled my

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career and I'm proud to say I've

had a number of people that have

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worked for me in more than one role.

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And a very good friend of mine told me,

and I almost cried when she told me this.

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And she's a partner at one of the

big big four consulting firms.

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She said, everything I learned

about managing and leading

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people, I learned working for you.

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And she worked for me 20 years ago

and she told me this last month.

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I love that

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something.

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Christophe Foulon: You

already started to answer.

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The next question is, what are some of

the critical skills and competencies

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needed for a cybersecurity leader today?

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I.

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Jeffery Wheatman: All so that, there's

a lot, but we only have limited time.

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So I would say three or four

of the key ones, I think is we

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need to be better listeners.

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We have a tendency, especially those of

us that come from a technical background

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to get in front of a business audience.

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We have limited time, limited

opportunities, so we tend to

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go, here's everything I know.

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And they're overwhelmed and they

don't have the background, they don't

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have the context, and they don't

necessarily what to do with what.

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So I think being a better listener

and being able to understand the

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perspective and the role and what

is it that's important to you.

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So I make sure that I'm.

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So I think being a lister is another

I think another one and here to

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me is the major difference between

being a leader and a manager.

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Leaders lead from the front.

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They're in the front line

when there's a catastrophe.

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They're not home sitting in bed.

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They're in the data center, they're

in the office, they're working with

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the team through the whole thing.

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They're there, act.

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It wasn't even a breach, it was just,

it was an availability issue and all

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the executives were banging on the door.

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My job during that was

make sure my engineers.

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Shield and to be at the front

and not the back orders.

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I think you need people

see the big picture.

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I'm big fan of the parable about

the blind person, the blind

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people in the elephant, which.

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I always use to articulate the fact

that when we're really close to a

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problem, we don't see the bigger

picture, and we tend to make decisions

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based on what we see in front of us.

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And then we step back and it

turns out, oh wow, everyone's done

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that and we now have 10 parallel

solutions that are not necessarily.

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I think that one of the this

is there's discussion on

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frequently, showing that

you don't know something.

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Being open and honest, I think makes

you much more valued as a manager,

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as a leader, as an executive.

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There was Harvard Business Review probably

10 or 12 years ago, did a study and

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they found that being liked was much

more important, quality and an executive

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than being found to be competent.

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Right, and the only way that you can

do that is by not demeaning people, not

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insulting people listening to everybody.

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And here's the key thing, for those of

you out there, just because you listen

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doesn't mean you need to do what they

tell you, but they at least need to

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believe that they are listened to, that

they have been heard, and that you're.

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Mentoring thing.

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I'm a big believer that my job as

a leader, my replacement, right?

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Too many executive see that as a threat.

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I've seen people lose jobs because they.

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Showed up their manager, but

that's not what they did.

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What they did was they brought something

to light that needed to be discussed and

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talked about, and their boss didn't like

the fact that they got caught flatfooted.

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Now, if you get caught

flatfooted, that's on you.

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That's not on that.

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So I think those are a lot of

the things that I think are

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really important for leaders to.

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Christophe Foulon: Yeah we'll

dive into a couple others too.

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Let's dive into delegation.

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How would you define delegation and

your comfort level of delegation

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on a scale of one to five and why?

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I.

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Jeffery Wheatman: Yeah, so I

would've had a different answer to

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this 10 years ago than I do now.

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I think that leaders, especially

in larger organizations, have no

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choice but to delegate otherwise

you will quickly burn yourself out.

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I always joke that when I started

cybersecurity 30 years ago,

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it wasn't even, there's way.

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So I think you do need

able to trust there.

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I think that, letting people do

their jobs I think is very valuable.

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I do think you need to build

touch points in there, especially

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for high profile things.

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You don't wanna be in a position where

you get to the end of a six month

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project that you delegated and it turns

out they did not do what you wanted.

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As far as my comfort with delegation,

I have gotten significantly.

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I, my, the first thing outta my mouth was,

that's fine, but did you try it this way?

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And I was always trying to get people

to do things the way I want, right?

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And I think that is not a great way to go.

