A mentor’s job within a mentoring program is to guide the dialogue in a way that encourages a mentee’s professional and personal growth. A great way to do that is to ask questions and show up with a genuine curiosity - something which can be hard to do if you feel like you're not sure what to discuss.

While questions are a great starting point, you don't want each session to feel like a job interview, or put too much pressure on your mentoring relationship. To make sure conversation flows naturally, we've outlined a few key ways to incorporate questions and guide the conversation throughout your check-ins.  

Set Mentorship and Employee Development Goals

Session one should be all about setting goals and figuring out what a mentee wants to get out of the employee mentorship program. It sets the tone for the whole mentor-mentee relationship.

It's always good to start with a discussion of the mentee’s accomplishments to make them feel a bit more at ease – not only will this show you've taken a personal interest in learning more about them, but they will also be reassured that your sessions wont all be about ripping them apart.

Starting off in an informal and friendly manner will also reflect well upon your general company culture, no matter whether you're speaking with a new employee or a more experienced employee.)

Beyond this positive ice breaker, here are a few things to consider:

• Career Goals: Find out your mentee’s goals for professional development – and ultimately help them figure out whether they are on the right path.
• Set both short- and long-term goals: Find out what your mentee wants to accomplish within the first 30 - 180 days of your relationship. It's also good to talk about long-term goals they may have for five years and beyond.
• Previous mentorship experiences: Discuss both your mentee’s potential experiences and your own throughout your career. Figure out what worked and what did not as a way to help guide your own relationship currently.

Talk About Professional Experiences

While mentors may have more experience, it is always good to find common ground so you can relate to your mentee. Sharing stories of personal professional experiences will allow mentors and mentees to explore potential shared experiences, and it will also serve as a way to get to know each other in the process. If you find that your professional experiences are quite different, do not panic. Find ways to relate through the use of specific skill sets, motivation, and emotional responses.

Here are a few topics to help guide your discussion:

• How it started: Talk about your first-ever job and why you loved it (or hated it).
• Career development: Both mentors and mentees can talk about how you got started on your career path and where you are today. Think about specific moments that have defined each stage of your journeys, or team members who have been your sounding board for ideas that lead you to success.
• Professional support system: Talk about the people each of you go to for support. If you have a tough day at work, a frustrating exchange with a co-worker, or want to tell someone about a huge win, who is the person (or people) you go to first? It could be a co-worker or even a friend or family member.
• Career Frustrations: Find out what frustrates your mentee most about their current role and what is keeping them from reaching their full potential. Help them either figure out solutions or shift in perspective.

It can be tempting to try to find common personal traits in the beginning. However, it is best to stick to discussions of professional experiences. Remember that this is a professional relationship and with different life experiences, it can be awkward if you find you have no hobbies or life stages in common. Those shared personal experiences will likely reveal themselves over time, but best to start on a positive professional note with guided questions.

Discuss Industry Trends

Our ability to be successful in our role is often tied to how well we understand the industry and where we fit in it. While this may feel like small talk, a great mentor can guide these discussions into dialogue about career direction and constructive feedback about a mentee’s skill set.

Here are a few ways to guide the discussion:

• Give it the meme treatment: “How it started… How it’s going.” The trajectory your industry has taken over time can shine a light on how necessary skills have also changed, how job prospects have changed as the industry shifts, and what it takes to succeed now vs. even a few years ago. It can be interesting to acknowledge how your career path will differ from that of your mentee.
• Industry fit: Find out whether your mentee always saw themselves working in this industry and why they what made them choose it.

How to Develop the Necessary Skills

A big part of an employee mentoring program is to help mentees figure out how they can forge a path moving forward by developing new skills to help them reach their goals. It is important to recognize the fact that these discussions should focus on constructive feedback rather than a focus on the negative.

Here are a few topics to help focus your discussion and create a meaningful dialogue:

• Identify how weaknesses have affected you: Do not overlook a great discussion about weaknesses and how you worked to overcome them. It will humanize mentors in the eyes of mentees and give mentees a chance to figure out what they need to work on.
• Change: If your mentee has stepped into a new role or has added new responsibilities, find out how they are adjusting and how they are adapting to the corporate culture.
• Leadership Skills: How can leadership development influence the skills your mentee needs to develop in order to succeed in the long-term – including how to communicate with their team?
• Communication: Mentees often have trouble with how to communicate with senior leaders. Whether it is to ask for a raise, how to present ideas in a meeting, or even how to interact in less formal settings, a mentor can give a mentee confidence to approach each situation.

Talk about the company

As part of an employee mentorship program, a discussion of how things are going within the organization is an important one. It can help to shape further discussion about career paths and skills development and lead to overall retention. This can also be a touchy subject because your mentee will need to trust that you will not use anything they share in a negative way.

Here are a few topics to explore:

• Personal contribution: Ask your mentee how they will contribute to the long-term success of their immediate team and the organization overall. If aspirational, how can they develop the skills to get there?
• Organizational fit: How we see ourselves can often be different than how others see us. Find out how your mentee sees themselves fitting-in long-term. Then see how your view point matches with theirs and why there may be different perspectives.

If you are still stumped, try starting each session by writing down three questions each that you would like to talk about. Explore both the answers and the reasoning behind why either the mentor or mentee asked the question in the first place.

To get your mentorship program off to the best start, get in touch with one of our experts to see how our smart-matching algorithm and intuitive system can scale your programs AND remove admin burden.

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