It's okay to to show, you know, empathy to other people and to be vulnerable. I feel like I'm starting to really make my mark and changing the culture with becoming this culture of recognition. And then at the same time, I really started to work hard on just developing people and developing talent. And I put a lot of emphasis around that.
Zach Ewell:Welcome to the LeadersEdge podcast. I'm Zack Ewell, content producer here at LeadersEdge. In this episode, associate editor Chris Hann interviews Dottie Chalmers Cutter, chief operating officer at Chalmers Insurance Group. During this conversation, Chalmers shares her story of becoming the 4th generation to run her family's insurance business. She also discusses the importance of company culture and hard work.
Zach Ewell:Give it a listen.
Chris Hann:Okay. We are here today with Dottie Chalmers Cutter, chief operating officer and the 4th generation owner of her family business in Bridgeton, Maine. Thank you, Dottie, for being here. I appreciate it.
Dottie Chalmers Cutter:Thanks for having me.
Chris Hann:You're a 4th generation owner. And I wanted to ask if you feel does that do you feel any added pressure to keep this successful business successful as a 4th generation owner?
Dottie Chalmers Cutter:That's a great question. Absolutely. You know, I I always say, you know, there's 2 types of people. Either you're you're you're born into insurance or you fall into insurance, and so I definitely was born into it Yeah. Being this being a multigenerational family business.
Dottie Chalmers Cutter:My dad and my uncle, who are the 3rd generation, were absolutely adored, revered, and well known in not just the insurance industry, but in our our local community as well. And so, of course, I felt pressure, when we perpetuated, and I officially became the owner. But my dad was always, and he's still to this day, like, my biggest mentor. And so he he was always just so proud and was like, you you know, put your own stamp on this and and make it your own, and that was advice he had given me. And so I I just kinda did that.
Dottie Chalmers Cutter:I just started rolling up my sleeves and trying different things out and trying to change processes and culture. And, I think I finally kind of found my hit my groove, and I've earned the respect of our workforce, from really, I think, rolling up my sleeves and and starting kind of from the bottom. And when you're an owner's, you know, a a DOB, as I call it, daughter of boss, you have a bullseye a bullseye on your back. So
Chris Hann:Yeah. Yeah.
Dottie Chalmers Cutter:For me, it was really important to start from the ground up. And I I credit my dad for for doing that with me, and he's like, you really just need to learn insurance. And so I started as an account manager and got a book of business and serviced a book of business for many years on personal lines. And, really won over, like, the hearts of my coworkers because they saw me doing you know, sitting alongside them every day. And so that really, I think, helped me earn the respect, from those early years starting in that that way.
Chris Hann:Now let me ask you about that that, the chronology of that transition. You you came to the company, I believe, in 2005?
Dottie Chalmers Cutter:Yes. So I I graduated Bowdoin College, smaller art liberal arts school, and went and did a year abroad in New Zealand because I had studied there in college for a semester, and I liked it so much that I when all my friends were getting real jobs, I decided to get a 1 year working visa and go live my best life in New Zealand, and so I did that. And when I came back broke, my dad was very willing to hire me and, started having me work. And and I was familiar with the agency because I would work there on summer breaks from college. And in order to save up some money for my trip to New Zealand, I I started to work for the agency right after I graduated from Bowdoin for probably about 6 months to to earn some money and, started kind of doing processing work and commercial lines at that point in time.
Dottie Chalmers Cutter:But, so then I I live my best life in New Zealand, came back, and that's when my dad, you know, happily said, you know, let's let's get you let's put you in a and he picked a smaller office at the time, not even our our big flagship in Bridgeton, Maine. He he moved me to a small office in the middle of nowhere, Maine, and it was like sink or swim, very much a mom and pop agency. And I had to just really roll up my sleeves and be like, what am I doing? And I had a great mentor there and and just really became fucked and really realize, like, oh, this is a great career, and I could really see myself enjoying enjoying this work.
Chris Hann:And you took over as owner when?