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So I would say I probably

used to be a two.

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I'm probably closer to a four now.

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Not sure if I'm ever gonna get to a five.

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I tend to have some.

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I, I do sometimes suffer

from I'm Jeffrey Wheatman.

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Do you know who I'm, and that's sometimes

cha challenging and problematic.

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But I think it's a skill that

can be learned and I think it's

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a skill that can be coached.

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And I think that for leaders that don't

feel they're good at it, go to your

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colleagues and learn how they do it.

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And I think we can learn

from, that's discipline.

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Christophe Foulon: And the

next one I would ask would be

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in regards to collaboration.

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So very similar to delegation, but n now

we have to be actively .Working with them,

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how would you define collaboration and

your comfort level at one to five and why?

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Jeffery Wheatman: So collaboration to

me is an example of the whole is greater

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than the sum of the parts, right?

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If you take five really smart people

and you bring them together, you'll

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get more than five times the value.

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You may not necessarily get five

times the work product, but you'll

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get more than five times the value.

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When I worked in consulting, I learned a

lot about that need to be collaborative

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because the tendency was for the team lead

to go their thing and bring it together.

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You'd end up spending twice as

much time, three times as much time

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bringing all the things together as

opposed to getting everyone in a room.

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I think collaboration has

been significantly hampered

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as a result of covid.

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I Think especially for younger people.

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I think it's much, much more

difficult to collaborate remotely

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than it's to do it in person.

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You and I can have a great interactive

conversation with the two of us.

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Add a third party in on, on.

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It gets more than twice as hard.

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Fourth party, it gets even harder still.

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And moderation of panels noticed you

people becomes harder to moderate

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panel other than a collaborative

environment for people to share.

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To share ideas.

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And I actually, earlier today I had a call

with one of my former colleagues at at

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the, that research firm I used to work at

and we were talking about the fact that

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one of their strengths is they're big, and

one of their weaknesses is they're big.

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Everybody's so narrow, they don't do a

great job on collaboration sometimes.

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I would say that I am

actually very collaborative.

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So I would say on give myself a

wouldn't really on bringing in ideas.

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And one of the things I

always suggest people do.

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When you have a bunch of people from

disparate backgrounds and you're trying

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to come to a, a conclusion, so a workshop

or a tabletop exercise, I always tell

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people, give everyone a different job.

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So for the exercise, the

CEO can act as the CIO.

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The CIO should be the CO.

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The CFO should be the CTO.

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And if you give everyone different jobs,

you don't always get what you want, but.

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A, I never thought about

it that way before.

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And to me that is one of the best

outcomes of co, of collaboration is

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getting people to think differently,

to be able to bring ideas together,

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to create synergies of ideas.

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And here's the thing.

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I think collaboration

is also not just people.

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I think collaboration is tools.

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I think collaboration is data.

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Chatt.

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I have started to use ChatGPT

as part of my team, right?

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Because ChatGPT has

different perspectives.

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I wouldn't go so far to say have thought,

but they have different perspectives.

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And I think collaboration

is about bringing that in.

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And if you're collaborating by

having six of the same people in

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the room, that is not collaboration.

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So you gotta bring in di disparate

backgrounds and perspective.

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Christophe Foulon: And on the

next scale, communication, how do

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you define communication and your

comfort level with communication

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on a scale of one to five and why?

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Jeffery Wheatman: Yeah.

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So on a scale of one to five, I

give myself a 10 on communication

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to pat myself on the back.

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It's a key for what I do, right?

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My job now is, as an evangelist,

is about communicating.

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My job as a Gartner analyst was about

communicating, and about 80% of what I

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did when I worked at Gartner was helping

people be more effective communicators.

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But coming back to the actual

question, communication is about

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bidirectional interaction, right?

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Communication is not

me telling you a story.

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Communication is me telling you

a story, and then as I'm telling

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the story, I'm watching your

face, I'm watching your hands.

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Are you leaning back?

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Are you leaning forward?

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Are you looking at.

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And make it much more interactive.

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I always tell people, and I

tell, I'll tell your audiences.

