Corporate America delights in facilitated strategic planning sessions, and I've sat through dozens of them. I suspect that it's alumni of those sessions who go to their next temple board meeting and say, We ought to have a workshop. And they're right, they should. On another day, we can discuss why; for today, let's focus on how.
1. Make sure you have a clear objective in mind -- that's what we'll discuss next time.
2. Plan it far enough in advance that Board members' calendars are still clear for the scheduled time -- and sell the program hard, so you have substantial if not total audience.
3. Choose your facilitator with care, someone who knows the synagogue world. If your congregation is part of URJ, the Dept. of Synagogue Management will provide a trained member either of its staff or of its cadre of well-qualified volunteers. This URJ service is offered at no charge -- you're not even responsible for your facilitator's travel expenses. Using URJ gives you assurance that your session will be led by soneone who fulfills these basic criteria -- the facilitator needs to be someone who is intimately familiar with the environment and has no direct stake in the outcome.
When I say, knows the synagogue world, I do not mean "is a member of a synagogue." To give just one example, I attended one Friday-to-Sunday workshop for synagogue leaders where the (corporate)facilitator, recognizing that the group was behind on her planned schedule, suggested that we catch up by skipping Shabbat services. In addition to not getting her way, she lost credibility with the group and thus limited her own effectiveness.
4. Remember the Torah as well as the kemach. (Pirkei Avot -- if there is no nourishment (kemach, lit. grain or meal), there can be no Torah; if there is no Torah, there can be no nourishment.) Your synagogue workshop, whatever its material objective, has to have as a not terribly hidden objective, enriching the participants Jewishly.
5. Provide a comfortable venue, reasonably safe from interruptions If you're going to be in the synagogue, choose a time when no one else will be. Include food! Use mealtime so participants can informally chew over the discussion that has preceded.
6. Start close to on time. Ending early is OK, but ending after the scheduled adjournment time is a no-no. A typical Sunday workshop that starts at 9 AM must end by 3 PM. And let people leave with a sense of resolution.