Church Group Comes to The Rescue And So Can You: Whit & Whimsey

Leadership Medina County has proudly announced this year’s class of 2020, the 29th class to go through the program. The Signature Class is a nine-month leadership program for current and future adult leaders residing or working in Medina County. Participants engage in civic education, hands-on experiences on retreat days such as discussions with key community

Insightful Questions that Can Ramp Up Your Success

Want to see some amazing results in your life? Ask questions and then listen well. We have discovered that a disproportionate number of the most successful people consistently and systematically use an approach known as insightful questioning to build rapport with other people in ways that generate much better outcomes.

Here’s how they engage in insightful questioning—and use it to generate truly impressive success.


Being adept at using carefully chosen insightful questions serves a number of purposes:

  • It enables you to be more effective at garnering useful and important information from other people—such as their goals and the drivers behind those goals. Armed with that information, you can potentially find ways to work together that might not have been obvious otherwise.
  • It facilitates rapport between you and other people because it seeks to create deeper levels of understanding of all those involved.
  • It’s a powerful way to connect with other people and provide you with information that you can use to further your own agenda— often while simultaneously helping them, too.


Asking insightful and thought-provoking questions ultimately won’t help you learn new information or build rapport if you tune out when the other person answers. You must also be adept at deep listening—focusing intently on the person talking through fully present, nonjudgmental listening.

When you deeply listen to someone, it’s almost as though you are suddenly standing next to the person and seeing the world as he or she sees it. You become a comrade or partner. Since most people rarely have the experience of being deeply listened to, this experience of camaraderie is equally rare. The person you’re interacting with will feel more bonded to you as a result.

How do you do it? Start by creating by saying to yourself, “I am going to have a great conversation with this person, and we will both have a great experience.” With so many thoughts buzzing around in your head all day, you must intentionally commit to being as present as possible with the person in front of you. By keeping this intention foremost in your mind, you will greatly increase your odds of success.

Then listen on the surface to the information that the person provides. It’s important that you capture this surface information as accurately as possible. But also listen for the person’s thoughts, feelings, values and needs—which he or she might not come right out and say directly.

ACKNOWLEDGMENT: This article was published by the BSW Inner Circle, a global financial concierge group working with affluent individuals and families and is distributed with its permission. Copyright 2018 by AES Nation, LLC.


Consider the following insightful questions that many successful people tell us they regularly use in their conversations and dealings with others who are (or may be) important to them.


People are very willing to share their opinions and insights if prompted. They want to be recognized for their views and ensure you understand their positions on important matters. Any time you need to act, it’s usually very useful to know where the other person stands. Gathering intelligence and gaining perspective into the thinking and preferences of the people you are dealing with is always beneficial. Furthermore, this question helps you foster involvement in the process at hand—thereby building rapport and ensuring closure.


Knowing what a person really wants to accomplish informs you of the degree of overlap—or conflict—among your and that person’s various agendas. It also helps you frame your desires in ways that best resonate with the other person. This can result in a deeper level of rapport and trust—resulting in a greater willingness to work with you.


It’s normal for people to go into any meeting with an agenda. However, your objectives for the meeting may not coincide with that of the other person, which can lead to wasted time and effort and adversely impact the relationship. Use this question at the start of every meeting or when a meeting is going off track because the other person is not meaningfully engaged. To be truly responsive while moving your agenda along requires you to be in synch with what is important to the other person at that time. This question demonstrates concern and is very useful in addressing critical needs and wants.


It’s quite common for someone to state a position that you might not find completely clear. Many people err by making assumptions that may be inaccurate and, consequently, detrimental to the relationship. The better you understand the other party’s thinking, the more successful you will be. By prompting the other person to go deeper, you increase your knowledge of his or her worldview. The result is superior understanding that can readily translate into superior deliverables and greater rapport.


Most of the time, people are seeking ways they can benefit themselves. The aim of this question is to determine how you can be supportive of and deliver value to the other person. Ask it whenever there’s an impasse in a discussion, or when the other person is dealing with some difficulties.

From basic caring and concern to helping facilitate success to building meaningful rapport, your willingness to help others can pay enormous dividends. Whether or not you are ultimately able to assist someone, your determination to try is a powerful bridge builder. What’s more, when you help someone, that person usually feels a natural inclination to want to return the favor and help you down the line.