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Unlocking the Potential: Expert Tips for Successful Estate and Gift Planning

Expert Sources: Ann E. Kolakowski, CAP®, CFRE, and Kyle Paige, JD.

Graduates tossing caps

In philanthropy, estate and gift planning are potent avenues for individuals to leave a lasting impact on causes dear to their hearts. However, navigating the intricate landscape of planned giving, encompassing everything from complex asset donations to tax optimization can be a formidable task. To shed light on this subject, we turn to two distinguished experts:

Ann E. Kolakowski, CAP®, CFRE, is an unabashed advocate for all things planned giving. The immediate past president of the National Capital Gift Planning Council, she currently serves as Director of Gift Planning Services for the University System of Maryland, the state's public higher education system.

Kyle Paige, JD, is the Executive Director of Estate and Gift Planning at the University of Miami. She has deep expertise in planned giving and guides donors through complex financial landscapes, shaping lasting philanthropic legacies. She is dedicated to advancing planned giving and empowering impactful legacies.

Embracing Complex Assets in Planned Giving

The potential for impactful giving extends beyond traditional avenues. Donors are increasingly exploring contributing complex assets such as real estate, closely held businesses, and intellectual property. But how can these unconventional gifts be effectively integrated into planned giving strategies?

Ann emphasizes the transformative potential of complex asset donations. While these gifts can be a game-changer for donors and charitable organizations, they demand careful planning and execution. Organizations should establish clear gift acceptance policies to navigate these unique contributions. For assets falling outside the policy's purview, third-party experts can manage the process, ensuring compliance with tax regulations and maximizing the gift's value. Throughout this journey, transparent and consistent communication is vital to manage expectations effectively.

"Giving complex assets to charity can be a very taxwise, financially savvy strategy." -Kyle Paige.

Donors not only receive immediate charitable tax deductions but also reduce their capital gains tax liabilities. Moreover, this strategic approach can help alleviate estate taxes and lighten the financial load for heirs. Kyle introduces various planned giving vehicles, such as charitable remainder trusts and charitable lead trusts, tailored to donors' specific goals. Timing is crucial, especially when engaging potential donors on the brink of selling their businesses or real estate. Smaller organizations do not need to feel overwhelmed; charitable giving consultant companies can provide invaluable assistance. Keeping gift acceptance policies up-to-date ensures that organizations can adapt to the evolving landscape of philanthropy.

Enhancing Planned Giving Strategies

Optimizing tax benefits is a pivotal consideration when it comes to planned giving. However, as Ann and Kyle emphasize, it's crucial to tread carefully and never offer tax advice without consulting financial and legal experts.

Ann suggests donors explore alternative assets, like long-term, highly appreciated securities, to fund their gifts. This strategy offers an immediate charitable deduction, sidesteps capital gains taxes, and enables the charity to utilize the full gift value. Donors can later repurchase the donated shares on a stepped-up basis, avoiding future capital gains. Ann notes that while cash donations are common among high-net-worth individuals, donating marketable securities remains largely untapped.

Kyle underscores the need for gift planners to stay informed about evolving tax laws and regulations. Maintaining a network of advisors, including attorneys, accountants, and financial experts, is instrumental in comprehending these changes and their implications. Educating other advisors who may need to be better-versed in planned giving tax benefits

is equally vital. As well as the importance of donor conversations about their charitable goals and financial situations to make informed decisions aligned with their tax and financial objectives.

Integrating Family Needs with Philanthropic Legacy

Balancing a family's financial needs with a philanthropic legacy is a core aspect of planned giving. Ann highlights the flexibility of most planned gifts, emphasizing that they don't require donors to part with assets immediately. Whether it's including a nonprofit in a will, naming them as beneficiaries of retirement plans, life insurance policies, or other accounts, donors can adapt their plans easily.

"This flexibility provides peace of mind to those who want to help a charity but are rightly concerned about providing first for themselves and their family." -Ann Kolakowski.

Planned gifts such as charitable gift annuities and charitable remainder trusts are other giving channels that provide income to donors and beneficiaries while also providing benefit to the nonprofit organization. Charitable lead trusts, particularly, support organizations for a specified period before assets revert to the donor's family or other beneficiaries, offering substantial tax incentives.

Kyle emphasizes the diverse array of planned giving options, asserting that there's a suitable plan for everyone based on their financial situation.

"We like to say that there is a planned gift for everyone." -Kyle Paige.

Some donors may benefit from trusts' tax savings and financial advantages, while others may prefer bequests. Fundraisers play a crucial role in helping donors explore their options, always emphasizing the importance of seeking advice from their advisors.

Cultivating Planned Giving: Strategies for Attracting High-Net-Worth Donors

Promoting planned giving opportunities to high-net-worth individuals requires a strategic approach. Ann compares the work of a planned giving professional to that of a gardener, emphasizing the importance of preparation.

