19 powerful questions to ask in an exploratory interview to inspire and inform your next career move.
19 powerful questions to ask in an exploratory interview to inspire and inform your next career move.
Hi!
No amount of navel-gazing or online job searching comes close to the insights you can unlock in a single exploratory interview.
An exploratory interview is a networking approach that leads with deep curiosity and is guaranteed to lessen the stress of having a first-time conversation with a new professional connection.
An exploratory interview follows this structure:
Ease their mind.
Deep dive into their professional journey.
Deep dive into their craft, role, or industry.
Uncover unmet needs and opportunities.
Ask for introductions.
Return 2x the help you received.
I've included for you a detailed explanation of this approach here.
Today, I want to discuss how to ask great questions in an exploratory interview. By great, I mean the kinds of questions that:
Extract valuable nuggets of wisdom from their career trajectory.
Define what “great” looks like in their work.
Uncover pain points and opportunities in your wheelhouse.
Build rapport and trust and open the doors to new opportunities.
Let’s dig in!
Before we begin, I have two favors to ask.
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Specificity is the key to asking powerful questions.
Most people feel awkward about picking someone’s brain, so they use vague questions such as “Tell me about yourself,” “What do you do for a living?”, “How do you like your work?” or “What’s your take on [topic]?”.
The first step is to always do some research on the person (without getting weird, of course). Study their LinkedIn profile to map out their career trajectory. Look for common ground (maybe hobbies, common acquaintances, schools, certifications). Google them and see if they’ve been featured, awarded, or recognized in the industry. Read any content they’ve written.
Next, prepare your questions in advance. It’s perfectly fine to pull out a paper with a list of questions at the start of the meeting. If anything, preparation shows respect and gratitude to the other person.
Powerful questions are specific. They elicit concrete stories and situations. They make the person think and invite them to connect the dots. You know a question is powerful when you hear reactions such as:
“That’s a great question… I don’t think I’ve been asked that before.”
“Hmm, now that I think about it, I realize that….”
“I don’t share this very often, but….”
“I’m glad you asked that!”
Powerful questions you can ask at every stage
Ok, so you broke the ice: You spent 5 minutes talking about the weather, re-introduced yourself, and why you’re interested in having this conversation. And, very important, you put their mind at ease by mentioning that you’re not here to ask for a job, hand out a resume or make a sales pitch.
Next, I’m about to share five powerful questions for each category. You’ll unlikely get to all of them, so pick and choose the most appropriate ones for the occasion.
So the interview begins…
1️⃣ THEIR JOURNEY: NUGGETS TO INSPIRE AND INFORM YOUR SEARCH.
Believe it or not, most people are seldom asked to talk about the moments that shaped them and how they became who they are today. The fact that you are starting the conversation here sends a powerful positive signal: You are interested in them, NOT in what they can do for you. This equalizes the power scale.
It makes them feel special and appreciated.
It signals a genuine intent on your part.
It shifts the burden of “impressing” onto them, allowing you to relax, listen and think with clarity.
It makes you trustworthy and likable.
💡 Five questions to learn about their background and professional trajectory.
How has your career evolved, and what have been some highlights and lowlights?
What inspired you to pursue this line of work, and how did you discover your passion for it?
What pivotal moments in your life and career shaped you as a professional?
What have been some of the most valuable lessons you learned about yourself throughout your career?
What are some of the proudest moments in your career? How so?
2️⃣ THEIR CRAFT: WHAT THEY DO AND WHAT “GREAT” LOOKS LIKE.
Knowing what to expect is essential when considering a career pivot into a different industry or role. Now, you’re steering the conversation to picture how it would feel working in their field, position, or industry and what it takes to thrive there. This is where you get to search for clues about:
How could a pivot look like (viability)?
Which skills and strengths you could transfer (desirability).
Which skill gaps you’d need to close and how (feasibility)?
How to shorten the learning curve.
💡 Five questions to learn more about their craft, industry, and role.
Can you walk me through a typical week in your role? Could you give me examples of projects you work on?
What are some of the most and least rewarding aspects of your job? What keeps you motivated?
What are some common misconceptions about your industry or role that you would like to dispel?
What are the technical skills and personal aptitudes required to be successful in your role and industry?
What advice would you give to a seasoned professional looking to break into your industry (or a similar role)? e.g., what are landmines to watch out for, and what can they do to transition successfully?
3️⃣ THE INSIDE SCOOP: UNMET NEEDS AND HIDDEN OPPORTUNITIES.
This is where you’ll begin exploring how to position your strengths and skills. Notice that you’re not discussing your qualifications for a job (unless they bring it up). You’re still exploring and learning about their aspirations, barriers to success, and the greatest pain points. These insights will help you:
Assess fit with their industry, role, or organization.
Understand the realities of their day to day.
Formulate recommendations to bring back at a later date (this is where you can demonstrate your chops)
Ideate ways to position yourself as a resource (connections, readings, tools, etc.).
💡 Five questions to uncover unmet needs and relevant pain points.
What’s a big win you’re hoping for, and what would it mean to the business and your role?
What about it keeps you up at night? Why?
If you had a magic wand, what would you change or eliminate? Why?
What are some of the biggest daily challenges, and how do you address them?
What resources or support do you wish you had available to help meet your goals?
4️⃣ THE CLOSING: PAY IT BACK 2x
Don’t ask for favors. Ask for introductions and return more than what you receive. Most job seekers bomb it by nudging the other person to advocate and help them land an interview. This only works if the other party offers it. Otherwise, it’s a burden. A better route is to trade connections and resources on the “first date.” It takes little effort to make an introduction or share a valuable information source, yet the benefits are massive.
💡 Demonstrate gratitude and close with these questions:
Would it be helpful if I introduce YOU to [connection]?
I read [article, book, etc.] about [interesting topic]. Can I send it to you?
Who in your network would you recommend I talk to so that I can learn more about [insert specific area of interest]?
Can you recommend any resources or further reading for someone looking to learn more about your industry or craft?