Hiring Advisory Firm Employees For The Long Term: How To (Efficiently) Screen For The Right Culture Fit

Hiring a new employee is not a decision that firms take lightly. When new roles are created, hiring often represents a significant leap – temporarily reducing profit margins to make room for growth – not just for the new employee, but also to support increased capacity to bring on new clients, more hands on deck to split the current workload, and, hopefully, higher revenue. The firm owner (or hiring manager) must also craft the job description, interview and evaluate candidates, and create an onboarding plan, all of which take significant time that could otherwise be spent working more directly in the business.

Managers are also left to contemplate the balance between experience and compensation. A more experienced employee requires little handholding, but may require some level of 'untraining' as the manager must train them in the firm's way of doing things. A less experienced employee requires more training and context, but also presents a 'blank slate' to work with. Either way, the time and energy invested in training make it all the more important to ensure a good culture fit from the start.

A firm may go through multiple rounds of interviews, work samples, evaluations, negotiations, and may even begin onboarding… only to discover that – despite their chosen candidate being qualified on paper (or perhaps even in reality!) – there isn't actually a long-term fit. This could lead to a mutual parting of ways or a termination. In either case, it means the firm must start all over with its hiring process. Hiring and onboarding employees is expensive; continually bringing on new hires for the same role gets really expensive.

Perhaps that's why many advisors who have built and trained strong teams agree on the same point: "More than skill set, cultural fit matters." Evaluating for cultural fit, not just competency, during the hiring process helps firms find employees who will stay and thrive – without adding much extra time to the process itself.

What Is A Work Culture?

In the workplace, 'culture' can be defined as what it feels like to work somewhere. If the company's purpose is why employees do things, then the culture is how they show up each day. Workplace culture is often composed of several key dimensions – from the firm's shared values and expectations to how people communicate and collaborate – and each of these elements, as outlined below, shapes the overall experience of working there.

Policies: The routine expectations of the mundane day-to-day, ranging from expectations of when people show up to the firm's expectations of conduct and appearance. For example, are employees expected to be at their desk at 9:00 on the dot, or is there a flexible work schedule? Is the dress code formal, casual, or something in between? Do expectations change when clients visit? Is swearing allowed?

Values: Why does everyone show up to work each day? What is the end goal? Why do people do what they do, in the way that they do it?

Benefits: Given that the company has (some amount of) limited budget and time, how are company resources allocated to reflect those values? For example, one firm may offer their employees a wellness budget, and another may offer an education stipend.

Traditions: Traditions and rituals are a crucial element of belonging – and they may range from inexpensive, fun gestures such as an annual March Madness bracket, to more expensive, 'big budget' productions like a team retreat. The types of fun that resonate with the team – and especially recurring experiences that turn into ritual and tradition – are all crucial parts of the company culture.

Expressing appreciation and feedback: How does the company recognize good performance, and how is that appreciation expressed? Likewise, how is that feedback shared and received?

Encouraged traits and behaviors: Certain employee behaviors (and even personality traits) will naturally mesh better with the team than others and become implicitly or explicitly encouraged over time. This isn't about everyone being the same – in fact, homogeneity of background, personality, or thought can create blind spots and redundancies. However, a core set of values and ways of working are typically encouraged within the 'personality' of a company.

Unwelcome traits and behaviors: Philosopher Karl Popper's The Paradox of Tolerance proposes that some degree of intolerance is essential to maintain tolerance. Similarly, a healthy company culture requires setting clear boundaries around behaviors and attitudes that don't align with the company's values – such as discriminatory or disrespectful conduct – which can't be allowed to take root.

To some extent, culture is cultivated from the top-down by the company's leadership: they 'set the tone' with the values and perspectives they display at work, they determine which performance and personality factors (if any) are discussed in employee reviews, and they choose which potential benefits and perks are funded. Given that resources (time, energy, and financial benefits) are finite, each decision to emphasize one part of company culture can often mean de-emphasizing another.

While many components of the infrastructure of company culture are determined by leadership, employees eventually outnumber managers/owners in most firms. Which is why it's important to hire people who, at a minimum, generally align with and are willing to work within the company's cultural boundaries. Better yet, every firm benefits from natural company culture champions who promote and reinforce the firm's values organically. This dynamic — employees outnumbering leadership – is a part of why culture fit matters and why many managers describe a successful hire as someone who is not only competent at their work but also a genuine member of the team.

