Conor Sweeney is Principal and Chief of Staff to the Cofounder and CFO at Box, Inc. (BOX) where he oversees business operations, executive communications, and strategic program management across the Global Finance & Operations organization.

Conor Sweeney Box Leader Assistant

In this episode, Conor shares one of the best overviews I’ve ever heard on what a Chief of Staff actually does. He also shares a bit of his story on how he ended up as a CoS, how he partners with c-suite assistants, and how assistants who aspire to be a CoS someday can prepare for the role.

For more resources on the Chief of Staff role, check out


SwipedOn is the fastest-growing visitor and employee management software. With tools like contactless sign in, visitor screening, and evacuation management, SwipedOn can provide the peace of mind every assistant – and their team – deserves.

Swiped On Leader Assistant Sponsor

So the next time you hear, “What’s your plan for the office as we return to work?” or “How will the hybrid workplace look for us?” you can respond confidently, knowing SwipedOn has you covered.

To learn more or sign up for a FREE 14-day trial, visit* today, and when you’re ready to move forward, be sure to use my exclusive discount code; LEADER20 for 20% off their annual plan. (*This is an affiliate link.)


When you say ‘yes’ to others make sure you are not saying ‘no’ to yourself.

– Paulo Coehlo


Conor Sweeney Leader Assistant Podcast Chief of Staff


Conor Sweeney is Principal and Chief of Staff to the Cofounder and CFO at Box, Inc. (BOX) where he oversees business operations, executive communications, and strategic program management across the Global Finance & Operations organization.

Prior to Box, Conor served as Senior Manager, Executive Communications and Head of People Communications at Walmart eCommerce where he partnered with the Chief Financial Officer and Chief People Officer to develop corporate communications strategies across the HR, Finance, and Corporate Development organizations. Sweeney also served in a variety of business operations and change management roles at Hewlett Packard Enterprise.

He holds a B.S. in Business Administration with a concentration in Marketing and happily resides in the Greater Los Angeles area with his wife.


To learn more about how you can join the now 200+ growth-minded Leader Assistants, check out our Leader Assistant Premium Membership for ongoing training, coaching, and community.

Leader Assistant Membership Circle Screenshot Welcome APR 2021


Check out our constantly updated schedule of events for admins and assistants at


Download the first 3 chapters of The Leader Assistant: Four Pillars of Game-Changing Assistant for FREE here or buy it on Amazon or Audible.


Join the Leader Assistant Global Community here, or the Facebook Group here for bonus content and to network with other assistants who are committed to becoming leaders!


Subscribe to The Leader Assistant Podcast so you don’t miss new episodes!

You can find the show on Apple PodcastsSpotifyGoogle Podcasts, Pandora, and Stitcher.

Join my email list here if you want to get an email when a new episode goes live.


If you’re enjoying the podcast, please take 2 minutes to rate and review the show on Apple Podcasts here. Each review helps me stay motivated to keep the show going!


Conor Sweeney 0:00
Hi, I’m Conor Sweeney and today’s leadership quote is courage is what it takes to stand up and speak. Courage is also what it takes to sit down and listen. Richard Branson

Podcast Intro 0:13
The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, Game Changing leader assistant.

Jeremy Burrows 0:24
Thank you for listening to The Leader Assistant Podcast assistance our workplace heroes, and as such transitioning safely and securely from remote work to an in office environment is top of mind. And we all know that every superhero needs a sidekick. Enter today’s sponsor swiped on. swiped on is the fastest growing visitor and employee management software with tools like contactless sign in visitor screening, and evacuation management swiped on can help provide the peace of mind every assistant and their team deserves. So the next time you hear what’s your plan for the office as we returned to work, or how will the hybrid workplace look for us, you can respond confidently knowing swiped on has you covered. To learn more or sign up for a free 14 day trial visit that’s And when you’re ready to move forward, be sure to use my exclusive discount code for 20% off their annual plan. The discount code is leader20. That’s leader20 for 20% off their annual plan. So reopen your business safely today with swiped on. Hey friends. Thanks for tuning in to The Leader Assistant Podcast. It’s your host Jeremy Burrows. And today I’m super excited to be speaking with Conor Sweeney Conor is the chief of staff to the co founder and CFO at Box Conor how’s it going?

Conor Sweeney 2:15
It’s going really well. Jeremy, thanks for having me. I’m really excited to be here today.

Jeremy Burrows 2:20
And tell us a little bit about box and who box is for those who haven’t heard of it?

