Mentor Meeting: Making the first one count

Mentoring helps to guide people through the unknown whilst embarking on a new working relationship with somebody and trying to figure out a career path. Here's how to make your first meeting count.

Nick Saraev

Published on 

September 9, 2022

Updated on 

Time to Read

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You've heard about the incredible benefits that come from mentorship; the professional development, the increased confidence, and even the potential for career advancement. 

But here's something you might not have been aware of: when mentors and mentees don’t have a clear direction, only one in three pairings are a success. 

That's why we're here – to give guidance on how to make the most of your very first mentor meeting. 

By following the tips below, you can create a productive, positive relationship with your mentor or mentee that will last for months (or even years) to come.

Mentoring session agenda templates

A quick checklist to prepare for your first mentorship meeting

The first meeting with your mentor or mentee can feel like a daunting – and indeed, critical – event. 

What will you talk about? Will you like them? Will they get along with you? 

There's a lot of pressure on this first meeting to establish the tone and trajectory of the relationship. 

One of the keys to success in these first crucial stages is preparation. You wouldn't go into an important business meeting without knowing what you want to achieve, so why would you go into a mentorship meeting without any direction? 

Here's a quick checklist of things to do, or at least think about, before your first mentor meeting:

  • Define your goals. What do you hope to achieve from this relationship, and from the first meeting itself? You may want to ask your mentor for help with a specific project, or you may simply want to get to know them better and learn about their career journey. 

If you're the mentor, your goal might be to better understand your mentee's motivations or to offer advice and support around a particular challenge they're facing. Either way, it's important to have a focus.

  • Collect your initial thoughts. In the lead-up to the meeting, find as much information about the other person's professional career as possible, and make a note of any specific questions you want to ask. 

For mentors, this might be things like, "What are your long-term career goals?" or "What do you think is holding you back from achieving these goals?". For mentees, it could be questions about the mentor's experiences in leadership roles, or how they overcame particular challenges in their field. 

  • Plan for logistics. It's a great idea to go into your meeting with a calendar of your weekly commitments; you'll likely be setting regular meeting times with your mentor or mentee, and it's important to make sure these fit in with the rest of your schedule. 
  • Prepare some resources. If there's something specific you want to achieve from the meeting, it can be helpful to come armed with some resources. This might be a presentation or article you want your mentor to look over or a list of challenges you need help with. 

Remember, too, that the first meeting is often less content-filled and more get-to-know-you style; your mentor or mentee might want to know more about you as a person and what makes you tick. Feel free to relax into the meeting and let the conversation flow naturally.

How to nail your first mentor meeting (tips and advice)

So, you've successfully prepared for the first meeting with your mentor or mentee – but what about the meeting itself? How can you make sure you make the most of this valuable opportunity? Let's dive into some practical tips.

Be prepared

This might seem obvious, but it's worth reiterating; if you're disorganized or unprepared, it'll reflect poorly on you and may make your mentor or mentee less likely to want to meet with you in the future. Preparation sets the trajectory for a successful mentoring relationship.

Make sure you know where you're meeting, what time, and have everything you need (including any resources or questions you want to discuss). Mentally tick off the following:

  • Do I have a solid understanding of my goals for this meeting and for the mentoring relationship as a whole? 
  • Have I prepared questions to ask my mentor or mentee? 
  • Do I have an idea of what topics we might discuss based on my research into their professional background? 
  • Am I bringing anything with me to the meeting, like a presentation or article? 
  • Have I considered what my mentor or mentee might want to know about me, and am I prepared to talk openly about myself? 

If you can confidently say yes to all of the above, you're in good shape.

Email an agenda ahead of time

Roughly 70 percent of time spent in meetings is wasted or misused, which is a scary statistic – but the waste can be avoided with simple steps, like sending an agenda ahead of time and preparing your responses in advance.

An agenda doesn't have to be long or complicated; simply jot down the topics you want to discuss, and make sure your mentor or mentee has a copy before the meeting begins. This will help keep things on track and ensure that you make the most of your time together.

If you're meeting to discuss career goals with your mentee, for instance, the agenda might look like this:

  • Introductions 
  • A discussion of the mentee's career goals 
  • Identifying any challenges or roadblocks in achieving these goals 
  • Brainstorming possible solutions and next steps 
  • Wrapping up and setting a date for the next meeting

Within the agenda, feel free to include more specific points you'd like your mentor or mentee to address. The key is to be clear and concise so that everyone knows what to expect.

Build rapport

The day has arrived. You're in the meeting, getting to know your mentor or mentee. How can you make sure that the conversation flows and that you build rapport?

First, resist the urge to talk about yourself too much. It's important to share information about who you are and what you're looking for in a mentor relationship, but try to focus on your counterpart as well. What are their goals? How can you help them achieve them?

Be a good listener, too – and be proactive about it. This involves not just hearing what your mentor or mentee is saying, but really listening and trying to understand their perspective. Ask follow-up questions, and make an effort to remember the answers for future reference.

Finally, try to be yourself. Be authentic, honest, and trustworthy, and show that you're interested in building a long-term relationship. If your mentor or mentee feels like they can trust and confide in you, it'll go a long way in solidifying the bond between you.

