By Saeed Mirshekari

Apr 29, 2023

Today, I want to talk about a topic that's close to my heart: mentoring. As a mentor, one of the most important things we can do is to ask the right questions that can help our mentees grow and learn. But sometimes, it can be difficult to know what questions to ask. That's why I've put together a list of probing questions that can help you as a mentor to guide your mentees towards their goals and aspirations.

These questions are designed to spark meaningful conversations and encourage reflection, so you can help your mentees gain new insights and perspectives. So whether you're a seasoned mentor or just starting out, I hope you'll find these questions useful in your mentoring journey. Let's dive in!

Exploring current role

β˜β˜‘ What do you enjoy working on now?

β˜β˜‘ What are your greatest strengths?

β˜β˜‘ What challenges you?

β˜β˜‘ What are your biggest areas for development?

β˜β˜‘ What are you struggling with?

β˜β˜‘ What do you want to do more of? Less of?

β˜β˜‘ In what areas are you getting feedback around work well done?

β˜β˜‘ In what areas do you want to develop in your current role?

β˜β˜‘ What accomplishments are you proud of?

β˜β˜‘ How would you describe your work style?

β˜β˜‘ How do you react to developmental feedback?

β˜β˜‘ What do people seek your help on?

Exploring next steps

β˜β˜‘ What aspects of the broader business at your company interest you?

β˜β˜‘ Are there untapped opportunities in your company that interest you?

β˜β˜‘ How are our customers changing? How can you fill those changing needs?

β˜β˜‘ What are our most significant challenges? How can you help solve them?

β˜β˜‘ In what ways can you develop your skills to meet those challenges?

β˜β˜‘ What specific skills do you want to learn?

β˜β˜‘ How are your skills being underutilized?

β˜β˜‘ How can you apply your skills and interests in other projects or areas at your company?

β˜β˜‘ What is next for you?

Exploring actions and future opportunities

β˜β˜‘ How could your skills and experiences support your personal development or career?

β˜β˜‘ What is your 6-month, 1-year, 3-year and 5-year career goals?

β˜β˜‘ What are you willing to do to make a career change happen?

Probing questions can help you gain a deeper insights into what motivates your mentee. This is not an exhaustive list, but a set of questions that will help you deepen your conversations.


In conclusion, asking probing questions can be a powerful tool in mentoring relationships. By asking the right questions, we can help our mentees gain clarity, deepen their understanding, and develop new perspectives. As a mentor, it's important to remember that our role is not to provide all the answers, but rather to guide our mentees towards finding their own solutions.

The questions on this list are just a starting point – feel free to adapt and modify them to suit your own mentoring style and the unique needs of your mentees. Ultimately, mentoring is about building meaningful relationships and making a positive impact on someone's life. By using these probing questions, you can help your mentees grow and achieve their full potential.

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About O'Fallon Labs

In O'Fallon Labs we help recent graduates and professionals to get started and thrive in their Data Science careers via 1:1 mentoring and more.

Saeed Mirshekari, PhD

Saeed is currently a Director of Data Science in Mastercard and the Founder & Director of O'Fallon Labs LLC. He is a former research scholar at LIGO team (Physics Nobel Prize of 2017). Learn more about Saeed...

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