September 22, 2025 • 36 mins
Andrew Kisslo talks about his journey from marketing roles to Chief of Staff at Microsoft, sharing what it was like working in the role during a period of massive growth and change. He describes the different Chief of Staff archetypes, the importance of authenticity in leadership, and the process behind hiring his own Chief of Staff at SAP. Andrew also explains the career value of the Chief of Staff experience and offers practical advice on finding the right fit for both principals and Chiefs of Staff.
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Who Am I?
If we haven’t yet before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.
Time Stamps:
00:57 Andrew's Career Journey to Chief of Staff
01:53 Understanding the Chief of Staff Role
02:03 Historical Context of Chief of Staff Positions
02:59 Early Influences and Mentorship
03:43 First Impressions and Aspirations
05:05 The Reality of the Chief of Staff Role
09:05 Navigating the Challenges and Archetypes
13:38 Lessons from a Phenomenal Leader
18:14 Transitioning Out of the Chief of Staff Role
25:16 Becoming a Principal and Hiring a Chief of Staff
32:44 Final Reflections and Advice
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
emily-sander_1_02-11-2025_12 (00:25):
My guest today is Andrew Kislow,
and he and I first connectedbecause he was, um, recruiting
and hiring a chief of staff forhis, his team.
And, uh, he has been in thechief of staff role at his 10
plus years at Microsoft.
It was one of one of the manyroles you've held there.
Um, and so we're gonna talkabout the lifecycle of chief of
(00:47):
staff, and Andrew is wellpositioned to do that.
So, Andrew, welcome to the show.
Thank you so much for beinghere.
andrew-kisslo_1_02-11-20 (00:52):
Thanks for having me.
It's a pleasure.
It's a great topic.
I love talking about this.
So,
emily-sander_1_02-11-2025_1 (00:56):
One of my favorite too.
So just to give our listenersquick background and context,
can you just give us somebackground for, for you and your
career up to the point where yougot to be chief of staff?
andrew-kisslo_1_02-11-202 (01:07):
yeah, absolutely.
Um, currently, I'm the seniorvice president of global partner
marketing at S.
A.
P.
Um, but when I go in the wayback machine, um, before I
became a chief of staff andeverything up to that, um, I
started my career after businessschool, um, at a small startup,
um, In the dot com era, wheneverything was going to take
over the world, um, and itprogressed, um, ultimately
(01:28):
leading to a job at Microsoft,um, and had done a variety of
roles at Microsoft, everythingfrom product marketing, product
management, um, and chief ofstaff or, um.
You know, staff positions wasalways something that interested
me.
Um, and so there came a point inmy career where I found the
right opportunity at the righttime to do that.
But most of my background was inmarketing, uh, and dealing with
(01:50):
customers.
So.
emily-sander_1_02-11-20 (01:52):
Gotcha.
Thank you.
So can you just touch on alittle bit of like what you
thought about when you firstheard chief of staff, what you,
what that decision process waslike going into that role, that
whole phase of
andrew-kisslo_1_02-11-202 (02:03):
Yeah, you know, I, I kind of go back
to, um, even the history of theroles, because my first
introduction to someone that wasa chief of staff, um, you know,
chief of staff positions haveexisted probably since, um,
originally the, the, you know,as old as the military in the
Roman days, there was alwayssomeone and we've always seen,
you know, in TV shows, someonethat was the right hand in
either the mafia or even Game ofThrones, right?
(02:24):
Um,
emily-sander_1_02-11-2025 (02:25):
Yeah.
andrew-kisslo_1_02-11-2025_1 (02:25):
in tech, they actually were born
out of the origin, um, early onwhere they were called technical
assistance.
T.
A.
S.
Um, and when you really thinkback to the, um, the birth of
these tech companies, um, thatusually in a founder culture,
Microsoft Intel, uh, theyusually had someone that had to
support the founder that was thechief executive and they were
(02:47):
typically T.
A.
S.
Technical assistance.
Um, and what those folks didwas, um, Serve as a right hand
person to help everything withdemos on stage, um, to technical
directions of the product.
Um, and so my first introductionto someone that was a TA, um,
was actually in my first roleafter business school.
And the person had been a TA forCraig Barrett, who was the CEO
(03:11):
of Intel, followed Andy Grove,um, and so, um, he was
effectively a mentor for me veryearly in my career.
And I was not technical, but Ireally loved his approach to how
he, um, looked at everything inthe business.
And I was always curious, like,how do you know to look at the
business this way?
And he was like, oh, I was a TAfor a CEO.
(03:31):
And I was like, what's a TA?
And he really educated on me andstarted to open up my world of
these special, unique roles thathelp executives scale.
Um, and so that was my firstintroduction very early on.
Um, when I left and joinedMicrosoft, um, Uh, I also, um, I
remember the day I was in aroom, I was a junior person, way
(03:52):
in the back of the room, veryimportant people, um, in the
center of the room, um, and thisyoung, lovely woman walked in
and she started barking commandsto everyone.
And she was like, oh, you'refull of shit.
And oh, the numbers are wrong.
And what are you guys going todo about this?
And she walked out and I said,who was that?
And they were like, oh, that'sso and so's chief of staff.
(04:13):
And I was like, wow, like, howdid that person come in and
command a room and knoweverything about the business?
And effectively was there to notonly force multiply, but to keep
the business on track and itplanted yet another seed in me
of like, wow, that seems like areally, really unique job.
(04:33):
Um, so I was introduced veryearly on to 2 very specific
people who held that position intotally different ways.
But it piqued my interest.
emily-sander_1_02-11-2025 (04:43):
Yeah.
And it sounds like the, thethrough line of that is just you
going, they see the wholebusiness across the board
holistically.
Like how did they do that?
And that's what got, got yourattention among other things.
So us to the point where it'slike now you're being offered
chief of staff and kind of whoyour principal was and did you
know this person before and howyou interacted and set up that
(05:03):
role in relationship.
Tell us all about that.
andrew-kisslo_1_02-11-202 (05:05):
Yeah, I think, you know, in the
journey of, um, I thought Iwanted to be one.
Um, and I got advice early onfrom someone, um, who had been
chief of staff, um, very similarto maybe a listener today of
their thinking about it.
And the guidance I got early onwas, um, these jobs aren't for
everyone.
And the key thing is before youeven entertain it, um, you have
(05:26):
to know why you're going afterit.
Um, or is this illusion of.
There are super cool jobs, andyou're gonna fly on jets, and
you're gonna be in the coolestmeetings in the world.
Um, and while some of thosethings may be true every now and
then, um, that's not the job.
Um, and so you really have to goin with eyes wide open.
Um, so I did the work, uh,before I even found a job to,
(05:48):
uh, apply to, which was, um, Iknew in my career at that time,
I wanted an experience where Iwould learn how a leader thinks.
How a leader leads.
Um, and there are a couple ofthings that come along with
that.
How leaders drive culture atscale.
Um, how leaders make decisionsin the present for things that
(06:08):
are short, medium, and longterm.
So that's like decision making.
Um, and then there's, you know,the, the other part, which isn't
the fun part, but it's sofundamental for any leader is,
uh, business excellence.
How do you manage the resourcesand headcount and money that you
bring to bear, uh, to drivereally important outcomes and
really achieve a staff.
(06:29):
Fundamentally touches all thosethings.
They help culture.
They help the bottom line andbudgets and resources and
strategy.
And then they also help in themiddle rallying all the
capabilities of horizon zero allthe way to horizon three of
things that aren't that are, youknow, a glimmer in someone's
eye, but they're not here yet.
And you have to hold space forall of that.
(06:50):
Um, so that's what I knew Iwanted to get out of it.
Um, yeah.
And so I found an opening, um,for someone, um, it was in the,
in the Azure marketing world atMicrosoft.
And this was early in the daysof cloud.
We didn't really have an idea ofwhat we wanted to be.
Um, and I applied for the joband the leader said, Hey, you're
perfect.
I know you, you, you sort of cando all these things just enough,
(07:13):
um, try the job.
If you hate it, we'll findsomething else.
And I was like, what could gowrong with a pitch like that?
Um, and I did it for four years.
Um.
And it was a rocket ship.
It was really, um, I caughtlightning in a bottle in a
couple of different ways where Iworked for a leader who was a
phenomenal person and leader onculture and strategy.
(07:34):
And also for a business that wasexploding, we used to commonly
joke of we were doing thingsthat they cannot teach you in
business school.
There is no business schoolclass or professor ever.
That knows how to take a billionin revenue and double it and
double it and double it.
Um, and just having exponentialgrowth, um, while not having
(07:56):
more resources.
This is key.
We were exploding the cloudbusiness.
Um, but we were not getting moreheadcount and we really weren't
getting that much more budget.
And so how do you extract astrategy that drives that much
yield?
Um, Is it was, it was a, aninteresting ride for sure.
Um, lots of very new businessmodels and things that we
(08:18):
experimented to.
Um, but, uh, that, that wasultimately, you know, the
position that I found that I wasincredibly lucky, um, to be
honest, to find that, you know,at that time,
emily-sander_1_02-11-2025_ (08:30):
Wow.
That's amazing.
And can you just talk about, itsounds like so much was
happening so quickly in thosefour years.
