Leveraging Leadership

Moving from Chief of Staff to Principal: Lessons from a Leadership Transformation at Microsoft

• Emily Sander • Season 1 • Episode 213

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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

emily-sander_1_02-11-2025_124418:

My guest today is Andrew Kislow, and he and I first connected because he was, um, recruiting and hiring a chief of staff for his, his team. And, uh, he has been in the chief of staff role at his 10 plus years at Microsoft. It was one of one of the many roles you've held there. Um, and so we're gonna talk about the lifecycle of chief of staff, and Andrew is well positioned to do that. So, Andrew, welcome to the show. Thank you so much for being here.

andrew-kisslo_1_02-11-2025_124419:

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_124418:

One of my favorite too. So just to give our listeners quick background and context, can you just give us some background for, for you and your career up to the point where you got to be chief of staff?

andrew-kisslo_1_02-11-2025_124419:

yeah, absolutely. Um, currently, I'm the senior vice president of global partner marketing at S. A. P. Um, but when I go in the way back machine, um, before I became a chief of staff and everything up to that, um, I started my career after business school, um, at a small startup, um, In the dot com era, when everything was going to take over the world, um, and it progressed, um, ultimately leading to a job at Microsoft, um, and had done a variety of roles at Microsoft, everything from product marketing, product management, um, and chief of staff or, um. You know, staff positions was always something that interested me. Um, and so there came a point in my career where I found the right opportunity at the right time to do that. But most of my background was in marketing, uh, and dealing with customers. So.

emily-sander_1_02-11-2025_124418:

Gotcha. Thank you. So can you just touch on a little bit of like what you thought about when you first heard chief of staff, what you, what that decision process was like going into that role, that whole phase of

andrew-kisslo_1_02-11-2025_124419:

Yeah, you know, I, I kind of go back to, um, even the history of the roles, because my first introduction to someone that was a chief of staff, um, you know, chief of staff positions have existed probably since, um, originally the, the, you know, as old as the military in the Roman days, there was always someone and we've always seen, you know, in TV shows, someone that was the right hand in either the mafia or even Game of Thrones, right? Um,

emily-sander_1_02-11-2025_124418:

Yeah.

andrew-kisslo_1_02-11-2025_124419:

in tech, they actually were born out of the origin, um, early on where they were called technical assistance. T. A. S. Um, and when you really think back to the, um, the birth of these tech companies, um, that usually in a founder culture, Microsoft Intel, uh, they usually had someone that had to support the founder that was the chief executive and they were typically T. A. S. Technical assistance. Um, and what those folks did was, um, Serve as a right hand person to help everything with demos on stage, um, to technical directions of the product. Um, and so my first introduction to someone that was a TA, um, was actually in my first role after business school. And the person had been a TA for Craig Barrett, who was the CEO of Intel, followed Andy Grove, um, and so, um, he was effectively a mentor for me very early in my career. And I was not technical, but I really loved his approach to how he, um, looked at everything in the 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 TA for a CEO. And I was like, what's a TA? And he really educated on me and started to open up my world of these special, unique roles that help executives scale. Um, and so that was my first introduction very early on. Um, when I left and joined Microsoft, um, Uh, I also, um, I remember the day I was in a room, I was a junior person, way in the back of the room, very important people, um, in the center of the room, um, and this young, lovely woman walked in and she started barking commands to everyone. And she was like, oh, you're full of shit. And oh, the numbers are wrong. And what are you guys going to do about this? And she walked out and I said, who was that? And they were like, oh, that's so and so's chief of staff. And I was like, wow, like, how did that person come in and command a room and know everything about the business? And effectively was there to not only force multiply, but to keep the business on track and it planted yet another seed in me of like, wow, that seems like a really, really unique job. Um, so I was introduced very early on to 2 very specific people who held that position in totally different ways. But it piqued my interest.

emily-sander_1_02-11-2025_124418:

Yeah. And it sounds like the, the through line of that is just you going, they see the whole business across the board holistically. Like how did they do that? And that's what got, got your attention among other things. So us to the point where it's like now you're being offered chief of staff and kind of who your principal was and did you know this person before and how you interacted and set up that role in relationship. Tell us all about that.

