Your requests to “pick your brain” are dying in people’s inboxes.

You’re making the same mistake everyone makes when they’re desperate for a response.

A client sent me his message he’s been trying. Fifteen attempts. Zero responses.

I spotted the problem before I finished reading the first sentence.

Here’s the original message my client wanted to send:

Before:

Hi Name,

I hope this finds you well. I wanted to reach out one final time, as your background particularly resonates with me. The oil industry pivot to tech, combined with our shared interest in thinkers like Jocko and Lex Fridman.

I’ve applied to roles on your team at Google and would greatly value a brief conversation about your transition from oil to tech, if you’re open to it.

No pressure if you’re unable to connect. I completely understand how busy things can get. Either way, I appreciate you taking the time to read this.

Best regards,

Let me break down what’s wrong here:

🎯 1/ Make It About Them, Not You

The biggest mistake? “I’ve applied to roles on your team.”

This shifts the focus to YOUR need (a job) instead of THEIR experience. It also implies “why haven’t you responded to my application?”

✅ Fix: Lead with genuine curiosity about their journey. “I found your profile when researching people who made the pivot from oil to tech.”

Want AI to help? Use ChatGPT or Claude to research the person before you write.

👉 Try this prompt:

“I’m reaching out to [Name] at [Company]. Help me find 2-3 interesting things about their background I can reference. Check their LinkedIn for career transitions, recent posts, or unique experiences. Give me specific details I can mention naturally in my outreach.”

😰 2/ Remove the Fear

“I wanted to reach out one final time” makes them feel guilty before they’ve even decided to respond.

“I hope this finds you well” is stiff and formal. You’re not writing a business letter.

✅ Fix: Start casual. “Hope you’re well” is fine. Skip the guilt trip entirely.

⏱️ 3/ De-Risk the Time Commitment

“A brief conversation” is vague. How brief? 30 minutes? An hour?

People need to know exactly what they’re signing up for.

✅ Fix: Be specific. “Would love a short (15-20m) convo” tells them exactly how much time you need.

📝 4/ Make It Easy

No clear next step. No offer to work around their schedule. No booking link.

You’re making them do all the work to figure out logistics.

✅ Fix: “Happy to send times and work around your schedule” removes friction.

Here’s the rewrite:

After:

Hi Name,

Hope you’re well. I found your LI profile when researching who’s made the pivot from oil to tech. It’s a short list 🙂

(Then I noticed you were also into Jocko and Lex Friedman. And knew I had to reach out, ha.)

If you have the bandwidth, would love a short (15-20m) convo on how you made that oil to tech transition. Happy to send times and work around your schedule.

If you don’t have time right now, no worries at all.

Thanks,

What changed:

• Casual, not formal

• About their experience, not your job search

• Specific time commitment (15-20m)

• Easy to say yes (or no)

• Shows genuine research (oil to tech pivot, shared interests)

👉 Use this prompt before sending any message:

“I’m sharing a cold email I wrote to ask someone for an informational chat. Your job is to evaluate how personalized, thoughtful, and low-pressure the message feels.

Step 1: Rate the message on a scale of 1 to 10 for personalization.

Step 2: Analyze it across these 5 factors:

1. Relevance (Why this person?)

2. Curiosity over asks (Not just fishing for jobs)

3. Tone and human warmth

4. Effort signal

5. Clarity of purpose

Step 3: Suggest 2 specific edits to improve personalization or tone.

Here’s the message: [Insert your message here]”

🔧 Your Action Item

Before you send your next outreach message, run this 4-point check:

1. Is this about learning from THEM, or asking THEM for help with MY job search?

2. Did I remove stiff, formal language?

3. Did I give a specific time (15-20 minutes)?

4. Did I make it easy to say yes?

If you can’t answer yes to all four, rewrite it.

The goal isn’t to trick people into responding. It’s to show you’re genuinely interested in their story, and make it easy for them to share it with you.