Unfortunately, failure to ask the right/better questions risks encountering unwelcome surprises and less than optimal outcomes later for their wealth. For ultra-high-net-worth Canadian families and their family office advisory teams, the potential stakes are generally much higher.
Many millions of dollars are potentially at risk if investors do not offer up the right queries. Consequently, they might remain with a current wealth advisor who provides underwhelming advice, service or biases, or they risk selecting a poor match for their needs when seeking a new one after a significant liquidity event.
“One of my mentors in this business once said, ‘The quality of conversations with a wealth advisor or a client are the direct result of the quality of the questions asked,’” says Thane Stenner, founder of Stenner Wealth Partners+ at CG Wealth Management and Chairman Emeritus of ultra-high-net worth (UHNW) network Tiger 21 in Canada. He previously held award-winning consulting roles at Morgan Stanley/Graystone Consulting, based in California as Managing Director, International Client Advisor, Institutional Consulting Director, Alternative Investments Director and Portfolio Manager. He also hosts “Smart WealthTM with Thane Stenner,” a BNN Bloomberg podcast.
Recognized as one of Canada’s expert wealth managers, Stenner’s clients include family offices of Canada’s wealthiest families and entrepreneurs. To help them, his team has compiled a list of dozens of questions to ask their wealth advisors—for whatever the need—to ensure that they truly understand their advisors’ specialties, backgrounds, and real capabilities and potential shortcomings or biases.
Below are what Stenner views as the Top Five most important questions from that list that Canadian families and family offices should be asking their wealth advisors/consultants.
“How are you regulatory licensed?”
Asking a wealth advisor about their skills is fine and good, but if you really want to understand their strengths, weaknesses, limits, and even biases, inquiring about their regulatory licensing results in answers that speak volumes. “That question alone will dictate whether or not someone is eligible to recommend, for example, individual stocks and bonds for investments and potential biases,” Stenner says.
He points to how some wealth advisors may seem like investment experts, but only upon asking them this specific question is it revealed they are licensed only to sell insurance products like segregated mutual funds, which, in certain cases, have utility. But these wealth advisors may be extremely limited and potentially biased in the services and products they can recommend or comment on.
“Other wealth advisors, for example, are licensed to provide access to exempt market investments, alternative assets that aren’t publicly traded like stocks and bonds,” Stenner explains. Yet these same wealth advisors may not be able to provide discretionary money management for stocks, ETF’s, and bonds, which require different licensing.
My bias is that the broader a wealth advisor’s licensing, the more capable that wealth advisor might be able to advise on multiple holistic topics that can positively impact your financial well-being.
To that end, as a senior portfolio manager, Stenner is licensed with CIRO (Canadian Investment Regulatory Organization), as a securities market wealth advisor, and as an investment advisor for U.S. clients via FINRA. As a result, he and his team at Stenner Wealth Partners+ can provide comprehensive advice and access to a wide variety of investment opportunities. Notably, he adds, if you find out the wealth advisor you’re meeting with isn’t licensed at all, consider that a highly cautionary red flag, strongly indicating you probably should not be working with that individual for investment advice.
“How are you compensated?”
This is less about the fees you’re being charged—a much bigger topic for another day–and more about understanding a wealth advisor’s potential biases and conflicts of interest.
“If a wealth advisor is compensated 100 per cent from discretionary fee-based portfolio management, this generally means they’re specialist only in portfolio management of stocks, bonds and ETFs, and they might be less experienced in other areas of finance like insurance and alternative investments,” Stenner says.
Understanding how wealth advisors are compensated can reveal their strengths and biases beyond what licensing might indicate, he adds. “It’s also a bit of reverse engineering to see where the biases are.” For example, wealth advisors compensated wholly by commissions might recommend higher trading activity that may only benefit the wealth advisors and not necessarily their own wealth position.
“How frequently will I hear from you and your team?”
As an ultra-high-net-worth individual, you should expect white-glove, proactive service from your wealth advisors. So, it’s important to understand how often they will reach out on a regular basis, irrespective of how often you reach out to them.
