Help Me Obi-Wan: Mentoring Questions to Ask During Times of Change


Steve Jobs and Mark Zuckerberg. Maya Angelou and Oprah Winfrey. Obi-Wan Kenobi and Luke Skywalker – they’re all proof that a good mentor can help us through tough times.

Everyone can benefit from having a mentor, no matter who you are. This is especially true during times of change. Even though the chaos of 2020 is behind us, 2021 is continuing to rock every corner of politics, society, and the business world. So it’s worth looking at the ways everyone can benefit from a mentoring relationship, no matter what changes are swirling around us, or where you are in your career.

The most effective mentor during times of change is the one who challenges you most. Here are a few good ways to challenge your thinking, whether you are a mentor or a mentee, so you can navigate the “next normal” in your career:

Good questions to ask your mentor during times of change:

  1. What do you think might happen in the next six months that I should be thinking about? In one year? In five years?
  2. What skills do I need to focus on developing to be effective in the long-term? How should I gain these skills?
  3. Who should I build stronger relationships with?
  4. What’s a major change that you’ve experienced (professionally)? What did you learn from it?
  5. What’s your advice for how I need to change, in order to adapt to the change that’s happening around me?

Good questions to ask your mentee during times of change:

  1. What have you learned during the past year that you will bring forward into 2021?
  2. Where can you make an impact during the next phase of your career?
  3. How can I help you work toward your long-term goals despite uncertainty in the short term?
  4. How much risk and uncertainty can you tolerate? What are you doing to manage that risk?
  5. How can I help you manage work and your personal passions right now?

Keep these questions in mind, and make the time to check in with your mentor or mentee, especially if you’re working from home right now. It might be just the jolt you need to break out of your day to day experience, and challenge your thinking.

Categories: Communication, Leadership