Cyber Talks - Break Things Safely: A High-Value Cyber Exercise Program with Daniel Hammond

Hey everyone,

I'm Jason Edwards and welcome to another

CyberTalk developed by

baremetalscyber.com.

Today we're joined by Daniel Hammond,

a respected voice in the field of

cybersecurity and resilience planning.

Daniel brings a wealth of experience

helping organizations prepare for the

unexpected through realistic and impactful

cyber exercises.

His presentation,

Cyber Exercises Beyond the Basics,

challenges the notion that exercises are

just check the box drills.

Instead,

he's going to show us how they can

become strategic tools to strengthen

coordination, reveal blind spots,

and build confidence across teams.

Daniel's work focuses on taking these

simulations far beyond the let's practice

this thing and transforming them into a

core part of an organization's learning

culture.

He's passionate about tailoring every

engagement to maximize its value for the

audience,

making sure each exercise delivers

insight, not just activity.

We're featuring Daniel as part of our

Cyber Talk series,

where we invite experts and professionals

from across the industry to share insights

that make a difference.

If you'd like to take part or learn

more about upcoming sessions,

visit baremetalcyber.com for details.

And welcome, Daniel.

Hey, Jason.

Thanks for having me.

Let's break some stuff, yeah?

Yeah.

Good to see you this afternoon, too.

Likewise.

So if you like,

go ahead and take it away.

Daniel, tell us about yourself,

what you do,

and what you're going to talk to us

about today.

Yeah, fantastic.

And really appreciate, A,

what you're doing with your CyberTalk

series.

And I always love to learn more about

how I can bring value as a cyber

expert, right?

And so one of the skill sets that

I have, in fact,

let me go back a little bit.

I have a military background,

so I was an Army veteran,

and was in the Eighty Second Airborne

Division, signals intelligence.

Then I went into the Army Reserves,

switched over to human intelligence,

became an instructor, ended up deploying,

interrogating some of the most wanted in

our theater.

Then I ended up helping design an advanced

interrogation and analysis course.

I used to break people and now I

break computer systems or at least

simulate that.

When everything's running smoothly,

you don't learn much.

I think having something disrupt your BAU,

And it's better to have it come from

an internal request for a disruption

rather than having the bad guys disrupt

you.

And one of the examples I'd like to

use is, you know,

if you're in a skyscraper,

you don't want to figure out what the

fire is.

exit procedures are while the building's

on fire, right?

You want to have practiced that until it

has become second nature.

And I think that's what we do in

the cyber exercise space,

or at least one of the aspects.

And I'd like to go into some other

deeper use cases with you and the viewers

today.

But that's it.

And really, I got in.

I transitioned from Humint and SIGINT into

cyber intelligence.

So I started doing cyber threat

intelligence for a major bank.

And I've helped build cyber exercise

program at three Fortune five hundred

financial organizations,

including leading, bringing it into one.

So that's.

sort of,

and I've done exercises of like all shapes

and sizes.

I'm sure I'll weave some stories in as

we go, or feel free to interrogate me,

my friend.

Well,

and exercising is a really undervalued

thing, right?

You know what I mean?

It's always better to find the flaws in

your plan before you need the plan, right?

We talk about it with instant response,

but there's many, many, you know,

things that you can do out there to

exercise your team and you need to, right?

We're like thoroughbreds.

If you don't race, you know,

if you don't practice for the race,

you don't race, you know,

you're never going to have a good team.

So.

Absolutely.

One hundred percent,

especially if you're in a heavily

regulated industry.

Even if nothing's happened to you,

some of your peers,

things have happened to and the regulators

have seen those things and then they come

in and they ask you about the gaps

that your peer used to have before they

got their problem.

And if you don't have,

if you haven't thought it through at a

deep enough level,

you're also not gonna have a plan.

And so, you know,

we should learn from each other.

We should, I mean,

the bad guys are out there evolving every

day.

So even if we were a hundred percent

protected today,

tomorrow's a new day with new

capabilities, so.

Well,

it's interesting you mentioned regulators

too, right?

They have a very horizontal view of how

the industry works, right?

They go to one organization,

they see how it works.

They go to another organization,

they see how it works.

And it's very,

very easy after a while for them to

see that, hey,

you're not like the others because you're

not doing X, Y, or Z, right?

And that's really what,

that's the little rough spot on your edge,

right?

That they start peeling off and digging

into.

Whereas if you look like everybody else

because you're doing the best practices,

right?

It's why we call them industry best

practices.

then you have a much easier time with

regulators.

You completely agree.

