Succeeding in Turbulent Times: A case study on leadership and teambuilding in single-family offices.

Date: Dec 17 2020

Jill Barber and Greg McCann

Note: This case study is based on Jill Barber’s work as President of CYMI Holdings. The “I” statements refer to her.

As a long-term professional in the family office, I was selected as the president of CYMI Holdings in the fall of 2018. My vision was that I wanted to create a more collaborative organization where we pushed decision-making down into the organization to empower all staff and create buy-in to our strategy at all levels.

What drove me was a deep awareness of the challenges of leading a family office in these turbulent times—and a recognition that being successful at this work now requires greater capacity and agility than ever.

Today’s global pandemic has made client families reflect anew on what truly matters and how they define value. Direct investing, strategic philanthropy, and holistic assessments of family wealth/capital are making the role of the family office and leaders evermore challenging. And, 36 percent of single-family offices are planning for leadership succession within the next four years; and an added 24 percent within the next seven to 10 years, according to the FOX 2019 Family Office Study. That is a total of 60 percent within the decade.

The upshot is clear: More than ever, key people in family offices must not only be subject matter experts, but also leaders who are part of an effective team.

To cultivate this in my family office, I focused first on my leadership development and then on team-building with a special focus on the importance of cultivating capacity and agility skills to create a culture shift. Creating time to reflect allowed for deeper awareness, more effective action, and a renewed enjoyment of my work.

Most remarkably, the progress we have made on our strategic plan as a part of this process increased substantially. What follows is a brief discussion of what we did.


Leadership Development

“Leadership is not a position or a title, it is action and example.”


-Donald H. McGannon

I first went to work with a professional coach who specializes in leadership development to create clarity on my leadership style and what I was asking of my leadership team and the staff.

What I quickly discovered was leadership had to start with me being more aware of myself. I was part of every interaction; and if I was going to ask the FO staff to grow, I had to lead by example.

So, when I had to call out a team member in front of their peers for not being accountable, I did it even though it was hard for me because part of leadership is learning to get comfortable with being uncomfortable.


Capacity and Agility

“The level of consciousness of an organization [culture] cannot exceed the level of consciousness [character and capacity] of its leader[s].”


-Frederic Laloux


My awareness deepened as I saw that, in addition to addressing daily problems and strategy, I needed to create a more effective team of leaders, not just subject matter experts. We needed to develop our capacity and agility.

Allow us to explain what I mean by these terms:

  • Capacity is the ability to evolve your mindset, emotional intelligence (self-awareness and empathy), effectiveness in framing complex issues, and ability to step back from a system to see it more clearly. That system can be your ego, client family or their enterprise(s), culture, or industry.
  • Agility is having the mindfulness to decide which style or ‘gear’ best suits the circumstances and goals. Most of us, for example, start off crawling in life, then walk, run, ride a bike, and drive a car. A few of us become pilots. A pilot then may have the capacity to fly to another country but use her agility to decide that taking a bike to the corner store makes the most sense. The same is true with leadership: We have to call on different skills at different times.



“We are not a team because we work together.

We are a team because we respect, trust, and care for each other.”

-Vala Afshar

At first, I thought this work was all about me but ultimately realized I was going to need to lead was a cultural shift. It was all about creating an agile organization that allowed everyone to succeed.

So, I set out to develop our leadership team into a more effective team, evolve the culture of the family office, and better serve the family. Within the framework of leadership development, we began to work on team-building.

The table that follows is the roadmap I had used in my coaching and used with my team at this stage. It outlines an approach to mindset, teamwork, difficult conversations, organizational change, and other key factors at three levels of leadership: expert, achiever, and catalyst. (We felt we were in the Achiever stage but aspired to the Catalyst one.)



One important shift for me that this led to was putting less emphasis on doing or executing and more emphasis on leading. That meant creating the vision, empowering others, and developing the capacity and agility of the staff. I now, for example, delegate the framing and facilitating of more meetings than I ever have.

This shift created space for me to focus on the work I was most interested in pursuing and provided new challenges that were exciting to tackle. As importantly, it also provided new opportunities, challenges, and renewed excitement for others on my team. And, in turn, it allowed us to do some transformational work on how we worked together.

Using the Table Group’s Five Behaviors of a Cohesive Team framework, we focused on developing:

  1. Vulnerability-based trust - We recognized that we had to connect on the real issues that challenged us, let our guard down, and believe that other team members had our best interest at heart. This was foundational.
  2. Healthy, rigorous, respectful conflict - We historically tended to avoid conflict, but focusing on healthy, rigorous, respectful conflict. This helped us reframe conversations from potentially personal and hurtful to more idea-based and helpful.
  3. Commitment - We reframed how we made decisions from either unilateral or consensus-based to a focus on a fair process in which all relevant people felt they had truly been heard so they could then commit.
  4. Accountability to the team.This focus helped me recognize that the more a leader is willing to call out team members on their commitments, the less they will have to because the team will.
  5. Team results over individual agendas - This helps us lessen the impact of personal agendas that are misaligned with team or organizational goals and focus on rowing in the same direction—hoping, of course, for opportunities for individual goals to align with those team or

These models, and the shared language they provide, have become a beneficial and vital process of the work we do. After all, without a team that can work effectively together, have the difficult conversations, and truly lead, the ability to optimize the value to my client family is limited. Once we understood the five behaviors and committed to working on these areas, the real discussions, innovation, work and fun started to happen.

(To learn more about these leadership and team-building models, view this FOX blog.)


Jill Barber is President of CYMI Holdings, which provides wealth advisory services to the Mathile Family. As a member of CYMI since 1999, Jill has been involved in hundreds of successful business and philanthropic transactions that have helped the Mathile Family to change the landscape of the Dayton region and several places around the world.

Greg McCann is the founder of the consulting firm McCann & Associates and founder and director (1998-2006, 2009-2014) of Stetson University's Family Enterprise Center. He coaches with, speaks on, writes about, consults with and teaches on the family enterprise. For more on Greg’s firm, visit