Dottie Chalmers Cutter:I took over in 2018. It's when we perpetuated. But I had, you know, many years in so when I I think it was in 2013 when I my my cousin, who's my my business partner, Jim Chalmers, and then, we have another minority partner, Steve Cody, and I, we assumed kind of our, like, leadership promotions in 2013 where we were actively running the business. And my dad and my uncle in that at that time, we called it they they elevated to the balcony. So they were on the balcony looking down, and we were running the day to day operations, but they were there, you know, if we needed them.
Dottie Chalmers Cutter:So that's really kind of was a big defining moment, I would say. That's also when they gave Steve Cody, my partner, the presidency title, which was a big deal because it was the first time in our history where a non Chalmers family member assumed the presidency title. So that was a very big deal. And, and Steve's a good 10 plus years older than myself and my cousin. So at that time, you know, we were having babies, and and we're really in the weeds of, like, parenting.
Dottie Chalmers Cutter:And Steve was that much older, so he was, like, a perfect steward to take on that role and and to guide us and help us kinda get get ready, you know, for kinda where we are today. So he still maintains that presidency title. And I'm, chief operating officer, and and Jim is chief sales office officer currently. Mhmm.
Chris Hann:Tell me about when you came in, you mentioned you alluded earlier to some changes, just either in approach or you tell me what changes do you think what more what were the most significant changes do you think you brought to the leadership of the company?
Dottie Chalmers Cutter:Yeah. I think that's a great question. I think it kinda starts, probably, I would say, 5 or 6 years ago when I I took a a 360 assessment with a leadership coach. And that was a very defining moment for me because I was already, you know, actively running the agency or the daily operations. But I you know, you think you're you're doing things a certain way.
Dottie Chalmers Cutter:It's awful humbling when you have a 3 60 evaluation done, and all of a sudden your your peers, your direct reports, your bosses are are providing feedback. And so I got this report back, and it was very humbling for me because I realized, like, right then and there, I had some things I needed to do to change in my leadership. And so I really kind of leaned into that. I rolled up my sleeve after I got over the initial shock and, like, tears because it's hard to to get feedback on yourself, especially when you see yourself a certain way and you realize your peers are seeing you in a different way. Mhmm.
Dottie Chalmers Cutter:And so I remember going to my dad, you know, literally teary eyed. I gave him the assessment the report, and and he read it. And he, you know, he was in that moment, just like you're you know? Don't ever let the when you're looking at the reflection of yourself in the mirror, don't ever let that change because you are who you are. And this is you know?
Dottie Chalmers Cutter:You you will use this feedback, and you will act you will lean into it, and I know that about you and and who you are. But don't ever really let the reflection in the mirror change because you're pretty perfect to me. Now it's easy when a dad sell says that to his daughter, but I I took that, and I I also took the advice of some of my leadership coach, and I I really just tried to change a couple things. And so for me, it was, I had to practice a lot more, empathy and recognition in the workplace. My my coworkers didn't feel like they were being recognized enough.
Dottie Chalmers Cutter:And although I'm a very empathetic person, it wasn't coming across in my daily interactions with them. So I decided to do a couple things where I so my my leadership coach's advice was basically don't try and change everything about yourself overnight. You can't do that. But take 1 or 2 things, small things, and and make a difference. So for me, further, I just started recognizing people all the time.
Dottie Chalmers Cutter:And so I started small with with birthday cards and work anniversary cards, which I still do to this day. I send everyone we have a 103 coworkers. I send them a birthday card and a work anniversary card every year. I mail it to their house, a handwritten note, so they get it in advance. And I've been doing that for many years, and they they love that.
Dottie Chalmers Cutter:And they they so appreciate that. And I took it then I took it farther, so I still do that to this day. But now, like, I will send handwritten notes for any reason. You know? Like, I'll get for for things that my management team feeds to me, I will I will recognize always send a handwritten note because I'm a such a believer and and, like, I think it's a lost art.
Dottie Chalmers Cutter:Mail it to their house because that's best practice. And, so I started to change the culture, and I started to create this culture of recognition. Where what if we all started to do what Dottie's doing? And what if we all start to recognize everybody, more meaningfully? And we integrated that in many ways throughout our whole organization where we in a huddle that we would have between offices, we'll have we always build into our agenda.
