When to personalize vs. when to stay generic

ideko

Personalization is held up as the ultimate benchmark of a “good” outbound motion. We’re taught that the more you know about your prospect: their name, their company’s funding, their dog’s name; the more effective your message will be.

But this is a dangerous assumption.

At some point, personalization stops being a signal of intent and becomes futile, pointless, and just plain creepy. We’re in a personalization arms race, and the only result is prospects who are numb to it and GTM teams who are investing 50% of their time in a tactic that delivers 5% of the value.

The reality is, personalization has become a cheap tactic. It’s spam with your name on it.

The death of a personalization as a “best practice”

This shift happened for two main reasons:

  1. Personalization is Now a Commodity: It used to be hard to find and use data points at scale. Doing it signaled real, manual effort. Today, with tools like Clay and countless databases and AI agents, personalizing an email with a prospect’s recent funding round, their latest LinkedIn post, or their company’s tech stack is trivial. The ability to personalize beyond the first name has been fully commoditized. Your prospects are drowning in it, and they’re no longer impressed.
  1. It’s a “Distorted Mirror”: Imagine walking into a party, and every stranger who approaches you says, “Hi, I know you raised $32 million in your Series A, and you’re hiring for 12 roles.” It’s not impressive; it’s unsettling. People don’t want to be broadcasted their own details. When every piece of marketing is hyper-personalized, it feels like everyone is holding a small, distorted mirror up to your face. It’s not a conversation starter; it’s an intrusion.

We’ve arrived at this point because we’ve confused intent with SOPs. We’re personalizing because a checklist says we have to, not because we have a genuine, relevant reason to do so.

Personalization is no longer clever, its creepy

When you try too hard to be personal, you run straight into the wall of edge cases. Recently, I was scrolling through Instagram and a marketer, bored with Stanley’s “irrelevant” emails, designed a “better” version. The concept was “stay hydrated, queens,” and the email was visually fantastic. But a corporate employee immediately pointed out the flaw: “This is too much work to segment, and what if someone receives this and feels misgendered? In this political environment, that’s a huge risk.”

That employee wasn’t wrong. When you try to get “personal” with people you don’t actually know, you’re making assumptions. And at scale, some of those assumptions will be wrong, leading to negative publicity that may far outweigh the cleverness of the campaign.

relevance > personalization

I’ve studied the work of some of the sharpest minds in the GTM outbound space space including Eric Nowoslawski, Jordan Crawford, and Tim Yakubbson. When you see examples of their best-performing campaigns, a startling pattern emerges: many of them have little to no personalization.

They might use a first name. That’s it.

They aren’t “personal.” They are relevant.

There is a profound difference.

  • Personalization is: “I saw you’re a dog person,” or even “I saw you’re hiring 10 SDRs.” It’s an observation that proves you’re watching, not that you understand.
  • Relevance is: “Most VPs of Sales who are rapidly scaling an SDR team find their old playbooks and spreadsheets break. The challenge isn’t just hiring; it’s building a system that can ramp 10 reps at once without the wheels falling off.”

The second example is aimed at the exact same person, but it never states the personal data point. It doesn’t say “I see you…” It demonstrates a deep understanding of the problem that is common to their role and situation. The prospect sees their problem in your message and feels understood, not observed.

The best-performing messages don’t need to be personal. They just need to be so relevant to the person’s problem that it cuts through all the noise. If you’re spending 10 or 20% of your time trying to figure out things like if a prospect is a “cat person or a dog person,” it’s a massive red flag.

If your message feels empty and insubstantial without that personal gimmick, your core message is the problem. You need to go back to square one.

4 tests to check if personalization is hurting your cold emails and DMs

So, how do you know when to stay generic? Use these tests before you hit “send.”

  1. Is it personalized for the person or the role?

This is the most important rule. You aren’t reaching out to “Sarah, the dog lover.” You are reaching out to “The VP of Marketing at a Series B company.” Your message should be hyper-relevant to the challenges of that chair. What problems does that role face in that specific context? That’s all the relevance you need.

  1. The “in-person slap” test

Ask yourself: “If I said this to the person at a conference, would I get slapped for being creepy?”

  • “Hi, I see your company just raised $30M.” -> Fine. Public info.
  • “Hi, I see you just posted on Instagram about your vacation.” -> Creepy.
  • “Hi, I saw you like golden retrievers.” -> Very creepy.
  1. Utility test

Ask: “Does telling the person this piece of information do anything positive for their consideration of my offer?”

  • Does knowing you researched their funding round make your product better? No.
  • Does it improve the logistics of the deal? No.
  • Does it prove you understand their problem? Maybe, if you can connect it. But usually, it just proves you have a data tool.

If the “personal” detail doesn’t serve the prospect, it only serves your ego.

  1. The substantiality test

Delete all the personalization fields from your message. Does it still stand on its own? Does it still clearly articulate a problem and a solution for the role you’re targeting? If not, the personalization was just a crutch for a weak value proposition.

Personalization isn’t the goal. It’s a tactic and an increasingly overused and low-impact one. Stop trying to show people you know them. Start trying to show them you understand their problems. That’s the only “personalization” that has ever mattered.

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