How Administrative Professionals Build Great Relationships with Difficult Bosses

You may have experienced this: you’re working for an executive, and someone off-handedly says, “I don’t know how you can work for them, they’re so demanding, scattered, unfriendly (fill in the blank here with some derogatory term).” 

Here’s the truth: Your relationship with your boss is critical to your career and your satisfaction with your job. They help you get the resources you need, move obstacles out of your way, and support your continued development. 

 And as an administrative professional, a large part of your role is to make your boss’s job easier. That means understanding what makes them tick. And supporting them in the best way possible. And sometimes brushing off comments that run counter to that.

That takes strong communication and emotional intelligence skills.

3 Kinds of difficult boss behavior, possible causes, and how to manage your relationship with them: 

1. The micromanager. 

   Having someone looking over your shoulder, scrutinizing your every move can crush your motivation and make you feel stressed. Several things cause someone to micromanage.  Many of them have little to do with you or your work.  

   First, it takes a high degree of trust for someone to hand over an assignment.  If you’re new or have fallen short on a previous project, it’s natural for someone to stay closely involved. 

   Inexperience as a leader can also cause micromanaging. The person could be having trouble letting go of responsibilities they once did themselves. Fear can also drive the behavior. Your boss might feel pressure from above and is worried that a project could fail on their watch. 

   What to do: Communication is the path forward with a micromanager. You want them to see you as a reliable support. That means providing regular updates with your progress on projects. Find out how much detail is helpful to your boss (and sustainable for you). When you encounter problems, keep them in the loop but have solutions. You want to show them you’re a problem solver who can be trusted to get the job done.  

   It’s also helpful to make sure you’re clear on their expectations at the outset of the project. What should the final project look like? When is it due? Is there an example they can give you so you’re both on the same page? Having this clarity will help ensure that the outcome hits the mark – and matches their expectations. 

    

2. The unappreciator. 

   Not getting recognition or a thank you for your work is frustrating and makes you feel overlooked. But let’s face it, some people are not very good at showing gratitude. The reason can be as simple as they’re busy and don’t make time for recognition. Or more complicated in that they generally don’t believe it’s needed or aren’t quite sure what to say.

   What to do: Sure, getting recognition, acknowledgement or praise makes us feel great. But the bottom line is, those things don’t change who you are or why you put your quality stamp on everything you do. 

   You can’t ask someone to start thanking you. But you can show appreciation to those around you – including that boss who’s frugal with their own words of appreciation. “Hey, I really appreciate the time you spent explaining this project.” “The board seemed impressed with your data presentation this morning. Let me know if there’s anything else I can do to help.”  You can also internalize your own good work by pausing to reflect on something you did well.

    

3. The avoider. 

   When you’re working for someone who doesn’t show up for you, doesn’t respond or follow through, and doesn’t give you feedback, you’re probably working for a busy, poor communicator. It’s likely their behavior is unintentional. And while sometimes, no news can feel like good news, not knowing where you stand is never a good position to be in. 

   What to do: Start by booking regular time on your boss’s calendar. A weekly touch point where you come in with a quick agenda of items to review is a good start. Talk about challenges and bring your ideas for solving them. Talk about progress and next steps. Keep the meetings on track so your boss also sees the value in them. 

   And finally, ask what you can take off their plate. “I know you’re getting ready for the January conference; is there anything I can help you handle for that?” This time and these words will gain the respect of your boss. 

   If for some reason, your boss starts cancelling the meetings, remind them of how important these one-on-ones are for keeping things on track. Ask if there’s a better time or if the meeting could be a phone call instead? Adapt as needed.

As an administrative professional, building a strong working relationship with your boss is at the heart of what you do. Yes, every boss has flaws. By strengthening communication and trust, you help fill in gaps and help in areas they might be weak. And you become indispensable no matter who you’re working for.