Dottie Chalmers Cutter:We call them crush it. And it's crush it moments, and it's an opportunity for peers to crush one another. It's also opportunity for a manager to crush a a direct report, but we always build in crush
Chris Hann:Crush being a good thing.
Dottie Chalmers Cutter:Crush it is a good thing. Means and it would say, like, I'm gonna crush you for and then you have to get sort of specific for the impact you made by by you just staying late and servicing this client. You know, you brought in a new account, but you also, you know, helped this client out with the day before at closing. You know? So I'm crushing you for your commitment to exceptional client service, which is a core value of the company.
Dottie Chalmers Cutter:So we really tell them to to be specific with the impact, so that it's meaningful. So I feel like I'm starting to really make my mark in changing the culture with becoming this culture of recognition. And then at the same time, I really started to work hard on just developing people and developing talent, and I put a lot of emphasis around that. And, I'm actually a a trained leadership coach. And so I put on a 6 month leadership program for emerging leaders within the company, and it's a 6 month long program.
Dottie Chalmers Cutter:And I teach them the modules that were taught to me. It went from working with years of an executive coach. And so now I'm able to to to lead that program and help develop the rising stars, within the company, and that's that's pretty cool. So I think just the ability to recognize people and then the ability to to develop and promote and is is huge. So I think those are some of the aspects that I've been able to bring, and help change the company, you know, for the better.
Chris Hann:Mhmm. Mhmm. That, what your colleagues perceived as a lack of empathy on your part. Was that the biggest surprise to you in that 360, assessment?
Dottie Chalmers Cutter:It was because I had taken a caliper test when I just started at the agency. My dad did caliper testing on everybody, and, I took it. And I know on that report, I was 99 percentile for empathy. So I knew I was very empathetic, but there was some kind of a disconnect where
Chris Hann:Yeah. Yeah.
Dottie Chalmers Cutter:It wasn't coming out. So I'm a very empathetic person, but yet my my coworkers weren't seeing that. So that was very surprising to me. And so I I basically not just started recognizing people, but I also just started practicing what I call humble inquiry and curious curious listening. So I was just asking lots of I was doing less talking and more, asking of my staff.
Dottie Chalmers Cutter:So I was trying to basically get to know them at a deeper level, a more personal level. And I think my ability to connect with people is is is an advantage, that I have, but but by asking and leading with curiosity, I found that I was able to get them to open up to me and I was able to build meaningful connection. And so, so that was all really because of the that 360 assessment that I I took those, you know, 5 years ago. Mhmm. So, I think that you know?
Dottie Chalmers Cutter:And then being, you know, vulnerable. I think people saw me in a certain way, and I also had to realize, okay, daddy. It's okay to be vulnerable. It's okay to show emotion. I know I'm an empathetic person, but maybe in the workplace, I was a little bit more, you know, work professional.
Dottie Chalmers Cutter:And so I realized, like, it's okay to to show, you know, empathy to other people and to be vulnerable and at my own expense, you know, to make myself, like, you know, hey. Look. This is where I I missed the mark, or this is this is something that I did that I did wrong. And I and being able to admit that publicly, I think, has served me well, and has shown people in my organization that it's okay it's okay to make mistakes. And and being vulnerable about it, being able to lean into that, I think, has really kinda helped helped me show, like, I am I am an empathetic person.
Dottie Chalmers Cutter:I am vulnerable. I'm okay to put myself out there, at my own expense. And I I think that makes for, you know, I think that makes for the best leaders, those that are able to kinda lean into that and do that.
Chris Hann:What was when you took over, you had been with the company for quite a while before you Mhmm. Before you took over Yeah.
Dottie Chalmers Cutter:Yep. At
Chris Hann:the as as as the leader a leader. What was the biggest surprise in making that transition, to to the leadership position?
Dottie Chalmers Cutter:Yeah. It's a good question. I mean, my dad for, like, a decade called me the junior management team. Myself and my cousin, we were like, we were learning. It was so embarrassing because we were he would still call us the junior management team, and we were, because we were he would still call us the junior management team, and we were in the management meetings.
