Happy New Year?
Finding the right questions to have the dialogue you need.
"If I had an hour to solve a problem and my life depended on the solution, I would spend the first 55 minutes determining the proper question to ask, for once I know the proper question, I could solve the problem in less than five minutes." - Albert Einstein
We hope you all had a wonderful holiday season and are feeling inspired for the year ahead! This week’s newsletter is all about the power of questioning—a tool to unlock creativity, uncover hidden insights, and strengthen relationships.
As we step into 2025, here are some thought-provoking questions to spark your imagination and help you embrace the possibilities of the new year:
What new relationships will you build this year?
How will you take steps toward your dreams in 2025?
What chapters of your life will close, and which ones will open?
Who will you thank for their support this year?
Our Next Podcast Episode: Assisting Parents into Assisted Living
As we age, the dynamics of our relationships with parents and siblings shift significantly. In the next episode coming out January 10, my sister Shelly and I share our emotional and chaotic journey of helping our parents transition from their long-time family home of 25 years into a small one-bedroom apartment in an assisted living community. The episode is filled with lessons learned and best practices, offering guidance to families facing similar challenges. In a heartfelt conclusion, our dad reflects on the teamwork that made the move a success and expresses his gratitude.
Helpful Model - Powerful Questions
In the next episode, we’ll explore how asking better questions could have helped us better understand what was truly important as my parents prepared to move to their new home. The original question we asked them was:
What are the essential items we need to pack for you to take to your new home?
At first glance, this question doesn’t seem problematic. However, in hindsight, considering my parents were already overwhelmed by the move and dealing with the challenges of aging, this question was too broad. A more effective question would have been:
In this room (kitchen, bedroom, office, etc) what are the top 3-5 things we need to take with us?
The brain struggles with open-ended tasks, so providing structure—such as a specific limit—helps focus on what matters most. Studies show that the brain can easily manage 3–7 items at a time, making it easier to prioritize and preventing decision fatigue.
The way we frame questions is a critical skill to develop, especially when considering the context and the people involved. When faced with complexity or potential overwhelm, simplify your questions to break through the fog. For instance: "What are 3-5 critical kitchen gadgets you want in your new home?"
When brainstorming creative solutions or seeking innovation, try asking expansive questions like "How might we address our users' needs?" or "What else have we missed in the user experience?" The word “else” gives permission to offer bold or unconventional ideas without fear of judgment.
If your goal is to build empathy and understanding, ask questions that delve into emotions, fostering psychological safety: "How are you feeling about this upcoming conversation?" or "What are you most concerned about going wrong at this event?" or "What are you most hopeful about?"
To unlock hidden memories or details, consider asking simple but thought-provoking questions like "What else did you see?" or “Why do you think that happened?.” This technique is often used by journalists to uncover new information or details not previously revealed.
In connection with last week’s episode on gamifying major projects like writing a novel, John told me about the “Smoke Game” that writers sometimes use. This clever approach uses questions to help us tap into creative problem-solving. Here’s how it works:
Think of a character—whether a famous person or someone from your novel. Ask questions like:
What kind of “smoke” does this character produce? Is it thick and green? Black and ashy? Light and fresh?
What type of “house” would this character live in? A beach house? A tiny house? An RV?
You ask a series of metaphorical/symbolic questions, and pretty quickly, people are able to figure out the identity of the character. This demonstrates our brain’s ability to navigate based on symbols. But it works in other dimensions; e.g., asking your parents for the three most important things in each room will very quickly give you a feeling for what does and does not matter to them. For more ideas, check out this page.
Contact and Feedback
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We also love any feedback from listeners. Have you put any of this into practice in your own life? Any ideas that stick with you?
Tell us about people we should talk to, or give us feedback, by emailing us at feedback@hindsightretros.com.
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