"I like to think that the work of a planned giving professional correlates to that of a gardener: we prepare the soil, remove the rocks, plant the seeds, add fertilizer, water, weed, prune, and wait .... until harvest. It’s a long process." -Ann Kolakowski.

Ann continues, "The donor is the one who decides when to plant, but it's our job to have that field prepared and to ensure that the flowers bloom."

Personalized marketing and additional communication methods such as surveys, storytelling, and QR codes redirecting individuals to a specific webpage are also valuable tools. Some organizations even use virtual reality to showcase their work. Maintaining direct mail alongside newer strategies can cater to various donor preferences.

In addition to omnichannel marketing strategies, Kyle recommends exclusive events, including discussions on planned giving's financial benefits. Direct marketing communications highlighting tax advantages of specific vehicles are effective. Building a network of advisors who work with high-net-worth prospects is essential, as these advisors can introduce your cause to their clients. Consistency in messaging and personalized interactions are crucial to engage high-net-worth individuals successfully.

Nurturing Long-Term Relationships with Planned Giving Donors

Building and maintaining relationships with donors is paramount in planned giving. Personalized communication, tailored engagement, and unwavering commitment to a donor's philanthropic vision are the cornerstones of effective stewardship.

Ann emphasizes that planned giving donors should be treated as the major donors they are,

"Being included in someone’s estate or overall financial plan is a place of privilege, not to be taken for granted." -Ann Kolakowski.

Understanding each donor's preferences regarding engagement is crucial—some may desire anonymity, while others appreciate the spotlight. Personal touches, like handwritten notes, birthday cards, and phone calls, can be cost-effective methods to show appreciation. Utilizing video calls for donor interactions is also an option. Legacy societies play a pivotal role in recognizing donors' special commitments and fostering a sense of community among them.

Connecting donors to the cause by providing insights into the impact of their potential gifts often leads to organic planned giving commitments. Once committed, ongoing stewardship is vital, potentially spanning years, as planned gifts can be revocable. Annual plans, birthday cards, gratitude messages, luncheon invitations, and special events can help maintain engagement and express gratitude.

Empowering Donors with Knowledge: The Art of Planned Giving Education

Educating donors about the vast array of planned giving options is a pivotal aspect of fostering philanthropy. Simplifying the perceived complexity of planned giving and empowering donors with informed decisions is essential.

"Planned giving has an unfortunate reputation for being overly complicated and mysterious, when at its core it’s about using creative approaches to accomplish meaningful goals." -Ann Kolakowski.

Similar to any donor qualification approach, beginning with the "why" and then delving into the "how" along with open-ended questions help identify a donor's goals and help to align their goals with the organization. Engaging the donor's trusted advisors, such as financial planners and attorneys, in the conversation aids in choosing the best gift vehicle and assets. Creating microsites and accessible materials can be beneficial. Clear communication is critical, ensuring that donors from various backgrounds comprehend planned giving concepts. A good rule of thumb is to ask, "How would I explain this to my grandmother?" says Ann.

Kyle underscores the importance of consistent marketing and education. Donors have varying timelines for updating their estate plans, so maintaining regular planned giving messaging is vital. Employing diverse communication modes, including electronic and print formats, caters to different donor preferences. Catching donors' attention with concise, impactful statements about leaving a legacy can be highly effective. Sharing stories and testimonials showcasing the impact of philanthropic gifts and the chosen planned giving vehicles resonates better with donors than technical jargon.

Enhancing Planned Giving Through Team Collaboration: A Winning Strategy

Ann and Kyle emphasize the need for breaking down silos and promoting teamwork to maximize the impact of planned giving efforts.

Ann highlights the significance of cultivating a culture within the advancement department that encourages shared objectives, collaboration, and metrics to gauge success. To broaden the scope of planned giving beyond legacy gifts, all development team members must have a fundamental understanding of planned giving concepts. Gift officers should actively listen for indications that a planned gift might be suitable and provide information accordingly. Incorporating a dual ask when discussing potential endowments, which involves requesting a gift to establish the fund and a bequest to augment it in the future, should become a standard practice. Alumni programs can offer workshops or webinars on financial and estate planning while incorporating the legacy message. Annual fund and research teams can identify potential legacy donors among loyal, low-dollar contributors and include planned giving messages in their appeals.

Kyle underscores the importance of educating gift officers at all levels about the value of planned giving and how to identify prospects, initiate conversations, and grasp the basics of primary planned giving vehicles.

"Nurturing the relationship with other gift officers leads to trust and credibility so that those gift officers want to bring in the planned giving team from the outset as a resource." -Kyle Paige.

Relationships are strengthened through consistent engagement, including regular meetings and portfolio reviews, leading to more planned giving conversations and increased lead generation and gifts-closed.

