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3 Expert Insights About Personalizing Emails (December 2024)

3 Expert Insights About Personalizing Emails (December 2024)
Dec 20, 2024
By:
Joshua Schiefelbein

Get 3 expert insights on what to do and not do for email personalization

4m 55s reading time

Personalization is often seen as the secret to writing better emails and driving results through outreach. 

But here’s the challenge. Bad personalization can feel awkward, irrelevant, or even creepy. 

To avoid this, it’s critical to use personalization strategically. In fact, sometimes knowing when not to personalize is just as important.

Here are 3 expert insights about email personalization.

Beware the dangers of hyper-personalization

Instantly’s Felipe Aranguiz shared an interesting story about hyper-personalization gone wrong.

The email assistant knew where Aranguiz lived and worked, and referenced a commonly used bus number in Belgrade.

But as he states, prospects are pressed for time and they usually don’t care about irrelevant fun facts. Emails that start off with meaningless content waste valuable real estate, and open the door for the recipient to trash the email before they finish.

How you can apply this

Here’s how you can use this in your sales outreach:

  • Don’t force personalization – This can’t be said enough. The only thing worse than no personalization is forced personalization, so don’t use irrelevant or awkward details (a la “I see you visited our website…” 😈)
  • Deliver value immediately and throughout – Your first line needs to provide value, so instead of quirky fun facts, highlight a solution to a pain point or explain the benefit of reading the whole email.
  • Leverage AI for precision, not tricksAI solutions excel at finding data and insights that you can use to improve the relevance of your targeting and messaging. So rather than adding fluff to your sales copy, use AI to spot prospects who are likely to benefit from your offer, then create messages at scale that speak to prospects’ needs. 
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And if you happen to have a fun fact about Belgrade (hopefully not about a bus route), you can share it once you get on a call or sales demo to build rapport.

Fun fact about Belgrade
Belgrade has changed its name at least 15 times throughout its history.

Consider hyper-relevance over hyper-personalization

As Josh Braun states, personalization is the gold standard for cold emails.

But as the first insight showed, hyper-personalization can seem forced and irrelevant. In certain “nightmare-ish” instances, hyper-personalization will come off as creepy.

So instead of forcing personalization, you can consider hyper-relevance. Hyper-relevance is:

  • Highly specific
  • Highly timely
  • Aligned with a narrow audience segment

It’s very similar to segment-based personalization, but instead of each email being limited to one prospect, you can send the same email to many prospects, with the only changes being name, company, and maybe region.

How you can apply this

Here’s how you can build hyper-relevance into your sales outreach:

  • Focus on business value, not personal details – The entire purpose of hyper-relevance is to skip the need for personal details. This saves you from making unnecessary personal references that might cause your message to feel intrusive or forced.
  • Define a narrow target audience – Hyper-relevance works because the audience shares the same traits (industry, company size, location). This allows you to tailor your outreach to speak to the segment’s unique pain without forcing personal details.
  • Simplify your messaging – Your emails should have clear value, actionable insights, and highly relevant content that directly addresses the segment’s challenges. Your prospects will appreciate this.

Start with cliches, then flip them

Here’s a tip from Julian Cole if you’re using generative AI to brainstorm content.

It goes like this:

  1. Ask for common cliches or stereotypes about a certain action.
  2. Ask generative AI to write a paradox that combines the cliche with creative wordplay.

This will also open up interesting statements, provocations, and insights. 

How you can apply this

Here’s an example of this in action. 

Imagine you’re selling an AI SDR and you want to anticipate and creatively address common myths and objections.

Here’s a prompt you can use.

What are 3 negative cliches or stereotypes about AI SDRs?

These are the results we got.

StereotypeExplanation
The Spam MachineAI SDRs are just glorified email blasters, flooding inboxes with irrelevant or generic messages.
The Robotic ToneTheir outreach feels lifeless and scripted, lacking the natural flow of human conversation.
The Job ThiefThey’re supposed to save time, but configuring and maintaining them eats up more hours than they claim to save.

Then you’ll want to follow the previous results with this prompt.

Write 3 paradoxes about the 3 cliches using creative wordplay about the above 

These are the results we got.

StereotypeParadox
The Spam MachineAccused of flooding inboxes with noise, AI SDRs actually thrive on data-driven precision, sending fewer but smarter messages—so who’s really spamming here?
The Robotic ToneAI SDRs promise to humanize outreach but sometimes deliver messages so robotic, they make humans question their humanity.
The Job ThiefFeared as job-stealers, AI SDRs often become a sales rep’s best partner, taking over the grunt work to free up humans for deeper connections.

Feel free to try it out for yourself 🙂Just keep in mind that you probably won’t get the exact same results due to the nature of generative AI and large language models.

Here’s another example using the same prompts, but for Starbucks. Because why not? 😀

StereotypeExplanationParadox
You’re just paying for the brandPeople often joke that Starbucks coffee is overpriced and customers are paying more for the logo than the actual drink.You’re paying for the logo, but it’s the cup you hold that makes you feel seen.
It’s just sugar in a cupA common critique is that Starbucks drinks are overly sweet, making them more like desserts than actual coffee.It’s called coffee, but it’s the sweetness that wakes you up.
Your name will always be spelled wrongThere’s a running joke that Starbucks baristas intentionally misspell names on cups, turning it into a quirky part of the experience.They misspell your name, yet you never feel more identified.

As you can see, you can use generative AI to brainstorm approaches to overcome objections and even address pains.

Though depending on your target audience, you may want to tone down the humor.

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TABLE OF CONTENTS
1. Beware the dangers of hyper-personalization 2. Consider hyper-relevance over hyper-personalization 3. Start with cliches, then flip them
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