Photo by Emily Morter


Everyone working with a new boss wants to put their best foot forward and make a lasting, strong impression. Even if you have spent a long time within the organisation and the new boss was recruited /head-hunted from another organisation, or you just got a new job, what matters most is being perceived as a competent professional by your boss and organisation.


Asking questions, not only show that you are enthusiastic, but it also helps you clarify expectations. Answered questions helps you determine what is important to your boss, and also understand the management style and persona of that boss.


Here are five questions to help you transition with your new boss


  1. What are your expectations of an assistant?

Most organisations offer a job description for every role. However, it is vital to ask this question in a one-on-one chat with your new boss, since that boss is responsible for evaluating your performance and competence. Clarify expectations early, so there is no room for ambiguity. Together with your boss, determine performance goals with timelines or milestones; to help you better understand your performance metrics and deliverables vis-a-vis this new boss.


  1. What is your definition of a successful assistant?

Success may mean different things to different bosses and can be measured quantitatively or qualitatively.

Attaining and surpassing performance metrics may be construed as quantitative success; qualitative success, on the other hand, is subjective and often measured by the boss’s observation and perception without any data to pull from.

In answering this question, your new boss will reveal what matters to him/her most; qualitative success, quantitative success or both. The tricky thing here is that qualitative metrics are often difficult to discern as these types of metrics are unique to each boss. This is where studying your boss’s persona comes in,; knowing his/her likes and dislikes.

E.g. a boss may want his assistant to shield him from as many events as possible, but another boss may aim to attend as many events as possible in order to network his way to the top. In this regard, knowing how to handle the former and later scenarios determines qualitative success with these bosses, especially as these metrics aren’t documented in a job description.


  1. What type of communication or updates do you prefer?

Assuming all bosses have the same communication styles and treating them as such, is erroneous and counterproductive, and could ultimately backfire. Clarify what kind of status updates your new boss prefers. Your old boss might have been more visual, preferring face time, one-on-one meetings and frequent verbal updates, while the new boss may prefer emails, reports and documented updates instead of face time.


  1. What are your priorities short term and long term? And what task is most important to you at the moment?

The new boss may already have mapped out his assignment and deliverables. Asking this question will prompt he/her to share some of these with you, so you can hit the ground running. However, if the boss hasn’t gotten around to this yet, this question will also prompt him to do so. Either way, asking this question will inform the boss that you are pro-active and eager to see him/her succeed.


  1. What aspect of your job would you prefer to avoid/ completely delegate?

Not all new bosses will be forthright with this answer, but it is still important to ask. The answer, if you are lucky enough to get it, would help you to understand your boss’s persona, motivation, or weaknesses. This information would help you take a proactive approach towards handling matters to such a degree that downplays his/her weaknesses and makes that boss shine.

For example, if a boss hates public speaking but is required to attend a lot of events. You could proactively shield him from a lot of unimportant meetings; attend the event yourself, recommend another manager to represent your boss whilst you proactively explore public speaking classes or speaking workshops for your boss.  


In conclusion, avoid assuming with a new boss, ask and keep asking questions. The more questions you ask, the better you can clarify and understand your boss’s motivations, increase your job success and be perceived as a professional and competent assistant.

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