andrew-kisslo_1_02-11-2025_124419:

Yeah, I think, you know, in the journey of, um, I thought I wanted to be one. Um, and I got advice early on from someone, um, who had been chief of staff, um, very similar to maybe a listener today of their thinking about it. And the guidance I got early on was, um, these jobs aren't for everyone. And the key thing is before you even entertain it, um, you have to know why you're going after it. Um, or is this illusion of. There are super cool jobs, and you're gonna fly on jets, and you're gonna be in the coolest meetings in the world. Um, and while some of those things may be true every now and then, um, that's not the job. Um, and so you really have to go in with eyes wide open. Um, so I did the work, uh, before I even found a job to, uh, apply to, which was, um, I knew in my career at that time, I wanted an experience where I would learn how a leader thinks. How a leader leads. Um, and there are a couple of things that come along with that. How leaders drive culture at scale. Um, how leaders make decisions in the present for things that are short, medium, and long term. 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 so fundamental for any leader is, uh, business excellence. How do you manage the resources and headcount and money that you bring to bear, uh, to drive really important outcomes and really achieve a staff. Fundamentally touches all those things. They help culture. They help the bottom line and budgets and resources and strategy. And then they also help in the middle rallying all the capabilities of horizon zero all the way to horizon three of things that aren't that are, you know, a glimmer in someone's eye, but they're not here yet. And you have to hold space for all of that. Um, so that's what I knew I wanted 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 at Microsoft. And this was early in the days of cloud. We didn't really have an idea of what we wanted to be. Um, and I applied for the job and the leader said, Hey, you're perfect. I know you, you, you sort of can do all these things just enough, um, try the job. If you hate it, we'll find something else. And I was like, what could go wrong 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 caught lightning in a bottle in a couple of different ways where I worked for a leader who was a phenomenal person and leader on culture and strategy. And also for a business that was exploding, we used to commonly joke of we were doing things that they cannot teach you in business school. There is no business school class or professor ever. That knows how to take a billion in revenue and double it and double it and double it. Um, and just having exponential growth, um, while not having more resources. This is key. We were exploding the cloud business. Um, but we were not getting more headcount and we really weren't getting that much more budget. And so how do you extract a strategy that drives that much yield? Um, Is it was, it was a, an interesting ride for sure. Um, lots of very new business models and things that we experimented to. Um, but, uh, that, that was ultimately, you know, the position that I found that I was incredibly lucky, um, to be honest, to find that, you know, at that time,

emily-sander_1_02-11-2025_124418:

Wow. That's amazing. And can you just talk about, it sounds like so much was happening so quickly in those four years. And I'm assuming you tell me things were evolving at a rapid clip. So your chief of staff role was evolving as you moved along. Your principal's role was evolving as theirs moved along. Can you just talk about kind of how you progressed and, um, you know, when I was chief of staff, you would have to like be in it and like go in it and you're in kind of tunnel vision and then you would take a breath and zoom out and go like, where are we? What's happening? What's the long term? Um, and then go back in it in the short term. So kind of tell me a little bit about your experience in those four

andrew-kisslo_1_02-11-2025_124419:

