Employee Development

Mentoring Can Be Difficult – Here’s How to Make It Work

By Sarah O’Brien

Mentoring colleague at work

Mentoring can be a struggle. Organizing a time to meet, understanding the ins and outs of effective communication between you and your mentee, establishing goals for your time together; all of these are reasons employees and employers fail to commit to mentoring relationships in the workplace.

On top of logistical struggles, a mentoring relationship can be awkward. It’s difficult to ask for and accept help, especially when the format for transference feels reminiscent of grade-school tutoring.

If you’re looking for excuses to avoid mentoring, you’ll find them, but the reality is that mentoring will give your company an edge on a number of fronts.

Mentoring initiatives develop your potential leaders, help companies retain top talent, create opportunities to facilitate learning across gender, ethnicity, generation, sexual orientation and culture, and will maximize your employees’ engagement levels. Mentorship programs provide learning opportunities from an entire range of diverse perspectives that are invaluable when developing your employees.

We’ve pulled together some tips so you can bypass the struggles of mentorship, and get to the good stuff that helps strengthen and develop your organization and your employees.

Create an agreement, build a plan, commit to the work

Outline your goals, and the roles of the mentor and mentee in achieving them. This is where you’ll discuss the cadence of your meetings, the expectations you have for working with one another, and establish exactly what it is you’re looking to obtain from mentoring.

The bulk of learning opportunities exist in the part of a mentoring relationship where you’re actively working. Agreeing to mentorship, scheduling and structuring your plans and goals are all well and good, but it’s the work you do towards reaching those goals that is the true fruit of a mentoring relationship.

Support the relationship

If you were mentored before, consider what you liked about the relationship. What worked? What didn’t? What would you like to have changed about your mentorship?

If mentoring is new to you, establish open communication with your mentee regarding what works and doesn’t work for them when communicating, when setting expectations, and when trying to learn or problem solve.

You’ll find that much like your friendships outside the office, you’ll need to become familiar with your mentee and their quirks. Consider networking opportunities, create intermediate goals, share examples from your own experience or industry best practices, provide consistent feedback and assist in particularly difficult issues or tasks.

Create challenges

Any L&D professional will tell you that learning isn’t facilitated by watching someone do a task, or being handed the answer every time you hit a snag. Real learning happens when you’re forced to use what you’ve learned in a real life situation. This is why quizzes, polls and other learning reinforcement methods are so effective at cementing knowledge.

Creating challenges for your mentee allows them to dynamically solidify what they’re learning. You can create challenges by:

  • Asking probing questions that require more than a “yes or no” answer
  • Focusing on activities where learning is centralized
  • Increasing exposure to the topics they’re being mentored on by providing books, links to articles or helpful discussion forums


What can you do, say, or show that will help your mentee envision and be motivated to move towards their desired futures.

This takes a little creativity on your part, as the mentor. Consider examples from your own career and journey. What can you look back upon as a catalyst moment? Examples can create those same catalysts for your mentees, and give them momentum towards accomplishing their goals.

Create opportunities for sharing a vision by building new plans, arranging for interactions with senior leaders, and encouraging your mentee to ask for feedback from everyone: their peers, their supervisors and other senior leaders.

Using some of these ideas can get your own creativity and motivation flowing as a mentor. The most important part of a mentorship is the relationship that is made so that outstanding levels of learning can be facilitated and shared. Some mentorships will inherently look different from others depending on the culture of your organization, team or existing relationship with your mentee. Don’t let the fear of making a meaningful relationship with your mentee get in the way of the potential success and ROI of beginning a mentoring program.

For more guidance on harnessing the powers of mentoring relationships, check out this short preview of “Make Mentoring Count: Facilitating Learning” from The BizLibrary Collection here:

Are you making the most of your leadership moments? Learn how to maximize coaching and mentorship opportunities in our Micro-Coaching webinar, approved for 1 recertification credit from HRCI and SHRM: 

Micro-Coaching webinar cover

Sarah O’Brien researches and writes on a variety of business topics, including workplace dynamics, HR strategies, and training trends and technology.