How to Make the Most of an Alumni Informational Interview

A 15-20-minute conversation with a Midd alum can either confirm what you already know, or possibly change the direction of your career path. The difference usually comes down to preparation.

At the Center for Careers and Internships (CCI), students are encouraged to use Midd2Midd to connect with alumni for informational interviews. The goal is to learn from them, not ask for a job. But turning that conversation into something useful can sometimes require a strategy. Here’s how we recommend you do it.

Step 1: Prepare for 3–5 Strong Questions

In a relatively short conversation, you’ll realistically have time for three to five substantive questions. Start by deciding what you most want to learn:

• Are you exploring a field?
• Testing whether a role fits your strengths?
• Looking for clarity on how to break in?

We advise students to arrive with an agenda and tailor questions to the individual rather than running through a generic list. Preparation signals seriousness, and respect for the alum’s time.

Step 2: Open With Shared Experience

Before diving into job mechanics, build context. We suggest starting with a question grounded in shared experience:

• Why did you come to Middlebury?
• What made you choose your major?
• Knowing what you know now, would you do anything differently?
• What was your sophomore year like?

These questions do more than create rapport. They uncover decision points - moments of uncertainty, pivots, or risks - that shaped the alum’s trajectory. 

Step 3: Map the Path From College to Career

Once you establish connection, move to transition questions:

• When you were a student, did you expect to end up where you are now?
• What got you started in this field?
• After college, what did you feel most prepared for? Least prepared for?
• How certain were you about your path at the time?

The primary goal of an informational interview is to understand the “real story” of a career, not to seek employment. These transition questions often reveal nonlinear paths, unexpected first jobs, and course corrections. If you’re feeling uncertain, that honesty can be instructive.

Step 4: Get Specific About the Work

Next, focus on the profession itself. We recommend asking:

• What do you like best (and least) about your work?
• What projects have excited you recently?
• What parts of your job are most challenging?
• In your organization, what differentiates the most successful recent grads?
• Where is your industry headed in the next 1–3 years?

Instead of “What do you do?” aim for: “What skills actually differentiate strong entry-level hires in your organization?” That answer may reshape how you approach your coursework, internships, or skill-building this semester.

Step 5: Ask for Direction. Not a Job.

Avoid asking directly for openings. Instead, we suggest forward-looking prompts such as:

• If you were me and interested in your field, what would you do next?
• Are there organizations I should have on my radar?
• What are one or two things I could do to keep up momentum until we talk again?
• Who else would you recommend I speak with?

A referral to another professional or a suggestion for a skill to develop can be more valuable than a single job lead.

Step 6: Follow Up and Reflect

After the interview:

1. Send a thank-you email within 24 hours. Reference something specific you learned.
2. If you contact someone they recommended, report back.
3. Evaluate the fit.

Ask yourself:

• Which aspects of this work appeal to me?
• Which would be difficult to tolerate?
• Am I willing to pursue the training this field requires?

Informational interviews are not just about expanding networks. They are about narrowing options strategically.

The Bigger Picture

Midd2Midd offers access to alumni across industries who have volunteered to help. The platform has a broad filter system that allows you to search by location, industry, specific company, affinity group, and more. You can tailor your search based on multiple filters, or keep it broad. Midd2Midd has over 7,000 volunteers who want to hear from students like you. If you haven’t started your networking journey yet, Midd2Midd is the perfect place to start. Sign up takes 5 minutes, so take a few minutes this week and complete sign up here: Midd2Midd.

In a hiring landscape increasingly shaped by automated screening and crowded applicant pools, informed applicants stand out. A well-prepared informational interview can clarify your direction, sharpen your questions, and occasionally lead to opportunities before they’re posted.

The next step isn’t complicated: schedule the conversation. Then prepare.

Need further help? 

• Log into Midd2Midd to access the Midd2Midd Key Questions for Informational Networking resource.