Leigh Felton has over 25 years of experience working in executive operations and chief of staff positions for companies like Microsoft and the State of Washington.

In this episode of The Leader Assistant Podcast with Jeremy Burrows, Leigh talks about the two primary types of chief of staff – a rotational chief of staff and career chief of staff, the differences between an executive assistant and a chief of staff, and the ethical and responsible use of AI and large language models.

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A good Chief of Staff makes the job look easy. A good CEO knows that it’s not.


Leigh Felton has over 25 years working in chief of staff and executive operations halls for companies like Microsoft, Mozilla, and the State of Washington.

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Leigh Felton 0:00
Hi, I’m Leigh Felton. And as we talk about the chief of staff role today, one of my absolute favorite quotes from my book is a good chief of staff makes the job easy. A good CEO knows that it’s not

Podcast Intro 0:19
the leader assistant assistant podcast exists to encourage and challenge assistants to become confident game changing leader assistants.

Jeremy Burrows 0:33
With so much on your plate, wouldn’t it be nice if ordering food for the office were easy and reliable. My friends at ezCater our workplace catering pros helping you find food for everything from daily employee meals to staff meetings and special events. With ezCaterer’s network of over 100,000 restaurants nationwide, you’ll have a huge variety of options near you for any group size, dietary need or budget. Your food arrives on time as ordered all supported 24/7 by ezCater’s team of experts. Visit ezcater.com/leaderassistant to find out more. Hey friends, welcome to The Leader Assistant Podcast. It’s episode 225. And to check out the show notes you can go to leaderassistant.com/225 leaderassistant.com/225. Today I am excited to be speaking with Leigh Felton. Leigh has over 25 years of experience working in chief of staff and executive operations for companies like Microsoft and Mozilla and the state of Washington. Leigh is also author of the Amazon book unlocking your inner chief of staff guide to maximizing organizational impact. And Leigh , I’m very excited to finally meet you and have you on the show. Welcome.

Leigh Felton 1:57
Absolutely. Thank you so much, Jeremy for having me.

Jeremy Burrows 2:01
So tell us a little bit about yourself personally. Do you have hobbies? Do you have a favorite? You know, Netflix show right now? What city? Are you in all that fun stuff?

Leigh Felton 2:10
Well, well, I actually right now I’m in Woodinville Washington. And so I’ve spent the majority of my life in Washington State, I was actually born in Jackson, Mississippi. So my roots and my heart really comes from the south. And one of the things that I love, especially as I think about my career, and the trajectory of where I’ve gone is being able to bridge between so many different cultures and experiences. And you know, people and they’re such a tremendous, they’re such a tremendous thing that we can learn from both, you know, the Pacific Northwest, the Seattle area, as well as Mississippi that I just love to bring all of that together and represent those audiences.

Jeremy Burrows 2:53
Nice. Nice. So what about hobbies? Or, you know, anything, any quirks? I

Leigh Felton 3:02
stood out of me, um, I do have a hobby. And it’s the one thing because I am always, you know, doing something when it comes to chief of staff or operational roles. There’s always a million things to do, but when I enable to shut off and get away I love anime. I do I love anime. It is my secret indulgence.

Jeremy Burrows 3:32
That’s awesome. Cool. Well, yeah, thanks, again for being on the show. Let’s, let’s jump right into your career. Quite a lot of interesting companies and even, you know, dropped job titles. But how did you end up as the chief of staff and maybe just give us a little bit of a story line of okay, you know, did you start off as an assistant or, you know, an operations and then move to chief of staff? Did you go back and forth kind of what was that trajectory?