And I'm assuming you tell methings were evolving at a rapid
clip.
So your chief of staff role wasevolving as you moved along.
Your principal's role wasevolving as theirs moved along.
Can you just talk about kind ofhow you progressed and, um, you
(08:51):
know, when I was chief of staff,you would have to like be in it
and like go in it and you're inkind of tunnel vision and then
you would take a breath and zoomout and go like, where are we?
What's happening?
What's the long term?
Um, and then go back in it inthe short term.
So kind of tell me a little bitabout your experience in those
four
andrew-kisslo_1_02-11-202 (09:05):
yeah, you know, I think, I think, um,
in the four years, you know, Ikind of look back and, um, um,
Every year I did it, um, therewas something different
happening in the business,right.
And at least in tacking thepace, it was.
You break down your businesskind of almost into 90 day ship
windows.
Every 90 days you're shippingsomething and that's you're
moving fast, but the externalenvironment around you is moving
(09:26):
faster.
Um, and so, um, every time thatyou put a plan out there, you
hope and pray that somethingdoesn't happen externally where
you have not to change it.
Um, and that never holds, right?
And so, um, you're constantly inthe, in the business, like you
mentioned, where, um, you'redeep in the weeds and you're
planning, uh, and then yousurface for air and you're
(09:46):
raising altitude and then youpressure drop again.
And so this, This constantparabolas, I would say of
altitude that you're in thebusiness, um, of do we have the
right strategy?
I think we've got a vision andthen you're like, like, execute
and then you pop up and you'relike, oh, my gosh, it's not
working or something differenthappened.
And you're constantly doing, um.
This, um, that's why in someways it's, it's not for
(10:08):
everybody.
It is hard.
Um, and you have to hold yourleader in the highest regard
because your job is to make yourleader and your org as awesome
as possible yet behind thescenes.
It can sometimes be utter chaoswhere you don't want.
Um, a lot of that, uh, tumult orindecision to come forward, um,
(10:29):
which is natural in anybusiness.
It's naturally in any singlebusiness.
Um, but, you know, it, itrequires different archetypes of
chiefs of staff to kind of, youknow, Come forward as well, um,
at least in some of the researchthat we did, um, when I was in
the role at Microsoft, and Ithink they're fair is there's
sort of 4 archetypes of chiefsof staff.
Um, and someone needs to flowthrough all of them, or you kind
(10:51):
of find your place.
Um, and at least in a 2 by 2,what we found was, um.
There's one thing on the Y axis,which is, um, is, um, is your
leader needing a lot of depth?
Or are they a breadth leader?
Like, are they really specificand an engineering leader or are
they kind of common?
That's one axis.
Um, the X axis is, is this anentirely new business or is this
(11:14):
an old established business?
And what we found was that witha couple of questions, it really
led to four kinds of archetypes.
Um, you have chiefs of staffthat are fixers, And they go
around and they fix stuff.
Um, you have chiefs of staffthat are Jack or Jill of all
trades and they kind of need tofloat.
And those would usually be insomebody that's a new business
(11:35):
with a lots of breath.
They're just everywhere.
They're firefighting.
Um, in that upper right.
Um, you would have someonethat's a force multiplier.
Um, and the role of a forcemultiplier is very different
than a Jack and Jill of alltrades.
They're in the opposite parts ofthe quadrant.
Um, and then the final one isring master.
bringing everybody together andkind of driving and being an
(11:55):
emcee.
Um, and I think that in my fouryears, I floated through all of
those modes based on the, onthe, on the business.
And sometimes it was seasonal.
Sometimes it was like year one,I was just a fixer.
I had no idea what to do.
And then I was like, I think Igot this.
I'm now a Jack and Jill of alltrades.
Cause I can kind of see it.
And then you can kind of see,Oh, now I'm maturing.
(12:16):
Um, um, but archetypes werereally helpful for me to
understand.
Um, because the job is thatnebulous.
It's a living, breathing thing.
Um, and so I think for peoplewho come into the job, um, with
the expectation of my job isvery codified and it's the same,
not this kind of job.
Um, you really need to almost beokay with, um, that wide
(12:39):
aperture.
That's kind of constantly movingin and out, um, because it
requires a lot of flex.
So.
emily-sander_1_02-11-2025_12 (12:46):
It does.
And like you said, it's not foreveryone, which is not like a
judgment call at all.
It's just, you know, know yourstrengths.
And, you know, I, I alwaysthought of myself as like,
Porpoising in and out of likethe tactical and practical and
up altitude and down altitudeand all these things.
Uh, and I, I love that.
I love
andrew-kisslo_1_02-11-202 (13:01):
Yeah,
emily-sander_1_02-11-2025 (13:01):
about so many different areas of the
business, but if there areplenty of people that you need
to sit and be like a subjectmatter expert.
In this one area and just belike a technical expert.
And like, you need those folkson your team and throughout your
company as well.
Um, but just know if you'regoing for a chief of staff role,
you're probably going to bedoing this.
You're probably going to begoing up and down quite a bit.
(13:22):
And I, I love the, um, thequadrant accesses you mentioned,
what's like breadth and depth.
And then, you know, is this anew company, kind of a startup
vibe or more of a establishedmature company?
So much different versions ofchiefs of staff.
Um, With regard to yourprincipal, what's something that
(13:43):
you appreciated about her?
andrew-kisslo_1_02-11-202 (13:47):
yeah, I think, you know, 1 of there's
a, there's a couple of thingsthat I appreciated about her
specifically.
1 was, I really got a, a, amaster's course, um, in
authentic leadership that, um,that there are many leaders and
I found we probably all knowthat you work with some or that
you've worked around some, whichare.
Um, the leader who they are inthe room with other people is
(14:08):
not who they are outside of theroom.
They, they shift into a gear.
Um, and those gears canultimately, the more people
aren't fools, um, you know, andpeople, the more that they work
with executives, they can kindof see.
Wait a minute, this, thisexecutive isn't being authentic.
They're not who they perceive tobe for the better or the worse.
Um, and, you know, the, theleader that I worked for was
(14:31):
incredibly authentic, incrediblyapproachable, consistent to the
team.
It did not matter whether wewere in the room with interns
who just graduated from collegeto she was in a room in front of
the board of directors ormeeting a president of a
country.
Same person, same delivery.
And that authenticity, um,really is a great lesson that
(14:52):
you can only be who you are.
And in order for people to, um,people are really attracted to
leaders who are that authentic.
Um, and so I think that was likethe most, the most primitive
lesson I got was, you know, Um,just leading from authenticity,
um, and, and that can neversteer anyone wrong, to be
honest, um, that was, that wasone, I think the other thing at
(15:13):
the other end of the continuumthat I got, which is a really
great lesson, which was, um, is,um, I call it rebel leadership,
um, but she was a leader who hadno problem constantly pressure
testing and pushing.
Um, and she was a change agentstill is.
Um, and so one of the thingsthat she gave me as a lesson one
(15:34):
time was, um, she said, youknow, if you're going to be a
change agent, um, what thatmeans is you're signing up for a
life of resistance.
No one wants to be disrupted.
Um, but when you are a changeagent and you're going around
and you're pushing on things,you're doing it because you
believe that there is a betterway, um, that can help the
company.
And so that really sometimesmeets a lot of resistance.
(15:56):
Um, and so being a change agentreally is the only lever you
have is pressure.
How much pressure would alwaysdo this?
How much pressure can you bringto any given situation?
Um, and when it's just enough,Where people start to push back
so heavily, you're like, okay,that's a little bit too much,
but you bring it again.
Um, and it's that constant, um,desire to just challenge the
(16:19):
status quo in a, in a verythoughtful, deliberate and
intentional way, not justyelling at people.
It was always very strategic andwell thought out.
Um, but when she saw somethingthat, um, could be better attack
it, um, and bring people along.
And, and the, the final lessonof that was, um, I would always
(16:40):
ask her, like, you know, itfeels kind of isolating when
you're a leader and you'repushing and you're challenging
because you can stand out andshe would say, yeah, you know,
but that's my job.
That's why I'm here.
That's what they're paying me todo.
And she would say, I knowexactly when my job is done and
say, okay, what's the recipe?
And she would say, I know my jobis done as a change agent when
(17:03):
someone else in the room sayswhat I was saying, and I would
say, okay, why that?
And she goes, because now it'salive in the world with someone
else to take care of.
And it was really a Zen kind ofapproach to say, you're on your
own and you're carrying a flag.
And then the minute someone elsecarries the flag with you, and
they're like, yeah, let's gocharge the hill now.
(17:25):
Change is actually happening.
And there's someone else alongfor the ride, and then it
multiplies from there.
And when I look back in thepatterns of all the things that
we worked on, and that she wasdriving, it was such a pattern.
It was always her alone as avoice.
Then getting someone to be like,yeah, I agree with what you're
saying.
And then they would startspeaking up and she would be
(17:47):
like, there it is.
And she would then focus onsomething else.
And so it was this constantplant to seed, water it, and
then have someone else tend toit.
And then you're off to the nextthing.
Um, so yeah, I think those were,those were the big lessons that
I got, I think at a macro level,um, from a really phenomenal
leader.
emily-sander_1_02-11-2025 (18:05):
Thank you.