Conor Sweeney 2:28
Absolutely. Yeah, so box is a cloud content management platform. We are headquartered in the San Francisco Bay area. We’ve been a public company for close to seven years now. We have about 2500 employees worldwide. And you know, we’re really excited to continue to power how the world collaborates. And I know for me, it’s a really amazing organization to be a part of so

Jeremy Burrows 2:56
great. And how did you end up at box?

Conor Sweeney 2:59
Yeah, so I’ve been with box now for close to two years. And I had a mentor of mine who actually is still with the company who who helped to kind of bring me in, I was really looking for a change in career and focus and was looking to make an external jump. And there was an you know, this opportunity came about at a really great time. And so it was a mentor and friend of mine that that brought me into the organization. And funnily enough, she and I worked very closely today. So it’s funny how things work.

Jeremy Burrows 3:34
Yeah, that’s awesome. All that who you know, right?

Conor Sweeney 3:37
It’s definitely a big part of it. Yes.

Jeremy Burrows 3:41
So okay, so tell us, we’re gonna, we’re gonna get into the chief of staff role. There’s a lot of talk, especially in the executive assistant world, you know, about what exactly is a chief of staff? Is it a natural progression from, you know, the executive assistant position, and, and so on and so forth. So we’ll get into that in a second. But why don’t you tell us a little bit about yourself? Where are you from? And maybe one interesting fact that we should know about you?

Conor Sweeney 4:19
sound sounds great. So I was born and raised in New England. In the beautiful state of Maine. I spent the first 22 years of my life in Southern Maine and actually went on to do my higher education undergraduate degree in Maine. And right after graduating from college, I made the decision to move out to beautiful California. I was really eager very early on in my business studies to take on a career in the world of technology. And that mixed with just really optimizing for some warmer weather is what ultimately brought me out to California. I started my My career, Jeremy with hp, and was with HP for close to five years, the first five years of my career. And from there went on to spend some time at Walmart and then from Walmart, and now here at box. And so I’ve spent, you know, a majority of my seven plus years as a professional in the world of technology, and have been here in California for the last seven years as well. And not too long after I moved here, I met my beautiful wife, who was a California native and now she and I at the moment are kind of nomads. We’re both professionally based in the San Francisco Bay area. But like many we’ve been working remote for over a year now. And we’ve been down here in Southern California just spending more time with with family.

Jeremy Burrows 5:49
Awesome. So what’s your you and your wife’s favorite? Kind of travel activity? Like hiking, biking? Do you like skiing? What do you guys like to do?

Conor Sweeney 6:02
We have very different perspectives on this, which is funny, they say opposites attract, and I couldn’t agree more. You know, for me, Jeremy, one of my biggest hobbies is actually wine. I spent a lot of my free time reading up on wine, kind of studying wine, taking classes on wine. And of course, living in California, it’s a great place to be for wine lovers. So we do spend a lot of time out in the vineyards, tasting wine. So, you know, for me when we travel. And that’s relevant, because you know, I’m constantly optimizing for that downtime, right? Like, how can we just relax, you know, kick up our feet have a glass of wine, whether it be on the beach by the pool on the mountain. But my, my wife is a lot more adventurous than I am. She loves museums. She loves exploring. And so we have a really good time and we’re on vacation, kind of bringing those two things together, it’s usually a very well rounded trip. By the end of it, we’ve gotten in the relaxing part, the you know, the sipping wine by the pool part. But But again, she’s definitely more exploratory than I am. So it’s a total opposite approach to to vacations, but we make it work and we have a lot of fun doing it.

Jeremy Burrows 7:16
Nice. And I love that. You said wine is your hobby. And I didn’t even know that was a hobby. You could technically call wine a hobby. But that works. Some people would call wine. A problem, but you call it a hobby. I love it.

Conor Sweeney 7:29
Yeah, yes, absolutely. Well, you know, it took living in a place. I mean, having grown up for the first 22 years of my life, in New England, where you know, the the world of wine is not nearly what it is in a place like California, where you’ve got the Napa Valley and Sonoma and all these, like incredible wine regions. It’s just really, really fascinating. And for me, I actually have a cousin who works in the wine industry is a sommelier. He’s a certified wine expert. And he works at country clubs. And he’s a wine educator. And it really took spending a lot more time with him to come to appreciate it a lot more than just wow, this tastes great. And it’s a great way to kind of decompress at the end of the day, because there’s so much history and science, specifically chemistry, you know, around wine. And so just kind of the diversity of the topic and mixed with the fact that you know, I enjoy the taste of it, it’s become a real hobby of mine.