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Now, when you're talking to someone, don't

ever say, does that make sense to you?

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Because that's super insulting and

very pedantic, but what can you say?

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Is this helpful?

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Will this help you make better

and more informed decisions?

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If your management comes and ask you

this question, do you feel comfortable

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answering it based on, we talked

about, those are all different ways.

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Saying does.

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Not offensive, and you don't wanna

be viewed as pedantic or mansplain

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to, to use a different term.

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But I we had a management meeting a couple

weeks ago and I delivered a 30 minute

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session and then one of my head sales

guys came up to me and he goes, thank you.

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He's thank you for dumbing that down.

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And I said, I didn't dumb down.

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I.

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You.

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Why?

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Why would I make you learn

what I know, when I can take

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what I know and contextualize

it so that it matters to you?

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You're in sales, you don't care about

all of the technical detail, so I

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think communication is very much about

meeting people where they are, and

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sometimes you meet them there and then

you pull them closer to where you're.

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But I feel like it it's, yeah,

I think it's an underused skill.

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I'm a huge proponent of storytelling.

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I do presentations on storytelling

all over the world, and I'll let

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everyone in a little bit of a secret.

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I was at an event and they were

about 400 people in the audience, and

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they were more on the junior side.

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And I'm talking about

storytelling, and I'm looking and.

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I'm an introvert.

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You wouldn't know it from listening

to me, but my, if I had my druthers,

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I would be sitting at home on

the couch with my beautiful wife

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watching TV and never going out.

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But that's not a functional lifestyle,

plus no one would pay me to do that.

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So I have adopted a character and that

character is the cyber risk evangelist,

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and that character is funny, entertaining.

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Create your own character.

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And I think when we communicate,

I think creating your character

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is super, super important.

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And I actually was talking with someone

at an event a few weeks ago and they

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said, so tell me who your character is.

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And they didn't really know.

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And we worked through it and we said,

all your character has these qualities.

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Your character has these weaknesses.

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Let's be that character.

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And when we finished the conversation,

she said that was like, that may

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be the most helpful 15 minutes

anyone's ever given me in my career.

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Because it never occurred

to me that I could do that.

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Everyone thinks they need to

be and you need to be genuine.

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You don't wanna be fake.

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This is a character that I've

been playing for a long time.

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So I think that, those

are super important.

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I don't ability to be an

effective communicator.

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I everything's as.

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Christophe Foulon: Now

pivoting off of communication.

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How would you describe the skill of

influence and why is it so critical for

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cybersecurity practitioners and leaders

to use this skill within their roles?

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I.

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Jeffery Wheatman: That's a great

question and I don't think anyone's

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ever asked me that specific question,

so I think that, the word influence, I

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think has a bit of a connotation to it.

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So we need to be careful, right?

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You don't want people to construe

it as you're being manipulative.

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But I think exerting influence is

about, and coming back to one of

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the first things that said is going

to your audience and understanding.

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So what's important to.

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And then taking that and

wrapping that around what it is.

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I would like you.

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So As a simple example I could

go to my executives and I could

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say, and they're probably money.

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If I go to them and say, so I spoke

with all of the EVPs, the SVPs, and

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they've told us this system here

is probably the most important.

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When we have this system goes

down, gets breached, we're outta

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business, or we're gonna be fine.

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We have to protect that system.

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We have some things we do,

and I'll be honest with you,

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we have some gaps in those.

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We'd like to close those gaps.

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We need to make an investment.

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We need X 5 million.

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If we don't do that over the next couple

years, based on everything we know.

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Suffer million.

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I think is really powerful.

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And then I will, I'll make a

suggestion to everyone out there.

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There is a psychology professor.

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His name is Robert Chi Aldini.

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He works at, I don't remember, it's either

University of Arizona or Arizona State.

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And he wrote a seminal book

probably 15 years ago called

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Influence Science and Practice.

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And he talks about six ways to

get people to do what you want.

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And the book is great if you

can find the original versions.

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He's got a lot of stories in

there, but things like reciprocity,

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if I do something for you, you

feel obligated to do something.

