Here’s How Asking the Right Questions Can Boost Your Success

Key Takeaways

• Asking insightful questions can help you gain important information, build trust with others and get closer to meeting your goals and agenda. 
• There are six key questions that you should look to ask when you’re in front of people who can help you succeed.
• Don’t forget to listen deeply, too—you’ve got to pay attention to the responses you hear. 

Want to see strong results in your business and your life? Interested in building better long-term relationships with prospects, influencers and others who can be helpful to you in achieving your goals? Or maybe you’d just like healthier back-and-forth interactions with your spouse or partner.

Here’s a tip: Do a lot less talking. 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. In our experience, a surprisingly high percentage of the most successful people make a point of showing interest in the people around them and demonstrating that they want to understand those people better. They even consistently and systematically ask insightful questions 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—and how you can emulate their approach.

The importance of insightful questioning

Most of us don’t spend much time thinking about how to ask good, thoughtful questions. Usually we’re more focused on doing the talking and “getting our message” out there. When others talk, we might half-listen as we wait to start talking again. But, of course, no one wants to be talked at all the time. 

The upshot: Being skilled at using carefully chosen insightful questions serves a number of purposes. For example:

It can enable 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 collaborate or work together that might not have been obvious otherwise. This can be an especially useful skill for business owners, professionals and any of us who need to enlist others to help us get what we want.

It facilitates rapport between you and the other people because it seeks to create deeper levels of understanding of all the people involved. When people feel heard and understood, their trust in the people seeking that understanding tends to rise. 

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. In other words, smart questions can help you learn how you can help someone who is important to your goals get what they want!

The top insightful questions to ask 

To see how this approach can benefit you and your agenda, consider the following six insightful questions that highly successful business owners and professionals 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.

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 are always beneficial. Furthermore, this question helps you foster involvement in the process at hand—thereby building rapport and ensuring closure. 

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.

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 those 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 sync 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.

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 in 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. When you prompt 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.

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 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.

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 some significant change in the person’s business or personal life. 

Objectives and benefits: The way people create wealth is often at the core of their identities—to a large extent, the income-generating work they do is 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 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.

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.

Conclusion

There may just be a good reason why we have two ears but only one mouth. The ability to uncover information and build rapport through open, shrewd questions and active listening techniques could help you stand out from your peers—and your competitors—in ways that could result in significantly more success.

VFO Inner Circle Special Report By John J. Bowen Jr.

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