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Growing Your Family And Business Through Setting Boundaries With Stacy Kahan


As an entrepreneur, you want to thrive in your business while making time for your family too. In this episode, Stacy Kahan shares her professional journey on setting boundaries for personal and professional growth. She left the corporate world to start her business because she wanted a balance between her work and family life. She shares mistakes running the business and learnings especially when handling people and employees. She lets them fail and experience hardships themselves to be able to grow which in turn will help her business grow as well. Listen and know the right approach for your business!



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Growing Your Family And Business Through Setting Boundaries With Stacy Kahan

In this episode, we’re talking to Stacy Kahan, who is going to talk about being a better leader. Stacy says that insurance is not only in her blood, but it’s something that she’s passionate about. She gets to discover what people’s dreams are for their businesses and their personal lives. She then uses insurance to help them get there. For every client, she makes it a firm commitment that they will walk out the door in a better position than when they met. Stacy is going to dive into providing feedback as well as having a solid succession plan in our conversation, so keep reading.



Stacy, thank you so much for being with us. I know that you’re an Employee Benefits Expert, and you started your company way back in 1994. Before that, I know that you were in corporate. Why did you leave corporate? What made you leave corporate?


Going back many years, I realized that in order to have a family and have some balance, it could not happen at a C-Suite level, so I felt that it was imperative that I went out on my own to allow me to have the balance I needed to grow a family, a business, and literally have a balanced life.


To me, that answer means that you were working a ton of hours when you were in corporate.


It doesn’t change when you have your own business. It is a different pressure.


I know that you have a lot of experience in leadership, and we know that a lot of times, managers are so busy in their day-to-day that they don’t have a ton of time to develop their team. You have a team of your own. How do you keep your team engaged? What is it that they do so that they can be vested in their work?


We have to do a number of things. The first thing that’s most necessary with any team is good feedback. Without good feedback, you have nothing, so we start with that. As we’re working with our team, weekly initially, giving them the feedback that they need to be successful, then it becomes longer stretches. Leadership involves that and involves challenging your people. Thirdly, it involves having an open door. Even though they’re challenged, they know that when they run up against a wall, they have somewhere to go to get the answers. My feeling is there are no questions in which there are any dumb questions and dumb answers. If anyone asks, I’m willing to give them the answer.


It’s a different kind of pressure when you have your own business. – Stacy Kahan Click To Tweet


I know that you have two beautiful daughters. I saw a picture of you online in the office with your daughters. First of all, that is a beautiful picture because the three of you leading your team, in general, is fantastic. I know that you have a succession plan for your team. How did you come up with a succession plan for them?


The hardest part of a business is growing it but secondly, figuring out how to keep it alive even if you’re not as involved. I was lucky enough that my two daughters did come into the business. Prior to that, I never thought they would come into the business. I had a few different women that I had brought up who I thought could succeed me but, in the end, they didn’t have the talent to run a business, be a business developer and manage people well. They couldn’t do it all.


The reason why I’m bringing this up is that in corporate, we still have a ton of women who are managers, and they’re trying to balance their life with their work responsibilities, and if they are a manager, they do have a team of people. I was curious to hear what are some 2 or 3 ideas that you have as to what a manager can do to either develop their team or engage them more in the work if the employee is not necessarily engaged in their work?


First off, you have to be a photocopy of what you want people to be, so that means having a balanced life, allowing people to fail in order to grow. The tips are understanding how each of your people tick, giving them the tools to be most successful. That’s the first thing. Every single person is different, so you have to get that feedback one-to-one where they are to help them. It’s not cookie-cutter.


I have known of various different assessments that you can use, and StrengthsFinder is a good one. The employee has to take the assessment but as a manager, it helps you identify the strengths and weaknesses of your team so that you know what assignments to assign to them. I talked to someone who was screaming, yelling, and calling attention to their manager saying, “Pick me. Pick me.” It’s like Donkey’s, “Pick Me.” The manager was like, “No,” and then they gave it to another person, but that person had the strengths for that particular project. It’s important, as a manager, to know your team, know their strengths so that you can play on their strengths and then give them the projects that they can best do.


