Ep. 68 | How to Start a Fundraising Conversation Without Feeling Pushy

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Struggling to fundraise?

This FREE & LIVE workshop will help you break free from the guilt and discomfort around asking for money — and confidently invite people into the mission God gave you.

Get ready to:

1. Stop Feeling Embarrassed About Asking for Money

2. Know Exactly How to Start the Conversation

3. Invite Support with Confidence

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Let’s just say it out loud.

Fundraising can feel… gross.

Not because you don’t believe in your ministry.

Not because it doesn’t matter.

But because every time you go to ask for support, something in you tightens.

You start thinking:

• I don’t want to bother them

• I hope they don’t feel pressured

• Why would they even give to me?

And suddenly, something that should feel meaningful…

just feels heavy.

It’s Not That You’re Pushy—It’s That You’re Unsure

This is where most people get it wrong.

You think the problem is that fundraising feels pushy.

It’s not.

The real issue is this:

You’re not fully convinced you have something valuable to offer.

So when you ask, it feels like you’re taking.

And when it feels like you’re taking…

of course it feels awkward.

It feels like:

• You’re asking from a place of lack

• They’re in control

• You’re hoping they say yes

That’s not confidence.

That’s vulnerability without clarity.

You Have to Actually Believe This Benefits Your Donor

Here’s the shift.

Fundraising is not:

“Can you give me money to keep this going?”

It’s:

“Do you want to be part of what God is doing here?”

That’s a completely different posture.

But you don’t get to say that unless you actually believe it.

And this is where you need to get brutally honest:

Do you really believe your donor gains something by partnering with you?

Or do you secretly think:

• “They’re just helping me survive”

• “This is really about funding us”

Because if that’s what you believe…

it will leak into everything you say.

The Part No One Wants to Admit

Let’s push a little deeper.

A lot of the awkwardness doesn’t come from asking.

It comes from this pattern:

You focus on the ministry…

until you need money.

Then suddenly—

you turn toward donors.

And they feel it.

Because from their perspective?

They only hear from you when you need something.

That’s where the disconnect happens.

Not because fundraising is wrong—

but because the relationship wasn’t built first.

If You Say It’s Meaningful… You Have to Prove It

You can’t just tell donors:

“This is meaningful. You’re making an impact.”

And then disappear.

If you’re inviting them into something meaningful,

you’re making a promise:

👉 I will show you the impact

👉 I will remind you that you’re part of this

If you don’t follow through,

your message starts to feel empty.

And deep down… you know it.

Which brings the awkwardness right back.

How to Start the Conversation Without Feeling Pushy

This is where everything shifts.

Most people start like this:

“We exist to…”

“We’ve helped this many people…”

“Our mission is…”

That doesn’t work.

Because your donor is thinking:

Why does this matter to me?

Instead, you start with the problem.

The tension.

The thing that’s broken.

Something like:

“Isn’t it heartbreaking that there are kids who will never have access to education… simply because of where they were born?”

Now they’re in it.

Now they care.

Now they’re leaning in.

Because you didn’t start with your ministry.

You started with something they already feel.

This Is the Difference

One approach says:

“Here’s what we do.”

The other says:

“Here’s what’s broken—and why it matters.”

Only one of those invites someone in.

Let’s Bring It Together

If fundraising feels awkward, it’s not random.

It usually comes down to three things:

1. You’re not fully convinced you have something valuable to offer

2. You don’t deeply believe it benefits your donor

3. You’re starting the conversation in a way that doesn’t connect

Fix those…

and everything starts to feel different.

If You’re Ready to Actually Change This

If you’re tired of carrying that weight every time you fundraise…

I want to invite you into something deeper.

Inside my free workshop, Fundraise with Confidence, I’ll walk you through:

• Why fundraising feels icky (and how to break out of it)

• How to reframe asking so it feels aligned—not pushy

• Exactly what to say to start the conversation

👉 Go to irisstorytelling.com/fundraising and save your seat.

This is where that heavy, awkward feeling finally starts to lift.

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