Over the past 7–8 years, I must have sent hundreds of emails and LinkedIn messages to prospects, hoping to arrange meetings to introduce my services.

Here’s a golden rule I’ve learned: Almost all such attempts will fail to elicit a positive response.

There are two key exceptions:

1. You know the person already, and there’s trust and rapport. This is clearly the ideal case. People buy from people they know — and from people they like, remember?

This also includes people you’ve come to “know” online over time — by consistently publishing valuable content, engaging thoughtfully, and commenting on each other’s posts. That kind of digital familiarity can make you feel less like a stranger. (More on this below.)

That said, there’s a flip side: If the person knows you too well, they may worry their professional judgment will be questioned if they recommend you to their employer. Familiarity can sometimes bring hesitation.

2. You don’t know the person, but your message is personalised, timely, and relevant. Here’s an example:

You come across a CEO’s interview in a newspaper. You take the time to read it — and then reference something they said in a thoughtful, relevant message. For instance:

Dear CEO,

I read your recent interview in the FT and found your comments on the lack of long-term engagement among lawyers in Cyprus very insightful. You highlighted how large Fintech companies offering triple salaries are drawing away young legal talent from law firms — a real challenge.

I see the same trend in my consulting and coaching work. I’d love to get together for a coffee to exchange thoughts and explore any potential for mutually beneficial collaboration.

If this is of interest, let me know your general availability over the next two weeks.

Philippos

Based on my experience, this kind of outreach significantly increases your chances of getting noticed. Why? Because it shows effort, understanding, and a genuine reason for connecting.

A few more things that help turn you from an unknown into a known quantity:

• A reputable, consistent, and relevant presence on social media

• An up-to-date website

• Regular content sharing (especially on LinkedIn), which might already be familiar to your recipient

• Having worked with other respected firms in their sector — this boosts your credibility and makes them more likely to engage

What about you, dear reader?

Do you have tips that have worked for your own outreach?

I’d love to hear them.

— Philippos