Jeremy Burrows 8:24
Nice. Love it. Love it. Love it. All right, well, let’s get in to kind of the meat of the episode. And now that we’ve had our wine chief of staff, so how did you end up as a chief of staff? And is it something or a title even that you aspired to or wanted to do? Or did you just kind of fall into it?

Conor Sweeney 8:47
Yeah, so I guess to answer the second part of your question first, yes, I knew very early on in my career that this was a tour of duty that I wanted for myself. I actually remember the moment. It became very real for me. A couple of years into my career. at Hewlett Packard Enterprise. I was on a business trip in Las Vegas for a big customer event that they were hosting and through a colleague, I was introduced to a gentleman named Brad Harwell. And just for the mention, I hope he listened to this episode, who at the time was the chief of staff for HPE North American enterprise group, which was a 5 billion yes billion with a B, dollar organization. Right. This was a huge role. And Brad had actually spent much of his career as a marketing and go to market executive within Compaq and then later for a number of years with HP prior to stepping into this role and it was spending time with him throughout that week in learning more about his world that really made me want this for myself at some point. It’s everything from what he had exposure to what he was learning During the relationships that he was developing, all of it was just super fascinating to me. And, you know, also mentioned that I’ve always had a keen interest in leadership, and specifically the correlation between leadership and organizational performance. And, you know, aside from being a senior leader, or having a seat in the C suite myself, you know, this was a role and is a role that provides kind of one of very few ways to see all of that come together. You know, I’m also someone who aspires to sit in a senior leadership role at some point, and what better way to learn the ropes than, you know, to partner with those that are already there. You know, chiefs of staff get a very unique opportunity to not only see all of the moving pieces at a 30,000 foot view, but, you know, really get to watch leaders maneuver, maneuver through that environment, which is truly, you know, kind of, for me, I wanted to a million opportunity. And so I always tell people, there’s really no better leadership accelerator than than this role. And to kind of answer the first part of your question as far as how I ended up here. You know, I’ve spent the majority of my career Jeremy straddling the line of business operations and corporate communications. I mentioned earlier, I spent almost five years of my career at Hewlett Packard Enterprise I spent spent the first few years as a business operations analyst, you know, later moved on to become a business operations manager, working across organizations such as global procurement, global real estate, it really kind of across the majority of of some of the more technical functions, you know, kind of within the finance world at HP. My last gig at HP was actually with the global real estate group, where I had this amazing opportunity to lead a portion of the company’s West Coast real estate operations team, which is what geographically brought me to Silicon Valley in the first place, and kind of beyond my years at HP and really focus on all things ops and strategy. I then went on to spend some time at Walmart working in their e commerce business and had this very unique opportunity to lead all aspects of executive communications for their kind of Chief HR officer and global HR organization, as well as their corporate development organization, which was, at the time going through a lot, there was a lot of m&a activity on the E commerce side of Walmart when I was there. And so it was a real phenomenal opportunity, in general, and I had a amazing amount of exposure to some really incredible senior leaders there. And as you mentioned, at the beginning of now, a box where, you know, principal and chief of staff for their global finance and ops organization and, you know, have the distinct honor and privilege of partnering very closely with our co founder and CFO, and really kind of run all things from Biz Ops, to communications and program management for, for his organization. So a lot of what brought me to this role is one, just the eagerness of knowing I wanted to step into this world at some point and kind of get this perspective at some point. But to my background kind of lent itself very uniquely to, you know, what chiefs of staff do.

Jeremy Burrows 13:20
That’s great. So that’s a perfect segue to my next question. In one or two sentences, you kind of use a few more sentences to describe a little bit of it just now. But in one or two sentences, can you describe what a chief of staff does?

Conor Sweeney 13:37
Yeah, so look, chief of staff, chief of staff are dot connectors, skilled operators, and problem solvers, that partner with senior leaders and or larger organizations to drive oftentimes at scale, efficiency and effectiveness, solve challenges before they become bigger problems and create and maintain relationships that ultimately help to keep the engine running right, the engine of the organization you’re supporting or the business at large. A chief of staff is often the right hand to a chief executive, and serves as a I like to call it a key multiplier for that chief executive and their their leadership team.

Jeremy Burrows 14:23
So to break it down into three buckets, like your LinkedIn summary does. You had kind of three categories business operations, strategic initiatives, and executive communications. Can you share maybe a quick example of what your day to day looks like in each of those three areas?

