OP-ED: EA Coach Exclusive: Questions EAs and Executives Should Ask Each Other

“The single biggest problem in communication is the illusion that it has taken place.”

– George Bernard Shaw

As I type this, my boys (ages 5 and 7) are playing with Legos in the next room. At the moment, they’re playing very well together and it’s one of the sweetest sounds I’ve ever heard.

[As soon as I was done typing the above sentence, my 7 year old came in with his fidget spinner UFO and tiny alien and walked all over my desk. It was very sweet until I realized my son’s hand – the one that just took a tour of my mouse and keyboard – was covered in snot. Ah, the joys of parenting.]

If I’m lucky, my boys will get through this play session without incident. But these precious moments of play often halt abruptly with a, “Dad, Silas won’t let me have the blue lego!” or “Dad, Weston took my red Lego!”

In these moments I tend to ask the following question:

“Did you ask your brother for what you want?”

9 times out of 10 they answer, “No.”

In other words, the failure to communicate is one of the primary issues my boys have when trying to work well together. If you’re a parent, I’m sure you have no idea what I’m talking about.

Communication in the Workplace

Recently, I was on a coaching call with an assistant who said she wanted to do more for her executive, but she didn’t know where to start. She talked about how she wanted to step up and be a leader. She wanted to take more initiative. I asked her how often she and her executive meet together. She said they rarely, if ever, get time to meet.

I spoke with another assistant who meets regularly with their boss but had similar problems. Her issue wasn’t the lack of face to face meetings, but the fact that those meetings lacked structure.

As I coach assistants and executives through similar roadblocks, I am more convinced that – just as with my Lego-loving boys – improved communication is the key to a successful working relationship.

Think back to some of the best conversations you’ve ever had. Or, the best podcast interviews you’ve ever listened to. Or, the best counseling or therapy session you were a part of. What was the common thread in all of these? They were full of good questions!

The best way to improve communication in an executive/assistant relationship is to ask good questions. I’m excited to share several questions I’ve personally found to be valuable conversation starters when working with my bosses.

First, I’m going to share six questions assistants should ask their bosses. I’ll then share six questions executives should ask their assistants.

Let these questions be a launching pad for some game-changing conversations, and a catalyst for taking your executive/assistant relationship to the next level.

Assistant: 6 Questions You Should Ask Your Boss

To my fellow assistants…

Open dialogue is crucial to a productive and healthy working relationship, but your boss should not be the only one asking questions. If you want to make an impact and be a leader in your role as an assistant, you’ve got to take initiative by asking questions as well.

The following questions are great conversation starters to help you be proactive and anticipate your boss’ needs – which will ultimately make you a better leader.

1. What’s one thing I could do to make your job less stressful this week?

Be prepared to answer this question before you ask it. In other words, there is probably something you already know you could help your boss with that would make their job less stressful.

Don’t ask this question if you’re not ready to make suggestions.

Note: If you’re hesitant to ask this question, you should probably consider whether or not you’re in the right role. An assistant’s job is to make their boss’ job easier, and if you’re not excited about doing so, something is awry.

2. In what way do I frustrate you? How would you recommend I change?

This is a fun set of questions to ask your boss. Yes, it can be very humbling, but if your boss is frustrated about something you are (or aren’t) doing, you should want to know.

Remember this: Don’t take what they say personally. Just because something you do may frustrate them, this doesn’t mean you are a terrible person, or assistant.

Seriously, don’t take it personally!

3. What’s my greatest strength? Do you believe this strength is being utilized? If not, what changes could we make to get more out of me in this area?

Ok, I realize this set is three questions, but you get the idea.

You may excel at proactively managing your boss’ calendar and communicating to the team. But, does your boss give you opportunities to work in these areas, or are they asking you to run small, pointless errands all the time that aren’t honing your skills?

You could also be the best person in the company at putting together slide decks, but your executive team insists on doing it themselves.

Ask them this question and if they can’t think of anything, remind them where you excel, so you can begin to work more from your strengths.

4. Is there a task or project you’re working on that I could take care of?

Don’t let your boss micro-manage or work on tasks that aren’t in their job description. Maybe they feel bad giving you more to do. Or, they don’t trust you to be able to handle it.

Whatever their reasoning, this is your chance to step up and take more off their plate so the company can succeed. Check out my post here on why we micromanage and how to stop.

5. Could we rearrange our calendars to make things easier, more enjoyable, and more productive for you?

The answer to this question should always be, “Yes.”

You should be aware of what meetings your boss should or should not be attending. Make it a priority to sit down with them and do an audit of their calendar. If you need a template for how to take a productive audit of their calendar, check out my worksheet here.

