Leveraging Leadership

Lessons from a Long-Term Chief of Staff Partnership

• Emily Sander • Season 1 • Episode 211

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Jennifer Baron shares her 18-year journey working alongside her principal, Justin, starting as a temp cleaning a file room and eventually becoming Chief of Staff for a private equity firm. She talks about helping manage company growth, supporting multiple portfolio companies, and even working on a historic castle restoration in Scotland. Jennifer also offers practical advice for building a trusted Chief of Staff-principal relationship and setting healthy boundaries.


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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:

00:31 Discovering Family History
01:54 Jennifer's Career Beginnings
03:43 Meeting Justin and Early Career at Endeavor
05:23 Becoming Chief of Staff
10:03 Private Equity and Company Growth
16:30 Current Role and Responsibilities
19:08 Role of a Chief of Staff in PE Firms
20:43 Building Trust and Dependability
24:44 Evolving Together Over 18 Years
27:41 Adventures in Scotland: A Team-Building Experience
30:55 Advice for Aspiring Chiefs of Staff

Emily:

My guest today is Jennifer Baron. Jennifer, how are you doing? I'm great. How are you Emily? I'm doing all right. Thanks. I saw your recent LinkedIn post about your grandma and you found like old photos and she was a, what was it, a punch card operator?

Speaker 2:

Yes, like back in the sixties. Isn't that incredible? Doing her admin thing? Yeah. That's amazing. Yeah. I love those pictures. Um,

Emily:

yeah.

Speaker 2:

Right. And I have this connection with her that I didn't even know about until like two weeks ago, so That's amazing. Was that just out of a

Emily:

box from like someone's house of

Speaker 2:

photos? Yeah. Yeah, my grandfather's house. And we just went through everything and we found all kinds of amazing things. So that was very exciting.

Emily:

I love that. I love doing that. Where you find a whole box of photos.'cause it's not on a computer, it's actual physical photos. Yes. And it's like these photos tell a story, which Yes. You get to uncover. So that was super cool. And it's so funny'cause I saw the post and I thought it was. Like, you can see the family resemblance a little bit. I'm like, oh, yep, that's your grandma. Got it. Yes, yes. Um, fantastic. But thank you so much for joining. You have a really interesting chief of staff story. Uh, I think you win for the longest partnership with your principal, which is 18 years. Is it 18? That's correct. Wow. I'm

Speaker 2:

surprised. Like I didn't realize I was. Such, such a, an anomaly that's like with this tenure,

Emily:

a full adult person who can vote. That's, that's a long time. That's a lot of hairstyles, Jen. Um, yes, but I wanna hear about like your origin story, how you met Justin, how you got to be chief of staff, and, um, all of those good things. So kick us off from the very beginning.

Speaker 2:

Yeah, so I'd love to kind of go through the highlights of our journey together. Um, starting with, my story actually starts with failure, um, which is how I ended up meeting Justin in the first place. So, uh, I started as an administrative assistant in the mortgage industry right out of college, and I worked my way up to Loan closer, and then eventually manager of the closing department. But what I didn't know was that I was not ready to manage people. Um, so I was, ended up being a perfect case study for someone who's really good at their job and gets promoted, but then fails due to lack of leadership training. Um, so January, 2007, the financial crisis hits and I get laid off because of downsizing. So I'm back to square one, just a few years straight outta college. Um. So the things that I learned from that experience was I didn't wanna be in an industry as volatile and unstable as mortgages. So I kind of took that off the table completely. Um, and then I also realized that I was not ready to manage people, at least not at that point in my career. Um, so because of the financial crisis, job prospects at the time were not great. So I figured that my best option would be to sign up with a temp agency. I had done that during high school and it worked out really well for me. I had steady work, so I figured why not, you know, I was also looking for jobs, but that was kind of a stop gap. Um, so I got a call from the temp agency and they had an assignment in Alpharetta, which is a suburb, suburb of Atlanta, but it's about 40 minutes from where we lived. So I was thinking, you know, I really do need something to do, but I'm not willing to commute that far if this turns into something more lucrative. So I declined that and the next day got a call for a job about 15 minutes from our house. So I took that and this is the part of the story that I look back on and I wonder, did everything. Did the universe already have everything laid out for me? So I show up at my assignment and it's for an administrative temp position at Endeavor Telecom. Uh, in February of 2007 and Justin is the CEO of this company. So that's how we first met. I'm a temp in his office and my first assignment is cleaning up this file room that was just in complete shambles. Um, so. Organizing things is literally one of my favorite things to do. So I was like, yes, this is perfect. Um, you know, I got that task done quickly. Who doesn't love a great organization challenge, right? Um, so then they started assigning me other projects and within a couple months I agreed to stay on as a permanent administrative assistant. Um, so I was supporting multiple executives, project management, sales, and the accounting department, and I started to work more closely with Justin. So that is kind of the beginning of our story, starting as a temp and then agreeing to stay on as an admin with

