Just ask for what you want

TLDR: don't "ask to ask", just ask for what you want.

ChatGPT-generated illustration accompanying a blog post about being direct in communication rather than asking vague questions ChatGPT: “Generate an image that goes with this blog post”

I have sent many outbound messages to people over the years, with varying degrees of success. Now that I receive a lot of inbound, I have noticed some patterns of what makes me more or less likely to respond.

Therefore, I am begging anyone sending cold outbound on X/LinkedIn/elsewhere:

Do NOT lead with an ambiguous request.

Hi! Would you be up for a quick meeting/coffee chat sometime?

I have taken so many meetings where both our time is wasted because someone

wants to sell a product/recruit where I am the completely wrong ICP
has questions that I can answer trivially over DM
has questions that I am happy to answer but require me to do some preparation/research
has not thought deeply about why we should be on a call together

Similarly, do NOT send 5 separate warmup messages that then requires your recipient to respond to get the full details:

Hi Nick!"
"How are you?"
"We share similar interests"
"Can I ask you a quick question?"
"It's about AI"
"Have you ever had a problem related to <thing>?"
"Anyway, if you do, you should use <product>

This just generates lots of needless back-and-forth and increases the probability that they stop responding at some point.

You’re not Machiavelli

And this isn’t 1500s Florence. Sending purposefully opaque outbound requests reeks of insincerity; it screams “I’m withholding information because it may help me manipulate you into something you wouldn’t do otherwise.”

The manipulative info-withholding strategy is designed for a long iterated game with stable participants who all have something you want. However, cold outbound isn’t like that. You’re playing a single-turn game with a huge number of participants, most of whom can’t help you even if they wanted to.

Throughput beats scheming.

DO directly send one message with all relevant context

Hi Nick, I'm building a <product> that does <thing>, other AI companies <X> and <Y> find this useful, are you interested? <link to learn more>

Likewise, if looking for a job, there's no need to ask "Can I send you my resume?" Just attach your resume.

I promise, this will save us all collectively a lot of time.

PS: this issue has come up often enough that I sometimes link to this page in conversations. If I sent you this link, it's because I want to jump straight to helping you.

Originally posted to LinkedIn on 2024-12-20, revised 2025-07-02