And I definitely see that as like you

grow to the next level of maturity in

size and structure.

You know, the response maturity,

the resiliency things that are done at the

top tier are new to you.

And you got to close that gap as

fast as you can because otherwise all

you're going to be doing is chasing your

tails, you know.

trying to address things that the

regulators uh have caught and it's better

to self-identify and solve them before

they get there absolutely so you brought

some slides today i'm going to go ahead

and bring them up and uh let's see

OK, I'm ready when you are, Daniel.

Yeah, fantastic.

And just so you guys know,

I have a couple of companies.

One is called Business Interrogation,

which is really all of my consulting work

is about asking questions to help people

improve their resiliency,

to think through market disruptions and

that type of thing.

And really,

cyber exercises are like one of the core

pillars of what I do and how I

serve people.

I think next slide is, yeah,

we can skip that one.

Yeah,

this is just some of the things I've

done.

I guess I've covered probably most of that

stuff.

I did just a couple of other interesting

tidbits.

I've also worked in physical security.

I ran a top tier physical security company

in one of the most violent cities in

the world with over four hundred

employees.

And I helped build a nursing school in

central Honduras.

And I'm a contributing author on seven

books,

including the lead author on customer

driven leadership.

outstanding and thank you for your service

oh thank you man you too yeah so

um let's kind of look at the basics

of cyber exercises i think one of the

things that i find is the biggest

obvious thing is if I see people doing

exercises and they don't have a goal,

sometimes called a purpose,

then I kind of start to doubt their

maturity because really every exercise

should be trying to accomplish something

for someone.

Typically we call it the sponsor or the

stakeholder.

But if if if you don't know what

the requirements are,

if you're just exercising to exercise,

it would be like going to the gym

and randomly doing three things every day

when you walk in there.

you don't have a plan,

you're not going to get an outcome that

you want.

So really drilling into that goal is the

first thing that really directs what are

we trying to do here?

And a lot of times the sponsor and

the stakeholder are not exercise

professionals and you don't have to be,

right?

If you hire a professional,

They're going to be able to take your

what I really need and turn it into

an exercise goal for you.

And when they express that goal back to

you, it should make sense.

And you're like, yeah,

if you can do that,

that's what I need.

Right.

You know, if you're doing, let's say,

a regular an exercise to satisfy a

regulatory requirement.

and you didn't read the requirement and

know how that box needs to be checked,

you're wasting your time, right?

You're not going to satisfy what the

regulator wants.

And so you really need to, you know,

I've had people come up to me and,

you know,

you want them to hire you to do

an exercise.

But my first question is,

is an exercise really what you need?

Will it check your box?

Otherwise,

maybe we're fishing in the wrong pool.

Typically,

most exercises are scenario driven.

I think there are a few use cases

where I would say it's not always the

case that they would be,

but usually that's the case.

We'll go into some use cases later on

where the scenario might be less

important.

Typically, you have a facilitator.

Sometimes in an operations-based exercise,

where you're actually doing the doing

rather than talking about the doing.

I use the Homeland Security Exercise and

Evaluation Program as the model.

It's not specific to cyber exercising,

but it is the government standard for how

an exercise program should be run.

There's two types of exercise,

discussion-based where we're just talking

about what we would do,

and then there's operations-based which

At some level,

somebody is doing something that they

would actually do in response.

And then you want to make sure you

have the right participants there.

Don't bring people into an exercise that

have nothing to do.

You have no engagement for them.

Don't leave out people.

Sometimes you have people that have to be

there around the table for the exercise to

be successful.

If they can't be there,

you probably need to reschedule it so that

they can be.

Or maybe look for them to send a

delegate from their area of expertise.

uh trusted agents are the people that we

use uh you know i'm not an expert

in all things so i work with uh

you know i talk to an executive and

i'll say give me the person that knows

how all of this works and should work

and then i kind of uh

pinky swear them to secrecy if it's uh

if it's required to keep the scenario

secret which again it's not always

required but uh and then they help me

understand how things should flow so that

i can build the scenario and know kind

of which way the dominoes will fall

And then, of course,

you might have people who are just there

to observe the exercise.

That could be potentially an audit-like

function.

But inviting audit into an exercise

changes the exercise because a lot of

times one of their strongest selling

points is this is a safe environment.

When audit's there,

it's a less safe environment.

And then finally,

you want to generate a report that says

this is what we learned together through

this exercise.

Perfect.

Yeah,

I'll just run through a few of these

and go ahead.

So the purpose of a seminar is sort

of educate participants about a cyber

concept.