Dottie Chalmers Cutter:And we were just junior because we were the the young ones. And I remember because finally, it was like we were clearly leading the agency. By 2013, we were we were leading it. And I was like, dad, can you drop the can you drop the junior now? Because we're not junior anymore.
Dottie Chalmers Cutter:We're really we're really senior. I think we're leading the company. But, yeah, I think, you know, the early years was just understanding the business, understanding insurance, and then being able to, like, speak up and use my voice. And and I was somebody that actually was really shy as a child. And even through college, I was wasn't the 1st to speak up in class.
Dottie Chalmers Cutter:Like, I would be the one that had to really be poked to speak up. And and if class participation was part of a grade, then I was like, oh my gosh. I'm gonna have to speak up. And, so I was I was shy, and that was something I had to overcome. And I I started to kind of those early years, I think my dad was smart.
Dottie Chalmers Cutter:He knew that was something I had a challenge I had to overcome. So he would call on me, in managers' meetings. He would purposely ask me to be prepared. I'm gonna call on you. You're gonna speak about this.
Dottie Chalmers Cutter:Or we might bring in a, our banking partner for annual state of the union meeting with them, and he would always make me present to them. He'd make me to present to when carrier partners and marketing reps would come into the agency, he would always that, Dottie, tell them what it's like in personal lines. Tell them what the what the rates how their rates are. And then he would just watch back and, like, watch me. And after afterwards or at the end of the meeting, he would kinda give me feedback and as a coach would and tell me, like, you know, how I did.
Dottie Chalmers Cutter:And that meant that meant a lot because I was very much achievement motivated in those days, and I I was craving that type of feedback. So, I think in those early years, it was about me being comfortable using my voice, being comfortable speaking up in a in a meeting and in a crowd and knowing and trusting that I actually know what I'm talking about. So, I would say those were those were obstacles, things I had to overcome in those the first probably 10 years at the agency.
Chris Hann:What was it like working with your father?
Dottie Chalmers Cutter:It was pretty special, and he's, you know, he's the most amazing person in my life and my oh, ex my husband. I I have to say it. I can't slide him, but my dad is really my mentor, and, he is just such a cheerleader of people. And, you know, obviously, his kids are no different, but he has this he's has such high integrity, and that would be a word I think anybody would use when you think of of Bill Chalmers. They would say, what a man of integrity, of character, of humility.
Dottie Chalmers Cutter:Not one to be showy or boastful, but just somebody that when he spoke, you listened. And he had this gift of being able to to to to have a direct conversation, but he would do it in a way that people were like, I don't know if I wanna, like, be his best friend, or did he just also give me some course correction? I don't know. Like, I love him. He had that gift about him and and is, like, a masterful storyteller.
Dottie Chalmers Cutter:So those early years were special because he my office was near his, and he would he would call me in or he would come into my office and just sit down and, or pull me into different meetings. And I was able to really to just learn through observation and seeing how he did things. And then he also knew because he was my dad and and, you know, and and, you know, worried about maybe nepotism or whatnot. He had a he had a, then a COO who he tasked with mentoring me, And she played a very important role in my my career as well in in helping teach me and and prepare me for the position I'm in as well. But, no.
Dottie Chalmers Cutter:My dad is is somebody that I still it's great because he's retired, but he's he's he's alive. He's around. He's available, and he so loves to talk about the agency, and he's so proud. And I think that's, that's something that he just, like, he's just so proud and happy to see the the agency continue and to see myself and my cousin carrying on, you know, and his good work. And and he would be the first to say, like, and you're doing a better job than I ever did.
Dottie Chalmers Cutter:You know? That would be the next thing out of his mouth is that you really you really made this something even more than I I ever did. And and I I think the emphasis on the culture piece was something that I felt proud of that I was able to really put my own stamp on, and that has earned us best places to work in insurance. 2 years. We we we apply every other year, but I our overall employee engagement score is a 97%.
