by | Jun 14, 2022 | Blog, Executive Assistant

So you’ve got a new boss, and you want to start things off on the right foot. But how exactly do you build a strong working relationship with your manager as an executive assistant? How do you get to know them without being a kiss-up? As with any new relationship, the key is simply starting a conversation and asking questions. This post addresses some of the best questions to ask your new boss as an executive assistant.

The Importance of Communication With Your New Boss

Good communication is key to developing and maintaining a strong relationship with your new boss. It helps you become a superstar executive assistant they can rely on. Communication also promotes collaboration, innovation, problem-solving, motivation, and career growth. 

Establish a Strong Working Relationship

The relationship between an executive and an executive assistant is a unique one. Your role as their right-hand person means you work together closely every day. Over time, most EAs become their boss’s sounding board, their trusted confidant, and even their friend.

But developing this strong relationship requires good communication. Communication helps you get to know each other, develop mutual trust and empathy, and set healthy boundaries. 

Understand Their Working Style

Communication helps you get to know your boss’s working style. Understanding how they work will help you plan their schedule and organize their workload accordingly. You can also sculpt your relationship based on their working style.

Is your boss more productive first thing in the morning or later in the afternoon? Do they prefer having all of their meetings on one day or spread across the week? Do they mind being interrupted while working, or would they prefer you save any questions for pre-organized check-ins? These are all vital things to know as an effective EA.

Encourage Collaboration and Innovation

Often the best ideas come when people work together. Just because they’re the boss doesn’t mean they don’t value your input. You may be able to give a different perspective or help them clarify their thoughts. Taking time to sit down and bounce ideas off each other can hugely affect your company’s success. Organizations that encourage communication are far more innovative than those that don’t.

Enhance Problem-Solving Possibilities

Communication and collaboration are also essential elements of problem-solving. Communicating effectively with your new boss allows you to identify minor issues before they grow into full-blown problems. The more you talk, the better you’ll become at anticipating their needs and staying one step ahead of any potential problems in the future.

Career Growth

Good communication also supports your growth on the EA career path. Asking your boss for advice, feedback, and constructive criticism helps you improve your role and grow your skills as an assistant. Asking for feedback lets your boss know that you’re thinking about promotion and development.

Executive assistant works with CEO on employee engagement

Questions to Ask Your New Boss as an Executive Assistant

Questions are a great place to start when initiating early conversations and building a relationship with your new boss. So what questions should you ask your new boss as an executive assistant? These are some we suggest.

What Can I Do to Make Your Job Less Stressful?

One of the first questions to ask your new boss is how you can make their life easier. That’s what an EA is there for, after all. What jobs do they hate doing? What tasks do they not have time for? Are there any particular projects you can take off their plate immediately? Show you’re eager to help.

How Do You Prefer to Communicate? 

Knowing your boss’s preferred communication style is essential for building a positive working relationship. Some people prefer emails or IMs, while others prefer picking up the phone or talking in person. Learn their communication style early to avoid unnecessary stress.

What’s the Company’s Biggest Challenge?

You want to understand the company’s biggest challenge and how you can help your boss tackle it. Asking how you can help the company succeed shows you’re a team player and thinking about the bigger picture. It also shows you’re a proactive team member who doesn’t wait for someone to tell you what to do.

What Were the Traits of the Best Team Members You’ve Managed?

This question will help you understand what your boss values most in their employees. Are there any skills or traits that stand out to them? You can then model yourself after those traits to make sure you impress your new boss.

How Will You Evaluate My Performance?

To stay motivated and on track as a great executive assistant, it’s crucial to know exactly what your new boss is looking for. What are your boss’s expectations of you, and how will your boss evaluate them? Setting SMART performance goals and milestones give you something to aim for.

What Would You Change About the Way Work is Done in My Role?

Find out if your boss would take a different approach to your role that might be more beneficial to them and the company. Asking this question shows that you aren’t afraid of change and are willing to adapt accordingly.

Can We Schedule a Follow-Up Conversation?

Having a conversation with your new boss isn’t a one-and-done situation. Communication is an ongoing requirement in an effective working relationship. Schedule a follow-up in a couple of weeks so you can check-in and evaluate how things are going. This timeline will give you and your new boss some more time to get to know each other better and experience each other’s working styles.

Questions to ask in your first follow-up with a new boss:


  • Is there anything I do that frustrates you? How would you recommend I fix it?
  • What’s something I should start doing that I’m not doing currently? 
  • What’s something I do well and should continue to do?
  • Is there any part of my job you feel you don’t know about but would like to?
An Executive Assistant being interviewed by two executives

Building a Strong Relationship With Your New Boss 

A strong relationship doesn’t form overnight. It can take a lot of time and effort. Below are some more ways to build your relationship with your new boss.

Look for Common Ground

Do some research on your new boss. Take a look at their LinkedIn and social media profiles. Look for common ground such as mutual interests, shared sports teams, or similar hobbies. Find something to break the ice when you first meet them.

Practice Empathy

Empathy is a vital skill when building any new relationship. You may feel anxious about getting a new boss. But remember to look at things from their perspective too. They changed EAs or got one for the first time. Don’t overwhelm them. See what you can do to make the transition easier. Your empathy and kindness won’t go unnoticed.

Achieve Early Wins

Prove value to your new boss immediately. Determine what would make a significant impact in a short amount of time and do that thing. It could be anything from reorganizing the office filing system to completing an ongoing project. Let them know that you’re eager and ready to make a difference in their life.

Structure Appropriate Discussion Time

Communication is essential for building and maintaining a strong relationship with your boss. Schedule regular meetings and check-ins. These could be daily, weekly, or monthly. Structured discussion time allows you to see how things are going, catch up on ongoing projects, and identify issues before they escalate. 

Take Initiative

Bosses love employees who take initiative. Don’t wait for your new boss to start every conversation or ask you to do something. Demonstrate your enthusiasm by being proactive. Prove your value to them and the company.

Connect Can Help You Excel as an EA

Want to become the best possible executive assistant for your new boss? Our professional assistant training program teaches you the skills you need to be a fantastic EA who exceeds your boss’s expectations.

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