Emily:

his company. That last part you said is like inching toward chief of staff land. I can sense it, I can feel it.

Speaker 2:

Okay. Not yet, but almost gimme a couple years. So, uh, that was February of 2007. By December of 2007, um, we decided that. Because I was working on more kind of executive projects, a title change was, was warranted. So my title became, uh, manager of Executive Initiatives. So I was driving projects that were, um, things that Justin and his business partner wanted to push through, but they were working on strategic stuff. So they just need somebody to kind of keep an eye on things and make sure things are staying moving with these projects. And with that, I started to become the voice of the CEO within the company. Um, so Justin started to trust me and he was willing to let me be his representative, which was really cool. Um, and around that same time, we had a big conversation where we basically agreed to kind of merge our careers together, um, and keep working with each other as long as it was a positive partnership. So. I was like, wow, this is incredible.

Emily:

Yeah. Wait, tell me more about that. You just like decided one day we're just gonna stick together for a long time, just depending on our different roles.

Speaker 2:

Whoa. Yeah.

Emily:

Yeah.

Speaker 2:

It's

Emily:

really

Speaker 2:

crazy to think back on now.

Emily:

What? What made you guys do that?

Speaker 2:

We work together so well. We compliment each other. He's the risk taker. I keep us grounded, you know, he's the dreamer and I'm the doer. Um, so it was just, it worked. You know what I mean? Yeah. And the thing that I was most appreciative of was that he kind of, he accepted me for who I was, um, which means. He valued my own nonsense approach. Um, he appreciated the fact that I was super focused on getting things done because I think it was exactly what he needed at the time. Um, and that I was an intelligent person, so I didn't have to hide who I really was to succeed with him, if that makes sense. So that made me feel very comfortable. Um. And you know, the, the story there is when you're allowed to be yourself, you're, you have a better chance of success instead of worrying about, you know what I mean? Like worrying about what situation you're in and how do you need to change in order to fit when you can be yourself. It's just easy and you can focus on getting things done and handling stuff that you need to do.

Emily:

I love that. I love that when you're fully yourself and it. That makes it even more complimentary to the other person. Like that's a good spot to be in where it's like, okay, I just need to like lean into what I am just already doing, my strengths, what I'm about. And that fits so perfectly within this case, Justin's strength.'cause he can be fully who he is. Go off and vision and dream and take risks. And that's just, that's, I love that. Okay. So that's kind of, so it's pretty incredible. Felt that, and were like, let's just do this thing together for a while. Yes. Okay. Okay. Because

Speaker 2:

when he, when he started Endeavor, he always knew, one of the things he loves to say is start with the end in mind. So when he started this company, he knew that eventually he would sell it. So he knew that there were bigger things that he wanted to do, and he wanted to kind of bring me along for all that stuff. So. Gotcha. Okay. It's pretty awesome.

Emily:

Now, are you officially chief of staff yet, or not yet? No, not yet. That's coming. Okay. But you're doing a lot of chief of staff stuff. It's like you're the voice of the CEO, you're doing the strategic projects. Okay. Exactly.