yeah, you know, I think, I think, um, in the four years, you know, I kind of look back and, um, um, Every year I did it, um, there was something different happening in the business, right. And at least in tacking the pace, it was. You break down your business kind of almost into 90 day ship windows. Every 90 days you're shipping something and that's you're moving fast, but the external environment around you is moving faster. Um, and so, um, every time that you put a plan out there, you hope and pray that something doesn't happen externally where you have not to change it. Um, and that never holds, right? And so, um, you're constantly in the, in the business, like you mentioned, where, um, you're deep in the weeds and you're planning, uh, and then you surface for air and you're raising altitude and then you pressure drop again. And so this, This constant parabolas, I would say of altitude that you're in the business, um, of do we have the right strategy? I think we've got a vision and then you're like, like, execute and then you pop up and you're like, oh, my gosh, it's not working or something different happened. And you're constantly doing, um. This, um, that's why in some ways it's, it's not for everybody. It is hard. Um, and you have to hold your leader in the highest regard because your job is to make your leader and your org as awesome as possible yet behind the scenes. It can sometimes be utter chaos where you don't want. Um, a lot of that, uh, tumult or indecision to come forward, um, which is natural in any business. It's naturally in any single business. Um, but, you know, it, it requires different archetypes of chiefs of staff to kind of, you know, Come forward as well, um, at least in some of the research that we did, um, when I was in the role at Microsoft, and I think they're fair is there's sort of 4 archetypes of chiefs of staff. Um, and someone needs to flow through all of them, or you kind 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 specific and an engineering leader or are they kind of common? That's one axis. Um, the X axis is, is this an entirely new business or is this an old established business? And what we found was that with a couple of questions, it really led to four kinds of archetypes. Um, you have chiefs of staff that are fixers, And they go around and they fix stuff. Um, you have chiefs of staff that are Jack or Jill of all trades and they kind of need to float. And those would usually be in somebody that's a new business with a lots of breath. They're just everywhere. They're firefighting. Um, in that upper right. Um, you would have someone that's a force multiplier. Um, and the role of a force multiplier is very different than a Jack and Jill of all trades. They're in the opposite parts of the quadrant. Um, and then the final one is ring master. bringing everybody together and kind of driving and being an emcee. Um, and I think that in my four years, I floated through all of those modes based on the, on the, 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 I got this. I'm now a Jack and Jill of all trades. Cause I can kind of see it. And then you can kind of see, Oh, now I'm maturing. Um, um, but archetypes were really helpful for me to understand. Um, because the job is that nebulous. It's a living, breathing thing. Um, and so I think for people who come into the job, um, with the expectation of my job is very codified and it's the same, not this kind of job. Um, you really need to almost be okay with, um, that wide aperture. That's kind of constantly moving in and out, um, because it requires a lot of flex. So.

emily-sander_1_02-11-2025_124418:

It does. And like you said, it's not for everyone, which is not like a judgment call at all. It's just, you know, know your strengths. And, you know, I, I always thought of myself as like, Porpoising in and out of like the tactical and practical and up altitude and down altitude and all these things. Uh, and I, I love that. I love

andrew-kisslo_1_02-11-2025_124419:

Yeah,

emily-sander_1_02-11-2025_124418:

about so many different areas of the business, but if there are plenty of people that you need to sit and be like a subject matter expert. In this one area and just be like a technical expert. And like, you need those folks on your team and throughout your company as well. Um, but just know if you're going for a chief of staff role, you're probably going to be doing this. You're probably going to be going up and down quite a bit. And I, I love the, um, the quadrant accesses you mentioned, what's like breadth and depth. And then, you know, is this a new company, kind of a startup vibe or more of a established mature company? So much different versions of chiefs of staff. Um, With regard to your principal, what's something that you appreciated about her?

andrew-kisslo_1_02-11-2025_124419:

