Growing Your Question Game: 21 Questions To Ask Clients And Prospects And How To Structure Them For Better Client Engagement

Grow Your Question Game: How To Ask Better Questions During Client Meetings

Advice to financial advisors about better client relationships often starts with the importance of listening. But there are two sides to every coin. Just as important to better listening in a conversation is talking, and asking the right questions when you do talk, in order to further the conversation, can make a big difference in how well a financial advisor connects with their client during a meeting.

Essentially, different questions impact a conversation in different ways. Depending on how a question is used, it can enhance the conversation… or not, as inappropriate or awkward questions can actually halt the rapport building that can come with the right questions.

For instance, research has shown that close-ended questions (i.e., questions that can be answered with a single word, like “good”, “yes”, “no”, “fine”, etc.), in and of themselves, can be stressful because our brains tend to think that there is always a ‘right’ answer. And as such, people feel pressure to provide that ‘right’ answer, be it socially driven or something else.

Example 1: Linda is meeting with her new financial planner, Tina. As the women sit down to meet, Tina says, “Welcome, Linda! How’s it going today?”

Linda gives Tina a sheepish glance and says, “Ya know, okay.”

Unbeknown to Tina, Linda is pretty stressed. In fact, Linda wants to say, “I am here because I am really anxious about my financial situation.” However, Linda knows that is not the ‘right’ response for a first meeting and worries that Tina would just think she is awkward.

Linda can’t tell if Tina is really asking for how she is truly feeling or just giving a greeting. As such, Linda holds it in and provides Tina with a very nondescript response.

Practicing and using lots of open-ended questions (i.e., questions that can not be answered with a single word and that may actually take a bit of thought to answer) is generally a good thing because when we ask these types of questions, our brains aren’t automatically prompted to think that there is a ‘correct’ response it must provide, which can make it more comfortable for the respondent to speak authentically to whatever is on their mind without worrying about whether it’s the ‘right’ answer.

However, if questions aren’t paced correctly (e.g., taking time after every 2-3 questions for reflection), the conversation can feel like an interrogation.

Example 2: Tina, sensing that something is up with Linda, decides to switch tactics. Tina tries to use open-ended questions, but she doesn’t stop to reflect on what might really be bothering Linda. And as a result, Linda becomes more anxious and doesn’t know how to keep up with answering Tina’s questions.

Tina: Tell me about your current financial goals.

Linda: Well, I want to feel less stressed.

Tina: Tell me what you mean by "less stressed"; what does that look like for you?

Linda: I want to be able to sleep better at night.

Tina: Tell me more about that; what do you mean by “sleep better at night”?

Linda: Well, I guess I just feel really anxious. I worry about my future, and some nights I stay up just thinking about it all.

Tina: Tell me more about what you mean by “thinking about it all.” What topics come up?

Linda: Okay, uh…well, sometimes it’s investments, sometimes it’s my kids, sometimes it’s work, sometimes it’s healthcare…

Tina: Describe for me what is happening with investments?

Linda: ….

Tina is trying to help Linda and wants to understand what is going on with her, but without pause or reflection between her questions to do so, Linda might feel attacked or confused by Tina’s quick method of questioning.

So what to do about this? What is the right way to ask questions, and what are the types of questions a financial advisor can use to establish good client rapport during a meeting?

Advisors are likely very familiar with asking open-ended and closed-ended questions, but there are also transformations, swing, implied/projective, and scaling questions. In practice, such questions are commonly taught to therapists, who learn how to use these other types of questions so that they can adeptly build rapport while learning about their patients – and advisors can learn how to use these questions to build rapport with their clients, too!

By growing your question game, you’ll have more opportunities to gather valuable client feedback and to build trust. For instance, open-ended questions, as advisors know, are great for getting to know someone. Yet, using a swing or implied/projective question, which is structurally similar to open-ended questions, can actually help to grow the connection in relationships even after the relationship has been established. And scaling questions (honestly, one of my favorites and I believe under-utilized) are wonderful just about any time for any client or prospect.

Alternatives To ‘Traditional’ Open- Or Closed-Ended Questions To Enhance Client Relationships

Different question types can serve different purposes and may even be reserved for different stages of the financial planning relationship. The trick with effective questions is choosing when to use them and who (and at what stage of the client relationship) you use them with. Understanding how and when to use different question types can serve to elicit deeper responses and ultimately strengthen relationships with clients.