Speaker 2:

Yep. So as a company, endeavor was growing. When I first started there, we had about 30 employees. Uh, within a few years we had 130 employees. So. The need for the manager of executive initiatives position and eventually chief of staff resulted from this company growth. Um, I interface between middle management and the executives, and I always listen for important information that I felt that I should share with them because I. People felt comfortable with me. I was building relationships and they told me things that they probably wouldn't go to Justin's office and tell him. Um, so I was adding value there because I was hearing things that they wouldn't hear in the normal course of business. Um, and I also advocated for the managers and the staff, uh, to support initiatives that would improve operations. So if they came to me and said, Hey, we're having a really tough time with this new thing that we've implemented, you know, I'd bring that feedback to the executives and. Help to make something better for everybody. Nice. So, so now a couple years later, 2009, we start to talk to a private equity firm out of Miami, and eventually that led to a recapitalization in March of 2010. So, I mean, you know about due diligence, Emily, it's a big part of private equity. Oh yes. So they're doing their due diligence on, on Endeavor. Um, Justin's in all these meetings, he is got all these data requests, so I'm helping him scheduling the meetings and fulfilling all these requests that we've got. So everything checks out, you know, the recap goes through March of 2010. And even though I'd only been with the company for about three years at that point, I was there for that large growth phase. So I had a ton of institutional knowledge and I was able to help the whole process, you know, with all these things that I knew. Um, so two really cool things about the recap. Um, one of the things that this private equity firm likes to do is when they do a transaction, they offer employees a chance to buy into some equity in the company. And I had never done anything like that before, but a, a good number of the management team bought in and that was kind of my first taste of investing. We'd never done anything like that. It was very exciting. Um, and then the second part of that is that Justin, when they were, you know, writing all the documents, all the legal documents, he made sure there was a clause in there that he could bring me with him. Whenever he left the company. Okay. So he could bring one employee and that was me. Wow. So that just kind of, but you know, when we had that deal to work together, this was kind of the next step of that. Whatever he goes to do next, I'm gonna go with him. Got it. In writing

Emily:

in a clause. Way to go. Justin, there's your, there's a principle for you. Alright. Yes. Okay.

Speaker 2:

Um, okay. So let's fast forward a little, a few months. We're into the summer of 2010 and we've gone through this big recap. We're growing the company. And I'm continuing to function as ju as Justin's right person, right hand person. Um, and then I have a conversation with one of my friends that summer that kind of changes the trajectory of my career. So he's telling me about his new position at SunTrust Bank. Um, he was the chief of staff for the Enterprise Services, enterprise Delivery Services group at the bank. And he's telling me about all these responsibilities that he has and I'm like, wait a second. That's all the stuff I'm already doing. So the wheels are turning in my head. I'm like, what can I do with this? So I end up generating a proposal to bring to Justin and say, Hey, what do you think about me assuming the title of chief of staff? These are all the things that chiefs of staff do. I'm already doing like 85% of them. So he was immediately like, yes, this sounds great. I love it. Especially because with the recap. My role became external facing as well. So I'm talking to people outside of the company and Justin wanted to make sure that we were conveying my position as his right hand person. And when you've got a title like manager of Executive initiatives that we literally made up, when I took that title, everybody's like, we don't know what that is, who are you? But when you hear chief of Staff, you're like, oh. I see what's going on. Nice. So that, that was accomplishing a, a goal, a goal for me to accelerate my career, but also to represent the company with what I was actually doing and my role. So it was a win-win. Very cool.

Emily:

Yeah. And which is pretty

Speaker 2:

exciting.

Emily:

Yeah. And just like one call out, like that's really important when even internally when you need to, you have a large company and you wanna convey like. What you do. Mm-hmm. Having the title and, and being able to, my principal used to say like, I need you to be able to bring the thunder if you need to. And I was like, got it. So, yes. Um, but externally too, people can, can, it helps them place it. So I'm glad he did that for you. I'm glad you advocated for it and he did that for you, but gotcha. Yes. Cool. So now you're officially chief of staff.

