How Do You Sell an Expensive Service Without Sounding Salesy?

0:00Hello, this is Mark Satterfield and welcome to the Velvet Rope Playbook. Tonight's chapter, how do you sell an expensive service without sounding salesy? Please stop trying to close me. That's not something you particularly want to hear from a prospective client when the engagement you're discussing is worth$125 ,000. But that's exactly what Rebecca Sloan hears on a Thursday afternoon in Palm Beach. Rebecca is 49 and runs a boutique executive search firm specializing in senior leadership positions for family-owned businesses. She's been doing it for almost 20 years. She's smart, accomplished, and very good at finding CEOs, CFOs, and senior executives who can walk into complicated organizations and actually make them better.

0:50And Rebecca isn't naturally pushing, Actually, quite the opposite. But this particular prospect matters. His name is Thomas Carla. Thomas is 64. His grandfather started a commercial building product in Ohio in 1958. Thomas's father expanded it through the Midwest, and Thomas eventually turns it into a business doing several hundred million dollars a year. He has a home outside of Columbus, another in Palm Beach, three adult children, and a problem that's quietly keeping him awake at night. He needs a new president. And not simply someone with an impressive resume. Thomas needs someone who can eventually run the company without destroying the culture that his family has spent nearly 70 years creating.

1:37Rebecca's fee for the search is$125 ,000. They've had two very good conversations, and now Rebecca is trying to get Thomas to make a decision. She explains her process again. She reminds him that she only accepts a limited number of searches. She tells him the sooner they begin, the sooner she can start approaching candidates. Then she says something she learned years earlier in a sales training program. Thomas, is there anything preventing us from moving forward today? There's a pause. Then Thomas says, Rebecca, please stop trying to close me. Ouch. especially because Rebecca isn't trying to be salesy.

2:19She's simply trying to get the business and that's where selling expensive services gets interesting. The more expensive the service, the less people want to feel sold. Look, if you're selling a$29 product online, you can use all sorts of traditional sales techniques. Buy before midnight, only three left, special price ends Friday. But when someone is considering giving you$25 ,000,$50 ,000, or$100 ,000, or even sometimes considerably more, something changes. They're not simply buying your service. They're making a decision about you. Do I trust this person? Do they really understand my situation?

3:03Are they as good as they appear to be? Will I regret this? And perhaps most importantly, am I making this decision because I believe it's the right thing to do or because this person is maneuvering me towards it? Affluent prospects tend to be particularly sensitive to that last question. Think about the world many of them live in. People want their money. People want their business. People want introductions. People want them to invest. People want them to donate. So many become pretty good at recognizing the machinery of selling. And once they see the machinery, resistance goes up. Which leads to what I think is one of the most useful principles when you're selling an expensive service.

3:47Your job isn't to push the prospect toward a yes. Your job is to help them make a good decision. Now, those may sound like the same thing, but they're really not. Rebecca is understandably embarrassed by Thomas' comment, but fortunately she doesn't defend herself. Instead, she says, fair enough. Let me ask you a different question. What are you still trying to figure out? Thomas thinks about that for a moment, and then he tells her. He's not worried about the$125 ,000. He's worried about hiring an outsider. The last president has been with the company for 22 years. The next person may eventually become the public face of a business Thomas' family has spent three generations building.

4:33What if Rebecca finds someone who looks perfect on paper but doesn't understand the culture? Suddenly, Rebecca knows what's really holding up the decision, and it isn't the price. It isn't her credentials. It isn't even her process. It's risk. So Rebecca stops trying to sell Thomas and starts helping him think through the risk. She explains how she evaluates executives moving into family-owned businesses. She tells him why she spends time with other members of the leadership team before beginning the search. And then she tells him about a search she conducted two years earlier. There were three finalists.

5:12One had everything the client thought they wanted. Perfect resume, right industry, impressive track record. And Rebecca recommended they not hire him. and the client was surprised. But during the interview process, Rebecca noticed several small things that bothered her. The candidate repeatedly talked about what he had accomplished. He rarely credited his previous team and whenever Rebecca asked about adapting to the culture of a family owned company, he immediately started talking about what he would change. Rebecca's client hired another candidate. Six months later, the first candidate joined one of their competitors and lasted less than a year.

5:55Now Thomas is hearing something completely different. Rebecca isn't telling him how wonderful her search firm is. She's showing him how she thinks. And that's what Thomas really needs to buy. Not executive search, Rebecca's judgment. And there are three very practical lessons here that you can use the next time you're selling an expensive service. Practical idea number one, find out what they're still trying to figure out. When a prospect seems interested but isn't moving forward, our natural tendency is to start explaining. We explain our service again. We remind them about the benefits. We provide another testimonial.

