4 Mentoring Session Guides to Plan Your Next Catch-up

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So you’ve had a few meetings with your mentor (or mentee) and likely worked through your first meeting checklist. That means you’ve covered the basics: you understand your mentoring partner’s background, experience, expertise, expectations, and goals.

Top Tip: If you’re struggling with the latter, you can get help setting your goals with ​Mentorloop’s goal-setting feature. This will help you both identify what success looks like for your partnership, ensure you’re on the same page, and build and maintain momentum together.

After you’ve gone through these exercises and had your first few meetings, however, it’s not uncommon that pairs get stuck — especially those that are new to mentoring. But don’t worry! Whether you’re at a loss regarding what to talk about or tackle next, or simply need some extra structure to your meetings in order to get the most out of them, our session guides are here to help.

The following mentoring session guides will help you keep up the good work by providing you with some structure for the next four sessions with your mentor or mentee, ensuring you feel confident, productive, and get the most possible out of your mentoring catch-ups.

Session Guides

You can use these mentoring session guides interchangeably, they don’t necessarily need to go in any specific order; use whichever one feels appropriate and/or as needed.


1. The Storyteller

Our brains love good storytelling. That’s because narratives are compelling, but also because they can actually change our beliefs, attitudes, and behaviours.

Not only can a story be inviting and exciting, but it can also better sustain a mentoring partner’s attention than some other methods, and can more effectively inspire your mentor or mentee to take action.

This type of approach is best for those who benefit from a free-flowing exchange. Offering stories can mean offering insights for your partner’s development. Remember, sometimes the best mentor is someone who shares experience rather than simply giving direct advice.

Storytelling
(20 minutes)
Share a story from your experience that relates to your mentoring partner’s goals or challenges.
Highlight the key takeaways and lessons from the story.
Discussion
(15 minutes)
Encourage your mentoring partner to ask questions or share their thoughts on the story.
Discuss how the lessons from the story can be applied to their situation.
Action Plan
(10 minutes)
Collaboratively identify specific actions or strategies to implement based on your discussion.
Set clear goals for the next steps.
Feedback & Closing
(10 minutes)
Provide feedback and insights on your mentoring partner’s progress.
Summarize the key points and action items from the session.

2. The Guru



Self-awareness is incredibly important to a mentoring relationship. After all, if you’ve signed up to impart your professional wisdom to someone else, you need to be in touch with how you have arrived at this point in your career and what steps you took—both personally and professionally—to get there.

Similarly, if you’ve signed up to receive this professional wisdom, it’s important to do some digging in order to uncover why, at this moment in time, you’ve made this decision. What about your personal and/or professional situation has led you to seek out mentorship and take the next step in your career?

Mentoring Partner 1:
Self-Awareness Exercise
(15 minutes)
Have one mentoring partner ask how the other thinks others/the world perceives them.
How do your actions and communication impact the way others see you?
What do you like about that perception, and what don’t you like?
Where do your strengths lie? Your weaknesses?
Mentoring Partner 2:
Self-Awareness Exercise
(15 minutes)
Switch roles, and now have the other mentoring partner do the same.
Discussion
(15 minutes)
Ask each other questions and share your thoughts on the previous exercise.
Discuss what you’ve learned and if you’d like to change anything.
Action Plan
(10 minutes)
Collaboratively identify specific actions or strategies to implement based on your discussion.
Set clear goals for the next steps.
Feedback & Closing
(10 minutes)
Provide feedback and insights on your mentoring partner’s progress.
Summarize the key points and action items from the session.

3. The Situation


This is all about situational awareness and using situations as a mentoring opportunity.

During this type of session, have each participant bring some situations to the table. If you’re the mentee: bring some past situations you could have handled better, or current challenges you’re facing that you’d like advice/input on. If you’re the mentor, share specific situations that have morales directly related to your mentoring partnership’s objectives/goals.

Situation Description
(10 minutes)
Describe the current situation or challenge you’d like to explore.
Situation Exploration
(15 minutes)
Ask probing questions to better understand the context.
Discussion and Analysis
(15 minutes)
Collaborate on analyzing the situation, and considering potential solutions, and/or strategies for handling it.
Action Plan
(10 minutes)
Identify specific actions and steps to address the situation.
Set a timeline for implementing the plan.
Feedback & Closing
(10 minutes)
Provide feedback on the chosen approach and action plan.
Summarize the key points and action items from the session.

4. The Skill-Builder

Use your mentor as a magical mirror—they might be able to see things you cannot.

After you’ve reviewed your strengths and weaknesses, focus on how exactly you can build up perceived weaknesses via both hard and soft skills. Which hard skills can you learn to take your professional game to the next level? What ‘soft’ skills (leadership, confidence, organisation, etc.) can you improve on? What steps should you take to better yourself in each category?

Identify the Skill
(10 minutes)
Identify the skill or competency to be developed and why.
Explore Skill-Building Options
(15 minutes)
Provide instruction, guidance, and resources to help your mentoring partner develop the targeted skill.
Offer examples and exercises for practice.
Explore external options for learning.
Practice & Feedback
(15 minutes)
If applicable, encourage your mentoring partner to practice the skill during the session and provide constructive feedback and suggestions for improvement.
Action Plan
(10 minutes)
Collaborate on an action plan to continue improving the skill outside of the session.
Set goals and milestones.
Feedback & Closing
(10 minutes)
Provide feedback on your mentoring partner’s progress and skill development.
Summarize the key points and action items from the session.

Work ​S.M.A.R.T., Not Hard

We hope you find these mentoring session guides useful for your next catch-up with your mentoring partner! And if you’re looking for more bite-sized guidance, check out our list of 73 Questions to Ask You Mentoring Partner.

Whichever of the mentoring session guides you choose to implement in your next mentoring meeting, ensure your goals are ​S.M.A.R.T. That’s to say, the feedback you’re providing is specific, measurable, achievable, relevant, and time-based. This will help both mentor and mentee be more clear on where your mentoring relationship stands and how it’s progressing towards your shared goals.

You can support your organisation by building a culture of mentoring – why not share this with your people-first advocate, today?

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Emily Ryan
Emily Ryan
Head of Marketing at Mentorloop. Observing tens of thousands of mentoring relationships, she is passionate about helping people get the most from their mentoring experience. When not writing, you'll find her brewing beer or globe-trotting.

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