Turning “Dead” Months Into Strategic Opportunities: Planned Giving

by Senior Consultant, Mitra Karami

The quieter months of the year, often January, June, or late summer, offer a unique opportunity for nonprofits to introduce or elevate their planned giving programs. These periods naturally lend themselves to reflection: donors are reviewing finances, updating paperwork, or rethinking long-term priorities. When approached with care and clarity, planned giving becomes an invitation rather than an ask.

Why Planned Giving Works in “Dead” Months

Planned giving conversations are fundamentally different from year-end appeals. They’re not about immediate revenue. They’re about legacy, values, and vision. After the intensity of Giving Tuesday and holiday campaigns, donors appreciate softer engagements that offer long-term value rather than another gift request.

These quieter months are ideal because:

• Donors have mental space to think about estate planning without the noise of holiday demands.

• Financial planning naturally occurs at the start and midpoint of the year.

• Reflection and goal-setting pair well with conversations about impact and legacy.

• There’s no urgency pressure, which allows donors to explore options at their own pace.

  
  

How to Make Planned Giving Accessible and Appealing

Planned giving feels intimidating for many supporters. Your role is to make it approachable, flexible, and donor-centered. Consider these strategies:

1. Host a Virtual Planned Giving Webinar or Info Session: A light-touch educational event can be transformative. Offer a 30–45 minute session covering:

   1. What planned giving is (and isn’t)

   2. Simple ways to make a legacy gift (no attorney needed)

   3. Common myths and misconceptions

   4. How planned gifts sustain the mission for generations

   5. Real donor stories (if available)

2. Partner with one of Ostara’s planned giving experts to guide the discussion. This positions your organization as a resource, not a solicitor—and donors deeply appreciate the opportunity to learn without pressure.

3. Lead with Values, Not Technicality: Instead of focusing on tax benefits first, anchor your messaging in impact:

   1. “A planned gift ensures future generations benefit from the work you care about today.”

   2. “Legacy gifts keep our mission thriving beyond your lifetime.

   3. “By including our organization in your estate plans, you become part of our long-term story.”

   4. Donors respond to purpose, belonging, and continuity.

Final Thoughts: Slow Seasons Are Strategic Seasons

Dead months don’t have to be dead at all. With thoughtful, low pressure engagement strategies and focusing on planned giving, organizations can turn the calendar’s quietest moments into catalysts for long-term growth.

If you want support building a year-round fundraising plan or strengthening your donor engagement strategy, The Ostara Group is here to help.