Leigh Felton 4:12
Well, actually, I started out, my major in college was Broadcast Communications. So I wanted to be on TV, I wanted to be a star, I wanted to host my own television show, you know, you name it, or my own radio show, I didn’t care. I just, I wanted to be a figure. And that I wanted to speak for a living. And that led me of all places to MSNBC online. So at the very beginning, when Microsoft and NBC Universal, created a new company, MSNBC, they had an online version, which was a technology face of the company. And so that was based in Redmond, Washington at Microsoft’s headquarters, whereas obviously the television station that’s the Television Network is in Secaucus, New Jersey. So I got this position at MSNBC online, which is different than MSNBC, television or network. And I immediately thought, Okay, this is going to lead me even though it’s a, it’s a, you know, marketing, communications marketing position, this is going to lead me to Secaucus, New Jersey, or I’m going to have an opportunity to have my own show on MSNBC, it doesn’t work like that. But that’s okay, because I actually doing business communications, which is what my master’s degree is, in doing business communications, actually is a significant passion. And so being able to bring a voice in a brand, to MSNBC online and to be one of the original employees of MSNBC online was just magnificent. Which then led me to my first full time role at Microsoft, and the doors being opened for me to start as a marketing communication specialist, and Microsoft, which, you know, I just grew my career over 20 years, and Microsoft from doing marketing communications to running all of the PR, public relations, analyst relations and executive communications programs for all of Microsoft Server businesses, to doing this consumer broad reach launch of Windows XP. And then ultimately getting after Windows XP getting a taste of this brand new role. That was this thing called chief of staff. And at the time chief of staff business manager were co mingled. But it literally was the the chief of staff or an executive organization or CEO of that organization. And I was able to be seen as scuze, me chief of staff for the, the executive that ran all of Microsoft, HR generalist organization, which is huge, because you go from being an individual who, okay, if you’re at Microsoft, in a company like that, the company is whatever organization that you working for. So if you’re in Windows, Microsoft has windows, if you’re an Office, Microsoft has office, if you’re, you know, in legal, Microsoft is legal, it’s it’s very tunnel vision like that. But when you are in a position where I was able to be a chief of staff for the entire generalist organization for Microsoft HR, you got to see literally the underbelly of how a company operates, you got to see that really all of these companies are being held together with super glue and duct tape. I mean, and so it was, I’m so glad it was my very first chief of staff role, because it enlightened me to the shiny objects of an executive. They’re not so shiny, they’re not so shiny. There’s a lot of, you know, non sparkling stuff in an executive office. And so doing that early, just really helped me stay grounded in all of the future chief of staff and I ran business services for the state of Washington, which was all economic development, marketing, communications, important exports, for Governor Christine Gregoire in Washington, as well. But it really kept me grounded that very first chief of staff role kept me grounded on knowing that there’s problems everywhere.

Jeremy Burrows 8:34
Yeah. Wow. So what So chief of staff has kind of been? Well, I’m trying to look at your LinkedIn so that it’s kind of been a hot title, if you will, over the last, I don’t know, few years, at least. It really

Leigh Felton 8:53
blew up in the last two years before that. It was very seamless, confusing, but it was not as popular as it is right now.

Jeremy Burrows 9:02
Yeah. So you worked as a chief of staff before it was hip and trendy. And then it looks like you also worked as a chief of staff, while it was hip and trendy. So what’s why why is why is it gotten so much attention?

Leigh Felton 9:19
Well, for two things. I’ll address two things here. The first is, why do I keep going back to the chief of staff role? And I think for a lot of individuals that I call in, you’ll see in the book, it says there’s two different types of Chiefs of Staff. There are rotational Chiefs of Staff, and there are career teams, chiefs of staff. So rotational chiefs of staff really are line of business owners that want to understand like I was telling you all the down and dirty secrets in an executive office or rotational chief of staff in order for them to eventually run their own company or business. You rotate them into a chief of staff role for a couple of years to give them a taste of what that executive office is like. And then they rotate back into into a line of business of Career chief of staff is one like myself that for whatever reason, we find the chaos and the juggling and the, the personalities, we find that intriguing and motivating, and we stay with it for the majority of our careers. And so that’s what happened to me that I just got into this role. And it was so busy a different job every single day, that I loved it, and I could operate in that chaos. And I just decided that that was, so that was me. So that is why I chose to be a career chief of staff. Now, in terms of why is the position so popular today? It’s because people are realizing, executives are finally realizing, because of the blood sweat, and the tears of so many chiefs of staff that have come before, you know, before it got to be such a popular title. They’re seeing, Oh, my gosh, executives who have these Chiefs of Staff, and when they’re in their executive summits, and they’re talking to, you know, other executive, you know, peers, they’re talking about two positions, that you if you have them, you realize how on earth did I become this senior, this executive without these to support you no more than support, but these two incredible, senior talented roles that provide so much impact to me, personally, and that is the executive assistant, and that is a chief of staff, for executives who have never had a chief of staff. When they speak to a CEO who has had a wonderful chief of staff, I guarantee you, they immediately go out and try to figure out how to do a budget to get one. Yeah,

