Home Service Business Sales Training Session Digest

Kyle Bailey opens by saying the single most important sales skill he wants them to take away is the habit of doing a self-audit after calls, especially tough ones.

He shares his own trigger points on appointments: feeling disrespected, getting nonsensical pushback, or being challenged by someone who clearly knows more but didn’t reveal that up front (e.g., “Didn’t you read the latest Google SEO report?”), which can make his voice shake.

He explains that after an appointment like that, you should pull over for five minutes (e.g., in a parking lot) and quietly ask yourself: “What came up for me?”—instead of just rushing off to the next thing.

Kyle notes this self-audit habit is new even for him, something he created as a mental framework only in the last 12 months, and it’s equally powerful in personal relationships as in sales.

In relationship conflict, as well as home service sales appointments, instead of saying “When you do this, it makes me feel…” or “I feel X when you say Y,” he suggests reframing to:

• “I’m noticing that when I experience you yelling at me, some insecurity is coming up for me.”

• “Some anger is coming up for me—I’m curious about that.”

• Of course, you can’t go through this exercise in person with a customer, so you go through this as a self-audit

He emphasizes actually saying the phrase “I’m curious…”, because there’s a “fundamental fact”: you cannot be curious and angry at the same time; the brain can’t run both modes simultaneously.

Applied to sales, if a customer is blustery or pushing hard, you respond with curiosity instead of reaction:

• (pause, use slow cadence. You’re not challenging, you’re inviting them to polite discourse) “I’m curious—when you say that word, what do you mean by that?”

This curiosity response differentiates you from almost everyone else they talk to, because most people do not have this skill; that’s why people like Chris Voss are so popular—he teaches these rare emotional skills.

Kyle recommends that after every sales call you take five minutes and mentally walk through:

• “I noticed I got frustrated when they wouldn’t listen.”

• “I noticed I got frustrated when they kept interrupting.”

• Then ask, “What’s that about? I’m curious about that. Why did that come up for me?”

He explains that when you do that, you activate your subconscious to start working on the problem; when you instead say, “That customer made me mad, I hate when people do that,” that’s a statement of fact, and you freeze it into a “cyst” in your brain and give your mind nothing to work on.

He ties this to money: “The money is where the emotion is.” Pricing, collections, and payment conversations are heavily emotional for everyone in the room.

On collections, he observes more resistance in the group’s body language than on anything else they’ve discussed, because:

• One side of you knows the money pays for your tires, truck, TV, and family needs.

• The other side feels discomfort asking for money, even though you’ve earned it.

He suggests doing the same curiosity routine about money resistance:

• “I noticed some resistance/fear/pushback came up for me when we talked about closing the sale. I’m curious about that.”

• Even just that will make life a lot better over time.

Kyle shares that he’s been “in the game” for 30 years and just turned 55, joking about how strange it feels to have that much adult experience.

Shifting to pricing, he asks the group how they feel about his concept of “shadowing high” (setting a higher initial ballpark than what you think it might actually be), and invites any negative feedback about it.

One rep explains his approach: when customers ask for a ballpark, he intentionally aims higher than his estimate, because he’d rather start high than quote low and later come in higher—he’s comfortable with that.

Kyle checks that everyone feels okay with this, and they do; then another team member describes a recent job with a prospect named Reggie, a big, sales-experienced guy who answered the door with noticeable tension and coldness.

At Reggie’s house, there was palpable tension initially; he wasn’t thrilled with the situation or the extra person being there, but Kyle broke the ice by commenting on Stax and Motown records on his bookshelf, which led to a relaxed conversation and broke down barriers.

The rep describes the new experience of saying, “Is it okay if I go out and crunch some numbers in the truck?” Reggie, the homeowner, being in sales, knew what was happening but didn’t mind. When the rep returned with two clear options, it felt like a completely different, more professional proposal than the typical bids they’d done.

The rep notes he used to have a hard rule never to ballpark, always saying, “I don’t want to build you up or knock you down. I’ll get it to you this afternoon,” but this new approach changed his perspective; primarily, because it allows you to close the sale same-day.

Kyle then labels the team as “character-based, consultative sellers” who are driven by integrity, delivering value, and being consumer-first; they absolutely refuse to shortchange a customer.

He jokes with one rep (“other than Sam”) who inadvertently set himself up as a target earlier, illustrating that everyone in the room has this integrity trait except the one who teased himself.

