Meeting prospective clients and asking them important questions can often be a tough task. You have to find the right questions to ask if you want to be sure that the customer’s needs fit your business. Join our host Michelle Weinstein as she discusses this topic with the Sales Whisperer himself, Wes Schaeffer. Wes talks about why you need to ask tough questions to yourself and your prospective client and why being the perfect fit ensures brand loyalty. A must-catch episode for business owners and sales specialists alike.
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The Best Questions To Ask When Meeting Prospective Clients With Wes Schaeffer
We have a very special guest. Our special guest is Wes Schaeffer, also known as The Sales Whisperer. He is an entrepreneur who rehabilitates salespeople and trains their managers too. He is the reassuringly expensive copywriter, sought out after speaker and marketing automation expert. He is also the author of two and a half books on sales, marketing, CRMs. He’s the host of The Sales Podcast. He hosts The CRM Sushi Podcast and will also help you grow by masterminding the overlooked truth in life that makes any sale that you need to make every sale. We’re going to talk a little bit about that.
Before we welcome Wes to the show, you always know that I like to share something with you. I know that a lot of you have a challenge with following up with clients, maybe the ones that aren’t a good fit, and other prospects that you want to work with but maybe it’s not the right time. I’m working on my new Abundant Accountant Sales app. This is an actual sales tool where I’ve made videos, emails and all the things so you can follow up with your clients. To get access to it, make sure to head on over to FiveStepsToAbundance.com. You’ll get my five-step process that accountants typically use to go from waiting around for the busy season to gaining more confidence, but you’ll also get on my email list.

Meeting Prospective Clients: If you’re dealing with a business client, you try to sell them or make a recommendation.
Make sure to hop on over there and sign up. It’s a great and useful tool that you can put into action. I’ll send you a link to the app where it might help you. You’ll get my five-step process on how to go from waiting around to get busy every year, to having consistent cashflow throughout the year. Make sure to check that out. Also, I would be super grateful if you could leave a written review on Apple Podcasts right here. The written reviews do help the show grow and helps spread the words of everything we’re teaching here on the show to other colleagues of yours that might need some of this help. That’s how the Apple Podcasts department works. The written reviews help spread the word. I’d be super grateful if you could leave a written review. Thank you for taking out that 30 seconds to do so. Let’s welcome Wes to the show.
Michelle, thanks for having me.
Thank you so much for being here with us on the show. It is an honor to have you. I always love talking to my fellow sales advocates. Sometimes selling can feel not so good for a lot of people. In my last class with a lot of accountants, it gives them the jitters. We always have to feel like we have to validate or justify our prices when we share them. I know it’s not easy for many. It’s super overwhelming and terrifying. I love being here to help others and bringing people like you on to help them too. Before we get started, can you share with them who you are in just a one-minute intro?
Even though I’ve trademarked the name The Sales Whisperer, the reality is I hate sales as well. I was in the Air Force. I left to jump into sales but I was always looking for the cleaner, more ethical way to do it. I don’t like the traditional hard closes, alternative choice, high-pressure tactics and gimmicks. I’ve never had that approach. Zig Ziglar said it best, “Selling is the transference of a feeling and that feeling is confidence.” If you can help someone feel confident that they have been listened to, that they are understood and you are there to help them, they give you some money for whatever, a product, a service, a consultation. If it improves their life, if they pay you $5,000 and you save them $10,000, $50,000 or help them make an extra million, then you should be paid for helping them. That’s what I try to help everyone do in every industry.
Zig Ziglar said it best, “selling is the transference of a feeling, and that feeling is confidence.” Click To TweetYou fit the mold with everyone who’s reading. I love sales but doing it in the way where you’re transferring the feeling, which is having them feel confident about an area that sometimes you lack in or the service or product and also the confidence piece that comes across when you understand what to do. A lot of the confidence is missing, especially in the area of sales because there’s no process. There’s no game plan. It’s just like, “We’ll meet with a client. I’ll do my best for them to say yes.” That’s not always the best. We’re going to talk about a few things. We’re going to focus on what are some of the best questions to ask when meeting prospective clients.
