Questions That Lead to Sales

July 5, 2022

Click here to download “8 Questions That Lead to Sales” (PDF) or read it below.

Is Sales Like Dating?

About seven years ago, a “Modern Love: column appeared in the Sunday New York Times, “The 36 Questions That Lead to Love.” The article ignited something of a cultural furor. The article proved so popular the New York Times even has its own 36 Questions app. The idea came from a psychological study by Arthur and Elaine Aron that explored whether a series of questions that both participants are encouraged to answer could foster a quicker sense of intimacy and vulnerability that may ultimately lead to love.

The study provided questions broken into three groups. The groups of questions are designed to become increasingly more in-depth than the previous set. Think of it as a relationship fast-forward, if you will. The study itself was published in 1997, but the New York Times article in 2015 ignited a rush to put the questions to the test. This led to earnest relationship-minded men and women sitting down on their dates and digging in deep.

The 36 questions include such inquiries as: “What would constitute a “perfect” day for you?” “What do you value most in a friendship?” and “When did you last cry in front of another person? By yourself?” In many cases, very insightful questions that really would allow you an opportunity to understand your date in ways that would more usually occur over an extended period.

If you google “The 36 Questions” today, you will quickly see they are still popular and used regularly. Even Netflix’s pop culture phenomenon Love is Blind shares elements of the Aron’s original study – compelling people into a situation where conversation is paramount, and self reflection and disclosure are encouraged to accelerate a relationships towards marriage.

I know for some of us, digging in our memory back to the days of dating can be a little daunting but stick with me! Also, I don’t know a single person who can’t recall the excitement, nerves, and panic of getting ready for a first date.

What do first dates and sales calls have in common?

I’ve often wondered if there might not be a correlation between dating and sales. It’s not much of a stretch to liken a first meeting to a first date.

Both can be awkward and uncomfortable. Sometimes one person monopolizes the conversation – spends far too much time talking about themselves or their products and services. Often both parties are left wondering will there be another meeting, which is undoubtedly better than one party anxiously awaiting the end of the date!

Are there questions to ask that help you and your prospect get to know each other better, or determine if this is a business relationship that will work for both parties? The key is the open ended, deep questions. Most advisors ask surface questions and then start presenting how they can help. I believe there are several key questions, and the best aspect of these questions is that they aren’t industry-specific. So here are my go-to, eight questions. I’ve found these work very well. I encourage you to use them, build upon them, and then stick with those that work for you.

I’m sure you’ve all heard the saying, “Selling is not telling.” Telling someone all about your product or service is very rarely going to light up their “BUY NOW” switch. Yet, understanding their needs, goals and objectives, and how you might be able to meet those needs, hit KPIs, and ultimately increase those profits can get you a whole lot closer to a sale. At the end of the day, most people do not buy because of some data point, goal, or want. They buy because there is an emotional connection to your sales approach and what that connection brings out in them. My approach has always been that the best in the business, in any business, get prospects to act when otherwise, they would not.

Again, this isn’t unlike a date – does anyone really want to spend time with someone who only talks about themselves the entire date? No way! You are usually much closer to a second date if you invest in understanding more about your date. How is sales any different?

When someone says, “I love music,” would you leave it at that? Or would you follow up with “Who is your favorite band?” or “What was the best concert you’ve ever seen?” I know that I’d certainly have a lot more information about my date if they shared a lifelong love of Barry Manilow or never missed The Rolling Stones when they come to town.

General Questions to Gather More Information & Understand Your Prospect Better

Much like a first date, a first meeting with a prospect should be an opportunity to get to know each other better. That means you must be prepared to listen and ask good questions to help you understand your prospect’s needs, likes, and dislikes. Here are two questions to get you started.

1. Tell Me More.

This question works for so many situations. You can learn everything from someone sharing the business history to sharing their retirement plan or end game. Maybe they are talking about the team they’ve assembled or the type of employee they want to recruit. This question is excellent because you show sincere interest in learning more about a topic they’ve already begun to discuss.

It can also be used to clarify something. For example, a prospective client shares an unmet need that seems a bit nebulous, and you aren’t confident precisely what the condition is or how they see it being met. You can ask them to tell you more or say, “what do you mean by that?” which is another excellent question for building clarity. It’s also important to note if they can’t answer the question, it can mean many things, including that they haven’t thought it through, or perhaps they aren’t close enough to the issue – they just know something isn’t working correctly.

2. Can you share an example of when that has happened?

How often can you recall a sales meeting where someone shares a preferred way of doing business, or even better, a pet peeve? This is a remarkably insightful question to gather more information about how they prefer to do business.

