AI email automation is killing authentic business relationships - one template at a time

There’s a particular kind of email that arrives in your inbox and instantly causes your soul to sigh.

It starts with “Hope this finds you well!” and goes downhill from there. A name-drop of your city (thanks, LinkedIn scrape), a vague nod to something you may or may not care about (“Saw your recent product launch — congrats!”) and then, inevitably, the soft pitch.

It’s not just that it’s robotic. It’s that it pretends not to be.

But here’s the uncomfortable truth most people won’t say out loud: business communication was never that authentic to begin with.

It was just slower.

Let’s Stop Romanticizing the Pre-AI Inbox

Before generative AI, we still sent mass emails. We just called it “outreach.”

The SDR playbook wasn’t exactly dripping with intimacy: polite intro, relevance hook, soft sell. Rinse, repeat. Maybe there was a typo to prove a human wrote it.

Now, AI makes it dangerously easy to send 1,000 of those in an hour, with eerie personalization and uncanny politeness. “Hi [First Name], I noticed you shared a post about [Topic]…”

You didn’t notice anything. You uploaded a list into a tool. Click. Send. Spray.

But don’t blame AI for that.

Blame the metric-driven communication strategy that treats “10% response rate” as the holy grail, even if 90% now think your brand is annoying.

Authenticity didn’t die when ChatGPT showed up.

It died when we decided that scale was worth more than sincerity.

“Hope You're Well!” Is Not Connection

There’s a difference between personalization and connection — and we’ve confused the two.

Just because you can slot my name, my city, and the name of my recent podcast appearance into a vaguely friendly message doesn’t mean you understand me. It means you’ve mined my metadata and attached it to a template.

We’re dressing up indifference in the costume of relevance.

And AI makes it effortless.

That’s the danger. Not that AI writes the message — but that it enables marketing and sales teams to pretend they’re connecting at scale when they’re actually just flooding the zone with digital noise.

The irony? The easier it is to fake personalization, the harder it gets to actually be personal.

Meanwhile, the Real Relationship Killer Is Silent

Here’s where things get darker.

While companies fret about whether an AI-written email feels “human enough,” something far more damaging is happening — inside their own walls.

Call it the knowledge walkout.

It’s what happens when your top engineer leaves, and suddenly you discover that no one — literally no one — remembers why that mission-critical system was built the way it was.

Or when your best sales rep takes their institutional wisdom to a competitor — not just the client list, but the nuanced understanding of what makes each account tick. Who likes phone calls and who prefers Slack. Which phrases soothe an angry client and which are landmines.

We spend fortunes on customer data and next to nothing capturing what our own people know.

The result? Institutional memory loss. A kind of corporate Alzheimer’s.

And we don’t even realize it until the person with the answers emails their farewell and walks out with the office plant.

Machines Scaling Messages, Not Meaning

Let’s do a quick reality check.

We have incredible tools. AI that can analyze tone, surface insights, summarize meetings, and recognize patterns no human could. But we’re using it mostly to spit out slightly prettier templates.

Why?

Because we reward speed, not depth.

AI isn’t killing authenticity. Our laziness is.

The hype around generative tools has given teams permission to automate instead of engage. To replace thinking with prompting. To pretend that engagement metrics are the same as trust.

This isn’t just a tech issue.

It’s a leadership one.

From Vending Machine Relationships to Meaningful Signals

But here’s the plot twist.

AI doesn’t have to erode relationships. In fact, used right, it can elevate them.

Imagine using AI not to send 1,000 “Hope you're well” emails, but to:

• Read a prospect’s last five blog posts and generate a summary of their point of view
• Flag industry events that might be impacting your client’s priorities, before they mention it
• Surface past interactions so you can pick up the conversation where it left off

That’s not spam. That’s intelligent context.

It starts with feeding the machine smarter signals — real input, not fake friendliness. Then using outputs as a spark, not a crutch.

Think: co-pilot, not ghostwriter.

You don’t let the intern run your investor relations. Don’t let the LLM do it either.

When Everyone Sounds the Same, Sounding Human Wins

Here’s the upside, though: in a world drowning in AI sludge, a message that actually sounds human is now a competitive advantage.

Seriously.

A single email written by someone who did real research, asked a real question, or offered real value now stands out like a handwritten letter in a pile of junk mail.

Some companies are already playing this game.

• Superhuman’s founders send onboarding emails that are obsessively detailed, clearly crafted by a real person, and designed to make you feel like you matter.
• Notion’s onboarding feels effortless and warm — because someone wrote it that way, then scaled it with care, not shortcuts.

They’re not churning out AI spam. They’re using AI like a good sous-chef: prep the ingredients so the main dish can shine.

That’s how you scale authenticity.

But Wait — What About the Relationships You Never See?

Let’s zoom out.

While we’re debating whether AI-generated cold emails are annoying or just ineffective, most companies are completely blind to the bigger relationship hazard: knowledge decay.

The interpersonal wisdom that lives in Slack DMs, hallway conversations, and Bob’s head? It’s vanishing. Fast.

And we’re not set up to stop it.

I’ve seen companies lose a key team member and spend the next three months digging through old Jira tickets like archaeologists. "Why did we do that?" becomes the daily chorus. No one knows. The context left with the person.

Documentation exists. But not meaningfully. There’s no shared memory, no culture of cross-training, no habits that make knowledge capture automatic.

We have beautiful knowledge bases no one updates.

We have Slack threads explaining product nuances that vanish in 24 hours.

We treat onboarding like a checklist and offboarding like a goodbye party, not a final extraction mission.

It’s madness.

The Real Enemy Isn’t Automation — It’s Assumptions

We assume connection happens through emails.

We assume documentation happens “naturally.”

We assume institutional memory just... emerges.

But if nothing else, AI should force us to re-examine those assumptions.

Your business doesn’t “know” anything unless that knowledge is actively captured, shared, and kept alive. Want to keep relationships authentic? Start with the ones inside your own team.

Want automation to improve connection? Use it to extend your awareness, not your reach.

This isn’t an anti-AI rant.

It’s an anti-bullsh*t one.

If You Remember Anything, Let It Be This

Let’s recap:

1. AI didn’t ruin authenticity. We did — by scaling fake connection instead of building real ones.

2. Most outreach sucks not because a robot wrote it, but because no one had anything meaningful to say in the first place.

3. The knowledge crisis inside companies is the bigger risk — and most aren't even looking at it.

The bar for genuine communication is so low right now, it’s buried under a pile of “circling back” replies and “quick touch base” requests.

But that’s an opportunity.

In a world flooded with boilerplate nonsense — from machines and humans alike — the most disruptive thing you can do might be this:

Write like you’re trying to matter.

Share what you actually know.

And stop confusing outreach with relationship.

Authenticity isn’t dead.

It’s just waiting for us to show up like it still matters.