Clarify boundaries

Mentoring relationships can be tricky to navigate because they're built on trust and intimacy. It's important to set boundaries early on. Said boundaries aren't meant to be restrictive or to limit the relationship in any way – rather, they're designed to ensure that both parties feel comfortable and know what to expect from each other.

Some examples of boundaries you might want to set:

  • I'm happy to meet for coffee once a month, but I can't commit to anything more frequent than that. 
  • I'm not comfortable discussing my personal life with my mentor/mentee. 
  • I'm happy to provide advice and resources, but I expect my mentee to take the lead in implementing them. 
  • If there are any red flags or concerns, I'll bring them up directly with my mentee, rather than going to a third party.

These are just a few examples – ultimately, it's up to you and your mentor or mentee to decide what boundaries are necessary and appropriate. The key is to communicate openly about your expectations.

Establish roles and responsibilities

If you are the mentor, you will have different expectations and responsibilities than if you are the mentee. It's important to establish these roles and responsibilities early on.

As the mentor, you might be responsible for:

  • Providing guidance and advice 
  • Sharing your experiences and expertise 
  • Helping your mentee identify their goals 
  • Connecting your mentee with resources 
  • Giving honest feedback 

As the mentee, you'd be:

  • Setting goals and taking action steps to achieve them 
  • Sharing progress and challenges with your mentor 
  • Listening to your mentor's advice and guidance 
  • Taking responsibility for your own success

The beauty of a mentoring relationship is that it's flexible. You can always adjust the roles and responsibilities as needed, as long as you keep the lines of communication open.

Ask lots of questions

The success of your mentorship pairing is incredibly dependent on the quality of your relationship. And what is the foundation of any good relationship? Sharing an understanding of each other's needs and expectations.

When you're first getting to know your mentor or mentee, ask lots of questions. Ask about their life; their career; their ambitions and hopes for the future. The more you know about each other, the easier it will be to identify areas where you can help each other grow.

And don't forget to ask your mentor how they like to communicate. Some people prefer to text or email, while others prefer face-to-face meetings or phone calls using something like a PBX phone system.

Take time for planning

At the end of your meeting, it's always a good idea to spend a few minutes planning for your next meeting. This way, you can make sure that each meeting is productive and covers the topics that are most important to you.

Underpromise and overdeliver

This can sound counterintuitive, but it works; when you set the bar low, you're much more likely to achieve your goals and come through for your mentor or mentee.

What you want to avoid at all costs is making promises you can't keep. If you overpromise and underdeliver, your mentor or mentee is likely to be disappointed – and that's not a good foundation for a strong relationship.

Meet up as often as possible

The more frequently you meet, the better. If you can, aim to meet up once a week or even more often. These regular check-ins will help keep your relationship strong and ensure that you're both making progress towards your goals.

Remember, a mentoring relationship is a two-way street. Both the mentor and mentee should be equally invested in making it work; if you're consistently giving more than you're receiving, it's time to have an honest conversation about what's not working.

Enjoy the process!

Mentoring can be an incredibly rewarding experience for both parties. So savor the moments, enjoy the process and watch as you both grow and learn from each other.

A sample agenda for future mentor meetings

To help you prepare as well as you possibly can for your first mentor meeting, we've included a sample agenda below. Feel free to use this as a starting point and adjust it to fit your needs.

Purpose of the meeting

This meeting will serve as an opportunity for us to get to know each other better and start working towards our shared goals.

Discussion topics for the meeting

In the meeting, we will discuss:

  • Our goals for the relationship
  • How we will communicate with each other
  • What our meeting schedule will look like
  • What resources or assistance you need from me
  • What I can expect from you
  • The ground rules for our relationship

Questions to ask one another

From mentor to mentee:

  • What goals do you have for your professional development?
  • What was a professional milestone you’re most proud of?
  • Have you had any defining moments that you’d say have shaped your career path?
  • What are your 1, 3, and 5-year career goals?
  • What skills do you want to develop throughout our mentoring sessions?

From mentee to mentor:

  • What do you enjoy most about your current role?
  • What are the biggest challenges you’re facing in your role?
  • What has been the most rewarding experience in your career thus far?
  • Who have been some of your mentors throughout your career? How did they help you?
  • What skills, if any, do you feel confident in sharing with me?

Meeting success indicators

If the meeting is successful, we will have:

  • A clear understanding of each other's goals, expectations, and boundaries
  • A communication plan in place that works for both of us
  • A meeting schedule that we're both comfortable with
  • A mutual understanding of what resources and assistance we can provide for each other

Wrapping up the agenda

If you leave the meeting feeling like more needs to be discussed, that's perfectly normal. The first mentor meeting is usually just a starting point for deeper conversations that will happen in future meetings.

With an agenda like this, you and your mentor will be able to hit the ground running and start making the most of your relationship right away.

Managing a mentorship program? Try Together

The example agenda above is a snapshot of the resources we provide our mentors and mentees here at Together. Through our platform, mentorship pairs and groups are guided through the entire process – from initial pairing to goal-setting and meeting scheduling, to reflection and feedback – ensuring that everyone gets the most out of the experience.

With powerful progress tracking features and customizable templates, Together makes it easy to manage mentorship programs of any size. If you're interested in learning more about our platform, we invite you to get started with a free trial today; we're passionate about making mentorship work for everyone.

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