Chris Hann:Let me ask you about culture because so many so many businesses and and and executives and CEOs, out their culture, and obviously, it means different things to different people in different companies. How would you describe the culture at Qatar?
Dottie Chalmers Cutter:Yeah. So I would I would call it we have this culture of 2 things, culture of I I call it coaching leadership, where we we want to see the best in others as a coach would. So it's very much this mentality as you're a manager as a coach versus manager as a boss. Mhmm. And that's been a core kind of ideology for us that we've embraced.
Dottie Chalmers Cutter:And everybody in the company knows that we're gonna coach you up. And there is a time where sometimes, like, if we can't coach, we have to maybe a a person, maybe it's just not a culture fit. Now we might have to to turn to the the management, put the management hat on, and manage out a problem. But but, really, our emphasis is on we're gonna coach you up, and we're going to develop you. So creating this culture of coaching leadership where we're gonna see the best in others, where we are going to express appreciation for others.
Dottie Chalmers Cutter:We're gonna promote development. We're gonna set clear goals. We're gonna hold people accountable. That's all part of a coaching leadership culture. So that would be 1.
Dottie Chalmers Cutter:And then the that I would say that that recognition piece is critical. And then having core values that everybody in the company absolutely embraces, understands, knows, believes, and champions. And if you have that, it's magic. It really is. If you can get everybody on the bus or on the boat as we say because we, we have an acronym called SHIP, s h I p.
Dottie Chalmers Cutter:That stands for our core values of, like, of, exceptional client service would be the s. The h is honesty with everyone. The I is involvement in our community, and then the p stands for passionate professionals. So we call it ship. And it's a nod to my dad who we call the captain because he you would think he has, you know, his captain's license officially, but he just happens to love to wear a captain's hat, and he's captain of a pontoon boat in, in beautiful Highland Lake, Bridgeton, Maine.
Dottie Chalmers Cutter:But so it was kind of a a nod to him at the time when we created this acronym of SHIP. But we were able to really bring it to life, and everybody in the company believes in it, knows it, champions it. It's it's on every agenda. It's on the walls in every office. It's in everyone's desk.
Dottie Chalmers Cutter:They have a a frame with the values. So, when you have that, it's it's that's where I think we get that 97% overall engagement because everybody believes everybody's on the boat. Everybody's rowing in the same direction, and it's it's pretty special to see it come to life.
Chris Hann:Tell me about the founding of the company. This would have been your great grandfather, I guess?
Dottie Chalmers Cutter:My my great great grandfather. Yes. So we were founded in 8 1857. So we are 4th generation. And, yeah, it was it was you know, I I we actually have book iterations of books of the history because it is, it is that in-depth.
Dottie Chalmers Cutter:But, yeah, basically, it was through marriage through my dad's my my dad's mother, her her father was a his last name was Braithwaite. And, he he, partnered with a local agent in town, and it was, like, the Braithwaite agency. And then he let in my grandfather, so last name of Chalmers, and so it became the Braithwaite Chalmers Agency and then dropped the Braithwaite, and it was just became Chalmers Agency. So, yeah, so it really goes back from great great grandfather, my grandfather, my father, and my uncle, and myself, and my cousin, Jim. And we have other siblings, but, not involved in the agency side.
Dottie Chalmers Cutter:My my dad and my uncle do have we call it a sister company. That is a, a TPA, a third party claims administrator company. And my sister and my cousin's younger brother actually run that arm, but it's a different business entity. So when I say my sister company, it really is my sister company. My sister is the president and CEO of that company.
Dottie Chalmers Cutter:But it's so we're really you know, we we do have a lot of a family under the umbrella. But in the terms of the Chalmers insurance, the P and C, you know, the agency, it's just myself and my cousin, Jim. So that's we we are the 4th generation. And the goal is to get it to the 5th generation, and they are interested. So that would be my daughter.
Dottie Chalmers Cutter:I have 3 kids. My oldest is 14, and she has known ever since kindergarten, that she wants to be a Chalmers insurance agent like my mom. And that's something she would say on the first day of school, every year when they they hold up the little placard that says, you know, what do you wanna be when you grow up? And she says, I wanna be a Chalmers insurance agent like my mom. Now she's a freshman in high school.
