The Power of the Initial Interview: How to Start Your Mentoring Relationship Strong

When you first meet your mentee, it can feel a little like a first dance—each of you finding your rhythm, wondering who leads and how to move forward. Now picture the opposite—a session where you already understand their goals, strengths, and the areas where they need your support.

That’s where the initial interview form becomes your best starting tool. It’s not just a sheet of paper—it’s a bridge that connects you to your mentee’s story. It helps you gain insight onto where your mentee has been, where they are looking to go, what drives them, and what’s standing in their way. goals, and challenges. It’s the very first tool in your mentor’s toolbox, and it can shape everything that follows.

In this blog, we’ll explore why the initial interview is essential, what to include in your form, how to make it meaningful, and how to use the information to guide your mentoring strategy. If you’re serious about mentoring well, don’t skip this step.

Why the Initial Interview Matters So Much

The first meeting sets the tone for the entire mentoring relationship. It’s not just about introductions—it’s about creating clarity, trust, and a shared sense of direction. The initial interview is your way to get all the basic information you need, but more importantly, it helps both of you get aligned on what success looks like.

Think of this form as your “map.” Just like a traveler needs to know where they are and where they want to go, your mentee needs to explore where they stand now, where they hope to be, and what might get in their way.

Without this understanding, mentoring sessions can drift off-course or become frustrating for both sides. But with a well-designed interview, you can immediately:

• Establish focus and direction: Without direction, mentoring sessions can become vague. But when you begin with the right questions—like “What are your top career goals over the next 5 years?”—you unlock meaningful dialogue. Together, you can build a plan that connects today’s conversations to tomorrow’s progress.

• Build trust and rapport: When your mentee sees that you’ve taken the time to understand their experiences and listen closely to what they share, trust begins to form. They realize this isn’t a cookie-cutter relationship. You’re here to support their growth in a way that fits them.

• Identify hidden strengths and gaps to build on: Sometimes a mentee can name their strengths easily. Other times, they hesitate or focus only on weaknesses. Their answers (and even how they answer) help you spot what they value, what energizes them, and where support is needed most. That’s valuable insight you can build on.

• Discover challenges to work through: Early conversations often reveal the obstacles holding your mentee back—whether it’s a lack of confidence, unclear expectations, or skill gaps. As a mentor, your role is to help them name those challenges and begin turning them into areas of focus for growth.

• Set realistic, personalized goals: Generic goals rarely stick. Work with your mentee to create goals that fit their unique role, pace, and ambitions. When goals are tailored and achievable, they build momentum—and that momentum leads to deeper transformation.

What a Good Initial Interview Form Should Include

You don’t need a long or complicated form. In fact, keeping it simple and clear is more effective. The goal is to open up conversation—not to overwhelm your mentee with a list of endless questions.

Here are the key sections to include:

1. Personal Background

Start with the basics. Ask for your mentee’s current role, work experience, education, and anything else that gives you context. This isn’t just data—it’s the story of who they are.

Sample Questions:

• What is your current job title and what are your main responsibilities?

• What past roles or experiences have shaped your career so far?

• What motivates you most in your work?

Why it matters: Understanding where they’ve come from helps you see patterns, values, and influences that affect how they make decisions and where they might need support.

2. Career Goals

Next, uncover what they want. Whether their goal is a promotion, a career change, or building specific skills, you need to know what direction they’re aiming for.

Sample Questions:

• Where would you like to be in your career in the next 1–3 years?

• What does success look like to you?

Why it matters: Clear goals help guide your mentoring approach. When you know what your mentee is aiming for, you can tailor your sessions to help them make steady progress toward that vision.

3. Strengths and Skills

Now, focus on what’s working. Find out where they feel confident and competent.

Sample Questions:

• What are three strengths you bring to your current role?

• What skills do others often compliment you on?

Why it matters: Knowing their strengths helps you leverage them to build confidence. It also allows you to identify any blind spots—areas where they may feel strong but still need to grow.