Sometimes, if you’re super uncomfortable with sales, you want to go right to, “Here’s my price. Here’s my invoice. Here’s what I’m going to do for you.” That’s more like a transaction, a commodity and not a relationship built type of sale. That’s what we’re going to talk about here. We’re going to give you actionable questions that you can use when you’re meeting with prospects to have them open up, to have them get to the part where you’re transferring that feeling of confidence. We’re also going to talk about having some situational awareness, understanding what that is and when I need to maybe stop talking. Maybe I need to listen to what my prospect is saying and not shove things down their throat. That’s what we’re going to talk about.
In every industry, listening is important. When you hear about a bedside manner of a physician, what does that mean? It means that they are listening. They’re diagnosing before they prescribe. Even if you know the answer, the customer needs to feel listened to and understood. I don’t know if there’s one set answer but let’s look at some of the higher-end professions, accounting, financial services, legal or healthcare.
Let’s talk about accounting because that’s who are reading, all the accountants.
All of them, what they have in common is you’re charging good money to provide a service or a result to help the customer get better. It’s like a doctor. What’s the best question they should ask? It’s like, “What’s going on? Why are you here?” You have to ask that in a nice way in all of those situations. You sit down with an attorney, “What’s going on? How can I help?” You go see an accountant, “What’s going on? How can I help?” They have to start talking a little bit and then you say, “It’s interesting. Tell me more. How long has that been a problem? Who besides you is worried about this?” If you’re dealing with a business client and you try to sell them or make a recommendation, “That’s good. I’m going to go get my partner. I’m the CEO but I need the CFO to sign off on it,” or “I’m the CFO. I need the CEO to sign off on it.”
That’s a great question to get another decision-maker there so you don’t waste your time. I talk like I’m an accountant when I’m here because we meet with business and the business owner isn’t there. At the end of the meeting, they’re like, “Thanks so much. I need to go review all this with my partner.” You didn’t even know they had a partner. This is a great way to bring that upfront when you’re first talking to them as maybe the 2nd or 3rd question that you ask. Can you repeat that one more time because the way you phrased it was perfect?

Meeting Prospective Clients: We believe the government should be paid every dime that it’s owed. We just don’t believe in giving them a tip.
You have to be careful with this. I’ll use a very over-the-top example to make a point quickly. I’m looking at vehicles. Let’s say you come on a lot as a woman and I’m the misogynist, chauvinist, old school salesman, “Little lady, where’s the man that’s going to make all the decisions? Clearly, women don’t buy trucks. Who do you trust to make this decision?” You’re like, “I’ve got the money and I’m leaving.” I do need to know, “Thanks for coming to the lot. Is this for you? Is this for someone else? Are you doing some research? Where are you in your truck buying journey?” It’s a nice way of saying, “Do you have someone else? Are you bouncing this off of somebody?” In business, we can’t just say, “Michelle, thanks for coming to Wes’s Accounting Service. Are you the decision-maker?”
We can’t ask like that but I love how you said it like, “Who besides you know about these challenges in your business?” That’s a great subtle way to bring up who else is the most important person that should know about this?
It’s not necessarily the most important person. Smart people surround themselves with smart people. I’m not a dummy but I’m not an accounting expert. We’re doing our taxes. We had the same tax guy for many years. My wife dropped them off. They called my cell phone and they said, “Mr. Schaeffer, your wife was here. We just had a few questions.” I’m like, “She’s running some errands.” They said, “We left her a message.” I said, “You can ask me. I might know.” They asked me three questions. I didn’t know the answer to any of them. I was like, “You got to wait for her to call back.”
Technically, I’m the president of the company. Realistically, my wife knows everything. She knows more about the guts of it. I do the sales. She does all the behind-the-scenes stuff. You have to ask, “Thanks for calling. I’d love to set up a time to have you come in. In the interest of time, would it make sense to have the financial people on your team come in with you so we can get everything out on the table at once and see if there’s a good fit?” “I wish I had a team. It’s just me, myself and I.” I was like, “That’s a good idea. I don’t even want to go to this meeting to tell you the truth. My wife says that we got to do this. Let me check with her and I’ll call you back.” Now you know the relationship. Wes is the face of the company but his wife runs the behind the scenes. A smart accountant is going to wait until we’re both available or maybe just the wife is available. In this case, you’d probably be better off meeting with her because I don’t want to be there.
