It Doesn't Hurt to Ask!

Fundraising isn't just about telling your story and making the ask – it's a deeply collaborative process that starts inside your organization.

In this episode, we're joined by Ainsley Chapman, Executive Director of Evangel Hall Mission, a downtown Toronto mission providing services for people experiencing homelessness. With over 20 years in the sector, Ainsley shares how she went from avoiding fundraising entirely to confidently leading an organization that raises $1.3-$1.5M in philanthropy each year. We cover:

• How to bridge the gap between fundraising, finance and program teams by building trust, understanding shared values, and creating genuine internal partnerships

• What authentic, reciprocal donor relationships actually look like

• Why fundraising training demystifies development work and gives nonprofit leaders confidence to lead fundraising initiatives, redirect board energy, and hire the right people

• Creating a fundraising culture across your organization through clear policies and procedures, cross-departmental collaboration, and helping every team member understand the "why" behind their work

If you're a nonprofit leader who feels intimidated by fundraising, struggling with siloed departments, or looking to build more authentic partnerships with your donors, this episode offers practical insights on transforming your approach from transactional to relational and creating an organizational ecosystem where fundraising, finance, and programming truly work together.

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We've all heard the phrase "culture of philanthropy." But what does it really mean? And how do you build one when you're already knee-deep in grant deadlines, donor meetings, and database cleanup?

In this episode, we unpack the elusive culture of philanthropy through a systems change lens – and explain why strong fundraising success isn't just about strategy. It's about shifting the way your entire organization thinks, acts, and works together.

We'll talk about:

• Why fundraising cuts across every part of your organization
• How to recognize if your organization's culture is quietly undermining your fundraising efforts
• What systems change really means – and how to use it to create the conditions for fundraising growth
• Why fundraising can't - and shouldn't - operate in isolation
• The implicit values, habits, and assumptions that shape outcomes more than any plan
• Why building a culture of philanthropy is a continuous, organization-wide effort – not just a checklist

If you've ever wondered how to make a culture of philanthropy real – not just aspirational – this episode offers a fresh, honest starting point for nonprofit leaders and fundraisers alike.

Resources and links:

Your annual report shouldn't just check a box – it's a powerful donor stewardship opportunity to celebrate impact, engage supporters, and make them feel proud to be part of your mission. In this episode from the Fundraising Lab archives, we're joined by Brooke Erickson as we provide expert guidance on creating a donor impact report. Whether you're launching your first report back to donors or rethinking your annual report strategy, this conversation explores how to create donor-centered communications that maximize donor engagement and strengthen donor retention. We cover: Creating donor-centered impact reports that make supporters feel proud and part of the team The art of impact storytelling: sharing client stories safely through amalgams, staff experiences, and volunteer testimonials Building a strategic stewardship program that balances donor appreciation with fundraising appeals If you're planning donor communications or impact reporting, this episode offers practical advice on transforming standard reporting into meaningful stewardship that strengthens donor relationships and retention.

Check out Brooke Erickson and host Cathy Mann on LinkedIn

So, you've got a vision to grow your fundraising program, but you're not sure how to get there.

Whether you're volunteer-led, an executive director flying solo, or building your first fundraising team, the path to sustainable fundraising growth isn't always clear.

In this episode, we break down the real stages of fundraising growth and what is required at each stage – not just in terms of fundraising strategy, but in terms of systems, organizational culture and capacity building.

We're talking about:

• The 4 key stages of fundraising growth (and what to focus on at each stage)
• Why fundraising success depends on alignment across your entire organization
• What it means to invest in a culture of philanthropy that supports fundraising efforts
• Common traps like unrealistic fundraising hiring expectations, weak infrastructure, and the myth of the "lone fundraiser"
• Real-life stories about how fundraising success leads to overwhelm – and practical ways to prevent burnout

We also dig into why financial reconciliation, donor database management, and clear team communication are just as critical as your fundraising plan – and why you might feel like you're spinning your wheels without these systems in place.

If you're navigating the messy middle, stuck between growing pains and big fundraising goals, this one's for you.

It Doesn't Hurt to Ask is the podcast for nonprofit leaders and fundraisers who want to raise more money with less chaos and build systems that last.

Hosted by Cathy Mann, award-winning fundraiser, educator, and founder of The Fundraising Lab, each episode blends decades of sector experience with practical insights you can apply right away.

Whether you're leading a team, writing your first grant, or steering a $2M campaign, you'll find real talk, relatable stories, and strategies rooted in social-change philanthropy.

Every other week, Cathy and her guests break down how strategy, systems, and culture work together so your organization can scale its fundraising from $200K to $2M and beyond, without burning out your people or your mission.