VII. The Interview

Finally, the interview!

The interview itself is the best yet hardest part of the process. Anyone can get a person’s contact info and send them an email. Much harder is actually meeting someone you have never met before, grabbing coffee with them and carrying on an hour-long conversation. It will take practice, a bit of confidence and a good attitude. I promise it will be worth it. Remember, all you are trying to do is learn. That’s it. You are not trying to impress them or sell anything to them. You are not necessarily trying to “get” anything from the other person. All you want is to learn, and anything else that comes your way is even better. Hopefully that should take some of the pressure off.

This chapter is broken into the three parts of every interview: Beginning, Middle and End. Hopefully each section provides you guidance and lots of resources to help you plan for your interviews.


All preparation aside, you are now at the meeting. You’ve found the coffee shop, pulled in, and you are sitting in your car. It’s time to get in there. If you have arrived early (you should have!), don’t order food or buy coffee yet. Hang out and wait for the other person.

Now that the other person has shown up, exchange pleasantries. Say “Hello, how was traffic?” (if you are in Los Angeles like I am!) and have a one or two-liner ready. Ask if they would like to grab coffee or grab a seat. The initial small talk is key before you are sitting down across from the person. It helps break the ice and get a conversation flowing. Opportunities for small talk include: your common connection, an article you saw about them or the industry, or the simple “How’s it going today?”

After you’ve exchanged the pleasantries, the initial phase of the conversation can go two ways: They may start asking you questions right off the bat, or you will need to fill some “empty space” and have your five minute speech ready to rattle off (See Rule 7: Come to the meeting ready to lead it). Most often, they will ask about your background and what you are doing now in your job or studying in school. This is good and shows they are interested in you. Your job during this beginning phase is to get the person comfortable enough with you that you can start firing questions at them and start learning. If you have an hour meeting, the goal by the end of the beginning phase is to have the interviewee talking 75% of the time. No matter how long the meeting, the beginning phase is no longer than ten minutes. Keep it short so you can start asking questions and getting to the more important middle and end phases.

Listen closely while they give you their five minute background. Look for items to add to your mental list to ask them about later in the middle phase. They’ll name drop, mention companies, discuss hobbies, family, friends, career choices, education, and a myriad other things. Usually if you’re listening well, you’ll have enough question material for at least an hour. Feel free to write these items down in your notes for later questions. If you are bad at listening or not interested in their story, pretend you are. Imagine you are interviewing the other person for a story about their life for CNN. Besides details and interesting anecdotes, try to find what two to three pieces of advice they have to offer. This helps frame your thinking during the beginning.

Remember, the first part of the interview is to: disarm the other person, get them comfortable with having a conversation, and to get some items to ask them about as the conversation rolls on.

Some starters for conversation include:

  • Your back story
  • Your last interview with common connection
  • Your commonality (same school, city, industry)
  • Article about the industry, company, person

Some questions for conversation include:

  • What is your back story?
  • What does a day in your life look like?
  • Where did you go to school?
  • How did you choose [Industry]?
  • What do you do?
  • Tell me some more about [company], [person], [school], [job]


At this point, usually the pleasantries and backstory are out of the way. The conversation, if done correctly, is now moving towards you asking questions and them answering, teaching, and advising. You should now have some good items to ask about from the first couple minutes of talking. This next phase is the time to gather information, hopefully unique to this person that is helpful to you.

This is a good time to let conversation tangents go wild. You may ask a question that gets the other person excited. Let that conversation go for a while before revisiting some of your other topics. Keep taking mental notes to continue the line of conversation if need be. Hopefully you’ll be able to gain some insight or perspective you haven’t heard before. Feel free to ask them to explain what they mean if you don’t understand. Topics of conversation often range from: details of their career advancement, personal experiences, nitty-gritty of an industry, projects they have worked on, what is going on in the marketplace, do’s and dont’s, personal career advice and really everything.

If you don’t find a topic that excites them immediately, cycle through your items until you find something that does. Some people like telling stories, while others like talking about the future. Some people like talking politics, others the economy. Some like to advise while others like to learn. Keep going until you find it; everyone has an “it”. Usually you can tell by how quickly they answer your question. If they immediately jump in, you are onto something. A big pause, followed by an “I don’t know, I’ll have to think about that one” is usually a sign you need to take an alternate direction.

This section of the conversation is the time to gather information and seek advice, setting you up for the big finish.

Some starters for conversation include:

  • I heard such and such, what do you think?
  • I am at this place in my career and am thinking this, what do you think?
  • What is going on in the economy that affects you?
  • Nitty gritty of your industry
  • Personal experiences
  • What is going on in the market
  • Career advice

Some questions for conversation include:

  • What would you work on if you were me?
  • What would you be reading?
  • What education should I pursue
  • How would I get into this industry?
  • What should I be doing that I am not?


The End phase is the most important part of the informational interview. It is also the part left-out most often. I unintentionally left it out of many interviews during graduate school. While practically easy, it is usually very difficult to force yourself to do. As previously mentioned, it revolves around these two questions:

“Is there anyone you think I should talk to?” and

“Is there an opportunity for me right now at this company?”

These two questions afforded me many investment opportunities, jobs, mentorship, new networks, colleagues and friends. Without these two questions, often informational interviews are easily forgotten – a one time talk with someone. But using them, you’ve now turned your meeting into a “call to action,” directly asking someone to help you. The best part: nine of ten times they do.

You have now spent 45 minutes with someone, and the end is near. The coffee is almost gone, your butt hurts, and you are late for work. They probably feel the same way. It is time to wrap it up, and there are a few ways to do so. You can thank the other person for their time, and regurgitate one or two things you learned that day. You can preface the last questions with “one last thing….” You can let them know you need to get to work. Frame the conversation so they know it is wrapping up. Remember though: Do not leave without asking the questions.

My favorite way of bringing them up is usually something like the following:

“Wow this has been great. I’ve really enjoyed learning about your career and what you do. I really liked hearing about your perspective on [whatever]. Thanks again for your time. Before we go though, there’s two questions I always like to ask at the end of our interviews. One is “Is there anyone you think I should talk to?” and Two is “Is there an opportunity for me right now at this company? *Smile *Subtle laugh *Wait”

The first part lets the other person know you are wrapping up. You praise and thank them for their sage advice and time. Then you frame the questions as a personal rule: this is just something you do all the time, you aren’t asking for anything extraordinary or exceptional. Finally, you smile and/or laugh, letting them know while an earnest question, it’s ok if they say no, because it’s not too serious. Then wait, giving them a chance to think and respond. It usually works.

If they say yes to either, ask for steps to follow up. If they think of two or three names to meet with, write them down and tell the person you’ll shoot them an email later asking for their info. If they say there might be an opportunity for work, ask them who you should talk to next, and when? No matter what you do, be sure to ask when you can follow up again.

Please try it! Asking these vital questions are hard to do, but so often the results are way better than you would have expected.

After that, it’s over. Shake hands, part ways, and follow up soon.

Previous: Chapter 6: Setting Up the Interview and Preparation

Next: Chapter 8: Follow Up