It’s important to figure that out. One of the biggest complaints I hear from a lot of accountants is, “We’re working 14, 18 hours a day. We get a lot of time wasted by our clients.” This is one way you can take control and ownership of your time and the value of your time. Someone like Wes, they’re removed from the internal part of the business. He’s the face of the business. I always think about this and I’d be curious to know because I do teach accountants. If you both are let’s say 50/50 partners in the business, it’s like when you got married. You both came to sign a marriage document when you married your wife. It’s not like, “I’ll come. We’ll get married but I’m not going to sign that now.”
When it comes to accountants, their clients, the taxes and the books, especially on tax planning engagements and these big things, for your wife to go and then regurgitate everything to you before you’re like, “I’ll sign that. We owe this much,” I feel like even if you’re sitting there and not even saying a word, at least your wife doesn’t have to go and explain it again. That’s what I share with each of you reading. How can we maximize and leverage our time? To go back and forth, call Wes with questions, then the wife knows all the answers, you feel like a ping pong ball getting tossed around.
You got to put your foot down. Eventually, you see experienced people. How do they get more done? It’s because they’re not afraid to ask the hard questions and not proceed until they’re done. It’s like, “I’d like to come in and get my taxes done.” It’s fantastic. “Do you want them done right? Do you want them done on time? Would you like to have seventeen meetings and pay by the hour as we go through this?” “I want them done right.” “I’ve got a three-page checklist. Let me send that to you. There are some detailed items in there. The mandatory things are marked. The optional but recommended things are also marked. Once you get all of the required and most of the recommended, let me know. We’ll schedule a time and have you come in. This way, we can be super-efficient. It will save you some money. It’ll probably going to save you more on your taxes because we’ll get the questions answered. How long do you think it will take you to get that done?”
I’m going to put it back on them. I need them to commit. I know the value of my time. I’ve been there done that. I got the t-shirt. I’m paid by the hour. Let them come in and ramble. That’s okay in theory but you get these flighty people. They’re going to get mad, “I went in to see Michelle. She was smart and all but she could have totally emailed me this thing. She made me come in and charge me for what she could have emailed me. I still have to come back. She’s going to try to take your money. I don’t recommend her.”
That’s all the front-end stuff. Figuring out the process to reduce the back and forth is what I’m hearing you say, Wes. I am 100% aligned with that. What do you feel are some other great questions to ask prospects if we were at Wes’s accounting firm that you think would be unique and different from other accountants that have never asked a prospect like this before to set themselves apart and differentiate themselves from other accountants out there?
This applies to any business. I ask people, “What are your top three non-negotiable criteria when choosing a new fill in the blank, a new accounting firm? What are your top three non-negotiable criteria when choosing a new primary care physician, a financial advisor or a fitness coach?” They’re going to answer 1 of 2 ways. They’re going to rattle those things off, which means they’ve given this some time, some thoughts and consideration as a serious buyer or they’re maybe a flightier person. Not necessarily flighty. I’m not flighty but I don’t give too much thought to my accounting other than I know it needs to be done. I’m going to find the best and I’m going to trust them.
If you asked me, it’s like, “I don’t know. Good word of mouth, good experience, good reputation. They’re aggressive. I don’t want them to cross the line but I want them to go right up on that line and dance on it.” “I’ve been in business for years. I feel the same way. My guy was a former IRS agent. He does pushes it. He doesn’t cross it.” It’s getting them to think, “What are your top three non-negotiable criteria?” The other is a variation of what we talked about, “Thanks for giving us a call. Who on your team do you run things by? Who on your team do you count on for advice, recommendations and second opinions when you are bringing in when you’re considering working with a new accountant, a new financial advisor or any professional that’s going to help you in your business?” “I want to know. I wish I had a team. My wife, for sure, I got to get her in on this meeting. That’s it.” Those are going to get you going down the right path. Depending on how they answer, you can go back and forth a little bit. If it’s a business, there are different questions.
You need to understand that whoever is asking the questions is in control of the conversation, but they can’t feel like it’s an inquisition. There needs to be some give and take. You need to get the tough questions out of the way upfront. A lot of times people delay going overpricing and spring it on people. If you are maybe at the higher end, you want to start getting that out, you don’t want to have a 30-minute or a 60-minute long meeting and then go, “You charge what? I would never pay that.” You need to get the tire kickers out of the way soon.
