The 3 best career path questions to ask your boss or mentor

Show your boss you want to grow in your current role by asking these three career path questions to help them help you achieve success.

You’ve got your end of the year one-on-one meeting coming up. Asking the right career path questions shows your management team that you are serious about your current role in your company and that you are looking to grow as an employee. 

As the Operations Manager here at Know Your Team, I have a solid idea of where I want to be career-wise one year from now – as well as in five and ten years – and both of my managers have expressed their willingness to help me achieve my goals of where I want to be.

Based on my own experience during one-on-one meetings, I have eagerly asked these three career path questions and have received helpful and supportive feedback in return. 

#1: “Are there any particular subjects you think I could benefit from learning?

Loving to learn is an important attribute to have because it highlights your willingness to adapt to new situations and roles in the workplace. When I got hired as Operations Manager, one of the first things I asked Claire, our CEO, was for reading material. I took a few business courses in college, but to be honest, the content never stuck. 

Since I joined Know Your Team in a business role, I knew that I needed to hone in on business knowledge – specifically around leadership and management – if I had any hope of thriving in my new role. Therefore, I made the difficult choice to set my beloved fiction books and memoirs aside and force myself to read books that could teach me useful skills

Not only was Claire impressed by my eagerness to learn, but she delivered on my ask for material by sending me copies of her favorite books that she thought would benefit me by reading. 

I started with “The Effective Executive: The Definitive Guide to Getting the Right Things Done,” and am moving onto “Crucial Conversations: Tools For Talking When Stakes Are High.”

She also sent me The Fifth Discipline: The Art & Practice of The Learning Organization, The Art of Gathering: How We Meet and Why It Matters, and On Writing Well: The Classic Guide to Writing Nonfiction – all books with subjects essential to my current role within KYT. 

To help keep me accountable, I started a “Book Club” in our Watercooler online leadership community, where I have 1,000+ people counting on me to follow through with weekly chapter summary threads of the books I read 🙈. 

#2: “What are some skills where you think I could improve?

This is one of the scariest career path questions to ask. It can make you feel you’re in a vulnerable position.

When you ask this question, make sure you take any hard feedback you receive in stride and realize that your boss or mentor is only trying to help you. After all, your purpose in asking these career path questions is because you want to be better, right? Everyone has areas where they can improve. As they say, nobody is perfect – and yes, this even includes you (and me)! 

For example, when I ask this question, I’ve been told that I am extremely fast and efficient. While not necessarily a bad thing, it was pointed out that sometimes this can come off as brash – especially in written communication.

As a result, I have made a concerted effort to slow down and make sure every interaction with a customer I have starts with a warm greeting, a thoughtful answer, and a pleasant send-off. Your interactions with people, especially with clients and/or customers, can be the difference between someone who buys into and someone who walks away from your company.

Asking about what skills you can improve on doesn’t come without the caveat: Be ready to accept hard truths. Don’t let yourself get down in the dumps and walk away with an “I suck” mindset. Instead, figure out how you can improve. Claire wrote a great post on five ways to receive critical feedback well — and not get defensive that I highly recommend you check out.

#3: “What do you see my ultimate role in the company as being?

Asking where your manager sees you being in five or ten years should be number one on your list of career path questions to ask. 

It’s not uncommon for other people to see talents in you that you don’t see in yourself. This is usually attributed to what is commonly called “impostor syndrome.” According to Wikipedia, “impostor syndrome is a psychological pattern in which someone doubts their accomplishments and has a persistent internalized fear of being exposed as a “fraud.”

Perhaps you think you’re destined to be an administrative assistant forever like I did. You look at your boss and think, “I could never do things like her. She writes so much better than me. I could never speak in front of an audience as she can.” Well, I’m here to break it to you: That is BS. I mean, look at me now, writing on this blog. While I was hired with no expectations of ever having this privilege, “Look, Ma, here I am!”

I’ve also expressed that while a terrifying idea right now, I have an interest in public speaking. It’s a goal of mine one day to deliver a keynote speech on the topic of empowering women and people of underrepresented groups and minorities to get involved in technology. My career path has been an inspiring one I’ve been told, and I would like to share my story with people who might benefit from hearing it someday. Claire has been amazingly supportive and has said that she thinks I could get there – and even do it while representing Know Your Team.

Additionally, I’ve also shared my desire to lead my own team within the company – another thing Claire said she could see me doing in the future as we grow. I feel this is part of the reason she chose some of the books she did for me to read and challenges me now as she does 😉.


Asking these three career path questions is how you learn and share your sincere desire to be on the right track towards a long and meaningful career within your company. Your willingness to improve will not go unnoticed – and most likely, you will gain opportunities in which you may have never dreamt of. 

If you want to level-up as an employee, here is where you start.

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Written by Mandy Moore

Operations Manager at Know Your Team. My goal is to love what I do every single day. Follow me on Twitter at @therubyrep.

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