How to Cold Message People on LinkedIn

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Have you ever sent a cold message on LinkedIn to a senior executive? Did you get a reply?

Don’t you wish you knew the right way to message senior executives on LinkedIn?

Last Friday night, I was having dinner with an old secondary school buddy, James. He’s a vice president at a multi-billion dollar private equity fund. It’s an extremely sought after job.

Because the industry is so competitive, it’s impossible to get your application through the HR front door. You need to network your way in.

Unfortunately everyone is in on this open secret. Everyone is try to network their way in. This means that high ranking people like James get a ton of cold messages on LinkedIn from jobseekers.

90% of the messages are complete strangers asking to meet James for coffee.

James of course, ignores every single one of those messages. He’s a busy senior executive at a fund. His workload is heavy enough as it is. He doesn’t have time to entertain coffee chats from complete strangers.

So I asked James – what’s the best way to get the attention of someone like him on LinkedIn?

His answer? – Ask thoughtful questions.

You see, senior people like James love coaching young executives. Mentoring is a very fulfilling role. It’s like raising a child.

James says he loves it when he gets smart questions from jobseekers who’ve obviously done their homework.

One example was for a real estate deal James’ fund completed. The price they paid was about 20% below market value, despite there being many other bidders for the asset.

A young associate, at another fund, cold messaged James asking about the deal. He recognised that the deal was undervalued, and asked if they included a special sell on clause, similar to some other deal recently done by James’ head company in New York.

Funnily enough, that was exactly the structure James’ fund used in this deal. He was impressed by the insight of this young associate. They exchanged a few more thoughtful back and forth messages. With each message, James grew more and more impressed by the intelligence of this associate, and how much homework he was doing on his own. He was obviously committed to being the best in his industry.

A few weeks later, James met this associate for coffee. They hit it off and soon after, James made an offer for this associate to join his company.

That is a textbook example of how to network your way into a highly sought after company.

Step 1: Find your target executive. Ideally a key decision maker. Get their email address
Step 2: Research the firm. Compare them to other firms in their industry. Why is this firm more successful?
Step 3: Come up with thoughtful questions and cold message your target key decision maker
Step 4: If you get a reply, try to keep the conversation going. Continue to engage them with insightful questions
Step 5: Meet them for coffee. Try to leave a good impression. Hopefully you’ll get a job offer.

The job market today is filled with so much noise. They are more talented candidates than ever before, and yet, it’s harder than ever to find the right ones.

Thoughtful networking is my latest trick in getting my clients job offers to roles they could only previously dream of!

If you found this helpful, please forward it to your friends who are currently job hunting. Everyone should learn the right way to network. 🙂


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