Yeah.
She does sound like a phenomenallittle leader.
So, can you talk us through andhow you moved out of the chief
of staff role?
And then maybe, you know, a yearor two after you were out of
that role and you werereflecting back your experience
as chief of staff, because as weall kind of put some distance
between things, we can take abreath and just have a different
(18:26):
perspective on things.
And what were some of thelessons that you took after the
fact?
andrew-kisslo_1_02-11-202 (18:30):
Well, you know, I kind of go to when
you're, when you're in, whenyou're in the job, there is no
perfect time to do them as inhow long you do them.
You can have an incrediblyintense one year of rotation,
and it's time.
Some people do them for a verylong time.
I did it for four years.
Um, and so I kind of had beenaround the sun, as I like to
say.
A second time, a third time, afourth time.
And I began to see the patternswhere I'm sure that fifth year
(18:52):
would have been phenomenal.
But for me, I had done my 10,000 hours in understanding
leadership, understandingculture and those types of
things.
So I knew for me, it was time.
Um, and there is an element whenyou're in the job because you
are back to porpoising and doingthese parabolas.
Your job is so different thanyour peers and you have this
(19:14):
existential fear of like, doesanyone know what I do?
I don't even know what I doanymore.
I'm an expert in everything yet.
Nothing.
Do I have transferable skills?
Like it, it can come to a pointwhere you're like, I'm kind of
feel like a carton of milk.
Like I've been out of the,Civilian life of a normal job.
How do I re enter the workforce?
Um, and so, you know, that is anatural thing, I think, for any
(19:37):
chief of staff.
Um, for me, it came to the pointwhere I had a recognition of,
okay, it's time.
And I needed to also make spacefor someone else to to take and
breathe life into the job intheir own way.
Um, and so, um.
You know, as I was thinkingabout it, I was very deliberate
with my leader to say, I thinkit's time.
Um, and with with her backing togo explore areas that were of
(20:01):
interest and just haveconversations.
Um, and ultimately, um, I, Itook a job, um, after it, that
was part of a very good career,uh, conversation that I had, um,
not only with her, but withother leaders, which was, you
know, Um, it dawned on me verylate in my career that maybe I
actually could, could do thingsthat was great at achieve a
(20:23):
staff, um, role at, which arereally things like a chief
operating officer.
Um, and so I asked her, I thinkI want to be a CEO after this
job.
Um, she said, I don't knowanything about that.
Um, go talk to CEOs.
And that's okay.
So best career advice ever got,um, someone said, Hey, when I
(20:45):
did that, somebody challengedme, go meet 30 of these people
in 30 days.
I was like, that's a crazy idea,but I did it.
And I reached out to somebodythat was a COO who then
introduced me to another COO.
And I went through this speeddating course of COOs.
And I think I got to 25 and like35 days.
Um, Of companies of all sizes.
(21:06):
Um, and what I got was reallygreat feedback from them of.
Um, here's your, with yourbackground, here's what we
recommend where you fill in, um,skills and capabilities to go
become a COO of a very specifickind, change agent COO.
Um, and with that, they said theone thing with your background,
(21:29):
um, that you just need to show,because you've done marketing,
you've done sales, you've donekind of everything.
And with a chief of staff job,awesome.
You need to prove that you canmove a P& L.
I was like, okay.
emily-sander_1_02-11-2025_ (21:40):
Hmm.
andrew-kisslo_1_02-11-2025_1 (21:40):
So the job that I found after that
was, um, designed where I talkedto the CMO of Microsoft.
Um, and he said, Hey, you shouldtake this job because that will
give you P and L.
And I said, wow.
Okay.
Wow.
So I took a job that was reallythat category killer for me to
fill out a P and L capability.
(22:02):
Um, and long story short, I didthat for a while, um, before
ultimately, um, Finding the rolethat I have now at SAP, um,
which still is a feeder type ofrole into COO jobs.
Um, and so, you know, at the endof the day, your company doesn't
own your career, you do, and youreally have to put the thought
into Um, self scouting and whereyou weak and where you strong
(22:26):
and then try to stitch togetherexperiences that fill in, um,
the things that you're going toneed.
Ultimately, at some point in thefuture,
emily-sander_1_02-11-2025_1 (22:35):
And I just want to highlight what
you just said.
So the fact that you took, tookmassive action, you know, 25
people in 35 days, that's nosmall feat.
And you got feedback and youask, you know, know, where do
you see my strengths?
Where do you see my gaps?
You know, what would yourrecommendation be?
Kind of what's your outsideperception, not putting too much
weight on other people'sperception, but also you're in
(22:57):
the role that I want to be inand you're successful.
Like, help me, help me learnsome lessons to get there.
And then you're putting these,these different roles in place.
So I love that.
I just want to highlight
andrew-kisslo_1_02-11-2025 (23:06):
it's
emily-sander_1_02-11-2025_12 (23:07):
to hear again.
andrew-kisslo_1_02-11-2025_1 (23:07):
it is a, um, it was a wacky thing.
And I found, um, there werealways always 30 minute phone
calls and there's somethingabout asking friends and family
and people that you trust aboutcareer guidance because they
know you very closely.
Um, yeah.
But there is an element therewhere there is implicit bias
because they know you so well.
Um, and so, um, by findingpeople that had a job I thought
(23:28):
I wanted, um, it was always aninteresting 30 minutes.
It was always 15 minutes and 15minutes.
The first 15 minutes, I wouldask them, um, how did you get
the job?
Now that you have the job, Whatis the one job you wish you had
that would have prepared youbetter for the job now?
And it was always fascinating toget their take on that.
(23:49):
And then about minute 16, um, Iwould transition and I would
say, okay, you now know me 16minutes because most of these
people didn't know.
And I would say, here I am onpaper.
What do you think?
How do I come across?
What do I look like?
And so it was, it was, um, anabsolute clinic in how you
present yourself, how you showup, not only on paper, but in
(24:10):
person.
Um, And in those 15 minutes, youknow, they would give you a very
quick, um, assessment ofyourself.
Um, that was raw.
It was really good because itwas raw.
Um, and with that, with thosetwo 15 minute sessions, you
began to see the patterns overtime of how many of them
(24:31):
actually would say the samethings of jobs they wish they
had or the feeder kinds ofroles.
And then how many of themactually clued in on unbeknownst
to each other.
You need to go get PNL, you needto go get X.
And so it was a really, uh,fascinating.
I do think it was like the bestspeed dating on career I've ever
done.
It was hard.
I mean, asking people for timethat you do not know they're in
(24:54):
very lofty positions, um, was adifficult thing, but it ended up
being this sort of daisy chainof, well, I know a person go
talk to them.
And it ended up kind ofhappening.
Um, but a really great thing, nomatter what career you have.
Wacky idea, but best thing everdid.
emily-sander_1_02-11-2025 (25:10):
Yeah.
Love it.
Thank you for sharing thatstory.
I love it.
right.
So taking us to the next phaseof the life cycle here.
Um, when, when did you go, Oh, Ineed a chief of staff or how
andrew-kisslo_1_02-11-202 (25:20):
Yeah.
emily-sander_1_02-11-2025_1 (25:20):
how did the rec come about for like,
okay, now I'm looking for achief of staff.
andrew-kisslo_1_02-11-2025_1 (25:24):
So ultimately, um, you know, I
think once once I left the job,um, there is also that
transition of, um, even before Ineeded 1, um, I was a different
leader when I returns tocivilian life.
And it didn't dawn on me until Iwas no longer in the job.
Everything I had learned whenyou're in the job, you don't
(25:45):
know.
I'm doing budget.
I'm doing this.
Oh, my gosh.
It's a race.
It's a race.
It's a race.
Um, and then you leave it andthen you're in whatever your new
job is.
Um, and you're, you're, you'returning back to the home front.
Um, You start doing thingsnaturally and you kind of don't
know where they're coming from.
Your confidence in a room ofexecutives, you're just, you're
(26:06):
just doing things.
You're like, and people would belike, you just seem at ease.
I'm like, I don't know.
This just seems easy.
I'm not afraid.
Um, oh, you seem to be verydecisive and see strategy.
I don't know how I'm doing this,you know?
But when I look back, it wasbecause Of everything that I saw
and absorbed, and it wasn'tuntil I was out of it that I got
to draw upon it.
(26:27):
Um, so I would tell people ifyou do achieve a staff job, the
ROI is after not during.
Um, that's a key thing becauseit.
When you're in it, you just gotto get through it and just take
that risk that it will pay offfor me.
It did.
Um, you know, there became thenwhen I in my new role, um, of
(26:48):
why a chief of staff and why doI need one?
Um, you know, for the role thatI have at S.
A.
P.
Um, it's very complex, veryglobal in nature.
It has a lot of the elements ofwhat we're trying to do and
transform our own business,which are driving cloud and
culture.
Driving different, uh,commercial models that are
short, medium and long term.
(27:09):
So it started to fit the patternof for my own world in my own
different zip code.
Um, wow, this feels incrediblyfamiliar and it would be really
great, um, to have someone in arole that I can lean on, um, To
help me advance all those areas,um, as an executive, you just
can't do it all yourself.
