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Business Design School 006 — Question Storming

Published 6 months ago • 9 min read

Question Storming

Curiosity is the Beginning of Everything

Welcome back to Business Design School, a twice-monthly newsletter for the creative-business-curious. I call it a school because we’ll learn to master the art of business design, together.

Reader Response: New top section! I love hearing from you, learning what resonates, and how your replies build on what I’m sharing in this newsletter. Our last issue was about Shared Capitalism and how companies are rethinking ownership to share it with employees and even customers. Reader (and friend) Ryan Larcom from High Alpha Innovation replied with some interesting ideas linking ownership and incentives: “I think one of the most important considerations of ownership is incentives -- who owns the company dictates the incentives: publicly-traded companies with short-term returns, startups (VCs) with 10-years to exit at a 10x valuation, employee ownership with high-quality work, long-term patient capital (for retirement). It’s worth being as thoughtful of the incentive structure that you’re designing (the “game” people will play) as the desire to open up ownership to new stakeholders.” Thanks for your thoughtful reply, Ryan!

In this issue: Questions, questions, questions!

But first: Business Design School is made possible by generous sponsors like our friends at Aardvark. Aardvark is a financial strategy studio for the creative industry. Also known as “the fractional finance department for creative agencies,” they provide all-in-one CFO, bookkeeping, tax, cash management, payroll, invoicing, and other financial tasks needed to run a business. Learn more and sign up for Aardvark’s “Ask Us Anything” event to receive free financial insights specific to your agency or studio: heyaardvark.com/ask-anything


Question Storming

Curiosity is the Beginning of Everything

Design Museum Everywhere produces an annual Workplace Innovation Summit to explore the future of how and where people work. The team and I launched the first conference in 2016, which continues to this day. I’ve always loved this event because we brought so many people together around this topic; after all, we all spend about 25% of our waking hours per week at work. And especially after March 2020 and the COVID-19 pandemic, it’s a critical topic with the fabric of work changing dramatically.

But transport yourself back to 2018 for a second; this is pre-pandemic. The Design Museum produced two incredible Workplace Innovation Summits in 2016 and 2017, covering various workplace topics — and now it was time to plan the third annual event. I don’t want to say we had writers-block (or whatever you call it when conference planners run out of ideas). We certainly had ideas and folks we could tap to speak at the event, but we did cover a lot in the first two conferences — we wanted to do something new and different each year, and we were stuck.

As always, we asked for help. One of our Workplace Innovation Think Tank members introduced us to Joe Mechlinski and his consulting company, SHIFT. We shared our issue with Joe and two SHIFT consultants, Liz Eskenazi and Whitney Siders. We wanted to ensure we were producing content relevant to our audience and connected deeply to their curiosity about workplace design. Their recommendation was simple: if you want to understand what your audience is curious about, ask them what questions they have about it. They advised us to use the Summit event, with hundreds of folks in attendance, for a massive Q-storming — or Question Storming— session.

Question Storming

Question Storming is a dynamic and innovative approach to problem-solving and idea generation. Like its more popular counterpart, brainstorming, question storming revolves around group collaboration to explore a topic from various angles. However, rather than generating ideas or solutions, the primary objective is to create a flood of questions — as many as possible! This technique harnesses the power of curiosity to promote critical thinking, gain deeper insights, and uncover hidden dimensions of a problem or topic.

A question is an invitation to explore and, more importantly, a signal to take action. Question storming encourages a fundamental shift in thinking. It seeks to challenge preconceived notions, assumptions, and biases that might otherwise go unexamined. Question-storming is a process that invites curiosity, the spirit of exploration, and the desire to understand better. You can apply this approach to virtually any situation, from business and innovation to education and personal growth.