Kyle’s diagnosis: the team sets up “straw men” in their own minds—internal scenarios where they believe, “If I do X, I’ll compromise my virtue as a consumer-first seller.” This fear stops them from trying new, effective tactics.

He points out that if the customer isn’t actually giving that negative feedback and it’s just an internal fear, then at least half the time they’re provably wrong, because they’re operating from imagined outcomes, not real customer reactions.

His recommendation: as long as you’re not lying or cheating customers, you should widen your willingness to experiment with behaviors like stepping out to the vehicle to calculate pricing, presenting multiple options, and shadowing high.

When discomfort arises—like feeling weird about leaving the table to go to the truck—you apply the same inner script:

• “I notice some resistance to X. I’m curious why that’s coming up for me.”

The rep reflects on Reggie’s case: during the “reveal” of pricing and systems, Reggie was leaning forward, doing calculations in his chair, comparing different pier systems and proposals (his vs. the competition).

The rep felt clearly that Reggie appreciated having someone there to walk through the numbers and compare proposals; together they concluded Reggie needed a third bid to verify neither this company nor the other one was lying, which is part of building trust.

Kyle notes there are specific moments in each of their past sales calls that the reps could have leveraged but didn’t; they might have noticed them but didn’t act on them.

He recalls that early in the Reggie interaction, the customer’s resistance made him think: either Reggie doesn’t like people, they interrupted something important, or he’d had a bad experience with another company—which turned out to be true.

Another rep shares a useful “straw man” question they used:

• “If you’re a smart homeowner like most of my customers, you’ve probably had at least two other people out before us.” (Then pause.)
  This invites the homeowner to share what’s already happened.

Reggie responded with, “That’s why you’re here,” in a loaded tone, signaling he’s double-checking because he’d been burned before and feels taken advantage of.

Kyle says that’s the moment to answer the emotion being sent, not just the statement:

• “Oh, really? Sounds like you’ve had a rough go of this.”
  Then you unpack the “delivery bag”—his metaphor for the emotional package they hand you.

He uses the metaphor of a hot pizza delivery bag: customers hand you this warm emotional package; most reps just say, “Oh, that’s nice,” and set it aside, instead of opening it up and exploring what’s inside by asking, “Tell me more about that.”

He reminds them of a magician client they met: the man was extremely enthusiastic about magic, knew world-class magician Ricky Jay, had a website (bradshepard.com), lots of custom card decks, and a house full of unusual items (a 6’5″ stuffed grizzly, fake dead babies, taxidermy cat “Brad the cat,” etc.). Once Kyle mentioned magic, the client lit up and couldn’t stop talking—an example of how people pour out when you hit their emotional interest. This gives you, the home service sales rep, an emotional connection point-Rapport Building- as a touch point any time in the sales call.

They discuss whether that Reggie job actually closed—at that moment it hadn’t; a message was left and they were still following up, and Kyle says it’ll be interesting to see what happens.

Another participant underlines Kyle’s point: “address the emotion, don’t veer away from it.” People are emotional; trust is an emotion, not a data point, while price is just a data point.

He notes that, on a shadow appointment where Kyle ran the appointment, Kyle helped guard the prospect’s trust by walking the homeowner through the home and explaining each step of the process like an expert; that rapport is what made trust possible.

A team member who answers phones shares a story: a caller just wanted an estimate for a shifting house and sounded stressed. She asked, “Do you mind telling me what happened?” and the customer emotionally dumped the whole story, which she listened to patiently. ALL PEOPLE ARE ALIKE IN THIS: WE ALL WANT TO BE HEARD AND SEEN.

Even after she said they were two weeks out, the caller didn’t care; he just wanted to be scheduled because he felt heard and appreciated. He thanked her for listening and for tips like checking whether insurance might cover it.

She explains this is typical: on the phone she often gets people’s whole life stories in minutes because they need to talk through their emotions; she doesn’t mind listening, and it creates strong engagement.

Kyle and the others highlight that these emotional “dumps” aren’t a nuisance—they’re valuable for both connection (Rapport Building) and intel (Investigation). When you say things like, “Wow, yeah, it seems like… / feels like…,” they will tell you more information that helps you serve them and sell more accurately.

Sometimes customers may not give exact numbers (“It was $200k” vs. “$50k”), but their tone and frustration can clue you into the magnitude, and if they feel understood, they might even volunteer their previous quote and ask you to review it.

That’s when you know you’ve achieved real trust: they hand you their previous quote and say they don’t feel they were treated fairly—prime conditions for you to close the deal ethically.

