How to Have a Successful Retreat: Walk on Water

Bob Denney • July 31, 2024

Planning and conducting a successful retreat is like walking on water—it’s a lot easier if you know where the rocks are. The best way to find the rocks is to follow certain guidelines. Some of them apply to every retreat, regardless of the firm. Others vary, depending on the purpose of the retreat and the culture and goals of the firm.


Some of the Reasons for Holding a Retreat

  • To develop or approve a strategic plan. This is serious business.

  • To discuss a major issue—such as a possible merger or new compensation plan—or to launch a new marketing or business development program. This is also serious business.

  • To discuss the “state of the firm.” This may be serious business.

  • To provide an opportunity for the members of the firm—or all the attorneys—to communicate and socialize together. This is important.

  • Even if there is no serious business, it is wise to hold a retreat annually. It is no coincidence that the firms with strong cultures and good internal communications generally hold an annual retreat.

Planning the Retreat

  • Clearly define the objectives—and be sure they can be accomplished.

  • Begin planning far in advance; three months is the bare minimum. Size is a factor here. A retreat for 200 people requires considerably more planning than a retreat for ten.

  • Once firm management has decided on the purpose and objective of the retreat, appoint a Retreat Committee and let them plan the retreat.

  • The objective will determine who should attend all or at least part of the retreat: partners only, all lawyers, administrative managers, support staff? In any event, be certain that all firm leaders attend.

  • Invite input, by questionnaire or interview, from those who will attend, on what they feel should be on the agenda.

  • Don’t include routine operations matters on the agenda. These belong in regular management or partner meetings.

  • Hold on a weekend. Begin Friday. End by mid-afternoon Sunday.

  • In most cases, select a site which will require everyone to stay overnight. The additional cost is worth it. Some of the best discussions occur over a drink after dinner or during a walk before breakfast.

  • If it is a serious business retreat, consider having an experienced outside facilitator who will also be involved in planning the retreat.

  • The best schedule for a serious business retreat is no more than three sessions, no longer than three hours each. Make sure that all topics can be properly addressed.

  • Don’t schedule business sessions after dinner.

  • Distribute the agenda well in advance along with any reports or “white papers” the attendees should review beforehand.

  • The recreational facilities needed—golf, tennis, fitness centers, etc.—depend on the attendees’ interests as well as the purpose of the retreat. Recreational time for a social retreat will be greater than for a serious business retreat. But, even in the latter case, break time is needed to allow ideas to percolate and the mind to breathe. 

  • Plan and check out every detail in advance. Murphy’s Law applies to retreats as well. 

Conducting the Retreat

  • Strive for participation by everyone who attends. No one should be allowed to hold his or her comments until a later date. On the other hand, no one should be allowed to dominate the discussions. These are some of the factors an outside facilitator can generally handle better than someone from the firm.

  • Most people participate more actively in smaller groups so include break-out sessions for in-depth discussion followed by reports to all attendees for further discussion as needed.

  • Be sure all post-retreat, follow-up steps are understood and assignments made. 


Post-Retreat Follow-Up

  • Distribute to all appropriate parties minutes or a summary of the retreat. This is the final responsibility of the Retreat Committee and should be done promptly, i.e., within a week.

  • It is usually the responsibility of firm management to ensure that all follow-up action steps are taken and that the schedule for completing them is adhered to.

  • Feedback is important. Firms often have all attendees complete an evaluation form at the close of the retreat and turn it in before they leave.

A successful retreat is a tremendously uplifting experience—just like walking on water! In both cases it is worth the time and effort to determine where the rocks are.


Bob Denney is a recognized authority on strategy, management and leadership for law firms and companies. He serves as an outside Director on company boards and has also served as an interim CEO in turnaround and crisis situations. https://www.linkedin.com/in/robert-denney-374602a/

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By Dan Baldwin January 30, 2025
Contact Fox Law, APC 201 Lomas Santa Fe Drive Suite 420 Solana Beach, CA 92075 (858) 256-7616 www.foxlawapc.com
By Dan Baldwin January 30, 2025
Contact Fox Law, APC 201 Lomas Santa Fe Drive Suite 420 Solana Beach, CA 92075 (858) 256-7616 www.foxlawapc.com
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