And again,

this is in the world of cyber threat

exercises.

So if you want to jump to the

next one.

Yeah.

So let's say there's a new threat out

there and you

you can send out an email saying, hey,

everybody watch out for this new threat.

But if it's serious enough and you need

to orient your people,

especially those that are not very cyber

tech savvy,

a seminar is a good way to kind

of push that information out of this is

the new threat.

Like maybe one of the things is threat

actors are now using AI to craft better

phishing emails, right?

So you want to show them kind of,

what an AI-generated phishing email looks

like versus what the emails looked like

two years ago,

which are going to be very different,

a lot of grammatical errors and things of

that nature that AI is not going to

make.

So it just helps orient the people to,

hey, this is a new threat.

This is something you can do.

A lot of times you can do this

as kind of a lunch and learn and

just educate people while they eat their

lunch.

And kind of the human factor is always

critical when it comes to potential gaps

in cybersecurity.

So the smarter your people are.

And, you know,

whether that's a seminar maybe every two

months and and maybe an exercise,

you know,

a couple of times a year can really

help make your people more aware of how

the bad guys come after them.

Absolutely.

I think executive education is super

important.

Sometimes the technical people within the

company know that we have this big,

horrible gap.

But if nobody else knows that,

then being able to communicate that to

executives is super important.

And and, you know,

there you can talk tech to them all

day long,

but their eyes will glaze over and you

have to communicate what is the real

threat to the organization in the language

of the things I care about.

Right.

So is it going to hurt our reputation

if this happens?

Has it happened to three other people in

our industry and we're not

we're making the same mistakes they did.

You've got to translate it into this is

how many dollars and cents not taking care

of this could cost us.

Let's say you push out a new response

playbook or something like that.

A seminar is a good way to say,

hey,

this is how we used to do it.

This is why we changed it.

This is the new process and procedure.

You just get everybody on the same page

very quickly.

Any thoughts on that, Jason?

I think also a great thing about a

seminar, right,

is that you don't need a lot of

preparation for it.

Right.

It's something that you can execute

immediately.

Like you could do it today.

Right.

People can ask you to do it today.

Yeah.

Yeah.

I mean, really,

what you need to know is you need

to you need to understand the threat and

just take a little bit of time to

think how you can communicate that again

in the language that they need to hear

it in.

And then really it's not very interactive

in a seminar.

It's mostly sort of a presentation, right?

But you can certainly have time for

questions either as you go.

I like to kind of do a block

and ask if there are any questions.

um and and then for sure by the

end say does anybody have any questions or

comments or things that are relevant to

this topic that could help us you know

improve our cyber security and then you

you'll you will get some good feedback

typically absolutely okay you can go into

the next one

Workshops.

I think workshops are the most

underutilized of the kind of cyber

exercise offerings.

The thing about a workshop is, you know,

you're trying to create or work through a

cyber product or concept.

So it's more,

even though it's still discussion based,

you're trying to generate an output.

um that that moves cyber security forward

in the organization you want to go to

the next one we'll look at some specific

examples so let's say um all of a

sudden you want to uh bring ai into

your company right um before you just you

know load up copilot and let it run

which is the strategy

I don't think it's a strategy.

It's a way.

It's a way.

It's a way.

uh, loosen your network, right?

You've got to provision it.

You've got to make sure it only has

access to the things it should have access

to.

You need to make sure that, um,

I can't access the AI to get information

that I shouldn't have with my level of

access, right?

There's,

there's a lot of things that you've got

to think through.

Um,

you don't want the AI cross sharing your

information inside and outside of the

network, right?

So you've got to know how are we

going to, what kind of, uh,

walls are we going to build around the

AI and, you know,

how does that restriction benefit or

hinder us?

Right.

So there's a lot to think through in

that.

And so one thing that you can do

is bring all of the key stakeholders

together and go, OK,

who who's got concerns about us bringing

in Copilot?

What what's going to work?

What are you going to be worried about?

And have that discussion around the table

um of of how is this going to

change how we do our our cyber or

protecting the organization from a cyber

security perspective um i've done some of

those with cloud you know organization

thinking about moving stuff into the cloud

in a new way and i'm like we

we walk through here are all the tools

that protect our on-premises um you know

information

how is this gonna work in the cloud?

And in that particular case,

I brought in the lead Azure architect and

he helped us answer the questions.

So literally we had seven executives

around the table and I facilitated sort of

an interrogation of the Azure architect.

And nobody knew better than he did how

their tools work.

So it quickly closed that knowledge gap of

how do we continue to protect

the organization,

which of our tools are still going to

work?