Um, and sometimes you can't relyon your entire leadership team
(27:30):
to do it.
They have their own day jobs.
Um, and so asking a leader, um,who has a team of their own to
help you drive culture for theold org.
That's not fair.
Um, and so you end up having,you know, at some point the need
for.
This kind of a role to emerge.
Um, and so for me, it did.
And so, um, yeah, I, I, sincewe've last chatted, I found a
(27:50):
chief of staff.
Um, the job was,
emily-sander_1_02-11-2025_1 (27:52):
All
andrew-kisslo_1_02-11-202 (27:52):
yeah, and I, and I found someone
incredible.
Um, and she's on day 10, Ithink, probably
emily-sander_1_02-11-2025_1 (27:58):
Oh, wow.
andrew-kisslo_1_02-11-202 (27:59):
right now, um, but, um, You know, I
think the thing that in myselection, there was, I looked
at all different kinds of, um,of people and candidates and
the, the person that I, youknow, ended up picking, um, had
the 1 thing that is, um, youcan't teach and it was, um,
(28:21):
somebody that was coming intothe role with the, whatever,
whatever it takes and I don'tmean that in a, in a, in a trite
way, meaning like, um, I'm justhere to do what you tell me.
It was much more like.
I am here at the service ofmaking you and the org awesome,
and I am openly coming into therole knowing this isn't about
(28:44):
me.
It's about us, and for someoneto lead with that maturity right
out, you just kind of know theyget it.
They just get that that is thedown payment that you kind of
have to make where you suppressyour own ego for a while.
Because it's not about you.
It is about the org.
It is about the team and theleader, um, which means you are
(29:08):
in the shadows.
You are off and out of frame.
Um, your goal isn't to be inframe and be the hero.
That's not what a chief of staffis.
There are times where that iscalled for, but that's not the
job.
Um, And so, um, yeah, I'm, I'mthrilled with the choice.
She's going to be incredible.
Um, so, uh, I'm really excitedto, to watch her grow.
emily-sander_1_02-11-2025_1 (29:29):
And just what is the experience like
10 days in of being like theprincipal now?
Because you've been the chief of
andrew-kisslo_1_02-11-2025 (29:33):
It's weird.
emily-sander_1_02-11-2025_1 (29:34):
Oh, I'm actually, yeah.
andrew-kisslo_1_02-11-2025_12 (29:36):
I think, you know, my own lesson
is, um, you know, and she willbe my, my second chief of staff
is.
Um, you know, reflecting backhaving been 1 is, um, um, the,
my 1st chief of staff, um, wasshe had never been 1 and I was
like, oh, don't worry.
I've done it.
I can tell you all the things todo.
And here are all my oldplaybooks and all the things
that I can realize inretrospect, um, as helpful as
(29:58):
that was to help her ramp veryquickly.
I actually robbed her of all theexperience to come up with it on
our own.
And I was just like, Oh, don'tworry.
I'll just give you this stuff,which I can see how having been
one and being then a leader,there is an influence of power
there where, Oh, you're themanager and you kind of were
one.
So I'll just do what you said.
I was the chief of staff for atotally different company,
(30:20):
different leader.
And so for me to effectivelytake a playbook and say, just
run this, it stifled that.
Um, and so my 2nd time aroundwith the 2nd chief of staff, um,
is almost the opposite.
I'm like, if you need help, Ihave ideas.
Otherwise, I trust you.
Like, I'm listening to you.
Like, whatever you think youwant to do, let's go.
(30:42):
Um, and so trying to open up alittle bit more space and
freedom.
I certainly have opinions, um,but less more, um, run the book
and much more like, let's Youknow, let's paint this together
type of thing
emily-sander_1_02-11-2025 (30:55):
Yeah, for sure.
I think there's certainly likecommon threads, threads and
foundational pieces that wouldhelp pretty much any chief of
staff, but you have to help themwith their own playbook for like
their specific role, theirspecific principle in their
specific situation.
And that playbook is going tochange over time, even within
one role.
andrew-kisslo_1_02-11-2025_ (31:12):
all the time,
emily-sander_1_02-11-2025_1 (31:13):
So,
andrew-kisslo_1_02-11-2025 (31:13):
goes back to the chief of staff jobs.
Um, they are all very similar,you know, and we kind of talked
about this earlier.
There are shared traits of like,every chief of staff probably
has to deal with budget and hasto deal with some level of
culture.
Um, but it kind of stops there.
Everything else is as unique asthe leader.
You know, a leader can be on abusiness that's rising or dying.
(31:35):
A leader can be falling in favorout of favor.
A leader can have a big team,small team.
Um, and when you start throwingin all these variables, the job
starts morphing into somethingtotally different.
Um, and you can be in a roomwith a bunch of chiefs of staff.
And they get the, there's anunwritten language that everyone
kind of gets because you allkind of know what it is, how you
(31:57):
are doing your job at the end ofthe day, maybe so different
where you're like, wait, you dothat for your leader.
And you're like, yeah, do younot do that?
Oh, my leader doesn't want me todo that.
You know, and you end up going,oh, that's really different.
Um, you do budget, right?
Oh, yeah, do budget.
Um, you know, there are sharedcommon experiences.
Um, yeah.
But they are really unique.
That's why finding a chief ofstaff, um, is as hard as being
(32:20):
one because it is about thematch between a leader and a
chief of staff.
You know, you have to find theright person, but you have to be
the right person, um, becausethat is a really intense,
intimate, trusting relationshipthat you just can't plug and
play.
I mean, you have to find thatmatch.
Um, so they're, they're, they'repretty unique in that, in that
(32:41):
regard.
emily-sander_1_02-11-2025 (32:43):
yeah.
you for that.
As we wind down here, you and Ihave talked about, you, you
brought up this, um, greatanalogy in a previous
conversation we had about a, aco driver in a rally
andrew-kisslo_1_02-11-202 (32:52):
Yeah.
emily-sander_1_02-11-2025_1 (32:52):
And I just wanted you to share that
with you because it was so, sogood.
andrew-kisslo_1_02-11-202 (32:55):
Yeah.
emily-sander_1_02-11-2025_1 (32:55):
can you share that
andrew-kisslo_1_02-11-202 (32:56):
Yeah.
So I'll give you the background.
So a rally car driving, which iscertainly very popular in Europe
and other parts of the world.
Um, it's where cars go down dirtroads, usually incredibly fast.
Um, and there's always 2 peoplein the car, um, and there's a
driver and they actually callthem a co driver or a copilot.
Um, and, um, what that persondoes is they have a book in
(33:19):
front of them, And a microphone,um, and they are effectively
calling the plays for the driverand, um, the plays are we're
about to turn a 100 meters ditchjump all the things that are
predicting what's coming.
Um, and so I have a friend whodoes this and 1 weekend said,
hey, I, I've lost my co driverson vacation.
(33:41):
Do you want to do this for me?
And I was like.
Sure, I'm pretty crazy.
Um, here in the state ofWashington, we drove out into
the middle of old forest roadsand we jumped in his Subaru
rally car and had stickers andall the kinds of things and we
start hauling down the road like100 miles an hour on dirt roads,
trees whizzing past.
Um, and he was just sort ofwarming up the car.
(34:03):
Um, and he gave me a lesson, youknow, before we went to say, you
need to learn this language.
And I learned the language of.
Mhm.
Overcrest, right?
100 meters, blah, blah, blah.
And when we got there, I said,why do you need me?
You are driving very fast.
You kind of know what you'redoing.
And he said, no, no, no, youneed to understand.
(34:24):
I'm driving by what you'retelling me, not by what I'm
seeing.
And I was like, oh, really?
He's like, yeah, I'm, I'mreacting in the moment.
And so when you tell mesomething's coming over the
hill, and I now need to prepareto turn because we're going 100
miles an hour, you're helping meprepare.
And I always look back on thatas such a great metaphor of
(34:46):
chief of staff and leader wherea leader is acting in the moment
all the time and having someonethat is in the cockpit that
knows everything about fuel inthe car, speed of the car,
what's coming, you are callingthe plays.
Thanks.
And the driver or the leader candecide to not listen, but in so
many ways when it's humming andwhen it is working, it is in
(35:07):
concert of preparing and you'rejust in that dialogue actively
going back and forth of theleader is driving by what you're
telling them, not by whatthey're seeing and their gut is
coming forward.
But anyway, that was that wasthe analogy or metaphor we used
and it's just always worked forme because I think, um, it's
such a such a fascinating thingthat those 2 roles can do
(35:29):
together.
Um, that certainly applies.
I think in this kind of in thiskind of setting.
emily-sander_1_02-11-2025_124 (35:34):
I love that one.
It stuck with me.
So thank you for, for recountingit
andrew-kisslo_1_02-11-202 (35:37):
Yeah,
emily-sander_1_02-11-2025_1 (35:37):
But Andrew, you shared so much and
it's been, it's been great to,to talk with you again.
And, um, thank you very much fortaking the time and being on the
show.
Appreciate it.
andrew-kisslo_1_02-11-202 (35:46):
thank you so much for for this.
Um, and anytime, you know, Ithink we had joked also, there's
a saying amongst chief of staff,which is, you have to be smart
enough to do it dumb enough totake it, which is they are
phenomenal roles.