Here’s how to do it and how Liz and Whitney led the session at the 2018 Workplace Innovation Summit:

  1. Gather a Group: Bring a diverse group of individuals together, ideally with varied perspectives and expertise, to participate in the question-storming session. For us, it was the hundreds of attendees at the Summit, including designers, entrepreneurs, CEOs, real estate professionals, consultants, educators, and more.
  2. Select a Topic: Decide on the topic or question to explore — this can be a challenge statement or a key question, which becomes the central focus of the session. At the Summit, we asked, “What questions do you have about the future of how and where we work?”’
  3. Generate Questions: Time for some divergent thinking! This process allows participants to explore various dimensions of the topic; it’s not about finding the one question to rule them all; it’s about generating many questions related to the chosen topic — no restrictions! In our case, we put people in groups with Sharpies and Post-its, and folks started covering the walls with questions.
  4. Do Not Answer: The key is to postpone answering the questions. Participants must refrain from attempting to answer the questions during the session — keep the focus on generating a multitude of questions instead. Not answering was hard for some folks at the Summit because they wanted to dive deep or share their thought leadership. We had facilitators in each group, ensuring the focus was on generating questions, not answering them.
  5. Look for Patterns: Every individual question is important, and so are the patterns — try to group questions into categories and prioritize them for future exploration. At the end of our session, we had teams group their stickies into key themes, and each team shared their themes and questions. The questions they generated formed the foundation of our events, magazine articles, posts, and conversations on workplace innovation for years following the 2018 Summit.

Business Design Questions

I recently spoke to industrial design students at my alma mater, Rochester Institute of Technology. It was a professional practice course, so we discussed careers and opportunities for designers. One of the students asked a fantastic question: “What questions would you ask if you were starting a campground business?” Gosh, I loved that question. He didn’t ask, “How would you start a campground business?” He asked what questions I would ask. I’ve never started a campground business, so I’m not sure I could say how I would do it, but I do have questions.

Let’s use his request as an example for question storming. I set a timer for 20 minutes and wrote out 60 questions relating to his key question: What questions would you ask if you were starting a campground business? Here are the first 20:

  1. Who can I start this with?
  2. Where should/can the campground be?
  3. Can I work at a campground for six months while starting this?
  4. What will I say to people when they tell me I’m crazy to do this?
  5. Who are my biggest supporters/champions who can rally me when times get hard?
  6. Who can I pull together to build a trusted advisory group around this idea and regularly ask for advice?
  7. How can I build a community around this idea?
  8. What should we call it?
  9. How can I test this idea before going all in?
  10. What other campgrounds or hospitality companies inspire me?
  11. What value am I creating for people?
  12. What does pricing look like?
  13. Are there any ways I can generate annual recurring revenue?
  14. Who is my ideal customer?
  15. How will I reach my ideal customer?
  16. Could I pre-sell stays at the campground to generate startup capital?
  17. What does the ownership structure of this business look like?
  18. What property/equipment must I invest in to get started?
  19. What’s the ideal experience I want to generate for customers?
  20. What are the insurance and liability requirements for a business like this?

I did this all in Figjam (digital whiteboard) — you can see all the questions here, along with a template for Question Storming and how I grouped the questions and prioritized the themes for next steps. It’s one of my favorite tools for quickly going from nothing to something.

The Socratic Method

Curiosity has evolutionary roots. Throughout human history, our survival and adaptation often depended on our ability to explore and understand our environment. Being curious about new resources, potential threats, and opportunities for cooperation or innovation would have conferred an advantage. The brain’s reward system also plays a critical role in curiosity. When we encounter something new or interesting, our brain releases dopamine, a neurotransmitter associated with pleasure and reward. Our brain chemistry reinforces curiosity and motivates us to seek more information or experiences.

I love asking questions. It’s how I learn. Questions get me through the “what should I do next” moments. I even wrote a chapter about asking questions in my new book, Chapter 6: Distribute Your Ignorance. I start all my projects by asking questions and, if possible, by question-storming with a group of smarter people than me on the topic. It’s such a great way to understand people better. When you pose a question, I think people feel they must have an answer. I prefer igniting their curiosity to create space for thoughtful conversation and learning. If you ask what questions they have, they start to wonder instead. And it’s wonderful to be in a state of wonder.

