Selling Your Underwear by Coffee With Steve

When I was a brand new teenager and the Internet was just starting, my father had gotten fired from the last job he had ever gotten fired from, and he’d been fired from a lot of places.

The few times in my own life where I have been fired, it’s been because I didn’t live up to the employer’s standards—that was my first job at an auto repair shop where pretty much all I did was sweep the floor because my dad said if I didn’t have anything to do, sweep the floor. I’ve also been fired for selfish personal reasons. A grocery store assistant manager in Columbus, Ohio, tried to encourage my wife to leave me. That was a fun experience, let me tell you. I was let go once because they were shutting down the entire office, and the office manager had to drive me home, and he was in tears the whole way. I was the last person he fired that day. That was a whole weird situation. In a meat-packing warehouse, I was fired for being sick one too many days. That actually happened at a t-shirt factory here in New Hampshire as well, but I swear when I woke that morning, my foot really was turned at an acute 88 1/2 degree right angle to the left.

You know, there is always some kind of reason or excuse. But my dad was always fired for just working too damn hard, and you can read about his sweat down the crack of your a** in 30 below weather philosophy in my piece The Machine Was Hungry.

I think most of the reason for his opening C&S Lumber was not to get fired anymore.

C&S Lumber had basically two streams of income that built on top of each other. He’d find buyers, figure out what they needed, and then he’d buy the lumber from the tiny little Ohio sawmills—often cobbling together orders between sawmills. So a full order might come from three different sawmills. Very seldom was he able to gather one single order from one single sawmill. But these smaller sawmills were often mom & pop operations, and the lumber was often cheaper than what you’d purchase from a bigger named sawdust chop shop. He could get good deals and made the difference between the purchase and the later sale. That was income stream number one.

Income stream number two was that he’d contract his grading services to the sawmills he purchased the lumber from. Here’s a random YouTube video of a bunch of Amish grading lumber. The kids pulling the lumber off into different sorted piles—yeah, that was my job, except my brother and I were a lot faster at it than what’s shown on the video.

Now they have these chains that float the boards down the rows, and the art form of pivoting and slinging boards has rather been lost I’m afraid.

But because my father ran his own business, his days always began the same way. Mom would make sure the coffee pot was ready to fly, and he’d sleep until the first phone call came in. I or my brother ran the portable into Mom and Dad’s bedroom, and he’d sit on the edge of the bed in his underwear, ass crack hanging out, eyes half closed, making some kind of deal. His birthday is coming up this Saturday, so most likely, I will get a phone call about how I insulted him about his sales abilities. You can wish him a happy birthday here: https://www.facebook.com/stephen.bargdill, and if you’re like me, be prepared for his politics.

And Dad lived on the phone. I remember three and four-hour-long conversations.

But I tell you, I will never be able to do that—because I say enough stupid things when I’m fully awake, I can’t imagine what even more stupid things I’d say before my first few or five coffees.

This is all to say that this past weekend, I spent my time at a local democratic get-together for script practice. I got to play a disgruntled but potential voter.

I think I asked, if I remember correctly, if I could pretend to play the part of a gun-toting disenfranchised MAGA supporter who lost all his seasonal blueberry pickers and now I have to cater to those dang liberals with pick-you-own tours.1 23

Anyway. This is my point. My dad would spend hours and hours on just one phone call. I’m not sure how he got business done. I don’t think he ever had a script.

From day one in real estate, I was introduced to scripts and encouraged to practice them over and over until I was exhausted. Gary Keller even says something like the five jobs of a Realtor are

1. Lead generation

2. Lead follow-up

3. Going to appointments

4. Negotiation

5. Practice scripts and role play

If you’re a salesperson or a Realtor, you probably already know what a script is. But if you don’t: a script usually means a pre-written set of words, questions, or dialogue that salespeople use in client interactions—think of it as a cheat sheet for conversations.

They’re most often used for:

• Cold calls/prospecting → what to say when calling expired listings, FSBOs (For Sale By Owner), or circle-prospecting neighborhoods.

• Listing presentations → how to frame value, commissions, and marketing plans.

• Buyer consultations → how to walk a new client through financing, agency, and the search process.

• Objection handling → prepped responses to common pushbacks like “I want to wait until spring” or “Why should I pay 6% commission?”

