The Anatomy of an Exploratory Interview

Hi!

Last week I wrote about the power of rekindling old connections.

Approaching your “dormant network” is an effective and low-risk way to regain energy, confidence, and enthusiasm to shortcut the Mid-Career Funk. It’s also a sure way to get introductions and referrals.

But for many folks, venturing outside the network can be daunting.

Today’s edition is dedicated to those who feel that way. I want to talk about how you can lessen that stress and get the most out of a first-time conversation with a new contact.

Let’s talk about Exploratory Meetings.

Let’s dive in!

Whoa… Slow down! Not on the first date.

The mistake that most people make is treating every connection as an active lead.

Their inner chatter goes like this: “Who knows… they may be hiring. This person has an important title. I have to show my chops. This is a unique opportunity to cut in front of the line!”

Performance anxiety kicks in and screws everything up.

There’s an implicit pressure to stand out, say the right things, showcase achievements, and come across as a go-getter. The focus is on the job seeker and their career goals. The tone of the session goes more or less like this:

“Hi, I’m delighted to meet you, blah, blah…I wanted to talk to you because I’m looking for blah, blah… let me tell you all the things I’ve done… blah, blah… I have a ton of experience with blah, blah, blah… Are you hiring, or do you know of someone who is… and would it be ok if I give you my resume and maybe you can put a good word for me?”.

Meanwhile, the person on the other side listens politely and agrees to forward the resume “to someone.” But 90% of the time, they’ll forget or send it to “someone” who is not hiring at the moment.

Lead with genuine curiosity.

A better approach is to set up an Exploratory Meeting — like a curious anthropologist conducting a deep dive into the other person’s world.

The difference is that 80% of the conversation is about THEM, and 20% is about YOU.

An Exploratory Meeting has three goals:

1) Gain insights and inspiration to inform your search.

2) Relate at a personal level.

3) And as a result, get introduced to like-minded people.

(Notice that "getting a foot in the door" is not listed.)

The beauty of this approach is that you get to ask questions, and the other person does most of the talking. Your job is to listen carefully and take notes.

This flip of roles changes the whole dynamic. You are in control. The spotlight is no longer on you, so you can relax and enjoy the conversation.

See the difference? You just shifted from “will they see value in my skills?” to “how might my skills add value to them?”

How to structure an Exploratory Meeting.

Remember this rule: “Garbage in, garbage out.”

Preparation is still needed, but it looks different.

Think of it as if you’re hosting a podcast. You do a little research on your guest and prepare several thoughtful, open-ended questions for the allotted time. It’s totally fine to pull out a piece of paper and say, “I made a list of questions I wanted to ask you.” If anything, it shows how much you value this conversation.

Here’s the general structure:

1) THE OPENING: EASE THEIR MIND FROM THE START

Reinforce that you are not here to ask for a job but to ask questions, and at the end, you'll ask for a couple of new connections who could help inform your journey.

2) THEIR JOURNEY: DIG FOR NUGGETS TO INSPIRE AND INFORM YOUR SEARCH

Believe it or not, most people don’t get asked to talk about the moments that shaped them and how they became who they are today. There's a lot to learn from their journey. You can ask what drove them to pursue this field, how their career evolved, and what they learned about themselves.

3) THEIR CRAFT: LEARN ABOUT WHAT THEY DO AND WHAT IT TAKES TO BE “GREAT.”

This section is essential when considering a career pivot into a different industry or role. Explore what a day/week at work looks like, what kinds of projects they work on, and the best and worst parts of the job.

4) THE INSIDE SCOOP: DIG FOR UNMET NEEDS AND HIDDEN OPPORTUNITIES

This is a chance to assess whether or not you’d thrive in their work environment. You can ask about their aspirations, the barriers that stand in the way, and the common pain points in their role. Perhaps your strengths and skills are just what they need.

5) THE CLOSING: ASK FOR INTRODUCTIONS, NOT FAVORS

Always show gratitude and close with these two questions:

• Is there anything I can do to help YOU?

• Who in your network would you recommend I talk to so that I can learn more about [insert specific area of interest]?
  

6) THE FOLLOW-UP: RETURN 2X THE HELP YOU RECEIVED.

If you want to make a lasting impression, this is where you do it. Send a thoughtful thank you note, share a couple of your favorite resources and introduce them to people you admire in your network. If they offered you one new introduction, offer them two of yours. Do it within the next 24 hours. It shows that they are a priority.