Lessons from Follow-Ups, Flops & Funny Replies

An ode to the chaos (and comedy) of cold outreach

Have you ever stared at your screen after hitting “Send” on a perfectly crafted follow-up email… only to get a response that feels like it came from a parallel universe? Or worse, radio silence so intense, you start wondering if your email went into the abyss of the internet?

This week, we’re diving into the realest part of outreach life: the awkward, unexpected, and occasionally laugh-out-loud moments that come from trying to connect with strangers on the internet.

Because let’s be honest, behind every pipeline, sequence, or “Hey, just checking in!” lies a human moment. Sometimes it’s a win. Sometimes it’s a flop. And sometimes… it’s so funny, all you can do is laugh and forward it to a teammate with the subject line: “You won’t believe this one.”

Lesson 1: Timing is everything (but also, nothing)

You can optimise your send times, A/B test subject lines, and still… get a reply like:

“Hi. I’m on maternity leave. The baby is three now.”

(Yes, that happened.)

Sometimes our follow-ups land at the worst possible moment. A CEO going through a merger. A Talent Manager mid-sabbatical. Or someone who simply forgot your email existed and responds a year later like nothing ever happened.

Lesson: Don’t take silence personally. People are people, and inboxes are chaos. Always follow up with empathy, and a bit of humour never hurts.

Lesson 2: The “funny reply” genre is alive and well

Here are some actual cold outreach replies I’ve received (names changed, of course):

• “Please remove me from your life.”
• “Are you AI?”
• “This is the third time you’ve emailed me. I'm impressed by your persistence and scared of your follow-up game.”
• “This is the best sales email I’ve ever ignored.”

And my personal favourite:

• “You know what? You’ve earned a meeting. Let’s do this.”

Lesson: Being human in your emails works. Humour, honesty, and authenticity stand out in the sea of corporate sameness. Embrace your inner chaos.

Lesson 3: The flop is part of the process

Let’s normalise the flop.

You can be strategic, polite, and patient and still get unsubscribed, ghosted, or left on “seen.” Cold outreach is not a science. It’s a game of timing, tone, and trial by fire.

One time, I sent a well-researched, hyper-personalised email to a Head of Talent, only to get this reply:

“Not interested. But good hustle.”

Cool, cool, cool.

Lesson: A no is not a reflection of your worth. It’s just a detour. Every flop is still a step forward, plus, you get some great stories for newsletters like this.

Lesson 4: When in doubt, add value (and vibes)

Want a better reply rate? Make your emails actually worth reading. Add:

• Insight. What are they missing out on?
• Relevance. Why them, why now?
• Personality. Because no one needs another “just checking in” robot.

And if all else fails? Sign off with something like, “P.S. I’ll trade you a meeting for a good meme.”

Lesson: Outreach is marketing. You’re not just selling a demo; you’re making an impression. Make it memorable.

Final Thought: Follow-up isn’t desperate. It’s disciplined.

To my fellow sales warriors, growth hackers, and inbox gladiators, keep going. Every weird reply, silent inbox, or accidental “I’ll circle back” moment is part of the journey.

Celebrate the wins. Laugh at the chaos. Learn from the rest. And if you're ever doubting your efforts, just remember:

If you feel like your emails are going into the Upside Down, just know you’re not alone. Stranger things have happened.

Until next time...

Thanks for being part of the Coffee, Calls, and Chaos crew.

Until next time, may your coffee be strong, your calls be short, and your follow-ups be fruitful.

— Skye 💜 Sales human. Inbox wrangler. Chaos coordinator.