The Answer Is in a Room You’re Not In Yet

Never ask for a major gift, unless you know the name of your donor’s dog.

It’s a mantra I’ve held since it was uttered, in passing, by my fundraising mentor nearly 15 years ago, and I’ve done my best to mention it in every talk, training, interview or coaching session since.

But what if you knew your donor’s favorite go-to-karaoke song?

Or what if you knew the unique backstory of how your donor’s ended up in a rural town in flyover country after living in Chicago for three decades because they wanted a quieter life?

Or what if you knew your donor’s were really good at doing puzzles…while consuming pizza and beer in which the fastest humans who can complete puzzles, pizza and beer would get prizes and now your have hyper-personalized knowledge that they have several trophies for being the fastest consumers of beer and pizza whilst finishing a 300 pieces puzzle?

Dare I say, these are the things that absolutely put you at an advantage over any other solicitor for gifts in the community…because you’re more interested in what your donor loves, likes and is obsessed about, rather than the size of their checkbook.

And in order to find that information out, you’re going to need to get out from behind your desk/computer screen and show up.

You need to be in the room.

I just got back from the Mid America Chamber Executive’s Conference (MACE).

And despite knowing I will be horrifically behind on emails during this trip to the “other Dakota,” it’s my favorite conference of the year. It’s my favorite event to sponsor. And it has some of my favorite humans who attend.

I spoke twice.

Both went great.

Oh, and on side note – the key to getting a standing ovation from the stage is to announce to a room of Chamber leaders that you’re the sponsor who purchased the happy hour keg.

Instant dopamine rush for all parties. LOL.

Presenting is fun.

People laughing at dad jokes is fun.

Telling a room full of nonprofit and chamber leaders that they’re capable of more than they think they are? That never gets old.

But:

The talks & presentations weren’t the most valuable part of the trip.

Not even close.

The most valuable part was the hallway.

It was the cocktail at a local bar with Chamber leaders talking about the impact of their nonprofits.

It was the conversation over mediocre conference coffee about membership models and why people take a risk to join something.

It was the impromptu 20-minute chat with an ED who pulled me aside to brainstorm a new event.

That conversation didn’t happen because of a webinar. It didn’t happen because of a social post. It didn’t happen because of a well curated and edited email sequence or a landing page or a really well-designed Canva graphic.

It happened because I was in the room.

Think about it.

The common thread that we all have as fundraisers is frustration with our board. Or being a solo-shop (or damn well near it) who wears 10,000 hats. Or having a tired annual appeal copy-pasted since 2019. Or ED’s shuddering at the idea of making asks.

And the solution to any one of those PTSD-induced moments is not a better template. It’s not a smarter system. It’s not a new CRM or a fancier email platform.

It’s being in the room with humans.

The board member who’s disengaged? That changes when you take them to coffee and actually ask what they care about.

The donor who stopped giving? That changes when you pick up the phone and say thank you like a real person.

The ED who’s scared to ask for money? That changes when they sit across from someone, human to human, and realize that “the ask” is just a conversation.

Every. Single. Fix. Starts with a human being in a room with another human being.

And I know - I KNOW - that sounds almost offensively simple in 2026. We’ve got AI tools and automation platforms and digital marketing funnels that can do miraculous things.

I teach that stuff. I love that stuff.

But none of them replace the hallway.

Your donors give because someone from your organization looked them in the eye, connected with them as a human, and invited them to be part of something real.

Your community partners link up with your organization because you toured their office and met with their staff and volunteers and sparks of connection flew.

Your cheerleaders feel your enthusiasm over lunch as you told them the best impact story of the last month.

Yes, this goes back to my obsessive theme in 2026…embrace analog relationship building.

The Hallway Is Where the Real Work Happens

Let me tell you what happened at MACE that no slide deck could have produced.

I sat at a bar with a group of Chamber leaders and we talked about membership. Not in the “best practices and benchmarking” way. In the real way.

The “how do you convince someone to take a risk on joining something when they don’t know what they’re going to get?” way.

And you know what? That conversation is IDENTICAL to the donor conversation.

A member who joins a Chamber is taking a risk. They’re saying, “I believe this is going to be worth it, even though I don’t have proof yet.”

A donor who writes a check is doing the exact same thing. They’re saying, “I believe in this mission enough to invest in it before I see the outcome.”

Both of those decisions are built on trust.

And trust is not built through email campaigns.

It’s not built on highly edited social media posts.

Trust is built in rooms, over time, through consistency.

Over coffee.

Over cocktails.

Over the questionable conference lunch that everyone quietly complains about but somehow eats every bite of anyway.

The question isn’t whether your donors and members and board members want to be connected. They do. They showed up. They raised their hand.

The question is: are you showing up for them the way they showed up for you?

Not once a year at a big event. Not when you need something. Consistently. Relentlessly.

Like someone who’s been doing this long enough to know that the relationship IS the strategy.

So What Do You Actually Do About It?

Here are three things you can do this week to stop hiding behind the screen and start getting in the room.