Which of our tools are we going to

have to rely on this partner for?

And so those are the types of things

you can get out of a good workshop.

Pivoting to new technology is good.

How do we create a new response plan

for X scenario is a great time to

do a workshop.

Orienting people to the new plan before we

tabletop, which is the next exercise type.

How can we go in and do a

workshop and just talk through?

This is how the new plan works, right?

You know, before you used to do this,

now you do this just so that you

set those expectations and prepare for

success at the at the next more,

let's say, advanced level.

And one thread through all this, right,

is that you're validating your risk

assessments.

If your risk assessments are accurate,

then the exercises at the end should be

accurate as well, right?

I mean,

they should at least align to what you

considered the risks were.

If you find new risks, right,

that's a good thing because you can go

back and update the risk assessment

process, right?

It's continuous learning cycle between the

two.

A hundred percent.

And, you know,

I like a workshop to kind of kickstart

a process.

For example,

I was working on an industry level

response.

So we had a bunch of working groups

all trying to solve pieces of this.

It's sort of like building the

International Space Station in the cyber

universe for resiliency for the industry.

And the first exercise, they're like,

let's do a tabletop exercise.

And I'm like,

I don't even know what the other

people are working on,

why don't we do a workshop where everybody

brings in their pieces of the puzzle and

we start to assemble it on the virtual

tabletop in front of us and see,

a lot of times you'll find gaps.

You had like, oh,

I thought you were covering that, Jason.

And you thought I was covering it.

And now we've got this giant hole that

nobody's solved for.

Well,

let's fix that before we do the tabletop

because once we do a tabletop and put

it in front of senior people,

we don't want to trip over our hole

in the system, right?

We want to look like we're polished and

we have a plan that's going to work.

Some inadvertent silos, right?

Correct.

Yeah.

And also a lot of, you know,

you can do this with critical partners.

I think exercising with critical partners

is another great way to kind of build

relationships and better understand how do

you have my back in this space, right?

And how are the actions I'm going to

take be supportive and synergistic with

what you're going to do?

Because if a problem happens between us

and a third party and they run this

direction and we run this direction,

it's going to be bad for both of

us.

It's better to have some sort of cohesive,

let's talk about this so that we can

mitigate how badly this ends up for both

of us.

Absolutely.

Cool.

Go to the next one.

Next one's a tabletop.

Those are a lot of times what people

are familiar with.

And it's sort of this is a highly

scenario driven where you've sort of

predetermined the talking points of what

should happen from the beginning.

of where you kick this off to the

end of the exercise.

And the cool thing about an exercise is

you get to decide where does it start

and where does it end, right?

You can certainly have kind of have it

kick off before anything

you know, crazy is happening,

maybe it starts off with some probing in

the network or something like that, right?

And then it goes all the way.

And I mean,

you can also take it all the way

to through bare metal rebuild, right?

I mean, but typically,

depending on the teams you're exercising,

you're going to exercise the pieces that

are important to the teams and the

participants.

And again,

going back to that goal statement.

And so it's these are the places where

you validate or practice and familiarize

with your cyber response plans.

And again, it's not just limited to cyber.

Again,

you want to it's effectively sort of what

we do again with like, you know,

practicing live shooter events and things

like that.

How do we how do we how do

we react to a bad situation in the

most positive way?

You want to go to the next one?

Yeah.

So validates your cyber response plan

works.

It validates that users understand how to

implement the cyber response plans.

Builds proficiency, right?

Again,

going back to that building on fire,

you don't want to figure out how to

get out of the building when the

building's on fire.

You want to already know the three

contingencies for you to get out of the,

you know,

demonstrating that you're practicing and

improving your cyber response plans,

right?

So one of the things that you can

do is show growth for your executive

leadership, for your auditors,

for your regulatory people.

There's nothing better than having it.

Uh, when they say, oh, hey, have you,

what are you guys doing about X?

And you're like, oh,

we exercised X two months ago.

Here's our lessons learned out of that.

And this is what we're doing to close

those gaps.

I mean, that's, uh,

whereas what's the other thing, you know?

Oh yeah, we have a plan for it.

Does it work?

Have you thought through it?

Have you checked the plan?

Do you know that it works, right?

And you won't have the same answers or

confidence.

And confidence is important when you're

dealing with these regulators, right?

Well,

and it brings me to an experience once,

too.

We had an auditor.

And their comment was, well,

but you didn't cover every case.

You didn't cover every possibility, right?

It wasn't detailed enough.

And I gave them the explanation.

