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Family Matters II

Walking the Tightrope of the Family Business Transition

Family enterprise transitions can feel a lot like walking a tightrope. The future is unknown and scary. There is so much at stake. What will you do after you leave? Will the family business survive? Will the next generation uphold the family values in a way that honors the family legacy? And like walking a tightrope, the key to success is all in one simple word: balance.

A Delicate Balance Between the Past and the Future

One of the greatest fears that multi-generational family business owners face is whether the whole enterprise will last once they pass the torch to the next generation. Financially speaking, a large percent of family wealth is lost each time it passes to the next generation and is completely gone by the third passing. Unfortunately, the same can happen with the family’s values, as well.

Typically, a lack of leadership and stewardship training, coupled with trust, initiative and communication barriers, are the primary reasons for this unfortunate trend. But family business owners struggle with what they should do (and when) to ensure the transition goes smoothly. Some are looking for a step-by-step process while others throw caution to the wind and “wing it.” And insofar as these approaches go, it’s a mixed bag between those that go well and those that…well, don’t!

While I never like to speak in absolutes, I will say this much: nearly all of the most successful family transitions I have seen are achieved when the current generation is able to balance two things: preparing the next generation and preparing themselves. 

Like so many things in life, mastering the transition of the family business and wealth from one generation to the next is a delicate balancing act. But finding the right balance isn’t just haphazard. It takes careful planning and preparation to get right.

Preparing the Next Generation from Birth

Whether it is easily recognizable or not, children, grandchildren, and other family members are watching and absorbing the way you operate the family enterprise from afar—soaking up little bits of information here and there as they are exposed to the operations. But have they learned the right lessons? Have you taught them all they need to know to take over the family business with relative ease?

The truth is it can be hard to tell. Some leaders begin the process of a major life transition with complete confidence, only to discover the leaders they had the most faith in were not ready. The opposite is also true. Some leaders have a tough time letting go, only to learn that they had less to worry about than they imagined.

A family that thrives in all generations understands that success is about much more than just financials. It is about both the qualitative and quantitative aspects of life.

Like life in general, transitions are a process that open so many opportunities—opportunities to build on relationships and the four areas of wealth. After all, this is about your family and your values. It is not a business transaction.

Bequeathing a legacy that is sustainable long after you’re gone will require getting the family involved early and often. The sustained engagement over time will ensure you are passing along the seeds of wisdom and guiding principles that reflect and align with your family’s mission. 

Preparing Yourself

After years of planning and successor grooming, the day will finally come when it is time to pass the baton of the family business into the hands of the next generation. Undoubtedly this transition will elicit a host of competing emotions from pride to fear and excitement to anxiety. But not simply because you’ll be transferring what you’ve built over the course of your lifetime to your successors, but because it may be difficult to imagine who you are and what you’ll do outside of your business life. How will you spend the next twenty years? What will your Life 2.0 look like?

It's ok if you can’t answer this right away. It may take some time and soul-searching to finally gain some clarity. But take note of your mindset as you approach the next step. Are you lamenting what is being “lost”, or celebrating what is being gained? Allowing for growth or fixed on the past?

Even though you are leaving your role in the business, it doesn’t mean you have to give up the side of you that thrives in this environment. Nor do you have to abandon or ignore the parts of your identity that are tied to your business-centric talents. In fact, we recommend you don’t.

Instead, use your skills, experience, and expertise to capitalize on new possibilities. We like to use the Six Elements of Wealth to help our transitioning business owners brainstorm ways they can put their talents to use. We find this helps them to focus on what can be, rather than what has already been.

Embrace the Next Step—Even if You Feel a Little Wobbly

People tend to resist change because they fear they will not be able to adapt to new ways. Oftentimes, they also fear that they will lose something of value. In the case of business transitions, this sense of loss can be particularly poignant.

We have found that our WillKate clients find Life 2.0 far more rewarding when they have visualized and imagined this next chapter ahead of time—for both themselves and the next generation of family leaders. What will your transition look like?