Conor Sweeney 14:48
Yeah, absolutely. So, you know, every day and I mean, every day is different in a role like this. And I think starting with the biz This operations bucket, this is a really interesting area that for many companies is gaining quite a bit of steam right now, right, you see a lot more organizations that are standing up dedicated business operations functions. Those functions oftentimes include kind of a hodgepodge of it could be, you know, business analytics data science program or project management. So it’s a very interesting world. And much like the role of chief of staff a bit of a nuanced one at the moment. But for me in my role, this is where the efficiency and effectiveness comes into play. So business operations for me, you know, on a call it month to month, quarter to quarter basis is everything from working with corporate finance to lead and drive our annual strategic planning process, or managing and owning our organizational level OKR process to partnering with my boss’s leadership team to drive accountability around our workforce and location strategy. So much of business operations is about driving key initiatives that are connected to keeping the organization healthy, so to speak. So delivering on our strategic commitments when we say we will, holding ourselves accountable to you know, large scale budgets, etc, etc. Executive communications is an interesting one for me, as I alluded to briefly earlier, I came into this role with some really unique experience. Having worked with sea level leaders at a fortune one retailer, from a pure play communications perspective, I saw the impact that communication strategy can have on a complex, fast paced organization. So I was really eager to aggressively weave that into my remit as a chief of staff. And for what it’s worth, you know, communications, for most Chiefs of Staff is part of the remit, and in a variety of different ways. It could be external, internal, both. But for me, kind of having come into the role with that experience, I was very eager to kind of weave that in in a very specific way. And, you know, specifically executives comms leadership in this role is partnering very closely with my principle leader to ensure there’s consistency in how and what he and his leaders communicate within their organizations. And also consistency and how top down and bottoms up messaging come together in a very productive way. You know, chiefs of staff are most importantly, culture carriers for their organization. So it’s important to have that ear to the ground mentality, and have that play a big role in how and what a leader is communicating at any given time. And lastly, on the strategic program management, strategic initiative, leadership, you know, whatever you want to call it, this, this is really taken, oftentimes, large, complex, messy projects that don’t always have a home in the organization, and bringing them across the finish line, you know, program, project management, it’s a huge part of any chief of staff role. You know, I’ve personally in this role worked on everything from helping to stand up various phases around our company’s location and Workforce Strategy to putting specific frameworks in place to track our free cash flow progress against our targets and commitments that we’ve set to partnering with leaders across the company to drive progress around the reopening of our offices in a post COVID world. This is where really where I see the most diversity in my role. And, again, it’s important to call out that, you know, oftentimes, the projects or initiatives that chiefs of staff work on are, they’re critically important to leadership, but oftentimes struggled to gain momentum due to the lack of organizational ownership. So, you know, in this situation, and for most chief of staff, you’re expected to come in, you know, break down those barriers, and ultimately, just find a way to get stuff done, and forge partnerships to do that in an environment of uncertainty. And so that’s, that’s kind of how I break down those those three buckets.

Jeremy Burrows 19:08
And that’s great. It’s like, super, super helpful. There’s so many assistants that reach out asking about the chief of staff role, and I’m excited to share this episode with him because you just summarized it greatly. So thanks for doing that. So how do you partner with assistants, specifically C suite assistance at box in your role?

Conor Sweeney 19:33
So it’s a great question. And, you know, I’ll start by saying and, you know, while there’s absolutely some adjacency in these roles, right, kind of the the EAA and the chief of staff, as far as stakeholder management, and the commitment to a senior leader, the roles are quite unique and quite different from each other. Right. And, you know, to me, the biggest differences boiled down to, you know, time and responsibility The now slash in the moment versus the kind of future moments, the Tactics versus the strategy, but, you know, different topic for a different time. But, you know, my bosses EA and I are tied at the hip. Jeremy, we agreed, very early on that a successful partnership between the two of us was critically important to the success of the org and our leaders. You know, as much as I want to say that there’s a secret magical sauce to this partnership. And for some, there may be, you know, for me, there really isn’t like any business partnership framework. You know, respect trust, and knowing when to stay in your own lanes is really important, and creates the environment for a very successful partnership. So yeah, I again, kind of the way that I work with C suite assistants at Box is in a variety of different ways they can be very, very helpful in certain programs are projects that we’re trying to push across the finish line, their perspective on just the amount of time, right that a leader has to dedicate to certain things is, is a very, very unique and necessary perspective for us as chiefs of staff to have as we’re trying to align kind of time allocation to what it is strategically that we’re focused on as an organization. So, you know, I’ve had the philosophy since day one of this role that, you know, the the partnership, the EAA chief of staff partnership is really, really critical to the success of any organization that has the two roles that are coexisting.