Why Culture Matters For Retention

Since company culture makes up the fabric of the day-to-day work environment, it plays an immense part in employee satisfaction and long-term retention. A healthy company culture is important to the firm at large, but an individual employee's fit within that culture is paramount to a long-term mutual fit.

According to Kitces Research on What Actually Contributes To Advisor Wellbeing, many of the components most strongly correlated with high wellbeing for advisors pertain to the culture of a workplace. Advisors who felt that they could be themselves at work were more than twice as likely to be "thriving" (self-reporting a nine or ten on a ten-point scale of wellbeing) than their struggling (defined as a score of five or less) peers. Likewise, advisors who had autonomy over their schedule, felt that their work had purpose, and felt effective at their job all reported higher levels of wellbeing.

All of these metrics are affected to some degree by the culture of a workplace – but when it comes to an employee feeling a cultural fit within their firm, most important are perhaps autonomy (the ability to structure one's schedule) and the comfort to show up as oneself at work.

Good cultural fits can yield good returns in the long run – a Gallup survey reported that employees who felt connected to their organization's culture were 47% less likely "to be watching for job opportunities or actively looking for another job."

All of this to say – a good work culture pays dividends. But it is also worth protecting and reinforcing the positive components of work culture at a company, and much of that comes down to who is hired in the first place. A successful new hire not only has a minimum level of competency, but also aligns with the firm's overall ethos.

Barriers To Assessing For Cultural Fit (As Well As Competence)

Most firms strive to hire good cultural fits; however, it's difficult to actually assess for cultural fit in an interview.

For example, a firm's interview process may include a 10-minute screening call, a 30-minute first-round interview, and a 45-minute final-round interview. That doesn't give the manager much time – a grand total of 85 minutes – to not only assess for competency but also get a feel for the candidate's personality and cultural fit.

Additionally, in an interview, both the firm and the candidate want to put their best faces forward to demonstrate mutual fit. Ideally, this means that everyone is honest… but polished. The candidate is trying to figure out how to spin questions like "What are your weaknesses?" into explanations of their strengths, and the company is trying to explain backfilling a role in a positive, change-oriented way. It's normal for everyone to make small adjustments to their responses to signal compatibility with the interviewer and the company (and vice versa). Which makes for a more pleasant conversation, but also makes it more difficult to gauge cultural fit and how a person will actually show up in the day-to-day.

Another potential barrier to hiring for cultural fit may be the urgency of the hire. Many advisory firms (particularly smaller firms) tend to wait as long as possible before hiring. This can be due to a possible combination of cash flow constraints, uncertainty about whether there's enough work to justify a new role, or logistical hurdles such as more complex compliance requirements for a larger team. Sometimes, by the time the firm is hiring, it can be tempting to throw cultural fit aside and 'only' screen for a person who can do the job (or sometimes, honestly, a person with a pulse!).

However, hiring for culture doesn't necessarily mean that the process has to be longer – though it may mean that the process itself needs to be changed.

Hiring for cultural fit as well as aptitude creates a double-filter, so to speak, on who ultimately fills the role: a candidate has to have both some degree of genuine competency and some level of genuine cultural fit with the firm. As long as a person has the aptitude for the role, they can learn practically anything the job entails (though some jobs may require more experience than others), but a personality fit is harder to fake – and still has a very real impact on team culture and retention.

The end goal is not to add an additional round of interviews to the interview process exclusively focused on culture – the goal is to give the manager (and firm) a defined list of what to look for while engaging with the process.

Defining Company Culture

A robust culture is crucial but intangible; unlike other Key Performance Indicators (KPIs) that can be measured on a spreadsheet, culture is inherently a little abstract. Likewise, a prospective hire's work experience can be measured to some degree just by looking at a resume; it is usually much harder to 'see' cultural fit.

In order to screen and hire for cultural fit, it is first important for the firm and its employees to be able to articulate and define the company's culture. As was discussed earlier, culture usually comprises some blend of policies, norms, benefits, traditions, communication styles, formal expressions of appreciation and feedback, and the traits and behaviors that are encouraged. Usually, the firm doesn't need to define more than three to five core elements of company culture (too many facets of company culture can dilute the focus and uniting features of culture, especially at smaller firms where resources only go so far!).

There are many facets to creating, explaining, and perpetuating company culture, but if the firm is really trying to articulate and crystallize its culture, here are a few questions that can help with getting started:

• What is one shared trait that all team members ideally share?
• What does camaraderie look like on this team?
• How does the company best support and invest in its team members?
• How should this team approach challenging situations and giving feedback?
• What are one or two words that would be used to describe this firm?

