Six Insightful Questions That Can Ramp Up Your Success

Six Insightful Questions That Can Ramp Up Your Success

Key Takeaways:

  • Asking insightful questions can help you build rapport with key people who can enhance your success—and provide you with important information that can give you an edge.
  • There are six questions that the self-made Super Rich systematically ask during their conversations with important people in their lives.
  • Deep listening skills are also required to improve your results.


Want to see amazing results in your business and your life? Try asking questions instead of giving orders or monopolizing every conversation!

The source of that advice? The self-made Super Rich—those with a net worth of $500 million or more.

Indeed, 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—partners, staff, other team members—in ways that generate much better outcomes.

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

The importance of insightful questioning

Being adept at using carefully chosen insightful questions serves a number of purposes (see Exhibit 1).

It enables business owners (and highly successful people in general) 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 the other people because it seeks to create deeper levels of understanding of all the people involved.

It is 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 the other people, too.

The top insightful questions to ask

To see how this approach can benefit you and your agenda, consider the following six insightful questions that many successful entrepreneurs tell us they regularly use in their conversations and dealings with others who are (or may be) important to them.

For each, we include when and how to best use the question to be more successful.

Question #1: What do you think?

Rationale: 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.

When: The question is useful throughout your relationship with anyone. Anytime action needs to be taken, it is usually very useful to know where the other person stands.

Objectives and benefits: 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.

Question #2: What do you want to accomplish?

Rationale: Everyone has an overall agenda. People have goals and objectives that matter very much to them. Knowing what those are is valuable to you as you pursue your agenda.

When: From the beginning of and throughout the relationship, it is worthwhile to understand what the other person wants to do and, if possible, why he or she wants to do it.

Objectives and benefits: This question can address the big picture or be focused on specific endeavors. Knowing what a person you are dealing with 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.

Question #3: What’s the most important thing we should be discussing today?

Rationale: 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 can adversely impact the relationship.

When: This question should be used at the start of every meeting. It may also be appropriate when a meeting is going off track because the other person is not meaningfully engaged.

Objectives and benefits: You want to make sure you are truly being responsive. At the same time, you want to move your agenda along. Neither of these is possible unless you are 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.

Question #4: Can you tell me more?

Rationale: It is quite common for someone to put forth a position that you might not find completely clear. Many people err by making presumptions that may be inaccurate and, consequently, detrimental to the relationship.

When: The question is best used often and everywhere. It is very appropriate with other people and situations where knowing more is highly advantageous.

Objectives and benefits: The better your understanding of the other party’s thinking, the more successful you will be. By prompting the other person to go deeper, your knowledge of his or her worldview and circumstances increases. The result is superior understanding that can readily translate into superior deliverables and greater rapport.

Question #5: How can I be of greatest help to you?

Rationale: 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.

When: This question is appropriate whenever there’s an impasse in a discussion, or when the other person is dealing with some difficulties. It is applicable from the start of and throughout your relationship.

Objectives and benefits: From basic caring and concern to helping facilitate success to meaningfully building and enhancing rapport, your willingness to help the other person can pay enormous dividends. Whether or not you are ultimately able to accommodate someone, your determination to try to address the matter is a powerful bridge builder. What’s more, the law of reciprocity tells us that when you voluntarily help someone, that person feels a natural inclination to want to return the favor and help you down the line.

Question #6: Why don’t you tell me about your business (or job, or career)?

Rationale: You are making the effort to truly understand what may very well be a critical part of a person’s life. Gaining perspective on how the other person spends a great deal of his or her time and effort is often useful.

When: This question is especially effective at the beginning of a relationship. However, it can be very useful anytime there’s a significant change in the person’s business or personal life.

Objectives and benefits: As an entrepreneur, you know that the way people create wealth is often at the core of their identities—to a large extent, it’s who they are. Knowing how they think and feel about their vocations can be very important in building rapport. There’s also the benefit of gathering intelligence on the scope and characteristics of their networks—the people they know and associate with, who may be valuable to your goals.

Be an engaged listener, 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 listen deeply, 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.

Careful listening of any kind requires time, attention, focus and intellectual effort. Here are some ways to make it happen:

  • Prepare to listen deeply. Start by creating the intention of having a great conversation 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.
  • Listen for what is spoken and unspoken. 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.


VFO Inner Circle Special Report

By Russ Alan Prince and John J. Bowen Jr.

? Copyright 2018 by AES Nation, LLC. All rights reserved.

No part of this publication may be reproduced or retransmitted in any form or by any means, including, but not limited to, electronic, mechanical, photocopying, recording or any information storage retrieval system, without the prior written permission of the publisher. Unauthorized copying may subject violators to criminal penalties as well as liabilities for substantial monetary damages up to $100,000 per infringement, costs and attorneys’ fees.

This publication should not be utilized as a substitute for professional advice in specific situations. If legal, medical, accounting, financial, consulting, coaching or other professional advice is required, the services of the appropriate professional should be sought. Neither the authors nor the publisher may be held liable in any way for any interpretation or use of the information in this publication.

The authors will make recommendations for solutions for you to explore that are not our own. Any recommendation is always based on the authors’ research and experience.

The information contained herein is accurate to the best of the publisher’s and authors’ knowledge; however, the publisher and authors can accept no responsibility for the accuracy or completeness of such information or for loss or damage caused by any use thereof.

Unless otherwise noted, the source for all data cited regarding financial advisors in this report is CEG Worldwide, LLC. The source for all data cited regarding business owners and other professionals is AES Nation, LLC.


Securities offered through LPL Financial. Member FINRA / SIPC. Investment advisory services offered through NewEdge Advisors, LLC, a registered investment adviser. NewEdge Advisors, LLC and Congruent Wealth, LLC are separate entities from LPL Financial.


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