I'm a CEO — Being Asked These 5 Questions Always Made Me Deeply Impressed With My Direct Reports

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Deborah Sweeney102
MyCorporation.com CEO
May 27, 2024 at 12:38PM UTC

Feeling stuck in your job? I think it’s safe to say many working professionals have had “that feeling” at one point or another throughout their careers. Often, this feeling comes from trying to figure out the next step forward, but not feeling sure what it is or how to do it. You may also have questions about your future within the company. 

The real next step to take forward? Reach out to your boss to schedule in some time to talk together. This shouldn’t be an intimidating discussion, but rather one where you are able to express what your goals are so you’re able to get on the right track moving forward. Not sure what to ask? Get the ball rolling by asking these five questions.

1. How was your weekend?

How does asking this help advance anyone’s career? While it may seem unusual, you should approach the discussion from a polite place where you get to know more about your boss instead of immediately talking about your needs. By asking about their weekend, you’re usually able to find and stand on common ground together. You might already know a few things about your boss, such as what their kids are like, and can ask questions around what you know as well. This shows you are actively listening during your meetings and able to retain important information in all forms.

2. What projects are you working on?

Maybe your boss has an assignment that they need extra help with or hasn’t had the chance to start. If you’re seeking a challenge, ask how you can get involved especially if the project is in your wheelhouse. This shows your boss that you are actively want to take initiative and want to hit the ground running with the assignment, either as a team or going it solo to complete on your own.

3. How would you describe my work style?

You may think you’re exceptionally hard working in the office, but that might not be how your boss sees you. Ask for their honest feedback on your work style and overall ethic. This will allow you to find out which areas you excel in as well as those that could use some improvement. 

4. Where did employees that previously worked for you end up doing next? 

This is a tricky question to ask because when asked the wrong way, it could sound like you have one foot out the door. Kind of like you’re trying to mine your boss for this information so you can reach out to past employees on LinkedIn and get an “in” elsewhere. 

Approach this question from a place of curiosity. Many bosses have a good relationship with their former protégées and can share how they later moved on to great things. Your boss may even be able to provide insight into the kinds of skills that those former employees cultivated while working for your boss that later took them up the career ladder.


5. What can I continue to improve on?

 While this is a pretty standard question, it helps to get to the bottom of the expectations that your boss has for you. If you are doing something that doesn’t mix well with their leadership style, you will know how to fix it. If you are doing great, then keep up the good work. The key word here is “continue.” By wording it this way, you are showing your boss that you care about your overall journey in the company and want to make improvements and keep excelling onward and upward.



Deborah Sweeney is the CEO of MyCorporation.com which provides online legal filing services for entrepreneurs and businesses, startup bundles that include corporation and LLC formation, registered agent services, DBAs, and trademark and copyright filing services. You can find MyCorporation on Twitter at @MyCorporation and Deborah at @deborahsweeney.

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