Alternatively, it may be easiest to start with a large list of cultural traits and then narrow it down. Consulting Brené Brown's list of emotions or asking ChatGPT or another LLM to generate a list of company values can make this task easier, as it can also help the advisor identify what the company culture is not. And of course, asking team members themselves to describe the day-to-day wins and opportunities is always a good way to generate a few descriptors of how company culture 'really' is.

It's also worth noting the parallels between hiring for cultural fit and prospecting for qualified leads. When a firm is prospecting for new clients, the number of 'qualified leads' – prospective clients who are in the 'right' financial or life circumstances, and who resonate with the firm's philosophy and approach – are more valuable than a random prospect that is likely to be screened out for lack of fit, or otherwise onboarded only to turn out to be difficult to work with. The same applies to hiring. Many applicants may be great employees in general, but not necessarily a personality fit at a specific advisory firm. Applicants often screen job descriptions for roles that seem like a good fit not just in terms of responsibilities and compensation, but also for culture and attitude. Broadcasting the firm's culture to potential applicants can help it screen for high-culture-fit candidates without adding additional work to their interview process. The firm's website and the content of the job description both provide opportunities to give those signals. It can be as simple as sharing photos of team get-togethers or writing a few sentences about what it's like to work at the firm:

• We look for people who embody [X].
• [X] is incredibly important at Firm, which is why our employees enjoy perks such as [benefits].
• At Firm, we celebrate achievements with [X].

Just a few sentences can go a long way in helping an applicant determine whether the company itself would be a good fit.

How To Assess For Culture Fit In An Interview

Just as company culture can be communicated with a few updates to what already exists on a website, cultural fit can be assessed by refining questions already asked in the interview process – without increasing screening time.

During interviews, aim to screen for three or four core values, evaluating one value per question. It's important to ask the same question or set of questions to each candidate for consistency's sake, which allows for a more meaningful comparison between candidates. Follow-up questions are helpful to explore what's discussed, but it's also important to be cognizant of the timing to keep the interview on track.

A 30-minute first-round interview could be structured as follows:

• Minute 0–2: Greetings and introductions. Explain what to expect in the interview and the next steps if they pass this round.
• Minute 2–10: Professional background (screening for competence and experience).
• Minute 10–14: Transition evaluations. Why this firm? Why transition now?
• Minute 14–22: 1–2 Cultural-fit questions with follow-up questions.
• Minute 22–28: Candidate questions.
• Minute 28–30: Interview conclusion. Thank the candidate, reiterate next steps, and note when they can expect to hear back from the firm.

In this sample format, equal amounts of time are dedicated to screening background and cultural fit, reflecting the equal importance of both competency and alignment with firm culture. Interviewers may, of course, adjust this structure depending on the role being filled. For example, if the candidate is coming directly from college, there may be less background to discuss – which allows the advisor to dig more deeply into the candidate's personality and cultural fit.

In the format above, there typically isn't time to ask more than two cultural-fit questions, as these tend to generate longer answers and merit follow-up discussion. In fact, follow-up questions are often crucial in order to get honest, insightful answers from candidates. These prompts don't have to be complex – simple prompts like "Interesting, tell me more about that", "What did you do next?", "How did that make you feel?", or "Why?" can help candidates keep talking and reveal more about how they think and communicate.

If a work sample is part of the hiring process, cultural fit can be evaluated there as well. Almost any work sample allows a manager to evaluate traits like timeliness and thoroughness, but layers can be added to see how candidates handle feedback, explain complex ideas, or navigate disagreements. This can be as simple as asking a candidate to draft an email that offers feedback or explains a difficult concept. The point isn't to evaluate whether the candidate matches the firm's 'voice', but rather whether they align with its style and values.

In the final interview, the advisor can delve deeper into one or two additional cultural-fit questions. If time and structure permit, it may be helpful to include the team members who would work most closely with the candidate as well. The ideal flow will vary based on the firm's core values, but in general, it's helpful to start with questions that reveal a candidate's work motivations and problem-solving skills.

A 45-minute final interview may be structured as follows:

• Minute 0–2: Greetings and introductions. Congratulate them on making it this far and discuss final steps.
• Minute 2–12: Debriefing on the work sample (if done).
• Minute 12–26: Final questions from the manager. Primarily focused on cultural fit, as well as any lingering questions.
• Minutes 26–40: Final questions from the candidate.
• Minutes 40–45: Interview conclusion and discussion of next steps.

