Preparing for Your First Mentorship Session — What to Say, What to Ask, What to Bring
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Estimated time: 45 minutes

VIDEO OPENER SCRIPT

To be recorded by Ayomide Arowolo-Ayodeji, Founder of WAMIDO
Target length: 60 seconds
Tone: Warm, ceremonial, deeply personal

"Hey Pathfinder.

Welcome to the final lesson.

Six weeks ago, you opened your map for the first time. You did not know exactly what you were walking into. You just knew you wanted something more — more clarity, more direction, more capacity to build the life you could feel pulling at you from somewhere ahead.

You have done the work.

You know who you are. You know what you value. You know how to sustain yourself, how to build relationships, what mentorship really is, how to communicate with presence and precision, and how to think strategically about where you are going.

Everything — every lesson, every workbook exercise, every reflection, every uncomfortable honest moment — has been leading to what happens next.

Your first mentorship session.

And I want you to walk into that room — or onto that call — not with hope.

With preparation.

Because hope is what you have when you are not ready.

Preparation is what you have when you are.

You are ready, Pathfinder.

This is how you finish.

Open your map. One last time. Let's go."

LESSON OPENING: THE HOOK

In 1985, a young woman named Ursula Burns was working as a mechanical engineering intern at Xerox Corporation in New York.

She was twenty-seven years old. She had grown up in a housing project on the Lower East Side of Manhattan, raised by a single mother who took in ironing and ran a home daycare to put her children through school. She was one of very few Black women in technical roles at Xerox. She was, by most conventional measures, not someone the senior leadership of a major corporation would have had particular reason to notice.

But she had prepared.

Not just technically. Not just professionally.

She had thought carefully about who she was, what she was building toward, and what she genuinely needed from the people who were further along the path she was walking.

At a meeting where a senior Xerox executive was speaking, Burns asked a question.

Not a safe question. Not an impressive-sounding question designed to make her appear intelligent.

A genuine, specific, slightly uncomfortable question that challenged something the executive had said.

The executive, rather than being offended, was struck by the quality of her thinking.

He sought her out afterward.

That conversation became a series of conversations. Those conversations became a mentorship relationship. That mentorship relationship contributed directly to a career trajectory that eventually made Ursula Burns the CEO of Xerox — the first Black woman to lead a Fortune 500 company in American history.

She has spoken in multiple interviews about that first interaction and what she believes made it possible.

She was prepared. She had thought carefully about what she genuinely needed to understand. She had the courage to ask the question she actually needed answered rather than the one that made her look good.

And she showed up as herself — completely, without apology, without performance.

(Source: Burns, U., Where You Are Is Not Who You Are, Amistad Press, 2021)

That is the standard this lesson is asking you to meet.

Not perfection. Not performance.

Complete, genuine, fully prepared presence.

VISUAL ILLUSTRATION NOTE

For design team:
A young woman standing at the entrance to a large, formal meeting room. She is not intimidated — her posture is grounded, her gaze is forward, her expression is one of quiet, genuine readiness. In her hand, a notebook — not as a prop, but as evidence of preparation. Through the glass of the meeting room door, senior figures are visible in conversation. She is about to open the door. The moment is charged with possibility rather than anxiety. The light comes from inside the room — warm, available, waiting. The most powerful single image in the entire course. Warm, cinematic, quietly historic.

CORE CONTENT

Section 1: The Week Before — How to Prepare

The quality of your first mentorship session is determined largely by what you do in the week before it.

Not the hour before. Not the morning of. The week before.

Here is what that preparation looks like.

Research your mentor thoroughly.

Apply everything from Week 5, Lesson 5. Read every publicly available interview, talk, article, and piece of writing connected to your mentor's work and thinking. Understand their professional journey — not just the highlights but the arc. The transitions they made. The challenges they have spoken about. The questions they have raised publicly that have not yet been fully answered.

This research serves two purposes. It produces the specific, genuine questions that are the raw material of a great first session. And it communicates to your mentor, through the quality of your engagement, that you have invested real time and real attention in understanding who they are before you arrived.