And I can say anyone that.
Finds an opportunity to do it.
Um, take it, you will not regretit.
Um, you know, there is lifebefore chief of staff and after
(36:06):
chief of staff.
And at least for me, it paid offin so many dividends of personal
growth and career growth, um,that it's, uh, for me was one of
the most important things I didin my career.
emily-sander_1_02-11 (36:17):
Beautiful.
We'll leave it there.
Thanks again,
andrew-kisslo_1_02-11-20 (36:19):
Thanks so much for the time.
See you.
My guest today is Andrew Kislow,
and he and I first connectedbecause he was, um, recruiting
and hiring a chief of staff forhis, his team.
And, uh, he has been in thechief of staff role at his 10
plus years at Microsoft.
It was one of one of the manyroles you've held there.
Um, and so we're gonna talkabout the lifecycle of chief of
(00:47):
staff, and Andrew is wellpositioned to do that.
So, Andrew, welcome to the show.
Thank you so much for beinghere.
andrew-kisslo_1_02-11-20 (00:52):
Thanks for having me.
It's a pleasure.
It's a great topic.
I love talking about this.
So,
emily-sander_1_02-11-2025_1 (00:56):
One of my favorite too.
So just to give our listenersquick background and context,
can you just give us somebackground for, for you and your
career up to the point where yougot to be chief of staff?
andrew-kisslo_1_02-11-202 (01:07):
yeah, absolutely.
Um, currently, I'm the seniorvice president of global partner
marketing at S.
A.
P.
Um, but when I go in the wayback machine, um, before I
became a chief of staff andeverything up to that, um, I
started my career after businessschool, um, at a small startup,
um, In the dot com era, wheneverything was going to take
over the world, um, and itprogressed, um, ultimately
(01:28):
leading to a job at Microsoft,um, and had done a variety of
roles at Microsoft, everythingfrom product marketing, product
management, um, and chief ofstaff or, um.
You know, staff positions wasalways something that interested
me.
Um, and so there came a point inmy career where I found the
right opportunity at the righttime to do that.
But most of my background was inmarketing, uh, and dealing with
(01:50):
customers.
So.
emily-sander_1_02-11-20 (01:52):
Gotcha.
Thank you.
So can you just touch on alittle bit of like what you
thought about when you firstheard chief of staff, what you,
what that decision process waslike going into that role, that
whole phase of
andrew-kisslo_1_02-11-202 (02:03):
Yeah, you know, I, I kind of go back
to, um, even the history of theroles, because my first
introduction to someone that wasa chief of staff, um, you know,
chief of staff positions haveexisted probably since, um,
originally the, the, you know,as old as the military in the
Roman days, there was alwayssomeone and we've always seen,
you know, in TV shows, someonethat was the right hand in
either the mafia or even Game ofThrones, right?
(02:24):
Um,
emily-sander_1_02-11-2025 (02:25):
Yeah.
andrew-kisslo_1_02-11-2025_1 (02:25):
in tech, they actually were born
out of the origin, um, early onwhere they were called technical
assistance.
T.
A.
S.
Um, and when you really thinkback to the, um, the birth of
these tech companies, um, thatusually in a founder culture,
Microsoft Intel, uh, theyusually had someone that had to
support the founder that was thechief executive and they were
(02:47):
typically T.
A.
S.
Technical assistance.
Um, and what those folks didwas, um, Serve as a right hand
person to help everything withdemos on stage, um, to technical
directions of the product.
Um, and so my first introductionto someone that was a TA, um,
was actually in my first roleafter business school.
And the person had been a TA forCraig Barrett, who was the CEO
(03:11):
of Intel, followed Andy Grove,um, and so, um, he was
effectively a mentor for me veryearly in my career.
And I was not technical, but Ireally loved his approach to how
he, um, looked at everything inthe business.
And I was always curious, like,how do you know to look at the
business this way?
And he was like, oh, I was a TAfor a CEO.
(03:31):
And I was like, what's a TA?
And he really educated on me andstarted to open up my world of
these special, unique roles thathelp executives scale.
Um, and so that was my firstintroduction very early on.
Um, when I left and joinedMicrosoft, um, Uh, I also, um, I
remember the day I was in aroom, I was a junior person, way
(03:52):
in the back of the room, veryimportant people, um, in the
center of the room, um, and thisyoung, lovely woman walked in
and she started barking commandsto everyone.
And she was like, oh, you'refull of shit.
And oh, the numbers are wrong.
And what are you guys going todo about this?
And she walked out and I said,who was that?
And they were like, oh, that'sso and so's chief of staff.
(04:13):
And I was like, wow, like, howdid that person come in and
command a room and knoweverything about the business?
And effectively was there to notonly force multiply, but to keep
the business on track and itplanted yet another seed in me
of like, wow, that seems like areally, really unique job.
(04:33):
Um, so I was introduced veryearly on to 2 very specific
people who held that position intotally different ways.
But it piqued my interest.
emily-sander_1_02-11-2025 (04:43):
Yeah.
And it sounds like the, thethrough line of that is just you
going, they see the wholebusiness across the board
holistically.
Like how did they do that?
And that's what got, got yourattention among other things.
So us to the point where it'slike now you're being offered
chief of staff and kind of whoyour principal was and did you
know this person before and howyou interacted and set up that
(05:03):
role in relationship.
Tell us all about that.
andrew-kisslo_1_02-11-202 (05:05):
Yeah, I think, you know, in the
journey of, um, I thought Iwanted to be one.
Um, and I got advice early onfrom someone, um, who had been
chief of staff, um, very similarto maybe a listener today of
their thinking about it.
And the guidance I got early onwas, um, these jobs aren't for
everyone.
And the key thing is before youeven entertain it, um, you have
(05:26):
to know why you're going afterit.
Um, or is this illusion of.
There are super cool jobs, andyou're gonna fly on jets, and
you're gonna be in the coolestmeetings in the world.
Um, and while some of thosethings may be true every now and
then, um, that's not the job.
Um, and so you really have to goin with eyes wide open.
Um, so I did the work, uh,before I even found a job to,
(05:48):
uh, apply to, which was, um, Iknew in my career at that time,
I wanted an experience where Iwould learn how a leader thinks.
How a leader leads.
Um, and there are a couple ofthings that come along with
that.
How leaders drive culture atscale.
Um, how leaders make decisionsin the present for things that
(06:08):
are short, medium, and longterm.
So that's like decision making.
Um, and then there's, you know,the, the other part, which isn't
the fun part, but it's sofundamental for any leader is,
uh, business excellence.
How do you manage the resourcesand headcount and money that you
bring to bear, uh, to drivereally important outcomes and
really achieve a staff.
(06:29):
Fundamentally touches all thosethings.
They help culture.
They help the bottom line andbudgets and resources and
strategy.
And then they also help in themiddle rallying all the
capabilities of horizon zero allthe way to horizon three of
things that aren't that are, youknow, a glimmer in someone's
eye, but they're not here yet.
And you have to hold space forall of that.
(06:50):
Um, so that's what I knew Iwanted to get out of it.
Um, yeah.
And so I found an opening, um,for someone, um, it was in the,
in the Azure marketing world atMicrosoft.
And this was early in the daysof cloud.
We didn't really have an idea ofwhat we wanted to be.
Um, and I applied for the joband the leader said, Hey, you're
perfect.
I know you, you, you sort of cando all these things just enough,
(07:13):
um, try the job.
If you hate it, we'll findsomething else.
And I was like, what could gowrong with a pitch like that?
Um, and I did it for four years.
Um.
And it was a rocket ship.
It was really, um, I caughtlightning in a bottle in a
couple of different ways where Iworked for a leader who was a
phenomenal person and leader onculture and strategy.
(07:34):
And also for a business that wasexploding, we used to commonly
joke of we were doing thingsthat they cannot teach you in
business school.
There is no business schoolclass or professor ever.
That knows how to take a billionin revenue and double it and
double it and double it.
Um, and just having exponentialgrowth, um, while not having
(07:56):
more resources.
This is key.
We were exploding the cloudbusiness.
Um, but we were not getting moreheadcount and we really weren't
getting that much more budget.
And so how do you extract astrategy that drives that much
yield?
Um, Is it was, it was a, aninteresting ride for sure.
Um, lots of very new businessmodels and things that we
(08:18):
experimented to.
Um, but, uh, that, that wasultimately, you know, the
position that I found that I wasincredibly lucky, um, to be
honest, to find that, you know,at that time,
emily-sander_1_02-11-2025_ (08:30):
Wow.
That's amazing.
And can you just talk about, itsounds like so much was
happening so quickly in thosefour years.
And I'm assuming you tell methings were evolving at a rapid
clip.
So your chief of staff role wasevolving as you moved along.
Your principal's role wasevolving as theirs moved along.
Can you just talk about kind ofhow you progressed and, um, you
(08:51):
know, when I was chief of staff,you would have to like be in it
and like go in it and you're inkind of tunnel vision and then
you would take a breath and zoomout and go like, where are we?
What's happening?
What's the long term?
Um, and then go back in it inthe short term.
