How to Create Poke-the-Bear Questions That Get Replies

What Are Poke-the-Bear Questions?

Poke-the-Bear questions target your prospect's hidden pain points—problems they might not even realize they have. Unlike leading questions that feel manipulative, these questions get prospects to think differently about their current situation.

The concept (popularized by cold email expert Josh Braun) is simple: instead of asking if someone wants a solution, you make them question whether their current approach is actually working.

Why Standard Questions Fail

Most cold emails ask predictable questions that prospects have seen hundreds of times:

❌ "Would you be interested in learning more about our solution?"
❌ "Do you need help with [problem]?"
❌ "Can I get 15 minutes on your calendar?"

These questions require zero thought and can be answered with an automatic "no." They fail because they:

• Feel like obvious sales tactics
• Don't create any cognitive dissonance
• Don't make prospects reconsider their status quo

The Poke-the-Bear Framework

To create effective Poke-the-Bear questions, follow this simple framework:

1. Identify the gap: What does your prospect not know that could hurt them?
2. Focus on consequences: What risks are they unknowingly taking?
3. Challenge assumptions: What "truths" are they accepting without question?
4. Ask neutrally: Phrase as a genuine inquiry, not a leading statement

10 Examples That Drive Responses

Here are real Poke-the-Bear questions that have generated positive replies across different industries:

For Sales Teams

"How do you know your SDRs aren't spending 8+ hours weekly on activities your competitors have automated?"

For Marketing Leaders

"How are you measuring if your content actually influences pipeline, or just creates vanity metrics?"

For HR Directors

"What process confirms your top candidates aren't accepting other offers while your approval workflows run?"

For E-commerce

"How do you know which abandoned carts represent actual lost revenue versus normal shopping behavior?"

For SaaS Companies

"What system ensures customers struggling with your product get help before they cancel?"

For Financial Services

"How do you verify your clients aren't keeping assets with competitors that you could be managing?"

For Agencies

"What confirms the leads you're generating actually match your clients' ideal customer profile?"

For Manufacturing

"How do you know your quality control process isn't missing the issues customers care most about?"

For Healthcare

"What verifies your patient follow-up process isn't causing preventable readmissions?"

For Real Estate

"How do you track which properties you've shown aren't selling because of easily fixable issues?"

Implementing in Cold Emails

The perfect placement for a Poke-the-Bear question is after your opening line. For example:

Subject: measurement question

Hi {First_Name},

LinkedIn showed you took over as Marketing Director at {Company} last month. Congrats on the role.

How are you currently determining if your marketing analytics are tracking metrics that actually drive revenue, or just measuring activity?

We've helped companies like {Competitor} connect their marketing data directly to revenue outcomes, increasing attribution accuracy by 37%.

If improving your marketing ROI visibility is a priority this quarter, would sharing our approach be helpful?

Best,
{Your Name}

Common Mistakes to Avoid

❌ Making it accusatory: "Don't you realize your current approach is flawed?"
❌ Being too generic: "How do you know your process is working?"
❌ Using industry jargon: "How are you optimizing your multi-touch attribution paradigm?"
❌ Obvious sales fishing: "Wouldn't you like to save time and money?"

Why This Works: The Psychology

Poke-the-Bear questions work because they:

1. Create cognitive dissonance: They highlight gaps between what prospects believe and reality
2. Trigger loss aversion: They activate the fear of missing something important
3. Build credibility: They position you as an expert who sees what others miss
4. Feel conversational: They read like something a trusted advisor would ask

Testing Your Questions

Before deploying in campaigns, test your Poke-the-Bear questions with these criteria:

1. Does it highlight a risk the prospect hasn't considered?
2. Would it make them pause and think "that's a good question"?
3. Is it specific to their role and industry?
4. Does it avoid feeling like a sales tactic?

If you answer yes to all four, you've created an effective Poke-the-Bear question.

Beyond the First Reply

Once you get a response, don't ruin it by immediately pushing for a meeting. Instead:

1. Acknowledge their answer
2. Provide a brief but valuable insight
3. Ask a follow-up question that deepens the conversation
4. Only then suggest next steps if appropriate

The goal is a conversation, not just a meeting booking.

Start Creating Your Questions

The best Poke-the-Bear questions come from deep industry knowledge. What do you know that your prospects don't? What assumptions are they making that could be hurting them?

Create a list of 5-10 customized questions for your specific audience, test them on a small batch of prospects, and refine based on response rates.

When you hit on the right question, you'll see your response rates jump dramatically—often from below 1% to 3-5% or higher.

Real-World Examples from Our Case Studies

Want to see Poke-the-Bear questions in action? Check out how we've used strategic questioning to drive results:

• Zero-Fee Payment Processor Case Study - See how simple math questions about monthly fees generated 52 meetings
• API Monitoring Platform Case Study - Learn how technical credibility questions resonated with engineering leaders
• Podcast Production Case Study - Discover how creative concept questions stood out from generic pitches

Need more help with your cold email campaigns? Our team has generated over 10,000 positive responses in 2024 alone. Contact us for a free campaign test where we'll validate your offer works before you pay a penny.