yeah, I think, you know, 1 of there's a, there's a couple of things that I appreciated about her specifically. 1 was, I really got a, a, a master's course, um, in authentic leadership that, um, that there are many leaders and I found we probably all know that you work with some or that you've worked around some, which are. Um, the leader who they are in the room with other people is not who they are outside of the room. They, they shift into a gear. Um, and those gears can ultimately, the more people aren't fools, um, you know, and people, the more that they work with executives, they can kind of see. Wait a minute, this, this executive isn't being authentic. They're not who they perceive to be for the better or the worse. Um, and, you know, the, the leader that I worked for was incredibly authentic, incredibly approachable, consistent to the team. It did not matter whether we were in the room with interns who just graduated from college to she was in a room in front of the board of directors or meeting a president of a country. Same person, same delivery. And that authenticity, um, really is a great lesson that 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 like the most, the most primitive lesson I got was, you know, Um, just leading from authenticity, um, and, and that can never steer anyone wrong, to be honest, um, that was, that was one, I think the other thing at the other end of the continuum that 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 had no problem constantly pressure testing and pushing. Um, and she was a change agent still is. Um, and so one of the things that she gave me as a lesson one time was, um, she said, you know, if you're going to be a change agent, um, what that means is you're signing up for a life of resistance. No one wants to be disrupted. Um, but when you are a change agent and you're going around and you're pushing on things, you're doing it because you believe that there is a better way, um, that can help the company. And so that really sometimes meets a lot of resistance. Um, and so being a change agent really is the only lever you have is pressure. How much pressure would always do this? How much pressure can you bring to 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 status quo in a, in a very thoughtful, deliberate and intentional way, not just yelling at people. It was always very strategic and well thought out. Um, but when she saw something that, um, could be better attack it, um, and bring people along. And, and the, the final lesson of that was, um, I would always ask her, like, you know, it feels kind of isolating when you're a leader and you're pushing and you're challenging because you can stand out and she would say, yeah, you know, but that's my job. That's why I'm here. That's what they're paying me to do. And she would say, I know exactly when my job is done and say, okay, what's the recipe? And she would say, I know my job is done as a change agent when someone else in the room says what I was saying, and I would say, okay, why that? And she goes, because now it's alive in the world with someone else to take care of. And it was really a Zen kind of approach to say, you're on your own and you're carrying a flag. And then the minute someone else carries the flag with you, and they're like, yeah, let's go charge the hill now. Change is actually happening. And there's someone else along for the ride, and then it multiplies from there. And when I look back in the patterns of all the things that we worked on, and that she was driving, it was such a pattern. It was always her alone as a voice. Then getting someone to be like, yeah, I agree with what you're saying. And then they would start speaking up and she would be like, there it is. And she would then focus on something else. And so it was this constant plant to seed, water it, and then have someone else tend to it. And then you're off to the next thing. 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_124418:

Thank you. Yeah. She does sound like a phenomenal little leader. So, can you talk us through and how you moved out of the chief of staff role? And then maybe, you know, a year or two after you were out of that role and you were reflecting back your experience as chief of staff, because as we all kind of put some distance between things, we can take a breath and just have a different perspective on things. And what were some of the lessons that you took after the fact?

andrew-kisslo_1_02-11-2025_124419:

Well, you know, I kind of go to when you're, when you're in, when you're in the job, there is no perfect time to do them as in how long you do them. You can have an incredibly intense one year of rotation, and it's time. Some people do them for a very long time. I did it for four years. Um, and so I kind of had been around the sun, as I like to say. A second time, a third time, a fourth time. And I began to see the patterns where I'm sure that fifth year would have been phenomenal. But for me, I had done my 10, 000 hours in understanding leadership, understanding culture and those types of things. So I knew for me, it was time. Um, and there is an element when you're in the job because you are back to porpoising and doing these parabolas. Your job is so different than your peers and you have this existential fear of like, does anyone know what I do? I don't even know what I do anymore. I'm an expert in everything yet. Nothing. Do I have transferable skills? Like it, it can come to a point where 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 a natural thing, I think, for any chief of staff. Um, for me, it came to the point where I had a recognition of, okay, it's time. And I needed to also make space for someone else to to take and breathe life into the job in their own way. Um, and so, um. You know, as I was thinking about it, I was very deliberate with my leader to say, I think it's time. Um, and with with her backing to go explore areas that were of interest and just have conversations. Um, and ultimately, um, I, I took a job, um, after it, that was part of a very good career, uh, conversation that I had, um, not only with her, but with other leaders, which was, you know, Um, it dawned on me very late in my career that maybe I actually could, could do things that was great at achieve a staff, um, role at, which are really things like a chief operating officer. Um, and so I asked her, I think I want to be a CEO after this job. Um, she said, I don't know anything about that. Um, go talk to CEOs. And that's okay. So best career advice ever got, um, someone said, Hey, when I did that, somebody challenged me, 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 somebody that was a COO who then introduced me to another COO. And I went through this speed dating course of COOs. And I think I got to 25 and like 35 days. Um, Of companies of all sizes. Um, and what I got was really great feedback from them of. Um, here's your, with your background, here's what we recommend where you fill in, um, skills and capabilities to go become a COO of a very specific kind, change agent COO. Um, and with that, they said the one thing with your background, um, that you just need to show, because you've done marketing, you've done sales, you've done kind of everything. And with a chief of staff job, awesome. You need to prove that you can move a P& L. I was like, okay.

