Tips for a Successful Connection With Your Boss in the Virtual Workplace

Tips for a Successful Connection With Your Boss in the Virtual Workplace
Photo by AJ_Watt/Getty Images

Since the spring of 2020, the virtual workplace has become somewhat of a new norm. Even as businesses and organizations migrate back to the office, many employees are choosing to remain remote -- or, at a minimum, in a hybrid work situation.


If you find yourself in a virtual work environment, consider the following tips to enhance your working relationship with your boss:


Understand Expectations

This step helps any relationship, but it’s even more important in a virtual work environment. First and foremost, know your boss’s expectations both from a performance perspective as well as a practical one. A few questions to consider asking your boss:

  • What does success in this role look like over the next two to three months? Six months? A year?
  • What do you consider to be excellent work?
  •  What is your preferred method of communication? Phone? Text? Chat? Email?
  •  How often would you like me to check in or provide updates?


It’s also important to set boundaries around working hours to ensure your boss knows when you can be reached and when you will not be available. Use the out-of-office function and calendar management to make your presence and availability known.


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Personality Traits

When you schedule your introduction meeting with your new boss (or a new co-worker), consider asking, “What are some of your pet peeves at work?” This will tell you what to avoid when you are interacting in the future and will shed light on personality traits such as being detail-oriented, strategic, organized, timely, a planner, etc.


Use these insights, combined with the knowledge of your own strengths, to fill in any gaps or anticipate future needs.


Be Known

Now is not the time to fade into the background of your home office. Ensure you are reaching out to your boss (as understood above) with updates and collaborating with co-workers as you establish yourself. Be diligent, be proactive, and demonstrate a solid work ethic. When you say you will do something, do it, and then follow up with the status or outcome of a particular task or project.


In a remote environment, one loses the serendipitous opportunities in the hallway or at the coffee station for a quick touchpoint or to lend a hand with an impromptu task. So don’t be shy to raise your virtual hand to take on a task or lead an initiative.


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Seek Feedback

Asking for feedback on a regular basis is critical to your success at work – even more so when remote, when there’s no opportunity for happenstance conversations and rapport-building. Casual comments in the hallway – “Really liked your input in this morning’s meeting,” or “Great insight on the way ahead” – simply don’t exist.


Some people do not need frequent feedback to know how they are doing, but regardless of your personal preference, it is important your boss knows you are interested in meeting expectations.


Feedback also prevents connection points from being formulaic and transactional. While you want to be respectful of your boss’s time, it is important to connect in a meaningful way beyond deadlines, data points and inputs. Here are a few questions you can use to get the conversation started:

  • What can I do to improve my contributions?
  • How am I doing when it comes to communication?
  • To what extent has my work thus far met your expectations?


Whether you have been working virtually for the past two years or are new to your organization, assess your relationship with your boss and adjust as appropriate. Let your boss know your professional goals and aspirations – it’s the only way to ensure they can give you tailored feedback to help you achieve them. Remember, your boss is not a mind-reader (thankfully!).


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About the Author

Cmdr. Erin Cardinal, USN (Ret), ACC, CPC
Cmdr. Erin Cardinal, USN (Ret), ACC, CPC

Cardinal is MOAA's Program Director, Transition Services & Family Programs. She is a Certified Professional Coach (CPC) and has extensive experience in coaching servicemembers through their transition from active duty to the civilian sector.