#OS23: Time to Rethink your Cold Email Strategy

Cold emails have become outdated and ineffective. If you’re sending hundreds of generic emails each week, hoping for engagement, you're playing a losing game.

Prospects today aren’t interested in what you’re selling because they don’t know you, trust you, or care about your pitch. Flooding their inboxes with impersonal emails asking for meetings or calls is an outdated strategy. It’s time to rethink how you approach cold emails.

Why Traditional Cold Emails Fail

Most cold emails miss the mark because they’re all about you, not the prospect. When your main goal is to get something from the recipient—a meeting, call, or demo—you’re already setting yourself up for failure.

Stop Sending “Love Letters” ??

Sales emails often sound desperate: “I’d love 15 minutes of your time,” or “We’d love to work with you.” But the truth is, your prospect doesn’t care what you’d love. They don’t know you, and they certainly aren’t waiting to hear your pitch.

These “love letters” don’t fool anyone; they are obvious attempts to get something without offering anything of value in return.

People Aren’t Waiting for You

When prospects have a need, they don’t sit around waiting for cold emails to solve their problems. They do their own research—watching videos, reading blogs, and asking peers for advice. By the time they speak to a salesperson, they usually already know what they need.

Your cold email won’t magically make them care. Instead, you need to create interest.

Cold Emails Are About Creating Interest, Not Finding It

If your strategy is based on hunting for prospects who might be interested, you’re doing it wrong. Prospects don’t need salespeople to tell them about solutions anymore—they can find that information on their own. The focus now should be on creating interest.

Skip the Commercial

If you’re sending emails that are just glorified elevator pitches, you’re not creating interest—you’re contributing to the noise. Your cold emails shouldn’t be commercials for your product. Instead, they should be about building a human connection.

Conversations Create Interest

The best cold emails spark curiosity. They make the recipient think, “This person gets me.” Real interest comes from conversations, not pitches. Ask yourself, “How can I start a meaningful conversation?” instead of “How can I get them to book a meeting?”

Why Quantity Is Your Enemy

Salespeople are often obsessed with quantity: more leads, more emails, more activity. But the truth is, quantity can be your enemy in cold outreach. Sending more emails doesn’t guarantee more success if they’re low-quality and irrelevant.

Focus on Quality, Not Cadence

Flooding inboxes with frequent but poorly crafted emails is a sure way to get ignored. Sending emails often might give you a false sense of productivity, but quality matters more than cadence. Craft thoughtful, intentional messages that show you understand your prospects and their pain points.

Connection Trumps Frequency

If your prospect feels like they’re just another name in your sequence, they’ll tune out. Automation can’t solve this for you. Instead of trying to win with sheer volume, focus on building genuine connections. It’s not about how many emails you send, but whether your emails actually matter to the recipient.

From Cold Emails to Real Conversations

The goal isn’t just to book meetings—it’s to start real conversations. Prospects aren’t looking to be sold to; they want to be understood. Cold emails that spark meaningful conversations focus on the prospect’s world, not your product.

Meetings are formal and structured—something most prospects try to avoid. But conversations are where real progress happens. They turn strangers into prospects who care about what you have to say. Focus on fostering conversations, and you’ll build better relationships.

The Future of Cold Emails: Human-Centered Outreach

The future of cold outreach isn’t about automation or volume. It’s about building relationships through authentic, human connections.

Be Empathetic

Cold emails that succeed start by recognizing that the person on the other end of the email is a real human with real challenges. Empathy is what makes you stand out. Approach your outreach from a place of understanding, and your message will resonate.

Lead with Value

Don’t ask for something right away—offer something of value first. Share insights, provide useful information, or acknowledge a challenge they’re facing. Offering value builds trust and shows that you care about their success, not just your own.

Helpful Resources?

LinkedIn post of the week

Tushar Dey points this out in his Linkedin post. The more targeted and hyper-personalized emails, the more you connect. Check the post now.?

Podcast of the week

In this podcast, Jack and Jeremy dissect a cold email and explore what made this email so effective. They analyze its personalization and strategic content, and share insights on how to elevate cold outreach practices. Spotify | Apple

YT video of the week

In this YT video on email writing, Michael Maximoff is in conversation with Jen Allen-Knuth founder of DemandJen and renowned sales trainer and keynote speaker. She discusses with how she used authentic writing, data-driven insights, and a focus on problem solving to transform her career and empower sales teams around the world.

Rethink your cold email strategy

Cold emails are here to stay, but the way we send them needs to change. It’s time to stop relying on automation and cadence-driven strategies. Instead, focus on human connections, lead with value, and build trust.

Cold outreach is a skill, not a numbers game. The key isn’t how many emails you send—it’s how well you can connect with the person on the other side. So rethink your approach and start crafting emails that spark real conversations.

That's all for today. Hope you learned something new or found something useful here.

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Until next time,

Happy emailing!

[This topic first appeared on Salesgear blog]