Exploratory Conversations
Exploratory conversations, otherwise known as informational interviewing, are a useful tactic to explore and uncover answers to questions about a particular career path, company, or industry. Once you have sought out the right contact to set up an exploratory conversation, there are a few steps to prepare for your meeting.
The Purpose of Exploratory Conversations
Learn About Industry Trends
Research the company and industry before the meeting.
Ask questions that can only be answered by a professional in the field.
Example: Desired skills, technology, projects, issues
Learn About the Person’s Career Path & About a Typical Day
Find out if their career is what you expected or if you are interested in it.
Learn if your target companies are places you can excel and succeed in.
Ask for their story (Goals, successes, failures, advice).
Gain Insider Information About Landing a Job
Ask about special qualities or skills the organization looks for in new hires.
Maybe gain an influential contact who makes important hiring decisions.
Maybe find out that the company plans to open a new internship opportunity.
Learn About Other Contacts & Resources
At the end of the meeting, always ask if the person knows someone who might have more resources or suggestions for you.
If they provide a name, ask if it is okay to use their name when reaching out.
Secure a New Supporter
The more prepared you are for your meeting, the more likely you are to convince your contact to invest time in helping you.
Do not ask for a job but know that it is sometimes a possibility. They may not hire you but could introduce you to others and advocate for you.
Questions to Ask Yourself Before
- Discuss how your skills may translate to a new but related industry.
- Brainstorm about your career options.
- Discover the company’s culture (and where potentially you may fit).
- Obtain information about the growth or hiring trends of other companies in your industry.
- Brainstorm names of other industry related companies.
- Identify key players you want to meet (such as decision-makers in your target companies).

Questions You Could Ask
First, learn about the person, their role, and the industry – build the relationship!
- How did you get started in your current field?
- What aspects of your job do you find most rewarding/challenging?
- What skills are most important for success in your position?
- If you were starting over today, what would you do differently?
- What do you see as the future trends in this industry?
- What skills are employers looking for in this industry?
- Do you have any ideas about industry associations, or strategies I may not have considered?
- Do you know the names of any industry specific websites I could investigate?
Then, ask them for advice or help.
- Who do you know who works in (appropriate field/industry/company)?
- Would you look at my target list and tell me if you have any contacts in these companies?
- Can you name other companies that might be interested in someone with my background?
- Do you know the names of any good recruiters in my field?
- Can you suggest what other positions might match my skills and background?
- Can you provide me with the names of other people who might be willing to speak with me?
Tips for Requesting an Exploratory Conversation
Ask Someone You Know for an Introduction
Referrals will improve your chances of a response and meeting with the person.
Request Information and Insight, Not a Job
Make it clear you want to learn from the person. Ask them for advice.
Explain the Purpose of the Meeting Depending on the Person
Role of interest: Learn what the job really entails and what skills or training is most helpful.
Target company: Learn what it is like to work there (company culture, types of projects, types of clients, etc.).
Prepare for Likely Objections
Develop a script or list of points so you are prepared to introduce yourself and explain what you are asking of them. Some people may decline or give an excuse. Try to include how this person might benefit from meeting with you.
Be Truthful
Be sincere when you request a meeting; you should not have any hidden agendas and do not ask for a job. Be clear about the topics you want to cover and what you will be asking.
Face-to-Face
Request an in-person meeting at a convenient place for the person. Face-to-face meetings are more likely to forge a connection and build a relationship. If an in-person meeting is not possible, set up a video call.
Tell Them Who You Are
Include 1-2 short sentences summarizing your background. Be concise and only include relevant information. You can also include a link to your LinkedIn profile after your signature.
What to Include in an Effective Request
Use an interesting subject line that is clear and compelling. Then, tell them why you want to meet. If applicable, explain how you know the person – include a mutual connection. To make the conversation more likely to be scheduled, suggest meeting dates.
Steps to Prepare for an Exploratory Conversation
Do a Google search on the person. Is there anything you can mention about any positive press? This also shows that you are on top of industry news.
Review their online presence, focusing on professional and educational information. Look for any common points or connections you may have.
Use something from your research or a lighter topic (weather, location, etc.). This helps set the tone and allow them to get to know you more. Try to naturally work any common points into the conversation.
What do you want to accomplish during this conversation? Remember, the purpose is to build a relationship, not get a job.
What information does this person have and how can it help you?
It will likely be a 20–30-minute meeting, so an agenda will keep you on track.
5-10 minutes: greetings, small talk, pitch/purpose of the meeting.
15-20 minutes: ask questions about them/their career.
3-5 minutes: thank you, ask for other contacts, offer your help.
Plan plenty of questions and allow them to fully answer them. Make sure to show you are listening – nod, smile, and ask follow up questions.
This is not the purpose of the conversation!
Practicing will help you feel more comfortable when you are in the conversation. However, what you say should not be completely scripted or unnatural. Make a list of things you might want to say. Discuss current and relevant topics, avoiding politics and religion. Role-play with family, friends, or in front of a mirror.
Send a thank you message while the meeting is fresh – within 24-48 hours.
Thank them for their time and information. Explain why the meeting was helpful and how you plan to use their advice. This proves you listened and helps build a better relationship.