Swing Questions – An Invitation For Deeper Client Responses (But Not With Oppositional Issues)

Swing questions are essentially close-ended questions that use ‘will’, ‘can’, ‘would’, ‘could’, and ‘should’. For example, “Would you be willing to do X?” Or, “Can you tell me a bit more about Y?”

Yet, even though these questions can be answered with a ‘yes’ or ‘no’ response (which technically makes them closed-ended questions), they are actually a bit different from simple closed-ended questions because of the use of the ‘will’ or ‘would’. These words are subtle invitations; using them invites the client to share more if they need or want to and does not imply that there is a right or wrong answer. They are not intended as questions that can be construed as a command or instruction that needs to be followed, but simply and solely as an invitation.

Swing questions are often best suited for clients with whom the advisor already has an established relationship. While using these questions in a newer relationship won’t hurt the relationship, without an underlying relationship the question may fall flat instead of soliciting a deeper response. Advisors might end up with a simple 'yes' or 'no' answer, which is likely not what they were going for in the first place. Or (new) clients may interpret the question as more of an implied directive and then resist it (if only because most of us don’t like being told what to do!).

Example 3: Billie, the financial advisor, has been working with Tina for a couple of years. They have a good working relationship. Tina is coming in today as she has recently been through a divorce, and some changes need to be made to her estate planning documents.

During the meeting, instead of asking, “Have you called the estate planning attorney yet?” Billie decides to use a swing question. Billie doesn’t want to ‘command’ Tina; this is a sensitive time, and they have a good relationship.

Billie feels confident that even if he asks a closed-ended, “Can you tell me a bit more about how it’s going with the estate planning attorney?” Tina will recognize that Billie is truly interested and will likely give a more descriptive answer than just “Fine.”

In the book Communication Essentials for Financial Planners: Strategies and Techniques, Dr. John Grable and Dr. Joseph Goetz (which was the basis for this blog) suggest that individuals be wary of using swing questions if they are running into oppositional issues.

For instance, if an advisor has suggested to their client that they should save an additional $500/month and has brought this issue up a few times with no action from the client, asking a swing question like, “Would you be willing to start saving the monthly $500 we have spoken about?” can sound confrontational or condescending.

The client may perceive the advisor as being somewhat passive-aggressive, given the undercurrent of opposition to saving more… and that won’t leave a good taste in anyone’s mouth.

As such, if disagreeing about an issue with the client in the first place, avoid swing questions that may come across as passive-aggressive or leading… or they might not swing in your favor.

Implied Questions – Another Way Financial Advisors Can Encourage Conversation And Strengthen Client Connections

Implied questions are essentially statements that are structured as indirect questions and use phrases like “I wonder” or “you must”. Like swing questions, implied questions are best used once a relationship has already been established. The established relationship here is important because, without it, these questions can sound a bit odd and possibly disingenuous; if there is no pre-existing rapport, the questions can also be a bit confusing to the client in choosing how to respond.

For instance, an advisor could use an implied question to ask, “I wonder what you will do with this upcoming raise.” instead of asking a direct question, such as “What do you intend to do with this upcoming raise?”

So why use an implied question instead of the more direct alternative?  Basically, it is a softer way to ask the question, and more importantly, has the opportunity to demonstrate a sincere interest from the advisor in what the client thinks.

Again, an implied question is a question designed to probe for deeper nuanced answers and elicit conversation, not an instruction or a direct question aimed to gather data. These are the kind of questions that are meant to create those closer relationship ties. Think of how you talk to a close friend or a partner. You likely wouldn’t say, “Tell me what you think about X.” You would probably be more likely to say something like, “I wonder… what do you think about X.”

Example 4: Frank is Bob’s financial planner. Bob has come in to talk about how things have been going, given all that has gone on with COVID-19.

Bob has just retired and is aware (and really afraid) of what a bad sequence of returns will do to his retirement projection. Moreover, Frank and Bob want to discuss how recent events could impact the portfolio and brainstorm some Plan B strategies.

Thus, after the portfolio discussion itself, Frank says to Bob, “Bob, we just went over a lot of stuff, mostly good, but some tough things, too. And I am wondering… what are you thinking?”

Using implied questions is an invitation to connect, not a command for information.