So kind of tell me a little bitabout your experience in those
four
andrew-kisslo_1_02-11-202 (09:05):
yeah, you know, I think, I think, um,
in the four years, you know, Ikind of look back and, um, um,
Every year I did it, um, therewas something different
happening in the business,right.
And at least in tacking thepace, it was.
You break down your businesskind of almost into 90 day ship
windows.
Every 90 days you're shippingsomething and that's you're
moving fast, but the externalenvironment around you is moving
(09:26):
faster.
Um, and so, um, every time thatyou put a plan out there, you
hope and pray that somethingdoesn't happen externally where
you have not to change it.
Um, and that never holds, right?
And so, um, you're constantly inthe, in the business, like you
mentioned, where, um, you'redeep in the weeds and you're
planning, uh, and then yousurface for air and you're
(09:46):
raising altitude and then youpressure drop again.
And so this, This constantparabolas, I would say of
altitude that you're in thebusiness, um, of do we have the
right strategy?
I think we've got a vision andthen you're like, like, execute
and then you pop up and you'relike, oh, my gosh, it's not
working or something differenthappened.
And you're constantly doing, um.
This, um, that's why in someways it's, it's not for
(10:08):
everybody.
It is hard.
Um, and you have to hold yourleader in the highest regard
because your job is to make yourleader and your org as awesome
as possible yet behind thescenes.
It can sometimes be utter chaoswhere you don't want.
Um, a lot of that, uh, tumult orindecision to come forward, um,
(10:29):
which is natural in anybusiness.
It's naturally in any singlebusiness.
Um, but, you know, it, itrequires different archetypes of
chiefs of staff to kind of, youknow, Come forward as well, um,
at least in some of the researchthat we did, um, when I was in
the role at Microsoft, and Ithink they're fair is there's
sort of 4 archetypes of chiefsof staff.
Um, and someone needs to flowthrough all of them, or you kind
(10:51):
of find your place.
Um, and at least in a 2 by 2,what we found was, um.
There's one thing on the Y axis,which is, um, is, um, is your
leader needing a lot of depth?
Or are they a breadth leader?
Like, are they really specificand an engineering leader or are
they kind of common?
That's one axis.
Um, the X axis is, is this anentirely new business or is this
(11:14):
an old established business?
And what we found was that witha couple of questions, it really
led to four kinds of archetypes.
Um, you have chiefs of staffthat are fixers, And they go
around and they fix stuff.
Um, you have chiefs of staffthat are Jack or Jill of all
trades and they kind of need tofloat.
And those would usually be insomebody that's a new business
(11:35):
with a lots of breath.
They're just everywhere.
They're firefighting.
Um, in that upper right.
Um, you would have someonethat's a force multiplier.
Um, and the role of a forcemultiplier is very different
than a Jack and Jill of alltrades.
They're in the opposite parts ofthe quadrant.
Um, and then the final one isring master.
bringing everybody together andkind of driving and being an
(11:55):
emcee.
Um, and I think that in my fouryears, I floated through all of
those modes based on the, onthe, on the business.
And sometimes it was seasonal.
Sometimes it was like year one,I was just a fixer.
I had no idea what to do.
And then I was like, I think Igot this.
I'm now a Jack and Jill of alltrades.
Cause I can kind of see it.
And then you can kind of see,Oh, now I'm maturing.
(12:16):
Um, um, but archetypes werereally helpful for me to
understand.
Um, because the job is thatnebulous.
It's a living, breathing thing.
Um, and so I think for peoplewho come into the job, um, with
the expectation of my job isvery codified and it's the same,
not this kind of job.
Um, you really need to almost beokay with, um, that wide
(12:39):
aperture.
That's kind of constantly movingin and out, um, because it
requires a lot of flex.
So.
emily-sander_1_02-11-2025_12 (12:46):
It does.
And like you said, it's not foreveryone, which is not like a
judgment call at all.
It's just, you know, know yourstrengths.
And, you know, I, I alwaysthought of myself as like,
Porpoising in and out of likethe tactical and practical and
up altitude and down altitudeand all these things.
Uh, and I, I love that.
I love
andrew-kisslo_1_02-11-202 (13:01):
Yeah,
emily-sander_1_02-11-2025 (13:01):
about so many different areas of the
business, but if there areplenty of people that you need
to sit and be like a subjectmatter expert.
In this one area and just belike a technical expert.
And like, you need those folkson your team and throughout your
company as well.
Um, but just know if you'regoing for a chief of staff role,
you're probably going to bedoing this.
You're probably going to begoing up and down quite a bit.
(13:22):
And I, I love the, um, thequadrant accesses you mentioned,
what's like breadth and depth.
And then, you know, is this anew company, kind of a startup
vibe or more of a establishedmature company?
So much different versions ofchiefs of staff.
Um, With regard to yourprincipal, what's something that
(13:43):
you appreciated about her?
andrew-kisslo_1_02-11-202 (13:47):
yeah, I think, you know, 1 of there's
a, there's a couple of thingsthat I appreciated about her
specifically.
1 was, I really got a, a, amaster's course, um, in
authentic leadership that, um,that there are many leaders and
I found we probably all knowthat you work with some or that
you've worked around some, whichare.
Um, the leader who they are inthe room with other people is
(14:08):
not who they are outside of theroom.
They, they shift into a gear.
Um, and those gears canultimately, the more people
aren't fools, um, you know, andpeople, the more that they work
with executives, they can kindof see.
Wait a minute, this, thisexecutive isn't being authentic.
They're not who they perceive tobe for the better or the worse.
Um, and, you know, the, theleader that I worked for was
(14:31):
incredibly authentic, incrediblyapproachable, consistent to the
team.
It did not matter whether wewere in the room with interns
who just graduated from collegeto she was in a room in front of
the board of directors ormeeting a president of a
country.
Same person, same delivery.
And that authenticity, um,really is a great lesson that
(14:52):
you can only be who you are.
And in order for people to, um,people are really attracted to
leaders who are that authentic.
Um, and so I think that was likethe most, the most primitive
lesson I got was, you know, Um,just leading from authenticity,
um, and, and that can neversteer anyone wrong, to be
honest, um, that was, that wasone, I think the other thing at
(15:13):
the other end of the continuumthat I got, which is a really
great lesson, which was, um, is,um, I call it rebel leadership,
um, but she was a leader who hadno problem constantly pressure
testing and pushing.
Um, and she was a change agentstill is.
Um, and so one of the thingsthat she gave me as a lesson one
(15:34):
time was, um, she said, youknow, if you're going to be a
change agent, um, what thatmeans is you're signing up for a
life of resistance.
No one wants to be disrupted.
Um, but when you are a changeagent and you're going around
and you're pushing on things,you're doing it because you
believe that there is a betterway, um, that can help the
company.
And so that really sometimesmeets a lot of resistance.
(15:56):
Um, and so being a change agentreally is the only lever you
have is pressure.
How much pressure would alwaysdo this?
How much pressure can you bringto any given situation?
Um, and when it's just enough,Where people start to push back
so heavily, you're like, okay,that's a little bit too much,
but you bring it again.
Um, and it's that constant, um,desire to just challenge the
(16:19):
status quo in a, in a verythoughtful, deliberate and
intentional way, not justyelling at people.
It was always very strategic andwell thought out.
Um, but when she saw somethingthat, um, could be better attack
it, um, and bring people along.
And, and the, the final lessonof that was, um, I would always
(16:40):
ask her, like, you know, itfeels kind of isolating when
you're a leader and you'repushing and you're challenging
because you can stand out andshe would say, yeah, you know,
but that's my job.
That's why I'm here.
That's what they're paying me todo.
And she would say, I knowexactly when my job is done and
say, okay, what's the recipe?
And she would say, I know my jobis done as a change agent when
(17:03):
someone else in the room sayswhat I was saying, and I would
say, okay, why that?
And she goes, because now it'salive in the world with someone
else to take care of.
And it was really a Zen kind ofapproach to say, you're on your
own and you're carrying a flag.
And then the minute someone elsecarries the flag with you, and
they're like, yeah, let's gocharge the hill now.
(17:25):
Change is actually happening.
And there's someone else alongfor the ride, and then it
multiplies from there.
And when I look back in thepatterns of all the things that
we worked on, and that she wasdriving, it was such a pattern.
It was always her alone as avoice.
Then getting someone to be like,yeah, I agree with what you're
saying.
And then they would startspeaking up and she would be
(17:47):
like, there it is.
And she would then focus onsomething else.
And so it was this constantplant to seed, water it, and
then have someone else tend toit.
And then you're off to the nextthing.
Um, so yeah, I think those were,those were the big lessons that
I got, I think at a macro level,um, from a really phenomenal
leader.
emily-sander_1_02-11-2025 (18:05):
Thank you.
Yeah.
She does sound like a phenomenallittle leader.
So, can you talk us through andhow you moved out of the chief
of staff role?
And then maybe, you know, a yearor two after you were out of
that role and you werereflecting back your experience
as chief of staff, because as weall kind of put some distance
between things, we can take abreath and just have a different
(18:26):
perspective on things.
And what were some of thelessons that you took after the
fact?
andrew-kisslo_1_02-11-202 (18:30):
Well, you know, I kind of go to when
you're, when you're in, whenyou're in the job, there is no
perfect time to do them as inhow long you do them.