Jeremy Burrows 11:52
Bryce. So you mentioned executive assistant, as part of that, that trio, if you will, the executive, the executive assistant and the chief of staff. Tell us a little bit about your experience, you know, from the chief of staff seat, working with the assistant, and then maybe even give us a couple of major differences between the role EA, executive assistant and chief of staff.

Leigh Felton 12:25
Yeah, me, Jeremy, I sincerely appreciate you asking the question, because as the title chief of staff is blown out. Now, we know you know more than I do, the executive assistant role has, I think it’s like it was born with the CEO. Right? So the executive assistant role goes back to the dawn of time. And for good reason. If I only if I were a CEO, and I had, let’s not say budget, but let’s say I had a headcount for one person in my office, that one role that I would hire isn’t executive assistant. If I had the headcount for two, then yes, I’d hire an executive assistant, and a chief of staff. And, and I have to be careful when I speak with people. When I when I speak, in general, when I you know, I do a lot of consulting and educational presentations around the chief of staff position. And I have to be careful coming across like, gosh, isn’t that just obvious, to me, the executive assistant role and the chief of staff role are so greatly different. It amazes me sometimes that people actually can get them confused. And so, like I said, I’ve worked with some of the most brilliant, amazing executive assistants, I think that are out there. And whenever I get a microphone, to talk about the EA role, I am very clear to people, the EA role is a role to be respected. It’s a senior function in its own right. And people say well doesn’t you know, I need to become a chief of staff in order to go to the next level. I do not see that transition to the trajectory of EA they’re not in the same business line. You don’t go from admin or you know, business administrator to EA to business manager to EA now some people do, but that is that is because they have chosen just like some people I went from business communications and marketing to chief of staff. And so there’s different career lines and career paths. There’s a lot of people in finance that go from being finance controllers, running financial operations and analysis to being chief of staff because a lot of chief of staff rules relate to heavily on the financial aspect of things, but there’s many many different routes to get to a chief of staff role. Yes, being an EA is one of them, but I wouldn’t even say being a Kick Ass EA, if I’m allowed to say that, I wouldn’t even say that that is what leads you to achieve a sacral. Because you are amazing in your own right as an EA and I just My hope is that someday the industry would acknowledge the seniority and significance of the EA role and as a member of the executive leadership team, and compensated accordingly. And it’s because of that compensation. And the title EA has become synonymous with, with assistant like, you know, you are just an executor, a person that is part of, you know, part of this executive, that you are not strategic, and senior, and all of those things in the lines of business that you own. And that’s just not true. And so hopefully, my hope, my dream is that one day, you know, the two worlds will start being called muddled because they’re really being called meddled. Because of the title of an EA, it’s more hip, especially these days to be called the chief of staff, even when half of the will not have Okay, I’ll say maybe 10% of the job descriptions that I’m reading for chief of staff, the first five things are wholly EA responsibilities. And so the the biggest difference between the two roles, is if you think about it, the EA, is the line of business for the EA, is running and managing that CEO. And that CEOs time. And so it’s like how is the CEO using their time, their presence? And where does that need to be prioritized? How does that show up? And how do I make it as effective and efficient as possible? Now take a chief of staff, and you take that same how does this organization so it’s the CEOs organization? So this awful business? How does this business show up? And how do I make sure that every single employee in this organization show up as effective and efficient as possible?

