Your First Conversations - Testing Your Positioning

You've done the thinking. You've built a customer avatar. You've written your positioning statement. Now it's time to stop theorizing and start testing — with real people, in real conversations.

This is where many people stall. It feels awkward. You don't want to seem desperate. You don't want to be "salesy." You don't want to be rejected. You've just lost a job and the last thing you want is more rejection.

I get it. But here's the truth that's going to change how you think about this: the conversations you're about to have aren't sales calls. They're research calls. You're not trying to sell anything. You're not trying to close anyone. You're trying to find out if the problem you've identified is real, if your positioning resonates, and if there's genuine demand for what you're thinking about offering.

That's it. Research. Curiosity. Listening. You're a detective, not a salesperson.

And here's the other truth: these conversations are the single most important thing you can do right now. More important than building a website. More important than designing a logo. More important than writing a business plan. More important than setting up an LLC. All of that can wait. These conversations cannot.

Why Conversations Beat Everything Else

There's a reason why every successful entrepreneur — from the founder of a billion-dollar tech company to the consultant who built a thriving solo practice — will tell you that talking to potential customers early was the most important thing they did.

Conversations reveal reality. Your assumptions about what people need, what they'd pay, and how they'd describe their problems are just guesses until you've validated them with real people. And your guesses are almost certainly at least partially wrong. That's not a criticism of your intelligence — it's a statement about how markets work. The only way to know what customers actually want is to ask them.

Conversations build confidence. When you hear someone say "Yes, that's exactly the problem I'm dealing with," it's fuel. It transforms your business idea from a nervous theory into something real. After five or six conversations where people confirm the problem exists, you'll feel a shift in your certainty. That confidence is what carries you through the harder stages ahead.

Conversations refine your language. You might describe the problem you solve as "streamlining operational workflows." But in conversation, you discover that your potential customers describe it as "getting rid of all the stupid manual steps in our reporting process." Their language is always better than yours for marketing purposes, because it's the language that resonates with people like them. Conversations give you that language for free.

Conversations generate leads. Even though these aren't sales calls, some of them will naturally lead to business. Someone says "wow, I really need this" and asks "so when can you start?" You didn't have to pitch. The conversation itself was the pitch.

Conversations build your network. Every conversation, even with someone who isn't a potential client, is a relationship. They might refer you to someone who is a client. They might become a client in six months. They might become a partnership opportunity. The conversations you have now are seeds for a network that will pay dividends for years.

The 10 Positioning Conversations Exercise

This is your assignment for the next two weeks: have 10 conversations with people who match (or are close to) your customer avatar. Ten is the minimum. More is better. But ten gives you enough data to see patterns.

Step 1: Identify Your 10 People

These could be:

• Former colleagues who now work at companies that fit your target profile. This is usually the easiest source. You already have the relationship. Reaching out feels natural.

• LinkedIn connections in your target industry. Look at your connections and their connections. Who has the job title of your customer avatar? Who works at the type of company you want to serve?

• People you know from industry events or associations. If you attended conferences, participated in professional organizations, or were part of industry working groups, reach out to the people you met there.

• Friends of friends in the right roles. Ask people in your personal network: "Do you know anyone who works in [your target industry] as a [your target role]?" People are surprisingly willing to make introductions when you frame it as research rather than sales.

• People you find through online communities. If your target customers hang out in specific LinkedIn groups, Reddit communities, or industry forums, you can identify potential conversation partners there. Be genuine — don't spam.

Don't overthink the list. You don't need 10 perfect matches. You need 10 people who are close enough to your avatar that their feedback will be useful. An imperfect conversation is infinitely more valuable than a perfect plan that never gets executed.

Step 2: Send the Outreach Message

Keep it short, honest, and low-pressure. Here's a template that works:

For people you know:
"Hi [Name], I'm working on something new and I'd really value your perspective. I'm exploring how people in [their role/industry] handle [the problem you're focused on]. Would you have 20 minutes for a quick call this week or next? I'm not selling anything — just trying to understand the landscape. Happy to buy you a virtual coffee as a thank you."

For people you don't know well:
"Hi [Name], I came across your profile and noticed you're a [their role] at [their company]. I'm researching how [their industry] professionals handle [the problem you're focused on]. Would you be open to a brief 15-minute call to share your perspective? I'm not selling anything — just gathering insights from people who are actually in the trenches. I'd really appreciate your time."