It’s funny you say that, because we went through a year of Kolbe already with each of our team, taking the Kolbe Index, then evaluating how each person needed to be managed in order to get the best results. Thirdly, and the most important, there was a grid. It was a little box where everyone sat, and what we noticed is we hire people that are like us not necessarily complementing our strengths so we had a lot of blank spots. It’s important and imperative that a manager doesn’t necessarily hire people that they like but people that can fill in the spots on a team that are weak.


NWB 16 | Setting Boundaries
Setting Boundaries: Allow yourself to have the balance to grow a family, a business, and literally have a balanced life.


That’s pretty enlightening because managers are going to hire people like themselves. To hire people with other strengths so they can fill those spots is fantastic. You said something earlier, “You have to let them fail in order to grow.” Let’s talk a little bit more about that because I love that. By the way, before I let you answer that, I am working on different projects where I am researching girls’ confidence.


I found a statistic by a clinical psychologist that says that girls’ confidence peaks at age nine. It’s incredible, but the reason why I was looking at this was helicopter parenting may not allow their daughters to fail. When parents are constantly fixing problems for their daughters, it pretty much propels them into not being able to negotiate salary, and it will reduce their salary over a lifetime by $2 million. I love that you talk about this. Fail in order to grow. Talk about that and what do you mean by that?


I had the most interesting conversation with a woman who runs a nice-sized tech business and she said, “You sometimes need to let people wear different shirts to figure out where they fit best. You can look at indexes, but they have to be able to put on that shirt each day and feel comfortable in it and confident.” If the peak of confidence is nine, what happens? Although I did not do this with my children, I said more noes than yeses. What happened was you had to challenge that and let them fall, let them bleed in order to brush themselves off and move forward. It’s exactly that way in life and it’s that way in business.


Another interesting tidbit that I read about this in this particular article was that some parents are going on interviews with their adult kids, and a few parents would go to day one of the job. It’s mind-blowing, number one, that parents would go, and number two, that kids would allow their parents to go with them on interviews and the first day of business. Isn’t that crazy?


It’s completely insane. Your parents are not going to be sitting next to you. They can coach you but you’re on your own once you walk out that front door.


You are passionate about what you do and about your work and insurance. Where did you find that passion?


You have to be a photocopy of what you want people to be. That means having a balanced life, allowing people to fail in order to grow. – Stacy Kahan Click To Tweet


That would be my dad. He started in the insurance business when he was a young man. I watched a balanced life where he was able to help people and grow money, so he was able to give all of us the life he wanted when he was a child that he didn’t necessarily have. It propelled me that I love business, I love people, and I knew it was a way I could grow a business, have a little bit of flexibility, and at the end of the day know the people I touched are in a better place than when I wasn’t in front of them.


Did you know from an early age you wanted to go into business instead of corporate? How did you get into corporate and then business?


I worked for a couple of big insurance agencies. Women were more secretarial and administrative than in sales for sure. In my first year of Million Dollar Round Table, which is the other side of the business, the life side, 2% were women. That was it. You looked around and said, “How do we mentor women to be different from this?” It started at our kitchen table. We were a family of girls besides my dad and he challenged us every day to be better, and be smarter. At the end of the day, I was somewhat of a replica of him, and it allowed me the freedom to have a good life.


I absolutely love the fact that your dad was challenging you continually because not many people have that. My dad always challenged me and my siblings. Every time, we’d be like, “Dad, I got an A.” He’s like, “Why didn’t you get an A-plus?” If you got a raise or something or started a job, for example, my first job was like, “Dad, I got a job.” He was like, “Did you ask for a raise?” He’s kidding but at the same time, I love the fact that your dad was challenging you. Did you have female or male siblings?


I have one sister. She’s different from me, but we both sound around the table. She went into social work, which is a noble cause, but it’s a difficult place to make a living. I saw the other side of nobility and I feel that I’m noble too but the nobility of being a social worker doesn’t allow you to have much of a balanced life because cashflow is tight.


