Conducting My First Interview

As part of a new project and long time goal, Lewis Croft, I began interviewing small business owners (or anyone interesting really). I’ve had a lot of interesting conversations with business owners and wished I had a record of some of them.

This is a recap of my first formal interview. Partly for my own benefit and partly so people can learn from my mistakes. It’s a new experience and something out of my comfort zone.

I am sitting in a Dunkin Donuts one hour before conducting my first interview. Translating my scrap paper notes into an outline that I will use during the interview.

I’ve been up for the past three hours working on questions and thinking through the interview. Starting something new and exciting gives me a nervous energy that woke me up early. Not helping, is the constant caffeine intake as well.

I was excited to conduct the interview and managed to fill three pages of my notebook with questions and topics I wanted to discuss. Some questions I came up with, but many were from podcast interviews I had listened to before. (Tim Ferriss what a big influence on many of the questions.)

a couple pages from the notebook
I didn’t end up using any of my notes during the actual interview. Instead turning it more into a conversation about my own curiosity than a question and answer session. But the pages I wrote before the interview got me thinking about the right things. It made me realize themes I wanted to focus around and the questions followed. 

All the preparation and thinking I did beforehand made it possible to have a conversation.

Don’t sit down for an interview with a list of questions you plan to read off. Have a prepared question or two to start and have a couple prepared questions to end. The rest should flow like a conversation. Ask questions that build off the last thing said.

You will get better answers out of the interview this way and it will allow the interviewee to build off their answers. It will flow better and feel more like a conversation rather than a job interview.

Some notes and takeaways from the first interview. I jotted these down in my notebook shortly after the interview.

  • Check your equipment the night and hour before the interview. I purchased a voice recorder to use a few weeks before the actual interview. It worked fine when I got it. The morning of the interview I couldn’t get it working and didn’t have time to troubleshoot. I recorded the entire interview on my iPhone (turn off all notifications before recording).
  • Have a time frame for your interview. It doesn’t have to be a hard time limit but don’t take advantage of another person’s time. I planned for the interview to be about an hour. I set a timer on my watch for 45 minutes. When the alarm went off I knew I needed to start wrapping things up. 15 minutes gave time for the conversation to end naturally and not abruptly.
  • Before the interview, explain why you are doing the interview. What’s the audience, and how is it going to be used. This will help shape some of the answers.
  • Have warm up questions. Don’t go right into open ended questions or the generic “tell me about yourself.”
  • It’s an interview not an interrogation. Keep it conversational. It’s ok to talk about yourself. There should be a give and take. You’ll get better answers that way.
  • Write down all the questions your want to ask. Pick a couple themes based on the questions. Write them down to reference during the interview. Do not just bring a list of questions to the interview and try to get through them all.
  • Have some closing questions. It signals the end of the interviews, but makes sure it doesn’t end suddenly. The ones I used. Are there any questions you wished I asked? Is there anything you wanted to elaborate on? Who should I interview next?

I hope these tips help other people. I am in no way a professional at this. I’m not even a writer. But it is something that I found very interesting and exciting.

Interviewing is a great way to get into conversations you wouldn’t normally have, and gets you into a room you wouldn’t normally be invited to.


Since conducting my first interview, I have had several more. Some have been in person, some have been over the phone.

It has definitely become easier over time. I’m more comfortable talking with people and I am able to ask better questions. Looking back at the first interview I conduction it’s amazing how much changed in a short time.

A few additional notes. Keep pen and paper with you during the interview and take notes on things you want to come back to. When the person you are interviewing is telling a story and hits an interesting point, jot it down, let them finish the story, and come back to the point later. Don’t interrupt the story or you’ll lose a lot of the momentum of the conversation.

Interviewing has allowed me to talk with people and ask questions I wouldn’t normally get to ask. It’s been a big learning experience and I recommend it to anyone that owns a business or wants to start a company.

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