I was like, look,

I've done many military exercises,

like high-end military exercises,

millions and millions of dollars worth of

tanks.

And not a single one of those that

I ever really face, right, in real life.

But it's the fact that I went through

them and I was thinking about it and

that I was reacting and I was learning

through that stress is what made it better

in the end when it did happen or

different things happened, right?

And so even if you can't cover every

single use case in an exercise,

the action of doing the exercise is what

is another huge benefit out of it.

Yes,

and this would be my response to the

auditor who asked me that question or the

regulator.

Okay,

could you just give me the comprehensive

list of every possible way I could be

compromised,

and I'll start working on validating,

right?

And sign it, too,

so that if I'm compromised in a way

not on your list,

you can take the responsibility for that.

Every day is a new day with that.

Right.

Right.

Yeah.

Yeah.

And one hundred percent.

You you can't practice for everything.

Right.

And ultimately,

even the most mature exercise programs

that I know are not exercising.

Ninety five percent of an organization for

ninety five percent of the risks.

under the craziest of circumstances it's

just not feasible what you want to do

is you want to try you want to

practice a little bit of this and a

little bit of this and a little bit

of this and then what you're doing by

by trying something new each time and then

maybe revisiting when something went

really bad

Right.

If you had an area that showed a

lot of weakness,

plug that hole and then and then

reexercise it and see how much more

smoothly it goes.

But then also continue to evolve your

program.

Right.

If it you know,

there are some exercises where you need to

be successful.

Right.

The most important thing is we've checked

the box the regulator has given us.

Right.

And you don't want to play around with

that.

You don't want to you don't want to

accidentally do the exercise and forget to

check the box.

Right.

Going back to that goal statement.

But by the same token,

if it's not one of those check the

box exercises, think through.

I'm always trying to think, OK,

I have to do an exercise in this

space.

What could I throw in here that would

be novel, that would be new,

that would help test resiliency in another

aspect or another way that we haven't been

doing, right?

You want to...

And then once you succeed and you've done

all the things at the cyber response

level, start bringing in other teams,

the regulatory response people,

the communications teams.

If they're not already a part of that

core response,

depending on how technical and tactical

you are,

start going to the strategic and the

operational as well.

Absolutely.

Absolutely.

Yeah, I think the next one is drills.

Really,

this gets us into the operational exercise

space.

And if you want to kind of, yeah,

jump over here.

I look at drills as you're actually

practicing some part of the response.

So maybe it's making sure you can get

the right executives on the bridge line

that you need to troubleshoot a project.

say regulatory issue in, you know,

fifteen minutes or whatever your,

you know,

standard response time should be.

That could be a drill, right?

Another drill could be you work with a

red team to compromise something on the

network and see how long does it take

the cyber response people to see it and

respond to it.

Obviously,

you want to be very careful when you

start putting live things on the network,

and there's some creative ways to do that.

I was in charge of evolving a cyber

range at one point in my cyber exercise

program.

background.

And so you know,

those are ways where you can, you know,

practice those things a little more

freely,

but also a drill could be a no

notice exercise where we're not telling

them they're being exercised.

We're watching how they respond to a

controlled compromise, right?

Like, we're in charge, we're running,

we're running the, the bad guy.

And so

we're not just unleashing malware across

our networks, which would be very bad.

Probably the last thing you do at your

place of employment.

Going back to what you said though,

it's always good to honestly not let the

SOC know that there's an exercise going on

until it's done.

You want them to treat it just like

any other thing.

If you tell them something's going on,

you have two problems that.

One is that it's not as serious for

them.

There's not as much adrenaline in the room

because they know something.

the other problem is is what if you

do have an attack and they think it's

part of the red team exercise right so

it's better not to tell them at all

in my opinion just let it happen right

you know what i mean and then see

what happens at the end it's not like

there's a payload waiting you know from

the red team attack so right

Yeah.

And again,

you're probably going to start small in

this kind of thing.

But what it does is it just lets

them be aware and let them know, hey,

we exercise periodically.

You'll treat every single thing that you

see as if it's real until you're told

otherwise.

Even if you figure out beyond a shadow

of a doubt that it's an exercise,

you're going to do all the things you're

supposed to do as if it were real,

right?

Just set those expectations across the

team.

It, A,

keeps them kind of at a heightened level

of alert without overwhelming them,

hopefully.

It keeps them curious, right?

I see something on the network.

Well, it might be an exercise.

Well, it might not be.

Let me go through and keeping an open

mind for is this a simulation or is

this a real bad guy on our network?

