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How to Prepare For and Have Tough Conversations in Your Family Business

Larry and I glanced at each other with puzzled looks of concern. Mike was rambling. He had just repeated the story for the second time and was very obviously struggling to keep up with the conversation. As we glanced around the room we could see that others were uncomfortable, too, except for his sister, Ann, who stared as if to say, “This is what I’ve been telling you! He’s losing it!”

Seeing someone you care about showing signs of age or mental illness is one of the hardest things we can face. As boxer Sugar Ray Robinson famously quipped, “I always said I’d quit when I started to slide, and then I woke up one day and saw I done slid!” Unfortunately, many of us don’t realize that we are “sliding” until it has become apparent to others. What’s worse, most people won’t say anything when the signs emerge. People don’t want to be offensive or hurt the feelings of those they care about. And, of course, it’s a hard thing to talk about, quantify or explain.

I’ve been the bearer of this information several times—to beloved family members and clients alike. It has never been easy, but I’ve learned some important lessons. First, it always works best to deal with emotional issues before emotion becomes the issue. Before a problem develops, consider the following:

  1. As part of a family charter, partnership agreement or cultural covenant, define the desired process for sharing performance feedback. Encourage each other to talk about how you would want to approach certain issues, such as a breakdown in physical or mental health, substance abuse, signs of memory loss or cognitive impairment, loss of interest in the business, and so forth. Just making it okay to discuss these issues and putting ideas down on paper can make the entire process more palatable.
  2. Work with your family business partners to identify their concerns about aging. Discuss your experiences with other people in your life who’ve gotten older. What did you notice about them? How did you deal with the situation as you or they observed their mental or physical decline? What worked and what didn’t? How would you like your experience to differ?  
  3. Develop an agreement among your co-leaders about how they would like to be approached if someone else notices a change in their behavior or abilities. How would they like to learn about this, and what would kind of support would they like? Discuss the range of options for getting tested and working with a specialist to diagnose the change.

Start a conversation that very few people have, but that most of us face at some point. Until we make it an acceptable subject to talk about—removing some of the secrecy and shame—then we cannot positively change the way we deal with this potential life-altering trajectory.

What if you notice problems beginning to surface in a family member? When I’m faced with this, I tend to consider:

  • First, get the lay of the land. See if there’s another trusted individual in the organization or in the family with whom you could engage in a sensitive conversation.
  • Gently ask how things are going and what changes, if any, they might have observed in the company’s leadership or management. Look for subtle cues that they have concerns or noticed a shift.
  • Soften the conversation by saying something like, “I work with quite a few leaders who are getting up in years. A concern that often surfaces as part of a transition discussion is what to do if people in key positions begin to show signs of memory or cognition issues.  Have you ever discussed that topic in this company?” This gentle question can lead to a larger conversation. We then discuss strategies and options for working with specialists, and I may even coach them about how to approach the conversation with the person in question.
  • If I can’t find another trusted person, then I assess whether I have a responsibility, right or role in bringing up the issue. I usually decide that if I don’t speak up, then likely no one will, at least not until it becomes detrimental to the business or the family. 
  • In some circumstances, I’ve been able to soften the message via humor: “Okay, Joe, I can see you suffer from the same problem I have of not remembering where I was yesterday or what I had for breakfast, let alone what I was supposed to do for this meeting! I know that I’ve had to start writing everything down so that I can continue to fool most of the people most of the time! I wonder what you’ve been doing differently as you get older. Got any tips?” I then use this as a launching pad for a more in-depth conversation.
  • If humor isn’t the answer and I need to take a more straight-forward approach, I begin slowly, speaking from experience. “Mike, you and I have been working together for a  while now and I’ve noticed something in your communication style that I’m curious about. Can I share my concerns with you? I’ve noticed that you repeated your ski trip story several times today and forgot a number of the tasks that we discussed yesterday. Do you have any sense of what might be behind this shift in your communication?”
  • If I get a confused or befuddled response, or the person seems surprised but not angry, I might press ahead and say, “I know that if I were acting differently than I usually do, I’d like someone to point it out. I respect you a lot and thought you might like to be aware of the change. I know that hearing this can be distressing.” Here, I am speaking from my perspective, validating the other person and, finally, demonstrating empathy.  It’s now up to him or her to decide what to do with the information.  
  • If the person reacts angrily, I know that this usually stems from fear or embarrassment.  I then have to use my best emotional intelligence skills. I might say, “Yes, I know, I would be so distressed to have someone point this out and, yes, you might be absolutely correct that I don’t have my facts straight. All I know is that I like and respect you very much, and I wanted you to know that I’m seeing a change that I think you might not like. I’m happy to drop it, but I also thought I owed it to you to be transparent and honest.” 

These are difficult conversations, and sometimes we might get it wrong or we might misunderstand. That’s okay. What is not okay is sweeping behavior under the carpet when it might have a disastrous impact on the family and the business. Ideally, try to discuss this with your family and/or business leaders before it becomes a problem. If it is already a problem, first work to develop trust and build a strong relationship, then gently open the door to the issue. Make sure you have done a little research regarding local service providers who may be able to help. Find a good gerontologist in your area and be ready to make a recommendation. Suggest that he or she speaks with someone who can help and then be there to offer support as needed. Empathy and understanding are important here. After all, I’ll certainly want plenty of kindness and understanding when I start putting my car keys in the refrigerator and my wallet in the toaster. 

Lisë Stewart is a Director in the Closely Held and Family Business Services Group within the Private Business Services Practice. Lisë has experience in organizational development, strategic planning and training, and human performance management.

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