A mentee who references something specific from their mentor's work in the first session communicates something that no credential or introduction can communicate.

They communicate that they were paying attention before they walked in.

Prepare your introduction.

Your mentor will want to know who you are. Not your CV summary — who you actually are. Where you are in your journey. What you are building toward. What has brought you to this specific moment.

Prepare a brief, honest, genuine introduction that answers these questions in three to four minutes.

Not a rehearsed speech. A prepared conversation. There is a difference.

A rehearsed speech sounds like a rehearsed speech. A prepared conversation sounds like a real person who has thought carefully about what they want to say.

The components of a strong introduction for a first mentorship session are these.

Where you are right now — your current situation, your field, your stage of development.

What you are building toward — the vision or direction you are moving in, connected honestly to why it matters to you.

Why this mentor specifically — what about their particular experience, perspective, or journey makes them specifically relevant to where you are going. This should be specific and genuine, not flattering and generic.

What you are hoping to develop through this relationship — not what you want to extract, but what you are hoping to build, learn, and become.

Prepare your questions.

Apply the full framework from Week 5, Lesson 4. Write at least seven genuine, specific questions. Then select the three or four that are most relevant to this specific mentor and this specific moment in your development.

The questions you bring to your first session should do three things simultaneously.

They should demonstrate that you have done your research — that they are specific to this mentor's experience rather than generic questions anyone could answer.

They should reveal where your thinking currently is — showing your mentor the actual terrain of your mind so they can offer guidance calibrated to your real situation.

And they should invite their experience rather than their opinion — asking what they have navigated and learned rather than what they think you should do.

Write your mentorship intention statement.

Return to the intention statement you wrote in Week 4, Lesson 1. Read it. Revise it if necessary. Know it.

You may or may not share it explicitly in your first session. But having it clearly articulated in your own mind will shape the quality of everything you bring to the interaction.

Prepare your My Map.

Bring your workbook to every mentorship session. Not to show your mentor every exercise you completed. As a personal reference — a record of the self-knowledge, the goals, the questions, and the commitments you have developed over six weeks that give your mentorship its foundation.

VISUAL ILLUSTRATION NOTE

For design team:
A preparation checklist illustrated as a warm, personal spread across two journal pages. Not a corporate checklist — a handwritten, slightly annotated personal preparation guide. Five items visible: Mentor Research, My Introduction, My Questions, My Intention Statement, My Map. Each item has brief handwritten notes beneath it. Some items are ticked. One is partially complete. The journal is open on a desk the night before the session — a lamp on, everything else quiet. The mood is one of focused, intentional preparation rather than anxious cramming. Intimate, warm, deeply personal.

Section 2: The Morning Of — How to Show Up

The morning of your first mentorship session deserves its own preparation.

Not because the rituals of a morning are magical. Because the quality of your internal state when you walk into that room determines the quality of your presence, and your presence determines the quality of everything that follows.

Apply the routines from Week 2, Lesson 4.

Honor your opening anchor — whatever brief, deliberate sequence of activities you built to begin your days with clarity and groundedness rather than reactive chaos.

If your session is in person, arrive early. Not obsessively early — ten to fifteen minutes. Early enough to settle into the physical space, to ground yourself before the interaction begins, and to communicate through your punctuality that the commitment matters to you.

If your session is virtual, apply everything from Week 5, Lesson 3. Camera at eye level. Clean background. Good lighting. Phone face-down. Every possible distraction eliminated before the call begins.

In the final moments before the session starts, practice the three-part grounding from Week 5, Lesson 3.

One deliberate breath. Feel your feet on the floor. Remind yourself: these are human beings, not judges. I am here to engage genuinely.

And then — one more thing.

Set your intention for this specific session.

Not a general intention to make a good impression. A specific intention for what you want this particular interaction to produce.

What do you most want to understand better by the end of this session?

What do you most want your mentor to know about you by the end of this session?

What is the one thing you most want to make sure happens in this conversation?

Write these down. They become your internal compass for the session itself.