Projective Questions – Helping Clients Visualize Possibilities

The next two types of questions, projective and scaling questions, are fun and can really be used with anyone at any time. Whereas the two previous question types, swing and implied, were different ways to ask closed-ended questions, projective and scaling can be thought of as different styles of open-ended questions.

Projective questions use phrases like “What if…?” or “What would…?” and the goal is to help clients freely visualize. For example, the Communications Essentials for Financial Planners text offers this projective question for advisors to ask their clients: “If you could go forward in time, what legacy would you like to be remembered for among friends, family, and colleagues?” Then wait for the response. Resist the urge that could end up creating a transformation question (which, as discussed below, is generally not that helpful).

For example, “If you could go forward in time, what legacy would you like to be remembered for among friends, family, and colleagues… would it be that you really, really care about your foundation?” This added piece at the end makes it a closed-ended question and leads the answer – there’s no point in asking an open-ended question if we just close it again in our excitement for the answer!

Moreover, once the client has shared information and a baseline relationship has been established, advisors can follow up on the open-ended projective question with a swing question and get even more information about the client’s thoughts, feelings, values, morals.

Example 5: Jaime, the financial advisor, asks his client Tim, “If you could go forward in time, what legacy would you like to be remembered for among friends, family, and colleagues?” and waits for a response.

Tim takes a second to answer. He is thankful for the question and really wants to give it some thought. Finally, he says, “I would want my friends, family, and colleagues to remember me or see my legacy as one of compassion for others.”

Jaime replies, “Wow, compassion for others, that is incredible.”

Jaime wants more information, but instead of commanding – because it is clear Tim and Jaime are connecting – Jaime asks a swing question: “Can you tell me a bit more about what compassion for others looks like for you?”

And then Jaime leans in, displaying true interest with the invitation to provide more information.

Scaling Questions – Gauging Relative Levels of A Client’s Interests And Concerns

Scaling questions are a series of questions that can be used at any time to solicit a client’s concerns and their willingness or interest in change. For example, an advisor could ask, “On a scale of 1 to 10, 1 being totally sad and 10 being totally happy, where are you on that scale today’?

The toughest part about these questions, though, is actually the follow-up and keeping it positive and non-judgmental, even if the client gives a lower score.

For instance, it is not fun to hear that since your last meeting, your client feels like they are at a 5. Instead of saying, “Oh my…why so low?” the advisor can flip the conversation and respond in a calm, unassuming tone with, “5 – tell me why so high, what’s keeping you from scoring a 4 or lower?”. While advisors do not want this question to come off as though they expected a particular answer, be it high or low; the goal here is simply to focus on the positive, not the negative.

Furthermore, this may seem a bit counterintuitive at first, but it helps keep things positive because it gets the client explaining why they were higher and not lower. For example, if the advisor had asked, “5 – tell me why so low, why not a 6?” it may lead the client to think more about the bad stuff as they recall everything negative they can in order to feel justified about their low number and may prompt the client to think along the lines of, “I’m not a 6 because I haven’t made any progress towards my goal!”

Conversely, if the advisor flips his response to focus on the positive aspect of the client’s answer (at least it wasn’t a 4 or less!), it gives the client an opportunity to respond with something more like, “Well, I am here today, so I feel good about that. But things in my life are just stressful right now.”

Scaling questions can be used to help clients consider positive aspects of their situation, instead of just more negatives.

21 New Questions Financial Advisors Can Implement With Clients And Prospects To Generate More Ideas And To Establish Trust

Essentially, it is one thing to know about the different types of questions, but it is another to actually use these questions to your advantage during client and prospect meetings.

To that end, it may be helpful to think of questions grouped into two larger categories to create some context for when to use them:

1. Questions that solicit information (open); and
2. Questions that build relationships by inviting clients to share versus commanding them (closed).

Questions That Solicit Information

If you want to solicit more information from prospects or clients, use projective and scaling questions. Again, both allow prospects or clients to think more openly or broadly about a situation.

Use these questions any time you want to brainstorm or to create a safe, open environment to share openly and without borders – be it to solve an issue or just to learn about the person sitting in front of you.

Here are six examples of projective questions that could fit into prospect or client meetings:

1. If you could solve any financial concern today simply by snapping your fingers, what would you solve?
2. If you didn’t have financial worries anymore, what would you do, and how would that change the way you act?
3. What would happen if all of your financial goals come true? How would you know when this happened? Paint a picture of this day for me.
4. If you could fast-forward to your ideal retirement, what would we find you doing to fill your days?
5. What would happen if you made changes to your spending and saving patterns? How would you feel?
6. What would success look like for today’s meeting?

