Great outreach doesn’t start with your solution; it begins with their problem.
That’s why smart outbound campaigns ask problem questions. When done right, these questions spark interest and position your offer as a natural next step.
What Not to Do
Avoid vague or assumptive questions like:
❌ “Are you struggling with leads?”
❌ “What keeps you up at night?”
❌ “Is your sales team underperforming?”
❌ “Do you want to 10x your business?”
Why do they fail?
Too broad or cliché.
Feels like a setup for a pitch.
Don’t reflect research or personalization.
What to Do Instead
Use specific, relevant questions that reflect an understanding of your prospect’s role or industry.
Examples:
✅ “Are your cold emails getting stuck in spam filters?”
✅ “Is LinkedIn outreach something you’ve tested, or still exploring?”
✅ “Do you already have a system for warming up new domains?”
✅ “How are you currently sourcing verified data for your outbound campaigns?”
Why do they work?
Sounds like a real person, not a sales script
Focus on a clear, common pain point.
Invite a reply without pressure.
How to Use Problem Questions in Outreachly
Add one:
In your first message to spark interest
In a follow-up to restart the conversation
As a manual task prompt before a voicemail or LinkedIn DM
🚀Success! By asking the right kind of problem questions, you're showing you get your prospect and making it easy for them to say yes to the next step.