You and I had a brief conversation previously, and you said that you have always supported women, and raised women up in the world in your environment. Talk to me a little bit about that. How have you done that in the past? How do you think women can raise other women? This is exactly what we’re trying to do here. My mission is to eradicate the gender gap in the world and in corporate. I’m doing that by empowering women in their careers, which is why we’re having these important conversations. Tell me a little bit about that. I remember you saying that you’re not a jealous person, which is fantastic because in order for us to collectively raise women up, we need to be able to give back. I’ll let you comment on that.


NWB 16 | Setting Boundaries
Setting Boundaries: The hardest part of a business is growing it. But secondly, figuring it out how to keep it alive, even if you’re not as involved.


The only way to empower women is to educate us, and it’s not just in school but in finances, how to seek a job, but not a low-level job, a high-level job and push your way to the top. That does require women helping women like how men help men. The only way any of us are going to be sitting at the head of these big companies is by pulling each other up.


It’s so interesting that you say educate ourselves not just at work, but in finances. I was in a meeting and unfortunately, it was an older woman whose husband had died and she didn’t know anything about her finances. She didn’t even know how to use her computer. It goes back to the whole thing about you as a woman. It’s perfectly fine to be married, have a lovely relationship and have a partner, but you still have to know what is happening in your finances and in your household. When something happens, because we’re not all going to live forever, you’re prepared for those finances or financial changes. You’re in employee benefits, so I want to ask you, what do you do, Stacy? How do you help people in your business? Tell me a little bit about your background.


I have a degree in Risk and Insurance and Finance, which is a long time ago. I immediately went into the insurance business for New York Life. Initially, I was selling life insurance and disability and long-term care only, and realized to take a holistic approach to business as a whole. You need to handle two sides of a person’s life, their business life, and their personal life. There’s a holistic connection that needs to be handled and I always say, “If your business blows, your family is in trouble, but if your family blows, the stress it can put on your business, if there’s not enough planning, will blow the business as well.”


It comes back to succession planning. It comes back to making sure there’s someone that can pick up the pieces if you get knocked out and you’re disabled at a young age. Things like that happen. It’s exactly what you said. If you have the planning in place, as you’re talking to this business owner to think globally, initially, and then dig deep on both sides, you find where their love is. Many times, that corporate pocketbook can fund much of the personal as well. You’re able to build wealth within your company and build your family. It all coincides as one.


That’s beautiful because it doesn’t matter if you’re in business for yourself or if you’re in corporate. It’s pretty much the same thing as far as we want to make sure that women are advocating for themselves moving up the ladder. At the same time, you don’t want to be so focused on your job, your career, your business, that you let your family fall by the wayside. That’s no good either. You talked about balance at the beginning of our call. What are some of the ways that you have been able to maintain that balance between being a leader and your personal life?


That’s a great question. I will tell you that I’ve made errors. My daughter, who had come to work for me, at one point said I was more of a boss than a mother. We had to figure out the boundaries. The boundaries were this and you’ll get a kick out of it. No talking about business on Sundays. My brain is always thinking, “We have a family dinner.” The weekends are not a time to talk business. The business was done during the week and it changed the way that we behaved as an adult family.


Leadership involves challenging your people. – Stacy Kahan Click To Tweet


You hit on a couple of things there. I love the whole, “You’re more of a boss than a mother.” That’s a pretty good distinction because sometimes when you’re a leader, a manager, and especially nowadays, before the pandemic, I drove an hour to him from the office. I had that time to decompress, debrief and shift from leader, boss, manager, to mom, wife, and that kind of thing. We’re working from home, so I walk out of my office and I’m still in the go, go, go leader, leader, leader. Like you, sometimes I forget to switch off those hats. You have talked about boundaries. I want to talk a little bit more about the boundaries because that’s so important. What are boundaries and how do you use them?


In business or in personal life?


Both. Either.


