What if I genuinely hate the idea of selling anything

Then stop thinking of it as selling. A sales conversation is just a diagnosis followed by an honest answer about whether you can help. You already ran versions of this conversation in the service every time you assessed a problem and told someone straight whether you could fix it. The discomfort is with the word, not the actual skill.

How do I open the conversation without sounding like a pitch

Ask about their problem before you say anything about what you offer. Something plain like "what's going on that made you reach out" works because it hands them the floor first. People trust you faster when you clearly want to understand the problem before you try to sell them a solution to it.

What do I do when they ask how much it costs

Answer directly, then stop talking. Say your number once, plainly, and let the silence sit instead of rushing to justify it or discount it before they've even responded. If you already ran the three-number pricing method, you know your number cold and won't be doing math in front of a stranger.

How do I handle it when someone says they need to think about it

Ask one clarifying question instead of letting them go quiet. "Is it the price, the timing, or something about the fit that's got you thinking it over" usually surfaces the real objection in one sentence. Most people who say they'll think about it actually have one specific hesitation, and naming it is the fastest way through it.

What if I lose the sale because I didn't push hard enough

You didn't lose it, they weren't ready, and pushing harder rarely changes that. A hard close on someone who isn't sure just buys you a refund request or a bad review later. A clean no now is cheaper than a forced yes you have to manage afterward.

How many of these conversations does it take before it stops feeling awkward

About five. The first two or three will feel stiff no matter how well you know the script, because you're running new reps. By the fifth conversation the questions start feeling like your own words instead of a script you memorized, and that's the point where it actually starts converting.

Side Hustle

Your First Sales Conversation: A Script for People Who Aren't Salesy

Corey ReiserAug 17, 20265 min read

You don't need a sales personality to land your first customers. You need four questions, in order, and the discipline to shut up after you ask each one. That's the whole framework — no pitch deck, no closing tricks, no fake urgency. Most veterans who think they're bad at sales aren't bad at it. They've just never been handed a version of it that doesn't feel like lying.

The word "sales" is doing all the damage

Say "sales conversation" to most people leaving the service and you get a flinch. It sounds like something slick, something that requires charm you don't think you have, something adjacent to talking someone into a decision they'll regret. None of that is what actually moves a stranger to become your first customer.

What actually works is closer to a debrief. You ask what's going on, you listen for what's really broken, and you give a straight answer about whether you can fix it and what that costs. You ran this exact pattern in uniform every time you assessed a situation and reported back plainly instead of dressing it up. The skill already exists. It just needs pointed at a customer instead of a commander.

The four-question script

Use this in order, every time, whether the conversation happens over text, on a call, or standing in someone's driveway.

"What's going on that made you reach out?" Let them talk first, and don't interrupt to sell anything yet. This single question does more work than an entire pitch, because it tells you what they actually care about instead of what you assumed they'd care about.
"How long has this been a problem?" This surfaces urgency without you having to manufacture any. Someone who's been dealing with a leaking faucet for six months is in a different place than someone who noticed it this morning, and their answer tells you which one you're talking to.
"Here's what I'd do, and here's what it costs." State your plan in plain language and your price once, clearly. Don't soften it with "if that works for you" or "I know it's a lot" tacked on the end. You already priced this job with real numbers — say the number and stop talking, the same way you would quoting any other job.
"Does that work, or is something holding you up?" This closes the loop without pressure. It gives them a clean yes, and it gives you a real objection to work with instead of a vague maybe that goes nowhere.

Four questions, no script to memorize word for word — just the order and the discipline to actually wait for an answer before you move to the next one.

Silence is doing the closing, not you

The hardest part of this isn't the words. It's resisting the urge to fill the silence after you say your price or ask your closing question. Most people who think they're bad at sales are actually just bad at shutting up at the right moment — they answer their own objections before the customer even raises one, talk the price down before anyone pushed back on it, and turn a clean ask into a nervous ramble.

THE PERSON WHO TALKS FIRST AFTER THE PRICE LOSES LEVERAGE. LET THEM RESPOND.

Practice this specifically. Say your price out loud to an empty room if you have to, and force yourself to count to five in your head before you say anything else. It feels unnatural for the first handful of reps and then it starts feeling like the only sane way to have the conversation.

Handling "I need to think about it"

This isn't a no. It's usually one specific hesitation wearing a polite deflection. Instead of letting the conversation end on a vague maybe, ask directly: "Is it the price, the timing, or something about the fit that's got you thinking it over?" Nine times out of ten they'll tell you exactly what's actually stopping them, because you gave them a short list to pick from instead of an open-ended blank page.

If it's price, you can adjust scope instead of cutting your rate, same as with any other quote. If it's timing, get a specific date to follow up rather than leaving it open forever. If it's fit, thank them for their time and move on — chasing a customer who's genuinely not a match costs more than it's worth, and every hour spent there is an hour you're not spending on finding the next one.

Reps beat talent here

Nobody is naturally good at this conversation the first time. The stiffness in the first few attempts isn't a sign you're not cut out for sales — it's a sign you're doing something new, the same way your first few reps at anything unfamiliar felt clumsy before they felt automatic. By your fifth real conversation, the four questions stop sounding like a script and start sounding like you.

If you're still cold-starting your outreach before you even get to this conversation, warm and direct messages that don't get ignored is the step that comes before this one. And if you want the full build — pricing, outreach, and this exact sales conversation stacked into one system instead of pieced together on your own — that's what Line of Departure walks you through end to end. The community is also full of veterans running these same four questions right now, comparing notes on what's landing and what isn't.

Pick one person you've been putting off talking to. Ask the four questions, say your price once, and let the silence do its job. Your first "yes" is one honest conversation away, not a personality transplant.

Frequently Asked Questions

What if I genuinely hate the idea of selling anything: Then stop thinking of it as selling. A sales conversation is just a diagnosis followed by an honest answer about whether you can help. You already ran versions of this conversation in the service every time you assessed a problem and told someone straight whether you could fix it. The discomfort is with the word, not the actual skill.
How do I open the conversation without sounding like a pitch: Ask about their problem before you say anything about what you offer. Something plain like "what's going on that made you reach out" works because it hands them the floor first. People trust you faster when you clearly want to understand the problem before you try to sell them a solution to it.
What do I do when they ask how much it costs: Answer directly, then stop talking. Say your number once, plainly, and let the silence sit instead of rushing to justify it or discount it before they've even responded. If you already ran the three-number pricing method, you know your number cold and won't be doing math in front of a stranger.
How do I handle it when someone says they need to think about it: Ask one clarifying question instead of letting them go quiet. "Is it the price, the timing, or something about the fit that's got you thinking it over" usually surfaces the real objection in one sentence. Most people who say they'll think about it actually have one specific hesitation, and naming it is the fastest way through it.
What if I lose the sale because I didn't push hard enough: You didn't lose it, they weren't ready, and pushing harder rarely changes that. A hard close on someone who isn't sure just buys you a refund request or a bad review later. A clean no now is cheaper than a forced yes you have to manage afterward.
How many of these conversations does it take before it stops feeling awkward: About five. The first two or three will feel stiff no matter how well you know the script, because you're running new reps. By the fifth conversation the questions start feeling like your own words instead of a script you memorized, and that's the point where it actually starts converting.

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