This framework provides an approximate roadmap that gives both the firm and the candidate space to assess whether there's a genuine mutual fit before deciding whether to move forward.

Questions To Ask To Screen For Culture Fit

Below are some sample questions that can help advisors get a good feel for how candidates may show up within the firm's culture. Asking at least two in the first-round interview and two in the final round can often provide enough insight into a candidate's culture fit.

Selecting questions comes down to which cultural values are the most essential to screen for – advisors may decide to select from this list or come up with their own. The questions may also vary by role – for example, if hiring a client service associate, it may be crucial to focus on how candidates manage disagreements.

Some of these questions focus on hypothetical or ideal scenarios, whereas others focus on actual work history and experience. A mix of both may be useful, especially for time management's sake – storytelling questions may elicit more authentic insights into how people truly show up at work, but they can also prompt more detailed responses that require follow-up.

Questions Addressing Ethical Dilemmas And Conflict Resolution

• What's a difficult ethical dilemma you've faced at work? How did you solve it?
• Tell me about a time that you had a disagreement with a [coworker, manager, client].
• Tell me about a miscommunication with a [coworker, manager, client].

What to look for: It's informative in itself if a person can think of a conflict to discuss, especially one where they were in the wrong (which isn't necessary, but interesting to look for). Some candidates may need prompting – "And then what happened?" or "How did you resolve it?" – to get the entire story. Listen for how they actually navigated the conflict.

(Any of these questions work, but many people find it easier to recall stories about interpersonal conflict, such as disagreements with coworkers, than ethical dilemmas on the fly!)

Questions Addressing Learning Style

• How do you approach learning new skills?
• If you were asked to learn [subject matter related to firm], where would you start?
• Tell me a story about a time that you had to learn something on the job.

What to look for: Learning styles are important – and interesting! – but learning is ultimately a form of problem-solving. The candidate's response can reveal their work style – do they mention collaborating with others? Working independently? Seeking guidance or experimenting?

Questions Addressing Favorite Parts Of Work

• Tell me about your favorite work project. What made it special?
• What energizes you at work?
• What professional achievement are you proudest of?

What to look for: Pay attention to what the candidate describes. Did they most enjoy the teamwork and collaboration? Did they prefer solo projects? Were their biggest achievements tied to inventing a new process or improving an existing one? These responses can reveal what a candidate truly values in their work environment.

With all of these questions, nonverbal cues are as important as verbal responses. Noticing when a person lights up during their answers can also reveal what energizes them, while moments of hesitation or discomfort may signal where they feel less aligned with the firm's culture.

Best Practices On Asking Interview Questions Well

When interviewing for culture fit – and in general – a few best practices are worth keeping in mind:

First, try to have a second interviewer on the call if possible. This adds perspective and helps with time management. One person can focus on asking questions, while the other handles note-taking (if an AI notetaker isn't being used). That way, someone is always fully engaged in the conversation.

Second, explain the hiring roadmap clearly and follow through on any promised timelines or commitments. Remember, the candidate is also interviewing the firm.

Third, when asking questions, simply ask the question. It can be tempting to jump into examples or to keep talking, but try not to give any 'leads' on what the right response is and simply ask the candidate for their honest thoughts.

Finally, respond to questions and statements – especially vulnerable ones – with appreciation and other affirmative responses. It's easy to slip into 'analysis mode' during interviews, but don't forget to respond to what's actually being said. Expressing gratitude ("thank you for sharing that") encourages candidates to continue sharing and creates a more positive, trusting experience. Questions about personality and work culture can feel personal, so acknowledging that vulnerability helps maintain rapport.

After the interview, jot down key impressions while the conversation is fresh. Using a simple internal scoring system (e.g., 1–5 scales for both competency and cultural fit) can make it easier to recall details and compare candidates later.

---

Ultimately, there are very few 'wrong' answers to cultural-fit questions. The goal is to understand a person's work preferences and the kind of environment where they'll thrive. Assessing how a prospective employee fits into the firm's culture is a crucial part of the hiring process –and thankfully, it doesn't require extra steps or complexity. By asking thoughtful questions and knowing what to look for in those responses, advisors can increase the likelihood of hiring someone who meshes well with the company culture – and stays with the team for the long term!