You can have an incrediblyintense one year of rotation,
and it's time.
Some people do them for a verylong time.
I did it for four years.
Um, and so I kind of had beenaround the sun, as I like to
say.
A second time, a third time, afourth time.
And I began to see the patternswhere I'm sure that fifth year
(18:52):
would have been phenomenal.
But for me, I had done my 10,000 hours in understanding
leadership, understandingculture and those types of
things.
So I knew for me, it was time.
Um, and there is an element whenyou're in the job because you
are back to porpoising and doingthese parabolas.
Your job is so different thanyour peers and you have this
(19:14):
existential fear of like, doesanyone know what I do?
I don't even know what I doanymore.
I'm an expert in everything yet.
Nothing.
Do I have transferable skills?
Like it, it can come to a pointwhere you're like, I'm kind of
feel like a carton of milk.
Like I've been out of the,Civilian life of a normal job.
How do I re enter the workforce?
Um, and so, you know, that is anatural thing, I think, for any
(19:37):
chief of staff.
Um, for me, it came to the pointwhere I had a recognition of,
okay, it's time.
And I needed to also make spacefor someone else to to take and
breathe life into the job intheir own way.
Um, and so, um.
You know, as I was thinkingabout it, I was very deliberate
with my leader to say, I thinkit's time.
Um, and with with her backing togo explore areas that were of
(20:01):
interest and just haveconversations.
Um, and ultimately, um, I, Itook a job, um, after it, that
was part of a very good career,uh, conversation that I had, um,
not only with her, but withother leaders, which was, you
know, Um, it dawned on me verylate in my career that maybe I
actually could, could do thingsthat was great at achieve a
(20:23):
staff, um, role at, which arereally things like a chief
operating officer.
Um, and so I asked her, I thinkI want to be a CEO after this
job.
Um, she said, I don't knowanything about that.
Um, go talk to CEOs.
And that's okay.
So best career advice ever got,um, someone said, Hey, when I
(20:45):
did that, somebody challengedme, go meet 30 of these people
in 30 days.
I was like, that's a crazy idea,but I did it.
And I reached out to somebodythat was a COO who then
introduced me to another COO.
And I went through this speeddating course of COOs.
And I think I got to 25 and like35 days.
Um, Of companies of all sizes.
(21:06):
Um, and what I got was reallygreat feedback from them of.
Um, here's your, with yourbackground, here's what we
recommend where you fill in, um,skills and capabilities to go
become a COO of a very specifickind, change agent COO.
Um, and with that, they said theone thing with your background,
(21:29):
um, that you just need to show,because you've done marketing,
you've done sales, you've donekind of everything.
And with a chief of staff job,awesome.
You need to prove that you canmove a P& L.
I was like, okay.
emily-sander_1_02-11-2025_ (21:40):
Hmm.
andrew-kisslo_1_02-11-2025_1 (21:40):
So the job that I found after that
was, um, designed where I talkedto the CMO of Microsoft.
Um, and he said, Hey, you shouldtake this job because that will
give you P and L.
And I said, wow.
Okay.
Wow.
So I took a job that was reallythat category killer for me to
fill out a P and L capability.
(22:02):
Um, and long story short, I didthat for a while, um, before
ultimately, um, Finding the rolethat I have now at SAP, um,
which still is a feeder type ofrole into COO jobs.
Um, and so, you know, at the endof the day, your company doesn't
own your career, you do, and youreally have to put the thought
into Um, self scouting and whereyou weak and where you strong
(22:26):
and then try to stitch togetherexperiences that fill in, um,
the things that you're going toneed.
Ultimately, at some point in thefuture,
emily-sander_1_02-11-2025_1 (22:35):
And I just want to highlight what
you just said.
So the fact that you took, tookmassive action, you know, 25
people in 35 days, that's nosmall feat.
And you got feedback and youask, you know, know, where do
you see my strengths?
Where do you see my gaps?
You know, what would yourrecommendation be?
Kind of what's your outsideperception, not putting too much
weight on other people'sperception, but also you're in
(22:57):
the role that I want to be inand you're successful.
Like, help me, help me learnsome lessons to get there.
And then you're putting these,these different roles in place.
So I love that.
I just want to highlight
andrew-kisslo_1_02-11-2025 (23:06):
it's
emily-sander_1_02-11-2025_12 (23:07):
to hear again.
andrew-kisslo_1_02-11-2025_1 (23:07):
it is a, um, it was a wacky thing.
And I found, um, there werealways always 30 minute phone
calls and there's somethingabout asking friends and family
and people that you trust aboutcareer guidance because they
know you very closely.
Um, yeah.
But there is an element therewhere there is implicit bias
because they know you so well.
Um, and so, um, by findingpeople that had a job I thought
(23:28):
I wanted, um, it was always aninteresting 30 minutes.
It was always 15 minutes and 15minutes.
The first 15 minutes, I wouldask them, um, how did you get
the job?
Now that you have the job, Whatis the one job you wish you had
that would have prepared youbetter for the job now?
And it was always fascinating toget their take on that.
(23:49):
And then about minute 16, um, Iwould transition and I would
say, okay, you now know me 16minutes because most of these
people didn't know.
And I would say, here I am onpaper.
What do you think?
How do I come across?
What do I look like?
And so it was, it was, um, anabsolute clinic in how you
present yourself, how you showup, not only on paper, but in
(24:10):
person.
Um, And in those 15 minutes, youknow, they would give you a very
quick, um, assessment ofyourself.
Um, that was raw.
It was really good because itwas raw.
Um, and with that, with thosetwo 15 minute sessions, you
began to see the patterns overtime of how many of them
(24:31):
actually would say the samethings of jobs they wish they
had or the feeder kinds ofroles.
And then how many of themactually clued in on unbeknownst
to each other.
You need to go get PNL, you needto go get X.
And so it was a really, uh,fascinating.
I do think it was like the bestspeed dating on career I've ever
done.
It was hard.
I mean, asking people for timethat you do not know they're in
(24:54):
very lofty positions, um, was adifficult thing, but it ended up
being this sort of daisy chainof, well, I know a person go
talk to them.
And it ended up kind ofhappening.
Um, but a really great thing, nomatter what career you have.
Wacky idea, but best thing everdid.
emily-sander_1_02-11-2025 (25:10):
Yeah.
Love it.
Thank you for sharing thatstory.
I love it.
right.
So taking us to the next phaseof the life cycle here.
Um, when, when did you go, Oh, Ineed a chief of staff or how
andrew-kisslo_1_02-11-202 (25:20):
Yeah.
emily-sander_1_02-11-2025_1 (25:20):
how did the rec come about for like,
okay, now I'm looking for achief of staff.
andrew-kisslo_1_02-11-2025_1 (25:24):
So ultimately, um, you know, I
think once once I left the job,um, there is also that
transition of, um, even before Ineeded 1, um, I was a different
leader when I returns tocivilian life.
And it didn't dawn on me until Iwas no longer in the job.
Everything I had learned whenyou're in the job, you don't
(25:45):
know.
I'm doing budget.
I'm doing this.
Oh, my gosh.
It's a race.
It's a race.
It's a race.
Um, and then you leave it andthen you're in whatever your new
job is.
Um, and you're, you're, you'returning back to the home front.
Um, You start doing thingsnaturally and you kind of don't
know where they're coming from.
Your confidence in a room ofexecutives, you're just, you're
(26:06):
just doing things.
You're like, and people would belike, you just seem at ease.
I'm like, I don't know.
This just seems easy.
I'm not afraid.
Um, oh, you seem to be verydecisive and see strategy.
I don't know how I'm doing this,you know?
But when I look back, it wasbecause Of everything that I saw
and absorbed, and it wasn'tuntil I was out of it that I got
to draw upon it.
(26:27):
Um, so I would tell people ifyou do achieve a staff job, the
ROI is after not during.
Um, that's a key thing becauseit.
When you're in it, you just gotto get through it and just take
that risk that it will pay offfor me.
It did.
Um, you know, there became thenwhen I in my new role, um, of
(26:48):
why a chief of staff and why doI need one?
Um, you know, for the role thatI have at S.
A.
P.
Um, it's very complex, veryglobal in nature.
It has a lot of the elements ofwhat we're trying to do and
transform our own business,which are driving cloud and
culture.
Driving different, uh,commercial models that are
short, medium and long term.
(27:09):
So it started to fit the patternof for my own world in my own
different zip code.
Um, wow, this feels incrediblyfamiliar and it would be really
great, um, to have someone in arole that I can lean on, um, To
help me advance all those areas,um, as an executive, you just
can't do it all yourself.
Um, and sometimes you can't relyon your entire leadership team
(27:30):
to do it.
They have their own day jobs.
Um, and so asking a leader, um,who has a team of their own to
help you drive culture for theold org.
That's not fair.
Um, and so you end up having,you know, at some point the need
for.
This kind of a role to emerge.
Um, and so for me, it did.
And so, um, yeah, I, I, sincewe've last chatted, I found a
(27:50):
chief of staff.
Um, the job was,
emily-sander_1_02-11-2025_1 (27:52):
All
andrew-kisslo_1_02-11-202 (27:52):
yeah, and I, and I found someone
incredible.
