Hello and welcome back to Founder-Led Outbound 💬, with actionable strategies for business owners to win new clients predictably, without a sales team.
In the last edition, we broke down how to source and enrich lead data for your Go-To-Market: finding the right companies, understanding their context, and identifying the right people to reach out to.
This week, we’re shifting gears. Now that you’ve got high-quality leads, the next step is making your outreach count. And whether you’re reaching out via cold email, LinkedIn, or even calling; it all starts with great messaging.
This edition lays the foundation for that. So buckle up and let’s dive into it.
Rethinking Your Outreach Goal 🤔
Even the best prospect list won’t help if your messaging misses the mark.
Your initial outreach isn’t for selling or even booking meetings right away. It’s designed to spark curiosity, create interest, and offer immediate value so prospects feel compelled to act.
Yet most outreach still chases outdated metrics, like prioritizing reply rates above all else. Replies alone don’t pay the bills, and they don’t always reflect genuine interest.
Think about it: If a 5% reply rate sounds like success, imagine walking into a room with 100 people, asking a question, and having 95 ignore you. Would you consider that a win? Probably not, but that’s how many outreach campaigns measure success today.
Chasing replies alone often leads to:
• High-volume spamming, making prospects feel like just another number.
• Burnout from constant rejection.
• Ignoring what prospects actually care about.
Instead, your only goal should be triggering an ACTION. Replies can be part of it, but broader actions often come from genuine interest, such as:
• Visiting your landing page
• Booking a demo
• Requesting a PDF guide
• Watching a short video
• Joining your newsletter
Once you shift from chasing replies to triggering actions, your outreach becomes more valuable and far more effective. Let’s look into how that works.
Why Most Cold Messaging Doesn’t Work 🚮
Over the years, I’ve tested every outreach formula under the sun; from SaaS playbooks to frameworks from growth gurus. Most messages still sound something like this:
• “We’re an industry-leading platform helping teams streamline productivity…”
• “Do you have 15 minutes to discuss your goals?”
• “Just following up to see if you’re interested…”
These fail because they’re about you, your product, and your agenda; not the prospect and their real problems.
The truth is, most outreach messages share common mistakes:
• Too generic: Prospects instantly feel like they’re one of a thousand receiving the same message.
• Self-centered: The message pitches your solution, not their specific pain.
• Lack clear relevance: It doesn’t clearly explain why you’re contacting them specifically and right now.
If you want prospects to pay attention and actually respond, your message needs to clearly focus on a relevant business problem they’re experiencing today, not your pitch or your features.
In other words, stop writing for yourself, and start writing for your prospect.
What World-Class Messaging Is Built Of 💌
Great messaging doesn’t come from clever templates or blasting out hundreds of emails. It comes from being clear, relevant, and immediately valuable. To get there, you need to focus on two key areas: the content of your message and how you format it. Let’s dive into each.
1. Copy Content 📜
Forget automated sequences or clever templates for a second. Imagine you could only send ONE carefully crafted, manual message to your ideal customer. What would you say to make sure they act?
The Foundation of Great Messaging: The YYY Framework
The best-performing outbound messages consistently answer three fundamental questions, what I call the “3 WHYs”, the pillars of the YYY framework.
• Why Them? Why is this message relevant to this specific prospect right now? This is the relevance of your message.
• Why You? Why should they trust or listen to you? This is your credibility.
• Why Act? Why should they respond or take action immediately? This is your compelling offer.
When your outreach clearly covers these three elements, your prospect instantly sees why they should care, making them far more likely to engage.
Here’s exactly how you can put this into practice:
1. Why THEM? (Relevance)
Prospects always wonder:
“Why are you messaging me specifically?”
Generic approaches like “We help companies like yours…” won’t cut it. Instead, show you’ve done your research:
• Observation: Identify a specific, recent event (hiring, funding round, growth) indicating a challenge or need.