4. Current Challenges

This is where things get real. What’s getting in the way of their success? These could be personal, professional, or skill based.

Sample Questions:

• What are three challenges you’re currently facing at work?

• Is there anything that’s keeping you from reaching your goals?

Why it matters: Mentoring is most valuable when it helps someone overcome real challenges. This section gives you the insight to offer timely and targeted support.

5. Areas for Guidance

Get clear on why they sought a mentor in the first place.

Sample Questions:

• What are you hoping to gain from this mentoring relationship?

• Are there specific decisions or transitions you’re preparing for?

Why it matters: This part sets mutual expectations. It helps you understand how your mentee views your role and what kind of help they want from you.

Customize Your Interview Form for Maximum Impact

One of the best parts of mentoring is that it’s flexible. And your initial interview form should be too. You can use a standard version across all mentoring partnerships, or you can adjust it depending on your mentee’s industry, role, or goals.

Here are some quick examples:

• Tech Startup Mentee: Add questions about comfort with change, innovation, or working on cross-functional teams.

• Nonprofit Mentee: Focus more on managing volunteers, fundraising goals, or understanding mission alignment.

• First-Time Manager: Ask about their leadership style, how they give feedback, or what they’re learning about team dynamics.

Make your form a living document. Let it evolve with the relationship. If their answers change over time—or if they gain new clarity—adjust your approach and dig deeper.

How to Use the Form During Your First Session

Think of the form as a guide, not a script. Don’t just go down the list and ask question after question like a survey. Instead, use it to create a meaningful, two-way conversation.

Tips for a Great First Meeting:

• Set the tone: Let your mentee know this is a safe, confidential space.

• Be curious: Use follow-up questions to get them thinking more deeply.

• Look for patterns: As they talk, notice what they care about most.

• Listen for more than words: Watch their body language and tone. What excites them? What worries them?

This is your opportunity to build connection, set expectations, and begin shaping the path ahead.

Reading Between the Lines: What to Watch For

The way your mentee answers matters just as much as what they say.

Let’s say they list very few challenges. Does that mean they don’t have any—or that they’re afraid to admit them? Or maybe they say they want to “become a better leader,” but don’t define what that looks like. That’s your cue to explore further.

Pay attention to:

• Hesitation or vagueness (they may need help clarifying their thoughts)

• Confidence vs. overconfidence

• Self-awareness (how well do they understand their own gaps?)

• Emotional signals (Are they excited? Nervous? Frustrated?)

Your goal is to understand the person behind the answers—so you can offer real help.

How to Turn Interview Responses into a Mentoring Strategy

Once the interview is done, the real work begins. Take everything you’ve learned and use it to start shaping your mentoring plan.

Here’s how to do it:

1. Identify Themes

Group their responses into major categories like career goals, leadership development, or communication skills.

2. Set Short- and Long-Term Goals

Use their input to help them create SMART goals—Specific, Measurable, Achievable, Relevant, and Time-bound.

3. Choose a Focus Area

Pick one or two key goals to start with. This prevents overwhelm and gives your sessions a clear purpose.

4. Track Progress

At the end of each session, revisit their goals. What’s moved forward? What needs more attention?

The Bottom Line: Start Strong to Go Far

The initial interview form is more than a tool—it’s a conversation starter, a trust builder, and a roadmap all in one. When used well, it gives your mentoring relationship the structure and depth it needs to be successful.

By asking the right questions, listening with intention, and customizing your approach, you’ll not only help your mentee grow—but you’ll grow as a mentor, too.

Next Steps: Try It Yourself

Feel free to download the free Initial Interview Template (Interview Guide)  or create your own using the structure above. Use it with your next mentee and see the difference it makes from the very first session.

Coming Up in my next Blog

Next time, we’ll take a closer look at Confidentiality Checklists and NDAs—when to use them, how they build trust, and why they’re more important than you might think.