How To Work With Your Sister & Keep The Peace: 5 Families Spill

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Sisters may very well be the original frenemies: Love them one day, hate them the next. Of course, growing up with a sister is one thing; after all, age often leads to friendship and a decline in hair-pulling. Starting a business with a sister, however, is a different story. “All leadership teams have communications challenges,” Sharon Richmond, an executive coach who works with business leaders, tells us. “But, I’ve found the closer the team members are, the more intertwined their relationships, the greater the challenges can be.” Translation: The more complex the relationship, the messier conflicts can get.

And, with family, there’s a higher risk. Not only is your business on the line, but so is your relationship. In some cases, sisterhood can be an asset. “Who knows you better than your sibling? And, if they’ve got your back, don’t you feel totally trusting and safe?” Richmond says. In other cases, sisterhood — and the inability to get past sibling love/hate — gets in the way.

How does one balance the family and business? We chatted with sister acts in fashion, music, and more to reveal the secrets to success.

SayLouLou1Photo: Courtesy of Say Lou Lou.
Company: Say Lou Lou
Sisters: Miranda and Elektra Kilbey, 22

Do you think being twins helps or hurts?
Miranda Kilbey: "We’ve gone through all our lives at the exact same age and seeing everything through the same point of view, so sometimes it’s way easier because we know each other so well — we have similar ideas and references. Sometimes I do wish there was a natural hierarchy between us. Normally, an older sister has authority, but for us we’re always fighting for the power. Although, with any siblings, there’s fighting for who gets to decide things, but for us there’s not one person looking after the other."

I suppose that makes it easier to decide things equally.
Miranda: "Yeah. If I don’t like an idea straight away, I would just say no. And, some days in the studio it feels like any idea I come up with she’s like, 'I don’t like it.' So, you keep pushing each other’s buttons, and it’s like, 'Oh, f--k off.' But, with a friend, we would have to sugarcoat it. So, we hate and love each other, but there’s pure honesty between us. I don’t think I can get that with anyone else."

Aren’t you afraid of getting tired of her?
Miranda: "Mmm…I’m already quite sick of her, but I can’t get rid of her now! It’s too late. Before this, we were always quite separated, and we still have our own lives and identities and schedules. It can get very intense because we’re working and living together 24/7 now. So, we have to say, 'All right, you go to the movies; I’m going out with a friend.' We have to go separate ways."

So, how does the sisterhood work with the music?
"It’s in the essence of how our ideas and harmonies come together really well. You can hear the sisterhood in our voices and how that sits on the melodies."

Is there a moment you realized it was the best idea ever?
"Maybe the first time we performed together. We just looked at each other, and we knew we were feeling the same thing, the same feeling of excitement. We can communicate without ever saying anything."

What’s the secret to success?
"I think the secret is really sharing the passion and really feeling that there is no other way you could make it without her. You have to love something so much that you need her there; otherwise, it won’t work."
GeorgetownCupcakesKatherineSophie4Photo: Courtesy of Georgetown Cupcake.
Company: Georgetown Cupcake
Sisters: Sophie LaMontagne, 36; Katherine Berman, 34

You both quit your jobs in finance and fashion to open this bakery. What made that happen?
Sophie LaMontagne: "When we were young, [we] would say, 'One day, we’re going to open a bakery together.' And, we kept talking about it and talking about it, and then we just thought, 'What are we waiting for?' That was a very scary decision, and to have a support system like your sister was very helpful."

How has the sisterly bond served you in business?
Katherine Berman: "We don’t even have to finish each other’s sentences. The minute she comes in, I know what kind of day it’s going to be."
Sophie: "At the same time, we always tell people it isn’t for everyone. A lot of family businesses don’t survive, and members don’t speak to each other, so it takes a certain type of relationship. But, for us it works."

What’s the type of relationship that works?
Sophie: "We fight, and 10 minutes later we’re fine. We’ve had this relationship our whole life, so we’ve developed a pretty thick skin. You can’t have this open relationship with friends and coworkers, and it really does give you an edge. There’s no politics or worrying."
Katherine: "With your sister, you know what buttons to push, so we do that all the time. But, you can do that and in some respects still get away with it. Your sister sees all your flaws, and she accepts them, and she can forgive you unlike anyone else."

Do you still act like an older sister and younger sister in the business?
Sophie: "Katherine will accuse me of playing older sister all the time, just assuming that I’ll get my way. I use it to my advantage, when I want something to be rammed through. And, Katherine, she’ll play the little-sister card. Whenever she doesn’t want to do something, she’ll come to me and say, 'Well, you can do it better than I can, so why don’t you do it?'"
Katherine: "But, I do legitimately think that you can do it better!"

So, what advice do you have for sisters who want to start a family business?
Sophie: "Sit down and have a frank conversation. Some sisters know inherently that they can work together, and some know they can’t. You need to ask, 'Do we have thick enough skin?' And, you have to ask yourself if you want to spend every day with your sister. If the answer is no, then you shouldn’t, because having a business is 24/7 and you will spend all day, every day, with your sister.
Katherine: "It can either be a blessing or a curse."

Was there a moment when you realized it was the best decision you ever made?
Sophie: "The first day we opened in Georgetown. When we made the decision to quit our jobs, many people were not supportive. So, when the line went down the block the first day, it’s like we proved it to ourselves, and we proved it to everyone else."
Dalaga-Sisters-Michelle-(Left)-Mary-(Right)Photo: Courtesy of Dalaga.
Company: Dalaga
The Sisters: Mary Mangiliman, 31; Michelle Mangiliman, 33

When did you guys decide to start working together? 

Mary Mangiliman: "When Michelle went off to college and we were apart for the first time. We knew that there was no way we could live without being near each other."