VISUAL ILLUSTRATION NOTE

For design team:
A figure in the final moments before a mentorship session — shown in two simultaneous panels. Left panel: the external preparation — early arrival, notebook open, camera positioned, space calm and deliberate. Right panel: the internal preparation — one breath, feet grounded, intention set, expression one of genuine readiness. The two panels together communicate that preparation is both external and internal, and that both matter equally. Clean, warm, quietly powerful.

Section 3: In the Room — How to Conduct Yourself

You are in the session. Here is how to make the most of every minute.

Open with genuine warmth, not formal performance.

Your mentor is a human being. Begin the interaction as you would any genuine human connection — with warmth, with real presence, and without the stiffness of a performance.

A brief, genuine expression of appreciation for their time — specific rather than formulaic — is the right opening. Not "thank you so much for agreeing to mentor me, I am so grateful for this incredible opportunity." Something more real. Something that sounds like you.

"Thank you for making time for this. I have been looking forward to it since I read about your work on X."

Specific. Warm. Genuine.

Deliver your introduction clearly and concisely.

Three to four minutes. No more. Your mentor will ask questions if they want to go deeper on anything. Your role in the introduction is to give them enough genuine, specific information about who you are and where you are going to orient the entire conversation productively.

Transition to your questions purposefully.

After your introduction, the most natural transition into genuine dialogue is through your prepared questions.

Not all of them. The best two or three for this specific session, in this specific moment.

"I have been thinking about several things I wanted to explore with you, but I want to start with something specific. I have been navigating a particular challenge around X and here is how I have been thinking about it — I would love your perspective on what I might be missing."

This transition does several things simultaneously. It demonstrates preparation. It shows where your thinking currently is. It gives your mentor something specific and genuine to engage with. And it immediately elevates the interaction from a formal interview into a genuine dialogue.

Listen with complete attention.

Apply everything from Week 5, Lesson 2. Listen to understand, not to respond. Give your mentor the full quality of your attention. Take notes — not frantically, not in a way that breaks the flow of the conversation, but enough to capture the specific things that matter.

When something lands — when your mentor says something that genuinely shifts your understanding or raises a question you had not considered — say so. Specifically. Not as flattery. As genuine intellectual acknowledgment.

"That reframes something I had been thinking about completely differently. Can you say more about that?"

This kind of genuine response communicates something invaluable to your mentor. It communicates that the investment is landing somewhere real.

Ask the questions that matter, not the ones that impress.

In the moment of the actual conversation, the temptation to ask impressive-sounding questions rather than genuine ones will be real. Resist it.

The question you are slightly embarrassed to ask because it reveals what you do not know is almost always more valuable than the question designed to demonstrate what you do.

Manage the time with respect.

If you agreed to a specific duration, honor it. Watch the time. When you are approaching the end of the agreed period, acknowledge it and ask whether your mentor is available to continue or whether you should begin to close.

"We are coming up on the time we agreed to. I want to respect your schedule — are you able to continue for a few more minutes, or shall we begin to close?"

This question communicates something important. It communicates that you value their time as much as your own access to it. And it gives your mentor the genuine freedom to say either yes or no without feeling pressured.

Close with clarity and genuine gratitude.

In the final few minutes of the session, do three things.

Summarize the one or two most important things you are taking from the conversation. This confirms for your mentor that the session produced real value and gives you the opportunity to correct any misunderstanding before you leave.

Identify one specific action you are committing to take before your next session. This creates immediate accountability and signals to your mentor that what was shared will be acted upon.

Express genuine gratitude. Not excessive. Not performative. Specific to what this particular conversation produced.

"This conversation has given me a completely different way of thinking about X. I am going to do Y before we speak again. Thank you genuinely for your time and for your honesty."

VISUAL ILLUSTRATION NOTE

For design team:
A mentor and mentee in a session — the most fully realized human illustration in the entire course. Both figures are completely present. The mentor is engaged, animated, genuinely invested. The mentee is leaning forward, notebook open but eyes up, listening with the full quality of attention that six weeks of preparation has built. Between them, the space is alive with genuine dialogue — not a transfer of information from one person to another, but a genuine meeting of two minds at different stages of the same journey. Warm, intimate, quietly historic. This illustration should feel like the visual culmination of everything the course has been building toward.