If you’re interested in learning more about our exclusive work with multi-generational family enterprises, we encourage you to download our more extensive guide here.


A vibrant scene, a vibrant community


At the top of Manhattan, above Central Park, near the corner of West 126th Street and Malcolm X. Boulevard, the heart of Harlem is bustling with life.

On the west side of the street, in the shadow of the legendary Apollo Theater, a young busker sings church hymns as onlookers nod in approval. On the east side of the street, in front of Chef Marcus Samuelsson’s fancy Red Rooster restaurant, a group of about a dozen people hug goodbye after a meal.

A Dodge Charger zips north, blasting Tupac out the windows. A panhandler begs for money or food.

This vibrant scene, this cross-section of humanity, is a perfect representation of the different facets of one of New York’s must storied neighborhoods. It’s no wonder that a sign on the nearest lamppost indicates the action is unfolding on a section of concrete named Sylvia P. Woods Way.

Sylvia Woods, the “Queen of Soul Food” who died in 2012 at the age of 86, was an icon in these parts — the matriarch of a family, the founder of a food empire and the face of a neighborhood.

She was active in the church. She was a philanthropist. She knew everybody, and everybody knew her.

Sylvia was perhaps best renowned for her eponymous Sylvia’s Restaurant, which she opened in 1962. Her family risked just about everything to open the restaurant — literally, they mortgaged their farm. The gamble paid off. Since a glowing review in New York magazine in the 1980s, the eatery has flourished and expanded over the years; it continues to serve fried chicken, ribs, collard greens, cornbread and other delicious soul food with the same recipes from the very beginning.

Though Sylvia is gone, her children and their children now run the restaurant, carrying on the family business and preserving Sylvia’s legacy for the future. Kenneth Woods, her son, serves as chairman and president of the family business. He says his mother made it easy for the next generation to carry the torch.

“Everything she did, she did with dignity, charisma and grace,” Kenneth says. “She worked hard and talked to everyone like they mattered. These remain the things we strive to achieve here every day.”

Crizette Woods, her daughter and vice president of human resources, agrees.

“Mommy would always say, ‘If you don’t love people, this is not the job for you,’ and I think she meant that in her soul,” said Crizette, who also serves as controller. “She also loved making people happy. If she walked through the dining room and someone didn’t seem pleased, she’d come over and do whatever she could to make it right. She was the same in the community, and in return they loved her for it.”

Farm life to Harlem

The story of Sylvia Woods is everywhere at Sylvia’s Restaurant: in the menus, on the walls and as part of the conversations that servers start when they come by to take orders.

The narrative is as much a part of the experience as the hot sauce.

Sylvia grew up the daughter of a widow in segregated South Carolina, toiling away on her family’s farm in Hemingway. Like many, she came to New York for a better life — she had been a hairdresser in her hometown but wanted more. Also, she and her husband, Herbert Woods, wanted to escape the prejudice of the South. They arrived in Harlem in 1944.

Sylvia knew how to cook — her mother and grandmother had taught her — so after a few years of working factory jobs in Brooklyn, she sought a job at a restaurant.

Her first gig: waitress at Johnson’s Luncheonette on Lenox Avenue and West 127th Street. Woods was a hard worker, always going beyond what was asked. She often was the first one there in the morning and the last one to lock the door at night.

Sylvia had worked several years at Johnson’s, and the owner, Andrew Johnson, wanted to move upstate and open another business, so he asked her if she wanted to take over the restaurant. Of course, she did. Sylvia convinced her mother to mortgage the family farm in South Carolina, and she used the collateral to buy the restaurant. Sylvia’s restaurant was born.

The move was quite a gamble — Sylvia’s mother believed so strongly in her own child that she was willing to risk everything to pave the way for success.

