You Already Have A Content Plan. Here’s How To Use It.

This Guide is the first of five to help major gift fundraisers build an online presence that’s clear, sacred, and truly results-driven. You can see the introduction to the series here.

As we begin, here’s a simple truth:

If you’re a major gift fundraiser, you already have a content plan.
It’s actually in your calendar.

Every week, you attend one-on-one meetings, strategy sessions, and board calls.  You follow-up on emails, voice memos, messaging threads - and hopefully take long walks to think through challenges in a donor relationship.

All of these actions are your content plan.

You don’t need a marketing degree or a social media intern.
You just need to pay attention to the questions you’re already being asked - and start answering them.

This is the foundation of the They Ask, You Answer (TAYA) system.

Stay with me.  The system works.

What It Looks Like Day to Day

Let’s say you just wrapped a meeting with a long-time giver. Driving home, you hear their questions echoing:

🙏 “She wasn’t sure how her gift made a difference.”
👀 “He asked again how you measure impact.”
🤔 “They wanted to know what it really costs - not the polished version."

These aren’t just questions - they’re content prompts.

Maybe you’re at an event, and someone in a small group asks, “I’m curious… how do you decide who gets asked for large gifts?”

Or: “What happens if I give, but later want to change where the money goes?”

These are meaningful moments - signs of curiosity and maybe even confusion.

Here’s where the TAYA mindset shift comes in:

Instead of treating those conversations as one-offs, treat them as teachable moments - not only for the person who asked, but for everyone who’s quietly wondering the same thing.

Answer openly. In public. With warmth and clarity.

You might share your answer in:

* A LinkedIn post
* A team-wide Slack message
* Your next board update
* A donor-facing newsletter
* A 90-second video from your phone

The channel is flexible. The posture stays the same: Teach, don’t pitch.

Be helpful. Be clear. Be generous.

But Wait… What Do I Actually Say?

Allow your givers and prospects to guide the way. Below are five categories of questions you’ve probably heard before - over coffee, after a vision trip, or in the middle of a boardroom debate. These questions aren’t random. They fall into what Marcus Sheridan calls “The Big 5” - the five questions people ask before they take action.

For major gift fundraising, here’s “The Big 5”:

1) Cost: “How much does this program cost, and what does my gift ultimately accomplish?”

* If I give $25K, exactly how will it be spent?
* What does it cost to run this program annually
* Are you expecting me to cover a portion of the cost or the entire amount?

🧭 Your job:  Be unmistakably clear.  Get specific. Don’t round up, gloss over, or water it down.

2) Problems: “What’s the most challenging concern?  Where does it fall short?”

* What’s the biggest obstacle you’re facing right now?
* Have you ever received a gift that didn’t result in the intended outcome?
* What obstacle might cause this model to fail?

⚠️ Your job: Tell the truth. Transparency builds credibility.

3) Comparison: “Why should I give to your cause and not elsewhere?”

* How is your cause different from [another nonprofit I support]?
* Why not fund local leaders directly?
* Are there other organizations doing similar work more effectively?

🧠 Your job: Clearly articulate your distinct approach - and do the same when talking about other “competing” causes.

4) Reviews: “What do other givers think - and can I trust you?”

* Who else supports your cause?
* Can I speak with others who’ve been involved in similar projects?
* What’s the most meaningful feedback you’ve received from families like mine?

🗣️ Your job: Let your givers do the talking. Stories carry more weight than stats.

5) Best Fit / Strategic Giving: “What’s the best way for me to make a real difference?”

* What’s the most strategic gift I could make this year?
* If I care most about [specific cause] - what’s the best project to support?
* Should I give now or wait for a bigger campaign?

🎯 Your job: Guide with humility. Help them match passion with timing and impact.

Every one of The Big 5 questions matters - not just for the conversation you’re having, but for your broader audience.

If one giver asks it, ten others are wondering.

Your job is to answer with clarity, humility, and story.

🛠️ Want help turning these questions into action?

