The Strategic Steward — July 2026
EDITION 004 : July 2026
The Seeds of Doubt
People haven’t stopped caring. They’re just asking more questions and looking more closely. One of the questions they are asking is, “Why haven’t I been told?” And that’s not good.
Charity Spotlight
Back in March, as part of our Grow for Change project, we released interviews with Caitlin Bailey, former Executive Director of Vimy Foundation, and Spencer Tittley, Fundraising and Communications Coordinator for Ottawa’s Parkdale Food Centre.
Required Reading
Links to articles and books to keep you inspired.
THE SEEDS OF DOUBT
NOTE: A revised version of this article was published under the banner “The Strategic Steward” with Future of Good (futureofgood.co) July 2026. A link to that version is here.
Remember the days when nonprofits could rely on a steady stream of support from a dedicated and loyal following? Organisations that were successful in building a connection and reinforcing it with real stories of impact took stewardship seriously and were rewarded.
There’s been a change. It isn’t that people no longer trust nonprofits. It’s just that the trust has been diluted. Where donors used to believe they had a limited number of organisations from which to choose, they are now acutely aware that they have options. With over 80,000 charities, online giving platforms, and countless more nonprofits asking for support, the chessboard has changed. Access to information has never been higher, and individuals, corporations and even foundations are asking harder questions before they commit their time, treasure or talent in support of a cause.
Trust is no longer inherited from reputation alone. It’s negotiated, evaluated, tested and earned in a world with seemingly infinite choice and near-perfect visibility. Organisations who haven’t been paying attention may be caught off guard. In a different context, Ernest Hemingway captured the same truth in The Sun Also Rises. Exploring how change happens, he writes: “Two ways. Gradually, then suddenly.”
“Suddenly” is now.
The Slow Introduction of Doubt
As someone with an English degree, I often try to find parallels in literature. Take the play Othello, for example. Othello believes that his beloved Desdemona is having an affair, because the character Iago plants and nurtures the seeds of doubt. The tragedy unfolds from there.
Effective stewardship involves ensuring that you are not leaving room for doubt to creep in or take hold. Today, supporters want to know:
Why is this problem worth solving?
Why is now the best time to invest in solving this issue?
How effective are you at solving the problems you are working on?
How are you going to communicate your success or failure with me?
If people are wondering “what am I not being told”, they are already having doubts.
When Evidence Comes Too Late
When impact is unclear, delayed, or difficult to interpret, donors do not sit in silence and wait; they begin to construct meaning from what is available:
partial information
generalized language
narrative without verification
Shakespeare teaches us that by the time clarity comes to erase doubt, some damage may have already been done. Restoring trust is more difficult than keeping it in the first place because it involves rebuilding the platform on which trust once rested.
The Story Problem in a Low-Trust World
In a skeptical environment, marketing, communications, and even the stories that charities tell about their work change. They become open to interpretation. A donor encountering a compelling story today may not simply feel moved. After all, they are exposed to many such stories on a regular basis.
What donors see is often:
broad summaries instead of direct connections
outcomes described in abstract terms
results that require interpretation rather than offering it
This creates the same condition that Shakespeare warned about, a space where meaning must be filled in by the observer. Doubting supporters inevitably begin asking, “How is this story relevant to me?”
If your communications and marketing cannot withstand scrutiny, it’s trust that suffers. And support may fade away, not gently but suddenly.
The response cannot be volume. More reports, more updates, more stories will not resolve a structural shift in how information is received.
The standard must be clarity:
connect donor action directly to outcome
remove the need for interpretation
arrive early enough to prevent doubt from forming
eliminate ambiguity before it can be exploited.
The Mandate Now
In literature, comedy and tragedy often come from recognizing the truth too late. In stewardship, however, the opportunity to change is still there, though it may require a fundamental shift in how organizations build trust with their supporters.
Because trust is no longer the starting point of a relationship, it must instead be understood as a conclusion donors reach based on available evidence. That is an important shift, and not an easy one. It demands earlier clarity, stronger proof, and a willingness to eliminate ambiguity before it has a chance to take hold.
And yet, even in the most well-constructed case for support, a new dynamic has emerged. Douglas Adams once described it, somewhat playfully, as the salmon of doubt. Today’s donors don’t passively receive information—they actively push against it. Like a salmon swimming upstream, they move against the current of messaging, testing claims, questioning assumptions, and looking for gaps before accepting what they are told.
For organisations to succeed, they will need to anticipate doubt and respect it. Because in the end, we’re actually not talking about Shakespeare or salmon. We’re talking about change.
Charity Spotlight
In March, through our Grow for Change project, we published two interviews that profiled Canadian charities that are making a difference. All episodes are available in video format on YouTube or in an audio-only format through Spotify. Listen now to learn more about the great work these groups are leading.
Vimy Foundation works to preserve and promote Canada’s ongoing legacy of leadership through youth programs, commemorative projections and educational resources.
Ottawa's Parkdale Food Centre is fighting food insecurity in a different way. Rather than distributing hampers of pre-collected food, they allow their neighbours to select foods that are culturally significant or that cater to specific dietary needs. In this way, they operate more like a community grocery store than a traditional food bank.
Required Reading
A curated collection of articles and books meant to inspire you.
What can I say about Uncharitable, by Dan Pallotta, except it is a must-read. Pallotta rose to some prominence with his March 2013 TED Talk titled “The way we think about charity is dead wrong”. It has opened more than a few eyes to the fact that the way the sector works could benefit from some new approaches.
Kevin Brown’s Fundable & Findable: The Brand-New Way to Fix your Nonprofit Fundraising provides frameworks for building clear, differentiated brands in the nonprofit space. He posits that if your work is unseen and unheard, it will probably be unfunded. To break the cycle, you might need to switch gears.
Craig Swistun is Portfolio Manager with Lexicon Financial Group (www.lexiconfinancialgroup.com) at Raymond James Investment Counsel.
The opinions expressed are those of Craig Swistun and not necessarily those of Raymond James Investment Counsel which is a subsidiary of Raymond James Ltd. Statistics and factual data and other information presented are from sources believed to be reliable but their accuracy cannot be guaranteed. It is furnished on the basis and understanding that Raymond James is to be under no liability whatsoever in respect thereof. It is for information purposes only and is not to be construed as an offer or solicitation for the sale or purchase of securities. Raymond James advisors are not tax advisors and we recommend that clients seek independent advice from a professional advisor on tax-related matters.
There is no relationship between Raymond James Investment Counsel and either Vimy Foundation or Parkdale Food Centre. Participation is at the viewers discretion. Images were created using Adobe Firefly.
