Six questions worth sitting with.
These aren't gotchas. They're the questions most people never think to ask — until something goes wrong.
Question 01
Do you know, precisely, how your advisor is compensated — and by whom?
There is a difference between fee-only and fee-based compensation models. Understanding how your advisor is compensated — and when different standards apply — is important. If you're not sure which model applies to your relationship, that's worth knowing.
Question 02
Is your advisor a fiduciary — in every situation, not just some of them?
Different regulatory standards apply depending on the advisory relationship and the type of product or service involved. Understanding which standard governs your relationship — and when it applies — matters.
Question 03
Does your advisor specialize in situations like yours — or are you one of several hundred clients?
Advisors with large client bases may structure their service models differently than boutique practices. More importantly, a generalist may not have focused experience with your specific complexity — a business sale, equity compensation, a divorce, multi-state real estate, a compressed tax window. Credentials matter. Practice focus matters too.
Question 04
When did your advisor last bring something to you — rather than wait for you to ask?
Proactive advice is the difference between a financial advisor and a financial order-taker. Tax law changes. Life changes. Markets change. If your advisor's outreach is limited to quarterly reviews and annual check-ins, consider whether that structure aligns with your expectations.
Question 05
Has your advisor ever told you something you didn't want to hear?
The best advisors earn their fees in uncomfortable conversations — telling a client their spending trajectory is unsustainable, that a business valuation is unrealistic, that the estate structure doesn't match the intent. If every conversation has been comfortable, ask yourself whether your advisor is optimizing for your outcomes or for the relationship.
Question 06
How did your advisor find you — and does that process tell you anything?
Most consumers end up with their advisor through a referral, a cold call, a seminar, or a lead platform that routed them based on zip code and asset range. Many consumers are connected based on geography or asset range rather than specialization and verified credentials. That's not an indictment of your advisor. It's a description of how the industry works — and why most people have never experienced a structured, credential-verified introduction.