Gala Planning Mistakes: What Two Charity Auctioneers Want You to Fix First

Two Auctioneers, One Answer

Chris Hensley and Brett Higgins have called hundreds of galas between them, and when Hey Nonprofits pulled the top questions from a Chicago panel discussion the two shared, their answers on the biggest pre-event mistake converged almost immediately — even though neither had compared notes beforehand. Hensley's answer started with a single word. "Data. I mean, I could just end right there," he said. "Most organizations behave as though the event has never happened before, right? And yet it has, and they have data that will help the next one be even more successful."

His prescription is concrete: block off an afternoon, however far out the next event sits — Hensley was coaching a February 2027 client eight months in advance — and dig into whatever platform the organization uses. "Who attended your event? Who hosted your tables? Who gave the most money? What table produced the most money? What was the mean and the median in giving?" The goal isn't just historical curiosity. It's identifying the donors who gave the most last time and getting them locked back into the room before it sells out. "Make sure that before your room sells out, the tables that produce above the 50% point of your attendees from last year are back in the room."

Don't Let a "No" End the Relationship

When a top donor can't attend, Hensley doesn't treat that as a lost gift — he treats it as a different kind of ask. "Would you consider doing that again even though you can't be with us? We'll acknowledge it in the room," he tells past supporters, with their permission. On stage, that becomes a moment of recognition rather than an empty seat: "Folks, Trevor Nelson couldn't be with us here tonight, but he supports this cause, and I assure you, if you raise your paddle at $10,000, you are not alone, because Trevor Nelson, even though he's not here, is in with us at $10,000."

Higgins pointed out that some supporters genuinely prefer not to attend at all — "they don't want to go have a chicken dinner," as he put it — but that doesn't mean they're unreachable. He and Hensley always confirm with the donor first whether they're comfortable being acknowledged publicly, since some prefer to give anonymously. But the underlying instinct, Hensley argued, should always be to ask rather than assume. "If you don't ask for that gift, you guarantee the answer."

Mini takeaway: A donor who can't attend isn't a lost gift. Call them anyway, offer to acknowledge them in absentia, and let them decide.

Six Months Planning a Dinner vs. Six Months Planning a Fundraiser

Higgins framed the single biggest structural mistake he sees in blunt terms: "A lot of organizations spend six months planning a dinner instead of six months planning a fundraising experience." Centerpieces, menus, and linens matter for guest experience, he said, "but those things inherently do not raise money." The organizations that consistently outperform their peers spend that same six months a different way — preparing their board, identifying major donors, securing meaningful auction packages, building compelling stories, and coaching speakers. "By the time guests walk through the doors, if they've done their job, the fundraising shouldn't be beginning. That would simply be reaching its climax."

Mini takeaway: If your fundraising conversation starts the night of the event, you're already six months behind.

"We Don't Want to Ask for Too Much" Is a Message Problem, Not a Money Problem

Both auctioneers hear a version of this objection from board members constantly: we don't want to push our donors too hard. Higgins's response reframes the ask entirely. "You're not asking people to give because your organization needs money. When you make it about money, then people are less inclined to give. You're giving people the opportunity to become part of something meaningful." Nobody attends a gala surprised that they'll be asked to give, he noted — what turns people off isn't the ask itself, it's feeling sold to. "If every ask is authentic, if it has purpose, if it shows impact, then I don't think most donors feel bothered."

Hensley connected the hesitation to a past bad experience rather than a present risk. "It's a response to having been made to feel icky in the fundraising moment at their event at some point in the past." His counter-argument doesn't pull punches: "If you don't want to raise too much money, then you also don't want to do too much mission." Nonprofits exist to fix something, and the fix is funded by the money raised. Reluctance to ask isn't caution — it's a ceiling put on the mission itself.

Pressure Isn't the Enemy — Manipulation Is

Higgins drew a sharp line between two things that get conflated constantly in gala fundraising: pressure and inspiration. "Pressure says you should give, in that tone. Inspiration says now you understand why giving actually matters." People don't respond well to feeling manipulated, but that doesn't mean every form of social dynamic is off-limits — some donors are genuinely motivated by a bit of competitive energy. "There is some peer pressure that is imperative for fundraising in some ways," he said. The skill is reading the room and applying the right lever to the right person, rather than treating every guest identically.