1.    Make One Phone Call You’ve Been Avoiding

You know the one. There’s a donor you’ve been meaning to call. A board member you’ve been meaning to check in with. A community leader you met at an event three months ago and said “let’s grab coffee” and then never followed up.

Today. Call them today.

Not an email. Not a text. A phone call. With your voice. Where they can hear that you’re a human and not an AI agent.

Oh, and the call doesn’t have to be about anything. In fact, it’s better if it isn’t.

“Hey, I was just thinking about you and wanted to check in. How are things?” That’s it.

That’s the whole script.

You know what happens when you call someone for no reason? They remember you. They trust you more.

And the NEXT time you do have a reason to call - an invitation, an update, an ask - it doesn’t feel transactional. It feels like a friend reaching out.

That’s fundraising.

One call. Today. Stop reading this and go do it. (OK fine, finish the blog first. Then call.)

2.    Get in ONE Room This Month That Isn’t Your Office

A conference. A networking lunch. A Chamber meeting. A Rotary event. A nonprofit coalition gathering. A community foundation mixer. Your local coffee shop where you intentionally invite a colleague to sit with you for 45 minutes.

It doesn’t have to be fancy.

It doesn’t have to be expensive.

It doesn’t have to be a curated experience with a theme and a keynote and a merch table.

It just has to be a room with other humans who care about community impact.

Because here’s what I re-learned at MACE - and what I’ve been re-learning for nearly 20 years in this work: you cannot predict which conversation will change everything. 

The most valuable connections I have ever made weren’t in a session or on the agenda.

It was at a bar, unplanned, talking about something I didn’t expect to talk about.

That only happens when you’re in the room. You can’t stumble into a hallway conversation from your desk.

Look at your calendar right now. Where’s your next room? If there isn’t one, find one. This month. Put it on the calendar before you close this tab.

3.    Treat Every Interaction Like a Hallway Conversation

OK, I hear you. “Patrick, I can’t fly to every conference. I’m a solo shop with 10,000 hats, remember? You literally wrote a blog about me.”

Totally fair. I see you. I feel that. But also:

The hallway mindset isn’t about geography. It’s about approach.

You can bring hallway energy to a Zoom call. You can bring hallway energy to a phone conversation. You can bring hallway energy to a donor meeting in your own conference room.

So, what does hallway energy look like?

No agenda. Just curiosity. “What’s going on in your world?”

No pitch. Just presence. “I’m glad we’re talking.”

No script. Just honesty. “Here’s what we’re working on and here’s why it matters.”

The best fundraising conversations I’ve ever had - the ones that led to major gifts, to board commitments, to long-term partnerships - none of them started with a formal presentation. They started with two people being real with each other.

You can do that anywhere. You just have to decide to do it.

We are living in the most digitally connected, relationally disconnected era in nonprofit history.

We can automate our thank-yous, schedule our social posts, generate our grant narratives with AI, and run our entire fundraising operation from a laptop on the couch.

And a lot of that is genuinely useful. I teach it. I believe in it.

But somewhere along the way, we started confusing efficiency with connection. 

And they are not the same thing.

Your donors are not email addresses.

Your board members are not agenda items.

Your community leaders are not LinkedIn connections.

They are people who said yes to your mission and are waiting - genuinely waiting - for you to show up as a human being and meet them where they are.

And your do-gooders - the real ones in the trenches every day navigating “other duties as assigned” and fighting for their communities, need someone who’s been where they are, who’s done the work, and who’s going to stick around long after the event is over.

The conference, the tools, the templates and trainings? Those give you the playbook.

They teach you WHAT to do. But the hallway - the coffee meeting, the phone call, the bar after the conference, the room you almost didn’t walk into - that’s WHERE you run the plays.

You need both.

But if you only have one, pick the room.

Every time.

Ok, Your Turn!

I want to hear from you. Hit reply, send me a DM, flag me down in a hallway somewhere - I don’t care. Tell me:

What’s the most valuable conversation you’ve ever had at a conference, event, or meeting that WASN’T on the agenda? What happened because you were in the room?

Maybe a hallway conversation led to your biggest donor. Maybe a bar chat turned into a partnership. Maybe showing up to something you almost skipped changed the trajectory of your organization. Tell me that story.

Or maybe you’re reading this and realizing you haven’t been in a room in months. That’s OK. Now you know what to do about it.

Send me your answer: patrick@dogoodbetterconsulting.com or just reply with INFO if you want to talk about getting out from behind the screen and into the rooms that actually move your mission forward.

And one more thing: we’re building something for the moments when you can’t be in the room. A place where the playbooks, the training, the community, and the hallway energy come to you - on your schedule, at your pace. Do Good YOUniversity is getting a full overhaul, and we’re opening early access soon. If you want to be first on the list, reply with EARLY ACCESS and I’ll make sure you’re in before anyone else.

Together, we’ve freaking got this!

-Patrick

P.S. This is a continuing series around MAYDAY Distress Signals - real problems I hear from nonprofit pros every single week. The distress signals aren’t going anywhere. But neither is the help. More coming soon!!