Random Access Memories

Most leaders spend their careers trying to prove they're good at their jobs. But Assaf Keren does something different, he teaches his managers how he's failed.

The current CSO of Qualtrics and former CISO of PayPal has spent more than two decades in security, but some of his strongest beliefs about leadership didn't come from the things he got right. They came from burnout, bad decisions, difficult feedback, and learning to let go of the need to be the smartest person in the room.

In this episode of RAM, Assaf joins Jake Bernardes to talk about the stories behind his book and the leadership philosophy they created.

That includes asking employees to tell him when he's wrong, telling leadership what he intends to do instead of constantly asking permission, and an annual ritual his team has learned to dread: Assaf publicly grading his own performance. One year, he even went to his boss and asked to be rated lower. But some failures cost more than a performance review.

Early in his PayPal career, Assaf was working across Israel and the United States, essentially working two shifts every day. Good nights ended around 1 a.m. Bad ones at 3 or 4. Then he'd wake up and do it again.

He did that for a year.

Eventually he was physically ill, emotionally reactive, unable to think clearly, taking 15-minute power naps between meetings—and closer than he realized to leaving cybersecurity altogether.

Compounding that experience was something else he'd carried quietly for years: PTSD. During COVID, Assaf learned that an employee with PTSD was afraid to disclose what they were experiencing. So Assaf wrote a message to a PayPal Slack channel with roughly 40,000 people explaining his own experience.

Then he stared at it, for three days. His extended family didn't know. His colleagues didn't know. He worried his leaders might see him differently. 

Eventually, he pressed Enter, shut his laptop and walked away. Looking back, he says: “That was the moment I started healing.”

Memory 006 is a conversation about failure, burnout, vulnerability, mental health, ego and what it actually means to lead people through a profession built on uncertainty. 

In this episode:
  • Why Assaf calls English a low bandwidth language, and what it taught him about giving feedback
  • The year he worked two full shifts a day, Tel Aviv mornings and US nights, until his body forced him to stop
  • Why he asked his own boss to rate his performance lower than expected
  • The Slack message to 40,000 people that he sat on for three days
  • What a submarine commander's book taught him about intent based leadership
  • Why he believes the entry level security career is disappearing, and what that means for the next generation of leaders

What is Random Access Memories?

Technology isn't built by companies. It's built by people.

Random Access Memories (RAM) is where technology gets personal. Host Jake Bernardes sits down with founders, CISOs, engineers, operators, investors, and community builders to explore the stories behind the products, the pivots, the failures, and the moments that shaped their careers.

Whether we're talking cybersecurity, AI, startups, leadership, or life outside the office, every conversation asks the same question:

What shaped the person behind the technology?

New episodes every week.

Presented by Hubscale.

Jake: Hi, welcome to another episode of
Random Access Memories, Stories That Bite.

I'm here today with Assaf Keren, CSO at
Qualtrics, good personal friend of mine

and the author of this, which is what
we're talking about today.

It's his book. So I am going to start the
same way I start all of my podcasts.

Which is, I'm going to ask you to
introduce yourself, and I'm going to ask

you for your hero, whoever that might be.

And your hobby, what you do for fun, which
is not security.

Assaf: Great. Hi everybody. Nice to meet
you, nice to see you, or not see you.

I'm Assaf. I like to say that I do
security stuff in Qualtrics.

On the side, I also write books, but
that's okay, that's kind of a newer thing.

My hero is my wife.

Jake: That's a new one. We've had parents
and grandparents a lot.

I don't know if we've had a spouse yet.

That's interesting. Your wife is also
super talented.

I remember, your house is insane.

Assaf: She is extremely talented. And
she's my hero because she's been dealing

with all of her things, and being an
artist is really hard.

Jake: Yeah.

Assaf: And getting traction. When you're
an artist, especially when you're an owner

slash artist, in the sense that you run
your own art business, you don't just

paint and somebody else peddles it. It's
marketing, it's sales, it's logistics,

it's a ton of other things. On the flip
side of all of this, alongside that, she's

also been supporting me for the 20
something years I've been doing security.

And as you know, security is not an
eight-by-five or nine-to-five kind of job.

It's very, very different, especially with
tenure.

