One of the areas people are always interested in is knowing what questions to ask – of the mentee or of the mentor – and how to handle the difficult conversations. As you probably know or have experienced, not every mentoring conversation is an easy one; sometimes they can be uncomfortable and perplexing, for a whole range of reasons.

So being equipped with strategies and tools to help you navigate these situations is a good idea.

Knowing what questions to ask and having strategies for the ‘hard-to-have’ conversations is a big part of my mentor and mentee training workshops. Here are a few ideas for you…..

How to Manage the ‘Hard-to-Have’ Conversations

This part of my training workshop describes a 4-Step framework that can help you handle the difficult conversations, whether you are a mentor or a mentee:

1. Preparation: Purpose, process, outcome

  • Be clear about the issue and know what you want to accomplish
  • Have an open mind
  • Choose an appropriate environment in which to have the conversation
  • Go into the conversation as equals

Ask yourself:

What are my objectives for this conversation?”

“What do I think is the other person’s position in this conversation? What reactions am I anticipating?”

“What do I think the other person is going to say?

Prepare an opening statement and set forth your purpose for the conversation and the outcome you (both parties) would like to achieve.

2. Beginning the conversation: Openers

  • Reaffirm that you value the relationship
  • Explain that your intention is to maintain the integrity of the relationship and to do so you want to address an issue that needs resolving
  • Communicate the issue clearly to reinforce why you organised the meeting

It would be good for us to talk about ______________. Do you have a few minutes to talk?

I think we have different perspectives about _____________. I would like to hear your thoughts on this.

    3. Keeping the conversation going

    • Be open to listening
    • Aim to reach agreement on what the issue is and that both parties are responsible to find a solution/resolution with the overarching aim to maintain the mentoring relationship
    • Don’t interrupt when the other person is expressing their thoughts and perspectives on the situation

    “Tell me why this is important to you”

    “What would be a satisfactory way for us to resolve this together?”

    “What issue/s are we trying to resolve here?”

    “In hindsight, what do you think you or I could have done differently?”

    “How about each of us clarify in what ways we feel we have taken action to resolve this issue?”

    4. Plan for action

    • Summarise the key points of the conversation
    • Both parties agree on the way forward/resolution
    • Summarise the points of the agreement from the conversation
    • Both mentor and mentee reaffirm their commitment to working together

      And within these four steps are other important considerations such as identifying what led up to the conversation (the antecedents), timing of the conversation, how to handle emotions (yours and the other person’s), empathic listening, listening to your internal dialogue.

      I will soon be developing an easy-to-refer-to flipcard set for the’ Hard to Have’ conversations so keep a look out for it in my WebShop.


      Categories: Communication