Here are examples of scaling questions that can also fit nicely into prospect and client meetings:

1. I know you have been asked to gather and review a lot of financial paperwork lately. Thus, before we get started, I would like to know a bit more about how you are feeling. On a scale of 1 to 10, with 10 being the highest, how financially confident are you feeling?
2. I know the markets have been moving around a lot lately. Thus, before we get started, I would like to know how you have been handling it. On a scale of 1 to 10, with 10 being the highest, how calm do you feel?
3. I know we have been working together now for a little while, and we have covered many financial topics lately. Thus, before we get started today, I would like to know a bit more about how you are feeling about having been through this process. On a scale of 1 to 10, with 10 being the highest, how financially organized are you feeling?
4. We haven’t seen each other since your last review, and a lot has probably happened during that time. Thus, before we dive in, I would like to get a sense of how you are feeling about your current financial track. On a scale of 1 to 10, with 10 being the highest, how on track do you feel?
5. We have covered a lot today in our meeting related to your financial plan. Thus, before we go, I would like to get a sense of how you are feeling. On a scale of 1 to 10, with 10 being the highest, how doable do you feel the plan is?

Scaling questions can be used multiple times too. For example, in a follow-up meeting, an advisor could mention, “Last time, you scored yourself as X” and then ask the same scaling question again to compare and contrast previous and current results.

Again, the toughest part about scaling is perhaps not overreacting when you do not necessarily like the answer. For instance, we might want clients to feel that they are more confident having gone through a financial planning process, but that may not actually reflect reality. Instead, the client might feel a lot of anxiety as they learn to talk about their finances more openly for the first time.

As such, the best practice with following up on a scaling question is to always respond affirmatively. Instead of saying, “Wow, a 5 is low…why so low?” always say, “Wow, 5! That’s great. Why so high?” Alternatively, one could also respond somewhat evenly. For example, “Okay, 5. Tell me more about what went into that score.”

Typically, the point of scaling questions is to use the scale and reflect above or below the score that is given to bring about context and more information. However, it is not necessarily wrong either to simply ask someone how they arrived at their score – but I usually prefer to do that only for the more positive ratings (e.g., 7 and above).

Questions That Build Rapport With (Existing) Clients

If you want to build on established rapport – particularly with existing clients with whom there is already some relationship that could be deepened still – use swing and implied questions.

The trick to these questions is that they should be invitations, not commands, for more information. It is the invitational nature of these questions that tends to show genuine interest in the client without leading the client the way traditional closed-ended questions do.

Five swing question examples are:

1. Will you tell me how your recent estate planning meeting went and how things are going with the paperwork?
2. Could you explain to me a bit more about your education funding ideas or plans for your grandchildren?
3. Can we discuss why the phone call to the company’s benefits coordinator has not been made?
4. Would you tell me a bit about your upcoming schedule? I would like for you to make time to attend an upcoming presentation on taxes.
5. Will you tell me more about your desire to purchase a new home?

Five implied question examples are:

1. I have reviewed your financial documents; I wonder if you could tell me more about how your current financial situation feels?
2. I have reviewed your estate planning documents; I wonder how you would react if family members later fought over this decision?
3. We have discussed many goals today, and I wonder which two are most important to you?
4. We have covered a lot of ground today regarding markets and your long-term portfolio considerations. I wonder if reviewing all of this information has brought to light new questions or ideas?
5. You have expressed some important information today regarding your new employment options. I wonder how you see making this change would impact your retirement goals?

Pitfalls To Avoid – Transformation Questions (Open-Ended Questions Sabotaged By Closed-Ended Questions) And Asking Too Much All At Once

Transformation questions are another type of question that are commonly used but that are not actually very helpful. These are open-ended questions combined with close-ended questions; this combination, though, generally just results in a 'yes' or 'no' close-ended response because of how the listener’s brain tends to process the question structure.

For example, it would not be uncommon to hear an advisor say, “Tell me about your investing experience?” This can be a great open-ended question, yet a lot of advisors then add something like, “Is it fun for you?” or “Has it been scary for you?” or “Has it been confusing for you?”.