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For me, it's human nature, right?

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If you create the perception of scarcity.

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People will do.

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People wanna do, people want to

interface with people they like.

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And that's where finding

common touch points are.

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So you people like people who look

like them, but they also like people

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who like the same sports as they do.

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They like the same teams, the same

movies, the same books, right?

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The same kind of music.

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So building those bridges and I won't

go through all six of them, but I

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use them frequently, probably every

single day to get people to at least

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understand why I'm pitching them on

whatever it is I'm pitching them on.

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And I think that, the final thing about

influence, that's very important there is.

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Where you are going to be done, you're

gonna be finished making your point.

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You're share what you know what

is just gonna say no, and you

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need to learn to step back.

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You can't drag people all the way,

but what you do need to do is document

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the conversations and document.

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And I think we're gonna see a lot more

of this with the SEC ruling and some

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of the other regulatory stuff that's

coming out where, CISOs cannot be held

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accountable for decisions that are being

made by their business stakeholders.

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So if

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communicating what the risks are.

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That's on you.

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Not on me anymore.

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And I know we don't like to give up.

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No.

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You don't understand.

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Lemme just tell you one more thing

and it'll definitely change your mind.

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And that's just, that's not gonna work.

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Use what you got and then be

prepared to step back and let

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people do what they're gonna do.

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People are, have their own

agency, they're gonna do.

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Christophe Foulon: Absolutely.

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And going from there, let's

talk about another important

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skill the skill of networking.

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How would you describe the skill of

networking and why is it critical

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to cybersecurity and leadership?

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And just to set the stage, this

is networking between computers.

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This is networking between people.

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Jeffery Wheatman: Yes.

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Yes.

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That's good 'cause I don't

know that much about networking

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between computers anymore.

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So I think that's a great it's

a great thing to talk about.

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I think there are lots of different

kinds of networks out there.

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You have your network at your

office, at your company, right?

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You know who decision makers are, and

frequently decision makers are not who

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you think they're, when you first walk in.

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You need to be able to bring

disparate parties together.

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:

There, there was a book a bunch of

years ago, it was a little bit more

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technical, but it was about networking

theory with people and they identified

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things like hubs and influencers and all

these different roles, and they actually

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used it to analyze the hijackers for.

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So I think you have to

have internal network.

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I think you also have be network

people outside organization.

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People.

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Who are in and out of your vertical?

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:

One of my roles at Gartner was

I was a leadership partner.

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And the thing I learned, the most

valuable thing I learned from that role

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was that there are things that higher

edge doing that can absolutely inform

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:

what financial services are doing,

but they're not talking to each other.

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Giving more than you get, giving

more than you ask for, right?

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So I'm very active on LinkedIn.

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I actually just hit 5,000

followers last night.

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I was very excited about that.

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:

And I, I know for you, you

have a couple more than that.

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:

I'm never gonna catch up.

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But what I try to do is for every

one thing I put out there where I.

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:

What we do at Black Kit, because

ultimately that's my job, is

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:

I talk about other things.

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I talk about what's going on in the world.

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:

I share parables.

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:

I take pictures and use

them to build stories.

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And then when people like what I

post, I go and connect to them and

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I say, Hey, thanks for engaging.

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:

If there's anything you need,

please do not hesitate to ask.

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And I think that's

probably how you and I met.

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:

On LinkedIn was, I like something of

yours or you like something of mine.

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And I reach out to all those

people and I say, look, I, anything

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:

you need to do, you reach out.

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:

I'll be happy to help you.

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I make connections with people all

the time on LinkedIn, outside of

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:

LinkedIn, and what I have found is

other people are willing to do the.

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:

I think sometimes security people

have a tendency to interact

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:

with people and detriment.

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:

Now, keep in mind.

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:

You can only have so many close friends.

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:

So networking isn't always about that.

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And my wife has actually said to me

more than once, my wife owns our own

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:

company and she does branding for people.

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:

She says, frequently you get more

from the people who are a little

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:

bit farther away from you than the

people that are super close to you.

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:

Hey, can you intro to me to this person?