Speaker 2:

Yes. Uh, September of 2010, I believe, is when all that happened. Okay. Um, so let's fast forward to 2012. Like I mentioned, Justin always knew that he was eventually going to exit the company. So we hire a gentleman who starts off as COO and then eventually assumes that the CEO role within the company. So at that point, Justin becomes the executive chairman and I'm supporting him still as chief of staff. Um, to, you know, keep an eye on things, make sure that the new CEO has everything that he needs to be successful. Um, and we were able to start thinking about kind of what's next. So we, he wanted to open a private equity firm and family office, so I was like, yes, I'm on board. Let's do it. Um, and when we eventually do, you know. We're doing private equity full time. We talked about changing my title because at that point it wasn't a large company anymore. It was a very small office. Um, but he was like, no, we're gonna keep it because it, we still need to convey what your position is. So I appreciated that. I would've been fine with whatever, but. He said, let's keep it, you know, this is great. We'll just move forward with this. Um, so fast forward a couple more years. Endeavor merges with a company called OnePath and it formed a company of several thousand employees. So at that point we would go from 30 to like 150 to like several thousand, which was mind blowing. Um, the Endeavor management team stayed on as the management team for the new company. And Justin continued as executive chairman, me as his chief of staff. Um, and then in October of 17, we sold one Path so that we could focus on Dewar Mall business full time. Um, and we had a lucrative exit from that equity that we had purchased back in 2010. Hey, so that was very exciting. Yes. So that leads us to today. Um, it's kind of been business as usual since then with me as Justin's chief of staff and doing private equity and family office matters.

Emily:

Wow. Okay. So you're at DUR Mall now? Yes. Mm-hmm. Yes. Okay. So today you said business as usual, like itself. If we did some PE exits, we grew the company, thousands of people, dah, dah, dah, dah. Um, what is your scope of responsibility and work now, and how do you balance? It seems like Justin is in a whole bunch of different areas and doing a whole bunch of different things.

Speaker 2:

Yeah. Um, so my, right now our firm is involved in direct investments and co-investments, and we are supporting our direct investments, which we call our portfolio companies on a daily basis. So that means that I'm staying connected with those management teams, keeping an eye on what's going on. Am I hearing anything that Justin needs to know about, kind of like what I did in Endeavor, right? Um, and. I am also supporting the dot mall business, which is general, you know, regular business stuff, um, and supporting Justin on his personal matters so that he can focus on strategy and planning and big picture stuff for the portfolio companies.

Emily:

So, hold on, just to make sure I'm tracking. You have like PE firm that Justin has with the Port cos? Yes. And so you're working with like the leadership teams at each of those portfolio companies and kind of being the, the catalyst or conduit between Justin and those management teams? Yes. That's a huge job in and of itself, but you're doing that. and then what about the. Like the dot mall, is that separate or is that like the umbrella piece, or is that a separate? That's kind of the

Speaker 2:

umbrella.

Emily:

Okay. Yeah. And then you have, so everything

Speaker 2:

falls under that,

Emily:

and then you have the whole personal stuff, which I don't want to get into his personal stuff, but you're like chief of staffing, all of that arena as well? Yes. Okay. How do you do that? How do you balance

Speaker 2:

that? Yeah. Um, so I'm really good with boundaries, so I use the time blocking method. To focus on one thing for a set amount of time, usually a Port Co. And then the next thing I'm moving to is the next Port Co. So I'm not like shifting back and forth every five minutes. I'm kind of focusing my time on that, on one thing, handling all that, moving to the next thing, handling all that. And then it's kinda like this cycle that goes over the course of the day. Right. Um, and. Where was I going with that? I don't even know. No

Emily:

worries. I'm just curious too. Like I, I've seen, um, PE firms have a chief of staff at like the firm level, and then I've had them have a chief of staff as an operating partner that they deploy into their port codes. To like actually be in the operations of that business. Um, so I'm wondering, it sounds like you're more, um, like the liaison or conduit between the two. Are you ever involved in like, okay, because I know about this part of the operations, I know a part about this functional area, I can actually like be a little bit more hands-on. Are you kind of, uh, more high level than that?