Jeremy Burrows 21:32
So I just got on a got off of the coaching call this week with an assistant who is in a new role and is working with a chief of staff that to be frank is just kind of at a lower level than the system is. And she’s really struggling with like, Okay, how do I not just step in and do their job, but also kind of help help them grow? And, you know, there’s just, there’s just an interesting dynamic, when you step into a role they’re supporting the same executive and chief of staff is, is new to the, the three, three point triangle, if you will, any suggestions to those assistants listening who may be struggling with that relationship and partnership? Between the chief of staff?

Conor Sweeney 22:36
Yeah, it’s a really interesting question. You know, I think for your specific example, what’s what’s most interesting is, most chiefs of staff are, are new to their role, right. So if you think about, like the evolution of the chief of staff role, it’s, it’s oftentimes not a role that’s optimized for somebody to be in it for a really long period of time, right, chief of staff roles are kind of most commonly, I hate to call them rotational roles, but there’s usually kind of like a two to three year shelf life on the role, because oftentimes, the person that stepping into that role is stepping into that role for, you know, a pretty specific reason to develop skills in a certain area, to kind of forge partnerships, to then kind of go on to the next thing. And so, now, I’ll say that kind of the nuance there is, is that I personally do know, you know, some chiefs of staff that have been chiefs of staff more than once and I have the utmost respect for them, because I don’t know how they mentally and physically do it. It’s for me one of those roles that you know, you do it for a few years, and you exhaust yourself and you take in all the you can, and then you kind of move on. So I’ll say kind of back to my original point that most chief of staff are coming in, relatively new to the world of being a chief of staff. Right. And it’s can absolutely be challenging, I’m sure for executive assistants who have been with an executive for maybe a much longer period of time, or have, you know, been working in the EA world for a lot longer than that chief of staff has been working in the chief of staff world. But I again, I think it really all comes down to kind of, you know, partnership, communication and intention. Right. So, you know, one of the things that I was really clear with my boss I want to come into this role is, why did you hire me, right? What are the things that you’re optimizing for? That I can help kind of drive across the finish line, but I can help accelerate, right. And so I think it’s really important and you kind of alluded to a triangle earlier, but when I think about like a principal leader, and executive assistant and chief of staff, there needs to be a certain level of alignment between those three around who’s doing what, why they’re doing what, and ultimately like, what what the goals are, right? There needs to be a sense of leadership advocacy, in the upfront to really help set the tone for what will hopefully be a very success. A relationship between the chief of staff and the EA. So I would challenge the EA in this particular example, as someone who sounds like has a bit more experience with the company organization leader to, to really do what they can to kind of liaise, that sense of what is it that the senior leader is looking for? What is it kind of in my world, and with my experience that I can do to help this chief of staff be be successful, I would challenge that EA and that chief of staff to spend a lot of time in the upfront, developing kind of parameters and criteria around their partnership framework, right? Who’s doing this thing? And who’s doing that thing, right, as it relates to kind of like staying in one lane versus the other, like, getting very, very specific around who’s doing what, so that there really isn’t any murkiness or question marks around, you know, kind of, again, that that broader partnership framework, so I, you know, kind of long winded way of saying, you know, collaboration, communication, and then that leadership and advocacy from the senior leader is really for me, I think, kind of the the ultimate trifecta for, for driving a successful partnership, especially between those two roles.

Jeremy Burrows 26:13
Yeah, that’s, well said, well said, and I, you know, it’s, it’s interesting, because the, you’re talking about trust earlier, and just kind of the communication between the roles, and then clarifying the expectations is such a huge thing. Like, I was talking to a different assistant several months ago, and she was like, you know, when we started, we being the executive, the chief of staff in this system, when we started working together, we didn’t clarify the roles and and make it extra clear on who was supposed to do what and so they’re, they’re the chief of staff and the assistant, we’re stepping on each other’s toes, like all the time. And you really just have to nip that in the bud early on and and get that clear, just like you said, so.

Conor Sweeney 27:02
Yeah, well, I think, you know, there, there is, in my opinion, a duty of the principle leader to really be very intentional about what he or she is looking for in the roles, right, specifically, the chief of staff role. You know, as I alluded to, briefly earlier, as it’s gaining a lot of momentum right now, I mean, it’s a really hot role for a lot of companies for a lot of different reasons. And what I see is a lot of leaders saying, Well, I want to chief of staff. And here’s kind of some high level buckets of the things that I’m hoping my chief of staff can accomplish. But that’s kind of where the car stops a lot of the times, right, there isn’t that kind of next level of intentionality with what are some of the things I really want this resource to do? And drive? And what are some of the partnerships that I’m, you know, that are really important for this role to kind of Forge throughout the journey of the role. And so, you know, I’ve I challenge all senior leaders to be very, very intentional, and to be very thoughtful when kind of hiring for these roles. Because, you know, in a, in a great situation where you have that alignment, and you have your kind of lean set, and your bucket set and your you know, Ideas set, it can be one of the most amazing, effective and efficient partnerships, ever. But when you don’t take the time to really drive that level of advocacy with the leadership team and drive that kind of, you know, dock connecting between the EAA the chief of staff and leader like, that’s where things can get really challenging and very murky, and I’ve seen it a lot. I hear about it a lot, as I’m sure you do as well.