emily-sander_1_02-11-2025_124418:

Hmm.

andrew-kisslo_1_02-11-2025_124419:

So the job that I found after that was, um, designed where I talked to the CMO of Microsoft. Um, and he said, Hey, you should take this job because that will give you P and L. And I said, wow. Okay. Wow. So I took a job that was really that category killer for me to fill out a P and L capability. Um, and long story short, I did that for a while, um, before ultimately, um, Finding the role that I have now at SAP, um, which still is a feeder type of role into COO jobs. Um, and so, you know, at the end of the day, your company doesn't own your career, you do, and you really have to put the thought into Um, self scouting and where you weak and where you strong and then try to stitch together experiences that fill in, um, the things that you're going to need. Ultimately, at some point in the future,

emily-sander_1_02-11-2025_124418:

And I just want to highlight what you just said. So the fact that you took, took massive action, you know, 25 people in 35 days, that's no small feat. And you got feedback and you ask, you know, know, where do you see my strengths? Where do you see my gaps? You know, what would your recommendation be? Kind of what's your outside perception, not putting too much weight on other people's perception, but also you're in the role that I want to be in and you're successful. Like, help me, help me learn some 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_124419:

it's

emily-sander_1_02-11-2025_124418:

to hear again.

andrew-kisslo_1_02-11-2025_124419:

it is a, um, it was a wacky thing. And I found, um, there were always always 30 minute phone calls and there's something about asking friends and family and people that you trust about career guidance because they know you very closely. Um, yeah. But there is an element there where there is implicit bias because they know you so well. Um, and so, um, by finding people that had a job I thought I wanted, um, it was always an interesting 30 minutes. It was always 15 minutes and 15 minutes. The first 15 minutes, I would ask them, um, how did you get the job? Now that you have the job, What is the one job you wish you had that would have prepared you better for the job now? And it was always fascinating to get their take on that. And then about minute 16, um, I would transition and I would say, okay, you now know me 16 minutes because most of these people didn't know. And I would say, here I am on paper. What do you think? How do I come across? What do I look like? And so it was, it was, um, an absolute clinic in how you present yourself, how you show up, not only on paper, but in person. Um, And in those 15 minutes, you know, they would give you a very quick, um, assessment of yourself. Um, that was raw. It was really good because it was raw. Um, and with that, with those two 15 minute sessions, you began to see the patterns over time of how many of them actually would say the same things of jobs they wish they had or the feeder kinds of roles. And then how many of them actually clued in on unbeknownst to each other. You need to go get PNL, you need to go get X. And so it was a really, uh, fascinating. I do think it was like the best speed dating on career I've ever done. It was hard. I mean, asking people for time that you do not know they're in very lofty positions, um, was a difficult thing, but it ended up being this sort of daisy chain of, well, I know a person go talk to them. And it ended up kind of happening. Um, but a really great thing, no matter what career you have. Wacky idea, but best thing ever did.

emily-sander_1_02-11-2025_124418:

Yeah. Love it. Thank you for sharing that story. I love it. right. So taking us to the next phase of the life cycle here. Um, when, when did you go, Oh, I need a chief of staff or how

andrew-kisslo_1_02-11-2025_124419:

Yeah.

emily-sander_1_02-11-2025_124418:

how did the rec come about for like, okay, now I'm looking for a chief of staff.

andrew-kisslo_1_02-11-2025_124419:

