5 Ways to Make Your Next Development Retreat More Effective
By Lisa Scott
Most fundraising teams gather once a year — at the annual Development retreat where the team steps back to review goals, plan the months ahead, and maybe engage in a few skill-building exercises. These gatherings matter. They build morale and give people a rare chance to connect outside the daily rush.
In my experience, though, for Development teams they rarely change how the team actually raises money. People leave with a fresh set of goals and insights, but (mostly) the same habits they arrived with. And within a few weeks, the pace of the work pulls everyone back into the status quo.
Recently, my colleague Jeremy Cramer and I led an immersive retreat for a group of 25 small nonprofits in the Northeast. It reminded me how much more a team gathering can accomplish when it's designed around the way fundraising – in this case for transformational gifts – actually comes together.
Here are five elements that made the difference, and how you can build each one into your own retreat.
1. Pair every concept with practice
Most retreat agendas are built around presentations and discussion. Those have value, but the most value comes from putting the ideas into practice and getting feedback.
At our recent TGP Immersive retreat, Jeremy introduced our take on exploratory conversations (aka discovery meetings): what they are, why they matter, and how they set you up for success in Cultivation. Within minutes, participants were practicing those conversations with one another, using a copy of our Major Gift Conversation Starter as their guide.
As you build your agenda, look at each session and ask what your team will actually do with the idea before the next session begins. A good balance is to plan roughly as much time for practice as for instruction.
2. Work on real names, not hypotheticals
Sample scenarios are useful for teaching a concept, but a team learns the most when they apply new ideas to real life donors. Ask each person to come prepared with a short list of their own top donors, along with what they already know about each one.
At our retreat, when we grouped participants by organization, each team sat together and built a Cultivation Team, Cultivation Strategy, Solicitation Plan, and Stewardship Plan around real names from their portfolio.
The benefit of this approach continues long after the retreat ends. Instead of returning with general ideas, your team returns with specific next steps for specific donors, ready to act on the following week.
3. Mix people up for practice and feedback
Practicing a donor conversation with a colleague you see every day can feel risky, and feedback from a close teammate can feel loaded. But, role-play is the most effective tool to build your skills and confidence.
You can work around some of this fear by pairing people across locations, but what’s most important is to set the ground rule that what’s shared stays here and what’s learned leaves here, to make the retreat a safe space for your team to try something new and hear genuinely constructive feedback from a peer.
4. Bring a donor's perspective into the room
This is the step most teams skip, and it may be the most valuable one. Whenever possible, we invite actual donors to take part in our training, and this retreat showed why.
The funder who supports these organizations joined us for the day. After participants practiced their exploratory conversations, Jeremy modeled one live with him.
His candor was eye-opening. And in the Solicitation training, he described the mistakes nonprofits make most often, including asking him for too little money. You could feel the room shift as people realized how much they had been leaving on the table, and how often fear had been shaping their asks.
That kind of insight is very difficult to get any other way. When a donor becomes part of the discussion, your team learns about donor motivations and aspirations in a way that rarely surfaces through everyday cultivation.
5. Leave with one shared process and language
A retreat is one of the few times your whole team learns together, which makes it the ideal moment to align on how you approach every donor relationship. When everyone follows the same steps and speaks the same language, each donor receives a consistent, best-in-class philanthropic experience regardless of which staff member they're talking to.
This matters even more when donors are shared across sites, or between a site and headquarters, where relationships can stall in handoffs or mixed messages.
At TGP, that shared language and process is what we call the Strategic Relationship Management Cycle, the framework at the heart of The Transformational Giving Playbook™, and we structured our entire retreat around it. If your organization already has a donor cycle and a process that works, use the retreat to reinforce it. If it doesn't, use the day to establish one, and make sure everyone leaves knowing how it applies to their own portfolio.
“What I appreciated most was how they brought structure and strategy to something I’ve intuitively understood for years. I’ve always known the importance of relationships, storytelling, engagement, and making meaningful connections but today’s training helped me connect all of those pieces and better understand the strategy behind successful fundraising.
~ Chief Development Officer, Education Nonprofit
Schedule your nonprofit Development retreat before fiscal year-end
If you're planning your next team gathering, consider what it could accomplish beyond improving morale. You could hold the usual Development retreat, or you could choose an experience that delivers the same team-building benefits while also strengthening donor strategy, sharpening your team's skills, and aligning everyone around a proven process.
When a team learns, practices, and strategizes together, the culture of philanthropy you've been working toward begins to take shape in the room, and it travels home with every person who was there.
Want support in planning your next Development retreat?
If you have your next retreat on the books, but aren't sure about the agenda, we'd be happy to take on all or part of that for you. Request a meeting and we'll talk through your budget and what we can accomplish for you.