According to Tren’ness Woods-Black, Kenneth’s daughter who now serves as “queen of hospitality,” her grandmother’s entrepreneurialism was significant for another reason — in 1962, it was practically unheard of for a Black woman to step out and start a business completely on her own.

“My whole life, I always have known and understood that Black women were these superheroes in a way, amazing multitaskers,” Woods-Black says. “The ability to take care of their families, build business, build community. That’s all I’ve ever seen, and that example has inspired me to become the person I am today.”

Building a dream

That first iteration of Sylvia’s Restaurant was small — 15 stools and six booths.

The restaurant changed addresses in those early years, moving from one space to another as Sylvia got her bearings and the restaurant grew.

Kenneth says his mother was always saving money, and she quickly figured out how to make the most out of every dollar earned.

“She had this unusual way of always being able to budget for everything,” Kenneth remembers. “She had no financial degree, but she could have gone to Harvard.”

Eventually, Sylvia bought most of the stores on the block. Sylvia’s restaurant expanded to fill the space.

Over time, Sylvia’s restaurant became a gathering place for African-American luminaries such as Aretha Franklin, the Rev. Jesse Jackson, Denzel Washington and Jay-Z. That New York magazine review in the early 1980s brought white customers in droves, too — despite the plethora of dining options across the metropolitan area, it seemed everyone wanted a taste of the best soul food in New York.

Sunday brunch was always a big event at Sylvia’s restaurant, as many members of the local community would come straight from church. This meant a dining room full of customers wearing their Sunday best.

It also meant epic hat-watching, as many Black women wore elaborate hats to church.

This reporter frequented the restaurant in the late 1990s and two things were always certain: (1) Everyone left full, and (2) Sylvia was always patrolling the dining room floor, introducing herself, interacting with guests, making diners feel at home.

Taniedra McFadden, executive chief of staff for Sylvia Woods, Inc., says this vibe was vintage Sylvia.

“The essence of Sylvia’s restaurant always has been one of welcoming, love and appreciation,” says McFadden, to whom Sylvia was a great-aunt. “You came in and you were coming into Sylvia’s house. She treated you as if you were dining at her kitchen table, communicating with you and talking to you as if you were in her home. This was who she was. For all of us.”

Making a difference in the community

Today, Sylvia’s restaurant is much more than just a place to eat. It is a community gathering spot, a beacon of hope, a gateway for joy. At last check, Sylvia’s restaurant had more than 80 full- and part-time employees, making it one of the largest employers in the Harlem Empowerment Zone.

It’s also a hotspot of philanthropy. Two of Sylvia’s favorite sayings were, “You can’t beat me giving,” and “A closed hand doesn’t work for me,” and in 2001, the Woods family created the Sylvia and Herbert Woods Scholarship Fund. To date, the fund has awarded more than $500,000 in college scholarships to more than 150 students from Harlem and surrounding communities. The Woods family also has offered emotional and mentoring support to the students for the duration of their college life and beyond.

(The kids say these non-monetary efforts embody a third Sylvia slogan: “Each one, teach one.”)

As part of her effort to be queen of hospitality, Woods-Black represents Sylvia Woods, Inc., on eight different nonprofit boards across New York City.

She is culinary co-chair for NYC & Company, the Big Apple’s official marketing, tourism and partnership organization. She is one of the executive board members for the New York City Hospitality Alliance. She also represents the culinary industry on the board of directors at the She Can Foundation, which supports women-owned businesses.

“I strive to make sure we are always a symbol of success for Harlem,” Woods-Black says. “That’s how I embody my grandmother.”

The Sylvia Woods legacy of kindness lives on in other subtle ways, too. On a recent summer night, several members of the neighborhood’s unhoused community came by the restaurant around closing time seeking leftovers. Without hesitation, employees doled out items until the stash was gone.

The younger generations

Family always has been a part of the equation at Sylvia’s Restaurant — Sylvia herself said family was a key motivator.