Section 4: After the Session — The Follow-Through That Seals Everything

Everything you did in the session can be amplified or undermined by what you do in the twenty-four hours that follow.

Here is what the follow-through looks like.

Send the follow-up within twenty-four hours.

Apply everything from Week 5, Lesson 1.

A brief, genuine, specific message that references something particular from the conversation. Not a generic thank-you. Something that communicates you were genuinely present and that what was shared is still alive in your thinking.

Here is what a strong post-session follow-up contains.

A specific reference to something your mentor said that genuinely landed — one sentence that shows you were paying attention.

A brief statement of the one specific action you committed to taking — making the commitment public and creating immediate accountability.

A genuine expression of appreciation — one sentence, specific, not excessive.

And if appropriate, a brief indication of when you intend to follow up next — communicating that you are driving the relationship rather than waiting for them to.

The entire message should be no longer than five to seven sentences.

Here is an example of what this looks like in practice.

"Thank you for the conversation today. What you said about the distinction between building for impact and building for visibility completely reframed how I have been thinking about my next step — I am still turning it over. I am going to spend the next two weeks doing the specific research you suggested before I make the decision we discussed. I will report back when I have something concrete. Thank you genuinely for your time and your honesty."

Five sentences. Specific, warm, accountable, forward-looking.

That message takes four minutes to write. The impression it leaves lasts significantly longer.

Write your session notes while the conversation is still fresh.

Within a few hours of the session, expand your in-session notes into a fuller record of what was discussed, what was decided, what questions remain, and what actions you committed to.

This record becomes the foundation of your preparation for the next session. A mentee who arrives at their second session with clear, specific references to what was discussed in the first communicates something that very few mentees ever communicate.

That the investment is compounding.

Take the action you committed to.

Whatever you said you were going to do — do it. Before your next session. Before you have any other follow-up contact with your mentor.

The action you committed to is the most important thing this lesson can ask of you.

Not because the specific action will necessarily produce the specific outcome you hope for. But because taking it — attempting it, learning from it, bringing the result back to your mentor — is how you transform a mentorship session from a pleasant conversation into a genuine instrument of change.

VISUAL ILLUSTRATION NOTE

For design team:
A twenty-four hour timeline illustrated as a warm, purposeful arc. At the start of the arc, the session just ended — the mentee walking away with notes in hand, something alive in their expression. At the midpoint, the follow-up message being written and sent — deliberate, specific, warm. At the far end of the arc, the mentee taking the committed action — actually doing the thing they said they would do. The three moments connected by a single continuous line. The message: what happens after the session is as important as what happens in it. Clean, sequential, quietly powerful.

Section 5: The Long Arc — What You Are Actually Building

This lesson has given you the specific, practical preparation for your first mentorship session.

But it is worth stepping back, in this final section of the final lesson of the final week, to name what the first session is actually the beginning of.

Not a transaction. Not a series of useful conversations. Not a line on a CV or a name you can drop in a professional context.

A relationship.

One of the most significant kinds of human relationship available — the relationship between someone who has walked further and someone who is hungry to go further. Between accumulated wisdom and genuine hunger. Between experience and potential.

That relationship, when both people show up to it completely, when it is built on the foundation that six weeks of this course have been constructing — the self-knowledge, the well-being, the relational skills, the understanding of mentorship, the communication and presence, the strategy and vision — has the potential to be one of the most transformative experiences of your entire professional life.

Not because your mentor is extraordinary, though they may be.

Because you are ready.

You are ready to receive what is offered. Ready to act on it. Ready to bring genuine hunger, genuine honesty, and genuine presence to every interaction. Ready to drive the relationship with the intentionality and the discipline that makes a mentor's investment feel worthwhile.

You are ready to be the mentee that your mentor will remember.

Not the most impressive mentee. The most genuine one.

The one who showed up completely. Who asked real questions. Who received honest feedback without shutting down. Who acted between sessions. Who grew visibly across the arc of the relationship. Who eventually — maybe not at the end of this mentorship, maybe years later — sat across from someone younger and hungrier and chose to give back what they had received.

That is the chain.

