Three Mentoring Conversations


The Importance of Conversation

Meaningful conversations are essential for creating trust and building rapport in a mentoring relationship. Getting to know each other can only be accomplished by asking questions and practicing active listening skills. Effective communication helps bring about new ideas and developments, as new pathways come to life. In short, discovery and learning happen through conversation.

Mentoring conversations are most productive when they go beyond simply giving answers. There should be an honest two-way dialogue between both parties exchanging information and connecting. Mentorship is about processing possibilities and cultivating destinations, and it’s about gaining higher levels of understanding and experience. Because of the give-and-take nature of conversations, it’s the most effective way to share ideas and experiences. 

Meaningful Mentoring Interactions 

Engaging in the proper conversation at the appropriate time is critical for creating meaningful mentoring interactions. Carefully designed stages provide insight into which types of conversation are applicable at any given time along the process in your unique journey. 

The primary intention when determining the proper conversation to engage in is confidence. The model’s emphasis is to progress from low confidence to high confidence by maintaining effective communication that is open, honest, and supportive. 


Confidence in the context of mentorship means the degree to which you feel sure of yourself and your abilities. It’s a belief in one’s own capability of achieving desired results. It also has a lot to do with trusting and relying on the guidance that is being shared. By engaging in the right mentoring conversations, trust is gained and increases one’s confidence to take action.      

Failure to build confidence can lead to the following:

  • Blind Spots occur when different priorities are placed on the primary direction or purpose of the conversation. This leads to conflicting agendas and frustration. Blind spots waste time and cause unexpected surprises later in the conversation.
  • Looping Conversations occur when there is no common understanding or agenda to keep the conversation centered. This leads to misunderstandings and repeated assertions. Conversations that loop once or twice are not necessarily bad, but if you find yourself looping continuously, it may indicate that a shared orientation has not been established.
  • False Assumptions occur when individual expectations are predetermined or undiscovered. They can lead to misunderstandings regarding goals, motives, attitudes, and developmental aspirations. False assumptions can also lead to unintended destinations and mistakes that cause you to create solutions for problems that don’t exist. 

Three Mentoring Conversations

When considering mentoring conversations, three distinct modes come into view. Each one defines a type of conversation that builds mutual understanding, reciprocated trust, and meaningful results. The three mentoring conversation modes are Awareness, Exploration, and Preparation. 

Awareness Conversations

You find yourself in an awareness conversation when there is a low understanding of what can be accomplished. 

Most mentoring relationships begin with building awareness to uncover ideas and challenges characterized by low confidence in accomplishing successful outcomes. Taking the time to develop a mutual understanding of where the conversation is headed will increase confidence and build trust. 

When starting a new journey in an unfamiliar land, it is advisable to get your bearings and assess possible routes forward. Likewise, the objective of awareness conversations is to get oriented to the lay of the land before exploring developmental options. Conversations, like journeys, tend to be pleasant and productive or difficult and unproductive. A poor conversation is hindered by confusion, missed opportunity, and wasted time. On the other hand, a high-quality conversation often brings a sense of discovery, relational bonding, and fulfillment. Therefore, the determining factor for the quality of the mentorship experience often depends on how well you begin.  

More mature relationships, those farther along in the process, can also benefit from awareness conversations. 

Indicators that you could benefit from building more awareness in your mentoring relationship.

  • When you suspect that you are not on the same page and need to align on a direction forward
  • When you sense a lack of motivation or interest in the topic or subject under consideration
  • When you want to reset expectations for what can be accomplished

To gain new awareness, spend some time getting oriented to where everyone stands, what they bring to the conversation, and what they want as a result. Awareness conversations move mentorship from a general and abstract level to a personal and practical level of sharing. 

Best practice recommendations for building greater awareness.

  • Build Rapport – Push into areas of common interest. These areas can be secondary to the purpose of the relationship, but it helps to build interpersonal interest and familiarity.
  • Discuss Motivations – Reach out and connect by understanding intentions and future desires. Knowing what others want from the relationship can give you a greater sense of what needs to happen for everyone to feel satisfied with the outcome.
  • Outline Understandings – Clarify and recap important points, contributions, and understandings as they emerge in the conversation. This helps to define what is known and unknown.