Kyle circles back to the “that’s why you’re here” line from Reggie: when said with frustration, it’s an invitation to explore what went wrong before, not something to gloss over.

They discuss another homeowner (a woman) who’d “remodeled her entire home” and was emotionally exhausted and eager to move fast. When she said, “We gotta do something,” that was an emotional flag to ask:

• “Tell me about that. Sounds like you want to move faster on this, or am I wrong?”

Kyle encourages using soft, correctable labels like “Am I wrong?” or “Am I way off track?” This gives customers a chance to correct you, which gets them talking even more and reveals deeper feelings and priorities.

He compares the process to rolling a stone downhill: once you get them talking, they usually don’t want to stop, because most salespeople don’t actually listen.

Kyle shares an example of a bad “super casual” phone script he received:

• “Hey Zach, how’s it going? This is Kyle over here…”
  The caller never gave any real information or objective, so the script felt empty and pointless.

He says if you merely adopt a technique (like a casual opener) without a clear target (value, emotion, purpose), it won’t work—and people will wrongly conclude, “Yeah, Kyle’s stuff doesn’t work,” when in fact the sales rep simply wasn’t using it correctly.

He reiterates: you must be “always communicating value,” and he hints that they’re about to shift into a detailed discussion on value next, but wants to close out the emotion segment properly first.

He reminds them that when they’re in a homeowner’s house, they’re dealing with one of the person’s most precious possessions, which amplifies emotions. Even tough, sales-savvy customers like Reggie have deep emotional involvement in protecting their homes.

Another rep recalls asking Reggie, “Do you have any elevations of where the house was so I can compare an A to B?” That question surfaced that Reggie had recent previous assessments, which is a great way to discover prior visits and why they’re now in the situation they’re in. Find indirect ways to reference previous visits with your competition

Kyle notes that asking about prior elevations not only reveals how many other companies have been out, but also tells you where the customer is in their buying journey and how much explanation they’ll need in the presentation.

The rep observes that everything changed when they sat down and got to “the rat killing” (the hard, decisive part of the deal): that’s when the prospect learns whether they must spend a lot of money to keep the house intact.

Reggie didn’t want a half-measured job; he didn’t want non-interior piers only while the back of the house was dropping. He wanted to do all the necessary work, but was deeply bothered that they would need to drill through the brand-new top floors he’d just installed.

Kyle explains that these concerns about damaging new floors are emotional, too, and they must be addressed empathically:

• “I totally get it. I know you just laid these floors. I hate to be the one to tell you this, but I wouldn’t be doing my job if I didn’t…”

• Followed by: “What are you thinking? Seems like this is really frustrating.” Then let them talk.

He stresses this isn’t manipulation; it’s customer-first sales—helping them feel heard when nobody else does. That depth of listening is part of serving, not tricking.

After wrapping the emotion section, he gives four key phrases to use constantly:

1. “Seems like…”

2. “Sounds like…”

3. “Feels like…”

4. “Looks like…”

He calls these “transparent phrases” because people do not consciously notice them; what they notice is the relief of being understood. Customers have “drawn bows”, loaded with emotion, waiting for a reason to let the arrow fly—when you say, “Sounds like that hurts a lot,” they finally fire and pour out everything.

Kyle shares a story about teaching this in a class: a student said, “Sounds like…” to him and he responded naturally, “Yeah, exactly,” while continuing on—even he didn’t notice the technique being used on him, which shows how invisible it is in conversation.

Someone asks if there’s a phrase that does the opposite (shuts people down). Kyle doesn’t go deep into that here, but they joke about the recording and battery, then he shifts to how these phrases can be used at home, to encourage your partner to open up—not to manipulate them but to give them permission to share her feelings. This technique DEMANDS a genuine interest in the good of the other person. It simply will not bear fruit long-term if you don’t have that. If you don’t have it, cultivate it, invest in it.

He points out that in many male-female conversations, the man can feel lost, just wanting a sandwich, and suddenly hears, “Don’t you agree?” That’s the perfect time to say, “Sounds like you’re feeling a lot of…”, entering the emotion you see and knowing more is about to come out—but that’s actually what helps them feel heard.

He wraps that thread by reaffirming that this approach—labeling emotions and listening—is “powerfully effective” both in personal relationships and in sales contexts.

Finally, Kyle transitions, saying, “Now let’s talk about value.” He notes he hadn’t released some material from last time because he wanted first to revisit the themes of trust and emotional work, hinting there are three layers to the “Can I trust you?” question and begins to segue into the next section of the training.