Published August 6, 2024

Great Questions to Ask a Mentor or Leader to Help You Advance in Your Career

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Written by Antonio & Jasmin Bradley

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Having a mentor or a leader you can turn to for advice and guidance is invaluable for advancing your career and achieving your goals. The key to making the most out of this relationship lies in asking the right questions. Here are some insightful questions to consider:


1. What is the worst career decision you've ever made?

Understanding the mistakes of your mentor can help you avoid similar pitfalls. It also offers a unique perspective on how they overcame obstacles and what they learned from their experiences. This question can lead to a rich discussion about resilience, problem-solving, and the importance of learning from failures.


2. What would you be doing if you were me now?

This question taps into your mentor’s experience and foresight. It encourages them to think about their own career path and identify the steps they wish they had taken earlier. By learning what they would do differently if they were in your position, you can gain strategic insights and actionable advice tailored to your current situation.


3. How do you organize your time?

Time management is a critical skill for success in any field. By asking how your mentor organizes their time, you can learn effective techniques for prioritizing tasks, avoiding procrastination, and maximizing productivity. Their approach to time management can provide you with practical tips to improve your own efficiency and effectiveness.


4. What do you think is your greatest strength?

This question helps you understand what attributes and skills your mentor considers most valuable. It can also reveal qualities you might want to develop in yourself. By learning about their greatest strength, you can identify what has contributed significantly to their success and consider how you can cultivate similar strengths in your own career.


Asking insightful questions is a powerful way to leverage the knowledge and experience of your mentor or leader. These questions not only help you learn from their successes and failures but also provide practical advice and strategies you can implement in your career. Remember, the goal of these conversations is to gain wisdom that can guide you towards achieving your goals and advancing your career. So, the next time you sit down with your mentor, consider asking these questions to deepen your understanding and gain valuable insights.

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