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:

Christophe Foulon: I I'd echo what your

wi, I echo what your wife said because,

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:

for example, in, in my recent search.

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:

All the people that were close to me

already knew what I was looking for, but

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:

when I posted it publicly, it's all the

people that I didn't interact with on a

472

:

daily basis that were doing the shares,

that were commenting, that were doing

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:

And you'll find that the people that you

interact with daily, the reciprocity that

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:

you have with them usually has been used.

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:

Continuously.

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:

So there, there isn't that that

feeling to give you more, whereas

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:

the people that you've potentially

helped without knowing it, they're

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:

not willing to go, oh, the advice you

gave me 10 years ago was so helpful.

479

:

Of course I introduced

you to that person, or

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:

whatever the situation might be.

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:

But

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:

totally agree with you there.

483

:

Jeffery Wheatman: Yeah.

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:

then one thing I'll just add on there

too, which I think is important, I

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:

for quite a while, I always hesitated

about reaching out to people.

486

:

'cause I don't wanna bother you.

487

:

I don't wanna bother them.

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:

And whenever I articulate that to people,

they go, what are you talking about?

489

:

It's no bother.

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:

I love talking to you.

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:

I love helping people.

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:

So you are not bothering people as a

general rule when you reach out to them.

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:

People are on LinkedIn because they

wanna be linked to other people.

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:

And I think it's important you're not

bothering and you're not bothering me.

495

:

If you listen to this and you

connect to me, I'll respond.

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:

And if you need anything, I'll

do my best to try to help you.

497

:

Christophe Foulon: And as, as we

wrap up the end of our podcast I know

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:

you've shared a lot of advice, but

what final advice would you give to

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:

cybersecurity leaders that are looking to.

500

:

Pivot up from a more tactical

career to a more strategic

501

:

career to move on up that chain.

502

:

Jeffery Wheatman: Yeah, it's a

tough, that's a great question.

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:

It's tough.

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:

I think finding yourself a mentor, in

your organization, maybe out of your

505

:

organization who can guide you because

it's a big step to go from being

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:

a practitioner to being a leader.

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:

So I think finding a mentor or what we.

508

:

But I think the other thing too is

you need to expand your learnings.

509

:

There's free classes online.

510

:

Learn how to read AP and l.

511

:

Learn how to read a general ledger.

512

:

Learn how to read a balance sheet.

513

:

Take classes in, in public speaking learn.

514

:

Start looking at 10 Ks looking, 10 Qs

looking at annual reports for companies,

515

:

figuring out what it is that is important.

516

:

And here's one last

thing, stop with acronyms.

517

:

Acronyms are great when you're talking

to people in your tribe, but when you

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:

start talking to people outside of your

tribe, acronyms basically insulate you.

519

:

We don.

520

:

Don't,

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:

but it's an important thing.

522

:

Meet people where.

523

:

Christophe Foulon: Absolutely.

524

:

Jeff, thank you so much for

sharing your advice with us.

525

:

Truly appreciate it.

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:

For everyone.

527

:

As a reminder, thank you for joining

Breaking into Cybersecurity Leadership

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:

where we're looking to help develop the

next generation of leaders so there's a

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:

leader or a future leader in your network.

530

:

Feel free to share this with them

so that they can learn from the

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:

skills and competencies of others,

and we can have that diverse

532

:

perspective within our industry.

533

:

Thank you all.

About the Podcast

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Breaking Into Cybersecurity
Developing cyber pros of the future!

About your host

Profile picture for Christophe Foulon

Christophe Foulon

It’s a conversation about what you did before, why did you pivot into cyber, what the process you went through Breaking Into Cybersecurity, how you keep up, and advice/tips/tricks along the way. You can also bring up topics like attraction/retention/developing the next generation of the workforce.

Cybersecurity Leaders, we would love to help develop the next generation of cybersecurity leadership. We will do us on the critical skills and competencies of leadership, and you can also bring up topics like attraction, retention, and developing the next generation of the workforce.

Let me know if you are interested and available email - breakingintocyber@gmail.com

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