5 tips for writing your Messaging Madness email

What does a great cold email look like? Before you enter Messaging Madness 2025, here are my 5 tips on getting it right.

Messaging Madness is about writing a great email. The crowd decides the champion. Whoever wins moves on. Whoever loses goes home.

But this isn't just about writing any email—it’s about writing an email that stands out, gets attention, and starts conversations.

Follow these 5 tips to give your email the best shot at surviving all six rounds and being crowned the Messaging Madness Champion 2025.

1. Start with a strong subject line

Cold emails are the perfect assist to starting conversations, but if no one opens yours, the play is dead before it starts. A great subject line should spark curiosity, set expectations, and be relevant to the recipient.

Use the information provided in the scenarios to frame your subject lines.

What works

• Personalized subject lines: Mentioning a key detail about the recipient’s company or industry.
• Curiosity-driven lines: Creating intrigue without being clickbaity.
  Example: “A challenge your competitors are solving differently.”
• Be natural: Write a subject line that fits into the inbox.
  Example: “What are your thoughts on Lattice’s update?”
• Straightforward and value-driven: Clearly stating the purpose.
  Example: “Cut payroll costs by 20%—without changing software.”

What to avoid

• Generic openers: “Quick question” or “Can I help you?” lacks differentiation.
• Overused tactics: Excessive urgency (“act now!”) or vague statements.
• Spam triggers: Avoid mentioning money, offers, or other spam words.
• Misleading hooks: If the subject doesn’t match the content, you’ll lose credibility fast.

2. Meaningful personalization

How many emails do you receive that mention the obvious - like your job title - or haven’t populated the personalization field of the email (i.e., “Hi, [NAME]”), or simply use the wrong name at all? 

A relevant, engaging email is a slam-dunk for prospects. But if it feels like a copy-paste job, it’s an instant turnover. Great cold emails go beyond first-name personalization. 

How to personalize effectively

• Reference a specific detail: Mention their company’s recent announcement, a competitor’s strategy, or a challenge they likely face.
• Align with their role: Clarify why this email is relevant to their job and priorities.
• Use insights over placeholders: Instead of just inserting a name, write an opening line that shows you’ve done your homework.

Example:

“Hi [name], I saw your team is heading out to the mid-west market. Many COOs struggle to align OKRs across new teams—here’s how we help leaders like you stay ahead.”

3. Be irresistible

A great cold email is a lay-up for a great conversation. But, if your offer isn’t clear or compelling, no one’s making the shot.

How to make your offer relevant

• Tie it to a specific outcome: Example: “We help law firms cut CRM costs by 30% while improving efficiency.”
• Minimize friction: Make it easy to say yes with a low-commitment ask (e.g., a quick chat, free resource, or exclusive event invite).
• Make it timely: If your offer aligns with an industry shift or competitive change, highlight that urgency.

4. Respect your recipient’s time

A cold email has a shot clock. If your email has any element that feels like an unwarranted sales pitch, you’ll lose your recipient instantly.  

Adding trust signals to your email makes it more likely to get a response and shows you respect every second of the recipient’s time.

Ways to build credibility

• Reference customers or competitors: “Companies like [industry leader] use this approach to double response rates.”
• Use numbers where possible: Hard stats are more compelling than general claims.
• Mention relevant expertise: “After working with 50+ saas founders, I’ve seen this common mistake in outreach.”

Example:

“We recently helped a B2B eCommerce startup increase conversions by 43% using a strategy that Shopify doesn’t tell eCommerce companies about. Here’s how it works…”

5. Keep it readable and actionable

While our research doesn’t indicate that length has a negative or positive impact on success rates, what does matter is that you do all in your power to make copy readable.

How to format for readability

• Keep your paragraphs short (1-3 sentences max).
• Use bullet points when explaining benefits.
• Use Grammarly to check your spelling and grammar
• End it with a clear call-to-action (CTA).

Your CTA should be easy to act on. Instead of “Let me know if you’re interested,” you should try: “Would a quick 15-minute chat next Thursday work to go over this?”

Will you be the one in 64?

We’ve all received plenty of bad emails. Messaging Madness is your opportunity to put that right. 

Using the scenarios, bracketology, and the 5 tips I’ve shared in this blog, you’ve got all the inspiration needed to enter Messaging Madness before March 13.

The only question left: will you go all the way and become our Messaging Madness 2025 Champion? Make a copy of this document, choose your scenario, write your copy, and submit your entry via this form:

Good luck!