Often, donors and others can be quick to try to make a distinction between “good giving” and “bad giving.”   “Good giving” supports programs that are high-impact, low-overhead, and focused on root causes.  “Bad giving,” in contrast, supports short-term fixes to longstanding problems, simply addressing the symptoms of systemic problems.  And while this advice might actually be quite good, not all donors’ passions, goals, and timelines can fit this one-size-fit-all mold. Philanthropy is a deeply personal act, informed by emotion, intuition, and often very difficult and unique experiences. 

And yet, donors sometimes feel like they need to de-emphasize their own passion and goals, and instead pay attention to the “numbers” of philanthropy – the seemingly objective measurements of an organization’s health and effectiveness.  And while numbers, like the volume of services provided, are very important to review, focusing too closely on only the numbers can take away the joy of giving.

And why is it important to protect the joy of giving?  Because people who love their giving tend to give more.  These donors build relationships with their grantees and view these organizations as their partners in carrying out a philanthropic vision.  These donors are interested in both outcome and process.  They want to be inspired by their giving, and motivated to continue giving into the future. And they want their giving to have a real, lasting, and profound impact on people’s lives. 

To these individuals, we can never say to simply look at a ratio of program expenses to administrative expenses or to focus on the executive director’s salary.  Instead, we ask them to spend time thinking about their passion, what excites them or makes them angry, their risk tolerance, and many other factors that will reveal the type of giving that will be best for them and their grantees. 

While every donor is different, I have found that the donors who find the most meaning in their giving share four attributes: they are compassionate, authentic, trusting, and skeptical.  Luckily, these attributes form a handy acronym, CATS, which offers a model that donors can employ to determine if a new funding opportunity really is right for them. 

Let’s break down what these qualities mean in the context of philanthropy: 


While the actual beneficiaries of one’s giving might be unknown, and in some cases difficult to even identify, all giving should be driven by the idea that “we’re all in this together,” and an understanding of your level of responsibility to your fellow human, and to all living things.    

When considering a new major gift or strategy, ask yourself: who is this helping?  This can be an easy question to answer in specific cases, like when you are providing scholarships for underserved students or support for a food bank or shelter.  But what about situations where the impact is more hidden?  In these cases, researching the issue and understanding the long-term impact is a top priority.  For example, donating a wing for a museum doesn’t appear compassionate at first glance until you take the time to understand how exposure to the arts has an impact on student outcomes. For some young people, art is what has kept them in school, sparked their own creativity, and created a future life filled with accomplishment, curiosity, and discovery. 

So, when contemplating a compassionate gift to a museum, ask what opportunities exist to expose children from underserved communities to the art in the new wing.  Ask about the museum’s arts education programming, its track record in bringing art to specific communities, and how it partners with other organizations.  Adding a compassionate lens to your giving will require more research and tough questions for the grantee, but it will also result in a grant that is likely more satisfying, with greater impact.  It will also help you to find the right organization -- the one that shares your values.

So, whenever you are thinking about a new large gift or giving strategy, it’s best to start with the questions: “Who will be helped, how, to what extent, and how can my gift make an impact?”


For several reasons, philanthropists are sometimes pushed into supporting causes they think they should.  They might feel guilty if they are not addressing the root causes of issues.  Or they might feel they must support the passions of their spouse, parents, friends, etc.  They might even feel pressured to go along with philanthropic trends that they aren’t familiar with (such as microloans). And while there is certainly nothing wrong with these types of giving, they may fall short of exciting the donor. 

To these people, I say be authentic.  Begin by understanding your motivations for giving. If you want to feel like a generous person as a result of the gift, then give a gift that will make you feel good.  If you want to dive into a process that will challenge your thinking and understanding of all the many factors that lead to the cause of an issue, then supporting the advocacy, education, and analysis that will excite you.  People are often very self-conscious about their giving, as though the approval of their peers is the driving force behind their philanthropic choices.  While I understand that every donor wants to “do it right,” the ones that are most successful first ask: “what is right for me?”


It is often very difficult for new donors to trust the nonprofits that they invest in. And that’s understandable when you consider the negative press surrounding some nonprofit organizations.  Unfortunately, negative stories make the headlines – people often hear of the administrative assistant embezzling millions of dollars or the “charity” that spends nearly all its money on extravagant salaries, bloated travel budgets, and galas. 

And while most donors will acknowledge that these are just the bad apples, they still have a difficult time letting go and trusting their philanthropic partner.  So, how do you build trust? Build it through conducting research, analyzing past successes, and talking with donors.  Ask the organization tough questions about why it has chosen the strategies it has, the track record of its leadership, how it survived the 2008-2009 downturn, etc. 

But after you have asked these questions and received answers that satisfy you, then you make the grant, and you trust that your partner will do the right thing. Trust that your grantee will spend your funds wisely, but also require that the organization provide a report that outlines the impact of the grant.


Okay, I know what you’re thinking.  Isn’t being trusting and skeptical contradictory? In some ways, it is. 

The donor must be skeptical of any program that an organization is willing to create to align with the goals of the donor.  If, after hearing the donor’s goals, the organization says, “yes, that’s exactly what we’re hoping to do,” the response should be “why haven’t you done it yet?” The response to this question will let you know if the new initiative is a priority for the organization. And, of course, if the program is created for the donor, then the donor will have the moral responsibility to support it over the long term.

At the same time, donors should be skeptical of their own “brilliant ideas.” But, rather than shy away from innovation, donors should approach their epiphanies in the same way that a company might test out a new product.  Before any resources are committed, there would be focus groups, research, and strategies in place.  The success of the product (or in this case, the program) would need to be seen as likely based on solid theory and broad community acceptance. 

So, for the donor who is interested in supporting the next big thing, I encourage them to ask themselves and their potential grantee “why hasn’t this been done before?”


There are far too few people in the world with the ability to make major, game-changing gifts.  And there are even fewer who are able to take the time to turn their major gifts into transformational grants.  I have seen that donors will make the transition to the transformational philanthropist only when they are challenged by their giving, rewarded by their giving, and yes, love their giving.


Mitchell Singer has over 15 years of experience in philanthropy, nonprofit management and government. As a Director at Rockefeller Philanthropy Advisors, Mitch advises on foundation management, legacy grants, grantee due diligence, amongst other topics. Before joining Rockefeller Philanthropy Advisors, Mitch served as Associate Director of The Center on Philanthropy and Public Policy at the University of Southern California, an academic research center that studies the field of philanthropy. He received his B.A. from San Francisco State University and his M.B.A. in Nonprofit Management from American Jewish University.