The intent behind scripts is consistency and efficiency—they make sure agents don’t freeze up or miss key points. The following script is from The Close:

Agent: Hi there! I’m [Your Name], a real estate agent with [Your Company]. Is this [Buyer’s Name]?

Buyer: Yes, it is.

Agent: Fantastic! How are you today?

Buyer: I’m doing well, thanks. How about yourself?

Agent: I’m great, thank you for asking! I understand you’re exploring the possibility of buying a property. Do you have a few minutes to chat about what you’re looking for?

Buyer: Sure, I have some time.

Agent: Wonderful! To start, may I ask what’s motivating your move right now?

Buyer: [Buyer explains their situation.]

Agent: That makes a lot of sense. Finding the right home to match your needs is crucial. Have you identified any specific areas you’re interested in, or are you still exploring your options?

Buyer: [Buyer provides details.]

Agent: [Area] is a great choice. Are there specific features or amenities you’re looking for in your new home?

Buyer: [Buyer provides details.]

Agent: Excellent! These details really help me understand what you’re looking for. I can provide you with a personalized list of properties that match your criteria. Also, I offer a complimentary comparative market analysis to my clients, which could be very helpful in understanding the market better. How does that sound?

Buyer: That sounds good.

Agent: Perfect! I’d love to discuss this further and dive into more details. Could we schedule a time for a coffee meeting or a Zoom call, whichever you prefer?

Buyer: [Zoom call/in-person] works for me.

Agent: Great. How does [Time Options] work for you?

Buyer: [They provide a time.]

Agent: Fantastic! I’ve got us down for [confirmed time and date]. Can I have your email to send you the [Zoom link/in-person meetup details] and a brief introduction to the properties we’ll discuss?

Buyer: Sure. It’s [email].

Agent: Got it. I’ll send that over to you. I’m really looking forward to helping you find your ideal home. If you have any questions before our meeting, feel free to reach out. Here’s my contact information: [your contact information].

Buyer: Thank you. I appreciate your help.

Agent: It’s my pleasure, [Buyer’s Name]. Talk to you soon!

And you know, as a college professor, I had a ton of scripts. I didn’t call them scripts. I called them presentations. Or when I wanted to be fancy, pedagogies.

In my first class of the semester in college composition, all I did was tell stories. I told the same stories semester after semester, and each new group of students thought I was just riffing. But I had a purpose, because in the second class I asked them if they remembered the stories, and then as they recounted what I told them, we diagrammed the plots on the board. And then they thought (of course), oh wow, he’s brilliant.

The elections the politicians are prepping for are local positions on the school board and city council. The host provided us actors with a list of various questions:

• Why are you running for office?

• How would you make sure teachers get a fair deal salary-wise?

• Is there someone running against you?

• Are you a Democrat or a Republican?

We each sat at a door, and the candiages rotated around the house and knocked on the door. Like literally and actually knocked.

Then they worked through their spiel. Some of them were pretty nervous. The presentations I appreciated the most were the ones where they didn’t have an answer for my question, so they pulled out a notebook and wrote the question down and said they’d follow up with me. But they didn’t just say they’d follow up—they asked for specific contact information so that they could follow up.

When candidates spoke from their hearts about their absolute passions, that’s when they did their best.

Scripts often feel like they were written by a robot that studied human needs just long enough to weaponize them. They’re built to trap someone into a yes, not actually uncover the truth.

• They create false urgency.
  (“If I could sell your house for the price you want today, would you sign right now?” → classic cornering tactic.)

• They flatten people.
  Every seller becomes “the seller,” every buyer becomes “the lead.” The script assumes their motivations before they even open their mouths.

• They train agents to talk at, not with.
  You become a parrot with commission breath instead of a human being.

• They’re fear-based.
  Most scripts are written from the perspective of scarcity: if you don’t say this exact line, you’ll lose the deal. Which is bullshit.

And the worst part? People know when you’re reading from a script. Their defenses go up immediately because they’ve heard that same line from three other realtors. Scripts make you interchangeable—another voice in the noise—when what you need is to be the one who doesn’t just feel real but is real.

If you want to hear two guys dismantle the sleaziest parts of sales and scripts while making you laugh at your bad habits, tune into Two Bobs.

