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.

Join Cathy and Laura Manning, Executive Director of the Lyle S. Hallman Foundation as they discuss the foundation's shift from program-based funding to providing General Operating Support (read: unrestricted funding!) to some of their grantees. The Lyle S. Hallman Foundation is a real shift disturber with a board that gets excited about doing things differently. Tune in to hear about their approach to values-based philanthropy.

It Doesn't Hurt to Ask! podcast is back after a little hiatus. In this episode, Cathy sits down with Chris Baylis of The Sponsorship Collective to discuss the "secretive" world of cause sponsorship. Chris is a self-confessed sponsorship geek. After several years as a "sponsor," Chris decided to cross over to the sponsorship sales side where he has personally closed tens of millions of dollars in sponsorship deals. Chris has been on the front lines of multi-million dollar sponsorship agreements.

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. 

Cathy interviews Jennifer Bernard, CEO of Women's College Hospital Foundation in Toronto. Jennifer is passionate about equity, social justice and innovation and through her work at WCHF, Jennifer is bridging traditional philanthropy with social change through the work of increasing access to healthcare for underserved populations. Jennifer speaks about the groundbreaking work of WCH, her career trajectory and mentorship, particularly her opportunity to become a mentor to young leaders.

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!

In this episode, Cathy sits down with Anne Gloger, who has been shift disturbing for 20 years as the founding director of East Scarborough Storefront and the Centre for Connected Communities. Anne speaks candidly about her journey towards seeing funders as true partners in the work of community building and discusses how difficult it can be to make magic visible to donors. What magic, you ask? The magic that happens when you bring together anyone and everyone who want to help the community thrive. For all you reluctant or resistant fundraisers out there, this is the episode for you!

Are we donors, or are we dancers? In this episode of It Doesn't Hurt to Ask! Cathy sits down with Elissa Beckett of Tides Canada, Canada's least known 30 million dollar charity. In this episode, Elissa shares her experience with innovative approaches of collaborative fundraising and shares her insights on how to collaborate effectively (spoiler alert: leave your ego at the door!). In fact, choreographing collaborations and dancing with wallflowers may just be the future of our sector. 

"Why do you give?" It's such a personal question. But what can the answer tell us about how to design philanthropy? How can design-thinking be applied to build a more human and inclusive approach to philanthropy? And how can we use design to create new approaches to philanthropy that can have the greatest impact? 

To answer these big, bold questions, Cathy sits down with Zahra Ebrahim, a human-centered designer, urbanist and philanthropist who has worked in charitable organizations and now applies her learnings from the social sector to the public and private sector. For full shownotes, visit our website www.itdoesnthurttoaskpodcast.com 

Want to know how to become faster, higher, stronger & get your organization to digital-first place?

In this episode we chat with Jason Shim, Director of Digital Strategy at Pathways to Education Canada. Beyond departmental tactics, for an organization to truly become digital-first, digital should be woven into the overall fabric of your organization. From cryptocurrency to digital councils to intergenerational mentorship, Jason Shim shares his insights and experience about how to use digital technology for good. 

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. 

Change is coming for the philanthropic sector. And it doesn't care what you think about it. In this episode of It Doesn't Hurt to Ask! we chat with Marina Glogovac, CEO of CanadaHelps.org about the shifts we're facing as a sector. 

How are charities going to evolve? What does the sector need to do to make sure we adapt? This episode is all about the disruptive forces coming for the charitable sector: technology, crowdfunding and maybe surprisingly, humility. 

For full show notes, visit www.itdoesnthurtotask.com 

In this episode of It Doesn't Hurt to Ask! Cathy has an open and honest conversation with Lisa Watson of Openly about how our money values and personal relationship with money - ie our 'money mindset' can manifest in the ways we work in the charitable sector. Lisa and Cathy talk about the work they're doing as a team to challenge charitable sector leaders to have courageous conversations about money and how our beliefs around money need to shift for the benefit of the organizations we work with. Not one to miss!

It's hard to introduce Dr. Krishan Mehta because he does so many things! His day job is AVP Engagement, University Advancement at Ryerson University. He self-identifies as a nerd, but to us and many others, Krishan is an innovative fundraiser, a shift-disturbing thought leader, and a dedicated researcher. In this episode, we chat with Krishan about the subject of his PhD research: how high net worth immigrants are participating in the charitable sector in Canada; diversity and inclusion in philanthropy and the state of research in our sector. 

For full show notes, check out www.itdoesnthurttoaskpodcast.com

Questions, kudos, concerns? It Doesn't Hurt to Ask! Drop us a line hello@cathymann.ca 

In our inaugural episode of It Doesn't Hurt to Ask! Cathy interviews Sharon Avery, CEO Toronto Foundation and finds out just how much shift Sharon is bringing to the charitable sector. Not only is Sharon not afraid to ask for money (spoiler alert - she loves it!) she believes in shaking up long-held traditions within philanthropy by promoting social change philanthropy on a large scale. In this episode, we chat about challenging the rules of philanthropy, the Toronto Foundation's visionary approach to engaging Next Gen philanthropists and women, collaborative fundraising and how Sharon's next big thing is all about inspiring a movement of radical generosity.

For full show notes, check out www.itdoesnthurttoaskpodcast.com

Questions, kudos, concerns? It doesn't hurt to ask! Drop us a line hello@cathymann.ca 

Introducing Cathy Mann, your host of It Doesn't Hurt to Ask! Welcome to Season One. 

After spending over 25 years as a professional fundraiser working in philanthropy, Cathy knows a thing or two about the charitable sector.

We're a sector that is... what shall we say...  comfortable with tradition. 

But the world is changing and it's time for us to change too. We're facing competition from industries we didn't even know existed a decade ago. So where does that leave a risk-averse sector faced with a world of disruption? 

In true It Doesn't Hurt to Ask! fashion, we started asking some questions.

Listen, learn and laugh along with us to find out. 

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

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

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

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.

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

Resources and links:
Check out Brooke Erickson and 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

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 gifts strategies for turning that initial meeting into a long-term donor relationship.  

Together, we walk through the critical elements of successful major donor meetings – from donor prospecting research and goal setting to asking the right discovery questions and creating clear next steps.

We cover:

• How to research major donor prospects, set meeting goals, and understand their giving patterns and priorities
• The art of discovery calls: asking the right questions, listening well, and learning what donors truly care about
• Creating effective calls to action and securing permission for meaningful follow-up that moves the relationship forward 

If you're preparing for your first major gift meeting or looking to strengthen your major donor cultivation strategy, this episode offers practical fundraising best practices to help you build authentic relationships with foundation funders and high-capacity donors. 

Resources and links:
Check out Debra Thompson 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

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

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

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.

Resources and links:
Check out host Cathy Mann on LinkedIn
Book your Fundraising Growth Game Plan call
Email us at hello@fundraisinglab.ca
Subscribe to our email list

Podcast editing and post-production by: Daniella Sorrentino at Feral Culture Lab (feralculturelab.com) 

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