10 Things I Learned About Grantmaking
JSF Board Chair Malcolm Macleod has learned a great deal during his more than 30 years of working in philanthropy. He has been instrumental at the Foundation in implementing impactful grantmaking strategies that help disadvantaged people groups pursue education and employment opportunities.
Here, he shares some of his lessons learned, which are discussed in more detail in his recently published book, “The Practice of Philanthropy: A Guide for Foundation Boards and Staff.”
It’s written for donors big and small—whether they are foundations or families who want to make the world a better place.
Read on to learn how effective grantmaking can have major impact on your grantee partners and your organization.
1. Grants are investments
Practice grantmaking like you mean it. Whether you are making grants yourself or acting through staff, grantmaking activity must be purposeful and organized. Treat your grants like the precious investments they are.
Foundation investing is different from “for profit” investing. Financial success is uncorrelated to the quality of your grantmaking or the quality of your grantee partners. Your “return” is social benefit, not profit, and your strategies will be different.
2. Knowledge is your foundation’s vital second asset
Foundation leaders should immerse themselves in their fields of interest. It is the best way to learn. This is where your ideas will come from. Knowledge and ideas will inform your strategy and make it better. Learning is at the heart of good grantmaking practice.
3. There is a power imbalance
When you deal with potential grantees, the most important thing for you to understand and always remember is that there is a gross inequality of bargaining power between foundation and grantee. This makes it difficult for grantees to trust foundations and inhibits honest dialogue. It can also interfere with the grantmaking process and make the foundation’s work more difficult. The power imbalance cannot be eliminated, but foundation behavior that demonstrates trust in its grantee partner should, over time, mitigate its effects.
4. Grantmaking is an iterative process
Great ideas do not usually arrive in final form. They build on each other and improve. The practice of good grantmaking often leads to better grantmaking. Knowledgeable grantmakers can play a big part in the iterative process of ideas and help propel the evolution of strategy.
5. Foundation grantees are partners
Do not use the term “partner” in a patronizing or careless way. Realize that your grantee partners are the ones who do the work of advancing your foundation’s mission. You need them as much as they need you. You invest, they work. Once you commit to the concept of partnership there are two things that follow. Choose grantees carefully. Choose grantee partners you can trust and treat them with respect. They invariably know more about their work and the related issues than you. They are the teachers, and you are the student.
6. Give grantees the tools.
The best grants are those that empower people and organizations to be more independent.
7. Embrace risk (and failure)
Foundation grants are risk capital. Allocate some or all of your grants to new organizations and ideas. Foundations are free. They are independent of the marketplace and public approval.
New ideas and methods will require foundations to be different, to go against the grain of conventional thinking. Foundation independence permits this. Setbacks and failures are a necessary part of innovation. Have the courage to be honest with yourself and transparent with the world. This is a cultural issue for foundations. They must consciously create a culture that embraces risk and develop policies to reward bravery and innovation. Leaders must show humility and openness about their own mistakes and imperfections. This will give everyone the courage to speak up and advance new ideas.
Risk is not the same thing as recklessness. Knowledge, experience, and strategy will inspire risk taking. Recklessness is born of ignorance and impulse. Know and practice the difference.
8. Realize that some grantmaking is more difficult
Trying to help people solve seemingly intractable problems is a high calling for a grantmaker. Both grantmaker and grantee must feel their way along with all the self-doubt that this entails. If there were an easier way or even a clear course, it would likely have been found already.
Grantmakers must be patient and accept small victories. There is usually no silver bullet. Slow progress is better than what preceded it (nothing). And if grantmakers won’t do it, who else can or will? Above all, be honest and transparent about your grants and results. There is much to learn from your experience.
9. Beware of unintended and unwanted consequences
Grantmakers should respect the power of money and not wave it around like a magic wand. The best insurance against unintended consequences is a good knowledge of, and an honest relationship with, your grantee partner.
10. Make freedom and independence your foundation’s greatest asset
Dedicate part of your grant budget to tackle difficult problems that others cannot or will not. The opportunities, large and small, are boundless, and they are out there waiting for you. Use your freedom to go out and find them.
About R. Malcolm Macleod, K.C.
Malcolm Macleod was born in Amherst, Nova Scotia in 1951. He obtained a B.A. in English (Honors) in 1975 and was awarded a Lord Beaverbrook Scholarship to study law at the University of New Brunswick.
Malcolm was admitted to the New Brunswick Bar in 1978 and to the Nova Scotia Bar in 1979. He joined the firm of Patterson, Smith, Mathews and Grant as an associate and practiced with that firm and its successors for over 25 years. During that time he served as managing partner and chair of the firm’s litigation department. He was appointed Queen’s Counsel in 1997.
Malcolm joined the Johnson Scholarship Foundation as a trustee in 1993. He was elected secretary in 1995 and served in that position until 2001, when he was elected President and Chief Executive Officer. He retired from that role in April 2020 and accepted the Board’s invitation to serve as Chair of the Board of Directors.
You can read more of his insights in his newest book, which is available for purchase.

















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about Indigenous communities while still challenging and cultivating change. The narrative of native youth is one of hope and resilience. It is one that is dedicated to serving its people and preserving its culture. We all can learn a great deal from Native youth.
others in their field of endeavor. Often we just show up to meet students or help our grantees raise money.
assets to grantee partners. Funders can use their networks to leverage financial support,
the support for the grant-funded program, and to ensure sustainability after the grant ends. A match ratio quite literally increases the value of the grant and creates an
they are opportunities for us to show our appreciation for the partnership and personally invest in the program. The presence and participation of funders in these types of celebratory events inspire and ensure support.
book and website publishing at The Philanthropy Roundtable. He has authored 12 books, including
Inauguration of Andrew Jackson (1829) was a drunken, destructive riot and that, at various times in the 18th and 19th centuries, Congressional debate descended into fistfights or worse. Governments have, at times, been misguided or dysfunctional or both. The secret to America’s advancement is that it has always been a country with many independent centers of power. Who can doubt that in a free society most decisions are made by “the market” and not government?
day and the press were not sympathetic and turned a blind eye to mob violence against anti-slavery advocates and the destruction of their houses. But the brothers kept going and built a movement that culminated in the abolition of slavery less than 30 years later.
governments plus the United Nations. Current examples of philanthropic leadership can be found in the fields of education, research, job training programs, public works, micro-lending, foster care and adoption.