6. How can I help you prioritize your to-do list for the week?

Many executives know what they need to do, but they get overwhelmed and don’t know where to start. This is where you can help them break their to-do list down into bite-sized tasks. Then, you both can work together to prioritize the list so they don’t miss anything important.

Ok, the above questions are probably plenty to get you going. My hope is these questions will serve as a starting point for open dialogue between you and your boss, so you can read your boss’ mind and be better in tune with their priorities.

Now, some of you might read these questions and get anxious. You might be afraid to ask your boss because you already have a ton of tasks on your to-do list. You may even be thinking, “There’s no way I can ask that question!” If that’s you, I get it. It’s not easy to have conversations like this with our boss.

But, if you want to be a leader assistant, you must ask these types of questions. If you truly want to be what they want—a mind-reader—you can’t sit on your hands and wait for them to initiate.

No to mention, asking these types of questions will provide more value to your boss than an artificially-intelligent assistant will soon be able to provide. (I’ll actually dive into that topic in a join webinar with Base CEO Paige McPheely on May 15—sign up here!)

Executive: 6 Questions You Should Ask Your Assistant

To all the executives, pastors, CEOs, and entrepreneurs…

How would you feel if your long-time, rockstar assistant—who took you months to find—suddenly told you she’s quitting because she wants to become a photographer or start her own business?

You’d probably freak out and say something like, “What am I going to do without you?! Why didn’t you say anything before?! It would have been nice to have time to prepare for this.”

To which she might reply, “You never asked.”

Help Your Assistant Help You

I’m willing to bet you don’t want the above scenario to happen. Not that you don’t want your assistant to dream of a different career—even though you may selfishly want her to stay. But, other than the convenience of having a heads up, wouldn’t you also want to know so you could encourage her, and maybe help her achieve her dreams?

If you had known about your assistant’s long term goals, you could have given her flexibility to take some photography (or business) classes. Your company might have even provided a scholarship to help pay for them.

Helping your assistant—you know, the one you can’t live without—develop skills to find work elsewhere sounds crazy, right? Maybe, but your assistant is the easily one of the most important employees in your company. Investing in them will positively impact the culture and reputation of your company.

Let’s say she takes some classes and eventually leaves the company. Don’t you think she would highly recommend working for you to everyone she knows? The quality of people who would apply to work for you would increase, making it easier for you to find a replacement.

Just Ask

In my years as an Executive Assistant, one of the most helpful things my bosses have done is show interest in my personal life. They’ve allowed me the flexibility to do things I love and have encouraged me to grow.

Whether it was letting me drive to Kansas City to attend October baseball (Go Royals!) during a work week, or loaning a leadership development book to me, my executives’ care spoke volumes.

Every once in a while my boss will ask me questions that make me think outside the box and wrestle with my life goals. He will also ask questions about our work and offer to help find solutions to my problems—not just his. It always throws me for a loop when he asks, “Is there anything I can help you with?” Wasn’t it my job to help him, not the other way around?

You can call it what you want—employee retention, good leadership, or being a caring person. However you look at it, it will benefit your assistant greatly—and in turn, you—to just ask.

6 Questions to Ask Your Assistant

I recommend starting off by asking your assistant the following questions, or your own variations of them to better fit your context.

  1. What’s one thing I could do to make your job less stressful?
  2. What’s your biggest frustration with me? How can I do better?
  3. Are you satisfied with how much money you’re making?
  4. Is there an online course or class you’ve been wanting to take that would help you grow—personally or professionally?
  5. Is there a way to rearrange our weekly schedule to make things easier, more enjoyable, and/or more productive for you?
  6. What future goals do you have? Do you feel this job helps or hinders your desire to accomplish them?

You don’t have to ask all of these questions in one sitting, but make it a regular practice, and you won’t regret it. I list 3 additional questions here if you’d like more ideas.

Just remember, if you don’t listen and take action on what is possible to take action on, there’s no point in asking your assistant these questions.

Assistants and Executives: I hope these questions are helpful for you!

If you’re interested in hearing more on the topic of improving the assistant / executive working relationship, check out The Leader Assistant Podcast at

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Written by Jeremy Burrows

Jeremy Burrows Jeremy Burrows has 12+ years of experience as an Executive Assistant supporting fast-paced, high-capacity, influential leaders. He has worked with CEOs, Pastors, Authors, Speakers, and Board Members in both the nonprofit and for profit sectors. Currently, Jeremy is Executive Assistant to the CEO of an artificial intelligence software company in St. Louis, MO. Jeremy is also Founder of where he helps executives and assistants gain more time, energy, and success via his blog, group training, one-on-one coaching, speaking, and The Leader Assistant Podcast.