Appointment Setting Tips Cold Email Outreach

How to Write Cold Emails That Actually Get Appointments

When Ray Tomlinson made his first attempt at “something like QWERTYUIOP”, little did he know that it will pave the way for something more. More meaningful connections, half a century later.

Ray sent the first email in 1971.

Over the past months, we have sent over 20,000 cold emails to several CEOs.

Our goal was to start a meaningful conversation with them.

Cold emails helped us get over 1,000 appointments with some of the CEOs we truly admire.

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One size does not fit all

I know cold email makes us cringe.

Especially when you think about the estimated 205 billion emails that are sent and received each day.

But an effective cold email can help you make meaningful connections with potential partners and customers.

And I found that there is never one script that works all the time for everyone.

The cold email you send to a Principal of a Daycare in Brooklyn will be different from the one you send to the CFO of a Credit Union in Alabama.

Here are five important things I learned in the process of connecting and getting appointments with CEOs through cold emails.


1) Vulnerability

Vulnerability means showing you don’t know everything about the CEO and her business.

This is counter-intuitive, especially for some of us driven by large egos.

True, cold emails thrive on assumptions.

Assumptions that the recipient may have a challenge or problem or goal because her company does XYZ. Often, our assumptions may be completely false.

That’s where the subtle power of vulnerability comes in.

A cold email that shows that you might have wrong assumptions is a powerful way of starting a meaningful conversation.

Michael Simmons talks about this in his Harvard Business Review article, “To Create a Real Connection, Show Vulnerability“:

“Only presenting an idealized version of ourselves separates us from others. The mistaken assumption is that if people find out who we really are underneath, they’d remove themselves from our lives.”

By showing vulnerability, you’re “replacing professional distance and cool with uncertainty, risk, and emotional exposure,” as vulnerability expert Brené Brown describes.

How do you show vulnerability in your cold email?

Here are a few phrases to consider:

  • “I don’t know if you’re looking for new information or ideas on [topic/service/etc] but…”
  • “I’m not sure if it’s a good timing…”
  • “I could be totally wrong on this…”
  • “Does [next step/value proposition] sound fair?”

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2) Credibility

Remember the last time you were at a party with dozens of people?

Regardless of all the music and chatting and noise in the background, you were still able to hear and understand your friends speaking in front of you.

Psychologists call this The Cocktail Party Effect.

This is the tendency to selectively pay attention to what we are familiar with.

The everyday avalanche of email distractions means that business leaders have become wary of emails. Especially the ones from strangers.

Therefore, to get CEOs to pay attention to your email, we must focus on what is credible and familiar to them.

The main way of demonstrating credibility is by using relevant names and numbers.

  • Mention the name of the common friend (if it is a referral)
  • Mention specific names of relevant companies your product has helped
  • Mention names of other CEOs who use your product
  • Quantify a relevant result you’ve helped a CEO get recently

Credibility thrives on specificity.

Be as specific as you can when referring to a name or number.


3) Readability

Some time ago, I had a brainstorming session with a team leader in Oslo.

At some point during that session, I used the word “coveted” to describe the potential market.

I must have said something like “This is a coveted target market”.

The team leader stopped the session and asked me never to use that word again.

It was weird. He might have felt intimated. I don’t know.

But I was totally at fault. It was stupid of me. That experience taught me something really important.

Communication is about clarity, not complexity.

Readability is about clarity, especially when it’s email. Clarity is when we sound conversational. And part how we sound human is writing like one.

No ‘big’ words.

No complicated sentences.

No unnecessary jargons.  

No poor grammar.

There are several online tools that can help you make sentences simple and readable. Examples are Hemingway App, Grammarly and  Readable.  

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4) Length

If you think you can sell a product in a cold email to a CEO, you’re missing the point.

Our foremost aim is to get a response. And then an appointment.


That’s the only way to start a meaningful conversation.

Understanding this goal is important to the length of your email.

It is tempting for long cold emails (100+ words) to be sender-centric. And tiring to read.

CEOs are truly busy. Make their lives easier. Go straight to the point. Keep it short and sweet!

How short is short and sweet?

We’ve found that 60 – 70-word emails (compared this to 100+ word emails) got more responses. Use this more of a precaution than a cast-in-stone rule. Every situation is different.

And while you’re at it, aim for maximum 2 lines in your paragraphs. Spaces create clarity.


5) Request

A Request is your call to action. What direct action do you want the CEO to take if they care about your message?

Here are some types of call to actions:

  • To get a meeting/call
  • To get an answer to a question (Yes or No)
  • To invite to speak at an event
  • To share information (no need for reply)

Your call-to-action should not be weak.

A weak request is not specific, difficult to respond to (because it will take time) and places too much responsibility on the recipient.

A strong request, suggests you respect their time.

Examples of strong call-to-action:

  • Can we chat more about this next week Friday 2 pm?
  • Do you have 40 minutes time to speak at our 10,000 attendee-conference on November 2 in New York?

Use these ideas to improve your cold emails and make your connections with CEOs better.

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