What I have learned in raising good children is they need boundaries, for sure. People need boundaries because they don’t know whether to go far enough or they’ve gone too far. Boundaries make a person feel more comfortable about the choices they make. With that being said, everyone has different boundaries. In work, it’s important to explain the boundaries of the business as you’re interviewing someone, as you’re doing whatever kind of index to determine if they’re the caliber person that can touch your clients that you work so dearly to get and to keep. I am black and white when it comes to boundaries. There’s not a lot of gray with me.


Boundaries are also for people that are in corporate. You work from 8:00 to 5:30 or whatever your hours are. I know that some people physically have to pull themselves away from their computers because they can keep working for hours, and again and it depends on what your family situation is. If you have little kids, you’re not going to be able to do that. I don’t have any little kids, so there’s nothing stopping me from staying in front of the computer, but it’s important for people to set boundaries for their work schedule, specifically now that we’re working from home.


When you set boundaries between your work and your life, it gives you that balance that we all want so much. I love the fact that you don’t talk business on Sundays, weekends, or whatever. What happens if you think of something on a Sunday and you want to talk about it? Do you write it down? Do you send yourself a message to address it on Monday? That would be awesome.


NWB 16 | Setting Boundaries
Setting Boundaries: What we noticed is we hire people that are like us, not necessarily complementing our strengths.


I will write it down. I’ve learned that it’s something that makes it much more family-oriented. That’s what I learned. I had a life balance coach for over twenty years and his mantra was, “You wrap your business around your family, not the other way around.” You can have a great business, but if you don’t have a family at the end of it because you never make it home or you don’t leave your computer, what’s the point?


When you’re a leader, there are seasons that are super busy and seasons that are a little bit more on the wall. Do you think that in your busy seasons, you’re able to maintain that same balance?


In my later years of business, yes. In my younger years, my first twenty years, we had a crazy season in the employee benefits market. It starts pretty much in August through the end of January. It was for six months. It was horrible because that was when all our clients were renewing and that was a governmental thing that happened so you have to build more efficiencies.


How do you do that? You do it by technology, and so that’s what we did. We sat back and said, “What do we need to do?” We started building tight CRMs, ticketing systems, and tracking our employees’ time in those tasks to determine if they were sitting with the right seat for them, or were they struggling in parts of their job? We can see that and then we know that either we have a long conversation and see if it’s a struggle that they’re not good at and it’s killing them and you put someone else there, or whether through mentoring and education that it’s something they can be good at.


I want to go back to something you said about a conversation. I’m assuming it’s going to be somewhat of a difficult conversation if someone’s not being successful in what they’re doing. Stacy, how would you conduct a difficult conversation? What would it look like?


I am a manager that begins with the good things. These are the things I’m impressed with. You make it to work on time, you have your head down, and it appears you’re doing your job well, but my concern is the dots aren’t going together. They’re not coming together, so I need you to tell me what’s happening. I like open conversation with people like that. I’ve learned from my children that anyone will say, “I ask a question, and I shut up.”


The only way women are going to be sitting at the head of these big companies is by pulling each other up. – Stacy Kahan Click To Tweet


Why do you ask the question, and then you shut up? What is the purpose of you doing that? What is the technique there?


I want someone to think about the question and come back with a response without me interjecting because I’ve asked and I need to listen. Two ears. One mouth.


When it comes to those difficult conversations, it is pretty imperative for a manager to listen, and a lot of managers don’t know how to listen. What is your technique to listen to the person that you’re talking to?


First, you look in their eyes, you look at someone’s body language, and you try to make a neutral place for them to feel comfortable. The first is they’re going to feel comfortable. We’re not going to slay them. They may end up getting fired if things are bad, but I never had an employee that doesn’t know prior to them losing their job that they’re not going well. They know exactly where they stand. Some jobs aren’t for some people as you watch them turning white over the weeks.


Not everybody is cut out for all jobs so for sure. I like your technique of listening to the person asking the question, then being quiet so that they can think about the question and then speak, talk about whatever their challenges are. When someone comes to you and says, “I’m sorry. I don’t get this. I’m making mistakes. I need help,” as a leader, what is your method to help develop the person? They’re coming to you because they want to do well and want to succeed. You know that if they succeed, you succeed. What is your method to help someone that is struggling in their work?


