Thought Leadership

Difficult Conversations in Family Business: When Should You Have Them, and Why?

Few people enjoy confrontation in their personal or professional lives. Family business is a mix of the two worlds, so the prospect is even more daunting, according to Brooke Vuckovic, Academic Director of Kellogg Executive Education's Leading for Impact within Family Enterprise. “Family systems in particular are always more fraught because the relationships are closer and longer-term,” she said. “There are more hot buttons to push, and people are often locked into memories that may not be relevant. If you haven’t built up the skill to address difficult topics over time, the default will be to avoid them and hope the issue goes away, as opposed to seeing conflict as a way to develop yourself and make the relationship stronger.”

Because people tend to overestimate the potential downside of having a tough conversation while underestimating the upside over both the short and long term, it’s useful to reflect on the situation and write down both the risks of talking it out and the risks of avoiding it, Vuckovic noted. “If you want to delay it, the one legitimate reason for doing so is when emotions are heated and you don’t want to suddenly raise a topic,” she said. “Or perhaps there’s a heated deadline or other time pressure. Maybe you need to gather more data. But you need to be clear about those reasons.”

If your inclination is to make peace with the issue and skip the conversation, there are ways to determine whether or not you’re taking the easy way out. Chief among them is to talk to a confidant. “It could be a disinterested friend, a coach, a mentor, or a family member whose wisdom you trust,” Vuckovic said. “Also, if you have a high level of awareness, ask yourself if you’re really okay with not talking about it, or if it is popping out in odd ways in other areas of your life. For example, are you making peace at work and then taking it out on your family at home?”

After resolving whether or not you’re going to broach the subject, you need to understand why it’s important to do so. “What’s the big pull here?” said Vuckovic. “Call yourself to a larger purpose. Is it about greater transparency within the company? Excellence in operations? Learning how to function well so that the business enhances the family and vice versa? What, on a larger scale, makes addressing this difficult issue compelling to you?”

Assuming you want to move ahead, the next step is to decide on the single most important objective for having the conversation, Vuckovic said. “Make it something you can control,” she stressed. “You can’t control whether or not the person you’re talking to will want to engage or will suddenly accept what you’re proposing. But you can control a concrete goal of describing the situation from your perspective. Or it might be approaching the people you need to talk to at the next board meeting to see if they’re interested in a given topic. Frame the next conversation and the purpose of the next single action. Make sure your goals are finite and that your expectations aren’t too high. If thinking about turning the relationship around is too big, then think only about the single next step.”

Once you’ve decided on the objective of the conversation, you’ll need to consider the set-up. Vuckovic stressed the importance of “conversational safety,” which helps ensure that both sides are open to learning. “Trying to do it at the end of a long board meeting, when everyone’s patience is thin, is not a good idea,” she said. “You don’t want to talk about a family issue in the middle of a team meeting. You don’t want to raise organizational restructuring at the dinner table. You’ll also need to think about what both sides need to know in advance to be productive You want to assess the location and timing of the conversation. At the dinner table? In a meeting room? There’s no cookie-cutter set-up here. It’ll be different in every family, organization and the issue at hand.”

Overall, the important thing is to appreciate the value of learning to have these conversations and the way developing a facility with them benefits you personally and professionally, Vuckovic said. “It really doesn’t matter where you practice having difficult conversations because the skills transfer. If you learn them at work, they transfer to home. If you develop them at home, they transfer to work.”

Next: how to have the conversation


Dr. Brooke Vuckovic teaches leadership coaching to Kellogg's full-time MBA students and has co-developed coaching programs for multiple Executive Education programs. In addition to being the Academic Director for Leading for Impact within Family Enterprise, The Leader Within and the Enterprise Leadership Program. Dr. Vuckovic teaches in many of the leadership programs offered through Kellogg Executive Education and the Center for Nonprofit Management. Outside of Kellogg, Dr. Vuckovic has an executive coaching practice working with senior executives.

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Family Enterprise Boards

Family businesses are uniquely complex enterprises. This program empowers current and future directors of family-owned businesses to navigate the challenges posed by those organizations while learning to design, engage and lead boards that leverage their companies’ strategic advantages.

Family Enterprise Boards: Upcoming Sessions

September 20-24, 2020

Start: September 20 at 2:30 PM

End: September 24 at 1:15 PM

Evanston campus

This Approval Program is limited to individuals with specific business experience. All applications will be subject to review and approval from the program’s Academic Director.

$11,550

Fee includes lodging and most meals


Forming Family Enterprise Governance

One of the most critical times in a family enterprise’s evolution is moving from the processes, people and structures that proved successful for a controlling owner to those that support a sibling partnership. Engage with faculty from Kellogg’s Center for Family Enterprises for leadership insights on governance architecture and effective decision making to support a vision that will guide multigenerational continuity.

Forming Family Enterprise Governance: Upcoming Sessions

February 16-18, 2021

Start: February 16 at 8:00 AM

End: February 18 at 3:30 PM

Miami campus

This Approval Program is limited to individuals with specific business experience. All applications will be subject to review and approval from the program’s Academic Director.

$6,750

Program Fee does not include accommodations.


Governing Family Enterprises

Join peers from leading family-run organizations to learn how family governance can help sustain business continuity, family unity and commitment. Come away equipped and energized to realize your vision for the future of your family enterprise with confidence.

Governing Family Enterprises: Upcoming Sessions

October 4-8, 2020

Start: October 4 at 1:00 PM

End: October 8 at 12:30 PM

Evanston campus

This Approval Program is limited to individuals with specific business experience. All applications will be subject to review and approval from the program’s Academic Director.

$11,550

Fee includes lodging and most meals


Leading for Impact within Family Enterprise

As an aspiring leader within family enterprise, you’ll discover how to establish your credibility and authority in the business community, among family shareholders, with the board and management team. As an established leader, you’ll explore the complexities of mentoring the next generation and of managing succession and letting-go. For all, the program can enable you to better manage the nuanced paradoxes that are characteristic of family business leadership.

Leading for Impact within Family Enterprise: Upcoming Sessions

May 2-6, 2021

Start: May 2 at 1:00 PM

End: May 6 at 1:00 PM

Evanston campus

This Approval Program is limited to individuals with specific business experience. All applications will be subject to review and approval from the program’s Academic Director.

$11,750

Fee includes lodging and most meals

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