Awkward! Family Meeting Retreats.

“I want you to arrange a meeting with the heads of the five families”

The Godfather

We pulled up to the clandestine location for the secret, covert meeting. We made sure to cover our tracks and not let anyone know we were gathering. The subject matter was confidential and extremely sensitive. This was how our first family meeting retreat went down.

I’ll give our family credit for trying something new. We are great at finding ways to look at the big picture. But our first family retreat was a little uncomfortable and a lot awkward. Uncomfortable can be good, because it means you’re changing and growing. Awkward is, well, just plain awkward.

Working “In” the Business vs Working “On” the Business

When your business is growing rapidly, you’re totally immersed in the day-to-day running of the business. Rarely do you have the ability to step aside and look at the big picture. You’ve heard it called working ‘in” the business vs working “on” the business.

Most family businesses are motivated to begin strategic planning because of a crisis or difficult situation. In our case, our business was facing increased competition and we needed to grow the business more rapidly to remain competitive.

  • We needed to formalize our planning and prepare a strategic plan.
  • We had to extract our plans from our heads and put it down on paper
  • For the first time we were formally discussing the direction of the business
  • We needed to get the family on the same page.
  • We were inviting more non-family members into decision making positions and committees and needed a plan that could be shared with them.

Up until this point we were riding a wave of success and the sales drove the business direction. We needed to flip this around and determine where we were most successful and effective and create a more deliberate path.

Some random thoughts about family meeting retreats:

1. Going Offsite

  • Finding the time to do this during the workday was next to impossible. We tried.
  • Finally, we decided to take a day and go to an outside location for our first family meeting. We decided getting away from the office and a weekend stay at a nearby hotel would be a good start.
  • The off-site meetings seemed a little forced. We eventually moved the meetings on-site to our conference room.
  • You’re always told you should have off-site meetings, but actually we felt more comfortable being on-site.
  • Being comfortable is key and much more productive.

2. Where Do You Start?

  • Our family met in a conference room at the hotel
  • Getting started is the hardest. Sitting around the conference table with just family is different. Usually other employees would be meeting with us.
  • We setup flip charts and pinned pages to every available wall space and just wrote all of our discussions down.
  • It was a free-wheeling brainstorming session. It was also a brain dump of all the ideas and plans in our head onto paper.
  • Later we organized the ideas by topics.
  • We started with a discussion about our personal goals then business strategy later.
  • In hindsight, I think it would be more comfortable to start with a business topic rather than a personal topic. It’s a better ice-breaker.

3. Discussion – Personal Goals

  • Discussing personal goals is especially difficult. For many of us, it’s the first time we’ve even thought about it.
  • As people open up more, it becomes easier to share. You really need to go around the room several times to be comfortable sharing.
  • There is a tendency to keep wandering back into the comfort zone of discussing the business side.
  • Strangely, it almost seems more uncomfortable sharing our personal goals with family you know well, rather than with peers or others outside of the business.
  • As a family we often go out for dinner together, have family get-togethers for holidays and birthdays, and spend vacations together, but this was different. Even though we work closely together every day, all of our discussions are about the business. Rarely, if ever do we bring up personal issues during work. Funny, we never hesitate bringing up business issues during family get-togethers.
  • This is a good opportunity to determine which family members are genuinely interested in staying in the business.
  • In our case we had all worked in the business for ten years or more and genuinely wanted to be in the business. If you’ve invited newly hired family members to the meeting, the discussions might be more sensitive.
  • The personal discussions were interesting but didn’t really change anything in the business. This doesn’t mean it should be skipped. At a minimum you gain a newfound understanding of the other family members in the business which helps you to work with them more effectively.

4. Discussion – Business Goals

After our personal goal-setting session, we moved onto the business strategy topics. As you look further out to future years, be prepared to discuss sensitive issues:

  1. Blue-sky future direction of the business
  2. Realistic future direction of the business
  3. Corporate culture-lifestyle or professionally managed business
  4. Choosing future leaders
  5. Hiring key non-family executives
  6. How fast to grow/How big do you want to be
  7. Funding growth strategy internally or externally
  8. Ownership and control
  • You may wonder what is meant by “blue-sky” direction of the business. This is looking at what markets or products the company should be offering in your wildest dreams. They often relate closely to your hobbies and interests. After you get that discussion out of your system, you quickly focus back on what is most realistic, which brings you back to the core business. It’s a great way to begin, because it’s fun to discuss your passion and puts you in a more forward-looking mindset.
  • When discussing job roles going forward, you’re sensitive to other family members already in those roles. You hold back a bit. For example two of us were in Marketing and we broadened the position responsibilities which made it possible to have both an analytical position and a creative/advertising position.
  • Develop the discipline of regularly looking at long term planning and the direction of your business. For us, scheduling an afternoon each month worked well. We didn’t get the meeting in every month, but it’s a good discipline having it regularly scheduled.
  • Prepare a strategic plan that is an ongoing working document not just a a “one-hit wonder” plan that sits on the shelf. We included things that need to be referred to frequently.

5. Outside Facilitators

  • An outside facilitator can help move the meeting along, although we didn’t use one.
  • If there is family conflict, a facilitator might be more valuable and necessary.
  • Select someone with great trust when discussing personal goals. I think it might cause the family to hold back their more personal discussions.
  • Maybe introduce a facilitator after the personal goals discussion at the start of the business discussion.


Our Family Meetings were heavily business focused rather than the traditional family oriented issues format. It was a more interesting reason for us to meet together and the business issues created a reason to meet on a more regular basis.

We discussed both family issues and business issues in these meetings.

We continued the meetings for about three years. We eventually created a board which included the responsibilities of strategic planning and replaced the planning portion of the meetings.

We still held family meetings to discuss family/business issues and top-level strategic direction. The frequency of the meetings became more adhoc but remained very effective. They are the single most effective method of improving communication within the family.