6 Questions Assistants Should Ask Their Boss

By Jeremy Burrows at GoBurrows.com

I asked several executives a simple question; “What’s one thing you wish your assistant would do more of?”
Every single one of them said the same thing – they wished their assistants were better at anticipating their needs, aka reading their minds.
This wasn’t surprising to me as most assistants I talk to know they should anticipate their boss’ needs and read their mind.
But to be honest, not many of them know how to practically do this.
So how can we as assistants read our boss’ mind?
Here are a few mind-reading tricks I’ve found to be helpful over my many years as an executive assistant.

Meet regularly

First, I like to meet with my boss regularly (at least once a week).
After all, the best mind-readers are in the same room as the mind they are trying to read.
If you’d like to read more on this topic, check out my thoughts on the most important meeting of your week here.

Spend time looking ahead

Next, I try to take time every week to look 3, 6, and 12 months ahead. I look for travel I have yet to book, events I still need to gather info on, and I make sure there are no conflicting family events for my boss.
Our bosses don’t have time to look at every detail of a trip scheduled 6 months from now. That’s one of the reasons they pay us.
Ask your boss what’s on their mind
In my experience, the best way to be proactive and truly anticipate what’s coming is to ask your boss what’s on the top of their mind.
Questions like, “What are your top 3 concerns right now?” or “What’s keeping you up at night this week?” will draw out valuable info from your boss which will help you align with what’s on their mind.
Open dialogue is crucial to a productive, and healthy working relationship. I wrote about 9 counterintuitive questions your boss should be asking you here. But they should not be the only one asking questions.
If you want to make an impact and be a leader in your role as 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.

6 Questions to Ask Your Boss


Question 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.
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.

Question 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.
Just 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!

Question 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 is 3 questions, but you get the idea.
You may be really good 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?
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 what you’re good at, so you can begin to work more from your strengths.

Question 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.

Question 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.

Question 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.
What about you? What type of questions do you find help draw out valuable info from your boss? Comment below – I’d love to hear from you!


About Jeremy

Jeremy has 12+ years of experience as an Executive Assistant supporting fast-paced, high-capacity, influential leaders.
Currently, Jeremy is Executive Assistant to the CEO of Jane.ai in St. Louis, MO. Jeremy is also Founder of Go Burrows, LLC where he helps executives and assistants accomplish their goals without burning out. He does this via online courses, one-on-one coaching, speaking engagements, and his online blog at goburrows.com.