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How to Lead a Mentoring Conversation

Guidelines for the Mentor:

  • Build a relationship of rapport and trust.
  • Discussions are confidential.
  • Conversations can be free-ranging – take a holistic approach.
  • Allow mentee to talk about their issues and aspirations.
  • Draw out the mentee’s thoughts and feelings. Be curious.
  • When appropriate and relevant, mentor can share experiences.
  • Be future focused.
  • Enable mentee to reflect and discover their own truth.

Mentoring plays an important role in leadership within Toastmasters, and many clubs have mentoring programs. But sometimes, members misunderstand its nature, confusing it with coaching, or expecting mentors to always initiate contact, not the other way around.

Recently, Past International President, Dilip Abayasekara, DTM, AS, shared tips on mentoring during his virtual workshop in District 86: “Accelerate your professional development with mentor-mentee relationship”, and referenced Ann Rolfe’s book about mentorship.

You don’t need a formal title to lead a mentoring conversation in Toastmasters. What matters is helping members have those “aha” moments in figuring out next steps. Conversations can happen one-on-one or in group settings, tackling anything from club goals to personal development.

The conversation begins with reflecting on the present, envisioning the future, setting goals, and providing ongoing support. Conversations are flexible and tailored to the member’s needs and goals.

To effectively lead a mentoring conversation, you can use Rolfe’s framework, which revolves around four key questions:

  • Where are you now?
  • Where do you want to be?
  • How might you get there?
  • How are you doing now?

But before we explore Rolfe’s questions, let’s understand what a mentoring conversation involves.

Like mentoring itself, discussions can vary widely in form and purpose within Toastmasters. Mentoring relationships and conversations are not static; they are responsive to the member and their situation. There’s no “one size fits all” approach. A mentoring conversation provides a safe space to examine thoughts and emotions.

Traditionally, mentors were seen as wise sages passing on knowledge and experience. However, contemporary mentoring emphasizes listening and asking questions rather than just imparting knowledge. Its not about giving advice; the process involves supporting, encouraging, and occasionally challenging mentees.

The four guiding questions can help to structure discussions effectively. Keep them in mind when in conversation with your member’s needs and goals.

Where Are You Now?

Encourage the mentee to think about what’s going on in their life or what they’re trying to achieve. Ask open-ended questions, gentle probing and reflective listening to help them dig deeper into their thoughts. Through reflective conversation, the mentee may discover their own insights.

Where Do You Want to Be?

Help the mentee imagine where they want to be in the future. Talk about different options that match their goals. By chatting openly and sharing experiences, you and your mentee are exploring smart choices about what they want to achieve.

How Might You Get There?

Once the mentee knows where they are now and where they want to go, talk about how they can get there. Let them come up with ideas and plans, but be there to help if they need guidance.

How Are You Doing Now?

Once the mentee is working out their action plan, check in and see how it’s going and what they’ve learned. Encourage reflection. Talk about what worked and what didn’t, and remind them that it’s okay to adjust their plans as they go.

By following these four questions, you can guide your mentees in a way that helps them grow.

Practical Applications

The mentoring framework isn’t just for Toastmasters; it is useful in career development and performance feedback. For career development, start with identifying values, priorities, and strengths, aligning personal aspirations with professional goals.

Similarly, as a manager giving feedback, it’s having a mentoring conversation about what they feel needs work, finding out what’s getting in the way, setting goals together, and supporting changes.

Mentors, Be slow to offer advice:

  • Mentors don’t have all be answers.
  • It is more effective to help mentees find their own insights.
  • Most people need to be heard, not told what to do.
  • Ask questions (who, what, where, when, how, why).
  • “Tell me more”
  • Find out what’s important for the mentee – values, beliefs, aspirations.

Mentoring means having conversations where listening and trust come first. Great mentors don’t rush in with all the answers; they ask questions and offer support, letting mentees find their own way forward.

Created by Nancy Movrin DTM, District Director Manager, District 86 2023-2024, Cambridge Toastmasters