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12 Questions for Mentoring Success

ByDr. Rosina Racioppi,
business.com writer
| Last Modified
May 17, 2019
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> Career
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I'm an avid reader of articles on developmental relationships. It's no surprise that mentoring, a major component of career success, gets loads of coverage. However, as I go through these articles, I see a huge mistake.

The articles frequently say that mentors give advice and sponsors give opportunity. This isn't always the case. Based on my experience and research working with hundreds of mentors and thousands of mentees, I have found that the most successful mentoring relationships are rooted in a two-way dialogue where mentors and mentees ask each other (and themselves) questions that result in career-advancing insights and opportunities for the mentee. Here are some examples.

Questions mentors should ask their mentees

  • What do you want to achieve for yourself, your team and your company? This question allows both mentors and mentees to zoom in on specific strategies and behavioral changes that are in tune with the mentee's goals. It moves the conversation from general to specific.
  • Why is this goal important to you, your team and the company? In asking this question, the mentor is doing a non-threatening reality check. He or she is helping the mentee assess if the goal is worth the effort needed to make it happen.
  • What difference will achieving your goals make? This question opens up a big-picture discussion about what is likely to happen when the mentee's goals are achieved. It allows the mentee to assess the potential impact personally, professionally and corporately. It's not uncommon for possible negative outcomes to surface (e.g., more time away from the family). These are not necessarily deal-breakers, but they are needed eye-openers.

Questions mentors should ask themselves

Too often, mentor-mentee relationships are defined by the mentor telling the mentee what to do. In my experience, these are the least successful relationships, as they tend to be short-lived and disappointing. For best results, mentors need to think of themselves as listeners and sounding boards, helping their mentees broaden their horizons. Asking themselves questions like these will help mentors successfully fill those roles:

  • How can I help my mentee think differently and see things differently?
  • Am I listening for what isn't being said?
  • How can I help my mentee clarify her or his thinking?

Questions mentees should ask their mentors

  • How can I use my skills and expertise differently? By asking this question, the mentee is tapping into the mentor's knowledge and experience and applying them specifically to his or her own skill set. It's a major step toward dovetailing the mentee's individual talents with corporate needs.
  • How do I develop key relationships with decision makers? Early-career mentees, especially women, often believe doing a good job is enough. This all-important question gets them past that misconception and helps them learn how to get noticed in the right ways by those who matter for their career advancement.
  • How do I know if I am working on things that matter and that will move my career forward? By asking this question early on, the mentee, like the mentor, is doing a reality check about the importance and relevance of the mentee's goals to the organization. The mentee is making sure to receive honest feedback that will keep him or her from exerting effort in the wrong direction.

Questions mentees should ask themselves

Research shows that the most successful mentoring relationships are ones in which the mentee takes an active and intentional role. Asking themselves these questions will help mentees ensure that success:

  • Am I considering how my near-term opportunities can set the stage for longer-term career goals?
  • What worked when I applied the insights gained from my mentor conversations? What's different from what I anticipated?
  • How truly invested am I in my growth and development?

There are numerous benefits from mentors and mentees asking each other and themselves questions like the ones I've outlined. Mentees stay focused on goals, gain insights into achieving and fine-tuning those goals, learn what skills and behavior patterns need adjusting, and discover pathways for interacting with key decision-makers. Additionally, mentors gain new insights into successful interactions not just with their mentees, but also with their team members, colleagues and senior leadership.

Like so many other professional and personal interactions, successful mentoring relationships aren't just about having the right answers. They're about asking the right questions.

Dr. Rosina Racioppi
Dr. Rosina Racioppi
See Dr. Rosina Racioppi's Profile
Dr. Rosina Racioppi is president and CEO of WOMEN Unlimited Inc., a leading provider of organizational solutions and initiatives to empower women as leaders.
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