Preparing mentors for the first session: a 3-hour preparation workshop

Mentors are usually chosen because they’re successful at their jobs. But being a strong expert doesn’t make someone a good mentor. A 2–3-hour preparation session before the program starts clarifies mentors’ role, boundaries and core skills. This guide covers what to include in that session and offers a sample agenda.

Why preparation makes a difference

There are two strong pieces of evidence here. According to a TD Magazine article (2018) citing ATD’s mentoring research, organizations that train their mentors before or during the program find their programs significantly more effective at reaching learning goals.

The second comes from a randomized trial. In a study led by Christine Pfund with 283 mentors at 16 universities in the United States, 87% of trained mentors reported changing at least one behavior. In the control group, the figure was 42%. Mentees also observed more positive change in trained mentors. The study was done in an academic setting, but the message holds for organizations too: short, structured preparation changes behavior, even in experienced people.

Clarify the role: mentor, coach and manager

The session’s first job is to show what a mentor is and isn’t. Put the three roles side by side:

• A manager is responsible for performance, assigns work and evaluates it.
• A coach works on a specific goal or skill, usually without directing, by asking questions.
• A mentor is a more experienced colleague who shares their experience, broadens perspective and walks alongside the mentee on their career path.

CIPD’s coaching and mentoring factsheet emphasizes that mentoring relies on the same listening, questioning and reframing skills as coaching. It adds that mentoring works best when it goes beyond a senior person explaining how things work.

The mentoring functions summarized in Kram and Isabella’s work (1985) also offer a good framework. Career functions include providing visibility and steering toward challenging assignments; psychosocial functions include acceptance, counseling and role modeling. Show mentors that both sides matter.

Listening and asking questions

What mentors struggle with most is the habit of jumping straight to a solution. When Zenger and Folkman examined 360-degree data on 3,492 managers developing their coaching skills, they described the best listeners not as people who stay silent but as people who help the other person clarify their thinking and give them energy. Good listeners asked questions, made the other person feel safe and offered suggestions at the right time.

Have participants practice in pairs. One person describes a real work problem; the other only asks questions. Questions they can use:

• What matters most to you in this situation?
• What have you tried so far?
• Where would you like to be on this a year from now?
• What’s getting in your way?
• What’s the smallest step you could take tomorrow?

Goal setting and feedback

A mentoring relationship that starts without goals turns into casual chat. Teach mentors to set no more than three goals with the mentee. For each goal, they should ask: What do we want to change? How will we know we’re making progress? What do we want to see at the end of the cohort?

Give a simple structure for feedback:

1. Describe the situation. When and where did it happen?
2. Name the behavior. An observation, not a judgment.
3. Explain the impact. What did this behavior lead to?
4. End with a question. “How did you see it?”

Remind mentors that feedback goes both ways. Regularly asking the mentee, “Are these sessions working for you?” keeps the relationship alive.

Confidentiality, boundaries and referral

This is the most critical part of the session. David Clutterbuck writes that confidentiality in mentoring is never absolute, which is why its limits need to be discussed up front. According to Clutterbuck, what’s discussed is confidential, but information about how the relationship is progressing can usually be shared with the program.

Make these rules clear to mentors:

• Confidential: The personal and professional matters the mentee shares.
• Can be shared: Whether sessions took place, the general state of the relationship.
• Exceptions: A risk to someone’s safety, legal obligations, harassment or discrimination.

A mentor is not a therapist. The University of Washington’s guidance, based on Lois Zachary’s work, also stresses that mentors aren’t expected to help outside their areas of expertise and need to know when to refer. When mental health, serious personal problems or discrimination come up, the mentor directs the mentee to HR, the employee assistance program or the relevant specialist. In the session, give the names and contact details of these channels concretely.

Preparing for difficult moments

Work through short cases. For each one, have mentors answer in groups: “What would you say?”

• The mentee cancels three sessions in a row.
• The mentee complains about their own manager and expects the mentor to intervene.
• The mentee is about to make a career decision the mentor disagrees with.
• Sessions have drifted from the goals into casual chat.
• The mentor thinks the pair isn’t working.

After discussing the cases, share an example of a good response for each. For example, when the mentee complains about their manager, the mentor doesn’t take sides and doesn’t try to talk to the manager themselves. Instead, they might ask: “What’s within your control here? How could you raise this with your manager?” That way the mentor supports the mentee in solving the problem themselves. If the situation involves harassment or discrimination, the referral rule applies.

Remind mentors of this too: they don’t have to have an answer to every question. Saying “I don’t know, but let’s find out together who does” is a natural part of mentoring.

For the last case, remind them of the program’s no-fault exit rule: a pair that isn’t working can be ended, without anyone being blamed, by talking to the program manager.

Sample 3-hour agenda

Time	Section	Method
0:00–0:15	Opening: program purpose, schedule, what’s expected of mentors	Short presentation
0:15–0:35	Mentor vs. coach vs. manager	Group discussion
0:35–1:05	Listening and powerful questions	Paired practice
1:05–1:15	Break
1:15–1:40	Goal setting and the flow of the first session	Worked example
1:40–2:05	Giving and receiving feedback	Practice in threes (mentor, mentee, observer)
2:05–2:30	Confidentiality, boundaries, referral channels	Case
2:30–2:50	Difficult moments	Group cases
2:50–3:00	Close: tools, support channel, first step	Q&A

Don’t leave them on their own after the session

Preparation doesn’t end with a one-off training. Support mentors throughout the cohort:

• Short materials: A session card, a question list and an agreement template. In ATD’s 2023 research, 89% of organizations provide participants with tools or support resources.
• Mentor meetups: Have mentors share experiences in a 45-minute group session once a month.
• Someone to call: Name a program manager or experienced coach a mentor can call in a difficult situation.

To help mentors plan how to run the first session, you can use the free session card.

Sources

• Minting Your Mentors (TD Magazine, 2018) — organizations that train their mentors find their programs more effective
• Mentors Deserve Better Training (WCER, 2014) — results of the randomized study with 283 mentors
• Coaching and mentoring factsheet (CIPD) — the difference between coaching and mentoring, shared skills
• Mentoring Alternatives (Kram and Isabella, 1985) — career and psychosocial mentoring functions
• What Great Listeners Actually Do (Zenger Folkman) — the behaviors that set great listeners apart
• Confidentiality in mentoring (Clutterbuck) — the limits of confidentiality and its exceptions
• Mentor practice (University of Washington) — Zachary’s phases, the mentor’s boundaries and referral
• ATD Research: More Organizations Support Mentoring Programs — tools and resources provided to participants