Kicking Off A Mentoring Relationship With Awareness Conversations

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The determining factor of a mentorship experience often depends on how well you begin.

One can say there’s a beginning to just about everything and anything. A point and place in time in which something starts. Mentoring is no different, with two individuals uniting in a relationship to take a specific course of action. Mentoring is a mutually beneficial relationship in which people come together to form meaningful connections that impact all parties involved.

Defining a relation(ship)

According to Merriam-Webster’s definition, the word relationship is the relation connecting or binding participants in a relationship: such as a specific instance or type of kinship. Well then, what does the word relation mean? -you may find yourself asking. It is the state of mutually or reciprocally interested (as in social or commercial matters). In the case of mentoring, it is a social state of being mutually interested.

Finding that common ground

In the professional work space, mentors and mentees generally find one another through a common field of work, career interests, or advancement within a shared industry. However, harnessing a common interest or professional industry is not enough to form a solid mentoring relationship. This is where awareness conversations should come into play and serve a vital role. To have a successful relationship between the mentor and mentee, they need to know each other and develop a mutual sense of trust and understanding. This is the foundation from which mentoring relationships need to be built. 

Establishing a solid foundation

“Building a relationship with a colleague from scratch can be difficult,” according to The New York Times Digital Mentorship Program. “Successful mentorship relationships are built on a joint commitment of shared growth and trust.” Developing mutual trust and understanding sets the groundwork for mentorship success. Trust can be rewarded and won through sharing and disclosing interests, experiences, goals and expectations to accomplish.

Reciprocating is important

Exchanging information for mutual benefit is what reciprocation is all about. Sharing and listening to one another, in turn, can lead to some very positive outcomes. Awareness conversations are crucial in this respect. The mentor and mentee need to get to know each other in order to have a better understanding of where the other person is coming from and where they’d like to be.

Having an open and honest conversation in tandem keeps balance and puts the other person at ease. Uncovering interests and shared experiences builds a common ground of understanding and familiarity between a mentor and mentee. Joint participation and contribution demonstrate that both parties are invested and become the springboard for respectful and productive discussion. 

Building confidence

Mentees are usually the party looking for validation and guidance. They need to build rapport with their mentor early on by discussing motivations and outlining understandings. Mentors, therefore, need to ask pertinent questions while also being sincere. Demonstrating respect and showing great care will increase confidence. Being interested and invested helps increase confidence as well. “At the same time, mentees benefit enormously when mentors bring their own stories into the conversation; mentors are, by definition, role models, and deliberate and thoughtful moments of self-disclosure can teach and reassure young people just starting out, and can make the relationship deeper and more productive,” Georgetown University

Forming the kind of relationship you’d like to see

Today’s ideal mentoring relationship is community-based, and we’ve previously referred to it as a give-getter type of mentorship. This means everyone can both be a mentor and have a mentor depending on the context of one’s career experiences. At one point in life, we’ve been a mentor, whether we realize it. Early mentors are typically parents, grandparents, or other family members. Every great doctor, lawyer, teacher, and business leader has honed their craft from someone who came before.

Don’t go rushing into anything

Through awareness conversations, a mentor can uncover challenges to accomplish success. A decent quantity of time and care needs to be dedicated to this early stage of development, informing the mentoring relationship. At this particular point in time, the mentoring process is delicate and can’t be rushed or forced. 

Keeping track of time

The quality of the time spent together while conducting awareness conversations must also be paid attention to. Time shouldn’t be wasted on frivolous topics of casual conversation. Instead, importance should be placed on designing an agreed structure of intent. Setting the stage by establishing how the relationship should work upfront will lead in your favor. It can be the deciding factor between being ultimately productive vs. unproductive in what you’ve set out to accomplish in the end.

Building upon the possibilities

Awareness conversations are all about exploring, developing options, and assessing the possibilities. How those conversations turnout sets the mentoring relationship up for either success or failure. Building awareness is essential, but not too worry; if any bumps or hurdles are experienced along the way, the best-laid plans are not going to waste. More mature and farther along with mentoring relationships sometimes lose sight, but engaging in awareness conversations can help you regroup and find your path or lead you on a new one.


Asking the questions below is a good place to start. 

Remember, awareness conversations are meant for gaining familiarity with the needs, history, and aspirations of all involved.

Mentees to mentor

  • What are your interests?
  • What do you have experience in?

Mentors to ask a mentee

  • What are your career goals?
  • What do you expect to accomplish?

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