Families, Family Business, and the Holidays

It may be natural to talk about the family business—whether long before or during a transition—when family members gather for holidays, but is it smart? 

When families, family business, and the holidays converge, it’s natural and convenient to talk about business because, well, everyone is present in person. Having business-related conversations in person—especially those that relate even tangentially to a one-day transition from one generation to the next— is far more effective than video or audio calls, texts, voice messages, or emails. 

In-Person Interaction 

From life experience we know that setting aside time for face-to-face communication signals that the parties involved care about each other and/or the topic of the conversation. We also know that facial expressions and body language provide real-time feedback related to how the other party is reacting to our words. These cues help us adjust appropriately; perhaps provide additional explanation, clarify our points, or soften our language or tone. 

There’s plenty of empirical data indicating that in-person conversations are more effective than any other form of communication. 

• A Stanford Business School study found that participants in in-person meetings generated 15% to 20% more ideas than those communicating virtually. 
• A study by the Harvard Business School reported that 95% of its participants said that face-to-face meetings are a key factor in building and maintaining long-term relationships. 
• Research indicates that face-to-face communication is more successful than email because email restricts “nonverbal cues that generate trust and empathy.” 
• According to Adobe’s 2022 U.S. Emoji Trend Report, 47% of survey respondents have sent an emoji that was misinterpreted or taken out of context. 

As effective as in-person conversations are, conversations related to a family business can be problematic at family gatherings. 

Seats for Everyone at the Family Table 

Imagine the typical holiday dinner table. You’ll see parents and children, and possibly grandparents, aunts, uncles, and cousins. If children are college-age or pursuing their careers (inside or outside the family business), there may be spouses, significant others, girlfriends and boyfriends seated at the table as well. 

The purpose of holiday meals or the activities surrounding them is to include everyone, catch up with each other, and make everyone feel welcome and at home. Family time is a unique opportunity to talk about our interests and dreams, swap stories, express pride in each other, relax and have fun. We gather to simply be family. 

Although some of these  are goals of operating, transitioning or even discussing business, not all of them apply in the same context. Not everyone at the family table is involved in the business. Some may be too young, so not interested in the topic and likely annoyed that Grandma, Grandpa, Mom and Dad aren’t paying attention to them. To try make everyone feel included, one (or several) of the grownups will often change the subject to shift the focus away from the business. 

When business topics almost inevitably arise, even those who are interested, but not directly involved, in the business (e.g., spouses) may have no context for the issues being discussed. They don’t know the history behind the issue and likely few of the people involved. It’s not surprising then, that they often make incorrect assumptions about others’ intentions or jump to conclusions that are wide of the mark. 

Drawing the Line Between Family and Business 

Holidays really aren’t the ideal time to talk about business unless you designate a time—away from the family table—to talk shop. This strategy appeals to families for whom getting together at another time of year is practically impossible. Vacation time for adult children—whether in college or in careers—is limited, and married children typically spend the vacation time they do have with their children and /or divide it between two sets of parents. 

Setting Aside Business Time 

There are many advantages to setting aside time to gather only the people immediately involved with the family business. 

First, finding a time and venue separate from the family dinner table eliminates the problems mentioned above: (1) boring or neglecting the youngest family members (or even some of the oldest!); (2) providing only enough information for some to make assumptions that just aren’t true or jump to the wrong conclusions. 

Second, in family-owned businesses, those involved have two hats in their closets: their family hat and their business hat. For example, a daughter’s family hat may be “youngest child” while her business hat is “most promising successor.” At family gatherings when business is discussed, there is uncertainty about which hat a person is wearing. It’s not always clear which hat is on one’s own head and far from clear to others what hats others are wearing. For example, is Dad’s wearing his business or family hat when he comments about a child’s performance or potential? When Dad says he’s proud of his oldest son’s GPA, the son might hear that he’s a shoe-in for Dad’s job. The daughter who also hears the comment might assume that her father plans to appoint her brother as one-day CEO, so she begins to think seriously about changing her major from accounting to political science. 

Third, there’s no time limit on a family dinner, no agenda and multiple conversations happen simultaneously. In family meetings, however, conversations focus solely on business, and there’s a set time limit and, often, an agenda. When meeting time is limited, participants know they must speak up before the meeting ends. Everyone at a family meeting knows that everyone is (or should be!) wearing their business hats. Participants are typically more willing to speak candidly—businessperson to businessperson. Finally, the rigorous debates that are healthy at family business meetings can be impossible or very uncomfortable at the family dinner table. 

Family Meetings 

Family-business-focused meetings are new for many families, so we’re often asked for tips on how to make them effective. Here are a few ideas to think about and adapt to your family. 

1. Parents of adult children often use estate planning as a springboard to talk about their businesses. Estate planning is, by definition, future focused, and, since the family business is often a couple’s or family’s most valuable asset, the topic of the future of the business arises organically. Simply informing children that an estate plan is in place demonstrates that parents have thought seriously about their own future as well as the future of their children and the family business. 

2. Another “safe” topic is philanthropy, either in or outside of an estate planning context. Asking members of the rising generation questions like, “If you had $100,000 to donate, which charity would you pick, and why?” gives parents insights into their children’s interests and values as they mature. 

3. Including “AMA time” or Ask Me Anything on the meeting agenda is another option. Members of the rising generation are encouraged to ask any question of family members currently running the business. We’ve found that free-wheeling back-and-forth AMA sessions yield as many insights as they do surprises for members of all the generations involved. 
4.  To maximize the value of each meeting, we suggest that you (1) make sure to have a communicated purpose for each meeting, (2) organize the agendas to achieve a specific outcome and (3) think of each meeting as a steppingstone on your family’s journey to forging meaningful business and family relationships. . 

Family, Family Business, and the Holidays 

The stated purpose of a family-business-focused meeting is to familiarize family members with the history of the business and look to its future. The invaluable byproduct is that these meetings help all family members appreciate the distinction between the inclusive nature of family relationships and the functional nature of business relationships. When these two relationships are clearly delineated, everyone in the family benefits.  

Make the Most of Your Holidays 

If you’d like to learn more about how to use business-focused meetings to make the most of family time during the upcoming holidays, we invite you to download “The Family Connection Guide: Holiday Edition”. Inside this free guide, you’ll discover:

✨ Clear strategies for setting healthy boundaries
✨ 20 conversation starters that bring families closer
✨ Proven frameworks for productive business meetings
✨ Engaging activities for multi-generational connection
✨ Year-end reflection questions that deepen understanding

Download Now