Your First Conversations - How to Talk to Potential Customers

The hardest part of your first customer conversations isn't what you say — it's fighting the urge to pitch. Your instinct will be to explain your service, describe your experience, and convince the other person that you can help them. Resist that instinct.

The best first conversations are 80% listening and 20% talking. You're not selling yet. You're learning. You're discovering whether the problem you've identified is real, how much it matters, and whether this person would pay to solve it.

This chapter gives you a complete conversation framework, word-for-word scripts, and a system for evaluating every conversation so you know exactly when you're ready to move from "exploring" to "proposing."

Why Listening Beats Pitching

Let's start with why listening matters more than talking in these early conversations. There's a psychological principle at work here called the reciprocity effect. When you genuinely listen to someone — when you ask thoughtful questions and let them talk about their problems without interrupting — they feel heard. And when people feel heard, they trust you. Trust is the foundation of every business relationship, and it's built through listening, not presenting.

Here's what happens when you pitch instead of listen: The prospect smiles politely, waits for you to finish, and says "That sounds interesting, let me think about it." Then they never get back to you. That's not because your service is bad — it's because you never gave them a chance to tell you what they actually need. You assumed you knew their problem and offered your solution. But assumptions kill sales.

Here's what happens when you listen first: The prospect tells you about their real frustrations. They get specific about what's costing them time, money, or sleep. They explain what they've tried before and why it didn't work. By the end of the conversation, you know exactly what they need — and when you offer your service, it's not a pitch anymore. It's a direct response to a problem they just told you about. That's the difference between a 10% close rate and a 50% close rate.

Think about it from the other side. Have you ever been on a sales call where someone launched into a presentation without asking you a single question? How did that feel? Now think about a conversation where someone asked genuinely curious questions about your work, listened carefully, and then said "Based on what you've shared, here's how I think I could help." Which one felt more compelling?

The 20-Minute Conversation Structure

Here's the framework that works for first conversations. It's structured enough to keep you on track but flexible enough to feel natural.

1. Introduction (2 minutes)

Set the tone immediately. Be warm, direct, and honest about what this call is. Don't try to be slick or mysterious. Transparency builds trust faster than anything else.

What to say:

"Thanks for making time for this. As I mentioned, I'm exploring a business helping [customer type] solve [problem]. This isn't a sales call — I'm genuinely trying to understand what people in your role are dealing with so I can build something that actually helps. Your perspective would be really valuable."

Why this works: You've told them exactly what to expect. They know it's not a pitch. They know their input is valued. They can relax and be honest instead of feeling like they need to defend against a sales tactic.

What NOT to say: Don't open with a long description of your background. Don't say "Let me tell you about my new business." Don't start with your positioning statement. All of that centers the conversation on you, and you want it centered on them.

2. Their Situation (5 minutes)

Get them talking about their world. Don't steer the conversation yet — just ask open-ended questions and listen. Your goal in this section is to understand their context before diving into problems.

Questions to ask:

• "Tell me about your role and what you're focused on right now."
• "What's your biggest challenge at the moment?"
• "What takes up the most time or energy in your work?"
• "How is your team structured? Who do you work with most closely?"
• "What's changed in your business over the last 6-12 months?"

What to listen for: Pay attention to emotion, not just facts. When someone says "We're dealing with supply chain issues" in a flat tone, that's different from someone who says "Our supply chain is killing us — we lost three major accounts last quarter because we couldn't deliver on time." The second person has a problem they'd pay to solve. The first person has a challenge they've accepted.

Also listen for language. When people use words like "frustrated," "nightmare," "keeps me up at night," "bleeding money," or "I don't know what to do" — those are buying signals. They indicate real pain, not just mild inconvenience.

Pro tip: Take notes during this section, but ask permission first: "Do you mind if I jot down a few notes? I want to make sure I capture this accurately." This shows respect and signals that you're taking their input seriously.

3. The Problem — Go Deep (8 minutes)

This is the most important part of the conversation. When they mention a challenge that relates to your area of expertise, dig into it. Don't skim the surface — ask follow-up questions that help you understand the real depth, cost, and urgency of the problem.

Questions to ask:

• "Tell me more about that — how does it actually show up day to day?"
• "How long has this been a problem?"
• "What have you tried to solve it? Why didn't that fully work?"
• "If you had to put a rough number on what this problem costs you — in time, money, or stress — what would you say?"
• "Who else in your organization is affected by this?"
• "What would it mean for your business if this problem was solved in the next 90 days?"
• "Is this something that's getting worse over time, or is it stable?"
• "When you think about your priorities for the next quarter, where does this rank?"