Smart people surround themselves with smart people. Click To TweetFor everyone reading, they know exactly who the tire kickers are. I have a question. I’m not a big proponent about telling your prices 100% upfront. I’m a boutique firm. We’re not the cheapest on the block talking about some of the differences. Your accountant is aggressive. They have good word of mouth sharing that. I feel like until the relationship is built and you transfer that confidence over to them that you are the best accountant for that client, then it’s okay to show the price.
What would you recommend in a subtle way to ask or even a statement to a prospect to get rid of the tire kickers, the super cheapies that only want a tax return done for a couple of hundred bucks? Everyone reading is trying to get rid of those clients anyway. We’re talking about the higher-value services. I know a lot of accountants who want to sell monthly bookkeeping. We want to sell profit coaching services, CFO services, tax planning and preventative options. Like the doctor, we’re looking for a preventative approach before we end up in surgery. For their clients, those are higher fee services.
That’s the top three, “Michelle, thanks for reaching out. Let me ask you something. What are your top three non-negotiable criteria when choosing a new accountant? Is this for yourself or for your business?” I’m going to let you answer, “Cost is a big thing.” I’ll be like, “Let me stop you right there. We are not the easy form file minimum price, get it done and never see you again. If you’re looking for a low-cost provider, I can give you some recommendations but we’re probably not a good fit.” “I’m not so cheap. I’ll pay for value.” I’m asking that early on.
That’s a great subtle way to incorporate it after asking. The first question is the great one. I’ve never asked anyone this before or shared it with an accountant. This is good. This is gold. I would write this one down and put it on a sticky in front of your computer. What are the top three non-negotiable criteria when you’re looking for a new accounting firm? To get someone to switch accountants is a big task. Are you looking for yourself for your business?
It’s interesting because I also volunteer on the suicide hotline. One of the first questions we ask because the people calling that line are sometimes calling for their kid, for a friend or a significant other is, “Is this for themselves or is this a third-party call?” We asked that even in that situation. For business, that’s super important. If you’re trying to only attract business clients, that’s a great question. It’s a simple, subtle, very cordial question to say, “Is this a service you’re looking for yourself or your business?” Right away you can find out, “I don’t have a business.” “I have some people that work with individuals that I can send you to.” It only took up five minutes instead of 60 minutes.
You can subtly drop in some hints. In my business, I say, “This is fantastic. Are you looking for private coaching? Are you looking for small group training? Are you looking for on-demand services that you can do at your leisure?” I let you know the three different ways I can work with you. Is this for pre-planning or revenue protection?
It’s the different services that you want to offer, not the services that maybe you currently offer that you’re trying to get away from and focusing more on the higher value type of clientele. That’s a great way to say. They might not know what they’re looking for, to be honest. For a lot of the accountants reading, people me like, I don’t know what I need. That’s why I’m coming to you. That’s why I go to the doctor. I don’t know how to fix myself. Everyone reading, they are the surgeons. A lot of successful business owners have no idea what they need. That’s why they come to you. Even personal training, you go hire all these personal trainers and dietitians because they’re experts in their area for that specific need. For the accountants, that’s you. You need to tell us what we need. We don’t know. How would you phrase that question to say instead of, “Are you looking for?” To be honest, I don’t know what I’m looking for. I’m being the typical business owner.
That’s anything. We don’t reach out until we’ve exhausted every effort to find the solution on our own. I’ve tried TurboTax. I’ve tried paying my daughter’s boyfriend who’s an accounting major. I’ve done H&R Block. I got this big tax bill. It’s a total surprise plus there are late fees and penalties.
That goes to the tax resolution people that help you negotiate with the IRS, then fix the problem. I see it as the preventative side. I’m curious to know how you would still phrase that sentence or if we phrase that right. We’re not looking for something, typically. In your case with that scenario, they are because they’ve got this big bill with a lot of interest and a notice from the IRS. That’s always, “Yes, I need help.” That’s a red flag. The business owner getting started, to do it the right way, to take the preventative approach, it’s the 180 difference of what the world of accounting typically has been, which is very reactive.
