Jessi Lima Bollin is the Vice President, Marketing and Communications and second-generation member of her Cincinnati-based family business, Best Upon Request. The company provides concierge-style assistance with an eye to helping employees save time and decrease stress.

In the healthcare field, Best Upon Request also takes care of patients’ non-medical needs to improve the patient experience. More recently, Jessi spearheaded the development of the Maternity Concierge program to help employers provide a workplace support system to working mothers of infants. Jessi’s inspiration no doubt came from the fact that she and her husband Josh have three children of their own.

Best Upon Request is truly a family affair as Jessi reports directly to her mother Tilly, who serves as the company’s CEO. She also works alongside her younger sister Natalie who works in the HR department. Recently Ramia El Agamy from the Women in Family Business podcast and Amy Katz from Daughters in Charge sat down with Jessi to discuss the opportunities and challenges found in working so closely with both parents and siblings.

This episode of Conversations with Women in Family Business is co-produced with Amy Katz, founder of coaching-business Daughters in Charge.

Photo by rawpixel on Unsplash

Picture courtesy of Jessi Lima Bollin


Ramia: Jessi, we have invited you on this show for a very specific reason. Today’s topic is sibling dynamics and working with siblings in the family business. But before we get started on your very, very deep insights on this topic, we would love to know more about your very interesting business because it’s a very exciting business actually. You guys are actually pioneers in a specific area of service and we would love to know more about your family business and when you joined and how it all came about.

Jessi: Absolutely! We are a concierge company and we have about 15 offices across the United States. We partner with organizations in many different industries and we staff our team members on site at their location. What we do is provide any service that helps our client’s employees have less stressful lives. So essentially, anything on your to-do list, you can offload it to our concierges. We also serve in hospitals, we help support patients and their families with non-medical needs. We’ve been around since 1989, so it’s been a long time.  My dad was actually one of the founders and he eventually transitioned to my mom. We often talk about G1 and G2, but we had a little bit of a transition from G1A to G1B. My mom is also my boss, she became CEO in 2003. I have been with the company, all in all, for the past 18 years because I started working for the company when I was in high school. Currently, I am the Vice-President of Marketing and Communications.

Ramia: Great! And what other family members are currently working with you in the business?

Jessi: I’m the oldest of three girls. The middle daughter, Natalie, she’s our HR leader. We have a younger sister, Sophia who used to work for us years ago. She was trained as a concierge and also supported at our corporate office, but she’s decided to do something else. My dad is still very much involved as a consultant.

Ramia: We don’t need to talk to you about women in family business because you’re living it, working with your mom and your sister. Tell us a little bit more, were you working in the business a long time when your sister joined?

Jessi: We are three and a half years apart so she was probably about three or four years behind me. When she started, she actually had a lot of experience in different roles, and for a while, she was on my team. She did things like client and market insights so it was different and exciting to be able to work with her in that way. The good thing is we’ve always had a good relationship and so we’re good friends with each other. For us, it was just a matter of resetting expectations and being very clear about boundaries. Sort of like, now we’re talking as sisters but now we’re talking as teammates.

Ramia: You’re in an interesting dynamic in that you’re working with your mom and you’re working with sisters. Can you compare those dynamics for us? Is one easier than the other or do they both come with equal challenges are opportunities? What has been the relationship that you’ve more easily transitioned into in a professional capacity?

Jessi: That’s a really, really good question. It’s definitely very different with both of them. Part of it is because they’re two very different people with different personalities and different approaches. With Tilly, she is both my mom and my boss. Sometimes if I tell her something she’ll have maybe a mama bear reaction and I’ll say, ‘You don’t need to do anything I’m just informing you that this is something that I’m going to have to take care of’. With Natalie, we talk through things, we brainstorm together, and we talk about solutions, so it’s more of a collaborative type of relationship.

Ramia: Amy, do you think this has something to do with the generational gap, is that how you would account for such a difference? Or do you feel it’s very different from person to person or relationship to relationship? What have you seen when you’ve been working with Daughters In Family Business is so far?

Amy: I think you said it yourself Jessie, they’re very different personalities. I think the mother role is not the same as a sibling role. But I also think you might work, it may be even more typical to work better with your mother than with a sibling depending on the competitiveness between you, depending on the position you have in the family. I guess one of the things that struck me when you were talking about Natalie being on the team that you managed and now it sounds like she’s in a peer role again is that fair? What was it like the first time you had to give her critical feedback?

