Feel like a prospect reply should be a win, but the thread still somehow dies a few emails later? When reps stop asking questions, the back and forth slows down, and curiosity gives way to polite endings that never reach a calendar invite.
Take a moment to see how a few well placed questions can keep momentum alive.
Your Conversations Are Dying! Here Is How To Convert Replies To Meetings đź’¬
Published: December 15, 2025
Most sales teams lose deals not because prospects vanish, but because email threads stall when reps stop asking questions and email velocity drops. Lavender breaks down Gong data showing that the number of back and forth emails is the strongest predictor of wins, then explains why curiosity and asking 2 to 4 questions per reply keep conversations alive.
Upside: Curious, question led replies reveal buying process, hidden objections, and who actually makes decisions, so every response moves the deal forward instead of closing the loop. The post also shares plug and play reply templates for “not interested,” delegation, and scheduling that you can drop into sequences to turn more replies into meetings.
Impact: Treat every reply as the start of discovery. You will see more multi threaded conversations, stronger meetings, and fewer deals quietly dying in the inbox. In 2025, the real leverage is not just getting replies, but asking better follow up questions once you have them.
Lands’ End’s “Ends Tonight” Emails Trigger Legal Scrutiny ⚖️
Published: December 15, 2025
ClassAction.org is investigating Lands’ End for allegedly deceptive “limited time” sales emails that kept getting extended, targeting shoppers in Washington, Maryland, and Indiana. Affected customers are being invited into a mass arbitration effort that could unlock claims of roughly $500 or more per person under state consumer protection and email laws.
Upside: Tighten urgency language and make sure end dates match reality, not wishful thinking. Clean up promotional calendars, subject lines, and resend logic now to avoid the gray zone between smart marketing and illegal “fake deadline” pressure tactics.
Impact: Expect more legal action and press around misleading subject lines as regulators and plaintiff firms zero in on email as a high volume channel. Teams that keep promos honest and documented will reduce legal risk and build more durable trust with subscribers who are already skeptical of constant “last chance” offers.
Cold Email, CX, and Why You Cannot Automate Caring 🎧
Watch the full episode here »
Published: July 24, 2025
On this episode of CX Without the BS, I sit down with Brian Nichols to unpack why customer experience starts with the very first cold email, not the support ticket. We cover deliverability, list quality, and copy that respects the recipient, and why confusing pricing, hard to buy offers, and lazy automation ruin trust before a prospect becomes a customer.
Upside: Use this blueprint to make outbound feel like the start of a great partnership instead of a spam blast. Align your cold email motion with the experience you want customers to have later so first touch, sales process, and customer success feel consistent and human.
Impact: You cannot automate your way out of caring, even with the best AI and tools. Teams that treat cold email as a relationship channel, protect their domains, keep pricing simple, and write like a human will book more meetings, close better fits, and build customer experiences that feel honest from the first send.
My Last $.02
Email threads do not usually fail from silence. They fail from lost velocity and shallow follow up. When you ask two to four thoughtful questions, you learn the buying process, surface objections, and find the real decision makers without forcing it.
The meeting often comes from the next question, not the first reply.
Until next time, happy emailing!
Adam