And, you know,

commend people also as well, right?

Sock burnout is a real thing.

I mean, every time, you know,

sock analysts see something,

it could be the thing that ruins the

company, right?

That's a lot of stress on a person,

you know, working eight, ten hour shifts,

right?

So when they do catch this kind of

stuff, you know,

make a big deal out of it, right?

I mean, that's an amazing thing.

Great.

Look what you did.

This is awesome.

You know, kudos, you know, spot bonus,

something, right?

One hundred percent.

Yeah, I love that.

Love that.

Yeah.

And, you know, again,

it could be practicing a media response,

right?

Having the communications team actually

write your response.

What would you tell the media?

What's your press statement for this?

So actually that's, again,

how you do an operational type exercises.

There's some doing.

Other ways I like to do this,

and if you go ahead to the,

I think next slide is sort of the

other use cases of things that I think

are fairly interesting.

Yeah, so these are some other use cases.

One is, you know,

the functional exercises, again,

are like tabletops,

more like tabletops and drills.

So you're actually practicing a response,

but there's also some doing in it.

And one of the things that I like

to do is you can see the next

thing on the list is a full scale

exercise, right?

That's like,

let's pretend across the entire

organization this bad thing is happening.

right, let's bring in all the leaders,

bring in everybody.

Well, before you're ready for that,

you need to carve that into pieces and

practice it in pieces to make sure that

you understand how everything is supposed

to fit together.

Because if you don't do that first,

you're going to miss something and your

full scale exercise is going, it's,

you know,

it's like designing that ten thousand

domino thing where you've got everything.

And then all of a sudden you hit

and like right in the middle,

the domino misses.

And then what are you going to do?

Half of it's fallen over.

You can't get to the middle to knock

over the next domino.

Yeah.

it's a big mess so really you kind

of that stair step of increasing maturity

and complexity is really key to doing that

capture the flag exercises are good these

are those cyber range exercises where you

actually practice defending a virtual

network against um bad guys that could be

maybe peers in your industry if you wanted

to host a capture the flag with some

of your your peers in the industry and

kind of have some bragging rights and

you know,

a ridiculously huge trophy that the CISO

gets to put in their office or,

you know, whatever it is, right?

They like this.

They have an extra flag.

Yeah, right.

And then one of the things that I

really like,

and it's the last thing I really have

on this is purple team exercises.

So if you've got kind of that red

team expertise,

especially internally to your

organization,

And let's say you've got five layers of

defense for a specific type of attack,

and they get through the second,

and they get stopped by the third.

And you're like, oh, we won.

We kept them out.

Our layers of defense worked.

But if you don't test layers four and

five,

Maybe they get through levels four and

five as easily as they got through one

and two, which means you have one defense.

And as soon as they,

you know how threat actors are,

if they have the resources and the will

to keep banging their heads against that

firewall of yours, eventually...

they're likely to find something.

Again,

that's why you don't want to be the

low hanging fruit in the industry.

But again,

you also want to make sure that if

you think you have five layers of defense,

you're not actually just relying on a

single layer.

What we can do in that case within

a purple team exercises,

the red team compromises something on the

network,

the blue team looks for it until they

find it.

It's like, okay, I've taken over a system.

blue team looks maybe they get some hints

until they see oh yeah okay i see

what you've done and then they go okay

i moved laterally to another system okay

yep we see that okay now i'm trying

to get through this cyber security defense

okay and let's say once they get stuck

on that layer three that oh we can't

get through this

let the blue team let them through so

you can test that layer four and layer

five of your defenses, right?

Because if it's just a single layer that's

keeping the bad guys out,

that's probably insufficient.

And you already know two layers got

thwarted.

So maybe you're also looking for,

are there better solutions at layer one

and two that could help thwart more?

Then again,

maybe your hackers are just that good.

And sometimes that's the case, right?

They know your network better than anybody

because they work for you.

Yeah.

And there's a lot of scenarios going back

to like the full scale exercise thing,

right?

Your sock may be really good.

but the rest of the organization may not

be.

And one of the things you mentioned,

right, was public communications.

How many times have you seen a company

get hacked?

And the only way the customers find out

is when they can't access the company.

Like CNA insurance, right?

Couldn't even get to their website, right?

And some other companies like that.

You know,

is your internal marketing team thinking

about, okay, well,

we'll contact the customers.

How?

If your email is shut down,

how are you going to do it?

Do you have a backup plan?

Do you have the customer list that you

can, you know, that you can use, right?

I mean, and, you know,

I work for a really good insurance

company, USA, right?

