How to tell the difference between someone who manages money and someone who can actually help you.
After a major liquidity event, you’ll have no shortage of people wanting to manage your money. Your bank will call. Old friends in finance will resurface. You’ll get referrals from colleagues, LinkedIn messages from strangers, and probably a few cold calls.
Everyone will sound confident. Everyone will have nice offices. Everyone will promise they can help.
So how can you tell which investment advisor is actually worth your time?
After nearly 15 years in the wealth management industry, working at inside one of Canada’s largest pension funds, writing a book—and now advising high-net-worth professionals—I’ve learned that the right questions reveal everything. Here are five that will separate the advisors who can genuinely help from those who are simply gathering assets.
1. “How do you get paid, and how much will I pay in total?”
This seems obvious, but you’d be surprised how hard it is to get a straight answer.
Many advisors quote their fee (say, 1%) but fail to mention the underlying fund fees (another 0.5-1.5%) baked into the products they recommend. On a $2 million portfolio, that’s the difference between paying $20,000 per year and $50,000 per year.
A good advisor will walk you through the complete cost picture in writing. If they get vague or defensive, that tells you something.
2. “What investments do you have access to that I can’t buy myself?”
This question exposes whether an investment advisor actually adds value beyond hand-holding.
If their answer is essentially “we’ll build you a diversified portfolio of stocks and bonds”—you can do that yourself with a few low-cost ETFs. You don’t need to pay someone 1% annually for that.
The advisors worth paying for have access to investments you genuinely cannot access on your own: institutional private equity funds, infrastructure investments, private credit, real estate partnerships. These are the tools that pension funds use—and they’re typically only available through advisors with specific institutional relationships and the background to fully understand the intricacies of these investments.
There is also a very wide range of quality of private assets. It’s like hockey leagues – there are Peewee/Bantam Managers, Major Junior Managers, and the NHL calibre managers. Don’t settle for lower quality managers, when best-of-breed is available. By quality, I’m referring to global reach, scale, long-term track record, and the firm’s talent.
Red flag: If your advisor only talks about publicly traded stocks, bonds, and mutual funds, they’re offering you a limited toolbox.
3. “What’s your investment philosophy when markets drop 30%?”
Anyone can look smart in a bull market. What matters is what happens when things get ugly—because they will, eventually.
You want to hear a coherent philosophy, not platitudes. “Stay the course” is not a philosophy. Neither is “we’ll reassess based on conditions.”
A good investment advisor has thought deeply about risk—how much you should take, how to structure a portfolio to weather downturns, and what circumstances would trigger changes. They should be able to explain this clearly without jargon.
4. “Who is your typical client, and why do you work with them?”
Advisors, like doctors, often have specialties. You want someone who genuinely understands your situation—not just financially, but professionally. An advisor who works primarily with dentists and physicians understands practice transitions, professional corporation structures, and the unique tax considerations you face. A generalist may not.
Red flag: “We work with everyone” often means they specialize in nothing.
5. “Can you walk me through a client situation similar to mine?”
This separates experienced investment advisors from those learning on your dime.
Ask them to describe — without revealing confidential details — how they helped someone in a similar situation. What was the challenge? What did they recommend? What was the outcome?
An experienced advisor will have multiple examples and will walk you through their thinking with specifics, even if names and numbers are changed.
Red flag: Vague answers, hypotheticals, or pivoting back to generic talking points.
The Conversation Behind the Questions
Here’s the thing: these questions aren’t about getting “right” answers. They’re about having a real conversation.
An advisor who welcomes these questions—who leans in rather than getting defensive—is showing you how they’ll behave when you have concerns down the road. The relationship you’re starting could last 20 or 30 years. You want someone who treats your questions as reasonable, not inconvenient.
And if an advisor can’t give you clear, direct answers to these five questions? They’ve given you all the information you need.
Click here to book your complimentary Discovery Call where Shamez will happily answer these questions and more!
Mount Columbia Private Wealth specializes in working with dentists, physicians, and business owners navigating major liquidity events. If you’d like to have this conversation with us—and see how we answer these questions—we’d welcome the opportunity.