For introductions through friends:
"Hi [Name], [Mutual friend's name] mentioned you work in [their industry] and suggested you might have interesting perspective on [the problem]. I'm doing some research and would love to hear how you handle [specific challenge]. Do you have 15-20 minutes this week? No sales pitch, I promise — just genuinely curious about your experience."

A few notes on these messages:

• "I'm not selling anything" is critical. It lowers the barrier to saying yes and it's true — you're not selling. You're learning.
• Specific time ask ("20 minutes") makes it easy to say yes. An open-ended "would you be willing to chat?" is harder to commit to because they don't know what they're committing to.
• Mentioning their role/industry shows you're reaching out intentionally, not mass-messaging everyone in your contacts.

You'll be surprised by the response rate. Most people are flattered to be asked for their professional opinion, especially when there's no sales pressure. Expect 40-60% of the people you reach out to to say yes.

Step 3: Conduct the Conversation

Here's a conversation framework that works. You don't need to follow it rigidly — let the conversation flow naturally. But hit these key points:

Opening (2-3 minutes):
Start by thanking them for their time and briefly explaining what you're doing. "I'm exploring whether there's a need for [general description of your offering] and I want to make sure I understand the real challenges people like you face before I build anything." Then ask about them: "Tell me about your current role. What does a typical week look like for you?"

Problem exploration (7-10 minutes):
This is the meat of the conversation. Ask open-ended questions and listen:

• "What's the biggest challenge you're dealing with right now in [their area]?"
• "How does that challenge affect your day-to-day work?"
• "What have you tried to solve it? What worked? What didn't?"
• "How long has this been a problem?"
• "If you could wave a magic wand and fix one thing about [their area], what would it be?"
• "What does this problem cost you — in time, money, stress?"

Critical technique: When they describe a problem that's relevant to your area, resist the urge to immediately jump in with your solution. Instead, dig deeper: "Tell me more about that." "Can you give me a specific example?" "What does that look like week to week?" The deeper you go, the more you learn.

Positioning test (3-5 minutes):
Later in the conversation — not at the beginning — describe your positioning and watch their reaction.

"Based on what I'm hearing from people like you, I'm thinking about helping [your target customers] with [your proposed solution]. Does that resonate with your experience?"

Then be quiet. Let them respond. Watch for:

• Verbal signals: Do they say "yes, absolutely" with energy? Do they start telling you about their own specific version of the problem? Do they ask follow-up questions? These are all positive signals.
• Physical signals (on video calls): Do they lean forward? Do their eyes widen? Do they nod? These indicate genuine interest.
• Neutral signals: Do they say "yeah, I can see how that would be useful" in a flat tone? That's polite interest, not genuine excitement. It means you might need to refine.
• Negative signals: Do they say "that's not really a problem for me" or change the subject? That's valuable information. It means either this person isn't your avatar, or the problem isn't as widespread as you thought.

Value and pricing exploration (3-5 minutes):
If they've confirmed the problem exists, ask about value:

• "If someone could solve this for you reliably, what would that be worth to your organization?"
• "What are you currently spending to deal with this — in terms of people, tools, or time?"
• "Would you be more interested in a one-time project or ongoing support?"
• "What would make you hesitant to hire someone to help with this?"

Don't push for exact numbers if they're uncomfortable. Even directional information ("probably a few thousand a month" vs. "maybe a few hundred") is extremely useful for pricing.

Closing (2-3 minutes):
Thank them genuinely. Ask if there's anyone else they think you should talk to: "Is there anyone in your network who deals with similar challenges that you'd recommend I talk to?" This single question can double your conversation list through referrals.

If they expressed strong interest, it's okay to say: "I'm still in the early stages of building this, but if you're interested, I'd love to keep you in the loop as things develop." Get their permission to follow up. Don't push for a sale.

Step 4: Track What You Learn

After each conversation, immediately write down:

1. Did they confirm the problem exists? (Yes/No/Partially)
2. How did they describe the problem in their own words? (Write down their exact phrases)
3. What have they tried to solve it? (This tells you about competition and willingness to spend)
4. How did they react to your positioning? (Excited / Interested / Neutral / Not interested)
5. What did they say about value/pricing? (Any numbers or directional information)
6. What surprised you? (Anything you didn't expect)
7. Who did they refer you to? (Follow up within 48 hours)

Keep this in a simple spreadsheet or document. Don't overcomplicate it.