Helpful Questions: 

Meant for gaining familiarity with the needs, history, and aspirations of all involved.

  • What are your interests?
  • What do you have experience in?
  • What are your career goals?
  • What do you expect to accomplish?

Exploration Conversations

You find yourself in exploration conversations when you’re evaluating the possibilities once you understand the direction you’re headed. 

Again, confidence increases by investing in discovering different alternatives and finding those that show promise. Discussing alternatives and exploring potential scenarios opens up novel ideas and ways to achieve dreams. It all starts with expanding horizons and examining different avenues that may lead to success—adding to self-knowledge and greater awareness of realistic possibilities. Exploring alternatives and different developmental paths throughout your mentoring relationship is advisable. 

Indicators that the time is right for an exploration conversation.

  • When you are oriented (know where you are) but don’t know where you want to end up
  • When no current option seems appropriate
  • When there are too few or too many possibilities
  • When you want to challenge assumptions
  • When you are about to repeat a worn-out pattern

Exploration conversations aim to generate possibilities and narrow the options to the most practical. Therefore, it’s best to separate the activities and add to the options that hold promise. Then, spend some time examining each option before narrowing your choices to a select few. 

Best practice recommendations for exploration conversations.

  • Generate Possibilities – Brainstorm ideas, extend known options, be flexible and remain open to discover new avenues for consideration. By diverging from the common or known path of options, you increase the likelihood of innovating or creating unique potential.
  • Determine Value – Discuss what appeals, fits, or seems most appropriate for each option. Then research and investigate to begin to form a clearer opinion.
  • Narrow Options – Establish criteria and clarify objectives and intents to help you narrow your field of options. By identifying actionable paths for collaboration, you gain focus and increase the likelihood of generating productive conversation.

Helpful Questions: 

These exploring questions are intended to help you consider available paths of action and qualify viable choices.

  • What have others done?
  • What are the different directions we could move in?
  • What new understanding can we gain?
  • What are the top three considerations?
  • Which ones hold the most promise?

Preparation Conversations

You find yourself in a preparation conversation once the desired destination is in clear view and after a course of action has been established and committed to. 

Without preparation, oftentimes people defer to the first method that makes sense to them or the most familiar one they happen to be comfortable with. Having a conversation to outline the steps that lead to the desired outcome increases the likelihood of taking the best course of action with complete confidence.

There is a big difference between having an intention to do something and preparing to do something. Preparation is often the difference between a hoped-for aspiration and a dream fulfilled. 

Preparation conversations are helpful throughout a mentoring relationship anytime a series of committed actions are under consideration. Sometimes, the preparation itself causes some to realize just how ready they are to take the next step in their journey. 

Indicators that the time is right for a preparation conversation.

  • When you want to consider your options for goal accomplishment
  • When you want to gain commitment for the next steps
  • When you want to consider the time and effort necessary to reach a goal
  • When you want to determine the skills (resume alignment, interviewing, etc.) to practice, that will help you gain confidence and ensure success

Best practice recommendations for preparation conversations.

  • Identify Activity – Discuss the appropriate actions to move toward goal accomplishment. By listing out the relevant tasks or activities that lead toward the goal, you can learn about avoiding common pitfalls and obstacles.
  • Plan the Sequence – Once you have established a course of action or series of tasks, determine the appropriate sequence. You may discover concurrent activities or critical dependencies will affect the order.
  • Set Measures – Lastly, consider how you will know success has been reached. It is best not to set outcome goals (like a promotion) but rather measure performance gains (i.e., improved understanding or ability). By determining measures, you transform good intentions into achievable goals.

Helpful Questions:
These preparation questions can help you determine a committed course of action.

  • What are the necessary next steps?
  • What are we willing to do?
  • How does this align with the hoped-for results?
  • Will this fit into the expected timeline?
  • What will success look like?

Which conversation mode do you find the most challenging, and why?

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