Virtual Conversations to Have With a New Boss

Attempting to figure out a new boss can be difficult at the best of times, even when you see her in the office on a daily basis. But a new boss that you, as a remote worker, may never even meet face-to-face? That takes a special type of navigation. Below are some tips on making the relationship as smooth and uncomplicated as possible.

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1. Make expectations crystal clear

There is perhaps nothing more frustrating in the workplace than muddled expectations. When you attend the office in person, most of the key issues (aka: What, exactly, does your boss expect of you? What level of oversight or guidance do you expect from your boss?) are managed naturally by coexisting in a shared space. But being remote forces you to directly discuss expectations across the board. It’s most helpful if you make a list of questions beforehand when preparing to meet your new remote boss. Make sure that your list includes specific and goal-oriented queries, such as:

  • What will I need to accomplish for you to view me as successful in this role?
  • What does excellent work look like to you?
  • What form of communication do you prefer?
  • How quickly do you expect me to respond when you reach out to me during working hours?
  • What form of communication do you prefer when it is an urgent issue (for example, in writing, over the phone, video call, etc.?)

2. Speak up

Unfortunately for those who prefer to quietly blend into the background, speaking up to your new boss is particularly important when working remotely. Whether this is in virtual meetings or simply progress reports on projects, team meetings, etc.—it’s vital that your boss knows what’s going on in your world since he isn’t physically there for an impromptu check in. On a similar note, do not be afraid to speak out about set working hours. It can be easy when working from home to never really leave “the office,” but it is important that your new boss knows when he can reach you during work hours—and when he cannot.

3. Get a feel for their personality

An initial (remote) meeting with a new boss is a great opportunity to really gain an understanding of her personality. One of the best ways to do this quickly is to ask her one simple question: “What are some of your biggest pet peeves?” Why is this question in particular so effective? You get a two-for-one bonus: You find out what things to avoid when dealing with your boss in the future and, depending on the answer, gain insight into what kind of person she is. In other words, what kind of personality traits can you glean from your boss’s pet peeve? Is she fastidious? Relaxed? A perfectionist? Punctual? Take that insight and use it to your advantage.

4. Request feedback

As a remote employee, it is particularly important to get as much feedback on your performance as possible. Consider starting this conversation a few weeks into your new working relationship and continue to touch base with your boss about it every few months. To help get the discussion started, consider asking questions such as:

  • What (one, two, three) thing(s) should I start doing to improve my contributions to the company?
  • How is my communication level with you (either in general or about specific tasks such as deadlines, progress, etc.)?
  • Has my output thus far matched your hopes and expectations when you hired me?

It can be challenging to navigate a discussion with your boss, whether it has to do with your career trajectory, your salary, or some other issue related to your overall happiness at the company. But keep these tips in mind to maintain a healthier, happier relationship with your boss—even if that relationship is destined to remain virtual.

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