Speaker 2:

We do get hands on, um, because. As you know, when entrepreneurs start a company, they don't think about certain things like HR and taxes and finance and those things. They're more focused on their big idea and how to get it off the ground and how to make a ton of money right now. Um, so that's kind of where we come in. We, our value added services are things like accounting and taxes and things like that. Gotcha. And HR and things that these guys don't think about. So, gotcha. Very cool. Yeah, so I'm not, I'm not like working for the companies, but I like in the companies, but I am doing things for them on a regular basis. Gotcha.

Emily:

Okay. Yeah, that makes sense. I mean, one of the advantages of PE firms is they bring those resources and networks and partners and hey, like, we can help you out by standing up this, you know, fractional HR piece or whatnot, and just. Get things stood up so they can go. Exactly.

Speaker 2:

Okay. Yep. And then eventually the companies get big enough to hire their own people and do that sort of thing, but we kind of fill the gap. Gotcha. So that they can get things. On board. Very cool.

Emily:

Very cool. Yeah. So you've been in this like long trajectory with Justin and I'm wondering, you know, 18 years, like I said, is a long time. Mm-hmm. And just as like growth as a person, you must have changed in those 18 years and Justin, I'm assuming changed and, and has grown as a person. So how did you evolve? Like what's the. Dynamic like between you two and what was that, um, like at the beginning and now it's how it is now. How did that evolve, uh, together?

Speaker 2:

Yeah. Um, so obviously some things have stayed the same, but a lot has changed'cause we're very different people now than we were, you know, 18 years ago. Um, so Justin has been my mentor basically from the start, which is really cool. Um, he. Obviously when we started working together, I didn't have a whole lot of professional experience. I'd had one job outta college and I didn't know a lot, but I didn't know what I didn't know. So he suggested topics for my professional development, like finance, investment, project management, uh, marketing, and even like telecom basics because we at Endeavor at that time. Um, and he, he is a very smart person. Um, he's probably the smartest person I know and by the time we started working together, he had already started multiple businesses and worked in international sales. So he is got a ton of experience and I can learn from him and I was happy to do that. Um. And you know, just thinking back to like that first day in the file room, one of the things about me is that I take a lot of pride in my work. So yes, I've been a manager a month before that, but now I'm starting this next phase in my career and I totally don't mind getting in these file cabinets and figuring out where everything needs to go. Like, I'm not afraid to roll up my sleeves and do whatever needs to be done. And I take pride in my work. So Justin realized that he could depend on me pretty quickly because he is given me these things to do and I'm getting them done. I'm getting them done quickly and accurately. So that started to build the trust of our relationship, right? Um, if I tell you I'm gonna do something, I'm gonna do it. If I tell you I'm gonna be somewhere at a certain time, I'll be there. Don't worry about it. Um, in fact, I had a colleague at one point in my career who told me that he could set his watch by my schedule because I was always like showing up at the office at 7 45, going to lunch at 12 o'clock. You know, so that to me big compliment because I want people to be able to depend on me. Nice. Um. So as the trust grew in our relationship, our partnerships evolving, I became increasingly involved in his family and personal business, um, and the community and the philanthropic endeavors that he was working on. And it might sound a little weird that. I would be so mired in somebody else's life that is not my spouse or not a member of my family. Um, but we had been very intentional to work on our relationship and making sure that Justin and my husband knew each other and knew each other well, and that I knew his family. And, you know, it kind of got everything ingrained together so that. Everybody was comfortable with the situation, if that makes sense.

