What first impression do you hope you make on people?

What is the most memorable meal you've ever had? (It can be good or bad.) What made it so memorable?

Who helped you recently?

What advice do you wish you'd received earlier?

What area in your life are you looking to improve?

What's something expensive you splurge on that you believe is worth the money?

What areas of personal development do you feel you need to focus on to to achieve further professional success?

What do you think is the best place or way to meet a signifcant other?

What word describes your essence the best?

What's a recent moment in which you're proud that you spoke up?

What is something you never thought you'd be able to do, until you actually did it?

What's been on your mind a lot lately?

What's a great piece of advice you recently received? Who was it from?

What is your most terrible memory?

What was your first job ever?

Who is someone you think about a lot, that isn't thinking about you nearly as much? What do you make of this?

When was the last time you had a difficult conversation? Who was it with, and how did it go?

What's your favorite non valuable item you'll keep to the grave?

If you could change anything about the way you were raised, what would it be?

How's your family doing?

What lesson have you had to learn again and again?

Is there anyone close in your life that perceives you differently than you perceive yourself?

What inaction or missed opportunity do you regret?

What area in your life do you feel you’re making progress? Not making progress?

What's a recent disagreement or conflict you had in the workplace? How did you handle it?

What are 3 words you'd used to describe how you currently feel?

Who in life has inspired you the most?

The world needs more of my...

What would people be surprised to learn you spend a lot of time on at work?

What behavior or trait immediately makes you respect someone?

Who in your life always makes you laugh?

What's a funny or embarrassing moment you’ve had at work?

What’s something at the top of your to-do list?

What movie traumatized you as a kid?

Explain your current feelings in life to a 3 year old.

What is one commitment you've made to showing up differently in a particular relationship of yours?

Where were you born?

How’s your heart today?

What are your biggest goals between now and the next issue of our Letterloop?

What's the most bizarre dream you've ever had?

If your life was a story, what chapter would you currently be in, and what would its title be?

How can you better help others succeed, especially those who often go unnoticed?

What are you most proud of right now?

What's a habit you'd like to adopt, but find difficult to stick to?

Think of one of your big, lofty goals. What small step could you take today towards achieving it?

How well do you feel your work aligns with your purpose or identity?

What's one work-related skill you'd like to develop, and why?

What's one thing you've never done but feels like it's something you need to do in your lifetime?

What tools or apps do you find indispensable for your work?

Where do you wish you had grown up?

What's the worst advice you've ever been given?

Where do you see yourself professionally a year from now?

What was your "rock bottom"? How did it happen, and how did you get out of it?

Who here is is most likely to join the secret service?

What's a movie you can watch over and over without ever getting tired of?

Is there anyone you envy? If so, whom and for what?

Explain your job to a 3 year old.

What's currently worrying you?

If you could have dinner with any person, living or deceased, who would it be and why?

What traits in others are you attracted to?

What does "success" mean to you, and how has that definition evolved over time?

In what ways are you similar to your parents? In what ways are you different?

What's your favorite toy?

What is something you're coming to realize?

What's your favorite way to relax these days?

How would you describe your approach to your career so far?

If you could change one thing about yourself physically, what would you change?

What's a goal or project you've made progress on?

What's your favorite personality or character trait about yourself?

Can you share an instance where your first impression of someone was completely wrong?

What have you been dreaming of eating lately?

Think of your biggest regret. If you could go back in time and make a decision to keep it from happening, would you?

What's the hardest part about maintaining relationships for you?

Who here is is most likely to look almost the same years from now?

If you had to choose a theme song for your life, what would it be?

What's a deep or difficult question you've been pondering lately?

What self-limiting beliefs do you currently hold?

When was the last time you experienced stillness and wonder?

Who here is would most likely become a CEO at a company ranked amongst the top 100 largest in the world?

What boundary did you recently set that has improved your relationship with someone?

Which superhero’s powers do you feel are underestimated?

Who here is most likely to bring an axe to a pillow fight?

Given the choice of anyone in the world, whom would you want as a dinner guest?

Have you picked up any new skills at your job this year?

What do you most need to hear right now, and from whom?

What is the most ordinary-seeming thing that you find fascinating?

What career decisions have you made based on fear? What decisions have been based on confidence?

Are you closer to one of your parents than the other, and why?

Can you share an unexpected goal you have for this year?

What kind of a day have you had so far today?

Can you share a personal tradition that holds deep meaning for you, and explain its origin?

What fact about yourself took you the longest to understand or accept?

If every time you snapped your fingers, you would instantly and irreversibly be transported to a random point in humanity's timeline, would you snap your fingers? If so, how often?

What's a deep question you often ask yourself?

What instantly makes you think less of someone?

What's the most challenging thing you're working through these days?

What's one thing you do to distract yourself that you think you should less of?

How would you summarize your last 12 months in one sentence?

If you could have a superpower that helps you in your current job, what would it be?

What talent of yours do you consider to be inherent, like an advantage you were born with?