February 2026 Professional Advisor News

Lost checks. Stolen checks. Delayed checks. And now, effective December 24, 2025, the U.S. Postal Service has changed how it defines the official postmark date, which could impact the timing of when checks mailed to nonprofits “count” for IRS charitable deduction purposes. All of this adds up to an important opportunity to remind clients about the benefits of giving to their favorite charities in ways other than writing a check.

In the nonprofit world, challenges with checks are nothing new, but it’s been a tough nut to crack. Despite the rise of digital tools, many donors still default to writing checks. While checks feel simple and familiar, they introduce real friction for both donors and nonprofit organizations, including not only mailing delays, but also processing costs, security risks, and administrative inefficiencies.

Here are three ways your clients can move away from writing checks to support favorite charitable causes:

Give online
If your client prefers to give directly to favorite charities, remind the client that giving online is faster and more reliable than writing a check, ensuring that a donation is received and credited immediately without the delays, loss risks, or processing uncertainties that come with mail. Online gifts also create a clear digital record with automatic receipts, making it easier for clients (and you!) to substantiate charitable contributions for tax purposes. For nonprofit organizations, online giving reduces administrative costs and allows staff to focus more resources on mission-driven work rather than manual check processing.

Give appreciated stock
Another area where advisors can add significant value is by reminding clients to look beyond cash when making charitable gifts. For example, many clients hold highly appreciated stock, yet they continue to write checks to charitable organizations out of habit. Donating appreciated securities directly to a donor-advised fund or other qualified charitable organization can be far more tax-efficient. When structured properly, the client may be able to avoid capital gains tax on the appreciation while still receiving a charitable deduction for the fair market value of the asset. This often results in a larger gift to the nonprofit organization at a lower after-tax cost to the donor, a result that aligns perfectly with both philanthropic and financial planning goals.

Use a donor-advised fund
Suggest that your client organize charitable giving through a donor-advised fund at GiveWell Community Foundation. This offers a more streamlined and intentional alternative to writing checks. A donor-advised fund allows a client to consolidate philanthropy in one place, make a single contribution (or a series of contributions), and then recommend grants to charities over time. This approach reduces paperwork, simplifies recordkeeping, and creates a clear structure for giving that can evolve with the client’s priorities.

By gently reminding clients about alternatives to check-writing, you are helping them make the most of their giving. As always, the Community Foundation is here to assist you as you advise your philanthropic clients. We are here for you!

Most clients rely on a team of professionals to guide them through tax, legal, and financial decisions. Even when everyone is competent and well-intentioned, it can be surprisingly difficult to keep conversations aligned across disciplines. Clients may hear excellent advice in separate meetings yet still feel as though the plan is fragmented. One professional focuses on documents, another on projections, another on portfolios. Unless professionals proactively strive to work together, the client is left to connect the dots with little technical expertise.

Lack of coordination can have real consequences. For instance, recent Tax Court decisions underscore why charitable giving is an area where attorneys, CPAs, and financial advisors not only must operate as a coordinated team rather than in parallel silos but also should consider involving GiveWell Community Foundation to provide input during these discussions.

In both Cade v. Commissioner and Besaw v. Commissioner, the taxpayers’ charitable intent was clear, yet the deductions failed because critical substantiation and valuation steps were missing or incomplete. These cases highlight a common challenge that can contribute to situations faced by the taxpayers in each case: each advisor may reasonably assume that someone else on the team is handling valuation, acknowledgments, and Form 8283 compliance. Attorneys may focus on structuring the gift and legal compliance, financial advisors on asset selection and timing, and CPAs on reporting the deduction, but when documentation responsibilities are not explicitly assigned, essential evidence such as qualified appraisals, properly completed forms, and contemporaneous written acknowledgments can fall through the cracks. The result likely is not simply the IRS’s technical adjustment, but instead the complete loss of the charitable deduction.

This is where intentional collaboration, including working with the Community Foundation, becomes especially important. We can serve as a convener for all advisors to structure a charitable giving plan that meets a client’s goals. What’s more, the Community Foundation keeps an eye on legal and policy developments and is able communicate with attorneys, CPAs, and financial advisors to determine which developments might impact their clients and what to do about it. Furthermore, to best achieve a client’s goals, charitable planning ought to be an ongoing process, not just a year-end activity.

The Community Foundation is honored to be your go to when you are helping your clients set their charitable intentions in motion. It is our pleasure to support your efforts.

As an attorney, CPA, or financial advisor, you are no stranger to witnessing the ripple effects of life’s unexpected curveballs. If you represent a client over many years, you’re very likely at some point to help the client through a serious illness, a loved one’s death, business challenges, marital dissolution, strained relationships with children, or all of the above.

Research and survey results tell us that many clients’ most consequential estate and financial planning activities arise not from long-term intentions, but from sudden change. Moments like this are challenging because clients are often overwhelmed and unsure how to proceed, and even the best advice can feel like too much information delivered too soon. In these situations, be aware that charitable planning can help re-anchor clients’ decision-making in values rather than fear or urgency. For many clients, generosity is one of the few topics that still feels familiar when everything else is shifting.

Here are three examples:

Change in assets
Following a divorce settlement, a client may suddenly be holding cash, concentrated stock, or other highly appreciated assets. The client may also be juggling other priorities: adjusting lifestyle expectations, supporting adult children, and rethinking an estate plan. When the client also wants to do something charitable but isn’t sure yet what organizations to support, establishing a donor-advised fund at the Community Foundation can be a natural fit in some cases, allowing the client to be eligible for a tax deduction when the contribution is made while taking time to decide which charities to support and when.

Loss of spouse 
A client whose spouse has recently passed away may want to make a charitable gift in the spouse’s memory but likes the idea that the gift could benefit the community or beloved local charitable organization for many generations and address urgent needs that arise decades from now. Establishing a memorial fund at the Community Foundation allows a client to create a loving legacy in their beloved’s honor and support a favorite charitable organization or evolving community needs over time.

Retirement
A 74-year-old client who just retired is feeling less “relevant” outside of the workforce and therefore would like to do something meaningful for the community. With plenty of assets in retirement accounts, the client does not need to rely on distributions from IRAs to maintain lifestyle standards. This client could be a good candidate to establish a designated fund (to support a specific nonprofit organization) or a field-of-interest fund (to support an area of need such as education, health care, or the arts) at the Community Foundation. Then, the client may direct Qualified Charitable Distributions from IRAs (up to $111,000 per taxpayer in 2026) to the fund, bypassing adjusted gross income and counting toward required minimum distributions.

The Community Foundation is happy to help. Next time you are meeting with a client who is experiencing one of life’s inevitable rough patches, remember that charitable planning allows your client to take action that brings joy, reflects identity, aligns with purpose, and helps the client shift from a reactive mode to an intentional one.