We’re reacting to people doing it on their own or not getting help from the get-go when they have a business. I’m a huge advocate for that, for all of the business owners that I ever meet. I refer them out to all the readers of the show. It’s so important. If you put your accounting hat on instead to say, “I’m curious. Had you reached out? What you’re looking for? I offer counting services, bookkeeping and the one other high-level thing,” how would you rephrase that to make it a little different so it’s not, “What are you looking for or what do you need,” because they don’t know.

Meeting Prospective Clients: If you’re truly there to serve, then that will come out.
You start at the beginning, “Thanks for reaching out, Michelle. Is this for your business or is this for yourself?” If it’s for your business, “Are you switching providers? Are you transitioning from doing it yourself to having a third-party firm do it?”
We’re doing a role-play, everybody. “I’ve never had an accountant. I don’t know why I would need one.”
“What led to you calling me now?” Something’s happened. That’s the reality.
“I met my friend Michelle and she said I need an accountant. She’s a huge advocate. Even though I don’t have any money and my sales aren’t that high, I plan to do about one million this year but I met my friend Michelle and she said, ‘You better get this done the right way upfront.’ That’s why I’m calling you.”
“Your friend, Michelle sounds like a smart person. On a scale of 1 to 10, how comfortable are you with taxes overall, especially the COVID relief package that was 4,000 pages and was passed in 2020?”
“I’m at about a zero.”
“It’s a good thing that you call. What would you say if you were spitballing this? What are your top three non-negotiable criteria that you’re looking for in an accounting firm to help you meet or even surpass your financial goals this year? Remember, it’s not how much you earn. We can give you some tips on growing the business, but it’s how much you keep. We’re certainly experts in insurance. We believe the government should be paid every dime that it’s owed. We just don’t believe in giving them a tip.”
“I’m looking for in an accounting firm, someone that can digest this to me in fourth-grade rating because it’s all confusing and it makes me numb, all the numbers and all of it. Someone who can help me keep as much money as possible in my pocket because I do not want to tip the government. I’m looking for someone that keeps me in the loop. I’ve heard a lot of stories about accountants that never check in with their clients. That is something that probably won’t work for me.”
“We’ve got an open-door policy. We’re all accessible. Let me ask you something. Do you want us to take this, run with it and keep you updated or do you want to be in on it every step of the way?”
“Even though I am not sure what I’m getting myself into, I do want to be with it every step of the way. I need to learn this. If I’m going to have a couple of million-dollar business, I need to understand the numbers but I never learned this. I’m good at what I do. I need to figure out how I can keep the most amount of money and not tip the government.”
“That’s why you pay us. We’re happy to explain everything that we do. The reality is we’re not going to take any action that you don’t authorize. The laws are changing every year. You go to 100 different accountants. You go buy 50 different pieces of software and you’re going to get 150 different answers on what do you owe.”
That’s the scary part. That’s the terrifying part.
“There is part art and part science to this but as a third-party firm, A) You’re less likely to be audited, B) We have an audit protection service. It’s a little bit more. We charge a little bit for that but it’s insurance. We will defend you, protect you and represent you in case there ever is an audit. We stand behind what we do. The government is big. They can be mean. They have unlimited resources. You’re doing the right thing in setting your ducks in a row before things get too big. Once that genie’s out of the bottle and the IRS has their hooks in you, it’s hard to get them out. We believe a stitch in time saves nine. We’re going to make sure you do everything right ahead of time so they never even notice you. Does that sound like the type of firm you’d like to work with?”
“It does. Thank you so much, accountant Wes.” That was a great role-play. That was beautiful. For everyone reading, you should probably go read that again and write it out. That was perfect. Not tip the government, that was well said. I’ve never heard that for years. That was a great little sentence. Can I steal that? I’m going to add that in for all the tax planners reading in my new sales tool that you are going to get access to. That’s awesome. Wes, I know that your time is very valuable. I want to say thank you for taking out the time to be here with us on the show. This was a great conversation, a great way to lead off every prospect that contacts you to weed out those tire kickers because none of us wants those. Is there anything else that you would want to add that maybe we didn’t chat about yet that popped up in your head?