So ultimately, um, you know, I think once once I left the job, um, there is also that transition of, um, even before I needed 1, um, I was a different leader when I returns to civilian life. And it didn't dawn on me until I was no longer in the job. Everything I had learned when you're in the job, you don't 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 and then you're in whatever your new job is. Um, and you're, you're, you're turning back to the home front. Um, You start doing things naturally and you kind of don't know where they're coming from. Your confidence in a room of executives, you're just, you're just doing things. You're like, and people would be like, 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 very decisive and see strategy. I don't know how I'm doing this, you know? But when I look back, it was because Of everything that I saw and absorbed, and it wasn't until I was out of it that I got to draw upon it. Um, so I would tell people if you do achieve a staff job, the ROI is after not during. Um, that's a key thing because it. When you're in it, you just got to get through it and just take that risk that it will pay off for me. It did. Um, you know, there became then when I in my new role, um, of why a chief of staff and why do I need one? Um, you know, for the role that I have at S. A. P. Um, it's very complex, very global in nature. It has a lot of the elements of what 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. So it started to fit the pattern of for my own world in my own different zip code. Um, wow, this feels incredibly familiar and it would be really great, um, to have someone in a role 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 rely on your entire leadership team 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 the old 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, since we've last chatted, I found a chief of staff. Um, the job was,

emily-sander_1_02-11-2025_124418:

All

andrew-kisslo_1_02-11-2025_124419:

yeah, and I, and I found someone incredible. Um, and she's on day 10, I think, probably

emily-sander_1_02-11-2025_124418:

Oh, wow.

andrew-kisslo_1_02-11-2025_124419:

right now, um, but, um, You know, I think the thing that in my selection, there was, I looked at all different kinds of, um, of people and candidates and the, the person that I, you know, ended up picking, um, had the 1 thing that is, um, you can't teach and it was, um, somebody that was coming into the role with the, whatever, whatever it takes and I don't mean that in a, in a, in a trite way, meaning like, um, I'm just here to do what you tell me. It was much more like. I am here at the service of making you and the org awesome, and I am openly coming into the role knowing this isn't about me. It's about us, and for someone to lead with that maturity right out, you just kind of know they get it. They just get that that is the down payment that you kind of have to make where you suppress your own ego for a while. Because it's not about you. It is about the org. It is about the team and the leader, um, which means you are in the shadows. You are off and out of frame. Um, your goal isn't to be in frame and be the hero. That's not what a chief of staff is. There are times where that is called for, but that's not the job. Um, And so, um, yeah, I'm, I'm thrilled with the choice. She's going to be incredible. Um, so, uh, I'm really excited to, to watch her grow.

emily-sander_1_02-11-2025_124418:

And just what is the experience like 10 days in of being like the principal now? Because you've been the chief of

andrew-kisslo_1_02-11-2025_124419:

It's weird.

emily-sander_1_02-11-2025_124418:

Oh, I'm actually, yeah.

andrew-kisslo_1_02-11-2025_124419:

I think, you know, my own lesson is, um, you know, and she will be my, my second chief of staff is. Um, you know, reflecting back having been 1 is, um, um, the, my 1st chief of staff, um, was she had never been 1 and I was like, oh, don't worry. I've done it. I can tell you all the things to do. And here are all my old playbooks and all the things that I can realize in retrospect, um, as helpful as that was to help her ramp very quickly. I actually robbed her of all the experience to come up with it on our own. And I was just like, Oh, don't worry. 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 the manager and you kind of were one. So I'll just do what you said. I was the chief of staff for a totally different company, different leader. And so for me to effectively take a playbook and say, just run this, it stifled that. Um, and so my 2nd time around with the 2nd chief of staff, um, is almost the opposite. I'm like, if you need help, I have ideas. Otherwise, I trust you. Like, I'm listening to you. Like, whatever you think you want to do, let's go. Um, and so trying to open up a little bit more space and freedom. I certainly have opinions, um, but less more, um, run the book and much more like, let's You know, let's paint this together type of thing

emily-sander_1_02-11-2025_124418:

Yeah, for sure. I think there's certainly like common threads, threads and foundational pieces that would help pretty much any chief of staff, but you have to help them with their own playbook for like their specific role, their specific principle in their specific situation. And that playbook is going to change over time, even within one role.

andrew-kisslo_1_02-11-2025_124419:

all the time,

emily-sander_1_02-11-2025_124418:

So,

andrew-kisslo_1_02-11-2025_124419:

