Smaller churches tend do strategic planning retreats in August because they think of the program year from September through May; larger churches tend to do these retreats in November because they think of the program year from January through December. (Southern hemispheres folks reverse the seasons). If you want to start “thinking big”, you should try moving your planning retreat to November.
Regardless, the summer is the time when leaders start planning the planning retreat. There is still time if you are looking to August. Always start with a review of your church DNA; list programs and creative ideas; and list key staff and volunteer leaders who need to attend the planning retreat. Set the date, contact the people. Let them have enough time to gather relevant information about why, when, where, how, and who so that leaders can do good work.
The pastor needs to take a very strong role in leading this retreat. Don’t take a back seat. Don’t pretend to simply be a resource to the people. You’re the spiritual leader. This is the time to cast your concrete vision for the coming year or two, focus your benchmarks for success, and clarify your expectations (spiritual and practical) for current and emerging leaders. Summer is the time to think about this in advance.