It Doesn't Hurt To Ask: Lessons from the Trenches with Sarah Bass
Release Date: 01/22/2026
It Doesn't Hurt To Ask: Lessons from the Trenches with Sarah Bass
It Doesn't Hurt to Ask!
You don't need to have all the answers to be a successful fundraiser – but you do need the confidence to ask better questions and the right community to support you along the way. In this episode, hosts Cathy Mann and Erin Boyce sit down with Sarah Bass, former Manager of Fundraising Communications at Community Counseling Resource Center (CCRC) in Peterborough. Sarah shares her honest journey of falling into fundraising, inheriting a program without strategy, and navigating a database migration during the pandemic. From discovering her donor data wasn't as organized as she...
info_outline
The Data Isn’t Broken—Your System Is: When Good Plans Meet Bad Data
It Doesn't Hurt to Ask!
Fundraising data problems aren’t just annoying – they're strategic barriers to your fundraising success. In this episode, we’re joined by Erin Boyce, Fundraising Lab’s Data and Digital Director aka in-house database expert, who shares deep insights into why even the best fundraising plans can unravel without the right systems and processes in place. Together, we get real about the messy reality of managing fundraising data – from mismatched reports and inherited spreadsheets to donor management systems (CRMs) that don’t integrate with your finance...
info_outline
Corporate Courtship: Attracting Sponsors to Your Program with Logan Stengel
It Doesn't Hurt to Ask!
Landing corporate sponsorships isn’t just about having the perfect sponsorship deck – it's about building relationships and understanding what businesses actually need from their investment. In this episode, we’re joined by Logan Stengel as we discuss branching out from small-town sponsors to bigger corporate partnerships. If you’ve ever sent sponsorship packages into the void or struggled to get past online portals, this conversation explores how to shift from transactional asks to strategic business-to-business relationships that deliver real value for both...
info_outline
Fundraising Culture from the Inside Out an Interview with ED Ainsley Chapman
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...
info_outline
The Shift Hits the Fan - Dealing with Systems Change
It Doesn't Hurt to Ask!
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...
info_outline
Stewardship: How to Maximize Donor Reporting with Brooke Erickson
It Doesn't Hurt to Ask!
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...
info_outline
No Growth Without a Game Plan: Growing Your Fundraising Strategy
It Doesn't Hurt to Ask!
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...
info_outline
It Doesn't Hurt to Ask - The Reboot Teaser
It Doesn't Hurt to Ask!
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,...
info_outline
The Mysteries of Major Gifts Revealed with Deb Thompson
It Doesn't Hurt to Ask!
That first major donor meeting can feel intimidating – but with the right preparation and strategy in place, it’s an opportunity to build a meaningful philanthropic relationship that could transform your organization’s impact. In this episode from the Fundraising Lab archives, we’re joined by Deb Thompson as we provide expert fundraising coaching on how to prepare for an upcoming major gifts meeting with a prospective foundation funder. Whether you’re reconnecting with a past supporter or meeting with high-capacity donors for the first time, this conversation covers essential major...
info_outline
Episode 22 - The Work Doesn't End with Signing a Cheque
It Doesn't Hurt to Ask!
Tune in as Cathy interviews Paul Taylor, Executive Director of FoodShare Toronto. Paul is a lifelong anti-poverty activist who has used his experience to fuel a career focused on helping others and dismantling the beliefs and systems that lead to poverty and insecurity.
info_outlineYou don't need to have all the answers to be a successful fundraiser – but you do need the confidence to ask better questions and the right community to support you along the way.
In this episode, hosts Cathy Mann and Erin Boyce sit down with Sarah Bass, former Manager of Fundraising Communications at Community Counseling Resource Center (CCRC) in Peterborough. Sarah shares her honest journey of falling into fundraising, inheriting a program without strategy, and navigating a database migration during the pandemic. From discovering her donor data wasn't as organized as she thought to learning how to communicate impact without client testimonials, this conversation is full of practical wisdom and reassurance that we're all "fumbling through" together. We cover:
-
How to gain clarity on what actually moves the needle versus what just fills your calendar when you inherit a fundraising program
-
The transformative power of strategic fundraising guidance and understanding what will "maximize your bang for your buck"
-
Why your fundraising database and finance system serve different purposes and how to separate fundraising metrics from accounting reports
-
Developing outcome-focused messaging that resonates when you can't use testimonials or client stories
-
The importance of fundraising community and mentorship for combating isolation as a solo fundraiser
If you're a solo fundraiser feeling overwhelmed, struggling with data management, or trying to refine your approach without clear direction, this episode offers practical advice and the reminder that you're not alone in this work.
Resources and links:
-
Check out Sarah Bass, Erin Boyce and host Cathy Mann on LinkedIn
-
Book your Fundraising Growth Game Plan call
-
Email us at hello@fundraisinglab.ca
-
Subscribe to our email list
-
Share this episode with a friend!
Podcast editing and post-production by:
Daniella Sorrentino at Feral Culture Lab (feralculturelab.com)
Music:
Intro and Outro Music is Fancy Free by Reveille https://app.soundstripe.com/songs/16267