You know the rules for good conversations. You know what questions to ask. But none of that matters if you cannot get in front of the right people. This chapter covers practical strategies for finding and starting conversations with potential customers — without being sleazy about it.
Why Finding Conversations Feels Hard
Most founders treat customer conversations as a separate, intimidating task. They imagine cold-calling strangers or begging busy executives for time. This mindset makes the whole process feel awkward and artificial. The reality is much simpler: conversations are everywhere, and most people are happy to talk about their problems if you approach them the right way.
“If you’re having trouble finding conversations, you might not have a clear enough idea of who you’re trying to help.”
— Rob Fitzpatrick
The first barrier is usually not access — it is clarity. If you cannot find people to talk to, it is often because you have not defined your customer segment precisely enough (more on this in Chapter 7).
Cold Conversations
Cold outreach gets a bad reputation, but it can work well if you approach it as genuine learning rather than a sales pitch.
Cold Outreach That Works
- Keep it short: Your email or message should be three to five sentences. Busy people do not read long pitches.
- Show credibility: Mention a mutual connection, a relevant credential, or specific knowledge of their industry.
- Ask for learning, not selling: “I’m trying to understand how companies like yours handle X. Could I ask you a few questions?”
- Make it easy to say yes: Offer a 10-minute call, not a 60-minute meeting.
Example Cold Email
Subject: Quick question about [their specific problem]
Hi [Name],
I noticed [specific detail about their company/role]. I’m researching how [their industry] handles [specific problem], and your team seemed like a great example.
Would you be open to a quick 10-minute chat? I’m trying to learn, not sell anything.
Thanks,
[Your name]
This works because it is specific, short, and low-commitment. You are asking for their expertise, which most people enjoy sharing.
Warm Introductions
Warm introductions are more effective than cold outreach. The key is to make the introduction easy for the person connecting you.
Getting Good Warm Intros
- Be specific about who you want to meet: “I’m looking to talk to office managers at companies with 50-200 employees” is better than “I want to talk to potential customers.”
- Give them a forwardable message: Write the introduction email yourself so they can just forward it.
- Reduce their risk: Make it clear you are learning, not selling. People are more willing to make introductions if they do not think you will pitch their contact.
Seizing Serendipity
Some of the best conversations happen by accident — at conferences, meetups, dinner parties, or even in line at a coffee shop. The trick is being prepared to turn small talk into useful learning.
Serendipity Scripts
- At a conference: “What brings you here? …Oh, you work in [industry]? I’ve been curious about how people handle [problem].”
- At a dinner party: “What do you do? …That’s interesting. What’s the most frustrating part of your job?”
- At a meetup: “I’m exploring ideas around [topic]. Have you run into [specific problem]?”
The transition from social small talk to useful learning should feel natural, not like an ambush. If it feels forced, you are probably pitching rather than asking.
Organizing and Finding Communities
Instead of hunting for individuals, go where your target customers already gather.
Where to Find Your Customers
- Industry conferences and trade shows: High concentration of relevant people in a short time
- Online forums and communities: Reddit, Slack groups, Discord servers, LinkedIn groups
- Meetups and local events: Lower stakes and more casual than conferences
- Industry publications and blogs: Comment sections and author pages lead to real people
- Your existing network: You probably know someone who knows someone
“Going to them is always better than trying to get them to come to you.”
— Rob Fitzpatrick
Landing Pages and Other Hooks
You can also use lightweight hooks to attract conversations — a blog post about the problem, a landing page collecting email addresses, or a short survey. These are not replacements for real conversations, but they can be conversation starters.
Using a Landing Page for Conversations
- Create a simple page describing the problem (not your solution)
- Include a call to action like “We’re researching this problem — mind sharing your experience?”
- Use responses as conversation starters, not as data
- Follow up personally with anyone who engages
The goal is not to collect survey data — it is to identify real people you can talk to in depth.
How Many Conversations Do You Need?
There is no magic number, but Fitzpatrick suggests that patterns usually start to emerge after five to ten conversations with a well-defined customer segment. If you are not seeing patterns, your segment may be too broad.
Signs You Have Talked to Enough People
- You can predict what someone will say before they say it
- The same problems and workflows keep coming up
- You stop being surprised by the answers
- You hear the same objections and concerns repeatedly
When conversations stop teaching you new things, you have probably talked to enough people in that segment.
Key Takeaways
- If you cannot find people to talk to, your customer segment is probably too vague
- Cold outreach works if you keep it short, specific, and focused on learning
- Warm introductions are more effective — make them easy by writing the intro email yourself
- Serendipitous conversations at events and social settings produce excellent data
- Go where your customers already gather instead of trying to attract them to you
- Patterns emerge after five to ten conversations with a well-defined segment