Analyzing the question structures that converted to actual meetings revealed these winning formats:
From her direct outreach approach:
We have several connections in common. {{firstName}} How long have you been in the (industry) space?
Why It Works: Uses mutual connections for credibility, keeps it under 15 words, and asks an open-ended question that naturally leads to conversation about their experience and current situation rather than risking a "no" response.
From his startup targeting campaign:
Are you facing any challenges with (painpoint)?
Why It Works: Direct yes/no question that immediately qualifies prospects and sorts leads based on their pain points, making follow-up conversations more targeted.
https://www.youtube.com/watch?v=4geABi-xxCo&list=PLA4t24JzNORE7TmbAcCJfB1ac7ujl5o1-&index=3&t=25s&pp=iAQB
From his typical outreach sequence:
Can I send you over some (information/video/case) study we've created?
Why It Works: Positions the ask as delivering value rather than taking time, while the implied question ("Would this be helpful?") feels consultative rather than sales-heavy.
https://www.youtube.com/watch?v=23575l2W_oI&list=PLA4t24JzNORE7TmbAcCJfB1ac7ujl5o1-&index=4&pp=iAQB
Jeremy Dixon
Jeremy's messages generally start with an intro and end with a call to action. His typical call to action (which implies the question) is:
"Can I send you over some information/video/case study we've created?"
From Greg Hurwitz's recruitment campaign: