Mastering the Art of Exploratory Interviews

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If the thought of networking gives you a sense of dread because it feels shallow and unfulfilling, I get it. I used to feel the same way until I learned that networking can be fun, interesting, and very rewarding. I’ve got two words for you: exploratory interview.

An exploratory interview, also known as an informational interview, is just a conversation. The purpose is to connect with other professionals in a field or role of interest, to gather insights, advice, and industry knowledge, or just to get moral support from someone who understands what you go through at work. It’s an opportunity to learn about the person’s career journey, experiences, challenges, and successes. You may also ask for recommendations on professional development, networking opportunities, or trends within the industry. Whatever the topic, it’s a win/win conversation – sharing and exploring.

I like using the term exploratory because it is just that, having a conversation and learning about the other person to see if there is something you can gain and share. You never know what it may lead to, and it allows you to expand your network and gain a deeper understanding of a specific industry, a role, or just make a new friend.

If you’re new to networking or in a career transition, these exploratory conversations also give you the opportunity to practice how you speak about yourself and what you’re looking for in a new role. Think of it as a low-stakes opportunity to practice for interviews or speak to people about yourself (which isn’t easy for most of us).

Seeking help from strangers may seem daunting, but here’s a little secret: people genuinely want to lend a hand. Yes, altruism isn’t just reserved for nonprofits. However, to tap into this well of goodwill, you must first overcome two common obstacles: Time and Clarity.

Time is a precious commodity, and people are understandably busy. If there’s no clear boundary around how much time an interaction will take, they might hesitate to say yes. After all, who wants to be stuck in a seemingly endless conversation with no end in sight? Being transparent on the time commitment is crucial.

This transparency extends to the equally important clarity in your ask. When you’re crystal clear about what you need, potential helpers can quickly assess if they can assist. We all want to feel successful in helping others, and uncertainty about how to assist can deter even the most well-intentioned individuals. Be specific in your request, and you’ll be amazed at how receptive people become.

Oh, and let’s get one thing straight: no one wants to be asked for a job, not even the hiring manager. Therefore, make it abundantly clear that you’re not asking the person for a job, is critical. Instead, you’re eager to learn, explore, and gather insights from their experience. With these obstacles cleared, you’ll find that people are more than willing to engage in a fruitful conversation that benefits both parties. Let’s dive into the art of navigating these exploratory interviews like a pro.

Step 1: Crafting the Approach

When reaching out for a meeting, the key to opening doors is to convey your intentions clearly. Craft a message that reflects your genuine interest in seeking advice without appearing overly eager (especially if you’re in a career transition):

Sample Request Email: Entrepreneur

Hi Jesse,

I hope this message finds you well. My name is Rachel Weller, and I am an aspiring entrepreneur looking to establish my own consulting practice in the realm of graphic design for small businesses and startups. My colleague and mutual acquaintance, Sally Feldman, recommended you as someone with valuable insights in this field.

I am particularly intrigued by your expertise in graphic design and believe your experiences could provide invaluable guidance for my venture. I’m eager to learn more about the challenges and successes you’ve encountered along your career journey.

If you’re available, I would be immensely grateful for a brief 20-minute phone call or a virtual meeting via Zoom within the next 2-3 weeks. I assure you that I’ll be mindful of your time and keep the conversation concise and focused.

Thank you so much for considering my request, I look forward to connecting with you soon.

Best regards,

Rachel Weller

Sample Request Email: New Career Path

Hello Amanda,

I am a web developer exploring career paths that combine web development and the food/travel industries. Andrew Hill, a friend of mine since our daughters played soccer together several years ago, suggested that you would have some really interesting insights into this area. Would it be possible to have a brief 20-minute call or zoom so that I could ask you a few questions about your work in Amazon’s food products team? I promise to take no more than 20 minutes of your time.

I look forward to connecting with you soon.

Best regards,

Jon Jackson

Sample Request Email: Cold Outreach

Hi Martin,

I hope this message finds you well. My name is Marcia Jones, and I am a web developer with an interest in exploring a new career path that merges web development with the food and travel industries. As I researched this field your name surfaced as a respected expert, and I was intrigued by your wealth of experience.