Embracing Technology, Data, and Trends

The significance of data analysis and analytics in understanding donor behavior and preferences is growing. By segmenting donors effectively, nonprofits can tailor their communication strategies and identify potential planned giving prospects. Ann reminds us that planned giving is open to anyone, regardless of gift amount. She highlights the importance of reaching out to underrepresented groups like women and people of color who increasingly control substantial portions of wealth.

"We need to be examining our biases and definitions of what it means to be a philanthropist." -Ann Kolakowski.

Another trend that cannot be overlooked is the use of Donor Advised Funds (DAFs). These "charitable checkbooks" offer a cost-effective alternative to private foundations without the required 5% annual payout. The donor receives an immediate charitable deduction for gifts to the DAF and can then recommend grants to qualified charities. As of 2021, there were more than 1.2 million DAFs in existence. DAF grants have grown 400 percent in the last decade, yet more than $234 billion is sitting in these accounts, waiting to be put to use. You may be missing out if you are not asking your donors if they have a DAF. Lastly, after many years of hearing it was on the way, we are finally beginning to see gifts that represent the Great Wealth Transfer from the youngest members of the Silent Generation and the oldest Baby Boomers (who are turning 65 at the rate of 10,000 per day). From now until 2050, an estimated $11 trillion is expected to pass to charities from these donors. You can no longer afford (literally) to delay your foray into planned giving.

Kyle reinforces the importance of technology and data analytics in planned giving programs. It's essential for planned giving programs to use technology and data analytics and to be on top of emerging trends to leverage resources to maximize outreach to donors effectively and strategically. Data analytics, particularly wealth ratings and planned giving scores (which combine factors like age, wealth capacity, and giving history to give a planned giving capacity score). At the same time, they aren't always completely accurate and shouldn't be relied on to exclude individual research. They help produce targeted prospect lists to help maximize time and effort. Using data to pull lists of loyal donors (10 years or more of consistent giving) is also vital to a planned giving program, as these prospects are your organization's highest affinity donors and those more likely to be in the planned giving prospect age category. Leveraging technology like Chat GPT can streamline communication and save time in planned giving marketing. Staying updated on emerging trends in the charitable giving industry is crucial for seizing opportunities to engage donors effectively.

Small Advancement Shops: Launching or Growing Planned Giving

Starting or expanding a planned giving program in a smaller organization requires dedication and strategy. Ann offers guidance tailored to limited-resource settings:

  1. Gain Leadership Support: Secure leadership buy-in using data like GivingUSA and Philanthropy Pulse.

  2. Engage Loyal Donors: Focus on your top 100 loyal donors and volunteers for targeted outreach.

  3. Prioritize Wills and Beneficiary Designations: These form the bulk of planned gifts.

  4. Optimize Website: Ensure crucial info is accessible and consider partnering with a planned gift marketing vendor.

  5. Create a Legacy Society or Data Code: Recognize planned gift donors uniquely.

  6. Appoint a Coordinator: Designate a staff member to oversee planned giving efforts.

  7. Lead by Example: Consider making a planned gift yourself, inspiring potential donors.

Small shops can establish a valuable planned giving program for long-term sustainability with these steps and persistence.

Kyle offers invaluable advice for smaller advancement teams looking to kickstart a planned giving program:

  1. Establish Foundation: Build essential infrastructure, including a gift acceptance policy, donor data, nonbinding letter of intent, recognition procedures, and stewardship plans.

  2. Start Small: Focus on a bequest campaign initially.

  3. Incorporate Bequests: Mention bequests consistently in all development communications.

  4. Utilize Third-Party Services: Consider investing in planned giving services from companies like Stelter or Crescendo for templated marketing materials and guidance.

  5. Landing Page: Develop a dedicated web page on your site for bequests, promoting it widely with QR codes, business cards, and email signatures.

Smaller shops can effectively introduce planned giving and raise the organization's long-term sustainability by taking these steps.

In conclusion, planned giving is not a morbid endeavor; instead, it's a pathway for donors to embrace the joy of philanthropy and create lasting impacts. While some planned gifts may seem complex, most are straightforward to arrange. Ann reminds us not to let the fear of the unknown deter us from facilitating meaningful contributions. By adhering to the strategies and insights shared by Ann and Kyle, organizations can embark on a journey of planned giving success, fostering strong relationships, optimizing tax benefits, educating donors, and collaborating effectively within their advancement teams. At its core, planned giving is about shaping a brighter tomorrow through thoughtful and intentional giving today.

The information in this article is offered for informational purposes only and should not be construed as legal or tax advice, nor is it intended to replace the advice of a qualified attorney or tax advisor. Always recommend that donors consult with professional advisors prior to making any philanthropic planning decisions.


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Shaff Fundraising Group is a consulting firm specializing in fundraising, marketing, and analytics. We take pride in our independent approach, free from technology affiliations with SaaS and other companies. This allows us to provide objective, solutions-oriented support to our client partners and the wider fundraising and engagement community.


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