Why August Might Be the Most Important Month for Your Development Team
A mid-year retreat is one of the most valuable things you do all year.
By the time you're reading this, our team at Contour Strategies will have just wrapped up our annual retreat. It's something we look forward to every year. For a few days, we gather on Andy's farm in Newberg, Oregon, to connect, reflect, strategize, and dream about the future. It's a chance to step away from the daily demands of our work and spend intentional time together as a team.
Ironically, retreat season falls during one of the busiest times of the year. Summer calendars are full, campaigns are moving forward, and everyone is juggling vacations, deadlines, and client engagement. Yet this retreat remains one of the most important things we do all year.
Every time I leave, I feel more connected to our team, more grounded in our mission, and energized to finish the year strong.
What about your organization? Does your team intentionally step away to connect?
I often hear nonprofit leaders say, "We just don't have time for a retreat."
My response is usually the same: You don't have time not to.
The reality is that the year-end fundraising season is closer than you think. Before long, we'll be in the fourth-quarter sprint, working hard to meet annual goals, steward donors, execute campaigns, and finish strong. It's exciting work, but it's also exhausting.
By the time November and December arrive, many development professionals are already running on fumes.
That's why August can be such a strategic opportunity.
The Value of a Mid-Year Reset
When I am helping a client build an Annual Advancement Plan, I almost always schedule a team retreat in August. Not because the team has extra time or there's less work to do, but because it's the ideal moment to pause, evaluate, and prepare for the most important fundraising season of the year.
A retreat gives your team space to ask questions that rarely get the attention they deserve:
What's working well in our advancement strategy?
Where are we getting stuck?
What wins should we celebrate?
What lessons have we learned from our setbacks?
What adjustments do we need to make before year-end?
How can we better support one another?
The answers to these questions often determine how successful the final months of the year will be.
Connection Is a Strategic Investment
Retreats aren't simply about planning. They're about people.
Development work is deeply relational, emotionally demanding, and often high-pressure. Across the country, nonprofit organizations continue to face significant challenges with burnout, turnover, and staff fatigue.
A retreat creates space for something that often gets overlooked: human connection.
When teams spend time together outside of their normal routines, trust deepens. Communication improves. Silos break down. People remember why they do this work and who they're doing it alongside.
Those outcomes may not show up immediately on a dashboard, but they absolutely impact fundraising results.
Healthy teams raise more money.
Connected teams solve problems faster.
Encouraged teams stay engaged longer.
A Sample One-Day August Retreat Agenda
If you're wondering where to start, here's a simple framework I've used with development teams:
9:00 AM – Welcome and Reflection
Celebrate wins from the first seven months of the year
Share donor success stories
Reflect on organizational impact
10:00 AM – Advancement Strategy Review
Year-to-date fundraising performance
Pipeline and donor engagement review
Progress toward annual goals
11:30 AM – Challenges and Opportunities
Identify roadblocks
Discuss resource needs
Brainstorm solutions together
12:30 PM – Lunch and Informal Connection
1:30 PM – Year-End Planning Session
Review fourth-quarter campaigns
Clarify priorities
Assign responsibilities and next steps
3:00 PM – Team Development Discussion
What's helping our team thrive?
What's causing stress or frustration?
How can we better support one another?
4:00 PM – Vision and Encouragement
Reconnect to mission
Share hopes and goals for the remainder of the year
5:00 PM – Wrap-Up
Give Your Team Permission to Recharge
Sometimes leadership means pushing forward and sometimes leadership means creating space to pause. The strongest teams don't wait until they're exhausted to recharge. They build rhythms of reflection, connection, and renewal into their culture.
As you look ahead to the second half of the year, consider giving your team that gift.
Step away.
Reflect.
Strategize.
Encourage one another.
Then head into year-end with renewed clarity, energy, and purpose.