The magic question: "If you had to put a rough number on what this problem costs you" is the single most powerful question in this conversation. Most people have never quantified their problems. When they try to do it out loud for the first time, they often surprise themselves. "I guess... between lost productivity and the workarounds we've built... it's probably costing us $10,000 to $15,000 a month." Now both of you know the problem is worth solving.

What to listen for: You're evaluating three things:

1. Severity — Is this a minor annoyance or a significant pain? (Scale of 1-10)
2. Urgency — Do they need this solved now, or is it a "someday" problem?
3. Willingness to pay — Have they spent money trying to solve this before? Are they actively looking for a solution?

If a problem scores high on all three dimensions, you're looking at a potential client. If it scores low on any dimension, this person might not convert — but they might refer you to someone who has a more urgent version of the same problem.

The "Tell me more" technique: When you're not sure what to ask next, the phrase "Tell me more about that" is your safety net. It's impossible to overuse. People love talking about their problems to someone who's genuinely interested, and every time you say "Tell me more," they go one layer deeper. That deeper layer is where the real insights live.

4. Your Idea — Brief and Curious (3 minutes)

Now — and only now — share what you're thinking. Keep it short. Frame it as a hypothesis, not a pitch. You're testing an idea, not selling a product.

What to say:

"Based on what you've shared, here's what I'm exploring: [one or two sentences about your service]. Does that sound like it would be helpful in your situation?"

Example: "Based on what you've shared about the compliance documentation backlog, here's what I'm thinking: I could help your team build a compliance management system that automates 80% of the documentation you're currently doing manually, and train your team to maintain it going forward. Does that sound like it would address the problem you described?"

Then stop talking and listen. Watch their reaction carefully:

• They lean forward, ask questions, want specifics — Strong interest. This is a potential client.
• They nod thoughtfully, say "That could be interesting" — Moderate interest. They need more information or need to see a specific proposal.
• They politely nod and change the subject — Low interest. The problem isn't painful enough, your solution doesn't match their need, or the timing isn't right.
• They immediately ask "How much would that cost?" — Very strong interest. When someone jumps to pricing, they're already mentally buying. Don't answer with a specific number yet — say "It depends on the scope, but let me put together a specific proposal for you. Can we schedule a follow-up call next week?"

5. Close — Always Leave with a Next Step (2 minutes)

Every conversation should end with a clear next step. This is non-negotiable. A conversation without a next step is a dead end. Always leave with something concrete scheduled or committed.

If they're interested:

"This sounds like it could be a great fit. Would you be open to a follow-up call next week where I can share a more specific proposal based on what we discussed today? I'd want to come back with something concrete — scope, timeline, and investment — so you can evaluate whether it makes sense."

If they're somewhat interested but not ready:

"I appreciate you sharing all of this. It sounds like the timing might not be perfect right now, but this is clearly a problem that needs solving. Would it be okay if I followed up in [timeframe] to see if anything's changed? In the meantime, I'll send you a brief summary of what we discussed."

If they're not interested but were helpful:

"I really appreciate your time and insights. This conversation has been incredibly valuable for shaping what I'm building. Do you know anyone else who's dealing with a similar challenge who might benefit from a conversation like this?"

Always ask: "Is there anyone else in your network I should be talking to?" This question should end every single conversation, regardless of outcome. Referrals from people you've had good conversations with are the highest-converting leads you'll ever get.

After the Conversation: Your Evaluation Framework

Within 30 minutes of each conversation, fill out this evaluation. Don't wait until the end of the day — your memory of the emotional cues and specific language will fade.

Conversation Scorecard:

• Name: ___
• Date: ___
• Did they confirm the problem exists? (Yes / No)
• How severe is the problem? (1-10)
• How urgent is the problem? (1-10)
• Have they tried to solve it before? (Yes / No — if yes, what did they try?)
• Did they respond positively to your idea? (Enthusiastic / Somewhat interested / Polite but disengaged)
• Did they ask follow-up questions about how you'd help? (Yes / No)
• Did they ask about pricing? (Yes / No — if yes, this is a very strong signal)
• Did they offer to refer you to someone? (Yes / No)
• What was the agreed next step? ___
• One key insight I learned: ___

After 5 conversations, review your scorecards side by side. You'll start to see patterns: certain problems come up repeatedly, certain types of people are more receptive, certain aspects of your idea resonate more than others.

After 10 conversations: If 7 or more people confirm the problem exists and 3 or more show genuine interest in your solution, you're on the right track. Move forward with confidence. If fewer than 5 confirm the problem, you may need to adjust your positioning or target audience. That's not failure — that's data.