For example, in our space of helping advisors grow through appointment setting, advisors will often make comments like, “We have tried different types of marketing over the years.” “We rarely have years that we achieved many new prospect meetings.” “I have tried appointment setting, and the quality was poor.”

Your questions can quickly adapt based on what you address with the prospect. “Can you share an example of that happening?” provides detailed information about a previous experience. “Can you share an example of what you mean by poor quality?” will deliver insight into the prospect’s expectations. “Can you share an example of one of the years when you did have a large number of new prospects?” pinpoints the volume of new prospect calls they’d consider successful in the year. “What did you do differently that year?” gives you an understanding of your prospect’s process.

This idea of adapting the question while keeping the overall intent to learn more can apply across the board.

Questions about Problems

Indeed, talking about past relationships on a first date is generally not an intelligent approach. Fortunately, this is where business meetings and dating diverge. Problems and, more importantly, problem-solving is a critical piece of doing business. However, remember that you are not solving problems on the first appointment; you are learning and beginning to drive a wedge between you and the incumbent provider.

Asking questions that get to the heart of a client’s current business woes or challenges can be very rewarding when it comes to the information shared. This can tell you what is working well and what is not working, and where your opportunities are to be the prospect’s solution.

Solving pain points is one of the most significant motivating factors for someone to consider changing a vendor. It’s been said many times before that sales is all about solving problems and that people don’t buy products and services, they buy solutions. This means when you know about a potential client’s problems, you have an opportunity to help solve them. Keep in mind that a problem is not always a concern or fear. Problems can also be about missed opportunities or a lack of awareness. Occasionally, clients simply believe they can be doing “better” but cannot determine how to make “better” happen.

A friend recently told me that her ex-husband hated dealing with repair people of any kind – home, car, anything else. It made her crazy that these time-consuming tasks always fell in her lap. A few years after her divorce, she began dating a new guy. One day, she mentioned that she needed new tires, and he said, “oh, I’ve got a great tire shop, I’ll call them, and we can run your car down there on Saturday – you’ll have new tires in an hour.” He solved something she had identified as a pain point, and they’ve been very happy together for seven years.

Imagine if you could gain that kind of insight into a potential client. When it comes time for your sales pitch, you have a lot more to talk about than just your product’s benefits and features. You have information about how your product or services can successfully integrate into their business model and solve that nagging problem.

Here are a few questions that begin to illustrate the prospect’s pain points when a problem is identified.

3. What have you done so far to attempt to fix the problem?

Your prospect shares a problem. It’s natural to try to understand the cause of the problem and how they may have worked to solve the problem. This can give you an idea of their appetite for change, growth, or bringing on new solutions to problem-solving, among many other pieces of info.

I recently had a conversation with a prospect and made an assumption around the problem they shared. I didn’t explore the issue more deeply and later learned one of my suggestions had already been tried, and the prospect was adamant they would not try that approach again. I got lazy in my process, and it hurt me. It happens. However, the more we practice open-ended questioning and are consistent in our client meetings, the better our approach becomes.

4. What has held you back from solving that problem or changing your approach?

The follow-up question is one that, when perceptive, can also provide a lot of information about your potential client. Is it a lack of resources (time, money, staff) preventing them from solving the problem? Maybe it’s a lack of know-how or fear of innovating.

When it comes to engaging prospects, developing proposals, and establishing a working relationship, their answers can help you solve their problems in two key sales mannerisms. First, speed – how much and how quickly can they assimilate change? At the wrong pace, you risk blowback. Second is tone – is the prospect more formal or casual in their approach to change?

5. Tell me about your relationship with your current provider. If there were one thing you wish the current provider would do better or differently, what would that be?

This is an essential question, and it can help you determine if this is the right sale for you. What if the prospect’s frustration comes from the service provided and your company services their clients in the exact same way? That’s not going to be a great fit and acting in any other way is not only disingenuous but will eventually lead to a client telling the next salesperson in the door what frustrates them about you!

However, their current provider may have a very different approach than the one you utilize, and your process and service would make the prospect’s business more efficient. Now you have a piece of information to build a solid proposal that continues to drive a wedge.

Questions about Opportunities

Once you have a basic understanding of pain points, guiding the conversation to opportunities can be an intelligent pivot and positive turn in the conversation. Moving the conversation to a positive place of opportunity adjusts the tone of the discussion and provides cause for the next meeting. In addition, the prospect may now be curious, and curiosity leads to engagement.

6. What opportunities do you feel you’ve missed out on over the last five years?

There are very few people alive who don’t have regrets and disappointments over things they feel like they missed. Like dating, everyone has “the one that got away.” What is your client’s opportunity that got away?