Since then, you started a clothing line in 2004 and opened Dalaga in 2006. Has it always been smooth?
Mary: "At first, we were so young, so it was all fun and games. But, when we opened the boutique, we were in our early 20s, and we were both coming into adulthood and living together. So, we definitely had really bad times; we couldn’t even be around each other some days. There was a little power struggle at first."
Michelle Mangiliman: "Dalaga has always been my baby, and as a designer, I knew what I wanted everything to look like, so it felt natural to me to always make the decision. It was really hard for me to be level-minded with my sister and be like, 'Okay, we’re equal partners.'"
Mary: "In 2006, I took a two-year break from Dalaga, and then I came back, and it became stronger."
Michelle: "We got all this press in 2009, and I knew I couldn’t handle it myself. I realized how much my sister could help me in this, how much we needed her."

What changed the second time around?
Michelle: "We both just grew professionally. She worked in a corporate office, I managed the employees on my own, and we came back with a better understanding of how we should be more patient.
Mary: We also listed out everything each one of us is responsible for and made it more equal. I made sure Dalaga would be my baby as well."
Michelle: "We love working with each other, because you trust your sister and you love your sister, but you have to define who has control over what."

Do you guys still feel like the older and younger sister?
Michelle: "Professionally, I don’t feel like I’m the older sister anymore. But, outside of the store, I’m still big mama, I’m still taking care of my little sister."
CoffeeMeetsBagel-KangSistersPhoto: Courtesy of Coffee Meets Bagel.
Company: Coffee Meets Bagel
Sisters: Arum and Dawoon Kang, 31; Soo Kang, 33

You started working on the dating website Coffee Meets Bagel in 2011. Has your working relationship changed since then?
Soo Kang: "In the beginning, we were really small, and we all wanted to be involved in everything together, so it was very hard, and we fought a lot. So, now our roles are clearly defined."
Arum Kang: "I do product design, Soo does the creative design, and Dawoon does marketing, social media, and business development. Ultimately, we get the final say in each of these areas."

How did you deal with the initial fights?
Dawoon Kang: "It’s definitely still a work in progress. We actually brought in a leadership coach who came in and spent six hours with us."
Soo: "She had us take the Myers Briggs personality test."
Dawoon: "All of us are Es and Js (extroverts and judging), which means we’re all very vocal, which is why we fought a lot."
Arum: "The coach also asked us to look at objects in the room and describe them. I described a fish bowl with plants and different-sized pebbles. Dawoon wrote something like, 'This feels like I’m looking at a jungle, and some animals might come out at any moment.' And, it’s like, Oh my God. We’re seeing the same things but interpreting it very differently."
Dawoon: "Just knowing that other people are not crazy, that they’re just different people, really helps a lot."

What came out of the coaching session? Any practices?
Dawoon: "At the end of each day, we spend 10 to 15 minutes discussing personal issues that came up during the day, so we can start fresh."
Arum: "We call it the 'Clean Slate' meeting."

Is there a moment when you realized that working with your sisters is the best idea ever?
Dawoon: "I come across a lot of start-ups that implode because founders don’t have trust in each other, and whenever I read these stories, I think, 'I’m so happy that I’m working with my sisters.' I never have to doubt their intentions, which can be a huge distraction."
Arum: "People underestimate how much of that impacts start-up dynamics. Usually, start-ups fail because of founder conflict or loss of money. Start-ups die when founders give up. So, when you’re sisters, you can’t just give up, and that’s really powerful."

Any final advice for upcoming sister acts?

Dawoon: "Get a clear division of roles and agree on it up front. Whoever has leadership has the final say. Otherwise, you’re just going to fight to death. And, make sure you talk about equity stake. It’s a sensitive topic, but get an idea."
WilliamOkpoPhoto: Courtesy of William Okpo.
Company: William Okpo
Sisters: Lizzy Okpo, 23; Darlene Okpo, 27

So, who came up with the idea for William Okpo?
Lizzy Okpo: "I did. I wanted to start a line before I turned 21, and I thought, 'I should do it with someone who knows me well, and who better than my own sibling?' You often hear that family can’t do business, but in my family, it’s the opposite. We probably have more issues doing business with outsiders than our family. Trust is such a huge thing to us. No matter what we can’t run away from the responsibilities. We have to carry each other."

Don’t you ever get tired of your sister, though?
Darlene Okpo: "We had to learn that we’re human, and, even though we’re family, we’re not operating 24/7. We live together, we eat together, so sometimes we have to shut down from each other and breathe. Like, yesterday, I was like, 'All right, don’t talk to me.'"
Lizzy: "And, you can’t take it personally."

Does that stop the fights?

Lizzy: "We will never get past that. We probably get in an argument once a day. We once had an argument where we yelled at each other for three hours straight. No one backed out, no one walked away from the conversation. The only way that ended was because somebody picked up the phone to call our [two older] siblings."
Darlene: "It’s better because we have people around us who are able to mediate the situation at all times."
Lizzy: "I hate to say it, but it’s always another person to remind us to shut up, that we’re overreacting."

But, of course, that’s all worth it in the end.
Lizzy: "Absolutely. Certain things can come out of context with other people, but with Darlene it’s like, 'Oh, I know what you need.' It’s so weird how in sync we are. When someone gets on our nerves, they get on both of our nerves at the same time. I can read Darlene’s face if a meeting isn’t going well, and she can explain what I’m saying to people if it sounds too outrageous. I joke that everything Darlene says begins with 'What Lizzy meant to say is…'"

What’s the best part of working with your sister?
Lizzy: "No matter how much you argue, she’s still there. In an hour, we’ll be talking about TV shows and fashion. I still wake up, and I still see her. And, I have her behind my back no matter what. We are our own team."