Jeremy Burrows 28:38
Yeah. Yeah, there’s a lot of gray areas in the role sometimes and even just even just between, you know, high level senior executive business partner slash executive assistants, often kind of moves on to my next question, often, you know, and I’m sure I’m 100% positive that as you were explaining the chief of staff role, there were probably dozens, if not hundreds of assistants, whose ears perked up and were like, wait a minute, that’s what I do. Like, wait, am i chief of staff but because there are a lot of executive assistants who functionally are our chiefs of staff. And so anyway, I don’t know if you had any thoughts or tips on you know, if if an assistant already does all the stuff that you’ve been talking about, but they for whatever reason, their executive or their company, either they’re afraid of the of the word chief in chief of staff, or they just don’t want to give them that promotion or compensation bomb. What would you recommend those assistants who are like me and I do all this? I do. I have the executive communications back In the strategic initiatives, OKRs and business ops, but I’m not getting that respect or they won’t give me that that title, what would you say to those listening that are in those in that position?

Conor Sweeney 30:14
Yeah, so I think specifically, over the last few years, there has been a phenomenal amount of research content, etc, that has become available to the broader population that really helps to effectively break down the role of chief of staff and the way that chief of staff can drive business impact on an organization. And so because there is so much more accessibility to kind of what the role is how it can drive that impact in your organization, and more specifically, the delineation between an EA and chief of staff, there really isn’t an excuse for that anymore, in my opinion. So it sounds harsh to say, but, you know, if you’re in a situation where you’re an executive assistant, and you’re kind of doing all these things, and you’re kind of optimizing for that title, and that promotion, and that, that kind of just holistic chief of staff package, which you’re not getting, it’s probably time to move on at that point. And, as I’ve mentioned, while there is some adjacency, to these two worlds, the roles themselves are significantly different. And, you know, under no circumstances is it okay to be doing a completely different job than that of your title slash what you were hired to do. And, you know, if someone was hired as an FP and a analyst in the finance world, but, you know, kind of later came to the conclusion that they were doing the job of a manager, you know, in the investor relations world, you’d either reclassify yourself as a manager in the investor relations world with your management, or you probably find something else, right. I mean, this is exactly the same thing, because there’s definitely adjacency between, you know, what an FTA analyst and somebody in investor relations does the adjacency, there’s that they’re both finance driven roles. But they’re very, very different as far as what they’re focused on, and what they’re driving and kind of strategically what the remit is. So, you know, I know that situations like this aren’t always so cut and dry. But I do think it’s important for chief of staff EAS and leaders to kind of all understand equally, that by design and intention, the role of an EA and the role of the chief of staff are very different roles. And so to me, this is almost a call. And this is kind of piggybacking off of my last name and statement to all senior leaders to ensure that there is intention when you’re hiring for chief of staff and EAS, and that there’s a fundamental understanding of, you know, what the two roles can execute, you know, for you and your organization based on, you know, kind of the remit of the roles. So, you know, I know, I answered this in a pretty black and white kind of way, as far as like, hey, you know, this is an ongoing struggle, it’s time to take a hike, and maybe go check something else out. But, you know, career development is a major passion point for me, and no one’s looking out for your career development more than you are. And so, I know these can be very challenging situations. But sometimes you have to cut your losses, if you’re finding that you’re not getting the momentum that you you should, in my opinion, in a situation where there is clear delineation between the two roles.

Jeremy Burrows 33:28
Yeah, and what you said about the there’s more resources now that are available to anybody that can clearly delineate between EA and chief of staff. So that should help assistants in this position. You know, put together that business case, and then yeah, I agree. I mean, it’s, it’s obviously scary and challenging to try to just leave your job and find another one. But if you’re doing a role, like you mentioned, if you’re doing a role that you’re not being fairly recognized and and compensated for then yeah, it’s definitely time to move on. Alright, so what if you’re an assistant listening and you’re like, I want to be able to do all that. I strive to do all that what’s something that assistants can do to prepare themselves for the chief of staff role someday?