In that wonder, you can generate dialogue. The Ancient Greek philosopher Socrates is famous for his method of asking probing and open-ended questions, now aptly known as the Socratic method. He used this approach to engage in debates and discussions with others, encouraging them to think deeply, challenge their beliefs, and arrive at a deeper understanding of complex issues. The primary goal of Socratic questioning is to encourage individuals to arrive at their own understanding and conclusions through a series of well-crafted questions.

To help drive your next exploration for meaning and understanding through asking questions, here are some key characteristics and principles derived from Socrates’ approach:

  • Open-Ended Questions: Socrates believed in asking open-ended questions that couldn’t be answered with a simple “yes” or “no.” These questions often start with phrases like “What is…?” or “How does…?” to prompt deeper exploration.
  • Challenging Assumptions: Socratic questioning aims to challenge and critically examine assumptions, beliefs, and opinions. It encourages individuals to question what they think they know and consider alternative viewpoints.
  • Exploring Definitions: Socrates often asked people to define key terms or concepts they were discussing, which helped to clarify meanings and uncover inconsistencies in their thinking.
  • Examining Implications: Socratic questions often delve into the consequences and implications of a person’s statements or beliefs, encouraging individuals to think through the logical outcomes of their ideas.
  • Encouraging Self-Reflection: The method promotes self-reflection and self-discovery. By asking questions rather than providing answers, Socrates aimed to help individuals develop a deeper understanding of themselves and the world around them.
  • Progressive Inquiry: Socratic questioning typically follows a structured sequence, with each question building upon the previous one. This progressive inquiry allows for a systematic exploration of a topic.
  • Respectful and Non-Dogmatic: Socratic questioning is a collaborative and respectful process. It doesn’t involve imposing beliefs or opinions on others but instead fosters a spirit of mutual exploration and learning.

Francis Bacon, the English philosopher and scientist renowned for his advocacy of the scientific method (another great way of questioning the world around you), once said, “A prudent question is one half of wisdom.” Next time you get stuck or are staring at a blank page trying to kickstart your business design work, try starting with questions! Gather a group and question-storm, or create a dialogue with someone using Socrates’ framework. Curiosity will always pull you forward!

I’d love to hear from you: have you used question storming in your work? How does curiosity help you push through barriers and learn? You can simply reply to this email.

If you enjoyed this issue of Business Design School, please share the love on LinkedIn or forward this email to folks you think might enjoy it as well.

Have a great week! Talk soon!

— Sam

PS: The Kickstarter campaign to fund the launch of my new book is rolling along! There are only 9 days left. So far we’ve raised $4,729 of our $8,000 goal — we need you! Kickstarter is all or nothing, so if you’re interested in reading the book and supporting independent design publishing, please consider backing the project today! You’ll receive your print, digital, or audio copy and be the first to read or listen to Adventures in Disruption. I appreciate you!


Thanks again to our sponsor: Aardvark, a financial strategy studio for the creative industry. heyaardvark.com

Sam Aquillano is a business designer and writer. In 2009 he founded Design Museum Everywhere, an online, nomadic museum with the mission to bring the transformative power of design everywhere. His upcoming book, Adventures in Disruption: How to Start, Survive, and Succeed as a Creative Entrepreneur, chronicles his team’s startup journey and is available for order via Kickstarter, launching in October 2023. He's now a Design Director leading business design at Edward Jones. Sam has earned numerous awards for his work, including the Red Dot Design Award, Graphic Design USA’s Responsible Designers to Watch, and Fatherly named him one of the Coolest Dads in America.

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Business Design School

Sam Aquillano

A twice-monthly newsletter for the creative-business-curious. I call it a school because we’ll learn to master the art of business design together. We’ll explore creative entrepreneurship and leadership, how to design things like culture and operations, and consider ways to accelerate business success and impact by design.Sam Aquillano is a business designer and writer. In 2009 he founded Design Museum Everywhere, an online, nomadic museum with the mission to bring the transformative power of design everywhere. His new book, Adventures in Disruption: How to Start, Survive, and Succeed as a Creative Entrepreneur, chronicles his team’s startup journey and is available on Amazon, Bookshop, Barnes & Noble, Apple Books and more. samaquillano.com

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