Confident Fundraising Conversations

Fall 2026 Fundraising Series Day 3 – Making the Ask with Confidence – Turning Strategy Into Real Conversations and Real Results

Even with strong systems in place, many nonprofit professionals still hesitate at the most critical moment: the ask.

This session is hands-on, practical and confidence-building. There will be space to practice, refine, and build comfort with real-world fundraising conversations. We move beyond theory into lived experience to help participants find language that feels natural, grounded and aligned with their mission.

Participants will:

• Learn how to craft compelling appeals
• Practice how and when to deliver an ask in writing, at an event, in a small group, or one-to-one
• Leave with increased confidence and skill in making clear, compelling asks that invite donors into meaningful partnership

This training is part of the Fall 2026 Fundraising Series – Building Resilient Organizations, Sustainable Revenue, and Confident Askers

What if fundraising didn’t feel reactive, overwhelming, or dependent on a few high-stress moments each year?

What if it felt steady, aligned, and grounded in the kind of organization you’re actually building?

This three-day workshop series is designed for nonprofit leaders, development staff, and board members who want to move beyond short-term tactics and build a sustainable, relationship-centered approach to fundraising.

Participants can attend one, two, or all three days as each session stands on its own while also building toward a cohesive, long-term strategy.

• Sept. 22 – Day 1 – Organizational Resilience & Strategic Alignment for Fundraising Success
• Sept. 23 – Day 2 – Creating Sustainable Revenue Systems
• Sept. 24 – Day 3 – Making the Ask with Confidence

The Initiative Foundation’s Nonprofit Academy trainings are part of the organization’s mission to serve the people of Central Minnesota. If your organization is located outside our 14-county and two Native nation service area, please contact Nicole Clements regarding participation options.

Presented by: Janet Cobb

Janet has worked in the nonprofit arena her entire career, holding a variety of positions, including communications manager, director of development, and executive director. Along the way, she has managed budgets ranging from $50,000 to more than $8 million. She holds certifications as a fundraising executive and nonprofit professional.

Nicknamed “The Small Nonprofit Whisperer” by colleagues, Janet has consulted with, coached, or trained more than 700 early-stage, grassroots, and small nonprofits to help them build capacity and acquire the skills needed to support and expand their efforts.

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The Initiative Foundation makes every effort to provide reasonable accommodations in accordance with the Americans with Disabilities Act (ADA), the Minnesota Human Rights Act (MHRA) and Minnesota State Board Policy 1B.4. Members of the general public who require accommodations to attend a public event should complete this form at least 10 business days prior to an event when practical.