Um, and she's on day 10, Ithink, probably
emily-sander_1_02-11-2025_1 (27:58):
Oh, wow.
andrew-kisslo_1_02-11-202 (27:59):
right now, um, but, um, You know, I
think the thing that in myselection, there was, I looked
at all different kinds of, um,of people and candidates and
the, the person that I, youknow, ended up picking, um, had
the 1 thing that is, um, youcan't teach and it was, um,
(28:21):
somebody that was coming intothe role with the, whatever,
whatever it takes and I don'tmean that in a, in a, in a trite
way, meaning like, um, I'm justhere to do what you tell me.
It was much more like.
I am here at the service ofmaking you and the org awesome,
and I am openly coming into therole knowing this isn't about
(28:44):
me.
It's about us, and for someoneto lead with that maturity right
out, you just kind of know theyget it.
They just get that that is thedown payment that you kind of
have to make where you suppressyour own ego for a while.
Because it's not about you.
It is about the org.
It is about the team and theleader, um, which means you are
(29:08):
in the shadows.
You are off and out of frame.
Um, your goal isn't to be inframe and be the hero.
That's not what a chief of staffis.
There are times where that iscalled for, but that's not the
job.
Um, And so, um, yeah, I'm, I'mthrilled with the choice.
She's going to be incredible.
Um, so, uh, I'm really excitedto, to watch her grow.
emily-sander_1_02-11-2025_1 (29:29):
And just what is the experience like
10 days in of being like theprincipal now?
Because you've been the chief of
andrew-kisslo_1_02-11-2025 (29:33):
It's weird.
emily-sander_1_02-11-2025_1 (29:34):
Oh, I'm actually, yeah.
andrew-kisslo_1_02-11-2025_12 (29:36):
I think, you know, my own lesson
is, um, you know, and she willbe my, my second chief of staff
is.
Um, you know, reflecting backhaving been 1 is, um, um, the,
my 1st chief of staff, um, wasshe had never been 1 and I was
like, oh, don't worry.
I've done it.
I can tell you all the things todo.
And here are all my oldplaybooks and all the things
that I can realize inretrospect, um, as helpful as
(29:58):
that was to help her ramp veryquickly.
I actually robbed her of all theexperience to come up with it on
our own.
And I was just like, Oh, don'tworry.
I'll just give you this stuff,which I can see how having been
one and being then a leader,there is an influence of power
there where, Oh, you're themanager and you kind of were
one.
So I'll just do what you said.
I was the chief of staff for atotally different company,
(30:20):
different leader.
And so for me to effectivelytake a playbook and say, just
run this, it stifled that.
Um, and so my 2nd time aroundwith the 2nd chief of staff, um,
is almost the opposite.
I'm like, if you need help, Ihave ideas.
Otherwise, I trust you.
Like, I'm listening to you.
Like, whatever you think youwant to do, let's go.
(30:42):
Um, and so trying to open up alittle bit more space and
freedom.
I certainly have opinions, um,but less more, um, run the book
and much more like, let's Youknow, let's paint this together
type of thing
emily-sander_1_02-11-2025 (30:55):
Yeah, for sure.
I think there's certainly likecommon threads, threads and
foundational pieces that wouldhelp pretty much any chief of
staff, but you have to help themwith their own playbook for like
their specific role, theirspecific principle in their
specific situation.
And that playbook is going tochange over time, even within
one role.
andrew-kisslo_1_02-11-2025_ (31:12):
all the time,
emily-sander_1_02-11-2025_1 (31:13):
So,
andrew-kisslo_1_02-11-2025 (31:13):
goes back to the chief of staff jobs.
Um, they are all very similar,you know, and we kind of talked
about this earlier.
There are shared traits of like,every chief of staff probably
has to deal with budget and hasto deal with some level of
culture.
Um, but it kind of stops there.
Everything else is as unique asthe leader.
You know, a leader can be on abusiness that's rising or dying.
(31:35):
A leader can be falling in favorout of favor.
A leader can have a big team,small team.
Um, and when you start throwingin all these variables, the job
starts morphing into somethingtotally different.
Um, and you can be in a roomwith a bunch of chiefs of staff.
And they get the, there's anunwritten language that everyone
kind of gets because you allkind of know what it is, how you
(31:57):
are doing your job at the end ofthe day, maybe so different
where you're like, wait, you dothat for your leader.
And you're like, yeah, do younot do that?
Oh, my leader doesn't want me todo that.
You know, and you end up going,oh, that's really different.
Um, you do budget, right?
Oh, yeah, do budget.
Um, you know, there are sharedcommon experiences.
Um, yeah.
But they are really unique.
That's why finding a chief ofstaff, um, is as hard as being
(32:20):
one because it is about thematch between a leader and a
chief of staff.
You know, you have to find theright person, but you have to be
the right person, um, becausethat is a really intense,
intimate, trusting relationshipthat you just can't plug and
play.
I mean, you have to find thatmatch.
Um, so they're, they're, they'repretty unique in that, in that
(32:41):
regard.
emily-sander_1_02-11-2025 (32:43):
yeah.
you for that.
As we wind down here, you and Ihave talked about, you, you
brought up this, um, greatanalogy in a previous
conversation we had about a, aco driver in a rally
andrew-kisslo_1_02-11-202 (32:52):
Yeah.
emily-sander_1_02-11-2025_1 (32:52):
And I just wanted you to share that
with you because it was so, sogood.
andrew-kisslo_1_02-11-202 (32:55):
Yeah.
emily-sander_1_02-11-2025_1 (32:55):
can you share that
andrew-kisslo_1_02-11-202 (32:56):
Yeah.
So I'll give you the background.
So a rally car driving, which iscertainly very popular in Europe
and other parts of the world.
Um, it's where cars go down dirtroads, usually incredibly fast.
Um, and there's always 2 peoplein the car, um, and there's a
driver and they actually callthem a co driver or a copilot.
Um, and, um, what that persondoes is they have a book in
(33:19):
front of them, And a microphone,um, and they are effectively
calling the plays for the driverand, um, the plays are we're
about to turn a 100 meters ditchjump all the things that are
predicting what's coming.
Um, and so I have a friend whodoes this and 1 weekend said,
hey, I, I've lost my co driverson vacation.
(33:41):
Do you want to do this for me?
And I was like.
Sure, I'm pretty crazy.
Um, here in the state ofWashington, we drove out into
the middle of old forest roadsand we jumped in his Subaru
rally car and had stickers andall the kinds of things and we
start hauling down the road like100 miles an hour on dirt roads,
trees whizzing past.
Um, and he was just sort ofwarming up the car.
(34:03):
Um, and he gave me a lesson, youknow, before we went to say, you
need to learn this language.
And I learned the language of.
Mhm.
Overcrest, right?
100 meters, blah, blah, blah.
And when we got there, I said,why do you need me?
You are driving very fast.
You kind of know what you'redoing.
And he said, no, no, no, youneed to understand.
(34:24):
I'm driving by what you'retelling me, not by what I'm
seeing.
And I was like, oh, really?
He's like, yeah, I'm, I'mreacting in the moment.
And so when you tell mesomething's coming over the
hill, and I now need to prepareto turn because we're going 100
miles an hour, you're helping meprepare.
And I always look back on thatas such a great metaphor of
(34:46):
chief of staff and leader wherea leader is acting in the moment
all the time and having someonethat is in the cockpit that
knows everything about fuel inthe car, speed of the car,
what's coming, you are callingthe plays.
Thanks.
And the driver or the leader candecide to not listen, but in so
many ways when it's humming andwhen it is working, it is in
(35:07):
concert of preparing and you'rejust in that dialogue actively
going back and forth of theleader is driving by what you're
telling them, not by whatthey're seeing and their gut is
coming forward.
But anyway, that was that wasthe analogy or metaphor we used
and it's just always worked forme because I think, um, it's
such a such a fascinating thingthat those 2 roles can do
(35:29):
together.
Um, that certainly applies.
I think in this kind of in thiskind of setting.
emily-sander_1_02-11-2025_124 (35:34):
I love that one.
It stuck with me.
So thank you for, for recountingit
andrew-kisslo_1_02-11-202 (35:37):
Yeah,
emily-sander_1_02-11-2025_1 (35:37):
But Andrew, you shared so much and
it's been, it's been great to,to talk with you again.
And, um, thank you very much fortaking the time and being on the
show.
Appreciate it.
andrew-kisslo_1_02-11-202 (35:46):
thank you so much for for this.
Um, and anytime, you know, Ithink we had joked also, there's
a saying amongst chief of staff,which is, you have to be smart
enough to do it dumb enough totake it, which is they are
phenomenal roles.
And I can say anyone that.
Finds an opportunity to do it.
Um, take it, you will not regretit.
Um, you know, there is lifebefore chief of staff and after
(36:06):
chief of staff.
And at least for me, it paid offin so many dividends of personal
growth and career growth, um,that it's, uh, for me was one of
the most important things I didin my career.
emily-sander_1_02-11 (36:17):
Beautiful.
We'll leave it there.
Thanks again,
andrew-kisslo_1_02-11-20 (36:19):
Thanks so much for the time.
See you.
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