The Art of the?Ask

Be effective with cold messaging and actually get useful responses!

LinkedIn provides endless opportunities to network, learn, and get help from people across the world?—?it’s all just a message away! But, do you find yourself sending many messages but rarely receiving a useful response? Then this is a post for you.

This week, I posted a job opening calling for referrals?—?only to receive over 500 messages across my linkedIn, email and whatsApp. I did read every message (whew!) and my observations (and exasperations) inspire this post dissecting what makes a cold message successful.

People want to help, you have to make it easy for them to help you.

No Hello

Unless you’re a friend, please don’t bother with random chit-chat. Especially, don’t just drop a hello and leave the receiver hanging. I rarely respond to an astray hello and I think it’s impolite to send one. Set the context in the first message itself?—?who are you and what are you expecting?

Know your?audience

Why are you contacting them? Are they the right person to help?

Before reaching out, try to learn as much as you can about the person you’re contacting. This will allow you to tailor your message to their interests and show that you’ve put in the time and effort to understand them. Your message should demonstrate a genuine interest in the recipient and their work, not just be a platform to talk about yourself.

Ask the?“ask”

What do you want from them?

Briefly explain why you’re reaching out. Is it for career advice, a potential collaboration, or an introduction to someone in their network? Are you requesting a 15-minute call, feedback on your work, or simply seeking their expert opinion on a specific topic?

What would you like to discuss??—?Give an overview of your questions.

Don’t be superfluous

Less is more.

A formal tone and corporate vocabulary may look impressive on paper, but they also encourage people to start skimming and stop processing. Talk like you would, as a human in real life and don’t sound like ChatGPT.

Blaise Pascal famously wrote, “If I had more time, I’d write a shorter letter.” Prefer brevity over jargon to keep reader fatigue at bay. Respect your reader’s time and get to the point, providing only the context that is relevant.

Help the?helper

Give them all the needed context in easily consumable form. Structure your message with all the relevant information easily accessible. If you’re asking for career advice, instead of just dropping your resume, add quick bullets of what you’ve done. Instead of just asking for guidance on a question, tell them what you’ve done so far to solve the problem. When asking for a resume review, share it as a drive link with comment access enabled instead of an attachment. Lean towards asking questions that are easier to answer.

It’s a two way?street

Remember, it’s about building a connection, not just getting what you want.

Find a way to be useful. For example, be fun and interesting to talk to, or help them in some way. Think about it as building a relationship, rather than just receiving favor. Let your message communicate that.

Do your?homework

Do your research! Don’t ask anything that’s easy to google, use the opportunity of a 1:1 interaction to ask deeper questions.

When you’re asking for help, check if the person you’re messaging is the right person for this. When you’re asking for a referral, check if you qualify the minimum requirements.

Respect

Treat them and their time with value.

Even though the internet makes it incredibly easy to send messages, remember there’s a person at the other side of the channel.

If you’re meeting someone in real life?—?would you ever regurgitate the exact same thing you spoke about to someone else or would you contextualize it? Similarly, do not send template messages.

Follow the same protocol you would in real life?—?introduce yourself, address the other person with the right name and pronouns and be nice. (No, don’t call the person you’re asking for a referral cute in the same message. Don’t try pranks.)

In the end, when messaging someone, your goal should be that the receiver:

• … understands where you are coming from
• … has a clearer understanding of the request and its context
• … feels respected as you took the time to empathize with their values

Crafting the right message is HARD. Spend a genuine effort doing it, but don’t beat yourself too much about it. When you’re confused, you’re probably also confused about what you want, and what would help you. Just hit enter. ??

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