Dottie Chalmers Cutter:She still holds that sign up on the 1st day of school, but now she's smartened up and she says, I don't wanna be a Chalmers insurance agent. She goes, I wanna be the Chalmers agent CEO. I wanna be the boss. So she's just smartening up now, and she doesn't wanna be the agent now. She's like, I really just wanna I want your job, mom.
Dottie Chalmers Cutter:I wanna be the boss. Wow. Chalmers And so that's going strong. She's 14 now, and then I have twins, boy, girl twins that are 11. And my son says he wants to be the COO.
Dottie Chalmers Cutter:And then my his twin his twin sister, though, says, no. I wanna be a a beauty spa owner one day. So she's not she's not interested. But then my 14 year old says and I'll ensure you. You can be a beauty spa owner, and I'll ensure you.
Dottie Chalmers Cutter:So it's pretty cute to hear the dialogue, You must brewing.
Chris Hann:You must bring home some good stories.
Dottie Chalmers Cutter:I bring them a lot of stories, a lot of stories, and they hear an awful lot. And I I actually try and and and do that purposefully because I want to see how they're starting to problem solve real world things. So I did it the other day. We we we were having, like, a hot tub with a family and making small talk, and I said, I have a problem of the day, and I want your advice. And I walked them through a scenario that was that really happened to me that day, and I said, how would you handle it?
Dottie Chalmers Cutter:And I wouldn't tell them any names. I said, but this is the situation. This is what happened, and I wanna know what how would you figure it out? How would you solve it? And it is so interesting to see their little the wheels turning in their brain already.
Dottie Chalmers Cutter:And, and I'm doing that intentionally because I wanna help to help develop that and let them know that, you know, this this is what it's like to run a business as a business owner. These are things you will face and challenges, and how are you going to overcome that? So trying to start them at a really young age.
Chris Hann:It's all about problem solving. Right?
Dottie Chalmers Cutter:It is.
Chris Hann:When you were young, was it expected that you would go into the business? Did you want to go into the business? Did you aspire to it like your 14 year old daughter does now?
Dottie Chalmers Cutter:No. I did not. This is funny, though. So I thought I wanted to be a doctor, specifically a pediatrician. And my dad, though, would always whisper insurance insurance in my ear as a kid.
Chris Hann:Literally literally whisper.
Dottie Chalmers Cutter:Literally whisper insurance in my ear and only to me. Only he had 3 kids. I was the middle child, and he would only whisper it in my ear because he knew out of his 3 children, I was the one most similar to him. And I think he knew I would be the one that just had had the instincts or had an enemy to to take over the agency. So he wouldn't whisper to my brother and my my younger sister's ear.
Dottie Chalmers Cutter:He'd whisper to my ear, and I would just be like like a like a a little bee in your ear. I just I'd kinda like wadded away. I'm like, no. No, dad. But subliminally, I think it really got through, and it was always something in the back of my mind that I knew could be, an avenue for me to explore.
Dottie Chalmers Cutter:So when I went to Bowdoin as a pre med student, I realized pretty quickly after, like, barely passing biology 101 that this was gonna be a problem. And I, I was like, I don't know. If I can't barely pass biology, how am I ever gonna get through organic chemistry? And so I decided to pivot, and I I went towards, psychology, actually, and became, got my degree in psychology. And I you know what?
Dottie Chalmers Cutter:I use that every day. I'm grateful. I I use psychology, and it helps me understand people, and that is really the business that I'm in, is the people business. Whether you're managing your workforce or client interactions, like, it's all about people. So I, I did a pivot and, realized that, okay, maybe now.
Dottie Chalmers Cutter:I think I gotta give insurance a a thought, and, and that's when my dad was obviously very willing to to hire me. So
Zach Ewell:That was associate editor Chris Hann interviewing Dottie Chalmers Cutter. I hope you enjoyed it. For more episodes of our personal lines podcast series, go to leadersedge.com or find our podcast on SoundCloud, Spotify, and Apple Podcasts.