More travel, more customer engagement,
conferences, incidents, all of those

things. And she has managed to do both of
these things, as well

as helped me raise, and I helped her
raise, our three kids.

So she's an amazing person.

Definitely my hero.

Jake: I'm going to come back to that one.

And your hobby?

Assaf: I have two major hobbies. Okay,
actually three major hobbies.

And this is new. If you would have asked
my wife, or talked to me, four years ago,

pre-pandemic, let's call it that way,

what my hobby was, she will tell you it's
work.

Jake: Yeah. Okay.

Assaf: But I have come to an understanding
that I need something outside of work to

help me ground myself.

Jake: Yeah.

Assaf: And I found a few things.

One thing is baking.

Jake: Oh yeah, your bread. I remember
there was bread in the oven for Shabbat,

ready. Yeah, I remember.

Assaf: The other is playing the guitar,
exactly what I need.

And the third is rock climbing.

Jake: And you live in Utah, which is not
bad for climbing.

Assaf: Right. When I went to work for
Qualtrics, they said, you have two

options. You can go to Seattle, or you can
go to Salt Lake City or Provo, where the

headquarters is. And it wasn't even a
question. Okay, we're going to Salt Lake.

Jake: I can get on board with that one.
Cool. You wrote this, and I've read it

a couple of times, which I think is worth
reading. I'm going to plug it properly on

video before or after this podcast. But
why did you write it?

Assaf: I've been interested in writing a
book for a long time.

Every time I stepped into, like, what
would I want to write about, I had this

self-talk that said, you have nothing new
to contribute to the industry.

Everything has been written already.

Jake: Yeah, there's a lot of books out
there.

Assaf: And so I sat on the idea for a
long, long time.

Then about two, three years ago, I got
into this understanding.

I have it at work, and I've been doing it
for years and years.

I've been doing it since I was the CISO of
PayPal,

and I've been doing it as CISO of
Qualtrics.

Every time we have a core of new managers
in my team, I bring them to a talk that I

call My Failures as a Manager.

Jake: Okay.

Assaf: Which is a series of stories of how
I failed as a manager.

And this is basically, let me tell you
about how I failed so that you learn from

it. I'm not saying you won't fail on your
own, but when you fail on your own, at

least you recognize the pattern.

And you know it's not something that
happens just to you, and you're able to

more quickly deduce how to move on from
there.

And if you're able to learn something from
the talk, then great.

It's a bunch of stories. Some of them made
it to the book, some of them haven't.

I sat down and started saying, okay, I'll
just write the stories.

So I wrote the stories, sat down and typed
a lot, mostly on airplanes.

And then somehow it distilled into
frameworks.

There are frameworks that I like to use,
like optimism,

grit and curiosity, execution,

change management, diplomacy, and
financial acumen.

All of these things made it in as the
frameworks in the book.

And these are things that I haven't
invented. These are things I've picked up

as a security leader from other people
around me.

But they're frameworks I like to use when
I lead. The moment my mental dam broke, I

said, oh yeah, this might be worthwhile

to somebody other than me, it kind of
flew.

It was two or three months of writing,

another year of editing. Yeah.

Jake: Yes, you need technical skill,
right? All of us are nerds at heart.

I mean, your book's even got binary on the
front of it.

Assaf: It does. Security by its nature is
a technology oriented or

technology based profession. So to be a
security person, you need

to be technical. But security leadership
will not be solved by another vendor, or

by understanding the threat model better,
or by

having deep knowledge in crypto. It's
really important and it's valuable

if you have it.

And I doubt that you will be successful if
you don't, unless you have really good

people underneath, which I've also seen.
I've seen security leaders with no

technology or very little technology
know-how, but ones that are really good at

bringing the right people in and enabling
and trusting them.

But they're kind of lost on the ability to
challenge.

But if you want to be a leader of people,
you're going to end up having to deal with

the human problem, not with the technology
problem.

Jake: Because the next thing, I think I
read you said about 15 times in this book,

which I thought was interesting, is you
keep talking about if you want a career

that spans decades. You're almost
obsessive about the fact that a career

should be long-lasting, that it shouldn't
be short and burned down.

Why keep saying that?

Why keep talking about this whole, let's
have long, tenured, decade-long careers?

Assaf: If you're able to work for five
years and make enough money to support

yourself and your family.

