How To Interview (For a Financial Planning Job)

In the past, we’ve written after every hiring cycle to review the overall metrics and methods by which we measure and recruit for the career opportunities at MY Wealth Planners. As we’ve officially completed our interview cycle, we now look to do the same for our most recent Wealth Planning Analyst hire. However, this time, rather than repeating our normal report on the places we posted positions, the number of applicants we received, how many made it to the second step of the process, and so on, we thought we would discuss the interview phase of the recruiting process. What we ask and why, what answers work, and perhaps even more importantly, those that don’t.

Interview Questions

When structuring the interview, we’ve paid very close attention to a couple of particular factors:

• Giving the candidate the opportunity to demonstrate their character and personality in a dynamic medium.
• Avoiding typical questions, e.g., “What is your biggest weakness?”
• Providing a mix of questions that offer an opportunity for the candidate to demonstrate technical knowledge, emotional intelligence, and interpersonal skills “on the spot” as financial planners are often asked to do by their clients.
• Opening up the interview as a chance to have a discussion about the opportunity, the firm, or anything else the candidate would like to know about the position.

By the time the candidate has reached the interview, they’ve already submitted a qualified and satisfactory resume and cover letter, demonstrated attention to detail by including pertinent “AI-proofs” in their cover letter, and had the opportunity to present themselves professionally in a 5 minute video submission that asks them to tell us about them, why they want to work with us, and presents an open-book technical case study question. So, when they come to the interview, they’ve already demonstrated basic professionalism, ability to research, communicate, and problem-solve when given ample time.

With this in mind, our most recent interview round had 15 questions and typically took about 30 minutes:

1. How have you been preparing for this interview?
2. We’re going to ask you a few questions, but we’re going to eliminate the most common answer we get from consideration. So, the first question is: Other than “because I want to help people,” why do you want to be a financial planner?
3. Understanding that the core reason we all work is fundamentally to make a living, why are you interested in this position with MY Wealth Planners specifically?
4. Tell us about your experience with financial planning technology. What tools or programs have you used?
5. Which tool is your favorite and why?
6. Geography Question:
   • If Local: Why do you want to work and possibly live in Longmont? It’s a lovely town, but aren’t you interested in living somewhere else?
   • If Not-Local: You live in [X] today. Why pick up your life to take a job in Colorado?
7. We have a two-part question for you: 1) What is the most complex financial problem you’ve helped someone else solve, and 2) How did you solve their problem and what did you learn from it?
8. Let’s role-play a hypothetical: A client would like to retire by the end of this year. Based on your plan and analysis, they do not have adequate funds to support themselves going into retirement if their plan is to live solely on their savings. Speaking to me as if I’m the client, please take a minute to demonstrate how you might explain that issue and propose a solution or solutions.
9. This position starts on [Date]. Can you talk to us about that timeline and if or how that works for you?
10. What is your ultimate career ambition? By the time you’re ready to retire from professional life, what do you hope you will have accomplished?
11. We want to take a moment to describe the position’s responsibilities: [Description of the role.] Do you have questions about those responsibilities or what a day in the life is like?
12. Having had the opportunity to review the benefits guide, which includes a lot of information on our career path for financial planners, can you tell me your personal objectives over the first three years with the firm?
13. In the video you made for us… [referencing the case study in their 5-minute video submission at the 2^nd stage of the application process, we provide a modification to the circumstances from the case study that should impact their recommendations or approach to that problem.]
14. We’ve spent a good bit of time putting you on the spot, asking you questions. So, let’s reverse roles for a few minutes. What questions do you have for us about the position, the firm, or anything else?
15. We’ve had quite a few applications, but that said, we’re only interviewing a handful of people. So, in your own words, what makes you the best choice for this position compared to all the other great folks who have applied?

There Are No “Right” Answers

Notably, there are no “right” answers to the questions above. Each individual applicant can have fair and valid differences in their perspective, opinion, and approach to the questions being asked. That said, there are styles to answers that are going to stand out better than others. Herein, the framework of “signaling theory” is helpful because it presents the key mechanism at work in the process of an interview. The interviewer is asking questions that provide key signals to the applicant about what the firm thinks is important for the applicant to demonstrate, and in turn, the applicant answers questions in a manner that they hope will signal competence and suitability for the role they’ve applied for. Notably, then, there are three gradients of signal that an interviewee can give their interviewer: A positive signal, a non-signal, and a negative signal.