Jeremy Burrows 17:13
Wow, that’s great, super helpful description. And, you know, I think that it’s going to continue to be a hot topic. And I’ve talked about this topic with other assistants and chief of staff on the podcast, but I really like how you broke it down. And a very simple, clear explanation of, hey, this is the difference. And I think that it’s going to be very helpful to those listening as they’re wrestling with, Hey, am i chief of staff? Do I want to be a chief of staff? You know, and then I guess, one follow up to that would be, if I’m listening to what you just said, and I still want to level up, you know, quote, unquote, level up in my executive assistant role. But you kind of told me that chief of staff isn’t necessarily the next level for executive assistant. So how would you encourage those listening? And maybe what have you seen in your career as the next step for an EA that likes the role loves supporting that that executive, but, you know, wants to make more money and wants to take on more responsibility, but maybe he doesn’t want to be a Chief chief of staff as you’re describing it?

Leigh Felton 18:30
Right. And I would say, first of all, I want to be realistic in that the market for compensation, when it comes to any position compared to chief of staff position are not even close. And I know that, and I would never discourage any EA, who wanted to go in that career direction, I would never discourage any EA to pursuing that career, that direction, whatever it is that motivates them. Only you can decide what is your you know, what is the determining factor, whether it’s salary, whether it’s responsibility, whether it’s title, I mean, people are rewarded and recognized by different things. And so I would never try to tell somebody that no, this is not the direction for you go in the direction that your heart is telling you is the right one, what I would say is, and I’ve met EAS, who wanted to say, Oh, I you know, it’s not about title, I like my title, but I want to make more money and the way to make more money is to become a business manager, etc. And I’ve had had very senior just some of these EAS run circles around certain members of leadership teams, just that, you know, magnificent, but they to get more money they stepped into a business manager roles, and within a year have stepped back into the DEA role. Because depending on what really drives your fire, you will find And the EA role actually has more authority than almost any other position in the CEOs, staff, or at least it should I mean, so for any EA that is even considering being a chief of staff, you have to show up like that you have to show up as a member of the leadership team, first and foremost as an EA. So if you don’t have that presence, and you are showing up at the leadership team, as an observer, or you know, you’re not actually a participant, you don’t actually have a voice. I would say before even considering going in the direction of chief of staff, you need to find your voice as an AE, because that is a powerful, powerful role. Yeah, well, I’m a fan of vas, because I’ve worked with some I mean, it’s a, it is a it’s a three way. So it’s more than a three way you have the CEO relationship with the chief of staff, you have the CEO relationship with the IED, you have the chief of staff relationship with the EAA, all of those relationships are significant, and how you’re fostering them what they stand for, then you have the what I call the three way you have the CEO, the chief of staff and the EAA. And in every chief of staff role that I’ve had, I have always my preference is to have two quick three, way six per week. But at the minimum, so it’s one of what I call non negotiables. So one of my non negotiables is that we have a three way sync at least one time per week. Yeah.

Jeremy Burrows 21:34
Nice. Well, you know, this is, again, this is great, great conversation, I love love your ideas in your in your clarity on the roles. But I want to really dive into you know, I noticed on your LinkedIn, when you were at Microsoft, there was a head of responsible AI enablement, which is another hot topic. So if you can, chief of staff was a hot, hot topic, AI is even harder. And so what what are your thoughts on the whole AI taking my job AI, making me a better employee? And then the ethical and responsible AI side of things? What’s your, what’s your AI spiel?

Leigh Felton 22:22
Are we actually starting a whole new podcast? Because that’s gonna say, yeah, that is such a huge topic. And, and when we talk about areas of just ultimate passion, and, you know, motivation, I mean, I love that chief of staff role only because we’re, you know, for 20 years, I’ve been in the realm of that position. So I know it inside and out, I’ve helped to shape it for many, many organizations, including many organizations across Microsoft, I’ve mentored so many amazing chiefs of staff. And so that’s where my vocabulary and the narrative that I have on the chief of staff role comes from, it’s that those 20 years of helping to formulate what that position is for the market. You talk about AI, and you have me take off one hat, and then I put on my other hat, which is my, my, what I call my responsible AI hat. And I was very, very fortunate to have the opportunity when Microsoft was initially thinking about what they called ethical AI, they had a couple of volunteers across the company that were part of this volunteer group, and they wanted somebody to come help formulate and shape what this program could possibly be. So they brought me on as program lead, to help work with these amazing senior talented, really volunteers, people that had full time jobs and other parts of the company that were volunteering to be part of this, you know, investigative pilot, and I did not know back then, how absolutely fortunate I was for getting in on the ground up. But what this was going to blow up to be I had no clue. So the fact that I have, you know, seven years in my pocket of structuring and helping to build, you know, responsible AI and ethical AI for the engagement and the implementation, how we’re thinking about it in our engineering groups and our sales groups that I had seven years of helping to build that from Microsoft, and then I have 20 years of chief of staff just like the stars just aligned for me in the last four years.

