Giving Season donor playbook

A business sale or other liquidity event may be approaching, creating an opportunity to consider how charitable giving fits into your broader plans.

Before a transaction is underway, while your options are still open.

When a business sale or liquidity event is on the horizon, timing matters. Some charitable planning strategies must be explored before the transaction moves forward, as options may become more limited once the deal is underway. Bringing charitable goals into the conversation early can help integrate giving into your broader wealth plan. A DAF may allow you to contribute eligible assets before or instead of a sale and recommend grants to charities over time.

Start the conversation early
Begin charitable planning discussions in the early stages of a business interest sale or liquidity event. Starting early may preserve more planning options.

Weigh charitable goals alongside major decisions 
As you work through the deal, bring your charitable goals into the same conversations as your tax, estate, retirement, and wealth planning, so they’re considered together.

Complete the gift early 
If you plan to donate all or part of a business interest, begin discussing the gift well before the sale process is underway. Timing can affect the tax treatment of the contribution, so work closely with your tax advisor to understand applicable IRS requirements and evaluate your options before taking action. 

Some years look nothing like the ones before them. A Roth IRA conversion, a large bonus, significant investment gains, a deferred compensation payout, or another income event can push your taxable income well above the norm. In years like these, you can consider a charitable contribution which may provide an offsetting tax deduction, subject to applicable deduction rules and limitations.

As soon as you know 2026 looks different from a typical year.

A period of higher taxable income is often a good prompt to revisit your charitable strategy. Instead of treating giving as something you only think about at year-end, you can use a high-income year to see how your charitable goals fit into your broader tax and financial picture and to leverage itemized charitable deductions. For some, a DAF can help align timing, allowing you to potentially receive the potential effect of the contribution on taxable income and estimated tax liability while deciding later on the charities for your grant recommendations.

Understand how a Roth conversion affects your tax picture 
A Roth conversion is treated as a withdrawal and increases taxable income in the year it’s completed. Start by understanding how that additional income affects your overall tax picture and whether it opens the door to other decisions.

Coordinate the gift with the conversion  
Look at the conversion amount, any planned charitable contributions, and your estimated tax bill together. This can help you determine how much in income taxes you wish to offset with the charitable contribution and tax deduction.

Confirm your charitable deduction will provide a current-year benefit 
Not every gift reduces taxes in the year it’s made. The result depends on whether you itemize, deduction limits, and the type of asset you give. Review this early so you know what to expect.

Decide whether to accelerate future giving  
Use a high-income year as a chance to align charitable strategies with timing-sensitive decisions, such as accelerating planned gifts or funding longer-term giving plans.

• Reduce taxes on a Roth IRA conversion with charitable giving 

You recently participated in an initial public offering (IPO), received equity compensation, or hold company stock that has appreciated significantly, creating new investment, tax, and charitable planning decisions.

Before you decide whether to hold, diversify, or sell. Non-cash gifts can require extra due diligence and lead time, so build that into your timeline. 

A liquidity event is more than an investment milestone. It can also be a catalyst for a bigger planning conversation. When IPO shares, equity compensation, or other appreciated assets rise in value, you’re likely already thinking about diversification and taxes. That’s also a good time to think about how charitable giving fits in.

Evaluate charitable options before selling appreciated shares 
Selling highly appreciated stock can trigger capital gains taxes. Before selling, review charitable strategies while options are still available.

Confirm the shares are eligible to transfer 
You’ll usually need equity awards to vest, or to exercise them, before you can donate them. Company rules, trading windows, or transfer limits may also apply, so it’s worth checking early.

Review basis and holding period 
Check your original cost, how long you’ve held the shares, and the award type if the shares were acquired through an employer. These factors can affect both your potential deduction and capital gains treatment.

Review your shares through a tax and a charitable lens 
As you assess newly appreciated assets, identify which appreciated holdings have the largest gains and potential capital gains taxes, and consider whether they could support your charitable goals.

Look beyond cash gifts
Think about how different assets can serve different purposes. Appreciated stock may allow you to give more efficiently than cash while preserving other assets for other needs.

You give regularly, but your annual gifts may not be large enough on their own to exceed the standard deduction each year, which can limit your tax benefit. You may also be looking for a more intentional way to give, one that supports the causes you care about over multiple years.

Anytime, but especially if 2026 is a higher-income year. Set up time with an advisor to review your charitable goals and giving strategy before year-end.

See whether bunching fits your giving pattern 
Discuss with your advisor whether combining multiple years of planned giving into a single year could help align your charitable support with your overall financial plan.

Watch deduction limits and timing 
Check deduction limits before you bunch larger gifts. Beginning in 2026, some charitable deductions may still be available even when taking the standard deduction, but bunching may create additional tax-planning opportunities depending on your circumstances.  If you exceed limits for one year, you can typically carry the unused deduction forward for up to five subsequent tax years. Any eligible deduction generally relates to the DAF contribution, not later grant recommendations.

Understand what bunching unlocks 
Explore how a larger contribution in one year can create a charitable pool that supports giving decisions over multiple years.

Take a multi-year approach  
Look beyond annual giving decisions and use regular checkpoints throughout the year to revisit grants, adjust your plans, and stay connected to your long-term charitable goals.  

Bring family into your legacy 
Involve family members in conversations about shared values, priorities, and long-term charitable goals. Consider how bunching multiple years of contributions into 2026 could help establish new giving traditions and extend your family’s impact over time.