Here is a reflection tool I’ve created to help you name the questions givers are asking. Practice answering them and use this tool during your next weekly review or team check-in.
👉 Big 5 Reflection Tool

Don’t Overthink It - Teach What You Know

A few weeks ago, someone asked me, “What happens if a giver changes their mind midstream?” It’s a softball for me, but I know that's not true for many charity leaders.

So, I’ve started drafting a few short posts to answer it directly. Chances are, you might be wondering too, so I’ll share the posts as soon as they’re ready.

Justin Welsh offers a piece of advice that’s really stuck with me: “Think about a topic in which you have expertise and could speak about, unprompted, for more than 15 minutes. That’s the anchor for your content over the next six months.”

For me that anchor is major gift fundraising. It’s also a handful of missional causes I care deeply about - ones Julie and I have supported for years.

For you, it’s the cause you raise money for - among other things.

To build on my “15 minutes of expertise”, I made a giant list of questions I hear major gift fundraisers asking. Every post I’ve written since has grown out of that list and lived experience.

One important note: My posts almost never include a call to action where I'm pushing my online course or coaching.

And yet, they’ve sparked hundreds of direct messages. Thousands have seen my posts and hundreds have shared my pro tips with their own networks. Nearly 2,000 new people have started following me on LinkedIn, and hundreds more have reached out directly through mutual connections.

Once a week, I invite people to subscribe to this guide - which now has 378 subscribers.

A Sacred Task

One of the most sacred postures in fundraising is telling the truth with clarity and inspiration.

When you help people understand how the work of your cause actually functions - how relationships move, how timing works, how impact flows - they trust you.

When they trust you, they listen.  And when they listen, they often give. But even if they don’t? You’ve served them well.

Something to do this week

Grab your calendar and review your last seven meetings.  Ask yourself:
What questions came up?
What felt unclear?
What surprised you?

Write down five of those questions. As you reflect, don’t just search for clever ideas - look for clarity. Where is trust needed? What truth can you offer?

Choose one question and write a three-sentence response.
That’s your post. Share it on LinkedIn.

I'll say it again: If one giver asks about it, ten others are wondering the same thing.

Want to go deeper? Next week we’ll explore the power of showing up weekly to teach and inspire on LinkedIn. (It’s simpler - and more sacred - than you think.)

* * * * * * * * * *

If you haven't taken advantage of some of the resources I've created to help major gift fundraisers, take a look now!  Initial calls with me are free and "no strings attached".  Sometimes folks feel like they need to wait and not 'bother' me until they have a pressing issue.  No need for that...just make the call. 🕺

‍Here's where you can access a lot of content for free:

‍* Follow me on LinkedIn - You'll get short pro-tips and reflections on major gift fundraising every day between 5-7am pacific.

* Breakthru Newsletter - As you've seen here, these are longer weekly posts (audio and written) sent directly to your email.

* Breakthru Blog - the newsletter from the previous week gets posted here each week for everyone (so email subscribers get it a week early).

* Breakthru Podcast - Interviews with high net worth givers about how we as fundraisers can get better at inviting them to the party.  And audio readings of Breakthru Blog posts.

‍Before getting to the PAID stuff: My opinion is that no small ministry with a tight budget should be spending more than $3-5k (total) for major gift coaching/consulting.  Most of you will be good-to-go spending far less than that.  This was a major issue for me when I was a frontline fundraiser - major gift consultants were an expensive 'black-box-of-confusion' for me.  That stops now.

‍Here's the PAID stuff:

‍* Online Catalyst Course - This is a full brain dump of my 28+ years of experience - good, bad, ugly.  It's built around the fundamentals, the sacredness, and the fun, of major gift fundraising.  It's infused with Henri Nouwen reflections.  Many people can take this course and they will be 'cooking-with-gas' and not need any additional coaching from me on the core systems.  I'm grateful that this course has gotten *great* reviews.

* Live coaching with me - I refer to this as "brain rental".  The ROI on live coaching, as you might imagine, is extraordinary.

Finally, be sure to connect with my colleague Ivana Salloum.  She's super awesome and can help with scheduling and access to resources, etc.

I look forward to hearing about your good work!

Blessings,