• Impact: Explain how this event might be holding them back from their goals. (PAIN)
Example:
❌ “Saw you’re a tech company. We offer analytics solutions.”
✅ “It looks like you recently hired two analysts, which usually means reporting is becoming challenging.
This is called relevance, and it’s not the same as ‘personalization’.
Personalization usually involves superficial things, like mentioning someone’s recent LinkedIn post or their university. But this rarely makes prospects care and can even backfire by feeling forced.
Relevance goes deeper. It explains exactly why you’re reaching out and how you can solve a specific problem the prospect faces. Personalization at scale fills inboxes with fluff nobody wants. Relevance at scale takes more work but is far more effective, showing you respect their time and have real value to offer.
Here’s an example of an email that’s personalized, yet completely irrelevant:
2. Why YOU? (Credibility)
Next, prospects ask:
“Why should I trust you?”
Instead of vague claims (“industry-leading,” “cutting-edge”), offer clear proof:
• Competition: Mention what they’re already using or what else they’ve tried.
• Your USP: Clearly explain what makes you different or better.
• Social Proof: Share real results you’ve delivered for similar customers.
Example:
❌ “We’re an award-winning analytics company.”
✅ “We made [Similar Company] reduce reporting time from 5 days to 2 days, saving them 15+ hours per week.”
3. Why ACT? (Compelling offer)
Finally, prospects wonder:
“What’s the immediate benefit for me?”
Your offer should be tangible, clear, and instantly valuable. It should trigger genuine curiosity or urgency:
• Ideal outcome: Clearly explain the immediate benefit they’ll receive.
• No-brainer offer: Offer something easy to accept that provides quick value.
• Immediate reciprocity: Give first to lower the barrier to action.
Strong offers typically help prospects:
• Save time (quick demo video, actionable checklist).
• Save money (free audit, custom report).
• Make more money (actionable resource or strategy).
Example:
❌ “Open to discuss?”
✅ “I put together a short video on how [Similar Company] cut data costs by 25%. Here’s the link.”
In an upcoming edition, we’ll look into how to make your entire message immediately valuable, using Jordan Crawford’s ‘Permissionless Value Prop’ concept: creating outreach so useful your prospects would even pay to receive it.
Bringing It All Together
When your message answers these 3 WHYs, you’re no longer just hoping the prospect cares. You’ve created pure relevance, clear credibility, and an irresistible offer; all the ingredients of outreach that actually works.
Here’s what that can look like together in one simple message:
“I see you recently hired two new data analysts - usually a sign reporting is becoming a headache. We made [Similar Company] cut reporting time by 60%, saving their team 15 hours weekly. I’ve created a short video showing exactly how they did it. You can watch it here.”
The best messages build on these three WHYs. They work together to tell the prospect’s story and give them a reason to act.
Here’s an example of a cold email that matched it all:
This email copy was part of a campaign that hit a 7% positive reply rate, which is exceptional. But again, reply rates alone aren’t the real goal; they’re just the default metric for most sales platforms. In the next edition, we’ll explore better ways to track meaningful engagement, like the specific actions your prospects actually take.
2. The form of your message: copy formatting 🗞️
Now that we’ve nailed down the core message content, let’s make sure our message visually stands out. Formatting impacts how quickly prospects grasp your message; poor formatting can ruin great content.
Your prospects get flooded with outreach every day, and most messages look and feel exactly the same. To stand out visually, follow these simple, human-focused principles:
1. Keep it short and easy to scan
Your prospects rarely read; they scan. Long paragraphs overwhelm, especially on mobile screens. Break your text into short, punchy sentences and short paragraphs.
Example:
❌ “Our company has helped numerous clients dramatically improve their reporting efficiency through automation solutions, significantly reducing the hours they spend weekly.”
✅
“We help data teams automate weekly reporting.
Saves them 15+ hours every week.”
Clear, short lines are easier to digest at a glance.