Conor Sweeney 34:27
is a great question. I tend to follow my current roles framework when answering this question, kind of leveraging that communications Biz Ops program management bucketing that we talked about a bit today. You know, I think developing yourself within a variety of different skill sets is really one of the best things you can do to prepare for this role or any role, right. So I think specifically the chief of staff role and kind of breaking it down in those buckets first, you know, I’ve mentioned this having some communications chops in is key to the success in a chief of staff role, right I was I would go as far as to say that this is the most important skill to develop, and one that I utilize the most. It’s everything from working with senior leaders to craft compelling narratives around business critical initiatives to taking highly complex ideas and distilling them down to simple digestible concepts to being able to effectively and efficiently communicate an idea or an initiative to every type of audience. Communications is everything in this role. And you know, I alluded to the term dock connector earlier, as the chief dock connector of your organization and a chief of staff role. We can’t connect the dots if we can efficiently and effectively communicate. So any opportunity to develop these skills through public speaking opportunities, or kind of comms coursework, etc, I think is really, really important and, you know, beneficial to everything right? Not just, you know, you optimizing for a future chief of staff role. But, you know, communications really makes the world go around a lot of ways. You know, secondly, having, as I mentioned earlier, having significant project and program management experience is incredibly important for anyone looking to step in to this role, not just for the obvious reasons of wanting to ensure that you’re comfortable with various, whether it be project management frameworks, working styles, etc. But also being used to working with every type of stakeholder across a business, which PMS oftentimes do, right? There’s kind of that political nature to the world of program project management. So being able to effectively stand up a process a system, a policy, with the help of a variety of different business profiles, whether that be you know, engineers, going to market folks, it folks, finance professionals, etc. This, to me has always been one of the biggest challenges for project management, right is the ability to bring people with different types of business backgrounds together to the table to accomplish a centralized effort. So any experience one can get contributing to or leading projects is usually important now, whether that be through coursework, getting a PMP, or, you know, taking on stretch projects in the organization that you’re already in to really kind of build up on those program project management chops. I mean, I would say that that’s, that’s very, very important. And lastly, on the biz ops front, it’s, it’s hard to boil this down into various things, you know, to channel in preparation for a role like this, but I’ll say that the ability to analyze data, and quickly make decisions based on what that analysis is, it’s really important, right, as an extension of the leader or leadership team in a strategic capacity in a chief of staff role, it’s important to do your best to know as much as they know. And in certain situations, no more so that you can provide that sometimes very necessary strategic advisory, to avoid potential challenges down the road. So net net skill development, Jeremy is very, very important in in preparing for a role like this. And I think thankfully, you know, if you’re sitting in a large organization already, or have access to, you know, a variety of different business backgrounds and partnership, framers, etc, you can oftentimes take advantage of that to take on stretch projects, or get sponsorship to do different certifications, programs, etc. But I think skill development is really key here.

Jeremy Burrows 38:25
Would there be maybe one or two, either books or courses? Or, you know, you mentioned the PMP. But is there any, like maybe your favorite book or resource to help that’s helped you in your development for this role?

Conor Sweeney 38:45
Yeah, so I’m a huge proponent for professional development organizations. So when I first stepped into this role, I joined an organization called the the chief of staff network, it was formerly called the chief of staff Tech Network, is now called just the chief of staff network. And it’s essentially a grouping array of chiefs of staff across the technology industry, from all around the world that work in, you know, all different sized companies, startups to medium enterprises, etc. that that kind of get together to drive knowledge sharing and share tips and tricks and tools and processes and frameworks. And, you know, I was part of the San Francisco Bay Area chapter and kind of pre COVID The chapter would meet every month at a different person’s office, right? So one month I would host you know, the the meet up at box and, you know, another months it’d be maybe over at chime or Brightwheel or, you know, wherever it was, and just sitting in a room with other people that are in this very unique position was incredible. And there was so much that I took from that experience and was able to apply to it. What I was doing and what I am doing on a day to day basis, right. And so I think for me, I get a lot of benefit from, you know, professional development organizations and meetups and talking with like minded people that have similar goals, similar interests that work in very similar environments. I think that’s, in my opinion, where a lot of the magic happens when it comes to learning, and developing. I’ll be honest, I’m not a huge reader. So I don’t have like a specific book or tool or system or what have you, that has been kind of incredibly life changing for me, but joining that organization, and getting access to tons of individuals that are in the same exact position as me and very similar industries and very similar environments. That’s where I’ve, I feel like I’ve grown 10x Over the last couple years.