They have a great security department over

there.

And one of the things they had was

they had all the,

a lot of the stuff written down.

it was literally in binders right you know

i mean for that day when you know

they they expected anything to happen up

into well we can't even access x y

and z right and if you look at

solar winds the attack of solar winds

right where they took out people's active

directory like the whole active directory

you could very well be in a situation

where you're not logging into anything

You know,

you're not getting into that SharePoint

portal with all of your plans on it,

right?

You need to have a ready to go

solution.

So full scale exercises around the whole

company are a very valuable thing.

Yeah.

What coming out of a major exercise I

did once was like all of the physical

security for the organization was voice

over internet protocol phones.

And so it's like, yeah,

the network's down and they're like,

but that means nobody can call us.

And you know, it's funny,

it's like you and I are both ex-military,

right?

So we always know there's like, you know,

three different fallbacks on

communications, right?

The blow up goes down,

you pick up the radio,

you pick up the radio,

you do this one.

I mean, you know, so for example,

do you have other people's cell phones

numbers with you?

Or is it on that SharePoint portal on

the website, right?

Or is it in a written binder that

you can go access and go,

here's all the actual phone numbers,

right?

One of the basic things for a SOC

team to do, right,

is write down the actual phone numbers,

right?

I completely agree, Jason.

I think, again, you know,

what came out of that exercise was a

year later,

I got to walk through their physical

security response center.

And they're like, oh,

and here's our hardline phone systems.

And I'm like, you're welcome.

Well, and you know, it's,

I will say one thing too, and just,

you know, as, as we're,

as we're looking at this,

it is okay to find things wrong, right?

One of the,

one of the things you see in the

military when we do exercises,

no thin skins,

everybody's going to make mistakes, right?

Everybody's going to make mistakes.

There'll never be a perfect,

if you have a perfect exercise,

it's like getting a perfect audit.

You worry more about

the perfect audit than you do about the

one with the actual flaws.

If I ever had a perfect exercise,

I would be terrified that that was not

done correctly or that we missed stuff.

I would say leaders out there,

you want to find things wrong.

You want to be able to take that

and push it back into the process like,

hey, we found this, Daniel came in,

we did the exercise, we found this wrong.

We need to look at our risk assessment

process because we didn't ask these

questions during the risk assessment

process.

When we went out and did our annual

review of these controls around the

system,

we didn't ask them about how you're going

to contact the customer if the network is

down.

And so not only are you getting an

exercise out of just the SOC,

there's many,

many other advantages that you get out of

this, many,

many other collateral benefits that you

get because of this.

Yeah, completely agree.

And honestly,

from my perspective is if an exercise goes

perfectly.

Um, and again,

I go back to the goal, right?

If you're checking a box for regulator,

um,

Right.

You know,

do do the take the layup if that's

what you need.

But don't let that be your only exercise.

Right.

Also,

do things that you know will challenge you

every time you do a new response plan

exercise.

I mean, that's just a no brainer.

I mean,

If you've never practiced it,

do you really wanna find the holes in

your plan when you're under the gun,

the bad guys got your network locked down?

That's just not the day to be learning

lessons.

You're gonna have plenty to learn already.

And that's a lesson you need to practice

too.

What happens when you hit the tipping

point and your company can't recover?

Do you actually practice that scenario

with executives, right?

One hundred percent.

I love, you know, again,

one of my favorites is if you go

into a company and they're not really have

if they are not really thinking through

things, you'll find an attitude is, oh,

we'd never pay a ransom.

And I'm like,

if your choice was to pay one dollar

or the organization folds tomorrow and

everybody's out of work and your customers

have no

no supplier, whatever you do for a living,

you wouldn't pay that dollar.

Yeah.

If you ever had a CISO tell you

they wouldn't pay a ransom ever,

I think it's time to find a new

CISO.

You have to be pragmatic enough to know

that sometimes the best

option is unpalatable and if that is the

option we have to take for the good

of the organization again i think that i

think that leadership team that has that

attitude of we would never pay a ransom

and they go down in flames for that

is going to get sued by their shareholders

right i mean they didn't do the thing

that was right for the organization

Well, and look at when companies fail.

Look at Enron or something of that nature.

And again,

it's very rare that companies completely

fail because of cyber.

It's not a common thing, right?

They're hurt a lot of times, like really,

really bad.

But there's not really as many businesses

collapse completely.

There was a university, I think,

in the Midwest that went completely under

because they just couldn't pay the ransom.

They didn't have the insurance, right?

So they were just completely out of

business and they folded.

