Leadership Retreat

My client organization approached me following the executive director’s leave, a subsequent strategic shift, and a re-organization that resulted in new reporting lines and a new set of priorities. The executive director and chief of staff decided to hold their first-ever leadership team retreat and, in a break with tradition, to hire an outside facilitator. The work together unfolded as follows:


LAUNCH: Starting the work strong sets us up to succeed. 

I began work just one month before the three-day leadership retreat. The project sponsors—the executive director and the chief of staff—shared their goals for the retreat in the context of recent organizational changes, team dynamics, and the year’s program priorities. I led the group through a participatory agenda-design process to align expectations, ensure full retreat participation from all team members, and build trust with me as the newcomer to this group.

DESIGN: Custom-tailoring your retreat for a better fit.

I conducted one-on-one interviews with the five leadership team members. Our conversations surfaced how team members understood their roles in both the leadership team and the organization, their expectations and ideas for the retreat, and what would enable them to do their best work in and beyond the retreat.

I synthesized the interview content into key themes, noting areas of alignment and misalignment. For misalignments, I encouraged the project sponsors to re-set expectations with the group about what would and would not happen at the retreat.

In the draft agenda, I designed a retreat trajectory and set of activities to be compatible with each person’s working style and the existing team norms/culture. My highly customized approach ensures that all team members can meet the team leaders’ expectations for their participation. The project sponsors socialized the agenda with the rest of the leadership team for feedback and input.

EXPERIENCE: Getting the biggest return on your investment of precious team time.

Retreat goals focused on (1) building trust for collaboration, (2) aligning behind the updated mission, (3) recognizing each team’s role and value in the new structure, and (4) uniting behind a shared vision and goals for the year ahead. 

To build trust and explore their new roles, the group engaged in an appreciations exercise, evaluated their strengths (as individuals and as a team), conducted a “fantasy campaign” simulation, and made commitments to each other and the work. To align on the new organizational direction and set goals for the year, the group precisely defined key concepts, power-mapped their operating environment, analyzed their target audiences, and developed a campaign roadmap.

One of my special strengths as a facilitator and coach is my ability to improvise optimal ways forward in real time. During my client’s retreat, I read the group, closely partnered with project sponsors, and called on a wide range of tools and past experiences to enable the group to do their best work at every step. In addition to in-the-moment pivots, we ended up developing a new third-day agenda, based on the group’s motivation and needs, to achieve the retreat goals.

TRANSITION: Ensuring the retreat work leads to long-term outcomes.

Too often, when teams leave the retreat space they also leave behind their learnings, ideas, and commitments. In my client’s retreat, participants left with tangible artifacts reinforcing the trust and recognition we targeted as well as a collaborative project list for advancing organizational goals after the retreat. I prepared a full retreat report as an ongoing reference for leadership team decision making and prioritization. I also encouraged the group to use the report in a post-retreat debrief. In our own debrief call, the executive director and I shared insights and outlined paths forward to build on the retreat experience and everything generated in the room together.

BUILDING: Growing and evolving with my clients needs. 

As a facilitator who is also an executive coach, I’m able to be a long-term, trusted partner to my clients. Following this retreat, the sponsors asked me to facilitate their annual all-staff meeting. I also began coaching a member of the leadership team whose retreat insights encouraged both her and her manager to invest in her growth, interpersonal communication skills, and executive presence.


If my highly-customized approach sounds like a good fit for your needs, let’s co-create a journey that will suit your goals, people, culture, and operating environment.

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