Jeremy Burrows 40:50
Yeah, you know, the community aspect is such a big, big part of, and I think probably one of the most important parts of professional development. So that’s great. And those who are listening, you know, chief of staff network does have some public blogs and resources. So if you’re not a chief of staff, yet, you can still learn from their sites, I’ll put that in the show notes. Alright, so Connor, it’s been a great interview, I just want to wrap up real quickly, what’s your favorite part about the role?

Conor Sweeney 41:26
So I alluded to this a little bit earlier. But to circle back, for me, it’s the education factor, you know, in a role like this, you’re oftentimes partnering with and learning from the most influential and senior leaders in any organization. And so you know, chiefs of staff have a very unique opportunity to see how all the pieces come together at an altitude that’s normally reserved for the C suite, right, and senior leaders. And so, you know, I mentioned earlier I mentioned it again, I firmly believe that this is one of the best leadership accelerators out there. I’ll also mention that, and there’s pros and cons of this, right? This is what I love about the role. But sometimes what I don’t love about the role is no two days are the same. It keeps the job really interesting, right? So, you know, you start to get into a rhythm of certain initiatives or tasks on a quarter over quarter basis, or weekly basis or what have you. But at the end of the day, you’re really at the mercy of your environment. And that ambiguity is really exciting to me, I get a lot of strange looks when I mentioned that. But for, for better, or for worse, my entire career, Jeremy has been built around, jumping into really uncomfortable situations and making the best of it. You know, I’ll go on just kind of a quick tangent here, as far as what has inspired that point of view. But when I started my career, many years ago, at HP, I was at the company, maybe six months before the 80 year old 100 billion dollar legacy tech behemoth that most of the world had come to know as a very specific organization, brand, etc, announced it would be splitting into two separate publicly traded companies, which are today known as HP Inc. and Hewlett Packard Enterprise. So, you know, this newly graduated business operations analyst, right was really scratching his head wondering what the heck he had gotten himself into. And, you know, what I didn’t realize them but quickly came to realize after is how much good can come from change and transformation as far as opportunities and learnings. And, you know, working and living through one of, if not the largest corporate tech splits transformations in tech history has a lot to do with my desire to pursue organized chaos. And like my ability to like thrive in ambiguity and so, you know, kind of summary, it’s the education factor, you know, the exposure, but it’s also just the No two days are the same. And you really never know what you’re gonna get. And that, to me is very exciting.

Jeremy Burrows 44:09
Yeah, I love I love the EAA role as well, because, you know, there’s never a dull moment. And I just, I just love that I’m never bored in my job. Because I don’t know if I could do the job for very long if I was the same thing every day. So I can definitely appreciate that.

Conor Sweeney 44:28
Yeah, it’s a bit of a double edged sword for a lot of, you know, chief of staff I talk to where they they take on the role because they’re excited to have that, you know, no day is the same and working on a variety of different challenges and working cross functionally. But that can also become very exhausting after a while and so, then it’s also like, Okay, I’m ready to focus but then there’s that fear, to kind of focus on something specific because then you’re going to have that kind of like fear of missing out. I miss To the chaos and Mr. craziness, so it’s yeah, it’s the psychology behind. It’s very, very fascinating.

Jeremy Burrows 45:06
Well, Connor, thank you so much for being on the show. Is there somewhere that people can reach out to you and say hi, or connect and see what you’re up to?

Conor Sweeney 45:16
Absolutely, yeah. So, Jeremy, if you want to actually share the link to my LinkedIn in your show notes, if you do that, I’m more than happy to connect on LinkedIn. Certainly over the last year and a half, as we’ve all been kind of navigating through these very unique and challenging times, LinkedIn has become one of my absolute favorite tools. And, you know, I’ve developed some really amazing connections virtually over that time with people just kind of dealing with this ambiguity and kind of unique situation in very different ways. And it’s a platform that I think has, for the most part kind of stayed away from some of the, you know, political division, right, that we see on other social media platforms. And so, you know, I spend a lot of time on LinkedIn and really like what it does for people and the access that it gives people and so yeah, I feel free to reach out to me there. I’m always happy to connect a cup of coffee, a glass of wine, email, whatever it is, I, I’m all about it.

Jeremy Burrows 46:15
Awesome. Well, I’ll put that in the show notes for sure. And yeah, thanks again. Best of luck to you and your journey as a chief of staff, and we’ll talk soon.

Conor Sweeney 46:25
Absolutely. Thanks for having me again, Jeremy. Really appreciate it.

Jeremy Burrows 46:28
Thank you for listening. Check out the show notes at That’s Have a great day and we’ll talk to you next time.

Please listen you on Apple podcasts.


Download FREE Chapters