All four of her children worked in the restaurant as they grew up — first as potato-peelers, bussers and dishwashers, then as servers, hostesses, sometimes even cooks. When they became parents, their kids worked in the restaurant as well. Most of the Woods children and grandchildren share vivid memories of eating family dinners at a big round table in the restaurant on Sundays. That table — Table 35 on the formal seating chart — was still on the dining room floor until recently.

Gradually, as Sylvia aged, her children took over different parts of the business. Kenneth became president. Crizette took over HR. Van, another brother, has managed real estate acquisitions. Grandkids got into the mix, too: De’Sean Woods, Kenneth’s son, now serves as CEO; Woods-Black, De’Sean’s sister, manages the company’s relationships with guests and the community.

When Sylvia Woods died in 2012, a succession plan was already in place. Though everyone in the company felt her loss acutely, though her absence in the dining room was noticeable, the business was able to continue uninterrupted.

“We’ve carried on, but sometimes we still can’t do everything she did,” Kenneth jokes respectfully.

One thing the younger generations have been able to do: grow the empire. The parent company of Sylvia Woods, Inc., now comprises the restaurant, a full-service catering hall down the street, Sylvia’s Catering and Special Events division, a nationwide line of Sylvia’s food products and a real estate holding company.

Today, whenever a new employee joins the team, that person is required to watch a 15-minute video composed of news and interview clips from the 1970s, 1980s and 1990s — snippets that tell the Sylvia Woods story from beginning to end. It unfolds like a short documentary film.

The Woods children and grandchildren put together the video to make sure new employees who didn’t know Sylvia in person can understand the passion and charisma that made her so special.

Sylvia appears so many times in the video, it’s almost as if she’s still alive.

For Woods-Black, her grandmother’s legacy, coupled with the cultural legacy of soul food, keeps the past current.

“Soul food is one of the most important cultural identity markers for Black Americans,” she says. “The recipes, the ingredients, the communal feeling, the accessibility — all of that is part of a tradition we were able to maintain even through the Middle Passage and the other great migration from the South to the North.”

What’s next

After surviving the Covid-19 pandemic (and enduring major renovations in the restaurant during most of 2021), the younger generation is primed to take the Sylvia Woods legacy to new heights.

McFadden says Sylvia Woods, Inc., has been looking at opportunities to expand the restaurant with other locations in the United States and abroad. She adds that the parent company also has kicked tires on adding more SKUs at the food products company. Even the real estate company is growing, with new development projects in the works for 2023 and beyond.

The year 2022 marks De’Sean’s first year as CEO. At press time, he said he was looking forward to kicking off a 60th anniversary celebration on August 1 that will last the entire year. De’Sean says that when he thinks about the future, he tries to see it as his grandmother would have: with growth, but also with humility.

“I won’t be here 60 years from now, but I’ve got to approach it the way Sylvia did and focus on what I can do now to make sure our family’s legacy lives on,” he says. “There aren’t many places like this one left in the world, and there certainly aren’t many businesses that are as closely connected to the community as ours. That means it’s even more important for us to do what we can to keep it going. The way we see it, we’re not just maintaining a restaurant and a business. We’re keeping a culture alive.”  nFB

Matt Villano is a writer and editor in Healdsburg, Calif. Learn more about him at


Keeping it all together

My great-grandfather Titus Schmid, the founder of Crescent Electric Supply Company, emphasized that people were the lifeblood of the company — not just its employees and customers, but all stakeholders in the communities it serves. His efforts in bringing Crescent to life and steering it through wars and downturns laid the foundation for a multigenerational family business.

Crescent has come a long way from its inception in East Dubuque, Iowa, in the early 20th century. Today, it serves electrical supply customers nationwide and has remained family-owned as the Schmids have expanded to five generations.

Titus’s role as a founding entrepreneur was entirely different from that of descendant shareholders like me. Since his time at the helm, each subsequent generation has had unique challenges to overcome and, so far, each has stepped up to the plate.

