Why your DMs aren’t converting (and what to do instead)
Marcus stared at his LinkedIn inbox, the anxiety settling deep in his chest as he read through another unanswered message. Hours spent on the perfect response … pitching his ass off … had once again ended in silence. It was starting to feel personal, like a repeated rejection he couldn't shake.
Frustrated, Marcus switched tabs to LinkedIn's feed, desperate for distraction. His eyes landed on a post from Alex, another career transition consultant he quietly admired:
"Over 70% of my clients transition into full-time entrepreneurship within one year … without formal credentials or traditional career paths. And the best part? It often starts with a single, powerful question."
Marcus hesitated only a moment before typing "Interested" into the comments. His inbox lit up almost instantly:
"Hey Marcus! Glad you reached out! Curious … what's prompting you to explore entrepreneurship right now?"
Marcus blinked, momentarily taken aback. The message felt surprisingly genuine, warm, and casual. No pitch, no elaborate explanations. Just a real question. He replied honestly:
"I've been feeling trapped in the corporate grind. I'm craving something of my own."
Another message from Alex appeared quickly: "Totally relate to that feeling. If you could picture the perfect day in your entrepreneurial life, what's one thing you wouldn't compromise on?"
Marcus paused, picturing clearly for the first time in weeks what mattered most to him: flexibility, meaningful client relationships, the freedom to pursue his passions without someone else's rules. He smiled slightly and typed, "Freedom. Real freedom to work on projects that matter."
Alex responded instantly, "Love that vision. What's held you back from going after it already?"
Marcus sighed, typing slowly, "Honestly, it's fear. Fear of leaving stability behind. Fear of failure."
The reply appeared gently, almost thoughtfully, "Completely normal! Everyone feels that. What if you had a clear, step-by-step plan to reduce those fears and build security as you go … would that make a difference?"
Marcus felt his shoulders relax. It registered instantly how different this felt from theDM conversations he was having. This conversation felt like a conversation with a friend - that actually cares.
He typed back, energized, "That would help immensely."
Alex's message was reassuring: "I help aspiring entrepreneurs develop these roadmaps. Happy to hop on a Zoom and talk about what this could look like for you, if that sounds helpful."
Marcus felt the weight lift from his shoulders. This conversation had nothing to do with pressure or sales tactics … it was just a conversation.
Before he knew, he was replying "Absolutely. When are you available?"
You think DM selling means being pushy. It doesn't.
The truth? Selling in the DM isn’t about pressure… it ‘s about genuine conversation.
The next morning, Marcus revisited his own approach to DM conversations with potential clients for his program. He realized that his previous method … meticulously constructed pitch messages … was creating the very resistance he was trying to avoid.
His breakthrough came when he recognized what Alex had did so effortlessly - created space for genuine conversation through thoughtful questions.
When Marcus reviewed his unsuccessful conversations, he noticed a pattern. He would start with rapport-building, then switch abruptly to "selling mode" when he felt it was time … creating a jarring transition that triggered resistance. His messages became longer, more detailed, and focused on features rather than the person's unique situation.
The new approach was different. No mode-switching at all. Just genuine curiosity that gradually uncovered the perfect fit between a client's needs and his solution.
Over the next month, Marcus applied what he'd learned from his experience with Alex to every DM conversation:
Begin with a single, powerful question about the person's current situation or motivation
Listen carefully and ask follow-up questions that build upon their answers
Create space for them to articulate their own vision and obstacles
Only introduce his program when they expressed a need it specifically addressed
Marcus distilled his insights into three core principles:
Invite People to Share Their Stories: Everyone deeply desires to feel heard and understood. When you ask open-ended questions, you provide space for people to express their thoughts, fears, and hopes. Genuine dialogue fosters clarity and trust far better than any sales pitch.
Connect Authentically: Drop formal scripts and corporate jargon. Speak naturally, openly, and conversationally. Authentic connections build immediate trust, creating a safe environment for honest conversations.
Lead with Curiosity: Replace pitches with curiosity-driven questions. Thoughtful questions help others reflect deeply, guiding them naturally to clarity. When clients reach their own conclusions, decisions become easy and comfortable.
His conversion rate from DM to discovery call jumped from 12% to 37%. The conversations felt more authentic, and prospects were arriving at sales calls already pre-sold on working with him.
Most importantly, he never felt pushy, because he wasn't pushing at all. He was simply being consistently curious, and letting the natural match between their needs and his program reveal itself through conversation.
Your Turn
The Curiosity-First Challenge
Choose 5 prospect who asked for your lead magnet, but the conversation stalled in the DM.
Prepare three powerful questions you can use to restart and continue the conversation i.e. (format for your audience, lead magnet, etc):
"What specifically prompted your interest in this topic right now?"
"What have you already tried to address this challenge?"
"If we solved this perfectly for you, what would that mean for your future?"
Reach out with curiosity: "I noticed you [action they took]. I'm curious - what aspect of [topic] are you most interested in exploring?"
Follow the 3-Question Rule: Ask at least three thoughtful questions before mentioning your services. Let each question build naturally from their previous answer.
Track your results: Notice how the conversation feels different, what surprising information surfaces, and at what point (if any) they express interest in learning more about working with you.
Reply to this email or direct message me with one conversation you tried this with. I'll share some personalized insights.
Prefer listening to reading sometimes? Want an extra layer?
Press play for the ‘Narrated Insights’:
Today’s Mega-Prompt: "DM Re-Engagement Strategy"
Your lead magnet attracted prospects, but now your inbox feels like a graveyard. They wanted your solution… so why aren’t they talking?
Today's mega-prompt gives paid members a simple, repeatable strategy to revive stalled DM conversations with prospects who’ve shown interest but stopped responding. Instead of generic follow-ups, you'll use carefully structured curiosity questions that re-spark genuine dialogue and triple your conversion rate compared to cold outreach.
Paid members get exclusive access to:
✔ 3 customized curiosity questions proven to restart meaningful DM conversations
✔ A structured outreach message template to naturally reopen stalled conversations
✔ A clear tracking system to see which questions generate the highest response rates