A positive signal indicates the applicant is demonstrating the key competency that the question is aimed at elucidating. In some cases, such as the questions 4 & 5 about their experience with financial planning tools and their favorites, the signal is fairly straightforward. Naming relevant and useful technology they’re likely to use in their role as a financial planner, or otherwise naming related tools, indicates that they have experience with the appropriate types of technology.

A non-signal isn’t inherently negative, but it’s not scoring the interviewee any points. Here is where something like a simplistic but appropriate answer can come into an interview. Take question 1 (“how did you prepare?”) or question 12 (“objectives over the next three years”) come into play. If your preparation is simply “I read the job post, looked at your website, reviewed the benefits guide,” then that’s not a negative answer, but it’s also not a positive answer. That answer is a demonstration of basic due diligence you should engage in when applying to any job. But if the answer instead relates specific details about your due diligence, such as referring to specific blogs or podcast episodes, bringing up details not shared in the job post but that are relevant things related to the business (regulatory details, the firm’s certified B Corp status, etc.) then that shows that you did you research but also took away something from that research, which is a demonstration of competency. If your answer to “objectives over the next three years” is essentially “do the job,” that’s not a bad answer, but it’s also not a helpful or differentiating answer. It’s meaningful to be able to articulate both personal and professional goals when asked.

Non-signals can also show up in lackluster questions. Typically, an interview will offer the candidate one or two opportunities to ask their own questions (questions 11 and 14, for example). When presented with this opportunity, saying “I have no questions”, asking questions answered already by the interview itself or in the job posting, or otherwise asking questions that are unrelated to the subject, can be non-signals. The reason for this is that a well-articulated and thoughtful question about a position, the firm, or the work thereof can demonstrate curiosity and attentiveness to detail. For example, asking about the nuances of a specific benefit that’s offered or how the firm engages in community service or philanthropic activities (and citing relevant examples!) can be positive signals rather than non-signals.

Then, there are negative signals, which are “red flag” answers that suggest the candidate is either ill-suited to the position or otherwise lacks core competencies for the role. Those, we’ll discuss in greater detail.

Non-Verbal Negative Signals

Negative signals are the proverbial “oil in water.” They can be moderately harmful to the interviewee’s chance of success or outright disqualifying. Negative signals can be verbal and non-verbal. While we’ll provide a few specific examples of negative signal answers to our sample questions above, let’s discuss first some negative signals in how an interviewee presents and conducts themselves.

First is an interview-appropriate presentation. There is simply never a reason to show up to an interview in anything less than business professional attire, professionally groomed, and with appropriate makeup, jewelry, or other accouterments you feel are appropriate for you as an individual. You cannot overdress for an interview, but you can certainly underdress for an interview. Examples we’re about to share are those we’ve seen in our interviews in the past, but are certainly not exhaustive.

Negative signals in the attire of male-presenting applicants can include the lack of a suit or shirt and tie combination, messy or unkempt hair or facial hair (beards are fine, 3 days of stubble is not), and unpolished dress shoes or street shoes. Many male applicants will dress professionally, but forget that their professional presentation is more than putting on nice clothes, and otherwise present as someone who rolled out of bed, threw on a dress shirt, and went to their interview.

Negative signals in the attire of female-presenting candidates can include excessive makeup or jewelry, overuse of perfume, and what we’ll describe as “over-layering,” that is to say, showing up in a coat over a sweater over a blazer over a blouse over a top, resulting in a strangely puffy visual effect. If the weather is appropriately cold, such attire can make practical sense, but removing layers at reception or upon entering the building is an appropriate step to take to appear professional rather than “puffy” by the time of the interview. It’s also recognizable that women’s fashion around what constitutes professional can also be more subjective than for men; where men simply elect to wear a suit and tie, women are often presented with suits, jumpsuits, dresses, or combinations of attire as potential options. Herein, reviewing the firm’s headshots can be a signal of what’s typical within the work environment and thus appropriate to emulate.

Finally, for both male and female-presenting candidates, there is the issue of accessories with attire. Many candidates will bring a notepad or folio with their resume, pen, and paper with notes or questions. This is perfectly fine. Other candidates may bring a purse, clutch, and/or water bottle. What you elect to bring with you is less important than how much you elect to bring with you. It is advisable that you try to keep to no more than two “carried items”, particularly in consideration that you will likely be shaking hands. Some candidates attend interviews with enough accouterments to cover half the conference room table, and squander precious time “getting organized” at the outset of the interview. Thus, when it comes to what you bring with you, less is more. We recommend limiting it to the aforementioned notepad and folio with resume and work samples as needed, and a purse if needed. Your interview is unlikely to last so long that you need to bring a Stanley thermos or an Owala water bottle to survive.

