A Mentor's Guide to 5 Top Tips For Smashing Your First Mentoring Session

Congratulations on taking the plunge and becoming a mentor! You’re about to embark on a journey that will challenge and inspire you. It’s a decision that will be incredibly rewarding not only for your future mentee (or mentees!) but also yourself.

During a recent poll, we discovered that 1/3 of the AllBright community think they aren’t skilled enough to be a mentor. This smells like imposter syndrome because anyone at all ages and stages can be a mentor.

Don’t worry – you’re not expected to have all the answers or be responsible for someone else’s success. Mentoring is all about providing the time and space for someone to explore their values, discuss challenges they may be facing, and gain new perspectives on the options available to them.

There’s no one-size-fits-all formula to mentoring because your mentor-mentee relationship will be unique. Don't believe us? Check out these that might surprise you. But to help ease that pesky imposter syndrome, here are our five top tips for smashing that all-important first mentoring session.

1. Remember the three Ws

Ensuring you’ve locked in the what, where, and when of your mentorship before your first session means you can dive straight into the good stuff during the time you have with your mentee. It also helps set boundaries and clarify expectations, which, as we cover in our , are two key foundations of a successful mentorship.  


What will this mentorship involve? What forms of communication work best for you? What areas can you offer insights, guidance, and expertise in?   

Top tip: the messaging tool on the AllBright platform is a great way of keeping all your Mentor Matching communication in one place. 


Where will you conduct your mentorship? From Zoom meetings to phone calls and coffee shops to co-working spaces, find a location you both feel comfortable communicating in.  


When will you hold your sessions? It can be tempting to overcommit or be overly flexible here, especially if you’re a first-time mentor with a case of imposter syndrome, so make sure you’ve identified clear windows of time that work for both sides equally. 

Remember, we recommend having an introduction session with your mentee to pin down your three Ws in advance.

2. Get your own story straight

It’s important to have a clear and objective understanding of your own story. Knowing your strengths is one of our . But knowing your weaknesses and failures is just as important. 

Sharing the good, the bad, and the ugly can be a really powerful way of forming an authentic connection with your mentee. What’s more, it’s likely your mentee will learn just as much from your failures and how you navigated them as they will from your successes and what you did to achieve them.

Want a helping hand? Check out our Academy course

3. Manage expectations on both sides

Setting expectations goes beyond the practicalities of the three Ws we recommend you tick off in your introductory session. It will also help to avoid an awkward ‘it’s not you it’s me’ conversation further down the line. 

Use your first session to understand what your mentee expects from the relationship and work collaboratively on managing those expectations. In other words, what can you actually offer them? What is reasonable for them to expect from you? 

Remember, the best teachers never stop learning. So, you should also identify what you hope to get from your mentee.Are there gaps in your knowledge they may be able to fill? Are you hoping for a LinkedIn recommendation at the end of your mentorship?

4. Get to know (like, really know) your mentee

We’ve said it before (in our ) and we’ll say it again – your mentorship needs to be treated like any other relationship. But let’s dig a little deeper. 

Leave your work personas at the door. Taking the time to get to know your mentee as a person, over and above their career goals, is essential for building a strong rapport and developing a deeper understanding of your mentee’s values, desires, and motivations. This will foster an environment in which your mentee will feel able to share candidly. 

Ask your mentee open questions about their experiences, achievements, challenges, and interests outside of work. Ask them about their communication style and how they like to receive feedback. Ask them why they want a mentor. Then, pay attention to what they tell you. 

Keeping their current situation and experiences in mind as you navigate future sessions will help you give meaningful advice and provide personalised solutions, rather than just thinking about what you would do in their shoes. 

5. Lend an (active) ear

Although leveraging your own story to offer advice and insights can be a powerful tool (they’ve requested you as their mentor, after all!), don’t spend sessions simply thinking of ways to respond to what your mentee is sharing. Instead, practice active listening. This means focussing fully on what your mentee is saying, rather than thinking about how you might respond. 

We’ve already covered asking open questions – but take it one step further by ensuring you avoid interrupting your mentee. Whilst we often do this to be helpful or kind, try to avoid it, even if you think they’re struggling to find the right words or think you know what they’re going to say. 

Top tip: Take notes to help you stay present in the conversation and stay focused on what your mentee is saying, rather than how you might interject.  

Instead, wait for your mentee to finish, then reflect back with phrases like, ‘what I’m hearing is…’ and ‘in other words, what you’re saying is…’ Not only will they feel validated and heard but they also now have the chance to correct anything you may have misunderstood.  

Active listening isn’t just for session one, it’s something you should practice throughout your mentorship and beyond.

Now you’re equipped with these five top tips for smashing your first mentoring session (and beyond), you’re ready to dive in.

We can’t wait to hear how you get on! If these tips have helped ease your imposter syndrome or made your first mentoring session a smash hit, drop us a comment below.