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Use Powerful Questions to Boost Your Executive Functioning and Enhance Your Life

Executive functioning is the key to contentment in our personal and professional lives. Completing daily tasks, learning, solving problems, maintaining healthy relationships, preventing overwhelm, and accomplishing our long-term goals hinge on competence in executive functioning. One way to boost executive functioning is through powerful questions that lead us to insights that affect our judgment and performance.

Let’s start with an understanding of powerful questions. After that, we can consider each executive function (awareness, time management, organization, task initiation, self-control, emotional control, sustained attention, prioritization and planning, goal-directed persistence, working memory, and flexibility). We’ll see how the right questions lead us to the best answer and most effective actions to improve our executive functioning.

The Right Question Leads to the Reversal of Misfortune

Have you ever had a serious problem that didn't seem to have a solution? Perhaps it involved your relationship, job, or finances, as in Mark Cook's case. Mark's priorities were his family, farming, and trading. One day, all three were jeopardized, throwing his life into disarray. Here's his story.

Mark became a stockbroker in 1979. Over the next few years, he started taking bigger and bigger risks in the market. Then everything collapsed. He suddenly had a deficit of $350,000 and "lost over $100,000 apiece" in his mother's, father's, and aunt's accounts. (That would be a total of $2,718,182 in 2023.)

Red arrow going steadily downward.
The value of the stocks was plunging.

After Mark told his mother, she asked, "What else?" He couldn't understand the question. She explained that she was concerned that he might also have had a serious illness. Amid this confusion, clarity emerged when his mother asked, "How long would it take to get the money back?" That question gave him hope. He immediately began to figure out a timetable and a way to get out of this mountain of debt. After carefully calculating, he answered with determination, "Five years."

By working long days on his parents' farm and moonlighting as a broker at night, Mark reached the break-even point by 1985, a mere three years after his financial crisis. His efforts prevented bankruptcy, restored financial stability, and created the foundation for decades of happiness. He lived his dream life - enjoying his family and farm while making millions trading. By 1992, this stock market wizard was a highly sought-after speaker and an advisor for aspiring investors wanting to learn his trading system.

Today, Mark's legacy endures through his "Pathway to Trading" platform, which offers contemporary investors hope and services. It's fascinating to think that the pivotal event for Mark came when his mother asked, "How long will it take to get the money back?" That seemingly simple question was the catalyst that propelled Mark toward his path of both personal fulfillment and financial accomplishment.

Q-Storming: Questions Matter

Lou Holtz, American Coach

Q-Storming is a practical problem-solving approach. Instead of brainstorming answers, you brainstorm good questions. These thought-provoking questions serve as a catalyst for new ideas and possibilities.

Here’s how it’s done. You set a time limit, like five minutes, or select a goal, like twenty questions. Then list as many questions as you can. After that, you read over the questions and pick your favorite. A good question will get you thinking about the situation and possible solutions.

When moving forward seems impossible, the right question can lead to a breakthrough of clarity, commitment, and action. You can find more information on Q-Storming in Marilee Adams's book, Change Your Questions, Change Your Life, and on the Inquiry Institute website.

Powerful Questions Start with What or How

"Why", "When", and "Who" are usually ineffective starters for brainstorming questions. John G. Miller gives this explanation. "Why questions" might result in regret or blaming. When questions may lead to procrastination. "Who questions" can have us looking for a scapegoat.

Start with “what” or “how” to make your questions powerful. Answers to “what questions" provide needed information. “How” questions lead to understanding the steps to be taken or the strategies to use. While Mark Cook's mother could have started with "when," her choice of "how long" suggested that he would contemplate and comprehend his time frame for becoming financially solvent rather than arbitrarily selecting a date without thoughtful consideration. “What” and “how” questions are essential in problem-solving.

Powerful Questions that Lead to Better Executive Functioning

Each of us has challenges in executive functioning. Rather than feeling inadequate or stuck, create questions that serve as a stimulus for improvement. When faced with difficulties in a particular skill, refrain from self-deprecating questions like "Why am I so bad at this?" Instead, generate positive, future-oriented, constructive questions. Here are examples of questions that get us thinking about ways to improve our executive functioning.

Powerful Questions to Improve Awareness

- How am I feeling?

- What do I need?

- What triggers do I have to be aware of?

Powerful Questions to Improve Time Management

- How can I handle disruptions?

- How will I avoid overcommitting and overpromising?

- What’s an example of a time I managed my time well?

Powerful Questions to Improve Self-Control

- What behaviors show my need for more self-control?

- What strategies can I use to control my impulsivity?

- How will my life improve when I have better self-control?

Powerful Questions to Improve Emotional Control

- How will I recognize my stress level increasing?

- How can I gain control before things escalate?

- What do I want more of in my life?

Powerful Questions to Improve Sustained Attention

- What changes in my environment will help me stay focused on tasks?

- What length of time is reasonable for me to work on a task?

- How can I stay motivated?

Powerful Questions to Improve Prioritization & Planning

- What’s important now? (WIN)

- What are the steps to the long-term goal?

- What resources can I use to be most efficient?

Powerful Questions for Goal-Directed Persistence

- How will I break down larger tasks into manageable steps?

- What can I delegate?

- What can I do to push through the most challenging part of the project?

Powerful Questions for Working Memory

- What is the best place to use as my drop spot for my keys and phone?

- What’s the best tool to help me remember what I must do?

- What routine can I build in my day to free me from having to remember things?

Powerful Questions for Organization

- What small area of my environment can I organize?

- What do I want that area to look like?

- What’s the first step in organizing the area?

Powerful Questions for Flexibility

- How can I learn to accept changes that are beyond my control?

- What’s good about this new way of doing things?

- What out-of-the-box solution can I think of?

Your Turn - Getting Started with Powerful Questions

If you want to understand an issue better, use these steps.

1. Take a moment to think about a challenge you currently face.

2. Set a five-minute timer, and list as many “what” and “how” questions as possible.

3. Pick the most helpful question.

4. Brainstorm answers to that question.

5. Choose the best answer.

6. Take action that is inspired by the best answer.

This exercise directs your focus on the solution rather than on the problem. Your “what” and “how” thinking reveals new perspectives and options, which enhances your ability to resolve the issue. The answer can lead you to action, allowing you to control the situation and your life.

It's been said, "The questions you ask determine what you see." As you begin using skillful questioning, you'll find yourself going from inquiry to insight.

Irene Caniano is a productivity and ADHD coach specializing in executive functioning. She primarily works with individuals in their 20s. Her clients inspired her to write the book Design Your Happiness: 9 Essential Elements to Create the Life You Want. For information or to contact Irene, visit


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