- December 4, 2025
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When you read the title of this article, it’s likely that a specific instance of having a difficult conversation popped into your mind. Just about everyone, at some point in time, has had to have a difficult conversation with someone in their life. It’s part of the human experience — and can be one of the hardest parts. In business, it’s no different. Every leader faces the reality of difficult conversations, and just like in regular life, it’s not something that most leaders look forward to. In fact, they often put those conversations off — especially in family businesses, to the detriment of the family and the business.
In my work with family business owners and executives, I have found that one of the greatest challenges (and biggest blind spots) facing leaders is the art of having difficult conversations. While some leaders are comfortable facing conflict head on, most of us avoid them, because we are not prepared to deal with the potential discomfort of the conversation — and the outcome. Nobody likes the strife that comes with a difficult conversation. But as a leader, you simply don’t have the luxury of putting them off. It’s part of the job. And when it’s your family, it can be even harder.
CPP, Inc., an industry leader in research, training, and organizational development tools, conducted a worldwide study looking at workplace conflict and found, on average, U.S. workers spend approximately 2.8 hours per week dealing with conflict — translating into over $350 billion in paid hours annually. Additionally, 10% of workers report that project failures are the direct result of workplace conflict. The number of hours spent on conflict in this report won't be a surprise to most people in business, and there’s no clear remedy.