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.”

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 and The Leader Within. 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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Challenging, often subtle family dynamics, sensitive communications and interlinked governance structures all contribute to the complexity of family offices. Guided by renowned faculty, you will learn to navigate complex family office dynamics to more fully align stakeholders. You will develop skills to plan strategy, promote trust and communication, and address challenging issues around governance and continuity.

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