From my vantage point in the fourth generation, Titus’s entrepreneurial zeal can sometimes feel like ancient history. Maintaining that connective entrepreneurial tissue as the family expands across the country is the challenge we on the family council now face, and it’s not always easy. Formalized governance and strong in-law contributions have been key pillars for keeping the family and business relationship humming, but come with their own thorny issues.

Balancing formality and fun on the family council

When I first joined our council, I assumed that the company had given the third generation (3Gs) a clear roadmap for establishing bylaws, processes and whatever else they needed to get it up and running.

I quickly learned that no such map existed — it instead took significant work from founding council members like Kathy Munson and Mary Daugherty to get it off the ground. Mary is a professor who studies family businesses, and her determination to form a council to facilitate family-business relations was a crucial catalyst behind its creation. Without her urging, who knows what the council would look like today, or if there would even be one.

Maintaining formal governance in a fun environment is a balancing act we on the council are constantly monitoring. We try to not take ourselves too seriously while pushing the envelope on making things better for the family. And we’ve been busy lately — initiatives like a new online document storage and communications platform, an employee assistance fund and life-stage education materials show that we’re not satisfied with the status quo.

In my role as chair of the education committee, the greatest challenge I face is getting other 4Gs (and, as they get older, 5Gs) involved. An educated and active family shareholder base is a harbinger of our future success, but it’s hard to overcome time and physical distances. Prior generations of Schmids had Crescent interwoven into their daily lives — most were concentrated in the Midwest, near family members who worked at the company. Today, most 4Gs live far away from Dubuque and have little day-to-day interaction with the company or each other.

To strengthen the link between us, we’ve set up 4G gatherings via Zoom to catch up with each other and ask questions in a supportive environment. We’re continuing to bolster education materials that help all shareholders learn about the history of Crescent and how the company operates today. Participation in the remote gatherings is lower than where we’d like it to be, so we’re trying new approaches like an Instagram account to connect with younger cousins.

All told, a formal governance structure via the family council and proactive initiatives have helped us maintain solid family harmony. Ensuring that the entrepreneurial fire keeps burning with subsequent generations will be a challenge, but I believe we have the structures in place to make it happen.

In-laws are one of our greatest assets

Thank goodness for our in-laws. They’ve been an incredible asset to our family.

Currently, our three family board members are all in-laws, as are many members of our family council. As the family grows, by definition there will be more in-law shareholders, and I’m looking forward to the talent we’ll be bringing in.

In our council charter, we state that our governance is based on principles, not personalities. This has given way to a meritocracy where well-qualified, motivated individuals are welcomed with open arms, regardless of blood relation or in-law status. While there are many capable cousins in our ranks, input from in-laws has been vital to the success of the council and business alike.

I’m getting married next year and am excited to welcome my fiancée into our family. But at times, it’s been overwhelming for her. Discussions around finances, introductions to dozens of cousins, and learning our governance structure is a lot to digest. There are many things I wish I’d done differently in order to make her feel more comfortable amongst our big family. In particular, I should’ve been more aware of the overwhelm she was understandably feeling.

Empathizing with her concerns has given me a view from the outside, and I’m increasing my efforts around in-law onboarding within the education committee to make the process smoother. Sacrificing future in-law contributions because of an overwhelming onboarding process isn’t an option.

As my younger cousins start to marry, their spouses will likely face similar challenges. Listening to experiences from in-laws and course-correcting as necessary will help us ensure their valuable contributions continue.

Keeping it all together

My great-grandfather built an electrical supply business from scratch. His children worked to keep it alive and growing. His grandchildren grew it further, and formalized family and business relations.

Now, we 4Gs are tasked with keeping it all together. As more and more 3Gs reach retirement age, it’s time for us to take on our unique challenge of maintaining connections with each other and to Titus’s original mission.

It’s not going to be perfect, so relying on our shared entrepreneurship will be key moving forward.

Charlie Rhomberg is a freelance writer based in Iowa.