Fear of the Dark
Craig Swistun
Portfolio Manager
Lexicon Financial Group of Raymond James Investment Counsel
NOTE: This article was originally published under the banner “The Strategic Steward” with Future of Good (futureofgood.ca) in June, 2026. A link to that version is here.
I confess. I’m a big fan of the metal band, Iron Maiden. I suspect some of you secretly are, too. So, if you’ve ever listened to Fear of the Dark, you’ll remember how the song taps into something primal, the anxiety that comes from uncertainty, from sensing something you can’t quite see.
For many new board members, joining a charity board can feel a bit like that.
It’s not because the people aren’t welcoming or the mission isn’t clear. It’s because, especially for first-time board members, they can sense systems working in the background that are not fully defined. The bright lights of the boardroom and the polished onboarding binder can cast shadows over other important systems that help drive results.
And without visibility, even the most capable leaders might feel uncertain.
That’s because organisational history alone doesn’t illuminate the full ecosystem in which organisations operate. Too often, board members are left in the dark about the very infrastructure that fuels charitable work in Canada today.
That’s a problem. Effective stewardship depends on clarity. And you cannot be effective in a system you do not truly understand.
What’s Actually Hiding in the Shadows
The charitable landscape in Canada is not simple. It’s an integrated and often complicated network of tools, incentives, and strategies that shape how money flows into the sector.
Most are at least familiar with the idea that donors can give cash from their bank account or credit card and receive a charitable donation tax receipt. But without an understanding of appreciated securities, a board may underestimate a donor’s capacity to give in transformative ways. Without familiarity with donor-advised funds, they may miss how and where to follow up, losing the chance to deepen a relationship with a committed supporter. And without at least a working awareness of more complex vehicles, they risk missing conversations already happening among sophisticated donors and their advisors.
The challenge is that governance and stewardship decisions may shift toward what feels familiar: annual campaigns, events, and direct appeals. These approaches may be incomplete. Stewardship decisions may lack depth, and opportunities might pass unnoticed because no one at the table recognized them.
I certainly don’t expect board members to arrive with all of this knowledge in hand. After all, they are often accomplished professionals from a wide variety of fields. But why don’t more charitable organisations invest in educating their boards? Are they assuming that fundraising is the staff’s domain, tax-efficient giving is for accountants and lawyers to handle, and that board members will simply pick it up over time?
Given the state of the charitable sector in Canada, many organisations are out of time.
Turning on the Lights
I’m not suggesting that board members need to become technical experts. Far from it. But stewardship demands a certain level of philanthropic literacy.
It’s not unreasonable to expect directors to have a working understanding of how giving actually happens in Canada. But what does it mean when a donor wants to give securities instead of cash? Why might someone choose a donor-advised fund over a direct gift? How does an insurance policy become a philanthropic instrument? What about a planned giving strategy? How do you engage with donors exploring more complex approaches?
These are no longer edge cases. This is the scaffolding on which modern philanthropy is being built.
Let’s continue to tell organisational stories and explain past decisions. At the same time, charities and nonprofits should have a deliberate approach to teaching boards how the system actually works.
Create space for questions that might seem too basic. Demystify the tools donors and advisors are already using. Normalize not knowing, so that learning can happen quickly.
New (and old) board members bring energy and curiosity and a limited runway before they are expected to contribute meaningfully. Every meeting spent deciphering unfamiliar terms or wondering what is lurking in the shadows is a missed opportunity for impact.
Stewardship, done well, requires the lights to be fully on.
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.
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