Informational-Interview Prep

An informational interview is one of the best career tools — a short, low-pressure conversation to learn about a field, role, or company from someone doing it. But done wrong (vague questions, or angling for a job) it wastes their time and yours. This preps the whole thing: the ask, the right questions for your goal, how to run it, and a follow-up that turns a chat into a relationship.

What This Skill Produces

• The outreach ask — a short, specific, low-friction request for a brief chat (not a job)
• A focused question set — tuned to your goal (exploring a field, breaking in, learning about a company/role), from their path to practical advice
• Conversation flow — how to open, keep it their-story-centered, and use the time well
• What not to do — the mistakes (asking for a job, dominating, being unprepared) that sour these
• A follow-up — a thank-you and a way to keep the connection warm, including any offered next step
• Prep notes — what to research about them beforehand

Required Inputs

Ask for these if not provided:

• Your goal — exploring a field, trying to break in, targeting a company/role, or broad learning
• The person — who they are, their role, and your connection (if any)
• Your background — enough to tailor relevant questions
• The format — call, coffee, video, and how long
• Where you are — early exploration vs. active job search (changes tone)

Framework: Learn, Don't Pitch

1. Ask small and specific. Request a brief (15–20 min) chat to learn, name why them, and make it easy to grant — never open with a job ask.
2. Prepare targeted questions. Match questions to your goal: their path and day-to-day, how they got in, what they wish they'd known, and specific advice for your situation — not things you could Google.
3. Center their story. Let them talk, listen actively, and go deeper on what's useful; you're there to learn, not to perform.
4. Don't ask for a job. The fastest way to sour an informational is to turn it into a pitch — build the relationship; opportunities follow later.
5. Follow up well. Thank them specifically, act on any advice/intro they offered, and keep the door open for a light future touch.
6. Do your homework. Research them enough to ask informed questions and not waste the time.

Output Format

Informational interview: goal x] · person/role] · format/length]

Outreach ask > Specific, brief request to learn + why them + easy to say yes — no job ask].

Questions (tuned to your goal): their path · day-to-day · how they broke in · what they wish they'd known · specific advice for you]. Run it: open warmly · their story first · go deeper on useful bits · watch the time]. Don't: ask for a job · dominate · show up unprepared. Follow up: specific thank-you · act on advice/intros · keep it warm]. Prep: what to research about them].

Quality Checks

• ] Outreach asks for a short chat to learn, not a job
• ] Questions are tuned to the goal and not Google-able
• ] Guidance centers the other person's story
• ] Explicitly warns against turning it into a job pitch
• ] Includes a specific, relationship-building follow-up
• ] Notes what to research beforehand

Anti-Patterns

• Opening with a job ask or angling for one.
• Generic questions answerable by a quick search.
• Dominating or making it about you.
• Showing up unprepared about the person.
• No follow-up — wasting the connection.

Example Trigger Phrases

• "Help me prep for an informational interview with someone in product management."
• "What should I ask someone whose career I want to learn about?"
• "How do I reach out for a coffee chat without it being weird?"
• "I have a call with someone at a company I'm interested in — what do I ask?"
• "Questions for an informational interview to help me break into a field."