The imagined conversation

By Nancy Drozdow

What keeps us from discussing difficult issues? Often, it's our fear of what will be said. Here's how to move from paralysis to a productive dialogue.

If you have spent quality time with business families, you likely have heard comments like the following:

• “I think raising this issue would be more damaging than helpful.”

• “I’ve tried to talk about it with my sister, but she’ll never do anything differently, so what’s the point?”

• “Every time I talk to my cousin, we start fighting our parents’ old battle, so now we just avoid it.”

We call these “imagined conversations”—internal rehearsals, played out in our heads in such horrid detail that we talk ourselves out of actually having them, even when we know the costs of avoidance are high. The issues we’re afraid to discuss are often essential for a family business—succession plans and career interests, feedback on performance, money and inheritance, etc.

Why are these discussions so difficult to have? And how can you move from paralysis to productive conversations that advance both the business and the relationship?

It’s not just business; it’s personal

In a family enterprise, difficult conversations can quickly become personal. What starts out as a business discussion becomes entwined—even if unconsciously—with a long history of family dynamics, past injuries and patterns of protection.

A discussion about succession becomes a test of self-worth between a parent and a child. A conversation about family employment becomes a competition for standing between branches of the family. Many avoid raising these issues, since the only imagined outcome is something worse than already exists. Yet we know that avoiding these conversations can do just as much harm as arguing can—or even more.

Three layers

Conversations in business families often have three interconnected layers. Understanding these layers can help family members to get “unstuck.”

• The interpersonal. “What is my relationship to the other person? How does this issue or conversation affect my own aspirations and interests, and my relationship not just with this person but in the constellation of relationships that surround each of us?” This is the place we most easily go, and we often get stuck here. “What’s wrong with him/her? What’s wrong with me?”

• The role. “What job do I have, relative to the other person’s job, and how does that help or inhibit the conversation we need to have? How do the tasks involved in my or the other person’s role relate to this issue, regardless of what person is in that role? Where does each fit in the organizational hierarchy?”

• The enterprise. “What is the bigger picture? How does this issue relate to our goals at the enterprise level? What we are trying to do as both a family and a business, now and over the longer term?”

Seeing the larger picture

Consider the following example: A manufacturing company in a high-growth industry is not meeting its budget goals. The eldest brother of five siblings is CEO. A sister is head of sales. Other family members head manufacturing, purchasing and distribution. The CEO and the head of sales have begun to argue every time they see each other. The CEO thinks his sister is slacking off. He remembers that she was a little “wild” when they were in high school, though she also helped grow the business. Others withdraw, knowing that once again, it will come to the same old argument between the two siblings.

This brother and sister begin with the belief that if only the other were different, life would be better. Their three siblings have their own interpersonal and role issues too, so they find it hard to “help.”

At this point, the siblings are stuck at the interpersonal level. Neither has considered the industry dynamics, including who’s growing and who’s shrinking. New entrants are showing up, and they are much larger companies with more sophisticated manufacturing and lower costs. Looking at the enterprise as a whole could change the focus of their conversation from an interpersonal conflict to a shared problem that people in both roles (CEO and head of sales) must assess and address.

Getting unstuck: 5 steps

Imagining a conversation often takes people down the same unhappy path already walked. Here are some steps you can take to make the actual discussion more productive than the one you are imagining.

1. Set a bigger goal. Can you change the typical pattern by aiming to solve a bigger problem than the one you imagine and, in doing so, create a precedent for discussing important issues? For example, you might approach the topic in terms of a goal everyone can get behind, like growing profitability, acquiring a new customer segment or developing talent throughout the business.

2. Create deliberate mechanisms for pausing when the conversation goes off track. Agree on a course of action when the parties are stuck in an unproductive cycle or avoiding a conversation. For example, you might take 24 hours to calm down before attempting to discuss the issue. Other family members who are in the presence of a difficult pair or trio might suggest a timeout rather than hanging back or taking sides. Make a rule that you will “press the pause button” when you find yourself falling into old patterns, and that you will restate things when they have been misheard or your choice of words was poor.

3. Have the imagined conversation. Standing together, each party separately plays out the conversation he or she has been imagining, with no interruption (verbal or otherwise) from the other.

By sharing your imagined conversations rather than debating or trying to do it differently right away, you might actually work together to identify the reasons you get stuck. Diagnose what happens. Why do you think it’s so difficult to discuss the issue in a productive way? Don’t forget about how it actually feels—palms sweaty, mind struggling to get the words out, eyes down, etc. With the new information, see if you can deliberately experiment with new ways to say things, frame things, etc. This can feel hokey at first, but eventually it can become second nature.

4. Reflect on what happened. After discussing an uncomfortable issue, ask the other party’s opinion about how the conversation went. What was he or she feeling? Consider what you might have done differently. Agree on things you can try next time.

5. Let others know you’re working on it. This signals to other family members that having this conversation is important enough to work on. It helps them to support you rather than avoid you. It also teaches them that if they are in a similar situation, they will be expected to work things through, and it creates a climate of openness that is usually preferred to one of gossip and politics.

Why you should try it

Ultimately, the only way to test whether the person you are avoiding will react the way you imagine is by taking a leap and actually trying to discuss the dreaded topic. It is a little like the elephant in the room anyway; you probably both know what the other is imagining. Leadership means taking a risk, so find a manageable risk to take and give it a try. The results can help you to learn about yourself and your family in ways that strengthen your longer-term relationship skills.

Nancy Drozdow is a principal at CFAR, a management consulting firm specializing in strategy and organizational development, with offices in Philadelphia and Cambridge, Mass. (

Article categories: 
Print / Download
Summer 2011


  • Low Interest Rates — Recession or Distortion?

    Financial markets have been volatile for the better part of the last two years. In the meantime, the current U.S. economic expansion has progressed to now become ...

  • September/October 2019 Family Matters


  • July/August 2019 Family Matters

    Kyle Fernley has been named the fifth president of Fernley & Fernley, a 133-year-old association man­agement company based in Philadelphia.

    Fernley has also been named p...

  • Building a community

    When Family Business Magazine debuted in 1989, business leaders who had grown their companies after returning from World War II service were passing the baton to their baby boomer children...