64 Questions I Wish I Asked Before Accepting My New Job

Job satisfaction. What makes someone happy with their job? I recently interviewed someone regarding this very situation. They recently accepted a new job and were in search of another. The went to the usual job search sites to find free job postings. Some of the most popular job sites like CareerBuilder or Indeed.

The job in question, started about a year ago. Fast forward only 12 short months, and this person doesn’t like the job they accepted. Why?

Answering important questions before accepting a job is important. Being honest with yourself before you even start looking at different job postings, is likely much more important. It’s a must if you plan at finding a job you’d like to stick with and last more than a year. Turnover is an enormous issue, but job satisfaction and job search you love, is important too.

Here’s the list of 64 Questions I Wish I Asked Before Accepting My New Job:

  1. How is the commute? At the normal time I’ll be commuting and what hours are expected of me?
  2. Why is the job I’m looking at open?
  3. Where did they find my information? Application or otherwise.
  4. How is the company viewed externally?
  5. What problems exist that they want you to solve?
  6. What problems exist they don’t want you to solve?
  7. How has this role being vacant, negatively impacted the team?
  8. How is this role viewed internally?
  9. To whom would you be partnering with on a daily basis?
  10. What departments work closest with this role?
  11. How does the salary offer align with others in similar roles at the company?
  12. How are disagreements between equal team members treated?
  13. What’s the most important key to succeeding in this culture?
  14. How does the company prioritize diversity?
  15. Is diversity an issue at the company?
  16. Does the company know what diversity is?
  17. Does vacation time get used?
  18. How is “unlimited PTO” administered?
  19. What flexibility is there to work from home?
  20. What does success look like?
  21. How will you know this person will have been successful in this role?
  22. What are realistic working hours?
  23. What time do most people get in the office?
  24. What time do most people leave?
  25. How are expenses handled?
  26. Are you allowed to expense alcohol?
  27. What is the work attire requirement?
  28. How is performance managed for under performing team members?
  29. Why are the negative reviews on Glassdoor inaccurate?
  30. What tools does the company use?
  31. Does the company have Outlook?
  32. What budget do you have for ergonomics?
  33. Will I be able to have 2 monitors?
  34. How is interview feedback shared among the interviewing team?
  35. How are RSUs vested?
  36. Is there a cliff?
  37. What happens if the stock drops in value? Does the company “true up” for losses in the event the stock suffers?
  38. Are bonuses normally paid out?
  39. What is the rating scale for performance?
  40. If there is a “top rating” is it attainable, or do most people not get it?
  41. What do internal transfer look like?
  42. Is there a limit to how long I need to wait before transferring internally?
  43. What is the view of the CEO?
  44. How involved is the CEO?
  45. What systems are already set up that are working really well?
  46. What systems are not setup?
  47. Is there time for side projects?
  48. Is there support for furthering education?
  49. How much are medical benefits?
  50. Are the medical benefits any good?
  51. What other perks are there? Is there a product or service discount?
  52. How does the company view it’s future in terms of hiring growth?
  53. What does orientation look like?
  54. How long does orientation take?
  55. Do medical plans cover same-sex partners?
  56. Who has the most influence?
  57. Why does that person have the most influence?
  58. Why do people generally leave the company?
  59. What one piece of criticism about the company is fair?
  60. How does coverage for others work in the event someone is out of the office?
  61. What role does HR or human resources play in team success?
  62. How often are team builders held?
  63. Is there an annual or semi-annual company meeting?
  64. Are there blackout periods as it relates to stock purchase and sale?

The list might seem excessive or all-encompassing. It’s not. These are my personal questions I wish I would have learned before accepting a job a few years ago. It might sound silly, but they all have their purpose and intent.

I wrote the list shortly after accepting a job that had a bunch of red flags and unanswered questions after I joined. “Never again.” I thought. Sharing with the masses in hopes they can avoid the mistake I made.