If you want to loosen up a development team at the start of a planning session, try this: ask everyone to share a piece of slang from their generation—and define it. You’ll get everything from “groovy” to “on point” to “it’s giving,” usually followed by laughter, mild confusion, and a few good-natured eye rolls. It’s a small exercise, but it does something important: it surfaces the reality that people on your team don’t just bring different skills—they bring different cultural reference points, communication styles, and assumptions about work itself.
Here’s how to run it effectively without letting it derail your agenda. Keep it short—five to seven minutes total. Ask each person to share one term, what it means, and (if they’re willing) when they tend to use it. As facilitator, go first to model brevity and tone. Capture a few of the words on a whiteboard or shared screen; they often become shorthand jokes you can reference later in the meeting to keep energy up. If your team is larger or time is tight, have people pair up and then report out one favorite term per pair. The goal isn’t the slang itself—it’s creating a quick, low-stakes moment of participation that signals every voice is welcome.
In a small development shop, that kind of intentional inclusion matters. Spring, anchored around budget development, is an ideal moment to convene the team. It’s a natural inflection point: you have enough insight from the current year to evaluate performance, and enough runway to shape what comes next. But for a small, multi-generational team, the real value lies in how you structure the conversation.
Start by creating a shared foundation. Ground the discussion in clear organizational goals and financial realities, but avoid presenting them as fixed directives. Instead, frame them as a starting point for discussion. This is especially important across generations—more experienced staff may be accustomed to top-down planning, while newer team members often expect a more participatory approach. Setting the tone early that all perspectives are welcome helps bridge that gap.
Next, build in structured reflection. Invite the team to assess what worked and what didn’t over the past year, but be intentional about how you solicit input. Some team members will jump into discussion; others may prefer to gather their thoughts first or contribute in writing. A mix of formats ensures you hear from everyone—not just the most vocal.
This is where generational diversity becomes a strength. A seasoned fundraiser may bring deep knowledge of donor relationships and long-term strategy, while a younger colleague might offer insights into digital engagement or shifting donor expectations. When these perspectives are surfaced and respected, your planning becomes more grounded and more forward-looking.
As you move into forward planning, shift from reflection to co-creation. Rather than assigning goals and tactics, facilitate a conversation around priorities. Ask where the greatest opportunities lie, which donor segments are underdeveloped, and what new approaches are worth testing. Encourage the team to challenge assumptions—including your own. In a small team, buy-in isn’t optional; it’s what makes execution possible.
A strong development work plan that emerges from this process should be both comprehensive and practical. It begins with clear revenue goals, broken down by funding stream—annual giving, major gifts, grants, events, and corporate support. For a small team, this clarity ensures that limited capacity is focused where it will have the greatest impact.
From there, translate goals into specific, actionable tactics. Vague intentions like “grow major gifts” aren’t enough. Define the work: how many donor visits, what cultivation strategies, which proposals, and when. This level of detail not only improves execution but also creates shared expectations across the team.
Equally important is defining roles. In small teams, people often wear multiple hats, which can blur accountability. A clear plan assigns ownership for each activity while acknowledging collaboration points. This is another area where generational awareness matters—be explicit about responsibilities, but flexible in how work gets done, recognizing different styles and strengths.
Timing is the next essential layer. Development work follows a rhythm, and mapping activities across the year helps prevent overload and missed opportunities. A visual calendar can be particularly effective, giving everyone a shared view of how appeals, events, and deadlines intersect.
Finally, establish a process for tracking progress. A work plan should evolve as conditions change. Regular check-ins—monthly or quarterly—create space to review results, adjust strategies, and maintain alignment. They also reinforce a culture of shared accountability, where everyone understands how their contributions connect to overall success.
When done well, a collaborative planning process does more than produce a document. It creates a shared language—whether you call it “on point,” “groovy,” or something entirely new—and builds the alignment a small, multi-generational team needs to move forward with clarity and confidence.
And if your plan comes together seamlessly? That’s not just good strategy—it’s, as the next generation might say, “low-key iconic.”
Bon chance!
PS Take your planning meeting al fresco for an added creative boost!