First, understand yourself, then ask these 25 interview questions.

(2-minute, 30-second read)

The reevaluation of personal and organizational priorities that is redefining how we work has caused a lot of movement in the job market. This wholesale shift is a primary contributor to the phenomenon called The Great Resignation.

As a result, employers are working hard to retain top and high potential staff. Concurrently, workers seeking flexibility, mission connection and an environment where they can meaningfully contribute are scrutinizing organizational practices and behaviors.

On the most basic level, both organizations and workers are looking for the right fit.

Finding the right fit is hard work. It begins with understanding what fit means to you, then observing and asking the right questions of a potential employer. Don’t expect the employer to do this work for you. If you are thinking about or in the process of changing jobs, you need to understand yourself before looking for opportunities. Here are five directional prompts that can help.

  1. How I define the ideal relationship between work and life
  2. My values and the way I act every day to live those values
  3. How I communicate most effectively
  4. How I define diversity, equity, inclusion, and belonging in the workplace
  5. How I like to give back (giving back has been proven to increase overall well-being)

Some answers may come quickly. Others may require more thought or discussion with trusted friends, colleagues and advisors. Your answers provide valuable information for your job search.


When speaking with a potential employer, you’ll want to ask pointed questions to evaluate if the opportunity presents a good fit.

Here are 25 fit questions to help you better understand an organization.

  1. What are the factors that contribute to ‘fit’ for this organization?
  2. What are three things you’ve learned from exit interviews over the past year?
  3. How has the organization addressed those gaps?
  4. What is the access to senior leadership?
  5. Is there an agreed-upon mechanism for organizational/departmental decision-making?
  6. How are the organization’s values implemented in daily practice?
  7. How is DEIAB defined and practiced daily?
  8. What are the areas of the organization’s culture that need improving?
  9. Is real-time feedback practiced and accepted at every level?
  10. What is the performance review process?
  11. Are behavioral goals measured in performance reviews?
  12. Does the organization have Employee Resource Groups (ERG’s)? If so, how do they operate?
  13. Is there a mentoring program? How is it structured?
  14. Are there opportunities to give back?
  15.  Is “job crafting” an accepted practice?
  16. Are there reskilling/upskilling opportunities available?
  17. How are middle managers supported?
  18. How are wellness and self-care viewed?
  19. What are five words you would use to describe my supervisor? (Or, five words to describe yourself?)
  20. Does the organization periodically assess psychological safety?
  21. Does the organization periodically assess burnout?
  22. When was the last employee engagement survey? What were the learnings? How were the learnings implemented?
  23. How does the team socialize?
  24. What is the average tenure of an employee at my level? What is the main reason for them leaving?
  25. What are your behavioral and communications expectations of me? How are these assessed?

Asking questions like these provides insight into an organization’s daily life. Supplement your interview questions with additional due diligence. Network your way in by connecting with employees and starting conversations on LinkedIn. Factor in reviews from Glass Door as a directional tool. Research press coverage and read remarks made by senior leadership at investor meetings and conferences.

Even in a job seekers-driven market, looking for a new job can be challenging.  With some extra work and a little advanced planning, you can improve your chances of finding the “Right Fit.”



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