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 has to deal with some level of culture. Um, but it kind of stops there. Everything else is as unique as the leader. You know, a leader can be on a business that's rising or dying. A leader can be falling in favor out of favor. A leader can have a big team, small team. Um, and when you start throwing in all these variables, the job starts morphing into something totally different. Um, and you can be in a room with a bunch of chiefs of staff. And they get the, there's an unwritten language that everyone kind of gets because you all kind of know what it is, how you are doing your job at the end of the day, maybe so different where you're like, wait, you do that for your leader. And you're like, yeah, do you not do that? Oh, my leader doesn't want me to do 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 shared common experiences. Um, yeah. But they are really unique. That's why finding a chief of staff, um, is as hard as being one because it is about the match between a leader and a chief of staff. You know, you have to find the right person, but you have to be the right person, um, because that is a really intense, intimate, trusting relationship that you just can't plug and play. I mean, you have to find that match. Um, so they're, they're, they're pretty unique in that, in that regard.

emily-sander_1_02-11-2025_124418:

yeah. you for that. As we wind down here, you and I have talked about, you, you brought up this, um, great analogy in a previous conversation we had about a, a co driver in a rally

andrew-kisslo_1_02-11-2025_124419:

Yeah.

emily-sander_1_02-11-2025_124418:

And I just wanted you to share that with you because it was so, so good.

andrew-kisslo_1_02-11-2025_124419:

Yeah.

emily-sander_1_02-11-2025_124418:

can you share that

andrew-kisslo_1_02-11-2025_124419:

Yeah. So I'll give you the background. So a rally car driving, which is certainly very popular in Europe and other parts of the world. Um, it's where cars go down dirt roads, usually incredibly fast. Um, and there's always 2 people in the car, um, and there's a driver and they actually call them a co driver or a copilot. Um, and, um, what that person does is they have a book in front of them, And a microphone, um, and they are effectively calling the plays for the driver and, um, the plays are we're about to turn a 100 meters ditch jump all the things that are predicting what's coming. Um, and so I have a friend who does this and 1 weekend said, hey, I, I've lost my co drivers on vacation. Do you want to do this for me? And I was like. Sure, I'm pretty crazy. Um, here in the state of Washington, we drove out into the middle of old forest roads and we jumped in his Subaru rally car and had stickers and all the kinds of things and we start hauling down the road like 100 miles an hour on dirt roads, trees whizzing past. Um, and he was just sort of warming up the car. Um, and he gave me a lesson, you know, 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're doing. And he said, no, no, no, you need to understand. I'm driving by what you're telling me, not by what I'm seeing. And I was like, oh, really? He's like, yeah, I'm, I'm reacting in the moment. And so when you tell me something's coming over the hill, and I now need to prepare to turn because we're going 100 miles an hour, you're helping me prepare. And I always look back on that as such a great metaphor of chief of staff and leader where a leader is acting in the moment all the time and having someone that is in the cockpit that knows everything about fuel in the car, speed of the car, what's coming, you are calling the plays. Thanks. And the driver or the leader can decide to not listen, but in so many ways when it's humming and when it is working, it is in concert of preparing and you're just in that dialogue actively going back and forth of the leader is driving by what you're telling them, not by what they're seeing and their gut is coming forward. But anyway, that was that was the analogy or metaphor we used and it's just always worked for me because I think, um, it's such a such a fascinating thing that those 2 roles can do together. Um, that certainly applies. I think in this kind of in this kind of setting.

emily-sander_1_02-11-2025_124418:

I love that one. It stuck with me. So thank you for, for recounting it

andrew-kisslo_1_02-11-2025_124419:

Yeah,

emily-sander_1_02-11-2025_124418:

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 for taking the time and being on the show. Appreciate it.

andrew-kisslo_1_02-11-2025_124419:

thank you so much for for this. Um, and anytime, you know, I think 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 to take 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 regret it. Um, you know, there is life before chief of staff and after chief of staff. And at least for me, it paid off in so many dividends of personal growth and career growth, um, that it's, uh, for me was one of the most important things I did in my career.

emily-sander_1_02-11-2025_124418:

Beautiful. We'll leave it there. Thanks again,

andrew-kisslo_1_02-11-2025_124419:

Thanks so much for the time. See you.