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108 questions to crack the mask and spark connection

Updated: Jun 28, 2020

Just a few shirks, he was only three years old after all.

He hadn’t yet learned how to make up elaborate stories for himself and others to justify his resistance, Befuddled she said if you really don’t like it. You can stop going. He elected to continue going. She continued to bring him conditional on that begin to participate. And on the next visit he did. I call this warming to the room.

I have a reputation of talking to anyone. I’m Irish afterall, but like us all, I don’t see myself the way others see me. I find it hard to walk into a room of strangers and strike up a conversation on cue. I’m gifted at a bus stop, on a train, in the ocean or most other places where something occurs to me and I feel compelled to share it or explore it with the nearest warm body.

Business Networking can often feel like instead of warm bodies there’s a nest of vipers who all equally don’t want to be there among the few that are buzzing with chatter and glee. These beacons of light make you feel worse in the face of their obvious joy. The pain digs deeper if you only like conversations that take you beyond My name is Eilish and I’m a branding expert.’

I often feel unless I instantly display I am entertaining, useful or ‘connected’ then no one has any interest in me so I edge closer to the wall.

The reality is more likely everyone is experiencing their own version of clinging to the edges and thinking why is this stuff so hard while they wait for the tiny proportion of extroverts on speed to break the awkward soundless barrier. Drilling for gold with a canape stick in hard granite might just be easier. However we’re all there to find that gold, that person we connect with and like, who just might become our new best friend, best client or co-creator.

We all know networking is about building relationships, and relationships are the bedrock of doing business and just about anything else. And while we live in a more fragmented and connected world than ever, it’s no longer what you do or even who you know but who knows you.

The reality is each relationship starts with a hello and if you never get past that then you’ll just never know.

Networking builds your brand but it’s also an opportunity to reinforce who you are as you walk your talk.

So let’s revolutionise networking by asking better or more creative questions that might just lead to more real conversations.

Below are some questions to draw out a few closely held secrets, spark ideas, recall stories, crack a smile that might become a full bodied laugh.

Try them at your next meeting, conference, seminar or the coffee queue, with your friends, family and those strangers that are not yet  friends, collaborators and co-creators. It’s about connecting which is really just spreading a little more love. Who knows how and where those seeds will grow and you’ll likely meet some relief and laugh a little more along the way.

With the most random and right question, you might discover something you never knew, about the stranger velcroed to the wall, about someone you’ve known forever or about yourself.  What have you to lose and after all you chose to be there so you might as well get into it.

