The Art of Asking

Notes from Sundays’ dinner on April ‘18

Introduction — A Quick Manifesto on Sundays

Sundays is a dinner series that happens once per month in New York City. We bring leaders from all different backgrounds and careers together in a space that promotes vulnerable conversation and ultimately — connection.

We believe that genuine sharing is a catalyst for creation. It’s the energy that transforms relationships and makes transactions secondary.

We’re building a community where truth and support are valued higher than advice or strategy. We think people are awesome, as is, already, and don’t need to be told which direction to go or what to do. Our purpose is to create, empower, and support woke leaders across industries and cultures.

Our vision is one of abundance. More sharing + connection = greater potential + amplified possibilities. In reality, we believe this shows up in the form of powerful leaders, conscious companies and nonprofits, and creative projects that push culture forward and enhance the human experience.

Most of us are entrepreneurs, investors, and business leaders. All of us are human, and we all need help. Thus sets the stage for the conversation that took place at our second dinner of 2018 — The Art of Asking.

Framework for Discussion

Our dinners have a conversation framework that we think promotes authentic sharing and holds a group of 16 people to one conversation, at least for some portion of the evening. The framework allows us to learn through listening and sharing from experience, instead of trying to win (or lose.)

We also eat delicious food, drink fantastic wine, laugh, shout, and end each evening with ice cream.

  1. Speak from I. At Sundays, we do not give advice. We share. We ask our attendees to speak from personal experience about what’s working for them and what isn’t. We ask why, offer support, and make suggestions. “Have you tried XYZ, it’s working for me and here are the benefits I’m seeing from XYZ,” is different than saying “You should do XYZ, I think it would really work for you.” Let’s face it, we have absolutely no idea what will work for other people — because we’re us, not them.
  2. Respect the speaker. (No abrupt interruptions please!) This one is straight forward. Each one of us has awesome stuff to say, and it usually takes listening really close to get the gold nuggets in conversation.
  3. Talk about ideas and concepts, not issues and other people. The problems and the people causing them are clear. We all get the news. Let’s talk about how to solve them and create opportunities, not dwell.

The Conversation

Led by Anna Bouma and inspired by Amanda Palmer’s book “The Art of Asking: How I Learned to Stop Worrying and Let People Help,” this Sundays’ dinner conversation centered on the power of asking.

Whatever you’re building, whether it be a relationship or a startup, requires help from others. And anything we receive in life — whether it be advice, an experience, music, money, knowledge, or otherwise — comes through other people. In our experience, it’s not always our first nature to ask for what we want, need, or believe we deserve. We decided to make the art of asking the topic of discussion at our second dinner of 2018 because it’s of our opinion that mastering the language we use (both in tone and word ) when making requests can shift our reality and redefine what’s possible. It can be the difference between a life and career that’s working, and one that’s not.

Asking for help with shame says: You have the power over me. Asking with condescension says: I have the power over you. But asking for help with gratitude says: We have the power to help each other. — Amanda Palmer

Here are the primary takeaways from our Sunday evening conversation:

  • Asking is a muscle. The more you do it, the easier it becomes. Start small and be bold— make a list of requests that might seem scary, and try making one per day. You might even want to ask for help in compiling your list of requests! See, you’re already getting the hang of it.
  • Ask from a position of authenticity and power. Counterintuitive at first, but making bold requests isn’t about what you’re looking to get out of the situation. Asking from a place of authenticity and power requires enrollment — understanding what the other person wants to achieve, what motivates them, and presenting them with an opportunity to contribute to you which leaves them touch, moved, and inspired.
  • Be clear in your ask. Focus on what you’re looking to accomplish, not what you’re looking to “get”. An easy example is asking for a consulting fee in return for an engagement. Focus on the partnership, what you’ll create together, and how both parties will benefit from a workable solution.
  • Stand firm in your ask. Settling for something that you’re not 100% happy with can lead to resentment. It’s easier to show up for the other person, when we receive the value we’re looking for from the relationship.
  • Great asks have network effects. Sometimes, the person you’re asking simply can’t give you what you’re looking for (or chooses not to). That’s okay. They might know someone else ready to jump at your request. If you’re clear in your ask and genuine in what you’re out to accomplish, you’ll manifest the people who can make it happen through others.
  • Ask from abundance. If you believe the world is an abundance place, you don’t need to worry about anyone saying no. What you’re seeking is out there. Stay patient and focus on your mission.
  • Giving is a gift. People want to support causes they care about, buy products that make them feel good, and work with great people. You’re a great person, so why wouldn’t the people in your life show up? Chances are, your crew, coworkers, boss, family — they’re all just waiting around for you to ask. And they’re wondering what’s taking you so damn long.
  • Know the value you bring.Everyone has unique value to bring to the world. Knowing what it is makes it easier for people to work and play with you. Not sure what your “super power” is? Yup, there’s an ask there too. Survey your friends and coworkers. Dig in with your friends to determine what your strengths and weaknesses are, what you can be counted on for and what you cannot be, and what your unique value is.
  • Be a luxury item. When you set your value low, or beneath where you think it aught to be, that’s exactly who you become. This rings true both in business and in relationships. Aiming low means receiving value less than you deserve, by your own standards. Now think about your highest self. How would you price the luxury version of you? What would you ask of your partner, friends, colleagues, or customers?
  • Ask from I, and have a framework. Asking gets trickier the more important, or “touchy,” the subject around the ask is. Start by explaining why you’re making a request, and why it’s important to you. A simple framework for this is: A) Give relatable context to the other party and state why the matter is important to you, B) speak from I, and focus on what you’re trying to accomplish, C) ask clearly, and express gratitude to the person for participating in the conversation and contributing to you.
  • Language includes tone. Choose your tone, as well as your words. Your body language and the pitch in your voice often say just as much as the words coming out of your mouth. Be intentional in how you speak.
  • Align your day with your intention. It’s easier to ask for what you want when your actions are aligned with your intention. My personal framework for intention setting is a journal entry I make each day. I’ve included the framework below for those interested.

I’d like to personally thank each person who’s attended a Sundays (or prior iteration of this dinner) for their continued support. Our community is set to evolve over the next year, and we’ve never been more excited for what’s next.

Leaders in Attendance



Recommended Learning Material

Let Your Life Speak, Parker Palmer

The Art of Asking, Amanda Palmer
Deep Work, Cal Newport
Mating in Captivity, Esther Perel

Beautiful Money, Leanne Jacobs
The Year Of Magical Thinking, Joan Didion
The Four Agreements, Miguel Ruiz

The Creative Habit, Twyla Tharp

The Psychological Commentary, Maurice Nicoll
My Next Guest, David Letterman’s interview with Jay-Z (Netflix)

Wild Wild Country (Netflix) 
Superforcasting, Philip E. Tetlock & Dan Gardner

Americanah, Chimamanda Ngozi Adichie

Creativity, Mihaly Csikszentmihalyi

Innumeracy, John Allen Paulos

Peopleware, Tom DeMarco & Tim Lister
The Hard Thing About Hard Things, Ben Horowitz
Negotiation Genius, Deepak Malhotra & Max Bazerman

Annihilation, w/Natalie Portman (film)
Sapiens, Yuval Noah Harari
Wait But Why, Tim Urban (blog)

Surely You’re Joking, Richard Feynman

Sapiens, Yuval Noah Harari
Zen Mind, Beginner’s Mind, Shunryu Suzuki

Daily intention setting framework

  • “Today I declare that I am the possibility of ______________.”
  • Fill in the blank not with a thing, but a way of being. Words I often use include “courage,” “connection,” and “freedom.”
  • “My big game for today is ______________.”
  • Fill in the above with something that requires making a bold request.
  • “Today, I am grateful for ______________, _____________,…”
  • Write down as many things you’re grateful for as you can think of quickly, including what you’re grateful for about yourself.