It Doesn't Hurt to Ask! - TopPodcast.com

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No Growth Without a Game Plan: Growing Your Fundraising Strategy Oct 16, 2025

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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.

Resources and links: Check out host Cathy Mann on LinkedIn Download our Four Pillars of Fundraising Guide for free 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

Music: Intro and Outro Music is Fancy Free by Reveille at Soundstripe

Episode 22 - The Work Doesn't End with Signing a Cheque Nov 15, 2022

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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.

Episode 21 - Voluntary Ranting for the Common Good (Replay) Aug 23, 2022

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This is a replay of one of our favourite episodes from last season. In this episode, Simone Joyaux, ACFRE (proclaimed by Cathy as the Grand Dame of Social Change Philanthropy) reviews the do's, don'ts and dilemmas of fundraising for social change. From the professionalism of fundraising to board governance, this wide-ranging conversation will surely leave you thinking about the ethical challenges of philanthropy in new ways.

Episode 20 - Comfortable with Being Uncomfortable (Replay) Jul 26, 2022

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This is a replay of one of our favourite conversations from last season. On today's episode, Cathy sits down with Ajeev Bhatia, Manager of Policy and Community Connections at the Centre for Connected Communities. Ajeev discusses how the situations of his past have transformed into motivation for his future as he charts a new course for philanthropy and invites us to get Comfortable with Being Uncomfortable.

Episode 19 - Research 'n Rage (Replay) Jun 28, 2022

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This episode is a replay of one of our favourite conversations from last season of It Doesn't Hurt to Ask. Dr. Elizabeth Dale is a fundraiser turned academic who studies the giving habits of women and LGBTQ donors as an Assistant Professor at Seattle University's Nonprofit Leadership Management program. Elizabeth's insights are invaluable on both a practical level and in a big-picture way and she's got the research to back it all up! If you've ever wondered about the hows and whys behind philanthropic giving through a gender lens, this is the episode for you!

Episode 18 - Melding Fundraising with Social Change Apr 01, 2022

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On today's episode, Cathy sits down with Paulina O'Kieffe-Anthony, the executive director of SKETCH based in Toronto. Paulina discusses her new role as Executive Director of SKETCH and some of what she's learned in various roles. She also talks about her work in the arts with racialized and marginalized youth. She then talks through how having a strong fundraising plan and database has been a game-changer for SKETCH. And finally, talks about her hopes for what is to come in the industry and what young leaders can bring.

Join our free fundraising plan webinar: https://fundraisinglab.ca/webinar

You can find more info about Spark Premium, and our new course, Donor Database Essentials: https://www.fundraisinglab.ca/spark/database

Episode 17 - Simplifying Comms Through Functional Fun Mar 03, 2022

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In this episode of 'It Doesn't Hurt to Ask,' the Fundraising Lab's Anne LeMesurier talks with David Phu from Nonprofit Video Comms. We learn about how small to mid-sized nonprofits can look to simplify their marketing communications while increasing impact using simple and targeted video. David and Anne discuss different types of audiences, where you should spend your time and money, strategies for success and what data you should be paying attention to. You can also join our Spark Community for FREE: https://www.fundraisinglab.ca/spark

Episode 16 - Lessons In Resiliency Feb 01, 2022

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On today's episode, Cathy sits down with Sharon Redsky, the Principal at Redsky Fundraising. Sharon discusses how community has the ability to be transformed through intentionality and deepening relationships with partners. She discusses finding common ground, investing in women and the ongoing resiliency of the indigenous community. Join our Spark Community for FREE: https://www.fundraisinglab.ca/spark

Episode 19 - Comfortable with Being Uncomfortable Dec 12, 2019

Show notes

On today's episode, Cathy sits down with Ajeev Bhatia, Manager of Policy and Community Connections at the Centre for Connected Communities. Ajeev discusses how the situations of his past have transformed into motivation for his future as he charts a new course for philanthropy and invites us to get Comfortable with Being Uncomfortable. Get more great podcasts at www.fundraisinglab.ca/resources Great news! It Doesn't Hurt to Ask! is in the top 25 fundraising podcasts to listen to on Feedspot.

Episode 14 - On Being Good-ish Oct 03, 2019

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Ken is the President and CEO, William Osler Health System Foundation and has just been named the 2019 Outstanding Fundraising Professional by the Association of Fundraising Professionals Greater Toronto Chapter. Ken is a quiet shift disturber in our sector this conversation reflects the things he has done to shift and serve the sector. Shout outs to Dr. Krishan Metha, Emma Lewzey, Marni Spears, Kulvir Singh Gill, Rickesh Lakhani.

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