Jake: You would need to have decades of
careers, though.

Yeah.

Assaf: But if you want longevity, and I
would say even more important, if you want

longevity in this, society needs good
leaders with experience in this

profession, because we are more and more
reliant on technology.

And as we're reliant on technology, and
reliant on the fact that

technology does what it needs to do.

And security is one aspect of trust, which
is a whole different conversation we can

have, but security is one aspect of it, a
big aspect of trust.

The ability to go in and do that well
requires experience.

So personally, I think people should
strive towards long-lasting, fruitful

careers, because they need to be
self-sufficient and support their family,

and they need to bring value to the
companies that they operate in.

But as a society, I think we want to have

people who have been doing this for a long
time.

I am very worried that in three to four
years, it will be very hard for

somebody who just finished a degree at
university to find a job in security.

Jake: Because most of the entry-level work
will be agentic.

And therefore, I have to say, my deeper
concern, which might be where you're

going, is if no one can get entry-level
jobs, how do we have leaders in the future

who never got foundations?

Assaf: Exactly.

Jake: Like, where is the future of
leadership? Most of us came up in some

kind of pen testing, SOC, some kind of
foundational career path.

Assaf: Somebody gave us a break, and we
were able to take that break and move it

forward. I think we're going to have to be
a lot more engineered about it in the

future, or designed about it. And for
that, we're going to have to bring back

the apprenticeship model. And for that,
you need 10-year leaders who will be good

enough at what they do.

And enough experience to bring somebody
in, and to understand that they need to

bring somebody in, because they won't be
there in five to 10 years, and teach them

the art of the job without having to do it
on a day-by-day basis.

Because you don't do triage anymore in the
SOC, because there is an agent that does

it. You don't have to.

From anecdotes, you don't do the evidence
collection DRC work.

You do the compilation and the
conversation around comps and controls.

There is a uniquely different set of
entry-level that starts much higher,

or will in the near future. And I really
believe that's the future.

So even there, the need to have tenured,
experienced people in

this day and age is even more acute.

Jake: Yeah, I agree. I completely hear
your point. One thing that I think was an

interesting recurring theme is that you
are an incredibly vulnerable individual.

Take that in a positive way.

Assaf: My shoulders are shot.

Jake: You're a massive advocate for taking
criticism, which is rare in leadership.

I know a lot of CISOs, we both know a lot
of leaders in high-power, high-profile

roles, you can't tell them they're wrong.
Why?

Why ask everyone to tell you you're wrong?

Assaf: How else do you learn?

Jake: Is it not a risk when your team are
identifying everything you're doing wrong,

and it becomes exposed above that, that
maybe some of your team are more apt at

your own leadership role than you are?

Assaf: I'll tell you a story that didn't
make it to the book.

Jake: Okay.

Assaf: I'm Israeli. And PayPal used to
have this thing called TLP, the Technology

Leadership Program, where people at

mid-engineering levels would rotate into
this leadership program.

It was a very specific program to select
people.

I think you had about a thousand
candidates a year, and 12 got in.

It was a very highly selective program.
And then they would rotate for two years,

and every half a year they would rotate
with a different leader and learn

different aspects of the role. And I had a
TLP cohort working with me for

half a year, and we were flying out to Tel
Aviv to meet the team there.

And I had one or two directs in Tel Aviv.
We go into a meeting room.

It was me, her, and two of my directs
there, one of my directs from the US, but

he was also Israeli, and somebody from
there. And we start to have a

conversation. It was in English.

Now, English is a low-bandwidth language,
unlike Hebrew.

Jake: Low bandwidth? What do you mean,
low-bandwidth language?

Assaf: The amount of words you need to
convey an idea.

Jake: Okay. Yeah, okay.

Assaf: It's higher in English than it is
in Hebrew.

Jake: Hebrew. Yeah, I know that much.

Assaf: It's also slower.

Jake: I sit in enough exec meetings in Tel

Aviv to know that it's slower, don't
worry.

Assaf: And so we were having this in
English, because she was in the room and

we were being nice. At some point she
stops the conversation and looks at one of

my directs. How can you talk to him that
way? He's your boss.

It's like, what? What did I do? And she's
like, you told him he's wrong.

And he looks at her like, but he is wrong.