Reading the Results

After 10 conversations, look at the patterns:

Strong signal (move forward with confidence):
- 7+ people confirmed the problem exists
- Multiple people used similar language to describe it
- Several responded to your positioning with visible enthusiasm
- At least 2-3 said something like "When can I hire you?" or "I'd definitely pay for that"
- People referred you to others without being asked

If this is your result, congratulations. You've found a real problem with real demand. Your next steps are clear: refine your positioning based on the language people used, define your initial offering, and start selling.

Moderate signal (refine and test again):
- 4-6 people confirmed the problem, but the descriptions varied
- People were interested but not enthusiastic about your positioning
- Pricing expectations were lower than you hoped
- The conversations felt useful but not electric

If this is your result, you're on the right track but need to refine. Look at the conversations where people were most engaged — what was different about those? Maybe you need a more specific customer segment. Maybe you need to reframe the problem. Do 5-10 more conversations with adjustments and see if the signal strengthens.

Weak signal (pivot):
- Fewer than 4 people confirmed the problem
- People were polite but unengaged
- Nobody offered to refer you to others
- Pricing discussions revealed this isn't a high-value problem

If this is your result, don't be discouraged. You just saved yourself months of building something nobody wants. Go back to your Problem Inventory from Chapter 1, pick a different problem, and run the same 10-conversation exercise again. The goal isn't to be right on the first try — it's to find the right problem-market fit as quickly as possible.

Common Mistakes in Positioning Conversations

Mistake 1: Talking too much. The ideal ratio is 30% you, 70% them. You're there to learn, not to present. If you catch yourself on a monologue, stop and ask a question.

Mistake 2: Leading the witness. Don't ask "Wouldn't it be great if someone could help you with compliance?" That's like asking "Wouldn't you like free money?" Instead ask "What are your biggest challenges right now?" and see if compliance comes up organically. If it doesn't, that's important information.

Mistake 3: Pitching too early. If you launch into your positioning in the first two minutes, you've turned a research call into a sales call. Spend at least half the conversation listening before you share your positioning.

Mistake 4: Only talking to friends. Friends will tell you your idea is great because they don't want to hurt your feelings. Make sure at least half your conversations are with people who have no personal loyalty to you and will give you honest feedback.

Mistake 5: Giving up after one bad conversation. One person's lack of interest doesn't invalidate your idea. You need the full 10 to see the pattern. Don't abandon ship based on a single data point.

Mistake 6: Not following up on referrals. When someone says "You should talk to my colleague Janet," email Janet within 48 hours. Warm referrals have a much higher acceptance rate than cold outreach, and they decay quickly. A week later, Janet's already forgotten her colleague mentioned you.

What Happens After the 10 Conversations

If your 10 conversations produced a strong signal, here's what to do next:

1. Refine your positioning statement using the exact language your potential customers used. Their words are always better than yours for marketing.

2. Define your initial offering. Based on what people told you they need and what they'd pay, create a simple, clear description of what you're offering. Don't overcomplicate it. A single service at a single price point is all you need to start.

3. Go back to the 2-3 people who were most enthusiastic and say: "I've been building what we talked about. Would you be open to being one of my first clients at a reduced rate? I'd love to prove this out with someone who really understands the problem." This is how you get your first paying customer.

4. Ask everyone you spoke with for one more referral. Say: "Our conversation was incredibly helpful. Based on what I learned, I'm moving forward. Is there anyone else you think I should talk to?" Second-round referrals are often even better than first-round because you've refined your pitch.

These 10 conversations are the bridge between having an idea and having a business. They're the validation step that most people skip — and the ones who skip it usually end up building something nobody wants and wondering what went wrong.

You're not going to make that mistake. You're going to do the work. You're going to talk to real people. And you're going to build something that's rooted in genuine demand rather than hopeful assumptions.

Start today. Send the first message. The first conversation is always the hardest and the most important.

Key Takeaways:

• The best way to test your positioning is through real conversations, not by thinking about it alone
• 10 conversations with potential customers will reveal patterns about whether your problem and positioning are real
• If 7+ people describe the same problem and several respond enthusiastically, you've found something worth building
• Lukewarm responses aren't failure — they're information that helps you refine before investing further