Emily:

Totally. Yeah. I think, I mean, that's a really good point.'cause you're spending loads of time with this person. It is, uh, I mean, I was gonna say intense relationship. It is a very, like, you're very close and you're doing a lot of things together, and you're spending a lot of time and you're sharing a lot of information, especially on the personal side. So I think, uh, I, I like that you said. We were intentional about working on our relationship and then intentional about, you know, making sure that he knew my husband very well. So everyone is, is. Is good with the different dynamics that are happening.

Speaker 2:

Yes, yes. So I'm glad that we worked on that because it made things easier as time went on. Gotcha. Essentially. Um, so when we started working together, we were both under 30 years old, which if you think back to yourself that young, you were completely different person than you are now. Um, so we. We grew together professionally over the years. We are both so much more patient and empathetic and understanding, and it creates a very positive work environment, which I appreciate. Um, and we've also supported each other kind of through professional and personal ups and downs through our lives. Like we've 18 years, a lot of stuff happens and I'm glad that we have each other to kind of lean on when things aren't great, but also to celebrate when things are really great. That's awesome. Um, so that's really cool. Um, so for me, I have gotten a lot more comfortable with initiating uncomfortable conversations. Um. By default, I hate confrontation. So for me to decide to work on that and get a lot better at it was a huge thing. Um, you know, we're in this for the long haul, so let's make the effort to provide real time feedback and continue building our trust and improve our relationship. So that was a big investment that I made, you know, to, to improve our relationship and build the trust.

Emily:

Are you willing to say like what kind of things you did to work on that? It sounds like it was like an intentional, I need to get, I wanna get better at this for the long-term success. Let me put some steps in place. Was that just, was that just, okay, I'm gonna put myself outside my comfort zone? Or were there other steps involved in that?

Speaker 2:

Putting myself way outside my comfort zone. Um, if I observe something in a meeting, you know, I, I would kind of file it away. But then at, at some point I was like, you know what, this isn't doing me any good, keeping all these things in my brain, so I need to start sharing this stuff. And even though, like I knew that he wasn't going to get mad about anything that I said, but it was still like, oh my God, I'm so uncomfortable. I don't know if I can do this. So I, you know, I, the point where I. I want this to be successful, so I need to go outside my comfort zone and work on these things with him. So,

Emily:

and it sounds like, yeah, that was a huge thing. It sounds like the response was pretty positive, or at least it got to a positive point in the end.

Speaker 2:

Yes, absolutely. Yep. Which is very good. Um, and then just to kind of illustrate our partnership. I would say that Justin is one of the people I would call if my house was burning down in the middle of the night. Like I, I think that speaks volumes to kind of where we are and how much we trust each other and how strong our relationship is, so, wow. Wow. That's, yeah, I think that's pretty incredible.

Emily:

From the file file room to calling, you know, emergency contact, the house is literally burning down. Justin, please help me.

Speaker 2:

Yes, yes. Well, hey, let's actually go back. I wanted to talk a little bit about Justin's kind of extracurricular activities that I involved. A number of nonprofit and philanthropic endeavors, and this includes a foundation board at a university and an international historic restoration project, um, which is to restore do castle on the Isle of Mall in Scotland. Um, the castle has been around since 1360, so it's a pretty important part of history. So, I mean, I have been involved with nonprofits for all of my professional life. So when he decided to get involved in this, I was like, yes, this is amazing. Let's do this. Um, so in 2017, we actually went to Scotland to see the castle, and we were able to meet Sir Locklin, who is the kind of the head of the McLean clan. Um, so we were invited to the castle for dinner while we were there, so we get to the. To the door. And Sir Lachlan's son answers the door and he says, oh my gosh, we just lost power in the dining room. We're gonna have to have dinner by candlelight. Oh. And we were like, what? So that was amazing. Um, I guess when you have a really old castle, things like that just randomly happened, right? I wouldn't know, but I am assuming yes. Yes, I think it does. So we have the dinner. We had venison that was harvested from the castle grounds, which is incredible. Um, I'm from Pennsylvania. My family hunts, so that's something that I'm a hundred percent on board with. So we finish dinner, we go outside. It's like 10 o'clock at night and the sun is just starting to set because mall is like really far north. This was in June, so it's summertime, but we look out over the water because the castle kind of sits on the edge of the island. It's on the, on the coast, and we look out over the water and the sky is like this purple and orange color. And it was incredible. Um, I, I was like, wow, I just had candlelight dinner at a castle and now I'm seeing this amazing sunset. Like all these cool things are happening. Um. So on that trip we also took a helicopter ride, which is my first time in a helicopter. Um, and then we hiked to the top of Ben Moore, which is the tallest point on the Isle of Mole. And it ended up being a really good team building exercise because you're looking at Ben Moore from the C level and you're like, oh, that doesn't look too bad. It'll take a couple hours, but then you start to get to the top and it gets harder and harder. Um, but we made it and we were so proud of each other that we were able to do that. Um, so after the fact. I call Scotland my bucket list trip that I didn't even know I wanted to do because we did so many cool things. So,