It becomes almost a business of value, which is we work hard on writing down the tasks in what we call a playbook. Having a reference, or a playbook is what we call it, allows that person to be independent to try to figure it out. If it’s going to take you three hours to figure out, do not do that but they need to try it. They need to be challenged. They need to try to figure it out. If it’s twenty minutes, then we need to figure out a way if we’re not explaining it right because maybe it’s us. Maybe it’s not them. If they do it 2, 3 or 4 times, there’s an issue that needs to be addressed.


NWB 16 | Setting Boundaries
Setting Boundaries: It’s very important and imperative that a manager doesn’t hire necessarily people that they like, but people that can fill in the spots on the team that are weak.


The biggest thing is if you come to anyone with a question, have 1 or 2 ideas on what you either already did, or you could do so that you’re not having the other person solve the situation for you because as a leader, you have your own day going on. If someone comes to you and says, “I have this problem.” “What did you do about it?” “What have you done so I know how to direct you?” It’s that kind of thing. It’s important for them to do a little bit of troubleshooting before they come to you and say, “I need help with this.”


It’s like what you said earlier, no question is dumb. No question is off the table. If somebody needs help, by the time they come to you, they probably have tried a few things. Stacy, this has been such a great conversation, but I do want to pick your brain a little bit further. I would like for you to share a couple of actionable tips that a leader can do in order to lead their team. Do you have a couple of tips that you can share with us?


I do. My favorite tip that has taken me through over 40 years of business is to inspect what I expect. I need to see it, I need to read it, I need to feel it in order to make sure my team is doing the work that I expect to be done in the way I want it done. The second thing is, as women do, we still have a long road ahead to have a real seat at the table. It behooves all of us with our power and our ability to move each other up to do it, not talk about it, but make it actionable. I have done that with many women as they’ve come into our business.


The insurance business is an unbelievable business for women. It allows you some flexibility and the ability to help people while making a nice living. Everyone needs to find that niche that feels right for them, but if you feel like you’re at a dead-end, now is the time to go out and look for a different job. You can be good at it and bring women around you that can bring you up that can help you.


Those are amazing tips. I love it. The second one I love more because they say that the five people that you surround yourselves with are what you’re reflective of. For those reading, if you’re in a job that you’re not happy with, then do something different. The definition of insanity is to do the same thing over and over, and expect a different result. Do something different. Ask people. There are tons of women. Stacy, is there anything more you want to do about what you offer in your business or anything like that?


For women, we’re going to spend some real time teaching women about finance and risk. A lot of people don’t understand where they are. We can help you and we can help put you in the direction so that you can feel comfortable in your life. That’s part of what we do.


The only way to empower women is to educate them. – Stacy Kahan Click To Tweet


I love that, Stacy. Thank you so much. Everybody, that is a wrap. Thank you so much, Stacy, for your time here. I appreciate it.



That is a wrap with Stacy. I had such a great conversation with Stacy. I love her. She is nice to talk to. Stacy was so wise. She brought a tremendous amount of value to you, so I hope you do as well. To recap Stacy’s two tips, the first tip is inspect what you expect. She said that she likes to see, read and feel the work that her team is doing in order to make sure that the team is getting it done the way she wants the work to be done. I think that is a great one because she doesn’t wait until it’s all the way done. She is inspecting it along the way.


Tip number two is as women, we still have a long way to go to deserve a seat at the table as the norm. It behooves all of us to work with our power and our ability to move each other up, not just talk about it but make it actionable. She said to bring women around you that can build you up so they can help you and you can help them in return. If you have any questions about our episode or if you have any suggestions on career development topics that you would like me to cover, by all means, send me an email or a DM. With that, remember to be brave, be bold and take action. Until next time.



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About Stacy Kahan

NWB 16 | Setting BoundariesInsurance is not only in my blood, it’s something I feel passionate about. I get to discover what people’s dreams are – for their businesses and in their personal lives – and then use insurance to help them get there. And I make a firm commitment to absolutely every client: you will walk out the door in a better position than when we met.