Having a reputation as someone who asks insightful questions is good for you and whoever is on the receiving end of your questions. People respect someone who asks good questions—and listens to the answers. And when someone respects you, they’ll want to do more business with you and refer others to you. Asking good questions costs nothing but reaps a plethora of returns.

Good questions allow an individual their “star turn” on the stage of life.

Imagine that your office is a stage on which is being performed a drama on personal finance. The narrator describes the setting, the lights come up, and the spotlight is on the lead actor, your client. In this production, you are in a supporting role. If you keep this in mind, you will realize that most of your good lines in this script are intelligent questions, not clever witticisms or brilliant sales pitches. One of the greatest favors you can do for your clients is to establish at the very beginning of each conversation that your spotlight is pointed on them. Not only will they be impressed by your interest in them and their world, they will also warm to you in the glow of that spotlight.

Good questions elevate an individual’s intellect and reason.

Do you ever notice the types of people that tend to dominate conversations? They tend to be people who are in love with the sound of their own voices and opinions. They often start with, “What do you think about such and such?” and before you can even answer, they jump in with, “Well, I’ll tell you what I think . . .” and proceed to demonstrate just how highly they think of what they think. But when you do the asking instead of the telling, you elevate the intellect, reason, and thoughts of the other party. Rare is the person who will resist your attempts to truly understand them—their thoughts and ideas, and how they came by them.

Good questions recognize an individual’s uniqueness.

Talk to any publisher and you’ll hear them lament over how many would-be authors think they have a story to tell. But if you look at how many books are published each year, one fact emerges: everyone does have a story to tell. While every person’s story may not be interesting to someone else, it is interesting to them—and they want to tell it. The problem is that not many people want to sit and listen to those stories. Even more unusual is someone who attempts to cajole stories out of people. The advisor who acts as biographer will find that clients feel more connected and loyal to someone who cares enough to seek out and listen to their personal stories. Great things lie in store for the advisor who acts as biographer and discovers the story lines that make each client unique.

Good questions reveal priorities and important issues.

What would your client be talking about if you weren’t doing the talking? Probably about an issue they felt was important, even critical. One advisor told me the story of how he gave what he considered a sterling presentation of an opportunity in a bio-tech company. At the end of his 15-minute presentation, his client looked at him and responded, “No way!” When the advisor asked him why he felt that way, his client replied, “My brother-in-law lost his shirt in biotech when the FDA failed to approve a drug.” This advisor told me, “I wish I’d asked how he felt about this type of investment before I gave my brilliant presentation.” An important feature of asking well-thought-out questions is that we help our clients sift through their own priorities and focus on what is most important to them:

  • What is the most important financial issue in your life at this moment?
  • What is going on in your life right now that could have a major financial impact?
  • What do you see as the biggest threat to your financial security?
  • If you had all the money you would ever need, what issue would you first address?
  • What do you want your money to do for you?

You can use questions like these to help your clients figure out what matters most to them—and how you can help them achieve their goals.

Good questions raise personal awareness and often help save clients from themselves.

Most of us don’t have to look much further than the bathroom mirror to see someone who has done something really stupid––including with his or her own money. Some of us are aware of our vulnerabilities; others are only subconsciously aware and continue to fall into the same self-sabotaging money patterns. Maybe it’s mismanagement of debt, or the inability to say no to a can’t-miss opportunity. Regardless, good questions can help bring destructive financial habits and patterns to the surface and provide an opportunity to show your clients how to form constructive money habits.

Good questions have a disarming effect.

Especially when markets are volatile, your clients might want counsel more than advice on what to do next with their money. In fact, they may even be defensive, assuming they are about to be “sold.” Address their fears upfront: “What effect has this [fill in the negative experience] had on you?” This question gives your clients permission to unload their frustration and disappointment. It will disarm the tension they might have expected in this meeting. You can then focus on what matters most: helping your client understand what their short-term and long-term goals are, and how to achieve them. The most successful advisors not only allow clients to express their feelings of what has happened to them, they welcome it. When clients (or prospective clients) walk into your office expecting to be “sold,” and instead, you ask questions, clients relax. And when clients relax, they are in a better position to listen and make the right decisions.

Good questions reveal possible connection points.

Although it would be difficult to make a meaningful connection with every person we meet, the lack of connection that we sense with many people is the result of a lack of effort on our part. If we seek a connection point, we can usually find one. It may be someone we both know, a hobby we share, a place we have been, a book we have read, a view we share, a common faith, commonalities growing up, our parents’ jobs, or something else. If you view your role as a biographer first and advisor second, you will invariably find connections with every client. If you view yourself as a salesperson, you will unwittingly speed past common ground and miss the opportunity to connect.

Good questions turn conversations into a fascinating journey instead of a dead end.

Have you ever seen excitement in the eyes and the anticipation on the faces of your clients when asked to complete a discovery questionnaire? I didn’t think so. These questionnaires are usually full of quantitative, fact-based questions your clients may have answered scores of times and questions they’d rather not answer in the first place. Anybody can help clients fill out forms, but not everybody can engage those clients in a meaningful way. The difference between dead-end discovery and a fascinating journey is in the quality of the questions you ask––even if you still need that quantitative information.

Good questions unlock the memory bank.

A key to making an emotional connection with any client is engaging in conversations that unlock their memory bank. Reminiscing causes people to reach back into the storehouse of significant experience and draw out the moments and lessons that have made an impact in their lives. Well-designed questions stimulate this process and allow clients to open up areas of discovery that would otherwise go unrevealed. A key to building lasting client relationships is not just knowing where clients want to go but knowing where they’ve been. Asking a client or prospective client to talk about their first “money memory” will unlock their memory bank—and help both of you understand their fiscal philosophy.

Good questions allow your client to be the copilot instead of a passenger.

Too often in presentations clients feel like passengers that are being “taken for a ride.” You need to think in terms of meaningful dialogues instead of narrow monologues. By asking questions, you encourage prospects or clients to espouse their opinions, tell their stories, or articulate their hopes. In effect, you are handing over the wheel to them. You are like the driver education teacher who sits in the front passenger seat and has a brake pedal in case the driver gets too far off course. In that case, you simply ask another question that brings you back to a path where something constructive can be accomplished.

Good questions teach you something about your client you may not have known.

A financial planner who attended a workshop on better client discovery told me, “I had always taken great pride in how well I knew my clients and the quality of our relationships. You could never have convinced me before this workshop that I didn’t know them well enough. But when I used some of the questions and inquiry paths you suggested, I began to learn the kind of details that  a financial planner needs to know––details that could cause the best financial plan in the world to unravel at any moment if not addressed.”

Great minds have always looked for better questions because they are intensely curious. Einstein wanted to know. Da Vinci wanted to know. Steve Jobs wanted to know. You want to know. Great discovery emanates from an authentic well of curiosity. It’s not about simply asking questions. It’s about knowing what it is you want to know and designing questions that will draw those stories out of your clients.