Why Is It So Hard to Talk to Family? Cross-generation Family Meeting Tips

Have you ever had a difficult time talking about sensitive subjects with your parents or your children?

I am an experienced meeting facilitator. In my role as an information systems project manager I have led many successful meetings with all kinds of crowds. I’ve been trained in communicating with difficult people, negotiation, crucial and confrontational conversations, influential leadership, brainstorming, conducting successful meetings and many other relevant topics.

Because of that, I thought leading our very first 3 generation family meeting several years ago would be a snap.


We held our first meeting in our first born son’s house around the holidays. Our other son also drove into the city to attend – with his finance and her second born child. We waited until the preschool age grandchild was soundly asleep and kept our fingers crossed that our newborn granddaughter would fall back asleep after the next feeding.

Prior to this time, we had not had formal family discussions about extended family items and we hadn’t really had in depth discussions with our daughter-in-law or our future daughter-in-law.

Why have a cross-generation family meeting?

Our goal was to initiate annual family meetings to discuss things like family values, resources, goals, hopes, dreams and yes finances and estate plans. We wanted to open a forum for us to share our thoughts and resources with our descendents and more importantly, to let them share their thoughts and views with us and each other.

We did a lot of things that worked out for us, and some that didn’t work as well as we had hoped.

What worked:

  • We defined ‘our family’ as myself, my spouse, our two grown children, their significant others and their children. This worked because it is a small group and the kids didn’t really participate in the first meeting.
  • We preset the agenda so everyone know what we would be talking about. We had a formal printed agenda for each person participating, with spots for them to take notes.
  • We set time limits for each agenda item.
  • We all tried hard to be open and responsive to each other.
  • We agreed to rotate leadership of the meeting in future years.
  • We spiced it up with a little wine.

What didn’t work: 

Three main things were noted that we could have improved on. These were:

  • We went way over the allotted time-frames (our meeting lasted 4 and a half hours instead of two hours).
  • We slide back into generational or personal roles when it would have been better not to do so. For instance, the older generation (my spouse and I) caught ourselves trying to lecture and/or control. There may have been some ‘lets just do this cause Mom wants to ‘ from the younger generations.
  • We had difficulty talking about our attitudes towards money. Two of our agenda items related to exploration of how we were each raised, how our current relationships (marriage, engagement, etc) dealt with money and telling stories about the same. It felt awkward to hear our children talk about how they were taught money attitudes (hey we did the raising!) and I’m sure they felt awkward telling it.

What should we have done differently?

  • The first part of the meeting was mainly administrative. We covered things like what is a family meeting, what do people do in them, why should we have one, what rules will we use to conduct the meeting and etc. This should have been it’s own meeting for us.
  • We should not have tried to talk about money at our very first meeting! Talking about money is one of the last conversational taboos. In retrospect, it would have been better to more thoroughly explore what our family would want to discuss in future family meetings.
  • We definitely should not have kept meeting for so many hours!

We have continued our new annual family meeting. This year will be our fourth and it is my turn to lead again.

Since this first meeting, we have held one each year and I have done quite a bit of research on the subject and have developed what I hope is a helpful checklist for others to use. Check  out my family meeting checklist at and let me hear your comments here on it.

What suggestions do you have for me? Do you hold family meetings? What tips can you share?

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