Their answer to this question can be very insightful. The answer can highlight what your client values most: a potential employee who took another job, an investment opportunity they deemed too risky – but paid off big (for everyone else), or maybe they were in pursuit of a great sale but didn’t land that piece of business.

Thinking again towards solutions, do you offer anything that might have changed the client’s regrets? Better yet, will your solutions put them in an improved position to address a similar situation in the future? Can you get them to act and move forward when others could not?

7. Tell me how you use your employee benefits to help recruit and retain talent?

This is the one question that, for now, I am going to get a little industry-specific. However, it is as easy as turning on the news to understand that most industries face a hiring problem.
An advisor in our space can position this question as an opportunity to understand how health benefits and qualified plans are used in employee attraction and retention. For example, if your prospect is mainly seeking to hire younger employees, maybe they would benefit from having a student loan matching provision on the 401k.

This is also an area of opportunity for savvy salespeople to start a conversation about how your products and services may help to solve this employment scenario. It may even be an opportunity to engage another partner who has relevant resources that could help your prospect move the needle. Making a referral can be a very smart sales technique. It gives your prospect the opportunity to see you in a different light, to view you as a trusted business consultant.

A Question to Close the Meeting

After a productive meeting, you are eager for the next one, and hopefully, your questioning has led to a depth where the prospect is curious and looking for more engagement. Remember, for most of us, this is not a one-call close. Therefore, the purpose of the first meeting is to get to the second meeting with great expectations and armed with some good knowledge of your prospect. Slow it down and have an approach to exiting meeting one with the date, time, and place for meeting two. 

Are you telling your date that you love them after the first date? (think Raj Koothrappali on Big Bang Theory?) Heck, no, you will almost definitely scare that person off. Bluntly asking for the sale isn’t that different (and believe me, I remember that this was the approach for those of us trained 20+ years ago!). However, you end up ruining the mood and immediately become the salesperson again, quickly extinguishing the trust and confidence you’ve been working to build. Wouldn’t it be better to ask a more intuitive, less aggressive question?

8. Based on our conversation, what do you see happening next?

This question is perfect for closing out a productive first conversation. If things have gone well and you’ve asked good questions, listened, been empathetic to their problems, it would seem natural that the next step would be an opportunity for you to share more about your solutions.

After a great first date, it would be natural to ask someone, “would you like to go out again?” Maybe after your first sales meeting, your next step is to ask for a second conversation. Sometimes a first date has great conversation but isn’t the right fit. That might be the case with business, too. It may have been made clear that you and the prospect are not a great fit. Maybe it’s not a good match now, but it could be in the future. Asking an open-ended question leaves you and the prospect the opportunity for honesty and to explore possibilities or to close the door for now.

Putting the Questions into Action

Now you’ve got the questions – what do you do?

Hopefully, sales isn’t quite as tricky as finding the love of your life. When it comes down to it, no one really knows just how successful the 36 Questions are in developing long-term relationships. However, according to a comment on a 36 Questions Reddit thread:

“Before the date, she said, ‘We probably don’t have all that much in common, but I’ll meet up anyway.’ After the date, her position had moved to the opposite, that we might even have too much in common. I think that the exercise made for a very satisfying experience, and so far, the two times that I’ve tried this have made for WAY better dates than any others I’ve been on this year.”

What if employing your version of 8 open-ended sales questions produced similar results? Imagine if you left the meeting and your prospect’s response was something like the following:

“I really didn’t think I was in the market for a new advisor. However, our meeting was excellent. They asked insightful questions that made me think about how we are doing business currently and how we could improve. I don’t know whether we will work together, but I’m enthusiastic about continuing our conversation and learning more about their services.”

I also know that if someone described my first meeting as “a more satisfying experience than the other sales calls I’ve had this year,” I’d be over the moon and feeling pretty confident that asking for a second meeting was the right move.

Advice about using open-ended questions:

• The first thing about these sales questions – these are my eight. But there are many good, open-ended questions that can stimulate conversation and help you understand your prospect better. That is the environment you are trying to achieve. Try your own open-ended questions.

• Start now – you don’t need to memorize and employ all eight of these questions for your next meeting. What if you commit to trying just one? “Tell me more” is a straightforward, natural place to start. Give it a go at your next meeting and see what it may help you discover.

• Get comfortable with being uncomfortable. If you aren’t used to employing a technique like this, it may not feel second nature to you, especially right off the bat. But keep at it, like anything worth doing; it becomes easier the more you employ the method.

• Excellent open-ended questions and probing conversations should help your prospect begin to evaluate what is going on in their world and hopefully start to look at their world a bit differently.

So just like first dates, some of your prospect meetings will be fantastic, and some will be mediocre. But hopefully, by setting the right tone at the first meeting, you are setting the stage for a second one.

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