Emily:

wow, that's an amazing story. That tells me, um, I need to up my game on team building exercises that they can involve a castle. Uh, yeah. So Jen, you not only win for 18 year tenure with your principal, you win for the, uh. Only Castle Initiative that we've had on the show. Love. So that is, that is amazing. Um, beautiful. To round us out here, let's just do lightning round. What advice would you give to chiefs of staff who are, you know, looking to get into the role for the first time, or existing chiefs of staff? And then I'll ask you same thing for principals, but just, uh, yes, I've got some thoughts on this. Yeah.

Speaker 2:

Um, let's see. So if you're a new chief of staff or you think you wanna become one, um. I think the, the main foundation is the relationship. If you wanna be successful, you've gotta have that relationship with your principal. Um, you know, we made a big effort to build it over the years, we're still working on it, and at the end of the day, relationships are the secret sauce for a team. Whether you've got two people, 20 people, or 200 people. Um, we had a lot of similarities. You know, we're close in age, similar Gen X experiences growing up. Um, and like I said earlier, neither of us are afraid to roll up our sleeves if there's something that needs to be done. Um, we're not afraid to do the hard work. Um, so take the time to find common ground and build that relationship and you'll become indispensable, um, because you'll become the person that your principal trusts, and that's huge. So you've got, you're working on your foundation, you're starting to build trust, get comfortable with the uncomfortable stuff. Um, I feel like one of my roles is being Justin's truth teller. I'm gonna tell'em things that other people might not say. Um, a lot of executives don't receive candid feedback and they're kind of, you know, in a bubble almost. And chiefs of staff can become that person to. Say the things that nobody else is going to tell them. Um, and when you, like I said, having the uncomfortable conversations. It's important, but approach it from a, from a place of helping instead of confronting. So start out a conversation like, Hey, you know, in the meeting yesterday, I noticed something that happened. I wanted to chat with you about it. Um, instead of going in guns blazing, like ready to fight, because that's not productive at all. Um, and then I also think it's important for chiefs of staff to be sounding boards. We almost always know the secrets that nobody else knows, but. You wanna also become that person that they come to when they need advice, when they're not sure what to do. Um, so I think one good way to do that is, you know, that your principal had a board meeting yesterday, follow up and say, Hey, how did everything go yesterday? Do we need to do any follow up? Um, kind of get put yourself in the position to be the person that they're gonna come to the next time for important conversations like that. And then don't be afraid to jump in and offer suggestions because you might have an experience from your past. Positions that could apply to whatever you and your principal are going through at this time. And a lot of executives suffer from decision fatigue, right? Um, so most of the time they're gonna be willing to give you the reins on some things. Um, once you've got that trust built, become the person that they're going to come to when they need something, you know, handled and. So, yeah, ingrain yourself. Um, become the trusted person, become the signing board, become the truth teller, and make sure that you keep developing that relationship. So that's my advice for a new chief of staff. And then as far as somebody who's thinking about getting a chief of staff or might already have one, if you don't have one yet. Ensure that you, you are ready to bring on somebody in that position. Um, the best chiefs of staff are the people who have access to everything and their principals are not afraid of delegating. Um, if you are not a good delegator, I think you need to put that on hold. Don't hire a chief of staff. Um, do some. Reflection and deep diving to figure out what is it about delegation that you're afraid of, because you've gotta fix that before you can bring somebody on in this important position. Um, and I'm gonna quote Tyler Paris. He wrote the chief of staff book in 2015, and he did a ton of interviews with HR people, executives, and chiefs of staff. To kind of figure out what really makes this role work. And he said that the executive's unwillingness to delegate was the number one reason that the role failed. So it's super important as a principal, you need to delegate. And if you're not ready to do that, don't hire a chief of staff yet. Um, and then if you are ready, consider the people that you've already got on your team. Uh, do you have a strong relationship and some level of trust with somebody that you already know on your team? Uh, do you see potential in any of your current team members for strategic thinking, strategic execution, things like that? Um, for me, starting a chief of several relationship with somebody you already know in another capacity, kind of eliminates half of the uncertainty right off the bat. If you already have a beginning of a relationship and you already trust'em. You know, if you think they can, you know, stand up to the challenge, then they're probably a good person to look at as you think about hiring a chief of staff. And then the last wisdom on part is that if you have a chief of staff and you wanna optimize them, make sure that you're focusing on keeping building that relationship as time goes on. Because relationships are like plants. They need certain things to thrive. And this to me means having conversations about things that aren't about work, right? So in, I have a story about this. In the summer of 2022, we're starting to emerge from Covid. You know, everybody's completely stressed out and tired of everything. But I was kind of reflecting and I thought to myself. It doesn't feel like Justin and I are driving like we did a few years ago. So I was like, Hey, do you, are you interested in maybe grabbing a drink once a month? Just that we have time outside of the office to talk about personal things? He said, yes, that's a great idea. So we've been doing that ever since. It's almost three years now, and it's really good to just have time where you're not talking about the portfolio company. Yeah. And you're talking about other things, and that's how you build the relationship. So keep develop, developing it. It's kind of, it's kind of like leadership. It's a journey. It's not a destination. Right. So it's something you always have to work on.

