Lead the Ask

Stop asking your nonprofit board to "bring five names." In this episode of Lead the Ask, Holly Kobia of Kobia Consulting explains why that approach to board fundraising rarely works, and what to do instead to build a stronger donor pipeline.

Holly walks through the better questions that help board members identify real prospects: people connected to your mission, affected by the problem you're solving, already philanthropic, or open to an introduction. She covers the difference between a prospect and a donor, why warm introductions matter, how to avoid damaging trust with board members, and the many ways your board can support fundraising without becoming your sales team.

You'll leave with a simple 15–20 minute exercise to run at your next board meeting: pick one priority, map your connections, and assign a clear next step to every relationship.

Because sometimes getting clearer means we stop asking, "Who do we know?" and start asking, "Who should know us?"

Follow Lead the Ask for more on nonprofit fundraising, board engagement, and leadership. Fundraising gets easier when leadership gets clearer.

Your donor pipeline isn't going to build itself.

Most nonprofits say "we need more donors", but the better question is "who do we already know who can help us meet them?" In this episode, Holly Kobia explains why pipeline development is a leadership function, not something that belongs exclusively to your development director, and why fundraising only works when the whole organization treats relationship-building as part of advancing the mission.

Holly shares what actually belongs in a donor pipeline (it's more than a list of names), the low-pressure questions that get board members and staff comfortable making introductions, and this week's Lead the Ask challenge: a simple 30-minute exercise to start filling your pipeline today.

Fundraising gets easier when leadership gets clear. Now go lead the ask.

I want to talk about something most nonprofits don't do enough: celebrating your wins.

In this episode, I break down why so many organizations go quiet after a big gift, grant, or campaign milestone, and why that instinct gets the psychology backwards. Donors don't want to fund an organization that looks like it's barely hanging on. They want to invest in momentum.

I'll walk you through the framework I use with clients: celebrate the generosity, connect it to the impact, show the momentum, clarify what remains, and invite others into what comes next. You'll leave with real language you can use the next time your team lands a gift worth celebrating.

Fundraising gets easier when leadership gets clearer. Lead the vision, lead the conversation, lead the ask.

New episodes every Tuesday. Subscribe so you don't miss the next one.

#LeadTheAsk #FundraisingLeadership #NonprofitLeadership #HollyKobia #BoardDevelopment

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Americans gave nearly $600 billion to charity in 2024 — so why are so many nonprofits still struggling to hit their fundraising goals? Holly Kobia breaks down the latest Giving USA data and what it actually means for your organization as you plan for the year ahead.

She walks through five major giving trends — from the concentration of wealth among high-capacity donors, to the growing importance of planned giving, to why corporate sponsorships are getting way too much attention from small nonprofits. (Spoiler: individuals still account for two-thirds of all charitable giving. Are you spending two-thirds of your time there?)

You'll walk away with three concrete things to focus on: building a donor pipeline, developing a board that opens doors, and creating a stewardship system that keeps donors coming back. The money is out there. The question is whether your organization is positioned to receive it.

If you could double your fundraising without finding a single new donor, would you be interested?

Most nonprofits are leaking donors faster than they're acquiring them. And the biggest growth opportunity you have is already sitting in your donor database.

In this bonus episode, Holly breaks down why stewardship isn't just a thank you letter — it's your most important fundraising strategy.

You'll hear why donor retention is the hidden crisis we've all accepted as normal, how to build a simple A/B/C donor category system, the four levels of stewardship that actually move the needle, and why donors leave quietly (and what we can do about it).

The people who've already said yes to your mission deserve your attention first. The next gift often begins the moment the last gift is received.

Most nonprofits think they have a fundraising problem. More donors, more events, more staff — that's what they're after. But after years working in fundraising, communications, and leadership, Holly Kobia has a different diagnosis: the real problem starts at the top.

In this debut episode of Lead the Ask, Holly breaks down why fundraising is a leadership issue — not a development department issue — and what that means for your organization's culture, clarity, and consistency. From the habits that quietly undermine donor relationships to the systems that high-performing nonprofits swear by, Holly gets real about what's holding your fundraising back and exactly what to do about it.

In this episode:

• Why fundraising culture lives inside leadership, not the development office
• The most common mistakes leaders make (and don't realize they're making)
• How to move from reactive fundraising to a steady, confident rhythm
• What strong fundraising organizations do differently
• This week's challenge: take an honest look in the mirror at your fundraising culture

Lead the Ask is for nonprofit leaders, fundraisers, and board members who are ready to skip the fluff and do the real work of fundraising.

Follow Holly on LinkedIn | @leadtheask on Instagram | New episodes drop the last Tuesday of every month.

Fundraising gets easier when leadership gets clearer. Lead the Ask is the podcast for nonprofit leaders, fundraisers, and board members who are done guessing their way through fundraising and ready to do the real work.

Host Holly Kobia — former TV journalist turned fundraising professional with $100M raised at Virginia Tech — cuts through the fluff and gets into what fundraising actually looks like day to day. We're talking practical strategy, donor psychology, board empowerment, major gifts, stewardship, and the hard conversations nobody else wants to have.

Because fundraising isn't about asking for money. It's about inviting people into something bigger than themselves, and leading them there with clarity and confidence.

Here, we'll lead boldly, ask clearly, and fund that mission.