Mastering Difficult Conversations

Discover effective communication strategies to navigate challenging and difficult mentoring conversations.

Understanding the Importance of Difficult Conversations in Mentoring

Being a mentor means supporting your mentee to progress their personal and professional development. Sometimes this involves providing them with support and encouragement. Other times, it means you might need to have a difficult conversation.

Difficult conversations play a crucial role in the mentoring process. While they may be uncomfortable or challenging, they provide an opportunity for growth and learning. Difficult conversations provide an opportunity for mentors to guide mentees through challenging situations, offer feedback, and foster trust.

Examples of difficult mentoring conversations:

  • Mentee is not driving the relationship
  • Mentee is consistently late
  • Mentee has a blind spot or is overconfident
  • Mentee has failed or received poor performance feedback
  • Mentee has a mental or financial health issue
  • Mentee has poor communication skills
  • Mentee has a poor attitude or abrasive personality

Find An Appropriate Time and Space

When there is a need to have a difficult conversation, try to find the right time and space. This means ensuring that the mentee is in the appropriate headspace (has the time and energy to absorb feedback), is in a confidential location, and is timely (feedback should be as timely as possible).

If the mentee has done something new for the first time, hold the feedback. Research shows that after doing something new, people need confidence building support and encouragement. Feedback is best delivered after someone has attempted the task a couple of times.

If the relationship has just started (it's your first meeting), hold the feedback. Rarely is a difficult conversation or feedback a good idea in your first interaction. You need to spend some time building rapport and trust before the mentee will be open to feedback.

Prepare For The Conversation

Before you launch into a difficult conversation, take the time to prepare for the conversation by reflecting on the following questions:

  • What is the core need for this conversation?
  • What is the ideal outcome?
  • How might my mentee react?
  • What are some good opening lines to open up the conversation?
  • How can I ensure my mentee understood the key points and has clarity on a way forward?

Provide Constructive Feedback

When delivering difficult feedback, it's essential to keep it constructive. Instead of focusing solely on the problem, offer specific examples and suggestions for improvement. Use the SBI (Situation-Behavior-Impact) feedback model to structure your feedback.

For example, instead of saying, "You're always late for our meetings," you could say:

  • Situation: "I've noticed that you've been late to our last few meetings."
  • Behavior: "This makes it challenging for us to make the most of our time together."
  • Impact: "Is there anything I can do to support you in being more punctual?"

Instead of focusing solely on the problem, offer specific examples and suggestions for improvement. Use "I" statements to express your observations and feelings without placing blame:

  • I've noticed...
  • I understand...
  • I see...

Listen Actively and Collaborate On Solutions

During the conversation, it's crucial to listen actively to your mentee's perspective. Give them the opportunity to share their thoughts and feelings without interruption. Validate their feelings and demonstrate empathy.

For example, you could say, "I understand that you've been feeling overwhelmed lately, and that's impacting your ability to meet deadlines. Let's work together to find some strategies to help you manage your workload more effectively."

Clarify Expectations and Boundaries

90% of mentoring relationship issues are due to misalignment with expectations, boundaries or communication preferences. If this is the case, refer back to your Mentoring Agreement and clarify expectations of your mentee. Update the Agreement if necessary and state the implications of them not changing their behaviour (eg. you may need to wrap up the relationship).  

Manage Emotions

Emotions play a significant role in difficult mentoring conversations. Both mentors and mentees may experience a range of emotions, including frustration, defensiveness, anxiety, and sadness. These emotions can make the conversation more challenging and may even derail it if not managed effectively. Ensure you understand how to best manage your own and your mentee's emotions to foster a productive conversation.

Follow Up

After the conversation, follow up with your mentee to ensure that they understand the feedback and have a plan for moving forward. Offer ongoing support and encouragement as they work to address the issue.

For example, you could say, "I appreciate you taking the time to discuss this with me. I want to support you in addressing these challenges and achieving your goals. Let's check in next week to see how things are going."

Embracing Difficult Conversations

Difficult conversations are an inevitable part of the mentoring process, but they are also an opportunity for growth and development. By approaching these conversations with empathy, honesty, and a focus on solutions, you can help your mentee overcome challenges and reach their full potential.

Remember, difficult conversations may be uncomfortable in the moment, but they are essential for fostering trust, building stronger relationships, and supporting your mentee's growth and development.

By embracing difficult conversations as a natural part of the mentoring process, you can help your mentee overcome challenges, learn from their mistakes, and ultimately achieve their goals.


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