Jake: There's something very Israeli about
that statement that people who've never

worked in Tel Aviv won't understand.

But, yeah.

Assaf: And she looks at me and says, are
you okay with him telling you you're

wrong? If I'm wrong, I want to know I'm
wrong.

Let's have the conversation. It was a
funny cultural divide moment.

Jake: It doesn't happen in the US, it's a
rare cultural thing.

Whereas obviously it's so normalized
inside Israel that people challenge norms

and say what they think they must.

Yeah.

Assaf: It's interesting. One aspect is I
grew up in that culture.

The other aspect is I truly believe that
I'm not the smartest person in the room.

Jake: Which in itself probably makes you
the smartest person in the room, realizing

you're not the smartest person in the
room.

Assaf: I know that I have people who are
smarter than me.

I might be better than them in some
things, I might know organizationally

better, but I'm not the smartest person in
the room.

And I'm there to make sure they're more
effective and that we're hitting the goals

and the outcomes we've put in front of us.

And so we sometimes have difficult
conversations, for me and for them, about

challenging each other and telling people
that they're wrong.

And that's fine. It's more than fine. That
is the baseline of leadership

in my mind. It's so ingrained. And if you
get to a point where you

tell your leader something and they lash
out at you because they don't want to be

seen as stupid or wrong, that's a bad
place.

Jake: So I agree, and I wanted to get to
this point because I want to move the

conversation around. I agree, and I build
and foster this.

I think that not being the smartest person
in the room is the idea that if you're

good at hiring, you should never be the
smartest person in the room.

The people in your team should be better
at their specific domains than you.

That's the whole point. And I also agree
that you should embody this culture where

you can be challenged. The problem we
often have is these kind of stupid 360

feedback things where everyone just writes
positive things.

I ask my team, what am I bad at?

I don't care what I'm good at, because I
can probably work that out myself.

What am I bad at? But the interesting one
is you then go on.

So that's just disruption, right? And you
talk about in this book how you disrupt

downwards and upwards, and you call it
intent based leadership.

That's what you've got here, which I'm
fine with, your version just now.

The next bit scares me. The next bit says,
well, if I'm doing this in my team, I am

going to effectively disrupt the CEO or
leadership beyond me.

If they're wrong, I'm going to act in a
way that's right.

Talk to me about that, because that's
basically what you're defining intent

based leadership as. It's acting within
parameters without waiting for permission.

Assaf: Intent based leadership. And shout
out to probably one of the best leadership

books I've read in my life, and a
genuinely amazing person I had the

privilege of meeting, a guy called David
Marquet, who wrote a book called Turn the

Ship Around. He was the commanding officer
of a US submarine.

And that's where I took a lot of that to
heart from.

My intent based leadership is saying.

I'm not going to ask for permission to do
things.

I'm going to tell my leadership what I'm
going to do.

And instead of asking, can I do X, it's
saying, and language is really

important, I intend to do this.

Jake: What if the answer is don't?

Assaf: Then the answer is don't.

And then we have a conversation about it.
Okay.

Jake: So it's still not act without
permission. It's make an assertion about

what you're going to do.

Assaf: Make an assertion about what you're
going to do. And what I found is, the more

capable you are, the less interruption you
get. If you're not capable, you're going

to get a lot of interruption.

And there are parameters. If I'm going to

take down a feature for four months that
20,000 customers are relying on because

there's a problem there, then I'm probably
going

to go in and have a conversation with
people.

But if we found a critical vulnerability
in a feature that's being used by two

customers, take it down. But still, by the
way, go and say,

hey, I intend to do this, and we're going
to shut it down at this point in time.

Communication and diplomacy do not go away
with intent based leadership.

You still need to communicate,

and you still need to understand who
you're talking to.

Jake: And have you ever had problems with
that?

Because you've worked in some
organizations

with some pretty strong leadership
characters.

Assaf: Yes.

Jake: And so you've definitely worked

with some notoriously strong individual
characters.

Assaf: I think the good leaders I worked
for were very appreciative of that,

even the strong-willed ones. The ones that
I did not vibe with, or did

not succeed with, were the people who had
not managed to manage their ego in a way

that allowed them to accept it.

