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25 Questions to Ask When Interviewing Financial Advisors

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Choosing the right financial advisor is one of the most important decisions you will make. You will rely on that person’s expertise to ensure you don’t run out of money in retirement, your loved ones are taken care of in the event of a traumatic life event, and you’re able to build and preserve your wealth to achieve big life goals.

Who better than to opine on the important qualities to look for in a financial advisor than the people who speak with advisors all day, every day: the team at Planswell.

So, what should you be asking your financial advisor?

Let’s start by looking towards two familiar faces here at Planswell. Financial advisors Ermos Erotocritou, CFPⓇ, Planswell’s business and performance coach, and Andy Cosby, the most successful advisor in Planswell history. What do THEY want to know from advisors?


Andy wants to know how they get paid: “Is it fee-based or commissions and what does that compensation look like?” He would probe for conflicts of interest. We constantly remind consumers about the importance of insurance for unexpected life events, but do advisors put their money where their mouth is? “Do you have a succession plan? What does that look like?” Andy wouldn’t work with an advisor without one.

Ermos is more focused on qualifications and level of service; “Are they a Certified Financial Planner? What other credentials do they have?” Credentials are regulated, so there is a higher standard and expectation of quality. Ermos also wants to know about the average size of their clients. “You don’t want to be at the very bottom of their book, because you won’t be a priority for that advisor,” he said.

We put the same question to the rest of our team. The answers broadly fell into three categories: personal fit, philosophical, and logistical questions. 

Personal fit


“How would you convince me to do something that you think is in my best interest?” Craig, our Head of Engineering, wants to be sure they would advocate for his best interests, even if he wasn’t in agreement with them.

Nick on our sales team asks “Why did you get in the business?” He wants to know what motivates them. In a similar vein, Tony, also in sales, asks, “Are you concerned about the wellbeing of my family and me?” For Tony, this is a more important, deeper relationship than a simple transactional one.

Patty, responsible for our partner success at Planswell, asks “How similar are you to me? What are the similarities?” A big piece of the advisor-client relationship is comfort. Patty wants to ensure her advisor can relate to her and her situation.

Aaron, another account executive, asks, “Who manages your money and why?” In asking this question, he’s able to judge the advisor according to the traits the advisor values the most.

Scott, our co-founder and COO, digs deep with his question; “Tell me about the biggest client you ever lost.” He wants to see what kind of character and self-awareness the advisor brings to the table.




Abdullah, a product manager at Planswell, and Mwangi, an account executive, both want the advisor to expand on their views about financial planning. Abdullah asks, “What is the goal of financial planning?” Mwangi asks, “What is your investment philosophy?” An intellectual engagement with the process is important to both of them.

Lukasz, our Head of Sales, and Vanessa, on the sales team, both want to know about incentivization behind products and compensation. Vanessa asks, “Does your company promote certain products over others? Why?” Lukasz asks, “How are you incentivized to produce?” Both recommend ferreting out any potential conflicts of interest.

Daniel, an Account Executive at Planswell, asks an open-ended question, “What are your thoughts about fees and why do you charge what you do?” He wants to see critical engagement over management fees. “If I can do this cheaper through a robo-advisor, I want you to explain to me the value you bring,” he says.




Abdullah and Pat, a sales manager at Planswell, are concerned about the frequency and type of communication. “How often should I expect to speak with you?” asks Abdullah. “What type of communication and cadence should I expect?” Pat asks. Attention to detail is particularly important to Pat, while Abdullah wants an introspective advisor; “What are your limitations in helping me through the process?”

Corey, an account executive on the team, wants to know how many clients the advisor has. “I don’t want to be just another number.” Neima from sales, meanwhile, is more concerned with investment performance; “What are your average returns? Do you achieve them consistently?” For him, it’s important the advisor is mitigating risk and achieving some measure of consistent performance.

Jen, our Chief Marketing Officer, has 2 main questions; “How much experience do you have?” and “What is your service offering?” Your advisor’s strengths should match up with your financial goals.

Aditya, our resident wunderkind, and Mark, an account executive, wanted advisors to sell their personal value proposition. Aditya asked, “What differentiates you from other financial advisors?” It’s a simple question, but particularly relevant in a competitive marketplace. Meanwhile, Mark asked, “Why should I go with you? Why not a robo-advisor?” After all, robo-advisors significantly reduce management fees.

So there you have it– by no means an exhaustive list– but a strong starting point in your search for an advisor. Ready to take the next step? Get a financial plan in under five minutes, then speak with one of our qualified advisors to walk you through it—completely free. Cheers to a secure future!