Jessi: For me, it was easy. I think because we have such a good relationship and we can tell each other anything, we also have a lot of respect for each other. It’s really about me as a leader, it’s in my delivery as well. So if I was giving critical feedback to anyone on my team, it would be in the same approach. Because Natalie and I have such a good relationship maybe it’s easier to connect with her and give her feedback. I think what’s important and that is just having that environment of respect and that point of me giving you critical feedback is just to make you a better professional and a better person. Starting with that framework is very helpful.

Ramia: What happened when the youngest sister Sophia was added to the mix? Did that change your dynamic with Natalie or did you guys just embrace her wholeheartedly and welcome her into the business? What happened there?

Jessi: Sophie is very different as well. She has a lot of strengths and she already felt that she didn’t want to be in an office environment. It was nice because the three of us were able to come together and Natalie and I were really being cheerleaders for Sofia and pour a lot into her, coach her and train her. We also helped guide her to see what she wants to do with her life. We’re kind of at a point where Natalie and I are more sensitive about talking about the business around Sophia because really, we want to talk to her as a sister. She wasn’t with the company too long and when she was, it was more out in the field so, it wasn’t bad.

Ramia: Was it disappointing to you when she left or were you excited for her? It must have been a bit ambiguous for you at that moment because I would imagine getting along so well, you probably would have liked to stay together the three of you as well.

Jessi: Sometimes I wish she was involved and we could have those conversations together. But I support her and if she wants to do something else, I’ll always support her. My sister and my parents and I do family council meetings, usually every quarter. In those conversations, we talk about the strategy of the company, the future and how it affects our family. So, Sophia is always part of that conversation, she’s part of our family. We always keep that top of mind, we don’t want her to feel left out.

Ramia: When you first started out, were you directly working with your mother or were you working with your dad? How did it begin for you as a business?

Jessi: When I started, I just managed the communications piece. I reported directly to our VP of Operations which is a role we no longer have. Over time, when we kind of restructured the organization and I had marketing, I ended up reporting directly to Tilly. What was really cool about Natalie being on my team was seeing her grow into the HR position. That came from someone in our leadership who saw something in her and came to me and said what about Natalie applying for the HR role? I said absolutely, I totally support that, and I can see that in her. I was always sensitive about being the boss’s daughter and the founder’s daughter and wanted to make sure that there wasn’t any perception that that’s the only reason why I got to the point that I was. And Natalie’s had that sensitivity as well and I’m guessing that’s just a common thing with daughters in family businesses. Natalie and I want to make sure that things are equitable and the opportunities that we’ve had are extended to all of our team members.

Ramia: So, the type of work that you do, it’s in the area really quickly right now. It’s very interesting for us to see that your company has been in existence since 1989, this concierge service, this distributed service to customers. We tend to associate this type of industry with newer technology with apps and stuff like that so it’s amazing to see this has been there for such a long time. Now that you’re in the second generation and mainly as a female leadership team, where do you see and what do you as sister see as your main priority right now for the business to get to the next level and to be recognized as a pioneer in that area?

Jessi: That’s a really good question. The great thing is we have an awesome leadership team that is very focused on what the future holds for us. You mentioned the technology, and there are a lot of apps which are service by demand. It’s something that we want to integrate into our service, but we want to be high-touch as well. A big differentiator for our model is that we are on site, you can actually build relationships face-to-face. But we had so many conversations about how we need to make sure that the current technology is integrated into what we do. Our CEO would say think about the future that we want. How can we make changes now so we can get the future that we want? The nice thing is that as a team, we have had that sense of innovation and that understanding that we know we need to innovate to remain relevant. That’s not something that’s just Natalie and me, that’s something that’s a whole team effort.

Ramia: I think it’s so interesting because, as people know from previous shows, I’m also one of three sisters and both of my sisters are actually working with me. I’m the middle child and I have a theory about this which is the eldest has a very special opportunity/burden/psychological mindset that makes this whole family business thing easier or harder. How much of your past decisions and feelings in relation towards the family business and your relationships do you attribute to the fact that you are the oldest of his siblings? Do you see a connection or do you feel all of those theories are totally beside the point?

Jessi: That’s really interesting. I think because I’m the oldest and because I started working in the business first, I think I kind of paved the way. I was able to pour into Natalie a lot of my experience, especially as a coach. I don’t know, that’s a hard question to answer.

Ramia: The listeners don’t know that Amy is emphatically nodding right now so let’s ask her. The influence of whether your first born second born or third born child in sibling dynamics in the family business, how do you feel this factor actually influences relationships? Do you feel you’ve seen patterns or again this is something that is highly individual?

