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Mentees and Mentors: How to Ace Your First Mentor Meeting
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Mentees and Mentors: How to Ace Your First Mentor Meeting

Discussion topics, example questions, and general advice for mentorship meetings

November 17, 2020
Rob Lennon
Customer Education Lead at Hugo
Marketer and author with experience spanning a diverse 16 years in retail and SaaS startups across healthcare, mar-tech, and ad-tech, and productivity software sectors.

Your first mentor meeting should accomplish three simple goals for both mentor and mentee:

  1. Build familiarity and rapport.
  2. Set expectations for the relationship.
  3. Learn from each other.

Whether you’re the mentor or the mentee, exactly how you accomplish these goals in your meeting is up to you. But for your first mentor meeting, it’ll help to have some best practices to lean on. 

So in this post, I’ll review, from both perspectives, what you’ll need to do to get the most out of your first mentor meeting. 

You’ll learn:

  • A simple but effective way to approach and structure your mentor meetings. 
  • What questions you should be asking your mentor or mentee.
  • How to lay the groundwork for a great relationship, with ideas for mentoring topics to discuss. 

Let’s get to it.

Preparing for and Structuring Your First Mentor Meeting

If you’ve read our blog before, you probably know how vital meeting prep is. With your first mentor meeting, this is as true as ever, especially for the mentee.

It’s good etiquette for mentees to make things easy on the mentor. For example, as the mentee, it’s on you to make sure the mentor has—at least—your resume and a professional summary. It’s also on you to give structure to the meeting and the relationship. 

Of course, that doesn’t mean everything’s on the mentee. Instead, mentors and mentees should work together to ensure meetings are productive.  But the general expectation is for mentees to take the lead in doing the legwork of scheduling meetings, outlining agendas, etc.

Regardless of who’s taking the lead, though, your first mentor meeting agenda should flow roughly like this:

  1. Build rapport: learn about each other, discuss personal and professional history, look for common ground.
  2. Discuss mentoring topics: such as skill-related, career story, situational advice, and leadership topics.
  3. Set initial expectations: tell each other what you expect from the relationship, figure out a regular meeting schedule, verbalize the mentee’s goals.

Assuming things go well, you can conclude your meeting by scheduling the next one.

Of course, this list is just a rough structure for your meeting. And you’ll need to fill it out based on your situation. So in the next few sections, we’ll go into more detail on building rapport, mentoring topics, and setting expectations.

Building Rapport 

Mentee-mentor relationships work best when there are openness and transparency. But it’s hard to be open and transparent before you’ve built trust.

People tend to trust the people they like and know. So dedicate most of the time in your first meeting to getting to know each other. Even if that means delaying pressing work or career issues you want to talk about, it’ll benefit you in the long run. 

One of the easiest ways to build rapport is for the mentor and mentee to swap professional stories.  

Most people enjoy telling their professional stories, especially to an attentive audience. Plus, mentors and mentees both benefit. 

Mentees gain valuable insights from a different, more experienced perspective. And mentors get to know their mentees so they can figure out how to best tailor their advice.

Choosing and Discussing Mentoring Topics

Depending on time constraints, you might not get into specific mentoring topics in your first meeting. But you—as the mentor or the mentee—should be prepared with at least one general topic area you’d like to discuss.

For mentees, the choice of mentoring topic flows directly from their goals. For example, maybe you need help figuring out how to develop your skills to make the next career step. If that’s the case, you’d want to cover skill-related topics. 

For mentors, it may be easier to choose topics once they’ve gotten to know their mentee. But that doesn’t mean mentors can’t come to the first meeting with some ideas. 

As a mentor, think about what you’ve experienced and seen. Merely giving your perspective on the industry or a specific job role can be invaluable for a less experienced mentee.  

For more ideas, look through the next two sections, which provide several mentoring topics and sample questions for both mentor and mentee to consider for discussion:

Mentoring Topics and Example Questions for Mentees

  1. Skill areas that the mentee wants to develop that the mentor already has. 
  • How can I improve my communication skills? 
  • Which skills areas should I focus on to advance in my career? 
  • Which skills do you think I need to improve on? 
  • How did you learn to _____?
  1. Career stories, lessons learned, and insights gleaned from your mentor’s career journey.
  • How did you get your start in ____? 
  • Was there anything you wish you knew or did differently when you first started? 
  • How did you reach your current position?
  1. Constructive feedback aimed at improving job performance and career advancement.
  • How could I have improved my presentation at ____?
  • Is there anything I should do differently to improve my performance?
  • What would you have done differently when _____ ?
  1. Situational advice to help the mentee address immediate, specific problems at work.
  • What methods have you used to inspire your employees in the past?
  • A certain employee continuously shows up late; how can I effectively address this?
  • How do I keep my employees focused while downsizing rumors swirl?

Mentoring Topics for Mentors

  1. Desired career path and goals to help the mentor tailor their advice.
  • What do you want out of your career?
  • How does your career role fit into your long-term career plan?
  • What’s missing (if anything) from your current role or career path?
  1. Leadership advice—for mentees that have recently moved into a leadership position.
  • How would you describe your leadership style?
  • What’s going well in your new role? What could be better?
  • Which of your typical communication methods has been the most/least effective for your team?
  1. Mentee’s long and short-term goals to help the mentor assist in developing an action plan.
  • What specific goals do you want to accomplish within the next 1 to 3 months?
  • How do you envision my role in helping you accomplish your goals?
  • What are your personal metrics for career success?

Setting Expectations for Your Mentorship

In the Harvard Business Review, Mark Horoszowski recommends that mentees create a structured accountability process. This, he explains, could be a simple one-page mentorship agreement that lays out meeting frequency, length, and relationship duration. 

Horoszowski suggests this step once you’ve had at least one meeting. But your first meeting can set the stage for your meeting agreement, helping to ensure it’s well-received.

So, as a mentee, start setting expectations by making a clear ask that shows your mentor you’re looking for more than a single meeting. 

Horoszowski suggests something like: “I’ve really enjoyed this conversation. Would it be okay if I followed up with you again in one month after I make some progress towards my goals?”

You can deliver this message in person, assuming it goes well. Or, you can follow up via email. 

Gameday: Your First Mentor Meeting

The good news on meeting day is that all that’s left to do is relax, get to know your mentor or mentee, and discuss each other’s expectations.

With a structured approach to building rapport, setting expectations, and discussing mentoring topics most relevant to you, you’re ready for your first mentor meeting.

Once the meeting is finished, mentees should thank their mentor and follow up on next steps.

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Rob Lennon
Customer Education Lead at Hugo
Marketer and author with experience spanning a diverse 16 years in retail and SaaS startups across healthcare, mar-tech, and ad-tech, and productivity software sectors.

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