🤫Shhhh… Don’t Tell Anyone

As I was filling out an inquiry form this past week, one of the questions asked me to describe my professional role as a major gifts consultant.  The following question caught me a bit off guard: What’s one thing people would be surprised to hear about you related to your work?

I paused, not because something didn’t immediately come to mind. It did, although I was a bit hesitant to expose my inner truth.

My response may surprise you: I hate asking people for money.

Let me be quick to add that I absolutely love inviting people to the party. There’s a big difference which we’ll unpack in this issue of The Weekly Breakthru Guide.

Let’s begin with a story…
I was sitting in the living room of Dave and Laney, two of the most generous souls I am privileged to know. We have journeyed together for years - enjoying lots of coffee, conversations, and shared stories. On this particular evening, I was preparing to invite them to do something bold: increase their annual gift from $25,000 to $200,000!

What was driving my confidence to swing big?

A wealth database showed me they had capacity.

I made the ask. Dave smiled, paused, and asked: “Hey… did you search for us on one of those wealth websites?” I quickly confessed that I had.

After handing over the report to Dave, he leaned back, thoughtful (and a bit bemused). “This is about 50% right,” he said. “But in the future, why don’t you just ask us directly? Talk to us.”

It was a grace filled moment for me. They weren’t offended, but they also weren’t ready to say yes. I learned something crucial that evening, still important to this day:  Financial capacity doesn’t equal relational readiness.

Throughout my career, the ask was planned primarily around financial capacity, and more often than not, without any input from the prospective giver. It was an unfortunate guessing game and one I increasingly dreaded. Misreading financial capacity is one of the biggest reasons so many frontline fundraisers burn out after just a few years in this work.

So when do you know it is time to invite?

Think for a moment about throwing a party. Let’s say you love American football so you plan to throw a big party on Super Bowl Sunday with all the food, drinks, big screen, comfortable chairs, banners, etc. It’s going to be great.

Then you begin making a list of friends you plan to invite. In doing so, you quickly eliminate some names from the list. Jeff - one of your best friends from university - hates football. It would be a tad tone deaf to invite him. Your friend Patricia doesn’t hate it, but she’s a budding pastry chef and would probably love testing out her latest creations on a bunch of rowdy pigskin fans. You make a note to talk with her about it. And so goes the list-making exercise.

In the end, you have 19 people who would love the invite... 8 you're unsure about... and 12 you'd probably never invite (they would rather run a marathon in jeans and crocs than come to a Super Bowl party).

Let’s say you send invites to 27 of them. All of them will appreciate it. Some may say “no, not my vibe”. Some will have calendar conflicts or other family commitments… Some had already been invited to a different fabulous Super Bowl party.

In the end, you had fun planning for it and extending the invitations. The party turned out to be fantastic (Patricia’s Chili-Stuffed Doughnuts got some nervous side glances but the Buffalo Chicken Éclairs were a huge hit!!! Chef’s kiss🧑‍🍳).

Now, I know it’s not possible to completely conflate the goodwill and frivolity of inviting someone to a party with asking them to give to your cause. So, I have created something that brings clarity and confidence before you extend an invitation to give. It’s called the Strength of Relationship Assessment, or SToR.

SToR is a one-page tool with five simple questions that help you assess relationships over wealth management searches. SToR is a short, human-centered tool that I and my clients now use every time we prepare for a major invitation.

Here’s a breakdown of the SToR questions. They seem simple - yet will tell a deeper story:

1. Do I know both spouses, and have I spoken to them?
Giving is rarely a solo act. If one spouse is missing from the conversation, or if I’ve never actually spoken to them, we don’t have a strong relationship. Yet.

And, actually, I would hope to build trust with the whole household - not just the person who responds to my emails. So the bonus question is this: Do you know other extended family members?

2. Do I know key milestones in their lives?
Milestones - past or upcoming - open a window into someone’s world. A job change, the birth of a grandchild, a cancer diagnosis, a sabbatical… these aren’t side notes. They shape someone’s capacity for connection. And giving.

If I don’t know what season of life they’re in, I don’t yet know if the time is right.

3. Do they have a specific passion tied to our mission?
It’s one thing to be interested. It’s another to be moved.

A strong relationship reveals alignment - when their heart lights up over the same thing we’re doing. That’s when a gift becomes more than a transaction. It becomes an expression of who they are.

4. Have we talked about their giving in the last six months?
If it’s been a while, things might have shifted. Their priorities, values, or energy might be moving in a new direction.

Givers are on a journey. Talking about giving regularly (not just when it’s time to ask) keeps you close to where they actually are.

5. Do I know what brings them joy in giving?
This is the gold standard. When you know what brings someone joy - when giving feels like freedom, not obligation - you’re on sacred ground.

And you don’t get there by asking for more. You get there by being curious, listening well, and tending the relationship over time.

What I learned from Dave and Laney

As it turned out, their capacity wasn’t what I thought. And my ask - while not offensive - was premature.

So what saved that moment? The Strength of Relationship.

Because we had taken time to build real rapport…
Because I knew pieces of their story…
And, because they trusted me… they didn’t walk away.

They leaned in.

A year later, they doubled their annual gift to $50,000. A *little* below my ask😅, but nonetheless a great increase to celebrate.

The SToR questions won’t give you a yes/no answer.  However, if you’re getting a 4 or 5 out of 5 on ‘yes’ answers, you’re likely in a strong position to invite them to the party.

Sometimes, the wisest thing to do is hit the pause button on the invite and let the relationship lead. If giving is the party… your job is to make sure they feel like a guest of honor.

Who’s on your list right now… and are they ready to be invited?

* * * * * * * * * *

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,