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Gather as much information as you can.
Name
Age
Where he studied
Family: Parents / Spouse / Children
Pets
Occupation

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1) The more you know, the better the questions you can come up with
2) You can use it as a reference - helps you understand the interviewee a little more before meeting
3) Has someone already asked your questions? Yes? Then you don't need to ask it again, you can spend the time asking something else

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Lee Hsien Loong

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10 February 1952 (69 years old)

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Father: Lee Kuan Yew
Mother: Kwa Geok Choo
Siblings: Lee Hsien Yang, Lee Wei Ling
Wife: Ho Ching
Children: Li Xiuqi, Li Yipeng, Li Hongyi, Li Haoyi
Pets:

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Commanding officer of the Artillery Gun Battalion

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Nanyang Primary School
Catholic High School
National Junior College
Harvard Kennedy School (1980),

He was a Senior Wrangler, the top mathematics undergraduate at Cambridge University in England

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https://sg.news.yahoo.com/lee-hsien-loong-applauds-efforts-games-bound-athletes-amid-pandemic-011724963.html?guccounter=1&guce_referrer=aHR0cHM6Ly93d3cuZ29vZ2xlLmNvbS8&guce_referrer_sig=AQAAAHGUrzK7Q0qHK93v_UHvF-rYExDbZaf1elCUWLSC5uj49dK7BWSougMmXk5BA0zXVeM7Mm50lMjK_-Oyy7_QzdTymGqWJ5NEz2Eh9j7gvdssRE1yaBkfDOBzCB5Vd00c5TZmQs0OzwGk7lYXMBodGM9Jd6qzLpsRmE9rl-h6RWmS

Paste URLs here, let your fellow members have a read

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Computer programming

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https://www.channelnewsasia.com/news/singapore/tengeh-reservoir-floating-solar-farm-officially-opens-15217646

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Peranakan (from Lee Kuan Yew, his father)

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https://www.straitstimes.com/singapore/politics/indonesias-coordinating-economic-minister-calls-on-pm-meets-singapore-ministers

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His dream job was to become a teacher or lecturer, not prime minister

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Things he would tell his 20 year old self

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Things he would tell his 20 year old self

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Things he used to struggle with and how he overcame them

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Things he used to struggle with and how he overcame them

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If you were to go back in time, what would you do differently as a 20 year old?

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What did you regret not doing  back in school?

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What did you regret not doing  back in school?

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What is your favourite music genre and why?

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What is your favourite music genre and why?

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what are some of his favourite new artist , like shawn mendes 

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what are some of his favourite new artist , like shawn mendes 

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what is his favourite memory during his school days?

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what is his favourite memory during his school days?

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one of the things that made an impression on ?

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one of the things that made an impression on ?

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What would you consider your biggest accomplishment during your elementary and high school years?

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What kind of YOLO moments did you have as a student?

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What kind of YOLO moments did you have as a student?

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what advice would you give to your 20-year-old self?

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what advice would you give to your 20-year-old self?

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what was your favourite food to eat in school?

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what was your favourite food to eat in school?

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how are your school days different from schools now  

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how are your school days different from schools now  

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What is your biggest regret that you wanna change real bad?

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What was your proudest moment in your 20s?

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What was your proudest moment in your 20s?

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How did you customise ur friendster profile

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How did you customise ur friendster profile

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which was your favourite decade of music?

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which was your favourite decade of music?

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When is your proudest moments during your school days?

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When is your proudest moments during your school days?

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If you could recommend us to listen to three songs, what would they be?

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If you could recommend us to listen to three songs, what would they be?

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do you enjoy playing any instrument/music?

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do you enjoy playing any instrument/music?

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if so, what genre?

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what music  your family and you like to listen too 

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what music  your family and you like to listen too 

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as a follow up can ask who has the best music taste according to him in his family .

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what are your spotify playlists (if you have any) called?

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what are your spotify playlists (if you have any) called?

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What songs would you recommend to youths?

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What songs would you recommend to youths?