Jake: It's interesting, because you're
obviously so open to criticism yourself,

you see it as a character flaw when people
aren't able to take criticism or to take

instruction. You're right, but it's
interesting the way you see it, because I

know how you think you're seeing it, the
way that you think.

Assaf: I'll tell you this. This is a
moment that terrifies my team.

Every October, actually even earlier than
September, I sit down and write my

analysis of the year that passed and what
I want to get in the next year.

It's divided into organizational outcomes
and personal outcomes.

I would like to do one, two, three, four,
five.

And the organization should achieve one,
two, three, four, five.

And really focusing on outcomes. My pet
peeve is when people tell me what they've

done versus what they've accomplished.

Jake: Yeah, okay.

Assaf: And I rate myself, I always rate
myself. When you take a look at the year

past, it's like, I said I'm going to do
this, but I didn't.

I said I'm going to do this, and I did
part of it.

And these are things I didn't say I'm
going to do, but I did.

They were changes that happened throughout
the year. And most of the time I send it

to my team, hey, this is my
self-reflection for the year.

Failed, failed, failed, partially failed,
failed. And they fear that moment.

Because if I fail, I'm nicer with them
when it comes to their assessment.

But I also send it to my leadership team.
I actually had this year, I had to go to

my boss and tell him I wanted him to rate
me lower.

Jake: You are a special and different
individual, is all I can say.

Assaf: Because I think that creates
clarity.

Jake: You went to your boss and said, rate
me lower. Yes.

And he did, or she did?

Assaf: I don't think he took me as low as
I asked him to, but he did.

Jake: Why? I get that you want to be seen
the way you see yourself, I get that bit.

But if the score is someone else's
reflection of you, you could be wrong.

Maybe you did better than you think you
did,

because their perception is different to
yours.

Assaf: Maybe, and valid, completely valid.
And I'll have that negotiation.

In the end, he rated me higher than I
thought I should be, but lower than what

he initially came in with. My boss is an
amazing person.

Brad is a really good human being,

so he has a hard time rating people lower
than most people would.

Jake: Most people would.

Assaf: But when I look at my role and what
I've done,

I think the message to the organization

is more important than my personal peace.

Jake: Because the message to your
organization is, we didn't accomplish all

these things, because there may be other
underlying things that we need to work on.

Assaf: But we have some massive things we
need to work on, like any other

organization. And those massive things
need acknowledgment.

And if we're not acknowledging them in a
way that's fruitful, part of it

is also how he's rating me as the chief
security officer.

And I'd rather take it in my rating and
prop my team up and give them higher

ratings, because in their individual areas
they succeeded.

Rather than the other way around.

Jake: Yeah. Because the logic says, or at
least my thoughts always are, success is

an individual thing, failure is a
leadership thing. And we have to own these

things. You have some thought processes
that people listening to this will just

not be able to get their heads around.

I know you quite well, but I think it's
fascinating.

Assaf: I'm happy to step into a
conversation with anybody.

Jake: I think it's fascinating. I'm close
to time, so I want to come to a couple of

things. There are two stories in this book
that I think are really interesting.

Assaf: Just two stories?

Jake: Well, there's lots. Actually, I
found the wall one the most interesting to

start with. For those who haven't read it,
you'll have to read the book, but there's

a point where you can't get over a
two-meter wall in Israeli IDF basic

training, and then eventually you can, for
a different reason.

It's very interesting. But there are two I
want to talk about.

One is, you've had a pretty illustrious
career with some pretty crazy companies.

You burned out at PayPal, which is a
section that takes on several different

parts of this book. And then you also sent
a Slack message about what went wrong, or

why I did this, or how I felt.

Assaf: How I felt, yeah.

Jake: And sharing that publicly, I think,
is really important.

But it also says a lot about who you are
as a leader.

Assaf: Look, I sat down and wrote them in
the book. It's public.

By the way, I think that's part of my
healing process.

Jake: It's interesting.

Cathartic.

Assaf: Yeah, I can see that. I'll talk
about that second story in a moment, but

let's start with the burnout piece. I was
doing security operations when I joined

PayPal. I had an almost 10-year career at
PayPal, ended up as CISO, but started in

security operations out of Israel. Woke up
in the morning with my kids.

So I would put them in kindergarten, then
drive into Tel Aviv and do a day of work

in the office with the team in Israel. And
then around 4 p.m.

