Mentorship 101: How To Structure The First Meeting & The Best Questions To Ask A Mentor | xoreni


MENTORSHIP 101: How To Structure The First Mentorship Meeting & Best Questions To Ask A Mentor | xoreni

Mentorship is something that I am so passionate about. It is a great opportunity to learn from someone more senior than you and hear about their experience + the mistakes they have made along the way.

Ever wondered what topics should you discuss in your first mentoring session? Are there any ‘rules’ that both mentor and mentee should follow? What are the mentee’s responsibilities?

Today I went through the proper way to structure the first mentorship meeting, some topics you can discuss, and some great questions to ask them. The questions revolve around mentorship in general, career progression and then some situational ones.

If you have anything to add that I missed, please leave it below. Let me know if this is helpful!


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xo, Reni ♡

Career Progression
– What do you wish you knew before you took your first management role?
– What was a pivotal step you took that propelled you into a management role? Do you believe getting an MBA is necessary?
– Was there ever a role you applied for and landed that you weren’t 100% qualified for? How do you approach it to ensure you don’t disappoint?
– How do I become a leader even if I’m not in a formal leadership position?
– What are some of the biggest mistakes you have made career wise that I should avoid?
– When you have outgrown your role but want to remain within the company, how do you position it to management without hurting the relationship?

Situational Questions
– My manager is constantly giving me surface level feedback, it is never constructive. How can I solicit more constructive, meaningful feedback from them?
– As someone in sales, what are your tips to sell someone on an idea you are pitching? Recently, I have been presenting projects to management, and I want to learn how to get buy in from key stakeholders.
– I tried to delegate a task last week and it didn’t go well. Can we work through what I can do differently next time?
– My performance review is coming up soon, what preparation do you most appreciate seeing from your employees?

General Mentorship Questions
– What do you value in a mentor and what do you value in a mentee?
– To you, what is the value of mentorship and how do both parties work together to make it mutually beneficial?

0:00 – Intro
0:44 – Things To Know Before Entering the Mentorship
1:10 – Introducing Yourself To Your Mentor
3:40- Question Time!
4:26 – Career Progression Questions
7:52 – Situational Questions
9:14 – General Mentorship Questions
10:05 – Ending The Meeting & Setting Future Meetings
11:59 – What To Do After The Meetings