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Home » Real Estate » News » The Key Question Many Advisors Aren’t Asking
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The Key Question Many Advisors Aren’t Asking

May 9, 20256 Mins Read
The Key Question Many Advisors Aren't Asking
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It’s a missed opportunity hiding in plain sight: “What’s your favorite charity?” It may sound basic, but it’s a question we didn’t ask for far too long— and now, we can’t imagine not asking it.

As financial advisors, we’re trained to gather buckets of critical information: income, assets, liabilities, estate documents, insurance coverage. But in our pursuit of comprehensive planning, many of us have overlooked one of the most revealing and emotionally resonant questions we can ask a client. One that unlocks deeper relationships, uncovers hidden planning opportunities, and often leads to more fulfilling outcomes for clients and advisors alike.

At a time when relationships are everything in wealth management, asking clients about their favorite charity is helping differentiate our practice in ways we never anticipated.

It should be no surprise to our fellow advisors that charitable giving isn’t just a seasonal sentiment, but a growing part of next-generation clients’ financial planning ethos. According to Giving USA, Americans donated over $499 billion to charity in 2022, and while the total dipped slightly from a record-setting pandemic surge, the commitment to philanthropy remains strong, particularly among high-net-worth households.

The 2023 U.S. Trust Study of Philanthropy reported that 90% of high-net-worth individuals give to charity, with nearly half incorporating charitable goals into their estate plans (something we’ve seen firsthand, and I’m sure our peers have noticed this trend too). But given all the data highlighting a conscious effort to support financial gifting, only about 16% of advisors routinely ask about philanthropic goals during discovery or planning processes, per research from the Fidelity Charitable Giving Report.

Related:Art Collector Gets Charitable Deduction Despite No Qualified Appraisal

When we started using FP Alpha to integrate AI-driven insights into our tax and estate planning, it quickly became clear how much our clients’ stories mattered. The software was exceptional at surfacing planning gaps, such as undeclared charitable bequests in wills, unused opportunities for Qualified Charitable Distributions (QCDs), or inefficient giving strategies involving cash instead of appreciated assets.

But it wasn’t until we married the technology and planning insights with actual human conversation that something remarkable happened. Asking our clients about their favorite charity sparked something we didn’t expect: Clients lit up. Some gave quick, matter-of-fact answers. But more than half went deep, sharing touching personal stories: a child’s illness that led to lifelong support for pediatric hospitals, a veteran grandfather whose memory inspired donations to the Wounded Warrior Project and a beloved pet who made the local animal rescue their passion project.

Related:Eight Critical Steps When Considering Art Donations

The question changed everything for us. Suddenly, we weren’t just talking about money—we were talking about legacy, identity, and purpose.

“What’s your favorite charity?” opens the door to discussions that aren’t evident on a client’s tax return. For instance, a client may be tithing thousands annually to a church but not capturing any tax benefit because of the standard deduction. That’s where we step in with solutions like donation “bunching” or donor-advised funds.

In one case, an elementary school teacher donated monthly cash to her church. Through a tax snapshot, we realized she could benefit more by using appreciated stock from her brokerage account, avoiding capital gains and

maximizing her tax efficiency. She loved the idea not just for the tax benefit, but because it meant more resources could go toward the cause she believed in.

We also take the opportunity to remind clients of our shared interest in helping them achieve their charitable goals. It’s easy to incorporate across our organization. For Thanksgiving appreciation cards, we mentioned a client’s favorite charity to which we had donated. This simple act became a catalyst for new business. The card ended up on their fridge, where their adult children saw it. A few months later, one of them became a client.

Related:Daffy Announces New Suite of AI-Powered Tools

It’s what we now call doing well by doing good.

As Registered Investment Advisors (RIAs), we always seek ways to stand out in a sea of sameness. Everyone offers portfolio management. Everyone claims to be “comprehensive.” But how many advisors can point to a moment where they meaningfully changed the trajectory of a client’s financial legacy? Our simple question does that for us.

Talking about a client’s charitable impact has driven tangible results:

· It has increased wallet share from clients who feel more deeply connected to their plan and to us.

· It’s brought us stronger referrals—because these stories get shared over dinner tables and on social media, not just in spreadsheets.

· It allows greater team integration as our next-gen advisor owners can comfortably enter these legacy conversations and earn trust.

Succession planning has been essential for us over the past few years, allowing us to introduce clients to our next ownership team. By handing the reins of tax and charitable planning discussions to our G2 advisors, we’re elevating their role in complex conversations while ensuring clients become comfortable interacting with more than just the founding partner. It’s succession by design, not by default.

But none of this would be possible without the right technology. FP Alpha’s estate and tax planning snapshots play a central role in this effort. The estate snapshot distills dense legal documents into digestible summaries, allowing us to instantly identify if and how charitable bequests are part of a plan and recommend adjustments accordingly.

Leveraging a tool with a tax snapshot is a great idea. It visually breaks down itemized deductions, revealing opportunities for optimization. Are they missing deductions? Are they taking the standard deduction but giving significant amounts to charity anyway? These insights guide our planning and fuel more strategic discussions.

Here’s how we now frame the conversation with clients:

“We’ve recently added a new tool to uncover tax and estate planning opportunities using your existing documents. As part of that process, we’ve started asking one new question that helps us understand what matters to you: What’s your favorite charity?”

It’s noninvasive, personal and allows clients to share their values, not just their numbers.

And when they do? That’s where the magic happens.

The Bottom Line

We’re not saying charitable giving is the only lens through which to serve clients, but it’s one of the most underutilized. And in an industry where relationships drive retention, referrals, and revenue, we can’t afford to miss the chance to connect on what matters most.

If you’re an advisor looking to stand out, to go deeper and build a business that’s as meaningful as it is profitable. Start asking better questions.

Start with: “What’s your favorite charity?”

You might find it’s the most valuable conversation you’ve ever had.

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