Jeremy Burrows 24:37
Wow. So what’s the so as as an assistant or chief of staff How do you practically implement AI and what do you what’s maybe the top thing you look for when it comes to you know, the, the responsible part of it.

Leigh Felton 24:57
So whenever I talk about AI I will always be under the microscope of using AI responsible, it will always be under the microscope of questioning AI, leveraging it as a tool, but not using it as a source. It is not the ultimate version of anyone’s truth. And we need to be very careful that too many people are starting to think about it like that, we get very comfortable with technology, we’re used to calculators, calculators, every single time we put in two plus two calculators will tell us score every single time, AI is not like that. And everything that it comes back with. First of all, isn’t necessarily accurate, at all. So but even if it gets better, and we can start relying on it more to be accurate, these large language models, so if we talked about chat GPT, for instance, there’s so many different types of AI. And I’m guessing since what’s really blowing up right now is large language models, generative AI, like chat GPT frt, which is facial recognition technology, it went through a period about four years ago, where it was trying to blow up like Chet GPT. But it got so much resistance because people, I mean, it was evident with facial recognition technology, that the technology was just wrong, it was just inaccurate, and it didn’t work for huge portions of the population. So they went back to the drawing board and trying to redo that one. But Chad GPT, it comes back with a words I want to write an essay on, I don’t I will write an essay on the amazing, amazing chief of staff role and why that’s so cool. It’ll write an essay for me, but I guarantee you all of the things Jeremy that you and I just talked about, it cannot replace the expertise that I have 20 years, the the essay will not sound anything like the first half of this interview between the two of us. And that’s because what it’s doing, it can only go off of the historical data that has been fed. And so what it’s doing is it’s just sourcing through mounds and mounds and mounds and mounds and mounds and mounds amounts of information. And in some context, it’s bringing what is bringing you back. So your essay, that you think, hey, it was created by AI, I put my name on it, and you can because there there’s no legislation or you know, policies or regulation or anything right now that says the AI content that you are, you know that you are that you’re getting fed could not be yours. But a lot of the content, it’s coming back with in very significant portions, it is pulling from other sources. And so you actually could be plagiarizing without even knowing it. You could be you know, having first incorrect content, because I can’t tell you how many times I’ve asked check GPT stuff. And it’s like, and I even tell it Chad GPT you’re wrong on this, actually, you know, this is what this is what the truth is, and this is a cool, thank you so much. You’re right, you know, blah, blah, blah, blah, blah, blah, blah. And so it’s it’s not, it’s just trying to get you information. And it’s trying to just like any other technology out there, when we talk about when we talk about cloud services, they’re learning from us, it’s all data is all data driven. And data is gold data is actually I think data is gold dust. But that’s a whole nother story. But data is golden. And it’s learning from you. So as much as you think that you’re using Chet GPT to do all of your work, it’s actually using you to try to become the best and the best, you know, the the best and the brightest in the market. But again, I say all of this with the notion that we lead with our expertise. So even that essay, or that paper or whatever it is that you’re trying to write. If you don’t have an expertise and an expert handle of your topic, then you don’t know what the right questions are. They ask, you don’t know whether to question the content that you’re getting back. But if you can really hone in on your area of expertise on what it is that you uniquely offer. My gosh, will these technologies save you time?

Jeremy Burrows 29:15
Yeah, I was gonna say what’s your what’s your number one use case right now like for you personally? Or professionally with AI? Like, are you using chat? GPT? Are you using a different AI tool?

