Motivating someone to Mentor Is One of the Most Common Mentoring Challenges.
One of the most common challenges organizations faces while starting a mentoring program is getting the right mentors to participate. It’s hard to find an experienced person who wants to invest their time in shaping others’ futures. However, when there are many talented, inexperienced people ready to be mentored, the demand for mentors surpasses the supply.

Finding the right mentor-mentee pair
The most obvious requirement is matching mentees with mentors who can help achieve their goals. As humans, we gravitate towards others similar to us, so would mentor/mentee pairings based on race or gender help people connect better?
A mentoring relationship can fizzle before even engaging in any development because of a wrong match. That’s why finding the right mentor should be on the top of your priority list as a startup. Indeed, it isn’t easy to find the right mentor. Mentors who see themselves in their mentees are more likely to form a connection. A casual meet and greet to test compatibility would be a good starting point.
Mentor and mentee don’t have to have the same background and view on things. However, a different perspective and approach can be helpful for mentees and mentors.

Collecting honest feedback from mentees
Feedback is an essential aspect of a mentoring program. It helps you understand the progress of the program and the relationship between mentor and mentee. As direct involvement of the participant’s supervisor is not anticipated in a mentoring program, the program manager should collect feedback – at least once every three months – from both parties.
However, getting honest feedback from the mentee is not always easy. It’s common for a mentee to be reluctant, especially when the mentor is in a higher position in the organization.

Managing participants’ expectations
Expectations are natural in a mentoring relationship. Be it general or specif. Expectations are not articulated, they can lead to disappointment. Unrealistic mentoring expectations, too, can be a hitch in a mentoring relationship. It happens mentees think their mentor expected more from the relationship while mentors feel that their mentee expected too much.
This is the reason why it is vital to clarify expectations before starting a mentoring relationship. 

Mentoring challenges also include tracking the outcome.
The benefits of a mentoring program are no secret. But when you have a specific goal for a program, tracking its outcome becomes necessary. Mentors help mentees with career development, learning new skills, increasing self-confidence and making new professional connections. Most mentors are motivated by the satisfaction of helping someone and seeing them grow, but the benefits don’t end there. They also get to improve their leadership skills, gain exposure to new perspectives, build a long-lasting relationships and increase their knowledge through teaching. Mentors can use mentorships as a mechanism to force introspection of their strengths and weaknesses, allowing them to make the journey from self-awareness to self-actualization. As time goes by, support and learning become fulfilling. So, are all mentorships successful? Unfortunately, no. Negative experiences can stem from the mismatch of mentor-mentee, lack of mentor expertise, distancing behavior, manipulative behavior and general dysfunctionality. Mentorships are not a binding contract. If either party is unhappy, they should walk away from it without regrets. Because mentoring is a long-term relationship, keeping track of its success is critical