It is normal to want to fill in space by asking that secondary question. And maybe because the advisor is so interested, they ask the client two or three more questions in rapid-fire succession. Yes, you are demonstrating interest. But the great open-ended question about the experience is now transformed into a close-ended, “Are investments X for you?” question that actually inhibits a more open discussion of the topic.

What is more (and worse), these transformations can cause the client to feel as though the advisor is leading them to answer in a particular way. With questions like, “Is it fun?” or “Is it scary?” the client might think or feel that saying “yes” or “no” is what the advisor wants to hear, and not necessarily how the client actually feels (remember, our brains tend to think there is a right or wrong answer when close-ended questions are posed).

Advisors can avoid transformations by pausing after asking an open-ended question. Yes, this is easier said than done and will require practice. However, it will help to avoid turning great open-ended questions into transformation questions where only the close-ended part of the question is answered (and maybe not even truthfully).

There are two final considerations to make to ensure that the questions being asked don’t make the client feel like they are being interrogated.

First, regardless of what type of question you are asking, consider that no more than 3 questions should really ever be asked without stopping for a chance to reflect on the conversation. Rapid-fire questions, even when the questions are good, can be exhausting and feel intense.

Reflect on what the client or prospect has just told you, and realize that their brains can use a break after asking important, thought-provoking questions. It can be tempting to ask more questions or to keep asking questions, especially if these new types of questions allow you to get some super-cool information from clients… but don’t get ahead of yourself!

Second, don’t just skip to clarifying questions. Instead, try repeating back to them what they have said – don’t just say, “Thank you for telling me X, you mentioned Y, tell me more about that”. Yes, you have paused and restated that they told you X, but are then essentially diving right back down to the questions. Stop for true reflection every 2 to 3 questions.

Example 6: Let’s return to Linda and her financial advisor, Tina. Previously, Tina had been asking Linda back-to-back open-ended questions without allowing for any space to reflect on what was truly bothering Linda.

Tina is interested in helping Linda and very much cares about how she is feeling. She senses that Linda is becoming more stressed and is not really focused on engaging in the conversation anymore.

In response, Tina decides to add space to the conversation by allowing for some reflection.

Tina: Okay, let’s back up a little bit and revisit your investments later. Let’s go back to how you’re feeling stressed and what you mean by wanting to feel ‘less stressed.’ What does that look like for you?

Linda: Well, as I said, I want to be able to sleep better at night.

Tina: Thank you for sharing that with me, Linda. If I hear you correctly, your financial stress impacts you on a daily or, maybe better said, nightly basis?

Linda: Yes! I just lay awake at night and can’t sleep. A lot of times, I just toss and turn in bed, worrying about money.

Tina: Okay, would you mind describing for me what you mean when you say ‘money’? Money can mean different things for different people, and it can also dig up a lot of different issues.  I want to better understand how you are feeling about this important area.

Linda: Gosh, a lot of stuff comes up! I worry about my investments and how money impacts my kids, my work, and my health.

Tina: I’m so pleased you are sharing this with me because I know that this can be really hard stuff to talk about. Would it be fair to say that an overarching fear of running out of money is part of what is stressing you out and keeping you up at night?

Linda: …

In this conversation, Linda feels a stronger connection to Tina as they have room to explore how she is feeling about the issues that are on her mind.

Tina realizes that she can uncover the exact same information using this approach and that by being mindful of pacing her questions to allow for some reflection, the conversation becomes much less stressed and even helps to create a better rapport with her client.

In this example, it doesn’t really matter if Tina’s overarching assumption is right or wrong because the point is that she is taking the time to question, listen, and reflect. Linda can very easily correct her with her next response if that isn’t the overarching fear.

Moreover, what really matters is that by allowing for some reflection in the conversation, Tina is able to get the same amount of information but in a manner that lets her client feel heard, and that establishes a true connection between them.

This underscores the importance of giving clients a ‘brain break’, showing the client that you are listening, and ensuring that you have heard them correctly. Allowing for some reflection also gives clients an opportunity to relax and catch their breath, and those little breaks help to keep the conversation from feeling like an interrogation.

---

Having a strong question game can be a really fun and interesting way to approach both learning about a client, as well as continuing to build on your relationship with the client.

Communication is something humans do all the time, but that does not necessarily mean we are good at it. Fortunately, though, the reality is that the specialized training that therapists have developed over the years to help them be more effective communicators isn’t specific to just therapists; advisors can absolutely apply the same lessons and hone these skills, too, in order to improve communication with clients!