I would go back home, spend an hour with
the family, and step into my

second shift in the US.

And I was so.

Afraid of losing control. I was afraid
because I was new to PayPal,

insecure in my position there. I was
afraid because my directs were in

Scottsdale with my boss, and I was afraid
that would create a short loop

that would put me outside of the
conversation. And I was afraid because I

wanted to be in these meetings they had at
those times.

And I didn't want to be the limiting
factor.

And I didn't allow myself any time

to actually go out and shut down.

Jake: Just to be.

Assaf: Just to be. And I would do days.
The good days would be up

to 1 a.m., bad days up to three, four a.m.

Jake: And then start again the next day.

Assaf: And then start again the next day.
I did take Sunday off, because in Israel

Sunday you work, but I did work Fridays,
which you usually don't work.

So I was working fully US hours and
Israeli hours to a point.

And I remember doing power naps on the
sofa for 15 minutes between meetings.

How long did I do this for? A year. And at
the end of that year, we actually moved to

the States. I didn't solve it by getting
better at putting boundaries in place.

Now, I can have a conversation about that,
but I solved it by moving to the

States, because that was the right thing
to do.

But I was physically ill.

I couldn't think well. I was reacting
emotionally to everything.

I was not feeling well, and I was at the
breaking point.

If we would not have moved to the States,
which was a moment

I'm very appreciative of my boss at the
time for, because he.

He also saw that I needed something to
change, so he helped create that movement.

Moving helped, not just because it was a
moment of, now I have to.

Doing security operations in the US was
much easier, but it also forced me to take

a month off, just to get through the whole
move,

and that really helped ground me and
replenish myself.

So that was a really bad moment. And I
still remember, even

talking about this, I remember the
tiredness, like you're always tired.

And I think as I grew as a leader and I
looked back on

that moment, I understand just how close I
was to leaving the profession.

And instead of being angry at him or being
disappointed, it was a

conversation around, you're fine, let's
find your path forward and support.

And I think that's very important, from
that moment.

Jake: Yeah, it's interesting. I was saying
before we start recording, I've had my own

moments recently where I've questioned, am
I burned out? Am I doing too much?

I was reading again on the plane on the
way here, and I was thinking, gosh, I have

some of these indicators. You list all of
the symptoms.

It's like.

Oh gosh, I have these. And I think those
are important moments of self-reflection.

But I also have people in my team who I've
looked at and gone, actually, sometimes

maybe they have some of these and I
haven't really realized it.

We don't look around us enough. I think
what's happened, whether we call it

wokeism or whatever it might be.

We've become obsessed with talking about
mental health and well-being, but it's

become much more of a shallow conversation
than an actual meaningful thing.

We tell our employees, oh, be healthy, go
and keep well, have time for yourselves.

We don't actually really mean it. We say,
do your job, and do this too.

It's like giving them another task. So I
think that's where it follows on.

You had these moments and then you got
through it, partly by moving countries.

And then you sent a Slack message. Tell
people about the Slack message.

Assaf: The Slack message is connected, or
maybe somewhat different.

I've been struggling. I'm Israeli. As an
Israeli, I served in the Israeli

Defense Forces. There are some stories in
the book from that

time as well. And I have been carrying
PTSD.

And this is something that I have not been
open about.

For a long, long, long time.

And I have been in therapy for a long
time, and it helps me a lot.

And creating that space for people to
admit

that is a really important piece as a
leader.

Jake: Can I ask a how-to? Because a lot of
people say that, and I think it's good,

but how do you find a therapist? How do
you find one you can talk to?

What was that conversation for you? How do
you interview them?

Assaf: In time you find the right
therapist. Maybe not my current therapist,

because I had to move to a therapist who
will do remote, since I can't.

Jake: Yeah, can't physically be there.

Assaf: So I had to find somebody.

But my previous therapist was a Vietnam
vet, a naval.

Officer, so he understood the specific
things.

And we had other things in common. It was
amazing, breakthrough moments with him

from here until kingdom come. But we were
in the middle of COVID, the start of

COVID, and one of my employees comes to me
and tells me, hey, we have an employee on

the team who's afraid because they have
PTSD.