Emily:

Yes. I love that.'cause it's just a different kind of conversation, just different topics, but also like tone and tenor and just setting and everything. I think that is so important. And is it wrong that like. You said, if you're not ready for a chief of staff and you're not ready to give full access and to delegate, then you might wanna take a look at that and you might not be ready for a chief of staff. Is it wrong that I wanted to start clapping at that part? Like, oh my gosh, like this is amazing. You absolutely

Speaker 2:

should clap at that. Oh my gosh. Everyone needs to hear that. You don't wanna bring somebody in and then set them up. For failure? No, to me that's not fair.

Emily:

It's a two-way street. This is a very, you know, you gotta, it's complimentary dynamic. You gotta make sure you click and have rapport, like it's a two-way street. You gotta be ready too. So I love, love, love. Exactly that. You mentioned that. So thank you. Um, yes, Jen, if anyone wants to reach out to you, wants to know more about the PE firm, um, where, where's the best place to find that information?

Speaker 2:

Well, we've got our website do mall.com, and I'm on LinkedIn like all the time, so feel free to reach out to me on LinkedIn.

Emily:

We'll have those links in the show notes. And just to spell Doer, D-U-A-R-T mall. MALL? Yes. M-U-L-L-M-U-L-L. Gotcha. Okay. We'll have the link in the show notes. And Jen, thank you so much. It's been, um, it's been fun hearing your story and it's been fun hearing about your 18. Your tenure and partnership with Justin and your really cool castle initiative. I am. I'm not gonna lie. I'm a little jealous that you got to have that as one of your initiatives as Chief of staff. So thank you so much for sharing your story. Appreciate it. Thank you.