Honest and challenging conversations – the heart of the family business

Honest and challenging conversations – the heart of the family business

Challenging conversations. Approaching a difficult situation within a family business can be challenging. Underlying tensions, which often lead to less than honest conversations, are often caused by childhood rivalries. Sibling rivalries, generational differences or power struggles can be simmering beneath the surface just waiting to emerge when a small issue arises. But there are ways to handle these challenges.


We all know that well-worn cliché, ‘honesty is the best policy’. We also know that it’s far easier said than done.

How can family members when working together in business, have open and honest conversations with one another?

It all depends on the hat that each wear!

Approaching a difficult situation within a family business can be challenging. For instance, if the younger brother is the MD and needs to discuss the sales performance of his older sibling, rivalry from their childhood must be set aside to allow the conversation to focus solely on the business, and this becomes quite a challenging conversation.

Underlying tensions, which often lead to less than honest conversations, are often caused by such childhood rivalries. Sibling rivalries, generational differences or power struggles can be simmering beneath the surface just waiting to emerge when a small issue arises:

“You were always allowed to do …”

“I never had the chance to …”

“Why won’t you let me …”

In a non-family business, staff are employed to do a job and are expected to perform their role accordingly. Honesty is certainly an important factor, and team professionalism lends itself to being able to tackle difficult situations in an objective manner.

However, within a family business when presented with a challenging conversation, family members sometimes drop their professional approach and revert to the free-for-all, squabbling arguments of their youth. Heightened emotions can lead to harsh words being said. Which of course, doesn’t solve the problem.

So, how do families have those necessary, but challenging ‘honest conversations’?

Take the case of Anthony who employed his son Steve. Steve made a major blunder with a customer that cost the business a lot of money. When Anthony has to talk to Steve about his blunder, does he do so as:

  • Father to son? (if this is the case, Steve maybe thinking “Is Dad going to discipline me the same way he did when I was 14 and ran the car into the garage door?”)
  • Shareholder to shareholder? (Steve is probably a shareholder – or will be – and so has a stake in the business)
  • Manager to employee? (Steve is a paid employee – does this make a difference?)

If Anthony puts his ‘father’s hat’ on, the emotional tensions will likely be high as each remembers (sometimes unconsciously) all the traumatic conversations or experiences of the past. If he puts his ‘shareholder’s hat’ on, it will most likely be about the bottom line and not about improving Steve’s performance. It’s the ‘manager’s hat’ Anthony needs to wear. And so the conversation may go …

“Steve, I’m talking to you now as manager to employee. These are the same things I say to any of my other employees. Tonight you can come around and have a beer and tell me about the tough boss you have, but right now, I’m talking to you as your manager. I’m that tough boss!”.

Both Anthony and Steve are clear on which hat each is wearing. And whilst it’s a very serious and challenging conversation about Steve’s poor performance, he’s aware that his father, Anthony, still loves him and has invited him home that evening to talk about his ‘Tough boss’.

So, for those challenging conversations, honesty can be enhanced by wearing the appropriate hat.

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