Giving Season financial professional playbook

A business owner or investor is considering or preparing for a sale, recapitalization, merger, or other liquidity event before year-end. It could result in a meaningful influx of wealth and a larger tax bill, but charitable giving may not be part of the conversation yet.

Before the transaction progresses, allows for flexible planning.

A pending deal can create an opportunity to discuss how charitable giving fits into the client’s broader wealth plan before transaction decisions are finalized. Contributing an eligible business interest before a transaction is sufficiently advanced may reduce or eliminate the capital gain recognized on the contributed interest, depending on the facts and applicable tax rules. A DAF can help by allowing clients to contribute charitable assets before a sale and recommend grants over time.

Confirm where the deal stands 
The stage of the deal usually determines how much flexibility is left for donating the business interest. Earlier conversations tend to give you more options than later ones.

Clarify what your client wants their wealth to do next and their liquidity needs 
Use the liquidity event as a prompt to revisit their broader wealth goals, including any charitable priorities that may not have come up yet. Also, clarify what your client needs from the sale to support their personal, family, and business goals.

Coordinate with the broader advisory team 
Engage tax, legal, and transaction advisors early, since the timing and structure of charitable gifts can affect the tax treatment of the capital gains and the availability of charitable deductions.

A client is considering a Roth IRA conversion, or expects significantly higher taxable income due to a bonus, investment gains, deferred compensation, a liquidity event, or another income event. They also have charitable intentions, and a gift could potentially help offset a portion of that increased income through a charitable deduction.

As soon as it becomes clear that 2026 will be a higher-income year than usual.

A higher-income year can create an opportunity to evaluate charitable giving alongside broader tax planning. Rather than treating charitable gifts as a separate year-end decision, clients and their tax advisors can consider how giving fits within their overall tax strategy. A DAF can help by allowing clients to contribute during the high-income year and recommend grants to charity over time.

Identify clients experiencing a higher-income year 
Look for clients considering a Roth conversion or anticipating higher taxable income from bonuses, investment gains, deferred compensation, business sales, or other liquidity events.

Understand the broader tax impact  
Review how the Roth conversion or higher income affects your client’s overall tax situation, including income thresholds, phaseouts, deduction opportunities, and other planning considerations.  

Evaluate charitable giving within the year’s planning  
Review planned charitable gifts, available assets, and estimated tax liability to determine whether charitable giving should be incorporated into the year’s strategy. For clients who give regularly, this may also be an opportunity to consider bunching multiple years of planned giving into the conversion or high-income year (see play #5 below).

Take a multi-year view
Use the Roth conversion or higher-income year as a prompt to discuss how charitable giving fits into their longer-term financial and philanthropic plans, not just the current year’s tax picture.

• Reduce taxes on a Roth IRA conversion with charitable giving 

A client has recently come into significant wealth through an IPO, vesting event, employee stock purchase plan (ESPP), or other equity compensation. They’re now deciding whether to hold, diversify, sell, or use a portion of those shares to support charitable goals.

As restrictions lift and shares become available, before a client decides whether to hold, diversify, or sell.

New wealth often changes how clients think about their financial future and the impact they want to create. Some may be ready to sell and move into cash. Others may take a more measured approach, balancing diversification, taxes, family priorities, and giving. Raising charitable goals before shares are sold may preserve options, including contributing eligible appreciated shares directly to a DAF.

Open the conversation before a sale happens 
Bring up charitable goals before shares are sold, not after. Many clients assume giving only happens with cash after a sale, but earlier conversations can unlock more flexibility, including donating appreciated shares directly to a DAF.

Identify the equity type 
Identify the type of equity compensation involved, such as restricted stock units (RSUs), stock options, founder shares, or ESPP shares. Each can carry different tax and charitable planning implications.

Assess tax timing and gains 
Review the gains in the shares and how they fit into the client’s broader financial picture. Factor in how long the shares have been held, since recently acquired shares may not qualify for the same charitable deduction as shares held for more than one year. 

A client gives regularly but makes most charitable decisions one year at a time. Their annual gifts may not be large enough to exceed the standard deduction each year, which can limit the immediate tax benefit of charitable giving. They may also have something like a business sale, equity compensation, or highly appreciated assets on the horizon.

Anytime, but especially if 2026 is a year with higher income, a liquidity event, or an appreciated asset sale—events that can lead to higher taxes.

For some clients, it may make sense to bunch multiple years of charitable contributions into a single tax year. This approach may increase total itemized deductions above the standard deduction in the contribution year, depending on the client’s circumstances. As charitable deduction limitations continue to evolve, bunching may become more valuable for some donors. A DAF can support this strategy by allowing clients to contribute several years' worth of giving at once and recommend grants to charities over time.

Identify clients who may benefit from bunching 
Look for charitably inclined clients who regularly take, or expect to take, the standard deduction and may benefit from a multi-year charitable planning strategy.

Evaluate bunching opportunities 
Consider whether combining multiple years of giving into one year could create more flexibility, especially in a high-income year, around a liquidity event, or alongside the sale of an appreciated asset.

Separate contribution timing from grant timing 
Explore separating the timing of contributions from the timing of grants. A DAF can help create that flexibility.

Look ahead for upcoming wealth and tax events 
Keep an eye out for business sales, concentrated stock positions, equity compensation, or other liquidity events, and bring them into the conversation before decisions are urgent.

Align giving with capital gains decisions 
When clients are considering selling appreciated assets, raise charitable intent early so giving strategies can be coordinated with tax and timing decisions.

Bring in the family early and connect giving to long-term goals 
Use a multi-year approach as an entry point for involving family members in conversations about values, priorities, and long-term impact. Tie annual giving decisions back to broader philanthropic goals so giving feels more intentional and consistent over time.