The show is hosted by Blair Enns (author of The Win Without Pitching Manifesto, Pricing Creativity, and The Four Conversations) and David C. Baker (author of The Business of Expertise).

On paper, it’s a podcast for creative agencies. In practice, it’s a masterclass in conversation frameworks, pricing strategy, and positioning that applies to anyone who has to sell without feeling like a hustler. Blair and David mix hard truths, frameworks you can actually use, and a kind of dry wit that makes you feel like you’re eavesdropping on two very smart uncles at the back of the bar. Which is tots my style.

It’s not scripts, it’s not hype, it’s how to have better conversations that make people want to pay you.

Blair’s The Four Conversations showcases a map of sales frameworks. He breaks the whole sales-dance into four distinct types of conversations:

1. Diagnostic
   This is where you shut up and play doctor. The only agenda is to understand: what’s hurting, what’s broken, what’s frustrating them? You’re not pitching, you’re probing. The magic comes when the other person realizes you get their situation more clearly than they’ve ever articulated it themselves.

2. Value
   Once you’ve diagnosed, you define what better looks like. Success has to be in their words, not yours — is it less stress, more money, faster speed, public perception? You tie solutions to outcomes that matter to them. Without this step, you’re just selling features instead of futures.

3. Options
   This is where you flip the power dynamic. Instead of the tired one-shot “sign or walk” pitch, you lay out structured choices: the fast/lean version, the balanced middle, the full-tilt premium. Options change the frame from “Do I work with you?” to “How do I want to work with you?”

4. Closing
   Now you recap the journey: here’s what you said you wanted, here’s how we defined success, here are the options, and here’s the path you leaned toward. The close isn’t a trap question, but an invitation to confirm alignment. If something snags, you cycle back to the right earlier conversation (diagnostic, value, or options) instead of bulldozing.

Together, these four conversations shift the whole energy of sales. You stop being the pushy closer with commission breath and start being the guide who knows the terrain. No scripts, no gimmicks — just frameworks that let you stay human while still moving the deal forward.

Unfortunately, these conversations are not quickie five-minute deals that run through a memorized script. Sometimes, like my democrat friends practicing to run for office, you only have five minutes for a script, but it should be a script that initiates future engagement instead of flattening people.

And besides, politics aside, more people should be like my dad, sitting on the edge of the bed in their underwear, ass crack hanging out, eyes half closed, making some kind of deal. Because that art-form, I’m afraid, is in short supply these days.

🗂️ Translation Grid: From Script to Framework

1. Cold Prospecting Call

• Script Version (ugh):
  “Hi Steve, this is John with ABC Realty. I was just calling to see if you’re thinking of buying or selling a home this year.”

• Framework Version (Diagnostic):
  “Steve, I know the market’s been shifting fast — what’s been your experience with it lately?”
  → Instead of fishing for yes/no, you diagnose their lived reality.

2. FSBO (For Sale By Owner)

• Script Version (ugh):
  “I noticed you’re selling your home yourself. I can get you more money in less time if you list with me.”

• Framework Version (Value):
  “I saw you’re handling the sale on your own. What does a successful sale look like for you — is it speed, max price, or something else?”
  → Shifts from I can do better than you → to clarifying their definition of winning.

3. Listing Presentation / Commission Defense

• Script Version (ugh):
  “Our marketing plan is the best in town. We do photos, staging, open houses, digital ads… That’s why we charge 6%.”

• Framework Version (Options):
  “We can list as-is and go for speed. Or we can do light prep for a mid-range bump. Or we can go full staging/marketing for maximum price. Which path feels most aligned with your goals?”
  → Shifts from defending commission → to putting structured choices in their hands.

4. Closing the Client

• Script Version (ugh):
  “If I could sell your house for the price you want, would you sign with me today?”

• Framework Version (Closing):
  “So here’s what I heard: you want to be in a new place by June, and minimizing stress matters as much as the final number. We mapped three routes, and you leaned toward the mid-range prep. Should we move forward with that plan?”
  → Shifts from trap question → to mirror back their words, confirm choice, then invite the commitment.

Why This Works

• Scripts = manipulation.

• Frameworks = collaboration.
  When you rewire the structure, you don’t sound like “that realtor.” You sound like the one person who actually heard them.