6:37We defend the price. we ask what we can do to earn their business. But you're frequently answering questions a prospect isn't asking, so try something simpler. What are you still trying to figure out before you'd feel comfortable making a decision? Or what would you need to know to decide whether this makes sense for you? I like those questions because they don't assume the answer should be

7:04Rebecca Sloan:yes. You're not cornering anyone. You're trying to discover the unresolved issue. And with expensive services, that issue can be very different from what you think it is. Maybe it's risk. Maybe it's timing. Maybe they're wondering whether they'll actually use what you're providing. Maybe they need to involve a spouse or a business partner. Maybe they're comparing you to another alternative. Or perhaps they're wondering whether doing nothing is safer than doing something. Rebecca assumes Thomas needs another reason to hire her. He doesn't. He needs to know she won't put the wrong person in charge of his family's company.

7:44Rebecca Sloan:And that's a very different conversation. Practical idea number two. Stop explaining what you do and demonstrate how you think. This is particularly important if what you're selling is expertise. Almost every professional can describe their services. A wealth advisor can describe financial planning. An architect can explain the design process. A consultant can explain their methodology. A luxury real estate professional can describe how they'll market a property. But your affluent prospect is trying to answer a much harder question. How good is this person at what they do? And saying you're experienced, highly qualified, and committed to excellence doesn't answer it.

8:29Rebecca Sloan:Rebecca could tell Thomas, we're extremely careful about cultural fit, but so can every other executive recruiter he's talking to. Instead, she shows him how she evaluates cultural fit. She tells him what she notices. She explains why she's willing to reject the candidate with the best resume. That expertise made visible. And here's an exercise that you can actually do today. So write down three things you notice about your work that someone would considerably less experience might miss. Maybe it's something you noticed during the first conversation with a client, something that immediately makes you suspicious of an otherwise attractive opportunity, something clients frequently think is important that you know really isn't, or something that looks insignificant but experience has taught you can become an expensive problem later on.

9:20Rebecca Sloan:Those observations are marketing gold. Use them in conversations, put them in emails, make them into reels. Write about them on your website. Don't keep telling people I'm an expert. Give them enough evidence to conclude it themselves. That's considerably more persuasive. Practical idea number three. Don't manufacture urgency. Find the urgency that's already there. This is where expensive services often sound salesy very quickly. My calendar is filling up. I can only hold the spot until Friday. If you want to get started, we really need to make a decision today. Well, look, sometimes those things are genuinely true, but if they aren't, your prospect can often feel it.

10:04Rebecca Sloan:Thomas doesn't need Rebecca to manufacture urgency. He already has it. His president is leaving in six months. So Rebecca can ask, what happens if you don't have the right person in place when he leaves? Now Thomas starts thinking about the actual consequences. Who runs the company? What happens to the leadership team? How long will a proper search take? How much transition time will the new president need? Could waiting another three months turn a manageable succession into a crisis? That's real urgency. And real urgency is considerably more persuasive than manufactured urgency. So the next time you're tempted to tell a prospect why they need to act now, try asking, what happens if this problem still isn't solved six months from now?

10:51Rebecca Sloan:Then listen. They may give themselves a much better reason for moving forward than anything you could have invented. So, what happens with Thomas? After about 20 minutes after Thomas tells Rebecca to stop trying to close him, their conversation ends. Rebecca doesn't ask for the business again. She doesn't say, so are you ready to move forward? She doesn't ask, what would it take to get this done today? She simply tells him she'll send over a couple of things they discuss and lets him think. The following morning, Thomas calls her. He has one additional question. They talk for about 10 minutes, and then Thomas says, send me whatever we need to sign to get started.

11:33Rebecca Sloan:Rebecca gets the $125 ,000 engagement, but here's the interesting part. She doesn't get it because she finally discovers the perfect closing technique. She gets it when she stops trying to close him. She uncovers what's really preventing him from making a decision. She demonstrates how she thinks rather than repeatedly explaining what she does. And she helps him recognize the urgency that already exists rather than manufacturing some of her own. That's what selling an expensive service should feel like. Not, how can I convince this person to hire me, but what does this person need to understand in order to make a confident decision?

12:16Rebecca Sloan:Answer that question well enough and something rather pleasant happens. You can sell a very expensive service without sounding very much like a salesperson at all. So if you found this useful, I'd encourage you to describe to whales not minnows that's my private intelligence briefing for professionals who want to attract more affluent clients and there's a couple reasons you might find it valuable first i go considerably deeper into how affluent prospects think and make decisions understanding that psychology can change how you position yourself communicate your value handle price generate referrals and ultimately attract better clients.

12:58Rebecca Sloan:Second, it's designed to give you practical ideas you can actually use without turning marketing into your second full-time job. Twice a month, you get specific strategies, examples, and ideas you can adapt to your own business. You can learn more about Whales Not Minnows and all my other programs by visiting getwealthyclients.com. Because if you're trying to attract more affluent clients, you probably don't need another 27 things you're supposed to be doing. You need a few better ideas about the people you're trying to attract. So go visit getwealthyclients.com. This is Mark Satterfield. Thanks for listening to this chapter of the Velvet Rope Playbook.

13:40Rebecca Sloan:I'll be back at you soon with something new, but until then, bye for now.