Amy: I think the way that Jessie must have managed her role as an older sister set the stage for how Natalie has been able to receive feedback and grow from it. Also, Jessi isn’t holding on to that role so much that she won’t let other people contribute to Natalie’s development. I think it’s great that a non-family member said you may not see some of the strengths here and suggested that HR role. But I do think birth order has an enormous impact and it’s, of course, how you play it but it’s usually the next in line is striving to create her own identity. Natalie has done that apart from what your role is, and in doing so, she’s differentiated herself as a different person. You’ve accepted that and let go of that and have shifted now to be a peer. I think there’s a flexibility in the way they have managed their relationships in a way that I don’t often see. I will say that I know daughters who are first born who have younger siblings who are male, and sometimes the male does not allow that older sister to have much influence. That can be a different type of dynamic where the older sister is trying hard not to come on so strong, but sometimes that struggle happens when the younger male sibling is not allowing her to have the influence she deserves. In this situation though, I think somehow the word flexible, you’re able to move in different kinds of roles with each other with pretty remarkable ease and I think that’s wonderful. For Sophia, not to join when there’s been this pattern was probably important not only in that she took that step, but that your family was able to accept that and that you were still inclusive when you have family council meetings that she can have a place and lend her voice.

Ramia: I’m going to ask Jessi a sisterly question though from a younger sisters perspective, because of the middle child have a very inspiring position. I’m an older sister at the same time I’m a younger sister so it’s a very interesting perspective to have on these things. We have exposed ourselves in this conversation to Amy’s criticism, there is an episode with my older sister Frida and myself where were very candid and our feelings about each other – only love of course. I remember what happened to us was there was a huge element of surprise I guess as to the people we were at work as compared to the people we are in a private capacity. I wanted to ask you, were there things that really surprised you about Natalie and Sophia when they joined or that frankly astonished when you were at work? How did you deal with that?

Jessi: I’m sure this is true in every case, a lot of us act differently at work than we do at home. There are very different reasons for all of that. I do know that I like to think that we are very authentic at work. Sometimes what we’ll do when we want to connect here at the office is meet offsite but we’ll still go back and forth, it’s just very fluid. We can go from what’s going on at work or this issue that we’re solving or whatever and then it can go to vacation planning as a family. So, I don’t know if there was a surprise where we thought, oh this is a part of you that I’ve never met before. This is a new thing I need to navigate the way that you are. I would be happy to hear what Natalie says.

Ramia: I think we need to add Natalie to this conversation I think next time we’ll do an interview as a foursome here, that would be nice. More importantly, looking forward towards the future for you, transitions are going to happen very near in the future where it’s going to be you guys mostly running the show. Tell us, between you and your sisters, how does that conversation take shape? When you talk about the future, how do you envision the future without your parents in that active capacity especially with your mom not having an executive position necessarily, operationally? How did that conversation take shape and how do you approach that?

Jessi: A story comes to mind, this happened about almost six years ago. Natalie came to my mom and I and said let’s go through the Next Generation Institute which is a program for family businesses here in Cincinnati. We were kind of freaking out because I thought mom’s not going anywhere anytime soon, why would we go through the Next Generation Institute? I was also early pregnant with my second child, so the very thought of succession kind of intimidated me. But Natalie went to my mom and said I would like to see a job description as CEO, what’s expected? She had that ambition and curiosity and I don’t know if I was jaded but I just don’t want to take on that. I love that Natalie came with that kind of energy. We went to the Next Generation Institute and we learned so much about succession planning. And we learned that we have a lot of things going for us because part of the foundation is communication and we have that, thank goodness. We know that Tilly would like to keep the company in the family and so Natalie and I had conversations about what types of role she would feel comfortable doing and what I might do. So, the interesting thing is we have different places in that future but what makes me feel great about it is both of us. I want to go into the future with her because I think we both bring different things to the table and we both work really well together. My hope is that we would be doing it together.

Ramia: We’re very hopeful as well after this conversation. We will take Natalie’s perspective eventually, to be fair just to double-check if the elder sister has actually spoken the truth.

Amy: She’s an older sister so she definitely spoke the truth.

Ramia: Okay, I have two against one here. I have no chance, I’ll let this one go. Seriously though Jessi, it would be lovely to have you back. We’d love to check in with you and see how you guys are doing and maybe have your sisters join and Sophia of course because it’s so much fun having the siblings interrupt each other and contradict each other. Thank you very much for sharing your story and your insights and we hope to stay in touch and hear from you again.

Jessi: My pleasure thanks for having me.

About Amy Katz and Daughters in Charge: Amy Katz Daughters in Charge

Amy Katz is an executive coach and social psychologist whose business, Daughters in Charge, focuses exclusively on supporting women in family businesses.  She is the author of Daughters in Charge: Learning to Lead in Your Family’s Business.