And it runs from Garrison to Douglass. From Angelou to Winfrey. From Sullivan to Keller. From every mentor who chose to invest, to every mentee who chose to honor that investment, across every generation and every continent that this course has drawn from.

You are now part of that chain.

Go be worthy of it.

VISUAL ILLUSTRATION NOTE

For design team:
The final illustration of the entire course. A chain of human figures, each connected to the next, stretching across the full width of the frame. At one end, historical figures — suggested rather than explicit, ancient in posture, passing something forward. In the middle, contemporary figures — mentors and mentees of various African contexts, in dialogue, in connection, passing something forward. At the very end of the chain, a single figure — the Pathfinder. Receiving. And already beginning to look behind them at someone younger who is approaching.

The chain does not end with the Pathfinder.

It continues.

The most expansive, most human, most quietly epic illustration in the entire course. Warm, timeless, deeply African in its communal spirit. The visual embodiment of everything WAMIDO was built to create.

Workbook Exercise

MY MAP — WORKBOOK EXERCISE

Week 6, Lesson 4: Preparing for Your First Session

This is the final workbook exercise of the course. Take it seriously. Everything before it has been building to this.

Part A: The Research Record

Document your mentor research.

What have you read, watched, or listened to in preparation for your first session?

What specific things did you learn about your mentor's journey, their thinking, and their experience that are directly relevant to where you are right now?

Write at least one paragraph about what you now understand about your mentor that you did not know before you began the research.

Part B: Your Introduction

Write your three to four minute introduction for your first session.

Apply the four components from Section 1: where you are right now, what you are building toward, why this mentor specifically, and what you are hoping to develop through this relationship.

Write it. Read it out loud. Time it. Revise until it sounds like a real person talking rather than a prepared speech.

Then practice delivering it without reading it — not memorized, but internalized.

Part C: Your Seven Questions

Write seven genuine, specific questions for your first session applying the full framework from Week 5, Lesson 4.

At least three should be specific to your mentor's experience — questions that only they could answer because they are rooted in what you learned about their specific journey.

At least two should reveal where your thinking currently is — showing your mentor the actual terrain of your mind.

At least one should be a connection question from Section 3 of Week 5, Lesson 4 — a question designed to deepen human connection rather than extract professional information.

And at least one should be honest about what you genuinely do not understand.

After you write all seven, select the three you will prioritize in your first session. Write one sentence for each explaining why you chose it.

Part D: Your Session Intention

Write your three session intentions from Section 2.

What do you most want to understand better by the end of this session?

What do you most want your mentor to know about you by the end of this session?

What is the one thing you most want to make sure happens in this conversation?

Keep these somewhere visible on the day of your first session.

Part E: Your Follow-Up Draft

Write the follow-up message you will send within twenty-four hours of your first session.

You do not know exactly what will be discussed yet — so write it as a template with specific placeholders where the session-specific content will go.

For example: "Thank you for the conversation today. What you said about [specific thing] completely reframed [specific aspect of my thinking] — I am still turning it over. I am going to [specific committed action] before we speak again. I will report back when I have something concrete. Thank you genuinely for your time and your honesty."

Write your version. Make it yours. Make it sound like you.

Part F: The Full Circle

This is the final exercise in your map.

Go back to the very first thing you wrote in Week 1, Lesson 1, Part D — the three sentences you wrote to the version of yourself that would meet their mentor in six weeks.

Read what you wrote then.

Now write three sentences from the person you are today to the person you were when you wrote those first sentences.

What do you know now that you did not know then?

What has changed?

What are you carrying forward?

Closing & Summary

CLOSING REFLECTION

Ursula Burns walked into a meeting room at Xerox as a twenty-seven year old intern from a housing project on the Lower East Side.

She had no connections, no safety net, and no guarantee that the question she was about to ask would be received well.

What she had was preparation. Self-knowledge. Genuine curiosity. The courage to show up as herself without apology or performance.

And the willingness to ask the question she actually needed answered.

That was enough.

Not enough to make the journey easy. The journey was not easy. It never is, for anyone who is building something that genuinely matters.

