Questioning and Listening Skills in Career Advising: From “Fixer” to “Guide”

Questioning and Listening Skills in Career Advising: From "Fixer" to "Guide"

As a career advisor or school counselor, your day is a barrage of panic.

  • “I don’t know what to major in.”
  • “My parents want me to be a doctor, but I hate blood.”
  • “Am I going to be unemployed forever?”

Your instinct is to Fix It. You want to pull out a brochure, point to a job, and say, “Do this. It pays well. Problem solved.”

This is called the “Righting Reflex”—the urge to set things right. But in career advising, “fixing” the problem is often a mistake. If you tell a student what to do, they might do it—but they won’t own it. And when it gets hard, they will quit (or blame you).

The goal of advising isn’t to be the Expert with the Map. It is to be the Guide with the Flashlight. You don’t determine the destination; you just help them see the path.

Here are 5 advanced questioning and listening techniques to transform your advising sessions.

1. The “Open-Ended” Audit

Most conversations die because of “Closed Questions”—questions that can be answered with a “Yes” or “No.”

  • Advisor: “Do you like Math?”
  • Student: “No.”
  • Advisor: “Okay… do you like English?”
  • Student: “I guess.”

This is an interrogation, not a conversation. To unlock a student’s true interests (the Saturday Morning Test), you must switch to Open-Ended Questions.

The Cheat Sheet:

  • Don’t Ask: “Do you want to be an Engineer?”
  • Ask: “What is it about Engineering that caught your attention?”
  • Don’t Ask: “Are you worried about money?”
  • Ask: “What role does salary play in your decision-making process?”
  • Don’t Ask: “Did you like your internship?”
  • Ask: “Tell me about a day at your internship where time flew by. What were you doing?”

2. The Power of “Reflective Listening” (Mirroring)

Students often don’t know what they think until they hear themselves say it. Your job is to be a mirror. When a student dumps a chaotic mix of emotions on you, don’t offer a solution. Just reflect it back.

The Technique:

  • Student: “I don’t know, I just feel like everyone is getting ahead of me and I’m stuck, and my dad keeps asking about law school but I want to do something creative but creative jobs don’t pay.”
  • Advisor (The Mirror): “It sounds like you feel paralyzed by the pressure to choose between financial safety and your actual interests.”

Why it works: The student hears their own chaos organized into a clear sentence. Usually, they will sigh with relief and say, “Exactly.” Now that the problem is defined, they can start solving it.

3. The “Scaling Question” (For the Indecisive)

When a student is stuck between two choices (e.g., Double Majors vs. Starting a Business), they often spiral. Use the 1-to-10 Scale to force a decision.

The Script:

  • Advisor: “On a scale of 1 to 10, how confident do you feel about majoring in Psychology?”
  • Student: “Maybe a 6.”
  • Advisor: “Okay. Why is it a 6 and not a 4?

The Psychology: By asking “Why isn’t it lower?”, you force them to defend the positive reasons.

  • Student: “Well, it’s not a 4 because I really love understanding how people think.” Suddenly, they are selling themselves on the idea.

4. The “Miracle Question” (For the Hopeless)

Some students are so bogged down by GPA stress or family expectations that they can’t dream. Remove the barriers with a hypothetical.

The Script:

“Suppose you go to sleep tonight and a miracle happens. You wake up five years from now, and your career life is perfect. You are happy. You are paid well. What are you doing when you wake up on that Tuesday morning?”

Watch their face. Do they say they are in a high-rise office in a suit? Or are they in a forest tagging wildlife? This bypasses the “logical” brain and accesses the “aspirational” brain.

5. Embrace the “7-Second Silence”

This is the hardest skill to learn. When you ask a deep question, the student will fall silent. Your instinct will be to fill the silence because it feels awkward. Don’t.

That silence is where the thinking happens. If you interrupt the silence, you interrupt the insight. Count to 7 in your head. 1… 2… 3… Usually, around second 5, the student will blurt out the real truth: “I think I’m just scared of failing.” That is the breakthrough. You only get it if you wait for it.

You Are Not the Savior

The best career advisors are lazy, in a strategic way. They don’t do the work for the student. They ask the questions that make the student do the work.

By using Open-Ended Questions, Reflections, and Silence, you stop being a “Fixer” and start being a “Catalyst.” You aren’t giving them a fish. You are teaching them that they already know how to catch one.

Want to give your students better tools to answer these questions? Use the Anutio Career Platform to let students self-assess their skills and interests before they walk into your office.

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