Moving beyond attire, there is then the potential of negative signals in professional conduct. Your interview begins before you arrive at the interview. Do you arrive early, e.g., 3-5 minutes before your appointment time, or are you walking in the door at your interview time? If the interview is on Zoom, have you checked your audio and video settings and ensured your environment is quiet and your background is private? When you enter the reception, do you make polite and warm conversation with the person or people in reception, or do you immediately bury your head in your phone? These are indications of planning and preparation, and opportunities to demonstrate interpersonal skills. In turn, when you are invited into the space to interview, do you take the time to acknowledge and interact with everyone you meet or are introduced to? We recommend it. An immediate negative signal for us in interviewing candidates is their timeliness to the interview, whether they communicate well with our staff in the reception, and whether they politely and professionally acknowledge and introduce themselves to each team member they encounter. Treating staff “as staff” rather than as potential colleagues is a natural red flag, because as we’ve seen both in applicants and in potential clients, how folks tend to treat you at the beginning is often a strong signal of how they’ll treat you later.

Verbal Negative Signals

Herein, we get to the point of how you’re actually speaking, communicating, and the answers you provide during the interview. As noted earlier, there are plenty of positive ways to answer questions and plenty of ways that don’t really tilt things one way or the other. Here, we’re focusing on both poor means of communication and bad answers to specific questions.

There is a basic set of guidelines for how you convey strong communication as a candidate for a role as a financial planner.

1. If there are multiple parties in the interview (e.g., multiple interviewers), be certain you are speaking to whoever has asked you the question, but then also take the time to address the other people in the interview. Do not speak solely to one person for the entire interview unless you have a solo interviewer.
2. Speak up a bit. A lot of people are naturally soft spoken, but that can deprive their voice of the range to express emotional variation or changes in tone.
3. Be mindful of your “patterns.” Everyone has a certain set of phrases they will fall back on naturally during a conversation, but sometimes practice can become a handicap. Examples of this can be “That’s a great question” as the response to every single question before actually answering the question, which eventually becomes noticeable and annoying.
4. Be comfortable with silence. Many people mistake listening for waiting for their turn to speak in an interview, and no sooner than the interviewer is done speaking, they immediately leap to answer the question. While this can be a natural response to hearing a question you’re very well prepared for, it can inadvertently indicate that you’re answering “a question” and not “the question.”
5. With item #4 in mind, answer the question you’re asked. Some people like to give a lot of context before answering the question, but this can create the impression that you’re stalling for time or otherwise trying to avoid the question. Worse, you can end up spending so much time on that context that you never actually answer the question! A better pattern is to directly answer a question you’re asked and then provide additional flavor or context to your answer if or as appropriate.
6. “Yes” and “no” are insufficient answers on their own. You can always say yes or no with a clarifying repetition of the question that was asked. “Yes, that start date works for me.” “No, I do not have any bankruptcies, liens, or criminal history to disclose.”

Ultimately, the guideline in communicating your answers as a candidate for a financial planning role is that you need to demonstrate the same competencies you’ll need with clients. Are you thoughtfully listening to your audience when they tell you things or ask questions? Are you responding clearly to their questions? Are you demonstrating active listening and a subsequent appropriate emotional response to the nature of what they’re saying? Failing to demonstrate these behaviors will result in a lackluster connection with your audience.

Then there are simply bad answers. We could fill an entire blog with the bad answers we’ve gotten to the specific questions we ask in interviews, so we’ll try to keep it more succinct here with a couple of specific combinations we’ve seen over time.

We’re going to ask you a few questions, but we’re going to eliminate the most common answer we get from consideration. So, the first question is: Other than “because I want to help people,” why do you want to be a financial planner?

“Because I want to help people.” We know that’s the core reason many people want to become financial planners, and we applaud it. But when the question specifically eliminates that answer as a viable answer, trying to force it through anyway betrays that you’re not actually thinking about the question beyond what you’ve already prepared. The problem with the answer itself, no matter how true it may be, is that you can help people in lots of ways. Volunteer your time, be a teacher, go into healthcare, work at a non-profit, etc. So the answer of “to help people” is naturally insufficient because the question is why you want to be a financial planner, and therefore, the question, by extension of the restriction of the “help people” answer, is “why do you want to help people by being a financial planner?”

Tell us about your experience with financial planning technology. What tools or programs have you used? Which is your favorite and why?

