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Ten Take-Aways from a Leadership Retreat for Executive Directors

ISSUE 21 • November 2023

People smiling in a sunny outdoor picture in Rockport, Maine
Dr. Thomas Wolf, Stanford Thompson, Dennie Palmer Wolf and Emily Masters with the 2022 retreat cohort in front of Rockport (Maine) Harbor.
Image: Luke Fatora

By Thomas Wolf

This post is part of a series examining more leadership training in the arts.

Many years ago, I interviewed Sanford Weill as part of a project on arts administration leadership that I was conducting for the Pew Charitable Trusts. At the time, Weill was both the Chairman of Citigroup and Chair of the Board of Trustees of Carnegie Hall. He was lamenting the fact that hiring a CEO for an arts organization is often a risky business.

“Arts organizations face great challenges in hiring staff leaders. Unlike large corporations like mine that are constantly training multiple internal candidates, any of whom can take over at a moment’s notice, budget constraints mean that arts groups do not have such a luxury. So, the big ones poach their leaders from peer organizations, hoping things will work out when these individuals come into a new organizational environment. And the smaller ones often recruit staff members who have never served as CEOs and are forced to learn leadership skills on the job. The uneven results speak for themselves.”

Things haven’t changed all that much since that interview. In particular, many leaders of small and medium-size arts organizations still come to their jobs without either formal or on-the-job training. Many face new challenges without a background of relevant experience. With this in mind, Dennie Palmer Wolf, Stanford Thompson, Emily Masters, and I decided to design an annual intensive, four-day leadership retreat for executive directors (most of whom are in their first executive director position) at the end of August in Maine each summer. What we have learned as we plan the fourth year of the retreat may be useful to others.

“I feel immensely blessed to have been a part of this process. The depth and the care with which everything was crafted, adapted, and continues to wrap around us has been invaluable. As I’ve come back home, I’ve spent a lot of time in the space of value and survival alongside stability and visioning. I’m careful to hold space for visioning and dreaming so that there is intentional room for creativity, innovation, and growth. The gentle yet deliberate facilitation helped me have the time that was necessary to unpack and sort through some critical points with allies and experts, allowing me to refocus in a noisy time.”

DeLashea Strawder, Executive and Artistic Director, Mosaic Youth Theatre of Detroit

1. Many first-time executive directors want to spend less time being lectured to and more time analyzing, together with peers, the challenges and opportunities they face.

To ensure quality discussion, we welcome all participants to submit a form describing the topic they wish to offer the group to deliberate. This is followed by an interview with us, the faculty. We then group the discussion topics in ways that allow similar issues to surface in parallel, thereby enriching the opportunities for insight. For example, many have wanted to discuss challenges in their relationships with their boards, especially their board chairs. In one of the retreats, we devoted half a day to this topic alone. 

2. Diversity in cultural background and geography is desirable. However, participants should be from somewhat similar types of organizations both in terms of discipline and size.

Participant cohorts each year have been a healthy mix of men and women as well as people of different ethnic backgrounds. However, for discussions to be meaningful, some similarity in organizational types and size is essential. Most participant organizations have had budgets ranging from one to five million dollars. While the range of organizations in one cohort included a performing arts facility, several performing organizations in music, dance and theatre, and a few music education organizations, it was decided not to include individuals from museums and literary organizations at this retreat.

Dennie Palmer Wolf conducting a planning discussion
Dennie Palmer Wolf facilitating a planning discussion.

3. For many executive directors of small and medium-sized organizations, a commitment of more than 5-6 days (including travel time) for a retreat is more than they feel they can afford.

Executive directors of small and medium-sized organizations, many of whom have young families and caregiving responsibilities in addition to managing, limits the number of days they can be away. On the other hand, they find one- and two-day workshops, inadequate to get the depth of experience they seek. The four-day format for the retreat itself has worked well.

4. To facilitate in-depth and honest discussion, a group must be small enough that everyone has ample opportunity to reflect on their own and other people’s challenges.

Groups have ranged between eight and ten executive directors along with the four-person faculty.

5. The retreat must be a safe space where people can be honest and trust that confidential information will remain confidential.

The small size of the group tends to contribute to a feeling of safety. Individuals commit to confidentiality. The group intentionally does not include more than one person per community since doing so might preclude frank discussion of local situations.

Lecolion Washington from the Community Music Center of Boston shares a lighter moment with Jon Hinojosa of SAY Sí in San Antonio while faculty member Dennie Wolf listens closely. (photo credit: Aisan Acosta).
Aisan Acosta Lecolion Washington from the Community Music Center of Boston shares a lighter moment with Jon Hinojosa of SAY Sí in San Antonio while faculty member Dennie Wolf listens closely.

6. Some traditional class-room type teaching on selected topics can be useful if it is chosen by the participants based around the challenges they face.

It became clear, as the first retreat was being designed, that participants wanted some time devoted to developing their knowledge base – especially in technical, governance, and financial matters they have to master to do their new jobs. Topics over the years have included: effecting a strong executive director/board partnership, planned giving and capital campaigns, evaluation and demonstrating impact, communication and messaging, EDI strategies, as well as recruiting and interviewing prospective staff. 

7. Background articles and books can be included for those who want and expect them but participants should not be required to read them in advance.

Different people have various learning styles. For some, access to the professional literature is an important aid to gaining knowledge. Others are less interested. A number of background readings relevant to the topics to be covered are sent to participants in advance. Some appear to have spent many hours studying them but it is not a requirement.

8. Unstructured informal time is essential. So are group activities that build a sense of community.

The opening event is a lobster dinner in a private home where participants get an opportunity to introduce themselves and learn about one another. An upcoming retreat will include a short boat trip. There is also time for one-on-one conversations with faculty members for those who want to explore new directions or dig into challenging issues.

Taneshia Nash Laird, DeLashea Mya Strawder, Myka Miller, Lecolion Washington, and Lorna Jane Norris, Stanford Thompson, Tom Wolf, and Dennie Wolf in a sunny outdoor picture

9. The setting and timing for an executive leadership retreat can itself be a draw, especially if there is ample opportunity to tack on a vacation.

Mid-coast Maine, where the retreats have taken place, is a beautiful part of the world. Late August often aligns with people’s vacation time so several participants have extended their visits to take in places like Acadia National Park nearby (along with their partners and families) before or after the retreat itself. 

10. A commitment to stay in touch has been enhanced by check-ins organized as part of the curriculum for the group to continue to share.

After the intensive time together, participants become close. Many welcome the annual check-in to learn how their lives and jobs are evolving and to continue the exchange of strategies. Or even to celebrate early wins.

For more about the upcoming retreat in August 2024, please find more information here.

“I’ve never encountered a professional development experience quite like it – the level of customization, relevance, and bias for action was wonderfully inspiring.”

– Ben Cadwallader, Executive Director, Los Angeles Chamber Orchestra

This is post is part of our On Our Minds newsletter. Previous issues of On Our Minds focused on equity in the arts. You can read them here:

Arts Outcomes Worthy of Pursuit – Joanna Borowski and Samuel McDonald of the New Jersey Symphony’s Education and Community Engagement Department share outcomes they considered worthy of research for their Training Ensemble. 

Access to Evaluation Services – Finally, our colleague and collaborator Allison Russo shares how close to 100 arts education organizations in Newark are working together to gain access to quality evaluation services.