Mark Freeman is a CPA and investment advisor for the Clayton Family Office (a single-family office supporting four generations of the Jim Clayton family) and president of the family’s private trust company. He talks about the challenging work the family has done to improve their communication and move forward together:
How is the Clayton Family Office set up, and who does it serve?
It’s a single-family office that is transitioning from being primarily a G1 support office to a fully engaged, four-generation support office. Jim Clayton, our 91-year-old patriarch, is living alongside G2, G3 and 10 young G4 members. Including the married-ins, there are 37 family members.
Our family office team of 10 wear a variety of hats. Several of us also worked within a bank the family owned, where for years the trust department served as a quasi-family office. After Jim sold the bank, I stayed initially with the trust department and then re-joined the family office full-time in 2022.
We provide standard family office services: managing the enterprise, engaging family and building out the legacy framework. Much of the legacy planning is still evolving, and we have done a lot of work over the last year and a half to move that forward.
You have described the family as moving from conflict to communication. How did that happen?
We were admittedly stuck in past disagreements and strained relationships within G1 and G2. This was hindering our ability to move forward with any meaningful legacy planning for the family — and the family had grown to four generations.
So initially, we dug into learning. We read everything we could get our hands on: all the historical and modern thought leadership on family wealth planning and conflict management. We attended several conferences and forums and joined family office peer groups. We started studying and engaging with families that were far more mature in their evolution.
One of the things we learned is that our situation was not uncommon — and the family and the family office team developed some self-awareness that we needed unbiased third-party help to move forward.
What kind of third-party help did you find useful?
We had to get good coaching in the emotional intelligence area to learn communication skills that would foster a culture of healthy conflict and to unlearn some of the behaviors and subconscious tendencies that were hindering connections. We needed coaching to focus on relationship building, first and foremost, before advancing to the more technical transition and legacy planning.
We formed a loose steering committee to interview consultants and coaching candidates, and once a best-fit consulting team was identified, the family committed to support the recommended training and coaching.
In 2024, four two-day weekend training sessions with a representative group of family members were held — and were transformative. The first two focused purely on communication skills and trust. Then, in session three, the family originated a shared purpose, core values and a vision map. In the fourth session, the family began exploring a proposed governance framework and co-designed an initial draft family constitution.
That work has allowed the family to move forward with the legacy initiatives and a governance rollout that would not have been achieved without engaging other families and coaches and development of internal leaders.
What else helped the family move forward?
We recognized that communication is a skill — you can practice it. It was helpful to practice conversations with a moderator in the room. With this practice, we were able to advance from light topics to more sensitive matters, and to help some individuals move beyond past issues.
We learned that active listening is an important part of communication — and that many times, just being sure that the timing and atmosphere is right can be critical to holding a healthy conversation.
How have you been working to engage the next generation?
We have developed a number of engagement tools. A family bank to support the entrepreneurial aspirations of the rising gen was early on the wish list. Financing was provided to two G3 siblings for successful early-stage business ventures, and with experience gained via a shared investment portfolio, another G3 member enhanced his wealth advisory and consulting practice, now offering option trading and estate planning services.
The family, early on, funded 529 plans for the 10 G4s. A comprehensive report is provided quarterly, with the whole family watching these college savings accounts grow. Philanthropy also is an area where broad interest exists across the family, and new programs to engage the rising gens are planned.
In addition, the G3 members are instrumental in keeping the family connected and fostering relationships and alignment. For several years, Jim and [his wife] Michell held an annual grandkids retreat. These retreats created strong connectivity and engagement across the G3 group and their families, which helped to improve relationships throughout all generations.
Has the family agreed on a purpose for the family office?
We have done some good work in this area. In the 2024 moderated sessions, session three was dedicated to the family co-designing a shared purpose, values and vision for the family. A graphic vision map was created that reflects this shared work. The process was a uniting experience for all.
As we move into 2025, we are set to hold the first annual family retreat and assembly meeting in September. As part of that meeting, we will have the assembly formally adopt each of these items. We will also be taking the draft family constitution to final form.
How has improving family communication helped with governance?
We co-designed a proposed governance framework that would include a family assembly and a family council. It’s intertwined with the family’s private trust company and family office. The PTC was activated January 2025, so it’s still relatively new. Additionally, various committees will increase engagement and capitalize on the diverse skill set of the family.
All of this is the result of the challenging work that a core group of family members did in 2024 that really allowed the family to become better aligned and advance to these more technical matters.
On another note, through this improved communication environment, the family was able to come together at the end of 2024 to modify an old 1983 family trust which had not aged well and had been a source of stress for years. Full family approval was required to approve the modifications, which better align the trust provisions with the family’s new multigenerational enterprise mindset.
The fact that the family was able to work through the modifications, and to unanimously approve them, is, I think, a testament to the work and the learning that was done in the communication area. The old trust had been a thorn in everyone’s side for so long, and it was a huge accomplishment for the family to move forward with the modification.
Finally, there is the momentum and the positivity that we carried out of 2024 into 2025. The 2024 work was done with a smaller representative group. The first annual retreat and the assembly meeting that we’re holding in September will include all the adult family members and spouses. We’re aiming for 100% attendance and participation. That’s another big achievement: willingness for the family to come together and embrace a more multigenerational mindset. The family has really bought into that.