Hensley calls his version of this "unspoken peer pressure," and it's produced some of his biggest single-night results. At one event with a thousand guests and a $400,000 goal, he pushed past the comfortable stopping point after two big early gifts and ended the night at $1.2 million — triple the target. His tactic is visual as much as verbal: put a donor's name on the screen when they give, hand board members and leadership a different color paddle so the room can see who's leading, and call out generosity by name from the stage. "217 at $2,500 — Brett Higgins, thank you so much for your generosity," he offered as an example. "Brett is an influential person to other people in the room. So he's motivating unspoken peer pressure — those people to raise their paddles as well."

The same principle showed up in a story Hensley told about a donor named Bob, who raised his $250 paddle nine separate times over the course of one paddle raise after Hensley publicly encouraged the room to "be like Bob." Roughly 37 other guests followed his lead. "The room was just having a rip-roaring good time doing it," Hensley said. "I'm going to choose celebration every time. Your mission is going to sell itself. You don't need to jam it down their throats, but you do need to make them feel good about giving."

Mini takeaway: Visible generosity is contagious. Put donor names on screen, hand your board a different-colored paddle, and let the room see who's leading.

Don't Put an Auctioneer on Stage After 9:15

Hensley pointed to program pacing as the most common technical mistake: fundraising gets pushed to the end of the night, after long speeches have already drained the room's attention. "If you ask 20 auctioneers what the witching hour is, it's like 9 or 9:15," he said. "If you put an auctioneer on stage after 9 or 9:15, maybe you get a tiny bit of a blessing on a Saturday night, but on any other night — 9:15 and people are gone."

The other pacing trap involves guest speakers, particularly elected officials, who treat their stage time as a platform rather than a supporting role. "The speaker is there to serve the good of the organization, not to be heard," Hensley said, describing an event where a politician spoke so long "the event was over six months later" in his telling of it, and the room had mentally checked out well before the ask. His advice: give any speaker, however prominent, a strict time limit — three minutes is reasonable — and ask to review their remarks in advance. "It adds credibility to your event to have the governor or the attorney general or a U.S. senator, but ask them to speak for three minutes, and don't think you're offending them when you ask to see their comments in advance. That keeps them to their comments."

Aesthetics Get the Budget; Engagement Gets the Revenue

Asked what nonprofits overinvest in relative to its actual fundraising impact, Higgins didn't hesitate: room aesthetics. "Everyone wants the room to look beautiful, and it should. But people had 364 other dinners that year, and by next year they will have had another 364 in between." What actually drives revenue, in his view, is almost entirely about emotional engagement rather than production value: "Do your guests feel connected? Do they know why they're there? Have they heard a story that moved them? Is your board participating? Is your leadership setting the example? Revenue follows emotion more often than decoration."

Hensley's version of the same point came from a client's data, not a general theory — proof that the right answer isn't identical for every organization. One client's live auction raised just over $90,000 while its silent auction pulled in $145,000, an unusually large gap in the silent auction's favor. Rather than defaulting to conventional advice, Hensley read what the numbers were actually saying: that particular donor base was more engaged by browsing and bidding than by the theater of a live auction. His recommendation was to lean further into what was already working — expanding the silent auction's "vacation station" concept with more travel packages — rather than trying to force a different format onto a crowd that had already shown its preference. "It's not the same answer for everybody," he said. "It's rooted in data."

Treat Your Gala Like a Real Revenue Stream, Not a Side Project

Closing on advice for any nonprofit leader heading into their next event, Higgins offered a reframe that applies well beyond gala season. Having previously run a major gift program that raised $150 million a year for a hospital system, he admitted events were rarely top of mind for him at the time — "events, you know, were doing five or ten percent of that." But looking back, he realized where his organization's largest donors had actually started. "Where did they start? A lot of them started with events. If you get the 30- and 40- and 50-year-olds into your event today and you steward them like they want to be stewarded, you have the ability to turn a lot of them into your largest donors in the future."

His closing advice ties directly back to where the conversation started: the work that actually determines a gala's success happens long before the room fills up. "Start thinking now about how we can compel people to give, and what can I put in place to accomplish that," Higgins said, "realizing that the gala may become the crescendo of that, but a lot of that starts six months or more in advance."

Insights in this article are drawn from the Hey Nonprofits! podcast episode “What Two Auctioneers Wish Every Nonprofit Knew Before Their Gala”, featuring professional auctioneers Chris Hensley and Brett Higgins.