Common Mistakes in First Conversations

Mistake 1: Talking too much. This is the number one killer. If you talked for more than 20% of the conversation, you talked too much. Practice letting silence happen. After you ask a question, wait. Let them fill the space. The most powerful tool in a conversation is a pause.

Mistake 2: Pitching too early. If you describe your service before you've spent at least 10 minutes understanding their situation, you're pitching too early. Hold back. Let the conversation develop.

Mistake 3: Accepting vague answers. When someone says "Yeah, that's kind of an issue for us," don't nod and move on. Ask "Can you give me a specific example?" or "Tell me about the last time that happened." Vague answers give you nothing to work with. Specific stories give you everything.

Mistake 4: Asking yes/no questions. "Do you have supply chain problems?" gets you a yes or no. "Tell me about the biggest supply chain challenge you've faced this year" gets you a story. Stories are where the gold is. Reframe every closed question into an open one.

Mistake 5: Not asking about money. Many people feel uncomfortable asking about the financial impact of a problem. Get over it. If you don't understand the financial cost of the problem, you can't price your solution. The question "What would you estimate this costs your business?" is professional, not nosy.

Mistake 6: Skipping the next step. If you end a conversation with "Great talking to you, I'll be in touch," you've wasted the conversation. Always end with a specific, scheduled action: a follow-up call date, a proposal delivery date, or a referral introduction.

How Many Conversations Do You Need?

A common question is "How many conversations should I have before I start proposing?" The answer is: at least 5, no more than 15.

5 conversations is the minimum to spot a pattern. If 3 out of 5 people describe the same problem in similar terms, that's a strong signal.

10 conversations gives you high confidence. You've heard the problem from multiple angles, you've refined how you describe your solution, and you've probably identified 2-3 people who are genuinely interested.

15 conversations is the maximum before you should make a proposal to someone. If you've had 15 conversations and haven't found a single interested prospect, you need to go back and reassess your positioning, your target audience, or your solution.

But here's the thing: you don't need to wait until you've finished all your conversations before proposing. If conversation number 3 produces someone who says "I need this — when can we start?" — make a proposal. Don't hold them off because you haven't finished your research. Seize the opportunity.

Exercise: Practice Run

Before your first real conversation, do a practice run. Find a friend, family member, or former colleague who's willing to role-play for 20 minutes.

Setup: Give them a brief description of the type of person they're playing: "Pretend you're a VP of Operations at a mid-size manufacturing company. You're dealing with delivery delays and unhappy customers."

Run through the full 20-minute structure:
1. Introduction (2 min)
2. Their situation (5 min)
3. The problem — go deep (8 min)
4. Your idea (3 min)
5. Close with a next step (2 min)

After the practice:
- Ask your role-play partner: "Did I talk too much? Did you feel heard? Was there a moment where you felt I was pitching instead of listening?"
- Time yourself. Did you stick to the structure, or did certain sections run long?
- Record yourself if possible. Listening to yourself on playback reveals verbal habits you'd never notice otherwise — filler words, rushing through questions, interrupting answers.

Run through it at least twice. The first time will feel awkward and stiff. The second time will feel more natural. By the time you have your first real conversation, the structure will be in your muscle memory and you can focus on actually listening instead of remembering what to say next.

The Conversation Funnel

Here's how your conversations typically progress from first contact to client:

Stage 1: Discovery call (this chapter) — 20-minute exploratory conversation. Goal: understand their problem and assess fit.

Stage 2: Follow-up call — 30-45 minute deeper conversation, often with a specific proposal. Goal: present your solution and discuss terms.

Stage 3: Proposal review — They review your written proposal (email or one-page doc). Goal: address any remaining questions or concerns.

Stage 4: Agreement — They say yes and you formalize the arrangement. Goal: get commitment and payment.

Not every prospect moves through all four stages. Some will drop off after Stage 1 (the problem isn't urgent enough). Some will drop off after Stage 2 (budget constraints, timing issues). That's normal. Your job is to move interested prospects forward, one stage at a time, and to recognize when someone isn't a fit so you can invest your energy elsewhere.

Key Takeaways:

• The best first conversations are 80% listening and 20% talking
• Structure: Introduction, Their Situation, The Problem (go deep), Your Idea (brief), Close (next step)
• Always end with a next step — either a follow-up call or a referral request
• After 10 conversations, patterns will emerge that tell you whether you're on the right track
• Use the conversation scorecard after every call to track patterns and make data-driven decisions about your next move