This COVID thing that just came up is
creating more stress, and he's back on

medication. He's afraid he's going to be
in a not-good place, reprimanded, he's

afraid to admit it. And in my mind, what
can I do to help him

feel better? I sit down and I write this
long message.

And again, at this point in time, my mom
doesn't know I have PTSD.

My family doesn't know I have PTSD. My
wife does, my children do, but that's

about it. My therapist does.

Jake: This was at Qualtrics?

Assaf: This is at PayPal.

Jake: Oh, PayPal.

Okay.

Assaf: And there is a Slack message with
40,000 people on it,

and I write this long one.

Jake: This is like the general channel,
effectively.

Assaf: This is the general channel. It was
a COVID channel, but a long one.

Name is Assaf, this is what I do, this is
what I went through, this is what I'm

dealing with. And it's okay, because I was
a VP in the company.

It's a leadership moment. So it's okay to
feel this way, and go get help.

If you need any support, then talk to me,
or if you need any support, talk to these

HR resources. And I write it.

And I can't press enter. And I'm sitting
on it for three days in that channel,

scared shitless about what happens after.
Do my leaders see it and

think that I'm not as good because I have
PTSD? Does my team see it?

Does it get to my family? How do I deal
with it?

And three days. After three days, I'm
like, okay, this is the right thing to do.

Press enter and walk away. I shut down the
laptop and move on.

And I think, if you really ask me now,

that was the moment I started healing.

Jake: And how long between you leaving the
IDF and pressing enter?

Okay, leaving full-time military service
and pressing enter.

Assaf: Leaving full-time, I left in 2007.

Jake: Gosh, that's 13 years coming, that
stuff.

Yeah.

I know what happens a little bit,

but can we talk about the reaction, the
trauma reaction?

Assaf: People were amazing about it.

Jake: Crazy amounts of comments, right?

Assaf: Crazy amounts of comments and thank
yous and support.

After that, I actually stepped into being
one of the exec sponsors

for the FRI VRG, which is the group for
people with disabilities and

neurodiversity. I stepped more into this
world in support of people like me.

It was the right thing to do for me, and
the right thing to do for my team.

And we live in a world where stress and
trauma and anxiety

are the bread and butter of what we do for
a living.

Jake: That is a deep statement. Stress,
trauma, anxiety are the bread and butter

of what we do.

Assaf: It is. You context switch all the
time.

Every time there's an incident, you're on
calls. You can't really plan.

I have this very interesting conversation
with engineering leaders who are like, we

just want clarity on what we need to fix.

Fuck if I know. We'll find out next week.

It could be a zero-day RCE tomorrow, and
I'm going to take all of your resources

and ship them there, and all of these
things we're talking about are not

relevant anymore. So there is this
constant thing, and if we don't build

resiliency, and if we don't de-shame the
conversation around mental health, because

it is. I'll tell you this, even after
that, I didn't talk to my

family and tell them about my PTSD for a
long, long, long time.

Because PTSD is one of those shameful.

Illnesses. It's like, I didn't get hit by
a bullet, I still have all my

limbs, I'm still alive, so.

So why should I?

Why should I? I just have this reaction,
this mental reaction, who cares?

And I was afraid of their reaction to it.

And so we need to de-shame the
conversation around anxiety, around

stress, around trauma, and help our team
understand it's okay.

And that was the guiding thought when I
sent that message, and part of the guiding

thought of putting it in the book.

Jake: It's interesting. I want to finish
by coming full circle.

So you started by saying your wife is your
hero, because she was always there for you

regardless of what happened, right? And
one of the later chapters of this book is

all about building networks of people who
support.

People who catch you when you fall, right?

I think we all think our spouses are that
person.

What's interesting is you basically said,
and I'm going to be careful how I word

this, that you didn't feel like your
family necessarily would be, because you

were scared to tell them. You were never
scared to tell your wife, but you were

scared to tell your parents and your wider
family.

So how do you build, and how do you know
you have a network who will support you,

regardless of what the statement is? How
do you know someone's there for you,

whatever you tell them, even if it's
shameful or whatever it might be, right?

Assaf: You need to find the right people

and surround yourself with the right
people.

Jake: How do you know you found them until
you tell them the thing you think they're

going to react to, and they don't?

Assaf: Well, I've had people who I thought
were friends and were in my network,

and they're not in my network anymore, or
not really high-bandwidth connectivity,

because of reacting the wrong way or being
disingenuous about things.