Although the industry standard is meeting with clients once or twice annually, the more sizable your wealth, the more proactive communication you should expect from a wealth advisor. “The number one reason why people leave a wealth advisor or feel dissatisfied is they feel that they’re not receiving enough proactive attention,” Stenner says.
It’s not only about regularly scheduled calls or in-person meetings. It’s about ongoing communication, including emailing quarterly/monthly performance reports and providing easy access through 24/7/365 online portals to your financial plan and investment portfolios. “In a mutually beneficial relationship—which is what an advisor-client relationship truly should be—there should be a healthy back-and-forth through a variety of communication channels,” Stenner adds.
“What are your current and future views on the various markets?”
If your wealth advisor is managing your investments, it is essential you understand their view on the markets past, present and future. “It’s not just U.S. or Canadian equity markets,” Stenner adds. “They should be able to discuss global macroeconomic trends—interest rates and inflation—and a variety of asset classes like fixed income and alternatives, including cryptocurrency.”
Wealth advisors don’t need to be an expert in all these areas, but they should have a firm grasp nonetheless because no investment operates in isolation. What’s more, if you’re seeking a new wealth advisor, it’s doubly important to pose this question because “you want to be very sure you’re not just getting more of the same lacklustre advice you are wanting to move from,” Stenner says.
“How many clients do you serve?”
Wealth advisors with a successful practice are certainly desirable, but there is a limit to that success from a client perspective. “Wealth advisors with 500 clients? That’s great—for them,” Stenner says. “Obviously, they’re successful, but is a wealth advisor with that many clients really the best fit for you, who has tens, hundreds of millions of dollars or more in assets to invest/invested to monitor?”
Ideally, wealth advisors serving the ultra-high-net worth space should not have hundreds of clients. After all, you want to be sure they actually have the time to pay proper attention to your wealth needs, he adds.
While by no means exhaustive, these questions are a good starting point. That said, it’s likely beneficial to come armed to a meeting with even more. You can access Stenner’s PDF version of the full checklist here. He even suggests giving prospective wealth advisors the list, requesting they provide answers in writing.
What’s more, ask that they sign off on their responses, indicating these are true to the best of their knowledge. “That reduces any potential misleading misinformation and truly fosters a relationship built on 100-per-cent trust and accountability,” Stenner says.
*Responses have been lightly edited for clarity and length.
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Thane Stenner Interviews/Articles, Member of Canadian Family Offices.
About Stenner Wealth Partners+
Stenner Wealth Partners+ (SWP+) is an in person/virtual Multi-Family Office/Outsourced CIO Consulting team of financial/wealth specialists with a boutique approach and global perspective. SWP+ serves Canadian and US investors/households with generally a minimum of 10M+ in investable assets or 25M+ net worth. As a CG Wealth Management team, SWP+ is a highly exclusive practice team with one of Canada’s largest independent wealth management firms. Client Range of Net Worths: between $25M To $3B+. They strategically limit new client engagements, onboarding only six to eight new key relationships annually to ensure a highly personalized and focused approach. SWP+ is a member of Canadian Family Offices.
About CG Wealth Management
The global wealth management business is entrusted with C$125.3 billion in client assets1. The wealth management operations of the Canaccord Genuity Group (CG Wealth Management) provide comprehensive wealth management solutions and brokerage services to individual investors, private clients, family offices, Donor Advised Funds (DAFs), and intermediaries through a full suite of services tailored to the needs of each client.
1Canaccord Genuity Annual Report, June 30, 2025
Disclaimer: This story was created by Canadian Family Offices’ commercial content division on behalf of Stenner Wealth Partners+ at CG Wealth Management, which is a member and content provider of this publication. CG Wealth Management is a division of Canaccord Genuity Corp., member of CIPF and CIRO. Tax & Estate advice offered through Canaccord Genuity Wealth & Estate Planning Services Ltd. Thane Stenner’s views, including any recommendations, expressed in this article are his own only, and are not necessarily those of Canaccord Genuity Corp.