[ADD WHAT INTRIGUED YOU] I especially enjoyed your article on the future of food in the NYTimes. I hadn’t thought about the impact of food labs from that perspective before and appreciate your insights on GMO.

I apologize for reaching out without a prior introduction, but your accomplishments with Amazon’s food products team are impressive, and I am eager to learn more about your journey.

I understand your time is valuable, which is why I am humbly requesting a brief 20-minute call or Zoom meeting in the next few weeks (or whenever is convenient for you). I would be grateful for the opportunity to ask you a few questions about your experiences and career journey.

Please be assured that I will be mindful of your time by keeping the conversation brief and this is not a hidden request for a job offer; I really do want to learn about your journey.

Thank you for considering my request, and I look forward to connecting with you soon.

Best regards,

Marcia Jones

Do not attach a resume (makes it seem like you’re just looking for a job).

Remember, while not everyone may agree to a meeting, those who do are likely to provide valuable guidance (and genuinely want to help you). So, keep trying.

Step 2: The Power of Exploratory Questions

Before the meeting you’ll want to do your homework on the person: don’t ask questions you could have easily found out with a web search. That’s a waste of time. Since you promised to keep the time brief, identify the top questions you want to ask.

Here are some examples:

  • How did you achieve your current position and career success?
  • What do you especially like about what you’re doing now (your role)?
  • What are the key challenges or concerns you face in your current role?
  • Could you share your thoughts on working with recruiters in your industry?
  • Let’s talk compensation – to the extent you’re comfortable. Could you describe the various dimensions of compensation in your field, such as starting, mid-career, and established levels?
    • Alternative question: What is the typical starting salary in this field, and how does it progress with experience?
    • Alternative question: In addition to common sources like Glassdoor or, could you provide any additional insights into compensation in this field?
  • As I explore various niches within [X field], do you have any recommendations on conducting thorough research?
  • Considering your experience, what are your predictions for future trends in this [field, company, or role]? Your insights will be invaluable.
  • What specific qualities or achievements must I exhibit to excel in the [position title] role?
  • Is there a lesser-known aspect about [Company X] that outsiders would be surprised to learn?
  • Are there any professional development opportunities or organizations you would recommend for someone in my position?
  • If you were to outline three specific steps for me to establish myself in the [X field], what would you suggest?

For the solopreneur:

  • Apart from your core product or service, what other skills have been essential to sustain your business successfully?
  • What were the key factors that contributed to the success of your business, and how long did it take to establish it?
  • In terms of financial viability, how sustainable is this type of business for someone looking to support themselves quickly?
  • How do you maintain a healthy work-life balance while running your business?

Go here for a long list of sample questions to ask.

Step 3: Wrap Up

During the conversation, adhere to the agreed time frame. Respect for time and punctuality is highly regarded and reflects professionalism.

After the discussion, express your sincere gratitude for their time, and inquire about the best way to stay in touch (email, phone call, etc.).

Always Ask: Can you think of anyone else who would be interesting to talk to about [this field/role]? Would you be comfortable giving me their email address so I can contact them directly? (Get the email address right away if the person is very busy, so you’re not left following up). If the conversation went really well, then ask: Would you be willing to do an introduction to that person?

Send a thank-you note, if you can get a mailing address. A note in the mail leaves a lasting positive impression!

Networking doesn’t have to be a dreaded or superficial endeavor. By embracing exploratory interviews, you can transform your approach when connecting with others. These conversations offer a valuable opportunity to gain insights, advice, and industry knowledge while also providing a chance to practice talking about yourself in a low-stakes setting. By being respectful of others’ time and clear about your intentions, you can tap into the goodwill of people who genuinely want to help. Crafting a thoughtful approach and preparing meaningful questions ensure that these conversations are fruitful and mutually beneficial. So, don’t be afraid to reach out, connect, and dive into the art of navigating exploratory interviews like a pro. You’ll be surprised by the doors that can open and the meaningful connections you can make. If you need help putting yourself out there, I’m here for you.