But enough to begin. Enough to open the first door. Enough to start the chain of relationships and investments and challenges and growth that eventually produced one of the most significant careers in American corporate history.

You have spent six weeks building exactly what she walked in with.

Not her story. Yours.

Your self-knowledge. Your values. Your vision. Your relationships. Your communication. Your presence. Your strategy.

And now, your preparation for the room you are about to enter.

The mentor waiting for you on the other side of your first session is not there to save you.

They are there to walk alongside you for a season.

To share what they have learned.

To challenge what you think you know.

To open doors that you could not have opened alone.

But the walking — the actual movement through your own life toward the things that genuinely matter to you — that has always been yours to do.

It still is.

Go do it, Pathfinder.

With everything this course has given you.

With everything you have given yourself by showing up to it completely.

Go do it.

We are proud of you.

And we will be watching.

LESSON SUMMARY CARD

For design team: clean, shareable card

Week 6 | Lesson 4 | Preparing for Your First Mentorship Session

Three things to carry forward:

  1. Hope is what you have when you are not ready. Preparation is what you have when you are. The week before your first session is where the quality of that session is actually determined.

  2. In the room, be genuine before you are impressive. The question you are slightly embarrassed to ask is almost always more valuable than the one designed to demonstrate what you already know.

  3. The follow-up within twenty-four hours is not a courtesy. It is the act that transforms a single session into the beginning of a genuine relationship. Do not skip it.

Your Map exercise is waiting. It is the last one. Make it count.

WEEK 6 COMPLETE

For design team: the final module completion banner. Different from all the previous ones. More ceremonial. More expansive. This is the end of the course.

You have completed Week 6: Strategy and Vision.

You have completed the WAMIDO Mandatory Mentorship Preparation Course.

Six weeks.

Twenty-five lessons.

One map, filled with the most honest thinking you have ever done about who you are and what you are building.

You began this course as a person who understood the word mentorship.

You are finishing it as someone who understands what mentorship actually requires — of your mentor, of the relationship, and most importantly of yourself.

That understanding is rare.

What you do with it is up to you.

Your live session this week is the final one. It will bring together everything from Week 6 and close the preparation journey as a community. Come prepared to share what this six weeks has produced in you. Come prepared to celebrate what your fellow Pathfinders have built. And come prepared to step forward.

Your mentor is waiting.

The room is ready.

So are you.

See you on the other side, Pathfinder.

— Ayomide and the WAMIDO Team

Resources

RESOURCES

📺 Watch
"How to Speak so That People Want to Listen" — Julian Treasure, TEDGlobal 2013
Already recommended in Week 5 and essential here as a final preparation resource for the verbal and presence dimensions of the first session.
Available at ted.com/talks

📺 Watch
"Dare to Dream, Then Do" — Various African Leaders, TED Africa Playlist
A curated collection of talks from African leaders, innovators, and thinkers — a reminder, in this final lesson, of the larger context into which every Pathfinder is stepping.
Available at ted.com/talks

📚 Read
"Where You Are Is Not Who You Are" — Ursula Burns, Amistad Press, 2021
Referenced in this lesson. Burns' memoir is one of the most instructive first-person accounts of preparation, genuine engagement, and the specific quality of showing up completely that produces extraordinary outcomes from ordinary starting positions.

📚 Read
"The Mentor Leader" — Tony Dungy, Tyndale House Publishers, 2010
Already recommended in Week 4 and worth returning to here as the final resource — a reminder, from the mentor's perspective, of what a fully prepared, genuinely engaged mentee means to the person who chose to invest in them.

📚 Read
"Originals: How Non-Conformists Move the World" — Adam Grant, Viking, 2016
Grant's exploration of how people with genuine ideas, genuine preparation, and genuine courage navigate the world — a fitting final book recommendation for Pathfinders stepping out of preparation and into action.

🎧 Listen
"Unlocking Us with Brené Brown: The Courage to Show Up"
Brown's exploration of what it means to show up completely — vulnerable, prepared, genuine, and without guarantee of outcome — is the most fitting final podcast recommendation for this course.
Available on Spotify and Apple Podcasts

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