2. One clear question or CTA
A common mistake is burying your main request or asking multiple questions at once. This only confuses the reader. Stick to one clear CTA per message, making it easy for your prospect to respond.
Example:
❌ “Would you be open to scheduling a quick call, or do you want to explore our website first?”
✅ “Want to see the 2-min demo video showing exactly how?”
One question = simple choice.
3. Pattern interrupts
Your message lands alongside many others that look identical. Here are some subtle pattern interrupts that skip the prospect’s ‘mental spam filter’:
• Start sentences lowercase (but don’t overdo it).
• Skip the usual greetings (“Hi,” “Hey”).
• Use informal punctuation like dashes or ellipses.
Example:
❌ “Hi Sarah, I hope you’re doing well.”
✅ “Sarah - something about your latest analyst hire tells me…”
These small tweaks visually differentiate your message, making it stand out even more.
4. Sound like a human: remove clutter and jargon
Your prospects can smell sales fluff from miles away, and filler words or empty phrases only make it worse. Stuff like:
• “Hope you’re well.”
• “I know you’re busy.”
• “Circling back.”
just screams generic sales email.
Also, avoid jargon or buzzwords; they’re exhausting to read and feel fake. Instead, write how a normal person would talk: casual, clear, and real.
Quick example:
❌ “Just circling back quickly regarding our industry-leading AI solution…”
✅ “Looks like your analysts spend hours on manual reports.”
Keep it human, simple, and to the point. Your prospects will appreciate the clarity.
Formatting In Action
Here’s a quick example of an email formatted exactly as we’ve discussed:
It’s visually easy to scan, clearly structured, and immediately understandable: precisely formatted to trigger action.
Want help keeping your copy clear and engaging? Try these tools:
• Lavender: Real-time email coaching Chrome extension to sharpen your cold email clarity.
• Twain.ai: Chrome extension that helps you craft compelling copy for emails and LinkedIn outreach.
• ChatGPT / Claude: Use smart prompts to turn these frameworks into your personal outbound writing assistant.
Test and Adapt: Your Market Decides 🧑🏼🔬
Everyone has an opinion about what makes a “good” cold email or DM. LinkedIn is full of sales leaders roasting the bad ones or praising a clever personalized message that made them smile.
The problem? They’re looking at these messages as sellers, not as buyers.
The reality is, there’s no one-size-fits-all formula. What resonates with enterprise VPs might completely flop with SMB founders. “Best practices” can get you started, but your audience’s reactions will tell you what really works.
Here’s how to test and learn:
• Start small: Draft your message using the 3 WHYs framework.
• Test quickly: Send it to a small group and track real results (meetings booked, responses, actions taken).
• Adjust often: Refine your approach based on actual feedback from prospects.
• Double down: Once you know what works, scale it up and cut anything that falls flat.
In the end, your prospects have the final say so listen closely and adapt fast.
Quick Exercise 📝
Let’s put what we’ve covered into practice with a quick, practical exercise.
Take the last 5 messages you sent and ask yourself:
• Did they answer all three WHYs (Why Them, Why You, Why Act)?
• Were they specific and clear, not vague or generic?
• Did they spark an action or response?
Now, pick one of these messages, rewrite it manually using the framework, and send it out today.
Notice how the engagement compares to before. Even small changes can reveal where you need to sharpen your outreach.
Feel free to send it over to me if you’d like feedback.
Wrapping It Up
Great outbound messaging wins when you make prospects feel understood.
When your message clearly explains why you’re reaching out, demonstrates real credibility, and offers immediate, tangible value, prospects naturally engage.
Forget about chasing reply rates. Focus on messaging that sparks curiosity, feels relevant, and drives real action.
Your prospects are busy humans. Respect their time by being clear, relevant, and direct. Do this consistently, and your outbound turns from ignored noise into actual conversations.
Next week, we’ll dive deeper into crafting effective copy for email campaigns specifically, using these fundamentals. Stay tuned!
Until then,
Jasper
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