Previous Prescriptions from the Doctor:

Handling Feuding Workers

Hiring Persons With Disabilities

A Change of Perspective

Are You Annoying?

Avoiding Supervision Mistakes

Understanding a New Boss

Workplace Violence

Employee Discipline

Personal Problem

Half of Life in Meetings

New Year's Resolutions - Fact or Fantasy?

Small Business Mistakes

Understand New Boss

©Connie Sitterly

The information contained in these responses should not be considered legal advice. Consult an attorney if you have any legal questions.


Dear Workplace Doctor,

I recently inherited a new boss, and would like to get off to a good start and develop a good relationship as quickly as possible. Do you have any suggestions how I can speed up the process of understanding my boss?

Jimmie S.


Dear Jimmie,

Your astute question regarding how to understand, transition, and develop a relationship with a new boss can be best answered with .........more questions. 

As you interact with your boss, keep the following questions in mind: 
  1. What are your boss's goals? priorities? mission?
  2. What does your boss complain about and praise in others?
  3. How well does your boss make decisions? control moods? delegate? organize? give instructions and directions? gives feedback? take or encourage risks? accept and lead change? humor?
  4. What are you boss's primary concerns, pressures, or problems?
  5. Why are you getting a new boss? Why was s/he selected as boss?
  6. How well does your boss understand what you do, regardless of job description or title? How do you spend your time? What are your priorities, goals, and challenges?
  7. What expectations and preferences does your boss have of you? You of your boss?
  8. What is your boss's management style and motives? 
  9. How compatible are your goals, ambitions, priorities and compare to your boss'? 
  10. Does your boss encourage creativity, empowerment, independence?
  11. What is your boss's preferred method, level of detail, follow up, and frequency of communication? Availability and best/worst times to discuss tasks? 
  12. What are your boss's strengths and weaknesses?

I encourage you to meet for an 'expectation exchange' to share answers to those questions personally appropriate for you and your situation. Open, direct, honest communication is two-way process. By taking responsibility and initiative to share, ask and agree, both your relationship and results can take a positive, productive, and more enjoyable leap forward.

As your relationship progresses, note if you can freely express opinions, ask for help, or make suggestions and if you understand specific things to improve your performance. If not, repeat: share, ask, and agree.

The Workplace Dr. TM