And so you work it out.

Jake: You work it out.

Assaf: You work it out at the time. I
don't know that there's a full process to

vet people. But I will tell you this.

A really big reason why I went to therapy
is my wife.

So it's not just about.

Jake: Because she told you to?

Assaf: Yes. It's not just about having the
people who will support you.

It was also finding the people who, in
your time of need, will tell you, dude,

you're going the wrong way, you need help.
And having the courage to come in front of

you and tell you that, because that is one
of the hardest things to tell a person.

Jake: Well, that's true love, right?
Someone who's willing to put themselves in

a difficult position, and put you in a
more difficult position, because it's the

right thing to do.

Assaf: I just heard a podcast with Daniel
Lubetzky, the CEO of KIND.

And he talked about kindness.

The person interviewing him was saying,
hey, you're kind all the

time, how does that look? And kindness is
not being nice.

You can be kind and nice,

but kindness is when somebody has
something in their teeth.

You go and tell them. Maybe that's the
separation.

Find people who are kind. And we keep
saying clear is kind, so feedback is kind.

Jake: Yeah. There's a book, which you've
probably seen, which I love, a kids' book,

called The Boy, the Mole, the Fox and the
Horse.

Assaf: I think it's a picture book.

Jake: It's about this boy who goes on a
journey, and the mole that loves cake.

But it's really famous for its quotes,
kind of like The Little Prince.

And there's a really famous quote. It
says, in a world where you can be

anything, choose to be kind.

Assaf: Yeah.

Jake: And that's one of the points they
make, that kindness is about support, even

when that support is difficult. Because
being nice is not always hard, being kind

is sometimes hard. If you could share
anything, one thing, what would you tell

people now, from everything you've
learned,

one fact or one lesson or one tip you
could give?

Pick one.

Assaf: Probably. And you'll have to read
the book for it.

State reality, inspire hope.

I think in our world we're really good at
stating reality.

We're bad at inspiring hope.

We're really bad at inspiring hope.

Jake: Clickbait doesn't work when you
inspire hope, does it?

There's no good news. It doesn't go viral.

Assaf: Yeah, no.

But even just as we're having
conversations as an industry, you know.

Jake: Yeah. Well, we like fun, don't we?

We like people who are terrified about
everything going wrong.

Well, I don't like fun.

Thank you.

I finish every podcast with a question
from my eight-year-old daughter, Izzy.

They're very rare, random and varied. So
her question for you is, who is your

favorite Disney character and why?

Assaf: The best Disney princess is Elsa.
Why?

Because my kids grew up through the Frozen
age.

Jake: It's the princess of your time.

Assaf: And I, being a parent of daughters,
I have two daughters and a son,

I think it's the first Disney film that
wasn't the prince coming.

Jake: Yeah, the princess rescues the
prince.

Assaf: And up until today, when Let It Go
comes on, or even better, I am, I am, I

know I'm heretical here, but I think
Frozen Two is better than Frozen One.

Jake: That is a bold statement.

Assaf: Yeah, I know, I have a whole
different conversation.

But even today, when it comes on the
radio, or not radio anymore, when YouTube

streams it, we sing our arses off in the
car to all the songs from Frozen.

Jake: I like this vision I've got. As a
father of a daughter, I'm similar.

Look, you are potentially one of the most
interesting people I know.

It's one of the things I commonly do when
people ask me, I say, you are one of the

most interesting people I know. You say
things and think things and do things that

make me think in different ways.

So the one you've just given me, which I'd
never heard before, asking your boss to

downgrade your performance, you are
fascinating. But I think, try it.

Assaf: Try that one. I think it works.

Jake: Well, I will. But I think you're
what the industry needs, and I think your

honesty and openness and truth telling is
important. So I've read this, I recommend

it, I'll talk about it some more
separately. But thank you so much for

taking the time. We're at RSA, so I know
the schedule is busy.

Assaf: Yeah, look, we're in my living room
at RSA.

Jake: It's beautiful. I truly, truly,
truly appreciate it.

Hopefully we'll speak again soon. But
thank you very much for taking the time.

Assaf: Thank you. Happy to be here.

Jake: Thank you. Thanks. Thank you all.