top of page

Interview Your Next Employer

Updated: Mar 3

During my junior year of college, I wanted to explore a possible career in the wealth management field. When I was offered an internship at the first place I applied, I quickly accepted the position without giving the details of the role much thought. However, within the first few days, I realized I had made a poor decision. I thought I would be learning about investment strategies and sitting in on client meetings, but I spent almost all of my time leading the effort to move to a paperless office. Yes, I spent hours upon hours scanning boxes and boxes of financial documents.

Among the many lessons I learned from this experience, the one I most often share with others is the importance of interviewing prospective employers before accepting a job offer.

Questions I Should Have Asked

During the interview for my internship, I didn’t ask effective questions. I was primarily thinking about securing the internship to meet my graduation requirements, and I focused on surface-level considerations like pay and location rather than role expectations, company culture, and learning opportunities.

In hindsight, I should have asked some of the following questions:

  • What will my day-to-day responsibilities be?

  • How many client meetings do you anticipate I will be able to sit in on each week?

  • What opportunities will there be to learn about investment strategies?

  • What types of projects have past interns worked on?

  • How much time is typically devoted to administrative tasks versus wealth management activities?

Questions You Can Ask

Asking your prospective employer questions during the interview process can help you make a more informed decision about whether the position you are interviewing for aligns with your work preferences and career goals. Consider asking questions that will yield insights into different facets of the job and company.

Role Clarity

  • Can you walk me through the typical day-to-day responsibilities for this role?

  • Can you describe a typical day or week for an associate at this firm?

  • What percentage of an associate’s time is typically spent on administrative tasks versus core investment activities?

  • What opportunities are there for analysts to be involved in tasks like property valuation or client presentations?

  • How are deals typically sourced and evaluated, and what is the role of an associate in this process?

Team Dynamics

  • How is the team structured and how often do junior and senior analysts collaborate?

  • Can you describe a recent deal that required significant team collaboration? What was the role of junior and senior team members in its success?

Culture Fit

  • What is the office culture like? Would you describe it as competitive or collaborative?

  • How would you describe the firm’s culture, particularly around teamwork?

Career Progression

  • Could you describe the company’s approach to professional development for entry-level positions?

  • What kind of mentorship and growth opportunities does the firm offer for analysts?

Performance Metrics

  • What are the key performance indicators for this role?

  • How is success defined and measured for this position?

  • Can you describe the evaluation process for this role? Are there any key benchmarks or objectives I should be aware of?

Navigate the Nuances of Asking Tough Questions

Asking questions shows you have a genuine interest in the position; however, I recognize that some of you may still be hesitant to try to get a prospective employer to share a realistic job preview. Let’s unpack a few of the nuances to asking tough questions.

Timing: Save the more challenging questions for later in the interview process, once you have passed the initial screening.

Phrasing: How you ask the question can be as important as what you ask. For example, instead of asking, “Do people usually work long hours and weekends here?” you might ask, “Could you describe the company’s approach to work-life balance?”

Culture: Pay attention to the culture of the company. A more transparent and progressive culture often welcomes tough questions as a sign of a thoughtful potential employee. On the other hand, tough questions in hierarchical or traditional cultures might not be as well-received.

Quality of the Employer: High-quality employers will typically welcome well-thought-out questions. They appreciate that you want to make sure the role is the right fit for you because an unhappy or disengaged employee isn’t good for anyone. If an employer reacts negatively to reasonable questions, that could be a warning sign about their culture or the role itself.

Your Leverage: If you’re a highly sought-after candidate, you naturally have more latitude to ask tough questions than if you’re applying for an entry-level role in a highly competitive field.

Context: Potential employers, depending upon the industry and role they are seeking to fill, may expect candidates to ask detailed questions as part of evaluating their professional suitability and acumen. Not asking tough questions could be perceived as a lack of due diligence or genuine interest on your part.

Consider starting with safer topics to gauge reactions before moving on to more sensitive topics. You can also save some questions for after an initial offer has been made.

Monitor Your Mindset

The mindset between a candidate who is merely searching for a job versus one who is looking for a job that is a good fit for both themselves and their future employer can differ significantly. Both approaches are based on different underlying motivations, and they often lead to different outcomes.

Immediate Gratification Mindset

Strategic Alignment Mindset


Secure employment as quickly as possible, often due to financial necessity or pressure to transition out of unemployment or a less desirable job situation.

Find a position that aligns with individual skills, career goals, values, and lifestyle, as well as a company where you can contribute effectively.


Focus on salary, location, and title.

Consider a more holistic set of factors, including team dynamics, role responsibilities, company mission and values


Questions may be limited, or geared more towards what you think will secure a job, rather than deeply assessing whether the role is a good fit.

Questions are well-thought-out and are aimed at assessing both what you can offer and what you can gain.


Job acceptance is often quick if an offer is extended, without taking adequate time to consider if this is the best long-term move.

More time and thought go into the decision to accept a job offer, leading to a higher likelihood of a successful, longer-term employment relationship.


Higher likelihood of ending up in a job that isn't fulfilling or where there's a mismatch in expectations, which could lead to job dissatisfaction, poorer performance, and a shorter tenure.

The process may take longer and be more involved, possibly leading to moments of doubt or impatience, but the eventual outcome is often more satisfying.

Recognize the sense of urgency you may be feeling in the job search, and ask yourself if it might lead you to compromise on a less-than-ideal position. Instead, focus on the long-term, and consider how the opportunity fits into your broader life goals and professional development.


Interested in exploring this idea further? Watch this eCornell Keynote.

Recent Posts

See All


Commenting has been turned off.
bottom of page