There’s a four-part motto I was taught in sales and business. It’s that, “Selling is a calling. Serving is its purpose. Questioning is the process and a sale may be the solution.” If you’re the owner of the business, your number one job is to market your business, “Wes, I’m an accountant. My number one job is to do taxes.” I was like, “You can outsource this overseas. You can outsource it to hourly people who can do it 70%, 80% or 90% as well as you can, then you review it and perfect it.” People can learn how to do the taxes decently. You got the magic secret sauce but nobody is going to love your business as you do. It’s your business. You’ve got to market it. The part of marketing is sales. You’ve got to realize, is this your calling? If it is, you know you’re doing what you need to be doing, then you owe it to the community to get the word out. People don’t do business with you for 1 or 2 reasons, either they haven’t heard of you or they have.
As soon as they haven’t heard of you, then are you serving enough people? You serve them by learning how to engage them, how to get their defenses down so you can have an honest conversation. Remember, a sale may be the solution. You may say, “I don’t do what you need. Let me refer you to somebody. You don’t even need us. Here’s a coupon. Go download this software for $50 or whatever and save 50%. Do it yourself. When you get to this level or that level, if you have this problem, come back and see me.” They’re going to look at you in a different light because you didn’t force the issue. Don’t think that sales are something you do to somebody. It’s something you do with them. It’s something you do for them. If you’re truly there to serve, then that will come out and let it come out.
Selling is a calling. Serving is its purpose. Questioning is the process. A sale may be the solution. Click To TweetCan you go through the four things one more time in case someone missed it because it was beautifully said?
Selling is a calling. Serving is its purpose. Questioning is the process. A sale may be the solution.
Thank you so much, Wes, for being here with us on the show. It was an honor to have you. I’m glad to be friends with you. You have great stuff. Where can someone find you if they want to reach out or maybe read something that you wrote?
I’m pretty easy to find at TheSalesWhisperer.com. I’m on all the big social media sites. Contact us form is there with all kinds of free reports and hundreds of sales podcast episodes.
He has lots of great stuff. I highly recommend listening to it and checking Wes’s stuff out. Thank you again for being here with us.
It’s my pleasure.
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Thank you all so much for joining Wes and me here at the show. It’s always a pleasure to be here. I love spending my time with you. I wanted to share though that having your questions ready for when prospects call you and knowing which ones to ask first to get rid of those tire kickers and work with the clients who you truly want to work with, it’s a game-changer. I recommend reading this again, writing it out and putting it in front of your computer. I want to share this. I work at the suicide hotline once a week. I volunteer for about half a day. I don’t come to that shift blind. I have my notes in front of me like I have notes on a sales call. Any time, preparation is key. Chris Voss talked about that in our previous episodes, how preparing for any negotiation is key. You’re in a negotiation 10, 20, 40 times a day. When a client prospect reaches out to you, it is the beginning of a negotiation.
Write out your questions. Be prepared. Be ready for when you get the prospect because you want to have a plan in place. I want to also let you know that I have been working super hard in the background on a sales tool app. It is an incredibly powerful sales tool that every accountant needs to stop winging your sales process, have a simple system in place to position yourself as the expert, convert more high-quality clients to your higher-value services and start having total control over who you work with. If you hate selling or lack confidence, this app is going to be a tool for you. To get notified about it, head on over to FiveStepsToAbundance.com and learn how other accountants have gone from waiting around for clients to getting the confidence to ask for those higher fees. Lastly, I’d be grateful if you’d leave a written review. Thank you so much for being here. I’ll see you in the next episode.
Important Links:
- Wes Schaeffer
- The Sales Podcast
- The CRM Sushi Podcast
- FiveStepsToAbundance.com
- Apple Podcasts – The Abundant Accountant Podcast
- Chris Voss – Previous episode
About Wes Schaeffer
Wes Schaeffer is The Sales Whisperer®, a pigheaded entrepreneur who rehabilitates salespeople and trains their managers. He’s a reassuringly expensive copywriter, sought-after speaker, and marketing automation expert. He is the author of 2.5 books on sales, marketing, and CRMs, host of The Sales Podcast, host of The CRM Sushi Podcast, and he will help you grow by mastering the overlooked truth in life that to make any sale, you must make every sale.
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