So if you don't think through that

scenario of what that's going to look

like, you know,

and how you're going to do it,

because there's other things you need to

consider aside from paying the ransom,

right?

You know,

you have double extortion attacks.

You have triple extortion attacks.

Who's going to negotiate on your behalf?

How are you going to contact the cyber

insurance company?

You know,

how are you going to deal with that

claim?

when it's over, right?

Look, Merck had to go to the U.S.

Appeals Court to eventually win their

claim against their cybersecurity

insurance company.

Are you doing all the things that you

said you would do in that insurance

agreement so that when the time comes,

you are covered for these kind of things,

right?

You're not drunk driving,

so your insurance is going to cover it,

right?

Yeah, one hundred percent right.

And I think one of the other things

is, you know, in smaller companies, let's,

you know, I think the bigs, you know,

once

If you can't rebuild your business from

scratch, you're at a point of, you know,

you gotta be thinking through how do we

prevent failure, right?

You know,

if you could just close up shop and

open a new shop tomorrow and not,

you know,

that may be not the same situation,

but one of the things I find,

let's say you're a more of a mid-sized

company and you've got a,

let's say you hire somebody to do your

response, your cyber response.

Are you exercising with them?

Are you practicing that this, hey,

I've got this situation,

let me practice engaging that team

And if you're one of those response

companies,

one of the things you should have is

you should be offering exercises for them,

especially if they're not using your

services regularly.

to get that annual practice together and

reinforce the value you're providing that

customer, right?

Because if they don't, I mean,

that's when they stop paying you, right?

When they're like,

why do we keep paying this company year

after year and they don't do anything for

us?

So kind of going back to my book

on customer-driven leadership, right?

Be proactive and say, hey,

We noticed you didn't use any of your

cyber response hours this year.

We're going to do an exercise with you

and let's practice together so that if

something should happen,

you know how to engage us and everything

goes smoothly.

Yeah, and the last thing I'll add, right,

is that every time you do these things,

whether it's a tabletop, a call,

just a call, right,

when you do it on a call,

or even if you go all the way

up and do a full-scale exercise,

the other thing that you get out of

this as a cybersecurity leader is more

interaction with the board and executive

leadership.

right and it's good interaction right so

okay you did a great big exercise well

now it's time to brief the board on

the great big exercise not only are you

showing you're adding your value to the

discussion right you're you're you're also

educating the board and you're educating

other executives who may not and look

let's be fair about this right unless your

business is cyber security your executives

don't think about it on a daily basis

why well because we want them to think

about scaffolding right we want them to

think about trucking we want them to

all the things that pay us and security

to do our thing we need them to

be better at than us right they need

to be better truck drivers they need to

be better so they're not thinking about

cyber security so anytime you can get that

opportunity to interface right to to to

you know to discuss cyber security with

them it's a great opportunity and you

should take it and these are perfect ways

to do it

And it's reciprocal as well, Jason,

because I think just like you said,

the transportation company isn't thinking

about cybersecurity at the executive

level,

but also the cybersecurity people are

usually very ignorant about what the

business does, how it makes money.

And so it's gotta be both ways.

I have to understand your needs and how

we make money

So that I can offer the right solutions.

Because again,

there's not unlimited things to spend

money on.

But if you tell a CISO that he

has an unlimited or she has an unlimited

budget, she could buy or he could buy.

Fifty thousand solutions.

And honestly,

that could lead to a compromise just

because.

some of those solutions are going to clash

and create vulnerabilities as well, right?

So, you know, you have to be strategic.

And again,

you have to be able to communicate why

this solution is important, right?

Absolutely.

Yeah.

Awesome.

So, Daniel,

it was awesome having you on today.

I really appreciate it.

I'm going to also in this video in

the description,

we'll have contact information for Daniel

and anything else you'd like to add,

Daniel, before I let you go.

Yeah, just in general,

I don't just break things for a living.

I love to I love to solve impossible

problems.

So that's also what that business

interrogator does is just come in and

challenge the thinking

You know, being a friendly disruptor,

pre-thinking what could go wrong and where

there might be some hidden opportunities

in your businesses.

Well,

I think if I was going to call

someone for it, I'd call you,

especially the guy who interrogated

Chemical Ali.

So I'll leave that one on there for

everybody to look at.

Yeah, thank you for that.

Yeah, no worries.

All right.

Awesome.

All right.

Well, thanks, Daniel.

You have a great day and I appreciate

it.

You too.

Cyber Talks - Break Things Safely: A High-Value Cyber Exercise Program with Daniel Hammond
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