Emmanuel is nervous. He has recently been promoted to a leadership role and although he is looking forward to his new stint, he is slightly perturbed about the expectations people have from him. Moreover, he has always relished working as an individual contributor and the recent elevation means he will be managing a team along with large scale projects and strategic alliances. To ease his anxiety and help strategically chart out a direction, he is assigned a mentor.  But he is unsure of how to structure his first conversation.

Stella is a first-time mentor. She is a veteran in the organisation and carries a reputation for building and leading teams, critical projects and stakeholder partnerships. Although she has had a hands-on experience in leading the organisation to great heights, the process of mentoring is a novel concept to her. She is equally nervous and in a similar dilemma as to how to lead the conversation.

What happens when the mentor and the mentee are both nervous about their first meeting?

It is almost like a blind date; you are excited but equally nervous!

Just like Emmanuel and Stella, have you felt a bit jittery about your first mentoring conversation and unsure of what to say or expect?

The first meeting can be a little daunting for the mentor and the mentee. But with the right preparation beforehand, you will be able to confidently take full advantage of the process.

Whether it is a one-time engagement or a series of conversations, someone who is committed to invest in your development should always be valued. At the same time, as a mentee prove to your mentor that you are worth their time and investment.

Here are some strategies for mentors and mentees to strike the right balance and ace your first conversation. 

1. Do your groundwork

Mentor – Planning the structure of your hour-long conversation in advance has its advantages whether it is the in-person introduction or a sending a short email intimating your mentee that you look forward to the meeting.  Think of how you’d like to articulate your professional exposure, stories and milestones. Be curious to know more about your mentee before you jump into mentoring subjects

Mentee – Each session with your mentor will last for an hour and therefore you want to gain as much as possible. Research about your mentor beforehand, read up their profile on LinkedIn and get insights into their professional exposure. Share your resume or a short professional summary before the meeting and make it easy for your mentor to know a bit about you

2. Map your intentions

Mentor – Most of the times, your mentee will have a laundry list of topics to discuss and goals to achieve. But it is upto you to help them prioritize the most pressing ones. Your mentoring engagement will likely be a short one therefore guiding the conversation towards the specific goals your mentee would like to achieve will keep the engagement on track.

Mentee – Your mentor match is likely to last for a minimum three months therefore be specific about your goals during this engagement. Articulate the topics you’d like to be mentored on and voice it to your mentor in the first conversation. If you aren’t sure of what you’d like to achieve, then that itself can be a topic for discussion

3. Be proactive

Mentor – Be open, generous and proactive about sharing your time, resources and guidance. Your mentee will likely see you as an inspiration, an industry expert and rely on your words and wisdom to meet their goals. You may not want to provide all the answers, instead, you play the role of a thought provoker to the mentee

Mentee – Take the initiative to respond to emails from your mentor, work on action items agreed during the meeting and also keep your mentor informed of your progress before the next meeting. By being proactive, you are demonstrating seriousness towards the engagement and show that you value and respect your mentor’s guidance in the process

4. Be open and transparent 

Mentor – A healthy dose of balance and openness in your conversation with your mentee breaks down any barriers they might have about being vulnerable. Be willing to share struggles of your professional journey that help your mentee drop their guard and voice any fears and apprehensions. Your willingness to be open and transparent will fetch receptivity to your feedback

Mentee – The more honest you can be, the more your mentor will be able to help. You don’t need to have everything under your control but by being open and transparent about your fears and limitations can fetch you the right feedback. Your mentor will appreciate your willingness to be vulnerable and help you with the right tools and strategies to meet your goals despite the odds.

5. Ask questions

Mentor – As crucial it is to listen well to your mentee; it is equally essential to ask the right questions and give mentees the room to express their thoughts. Have a balanced view of the issue or the topic at hand and steer away from subjective opinions. Ask yourself, “what would I do if I were struggling with this dilemma?”. Don’t hesitate to dig deep into your mentee’s psyche and explore their motivations towards a certain approach

Mentee – In the first session, explore whether your mentor is a good fit and adept at helping you in your professional direction. Don’t hesitate to ask questions and understand your mentor’s perspective on a variety of subjects. Observe their communication and the way they offer advice or opinions. As a mentee, it is your responsibility to find out how to get the most out of the engagement

6. Don’t take everything as gospel

Mentor – Not all your advice will be received in good faith. What worked for you may not work for your mentee even if the situation isn’t any different. Have an open mind for your ideas and perspectives to be critiqued. Your ability to be open to feedback will earn you the reputation of someone being receptive to diverse opinions.   

Mentee – We all have our own opinions and intuitively know if something is bound to work for us or not. If you feel that your mentor’s advice is not quite right, you can choose whether to act upon it or no. Nothing is right, wrong or perfect. It is about what meets the objective and what suits you too.

7. Walk the Talk

Mentor – Encourage your mentee to look at the big picture even if the details in the process are daunting and the road to success is a long and winding one. Get specific with goals they can achieve before the next meeting. Keep channels of communication open through phone calls and/or emails in between formal mentoring meetings. That way, your mentee feels accountable and also know that they have a sounding board should they face challenges in the process.

Mentee – Make sure you action the goals set during your discussion and meet the deadlines agreed. It is essential to walk the talk to make the most of your engagement. Eventually, it will be disorienting for the mentor to see the time and effort invested in helping you progress is not taken seriously.

Lastly, have fun! Mentoring is a wonderful space to learn new skills and experiences, develop our thinking capacities through the eyes of a wise one and at the same time connect and build lasting relationships.

When you find yourself in a similar situation as Emmanuel and Stella, these preparatory strategies will help you move past your nervousness and look forward to a stimulating conversation.

Good luck!


  • Hithakshi Kotyan

    Author | People Development Specialist | Harvard Member | Positive Psychology Coach

    Hithakshi is an Author and Senior Learning Specialist with Priceline Technology, India. She has worked and consulted global organisations to drive personal and workplace excellence. The underlying themes of her programs are rooted in the areas of Career Pivots, Self-Leadership, Personal Productivity, and Well-being. She is the author of "The Future of Work In An Evolving Economy", a Member of Leaders Excellence at Harvard Square and Business Intelligence Board Member at the Chief Learning Officer Publication. Hithakshi is a Certified Instructional Designer, a Positive Psychology Coach, and a Behavioural Interpreter.