Leigh Felton 29:29
I’m with everybody else. I’m hopping on that bandwagon. In chat. GPT let me just tell you, there are things that I had to prepare for. There’s a lot of stuff that if you see my book, you will see that there’s no way like any of it was written by Chet GPT because it’s it’s literally an executive coloring book. And it’s not that these are your essay numbers and what and what you need to consider is 123 and charge up to He has that same structure with basically every answer it gets back in. But in terms of research, just trying, you know, I do a lot when it comes to understanding the impact of technology in Black and African American communities. And so my number one use right now is really trying to dig into what are you know, what are the benefits? What are the harms? What are the consequences, and piecing all of that, together with what I know and what I’ve learned? Through my executive career, what I’ve learned is some of the things that we’re doing with technology. So if we take things that we’re being fed, and we’re saying, okay, these are things that that can impact Black and African American communities, and then I know, these are the some of the things that you know, these technology companies are doing, I can bridge that together. And okay, now, how do we mitigate that? How should we think about it potentially, in a different way? Or for these communities? How do we make sure that we are building this technology with these communities in these marginalized communities in mind first, rather than building the technology, and then going back to our checklist and say, Oh, does it work for these communities?

Jeremy Burrows 31:10
Great. Well, there’s obviously a lot that we could talk about, I’m not going to take your whole evening. Appreciate your time. I do want to wrap up, though, with one question related to leadership, and specifically authentic leadership. And I wanted to ask you this question. It’s kind of a variation of a question that I asked many of my guests. And the question is generally what makes an assistant a leader. But I want to ask a little variation of it. And what makes an assistant and I authentic leader?

Leigh Felton 31:52
I love that question. And I don’t know, maybe you piqued my mind, LinkedIn, I think I have my youtube channel on there, where I, my heart is with authentic leadership. And I know we’re out of time. But this is something again, I guess it’s my third, you know, big area that I could talk forever, about, about four and a half years ago, I took my own mask off, and decided I’m going to show up as myself, because other people need to see that you can come to work, that how you got to this place in your career was because of the talents that you bring to the table and that you can come to work as your authentic self, and still have those talents. And still command and demand respect for those talents. And so, so it’s it is definitely a topic that’s very close to my heart. And I would say for an EA, first of all, it goes back to understanding your voice. What is it that you bring to the leadership team, there’s a completely different perspective, a completely different vantage point that you offer, that no other LT member has. So first and foremost, know your voice, know, the value that you bring, and then shore up an understanding. So let’s say your voice is understanding, you know, the full, the full EA and you know, all of the events and activities or whatever, be able to represent that get to the point where even if you’re just testing it at, you know, just for the leadership team, or to the CEOs, you should have such a comfortable relationship with the CEO that most likely you’re okay with having that conversation. But I’m talking about where you have a voice at the collective leadership team, and being able to test and say, Hey, actually, so we’re talking about our number five OKR, being about people. And we really need to what I’ve heard, and some of the other admins and I have talked about is that there’s some low morale because of XY and Z. And so maybe one of our KPIs could be around, you know, that you have such great information. And it’s about finding your voice and bringing that and being comfortable. Truly saying I actually am an expert. And you are, don’t let anybody tell you you’re not you are you are an expert, and just finding your voice and being able to represent that to the other leaders in the organization.

Jeremy Burrows 34:23
Well said, great way to wrap it up. Leigh , thank you so much again, how can people reach out to you if they want to learn more? And obviously, I’ll put the links in the show notes. But what’s the best place for people to reach out?

Leigh Felton 34:37
Well, I’m just getting started on my YouTube channel about authentic leadership. And so it is it slow, it is slow. And so I would love for people to subscribe to my YouTube channel. That’s at Leigh Felton on YouTube. And also, if you could follow me on LinkedIn, I think hopefully there’s additional wisdom and advice and you know, other things that that we can share.

Jeremy Burrows 34:58
Perfect, we’ll all find and all those links and put them in the show notes and leader assistant.com/two to five leaderassistant.com/225 thanks again Leigh. Best of luck to you and let’s definitely stay in touch lots of more conversations to be had about AI and chief of staff and in all the things so appreciate you spending time with us this evening.

Leigh Felton 35:21
Thank you so much Jeremy. This was a lot of fun

Unknown Speaker 35:34
pleased to have you on Apple podcast

Unknown Speaker 35:43


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