I’ve been lucky enough to work daily with my son, Charlie, at CRE OneSource for the past 4 years. Spending time together, aligning goals, and watching him grow as a professional has been one of the great privileges of my career. But let’s be honest—working with family comes with both highs and lows, and it takes intentional effort to navigate the line between business and personal life.
— Shared Vision, Daily Connection: One of the biggest gifts of working with Charlie is the time together. Whether it’s short-term problem solving or mapping out five-year goals, we get to build something meaningful together. That kind of shared mission brings purpose to both our relationship and our business.
— The Joy of Watching Him Grow: I get a front-row seat to watch Charlie level up. I see how he thinks, adapts, and builds relationships—skills that take years to master, and he’s developing them in real time. As a father, that’s priceless.
— Navigating the Cons with Boundaries and Clarity: Working with family can blur boundaries. Disagreements at work can spill over into other conversations, and emotions run deeper. The article below nails it: success comes from defining roles, setting boundaries, and having the discipline to treat each other like professionals at work. One time, Charlie said: I need a father right now, not a boss. And he was right.
Working with family can be a double-edged sword—but with the right mindset, it’s a powerful one. Create clear expectations, honor each other’s growth, and don’t forget to enjoy the journey. Because in the end, this is about more than just business—it’s about legacy.
Here is a photo from a trip we’ve taken together—where we were able to step back, relax, and set goals away from the daily grind.
A Glacier in Norway
Click here to view the full-size image.
The Fantastic Life Rule #3:
Build Your Resumes Every Year
Working alongside Charlies has brought me a big win—I get to work on both my family resume and my work resume at the same time. Finding ways to layer your resumes is a great trick to consistently leveling up.
The pros and cons of working with family
Two professors break down how to navigate the benefits and challenges of working with family members.
[Source Photo: Getty Images]
By Alfredo De Massis and Emanuela Rondi
Working with family members in a business setting is a unique experience that brings both opportunities and challenges. Entrepreneurial families—those engaged in creating and managing businesses over generations—often rely on the strength of family ties to create long-lasting ventures. However, combining family and business dynamics introduces complexities that need to be managed in order to avoid heaven becoming hell.
Fortunately, by understanding the potentially difficult dynamics of working with relatives, you can navigate potential pitfalls and increase your family business’s odds of long-term success.
Here are the key advantages and disadvantages of working with relatives:
The pros of working with relatives
1. Strong trust and loyalty
2. Shared vision and values
Family businesses often benefit from a strong, shared vision that unites family members around a powerful sense of purpose. This shared vision drives both the business and the family forward. When family members share similar beliefs about what they want to achieve (e.g., commitment to quality, customer service, and/or ethical practices), decision-making becomes more cohesive and unified. This alignment of values can set a family business apart, creating a unique culture and identity that resonates with both customers and employees.
3. Long-term commitment
Family members often have a vested interest in the business’s success over the long term, as the company is not just a job but a representation of the family’s legacy. This long-term commitment means that family members are more likely to make sacrifices for the good of the business, such as reinvesting profits instead of taking dividends or working extra hours during challenging times. This perspective encourages sustainable growth rather than short-term gains, helping family businesses weather economic downturns and build a resilient foundation for future generations. The motivation to pass on a healthy business to the next generation can drive family members to make decisions that protect and preserve the business over time.
4. Flexibility and support
In family businesses, members are often willing to step into various roles or take on additional responsibilities to keep the company running smoothly. Family members may support each other through personal and professional challenges, providing a level of flexibility and understanding that might not be found in nonfamily businesses. This adaptability can be especially valuable in smaller or growing businesses, where resources are limited, and everyone must wear multiple hats. Additionally, family businesses often provide a supportive work environment that encourages family members to develop their skills and talents, knowing that their success directly contributes to the family’s legacy.
The cons of working with relatives
1. Blurring of professional and personal boundaries
One of the biggest challenges in working with family members is maintaining a clear separation between personal and professional lives. Family dynamics—such as sibling rivalries, parental expectations, or longstanding disagreements—can easily reverberate into the workplace, complicating relationships and decision-making. And vice versa, disputes in the working environment can be brought home, rusting family relationships. Without clear boundaries, work-related issues can strain personal relationships, and personal conflicts can negatively affect business performance. This blurring of personal and professional lines can lead to stress, resentment, and even burnout if family members feel they can never truly leave work behind.
2. Resistance to change and innovation
Family businesses often emphasize their tradition and heritage, which can sometimes lead to resistance to change. In a business where legacy and continuity are prized, family members may be reluctant to challenge established practices or explore new opportunities. Younger generations may find it hard to introduce fresh ideas or new technologies if the older generation holds strong to “the way things have always been done.” Over time, this reluctance to evolve can hinder growth, discourage the next generation’s involvement, and leave the business vulnerable to competition from more adaptable companies.
3. Nepotism and lack of accountability
Hiring and promoting family members can, perhaps unsurprisingly, lead to issues with nepotism. Family members may be placed in roles for which they are unqualified, creating an environment where performance and merit are overlooked. This can undermine the morale of nonfamily employees, who may feel that their hard work goes unrecognized due to favoritism and family logistics. Additionally, family members may feel immune to accountability, knowing that their job security is closely tied to family ties rather than performance. This ultimately can affect the business’s productivity and reputation.
4. Succession and ownership disputes
Succession planning is a critical issue in family businesses, and disputes over leadership or ownership can create significant challenges. Different family members may have competing ideas about who should take over the business or about how the business should be run. These disagreements can lead to family rifts, lawsuits, or even the dissolution of the business if conflicts escalate. Without a clear and agreed-upon succession plan, family businesses may experience instability when it’s time for leadership to transition. This lack of planning not only affects the family but can also create uncertainty for employees, customers, and business partners.
How to navigate the pros and cons of working with family
While there are both pros and cons to working with relatives, many of these challenges can be addressed with thoughtful planning and communication.
For instance, establishing family and business governance structures can help ensure communication and setting up boundaries. Clearly defining roles and responsibilities ensures that each family member understands their position within the business, reducing conflicts over authority and expectations. Regular family meetings, where each person has the opportunity to voice concerns and share ideas, can help prevent misunderstandings and foster unity. Additionally, engaging external advisors can provide unbiased perspectives that guide the family through complex issues such as succession planning, wealth management, and governance.
Working with family members offers unique benefits, from trust and loyalty to long-term commitment. However, it also presents distinct challenges, including blurred boundaries, nepotism, and succession disputes. How families navigate these challenges can make all the difference.
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ABOUT THE AUTHORS
Alfredo De Massis is a Professor of Entrepreneurship & Family Business at the D’Annunzio University of Chieti-Pescara and IMD Business School, who serves as adviser to entrepreneurial families and policy makers. Ranked as the leading family business academic globally in a 2024 study published in Small Business Economics, Alfredo was included in Family Capital’s list of Top 100 Family Business Influencers in February 2022, for the strong influence of his thought leadership on the global shaping of the family business field, and, in September 2022, Family Business United inducted him into The Family Business Hall of Fame, recognizing exceptional individuals within the family business sector More
Emanuela Rondi is an Associate Professor at the Department of Management at the Università degli Studi di Bergamo (Italy). After graduating in Management Engineering, she got her PhD on Family Business Management from Lancaster University Management School (UK) More