When the Problem Child in the Company is One of Your Own

18 May When the Problem Child in the Company is One of Your Own

They say that being a parent is the hardest job you’ll ever have. But in a family business, the challenge is being both a parent and a leader at the same time, especially when your adult child is struggling in the business. While this often shows up in a parent-child relationship, it’s not limited to that. It can just as easily involve a sibling, cousin, or other family member whose role isn’t working the way it needs to. They might be underperforming, misaligned, or just not well suited for their position. Others see it. People adjust around it. And while it’s easy to identify the struggling individual as the source of the problem, that’s rarely the whole story.

What looks like one person’s issue is almost always a function of the system around them – the relationships, roles, and patterns that everyone in the business has had a hand in shaping. Real and lasting change rarely comes from fixing the other person. It tends to emerge when everyone involved – leaders included – turns the focus toward their own growth and maturity.

This is one of the most common and difficult situations in a family enterprise. It’s at the intersection of family, ownership, and business, where priorities often compete. As a family member, you might prioritize relationships, loyalty, and unconditional acceptance. As a leader, you’re responsible for performance, accountability, and the health of the organization. What might be a straightforward issue in another company becomes more complicated and emotionally charged when there’s family in the business. This is often what people are pointing to when they talk about having a “problem child,” though the reality is usually more complex.

In this kind of situation, family business leaders often find themselves stuck. They delay having honest conversations. They avoid clarifying expectations. They make accommodations that they wouldn’t make for anyone else. This is understandable – these aren’t easy conversations, and the stakes feel especially high when family is involved. Most leaders are trying to do right by both the business and the relationship at the same time.

But here’s a reframe worth considering:  Instead of asking “what’s wrong with them?” try asking “what’s my part in this pattern?” In a family business, the parent-leader’s own anxiety about upsetting a son or daughter often shapes the dynamic as much as anything the adult child is doing. Noticing that pull – the urge to smooth things over, to soften the feedback, to protect the relationship from discomfort – is actually the beginning of changing it. Avoiding the issue doesn’t make it go away. Over time, the impact of these patterns becomes harder to ignore.

At its core, this is a leadership issue. Strong family businesses don’t avoid these situations; they address them directly and compassionately. Did this person choose to be in the business, or was it assumed? Are they in a role that actually fits their skills and interests? Are expectations clearly defined and consistently applied? Do they report to someone with the authority to evaluate their performance? Are they receiving clear feedback and the support they need to grow into the role?

One shift that can make all of this easier: Try relating to your family member as a colleague rather than as someone who needs to be shielded from hard truths. That doesn’t mean being cold or transactional – it means extending the same honest, respectful engagement you’d offer any valued team member. Ironically, it’s often a more loving posture than the protection mode. People tend to rise when they’re engaged as capable adults rather than managed as fragile ones.

Looking at it another way, situations like this are often a mix of role fit, unclear expectations, and long-standing family dynamics. The individual may be struggling, but the situation is almost always influenced by the system around them. This perspective doesn’t remove accountability. It helps leaders see the situation more clearly and respond more effectively.

When a family member isn’t working out, there are no quick or easy answers. It takes courage and consistency, and a willingness to address what’s actually happening. That may mean redefining roles, strengthening reporting relationships, or having conversations that have been avoided for too long. In some cases, it may mean acknowledging that the best place for a family member is not in the role they currently hold, or even in the business.

This is also where it gets genuinely interesting and where the real leadership development lives. The question isn’t just “how do I handle this person?” but “where can I grow here?” Are there conversations you’ve been avoiding because you’re worried about the other person’s reaction – their upset, their disappointment, their withdrawal? That worry is worth examining. Getting clearer on your own values and expectations, and learning to hold them calmly even when others push back, is often the most important work a family business leader can do.

Now leadership emerges more clearly. How it’s handled sets a standard that will impact the business and the family for years to come. The goal isn’t to fix the “problem child,” but to understand what the situation is revealing – about the system, about the roles, and about yourself – and address it directly.