  1. What has been the best part of your day so far?

  2. What are you longing for right now besides the buffet or a beverage?

  3. What does your inner nerd get deep pleasure from? Mine is . ..

  4. What laws or social norms really get under your skin?

  5.  Would you jump out of a perfectly good airplane? (with appropriate equipment of course) Why/why not?

  6. Are you a starter or a finisher?

  7. Do you feel you are living the life you meant to live?

  8. Do you sit on the woo woo or the science side of the fence?

  9.  Can you tell when someone is lying?

  10. Do you believe in magic? Tell me an experience you had

  11. Do you have a daily practice?

  12. Do you live by your head or your heart?

  13. Do you believe in forgiveness? for everyone?

  14.  Do you pay attention to signs?

  15. Would you rather a happy or a meaningful life? Why?

  16. Do you believe in the paradox of choice?

  17. Where do you stand on social media?

  18. What one habit do you wish you had?

  19. What one habit would you like to stop? What would you replace it with?

  20. Do you have any irrational fears?

  21. Do you have any personal rituals for the moon, new year?

  22. Have you ever (actually) kept a New Year’s Resolution?

  23.  Are you the rescued or rescuer?

  24. What do you get so lost in you could spend hours and days doing?

  25. Do you think you are leading your life or being guiding?

  26. Do you think everyone could be a leader?

  27. What’s the scariest thing you’ve ever done? How did you feel afterwards?

  28.  Who was your favourite teacher in school? Ever?

  29. Where’s the best place you ever visited? Why?

  30. What’s the best thing your Dad or a male ever taught you?

  31. Do you think we’re designed for 8-12 hour work days? How many hours seems right to you?

  32. Do you think we’re designed for monogamy? (Why or why not?)

  33. Do you think you’ve ever operated at 100% capacity? Are you now?

  34. Ever fantasise about being famous? What would you be famous for?

  35. Has a teacher ever changed your life? How so?

  36.  Do you feel safe when you are in love?

  37.  Have you ever dreamed about starting a business? Or if you’ve got one — a new business?

  38. If you changed your name what would it be?

  39. Have you ever fantasised about being a sage? What’s the first question you’d like to answer?

  40. Have you ever had a psychic reading? Did you believe it? Was it accurate?

  41. Have you ever had to publicly admit you made a mistake? Why? How did it feel afterwards?

  42. Have you ever gone on a blind date? How did it go?

  43. Have set up two friends on a date? How did it go?

  44. Do you think people are courageous in their every day lives? How?

  45. Have you ever met one of your heroes?

  46. Do you believe you have 3 brains?

  47. What’s the hardest you’ve pushed your body you ever pushed your body further than you dreamed possible?

  48. Have you ever lost it and screamed at someone? (How come?)

  49. Have you ever met someone you believed was genuinely a bad mother f**ker?

  50. Have you ever stolen anything? (time, love, money, stuff?)

  51. What’s the most fun and illicit thing you ever did?

  52. Do you believe in completely unplugging? For how long?

  53. Have you ever won an award? What for?

  54.  Have you every won something you value? What?

  55. How do you talk to yourself? Are you kind?

  56. How long can you go without checking in?

  57. How would you fix the economy?

  58. If you were online dating website, what’s the top 3 qualities you look for in your potential date’s profile?

  59.  If I gave you $100k and said you can do anything with it as long as it helped more than just you or your immediate circle? How would you spend it?

  60. Do you know your unsolvable problems? Are you ok with them or would you swap them for others? Which ones?

  61. If you were to make your own scent what would it include?

  62. What’s the best thing your mother/father ever taught you?

  63. If you could solve one world mystery, what would it be?

  64. If you could master any musical instrument, what would it be?

  65.  What would you tell your 16 year old self?

  66. What do you believe were/are the greatest gaps in your education?

  67. When you go on a road trip, what’s the one thing you always pack?

  68. If you were to die tomorrow from now, what would you regret most? How you spend the next 24 hours?

  69. If your were a fiction write which genre would you write? What would be your nom de plume?

  70. When was the last time you felt stuck in a rut? How did you break the pattern?

  71. What do people ask you to do or thank you for doing?

  72. What’s your area of expertise? Do you love it or is it just something you fell into?

  73. What are you bored with?

  74. What’s your recurring f**k up?

  75. When you eat mindlessly what do you go for? Sweet or savoury?

  76. What are you devoted to right now?

  77. Do you run to or from things?

  78. What are you freakishly good at, your superpower?

  79. Do you know when a partner is good for you? What signals do you look for?

  80. What’s more important to you time or money?

  81. Would you consider yourself an introvert, extrovert, or ambivert?

  82. At what age was your first real kiss? What was the best kiss of your entire life?

  83. When and where do you get your best ideas?

  84. When was the last time you saw an animal in the wild?

  85. What’s the craziest job you’ve ever done?

  86. Describe your biggest Bridget Jones fashion faux pas?

  87. What’s your epitaph?

  88. What’s the last book that you couldn’t put down?

  89. Tell me 3 things on your must do in this decade list?

  90. What’s always in your fridge? cupboard?

  91.  What’s your abiding dream you haven’t acted on? How come

  92. What’s one mistake you keep repeating (and repeating)?

  93. Who’s your favourite person in the world? Why?

  94. When you see others getting things you want, how do you feel? What do you do?

  95. What’s one thing you’re secretly proud of?

  96. What’s something you’ve tried, that you never ever need to do again, ever?

  97. If you could be any nationality which one would you choose and why? Can you do that accent?

  98. What do you need to be content?

  99. Do you know what drives you?

  100. What’s the worst piece of advice you’ve ever been given?

  101. What’s the best compliment you’ve ever received?

  102. What’s the hardest thing you ever had to write/say — and why?

  103. When was the last time you surprised yourself? How?

  104. What’s your theme song?

  105. What’s your definition of an ideal houseguest?

  106. What’s your guiltiest of guilty pleasures?

  107. What’s your definition of success? AND

  108. What’s just great in your life right now?

I’ve love to hear the answers you get. Email me and let me know.

x Eilish

PS And oh a top tip when you arrive put both feet the ground and feel into your body. Notice if you are more weighted to the right or left. Without moving an atom, redistribute your energy until you feel balanced. When you are in your body, you always know what to say or do. Maybe that’s why it’s so easy for me to chat to random strangers at bus stops.

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