This is actually an easy question, whether you’ve used financial planning tools or not. If you’ve used financial planning tools, then you simply list off the applications you’ve used and speak honestly about which one you like the most. If you haven’t used a financial planning-specific tool, you can still pivot to something like Excel that you may have used in other jobs or in classes, and discuss the functionality it provides. We’ve had candidates offer everything from Microsoft Word to Python coding; there is no wrong answer here, only an opportunity to share your earnest experience and convey enthusiasm for what you’ve already done in your work. Failure to share your experience or express any joy for it raises a concern.

We have a two-part question for you: 1) What is the most complex financial problem you’ve helped someone else solve, and 2) How did you solve their problem and what did you learn from it?

There are a couple of mistakes people can make here. First, many candidates answer the question about themselves rather than about how they’ve helped someone else. This is both an issue of attention to detail and also elicits a question about their experience. Financial planners aren’t solely their own financial planner, but professionals who help others with financial problems. If you’ve never so much as offered someone else advice about their budget, paying off a credit card, or picking an investment, how are you going to do it for a living?

The second part of the answer is more important because it offers an opportunity to demonstrate professional judgment. Is the solution the interviewee provided actually a solution to the problem? A positive signal is a clear solution that solves a problem. A non-signal is something generic about educating people or otherwise talking to them about the resolution. A negative signal is advice that was harmful; we’ve ever had a candidate with professional financial advisor experience describe literal malpractice as their answer before. Big red flag!

Let’s role-play a hypothetical: A client would like to retire by the end of this year. Based on your plan and analysis, they do not have adequate funds to support themselves going into retirement if their plan is to live solely on their savings. Speaking to me as if I’m the client, please take a minute to demonstrate how you might explain that issue and propose a solution or solutions.

With any case study or role-playing question, you need to differentiate between whether this is a technical skill demonstration or an emotional intelligence and soft skill demonstration. In this example, there is no technical data whatsoever, simply an acknowledgment that this individual client is not able to retire yet. Positive signals include questions that probe their intention to retire this year, demonstrate empathy and sympathy for the frustration that can arise as part of not being able to work longer, and then bring up examples of alternative approaches, such as reducing expenses or probing into the reason they want to retire so soon. Negative signals include immediately leaping to blunt delivery of bad news, or subsequently launching into ultra-specific “here’s what you’re gonna do” types of recommendations, rather than explaining and educating around the alternatives available.

What is your ultimate career ambition? By the time you’re ready to retire from professional life, what do you hope you will have accomplished?

Herein, there is no wrong answer except a lack of an answer. While it’s certainly a positive signal if your career ambition is to become a partner at MY Wealth Planners, there’s nothing wrong with expressing interest in building generational wealth for your family, having a major impact on a community or non-profit, or otherwise expressing that you’re really in financial planning to pay the bills while you work on your career as the next great Cello player. A lack of an answer, or one that’s so general as to be uninformative, is problematic because financial planning is a profession built around the idea of helping people live their great lives. If you have no imagination for your own great life, how will you help others build theirs?

We’ve spent a good bit of time putting you on the spot, asking you questions. So, let’s reverse roles for a few minutes. What questions do you have for us about the position, the firm, or anything else?

We’ve touched on this in past articles before, but good questions for the firm are going to include clarifications of nuances around job role, timeline, or compensation, rather than general “do you have a 401(k)” type of questions. It’s also a meaningful opportunity to dig into the firm’s vision, mission, or the view they have of their growth and future. Some people, unfortunately, do squander this time, asking for things like “What’s your favorite Lord of the Rings movie?” (The Two Towers) or asking the founder of the firm, “Why do you like working here?” (Because it’s my business, duh.) Ultimately, this is an important time to either round out clarifications you need to decide on whether you want to work here, and in the absence of such questions, to build rapport by demonstrating through your questions that you’ve done your research on the opportunity.

We’ve had quite a few applications, but that said, we’re only interviewing a handful of people. So, in your own words, what makes you the best choice for this position compared to all the other great folks who have applied?

You tell us what your great answer is. But negative signals are going to include a generic “I’ll work hard” or “it would be a great opportunity for me.” We expect those things. The question at hand is one about differentiation: You’re great, everyone else interviewing is great, but why are you the best?

Interviewing is Hard

It’s just a fact. But we like the perspective of our colleague Daniel Stefanski on this issue: Control the things you can control. You can’t expect every question you’ll be asked, and you can’t always know you’re going to give the perfect answer. But you can meaningfully prepare, practice answers to common questions, and otherwise put forth an effort so that you show up as well as possible when the time comes to assess whether you’re the right fit for the opportunity, particularly compared to all the other great people who’ve applied. Remember, an average effort gets an average result, and the average result of a job application is that you don’t get the job.