15 Insightful Questions to Ask Your Loved Ones to Capture Their Wisdom & Stories.

15 Insightful Questions to Ask Your Loved Ones to Capture Their Wisdom & Stories.


Is there someone important in your life that you wish knew more about?

Has someone passed away already that you wish you had captured their stories, their wisdom and their perspectives for yourself and future generations?

Yes, me too. That’s why I created this system that I call “The Loved Ones Insightful Interview”

My Story

I had this idea to interview my parents for years, but just never took action on it. My mother suddenly passed away in early 2020, and I lost the opportunity to interview her, forever. 

Within a few months, I organised an interview with my 73 year old father, asking him a wide range of insightful questions, which allowed me to learn more about my father, his history, his perceptions and his motivations, than I had learnt about him in 40+ years.

The interview took 2.5 hours, and it also took a few hours to cut up the video footage, but now I have a 3-part series uploaded on Youtube (but hidden from the public), distilling down my fathers wisdom & stories for future family generations & prosperity.


The 15 (or 33) Insightful Questions

I won’t include all 33 of the insightful questions, as you can go grab a copy of the full system for free here.

I know that to some people the thought of asking 33 questions, might seem overwhelming, so I have summarised these down to the most impactful 15 x Insightful Questions for you:

  • What was it like for you growing up and what stands out to you from your childhood?
  • What do you remember most about your Mum & Dad?
  • If your Mum & Dad had a message to you and their grandchildren, what do you think it would have been?
  • What is the story of how you met your partner?
  • What message do you have for [spouse] that you want her/him to always keep in mind?

Do these two questions for each child

  • When you think about [loved one’s child] how would you describe him/her?
  • What message do you have for [loved one’s child] that you want him/her to always keep in mind?
  • How did you choose your career and what was your favorite part about it?
  • What do you think made you successful at work?
  • What times in your life truly tested you and what did you learn about yourself by handling that situation? 
  • What three events most shaped your life?
  • What were the three best decisions you’ve ever made?
  • What are you most proud of in life?
  • What message would you like to share with your family?
  • What are you most thankful for?



  • Set up a Smart phone on a tripod (this tripod is a good option)
  • Ensure that lighting is adequate
  • Consider investing in a lapel mic (Rode SmartLav+ is a good option)
  • Ensure your family member feels good about the interview and is willing to explore the questions, without feeling ‘pressure’.
  • Ask family member to make eye-contact with you (interviewer) instead of looking directly into the camera, to make the video look more natural and ensure the interviewee feels more at ease.
  • Feel free to ask “Tell me more about that” to encourage your family member to explore a specific topic even more.
  • Feel free to include any other insightful questions you like.
  • When finished, edit out the unwanted footage, and upload to Youtube as unlisted so you never have to worry about losing the video file.



  • Avoid ‘leading’ or directing your line of questioning too much to ensure you capture an authentic representation of your family members’ insights.
  • Avoid discussing any tension such as family conflicts or emotionally charged opinions, to ensure the overall feel of the interview is positively focused.
  • Avoid giving any judgement or opinion to any responses from your family member to ensure they remain ‘open’, ‘honest’ and feel safe.
  • Avoid putting pressure on your interviewee to answer all the questions. If they don’t feel comfortable about answering a question, skip it and ensure they remain in a positive ‘effortless’ state.
  • No one likes to feel like they have to ‘think hard’, so as an Interviewer, you need to avoid putting too much ‘cognitive strain’ on your interviewee. Keep it light-hearted and as effortless as possible for them.
  • Avoid any pressure to force a family member on camera. If they don’t like to be on camera, you can record their audio and include a slideshow as the visual element later in the production stage.
  • Avoid asking ‘Closed Questions’ that can be answered with “yes” or “no”. Instead ask questions leading with “How” or “What”.


This process gives you a system to follow, to take out the guess work from being able to capture the stories, wisdom, opinions and history of anyone that you want to interview, because one day, you’ll be glad you did.