First mentoring session step by step. How to start the mentoring process?

The first mentoring session often stirs up a lot of emotions – both on the part of the mentor and mentee. There is excitement, curiosity, but also uncertainty. Where to start? How to lead the conversation? What is worth talking about at the beginning so that the mentoring relationship has a solid foundation?

This is natural. The first meeting doesn’t have to be perfect. The idea is not to immediately set a detailed plan for the next months or “solve” all the mentee’s challenges. The most important thing is to create space to talk, get to know each other and build trust.

A well-conducted first session very often determines how the entire mentoring process will unfold. This is the moment when both parties test their expectations, communication style and whether they work well together. That’s why more and more organizations are trying to support participants from the very first meeting – providing them with agendas, preparation materials, sample questions or tips on how to build a mentoring relationship. Proper preparation significantly increases the chances of a successful start to the process.

Why is the first mentoring session so important?

Mentoring starts with a relationship. Even the best mentoring program or a well-matched mentor/mentee pair won’t work without trust, openness and a sense of security.

The first meeting lays the foundation for everything that happens later. It is then that the first impression is built, there is space to get to know each other and establish the rules of cooperation.

It’s also a good time to set the right tone for the relationship – less formal than a status meeting and more of a partnership than classic developmental feedback. Mentoring works best when both parties feel free to talk and genuinely engaged. In this article you can read more about how to talk to a mentor or mentee.

How to prepare for the first mentoring meeting?

Preparation does not have to be complicated, but it is worth taking a moment.

The mentee can think about what he or she comes to mentoring with. What does she want to develop? What challenge is she currently facing? What does she expect from the relationship? You don’t need to have ready answers for everything – just a general direction.

The mentor, on the other hand, can prepare some opening questions for the interview and think about how to talk about your experience in a way that will help build rapport. It’s not about presenting a resume, but rather about showing your perspective and thinking.

It also works well to take care of the meeting space itself – especially online. A stable connection, a quiet place and no distractions really make a difference.

In programs using Mentiway, participants do not have to start with a blank sheet of paper. The platform includes a first-meeting preparation form that helps organize expectations, development needs and topics for conversation even before the first session. This often makes the first meeting go more smoothly and allows you to move more quickly to a valuable conversation.

How can the first step-by-step mentoring session look like?

Although every mentoring relationship looks different, many first meetings follow a similar rhythm. More about mentoring sessions, their frequency, duration and the meetings themselves, you can read in this text.

1. Get to know each other and build comfort in conversation

In the beginning, it is worth simply getting to know each other.

This is a good time to briefly introduce yourself, your career path, interests or experiences You don’t have to get straight to your goals and challenges – sometimes a few minutes of looser conversation helps break the tension and get into a more natural dialogue.

Authenticity is of great importance in mentoring. The less formal the atmosphere at the beginning, the easier it is later to have an open conversation.

2. Talk about the purpose of mentoring

Once there is more freedom, you can move on to the question: why are we actually meeting in this relationship?

This is an ideal time for the mentee to talk about his/her needs, challenges and areas he/she wants to work on. Sometimes the goal is very specific – such as developing leadership skills or preparing for a promotion. Other times it’s more general: the need for a different perspective, support in decision-making, or to sort out further direction.

This is why the first session rarely ends with a ready-made set of SMART goals. Much more often it serves to understand the mentee’s situation and gather material for further work. In subsequent meetings, various types of development tools can be helpful, such as the Wheel of Life, value analysis, mind map or SMART technique. At Mentiway, participants have access to dozens of such tools and ready-made scenarios for working on goals.

The goal doesn’t always have to be specified right away. Often it only clarifies itself during subsequent meetings – and that’s okay, too. If you’re curious about how many goals to work on during the mentoring process, also read this article.

3. Establish rules of cooperation

This is an element that is often overlooked, but later proves to be crucial.

It is worth establishing a basic framework for cooperation:

• How often the meetings will be held,
• How long they will last,
• In what formula they will be implemented,
• What is the contact between sessions,
• What both sides expect from each other.

It’s also good to talk about confidentiality – that is, that what comes up during mentoring stays between mentor and mentee. Such clarity builds a sense of security from the beginning.

In many mentoring programs, this stage is supported by a mentoring contract. This is a document that helps to establish the most important rules of cooperation, roles, responsibilities and the way of communication. At Mentiway, participants can jointly discuss and accept the contract directly on the platform, making it easier to ensure transparency in the relationship from the first meeting.

4. Determine the first concrete steps

Finally, it’s a good idea to close the meeting with something practical

It doesn’t have to be an elaborate action plan. Sometimes all you need is one small task to think about before the next meeting, a specific reflection or a topic to explore in more depth next time. A mentoring contract is also worth considering. You can read more about it in this article.

The most important thing is that after the first session, both parties know what to do next.

It is also worth reflecting on the mentoring contract and planning to work on goals in subsequent sessions. In practice, many couples devote a significant portion of the second meeting precisely to clarifying the direction of development and setting specific mentoring goals. At Mentiway, participants have access to an extensive database of mentoring and development techniques to help guide them through this process step by step.

What to keep in mind during the first session?

The most common mistake? Too much pressure for a “perfect start.”

The first meeting does not have to be groundbreaking. It doesn’t have to end with a ready-made development strategy or a list of SMART goals spread out over six months. Much more important is creating a quality conversation. One after which both parties leave with the feeling: “this was a valuable hour and I want to come back for another meeting”.

It’s also worth remembering that mentoring works both ways. The mentor doesn’t just share knowledge – very often he also develops himself in the process. He gains a new perspective, exercises attentiveness, questioning and communication skills.

In practice, mentoring is developmental for both sides of the relationship. In reverse mentoring programs in particular, this exchange tends to be even more pronounced – junior mentees develop mentoring skills while benefiting from the support and experience of the other party. Research shows that mentoring brings real benefits to both mentors and mentees. We wrote more about it here: Benefits of mentoring for mentors and mentees – Study 2025.

The first session doesn’t have to be perfect. It just needs to be real

The best mentoring relationships very rarely begin with a perfectly prepared script. Much more often they start with a good conversation. From curiosity about the other person. From attentive listening. From questions asked with genuine interest.

If the first session succeeds in creating an atmosphere of openness, trust and partnership – this is really a very good start. The rest develops later.

Q&A: first mentoring session

How long should the first mentoring session last?

Most often from 45 to 90 minutes. This is usually enough time to get to know each other calmly, talk about expectations and determine next steps.

Do you need to already have a specific mentoring goal at the first meeting?

No. Many people come to mentoring with a general need for development or a sense that they want to get something right professionally. A more specific goal often emerges only during subsequent conversations.

Who should lead the first session – mentor or mentee?

Most often, the mentor helps structure the conversation and open the meeting, but mentoring is a partnership relationship. Involving both parties from the beginning is important.

What to do if the conversation at the first session does not stick?

This happens more often than you might think. First meetings can be stressful. It’s worth giving yourself space and some time. However, if after several conversations it is still difficult to build a relationship or communication, it is worth talking about it openly.

Is it worth preparing questions before the first mentoring session?

Yes – especially a few opening questions or topics you want to cover. You don’t need to prepare the entire script for the meeting, but a short preparation usually helps you enter the conversation with more peace of mind.