This is a question I tend to ask toward the end of the first in-person interview, so that I can learn more about a candidate’s personality and interests, as well as gauge their desire for public speaking. It often gets the candidate to loosen up, think a little more creatively about follow-up questions and lets them know that we value more than just their ability to fit the technical job description.

Typically, interviewers want to know what candidates don’t like about their current roles. However, by asking the candidate what they do like, I begin the conversation on a positive note, and I quickly gain clarity on their professional outlook. This question also offers the candidate an opportunity to reflect on what they value in their work life in order to do more of what they enjoy most.

If I’m ever on the fence about a candidate, I like to ask this challenging question. If the candidate panics, I know that they are missing at least one essential quality for being a good financial planner. Whether it’s the ability to pivot, solve problems creatively or (at least) remain cool under pressure, I know something’s missing and I can confidently move on to other candidates. The worst response I ever got to this question was a very long pause, followed by the answer “black” with no explanation. The best response I can remember was a candidate who, without a moment’s hesitation, responded, “green, because green represents growth.” I’m sure there was more to the explanation, but what really sticks in my memory was the confidence with which the answer was delivered.

Here’s the setup I use before I ask this question: I say, “You are sitting with a potential client in a conference room, and you are either conducting an initial discovery interview or presenting a proposal. Assuming you and the client are both animals—any animal in the animal kingdom—what animal will that prospect see you as and why?” The question tests the ability of candidates to think on their feet, reveals how they visualize themselves and want others to see them, and shows their ability to articulate a position.

Everyone who invests has lost money. I don’t technically care what the losing investment was. I am looking for the candidate to build on why they invested, how it went wrong and, most importantly, what they learned. If they can talk about how the poor investment informed their research process going forward, so much the better.

This question strikes at the most important skills needed to be an effective advisor. First, most questions advisors get asked, like this one, don’t have a straight answer. This question forces the candidate to think on the fly and gives a glimpse of how they might think and react under pressure. The best candidates start by asking questions like: “Who is the sandwich for? Are there any allergies? What time of the year is it?”

Second, the sandwich question provides insight into the candidate’s passion. Does the candidate get excited about their sandwich? Do I see energy and creativity in their description? Clients need to see that their advisor has passion for what he/she does. 

At the end of each interview, I always try to ask about a hobby or outside interest the candidate lists on their resume. On one memorable occasion, I interviewed a young woman who was already an advisor at another firm. She listed “lounge singer” as an interest. I asked her why she chose to put this interest on her resume for a financial advisor job. She responded with a question of her own. “Do you know how challenging it can be to win over a room of people who have been drinking and are carrying on loud conversations? A lounge singer has less than a minute to either engage their attention or lose them. This experience has taught me how to better prospect for new business.” We hired her.

I like to ask this question to see how accurately candidates can “read people,” starting with themselves. If the candidate’s description is completely different from my interpretation of their nonverbal communication, then that tells me that either the candidate is saying only things they think I want to hear or that the candidate needs to improve on reading their own nonverbal cues.

The ideal answer needs to have a strong leaning on customer service. Something like: “Sir, the advisor is out of the office. Can I offer you a cup of coffee? We have warm chocolate chip cookies. Please tell me what is going on so I can help.” Finally, I want the candidate to take ownership of the follow-up, something to the effect of “Sir, I will personally make sure that the advisor responds to you. Can I schedule an appointment now?” The response I’m looking for definitely is not about how asset allocation works or that a 6% return is not bad.

Most technical knowledge can be taught. Politeness and empathy are harder to impart. One candidate stated that he would be upset, too, because it is an advisor’s job to beat the market. I terminated the interview right after this response. 

This question may sound tough, but it can be very revealing. There are two parts to it. First, I always read the candidate’s resume with a fine-tooth comb and try to find one error or inconsistency, either in spelling, grammar, punctuation or formatting. During the interview, I ask about that one (hopefully there is only one!) imperfection. It is not the misstep that I am concerned about. I am gauging how the candidate deals with constructive criticism. Do they laugh it off? Do they argue? Are they deflated? What is their reaction? I have had candidates heatedly argue with me about spelling. To me, that doesn’t predict a great fit. 

The next part is just as important. I immediately follow up the candidate’s response by asking, “What review process did you take when preparing your resume?” Here, I am trying to understand how seriously they took the resume preparation process. If they failed to put serious time and thought into what may be the most important document in their careers to date, what level of commitment and professionalism can I expect them to display in their potential new role?

This is one of my favorite questions for candidates applying for a sales position. It has been my experience that if you are hiring a salesperson and they are not motivated by money they will rarely excel to a high level. The most successful salespeople I know are highly motivated by money. If you dangle a carrot, you better get out of their way, as they will be going for it. I want to see the desire in their eyes. The best salespeople know that their ability to create wealth for the company will lead to them creating wealth for their families. This is a very desirable alignment.