Why “I Hope This Email Finds You Well” Feels Outdated (and What That Means for Business Communication)

If you’ve ever started a professional email with “I hope this email finds you well,” it’s time to rethink your approach. Frankly, when I see this opening in my inbox, I’m already docking points from the sender’s credibility—mentally, at least. And if the rest of the email feels overly polished, like it’s been churned out by an AI chatbot, the credibility gap widens.

We seem to be entering an era where emails are beginning to resemble second-grade homework—work that parents finished for their kids. Sure, you might have drafted your message, then tossed it into a chatbot for refinement. It’s a tool, right? Using tools isn’t inherently bad. But here’s the catch: when emails become perfectly grammatical yet unnaturally verbose, loaded with adjectives, they feel less authentic.

It reminds me of the early 2000s, right around the time I graduated college and the dot-com bubble burst. The internet was new and exciting, but also disruptive. Today, AI feels like it’s following a similar trajectory. The potential for engineering and technological innovation is astounding. But on a human level, something important feels at risk—our ability to connect authentically.

For businesses, this presents an opportunity to lean into real, personal relationships rather than relying on the illusion of connection. My company, for example, prioritizes customer service. When our customers call, they speak to an actual person. Contrast that with the experience of contacting a large internet or mobile service provider. You’re greeted by an automated prompt urging you to use AI chat—on SMS, on the website, everywhere. We’ve all been there: typing expletives into a chatbot, hoping for a real person to notice.

As small businesses, we have to ask: will we all eventually outsource “low-level” services to chatbots? Will every interaction be automated? Maybe I’m old-fashioned, or maybe I just need to let the technology mature. But for now, I believe we’re missing something critical.

Here’s my perspective: my business’s goal is, and always will be, to provide exceptional customer service. Our customers are the most important people in the world to us. If adopting new technology risks undermining that, we won’t do it.

As larger companies embrace automation that dehumanizes interactions, opportunities abound for businesses that double down on exceptional, human-centered service. Yes, technology can enhance those experiences, but it shouldn’t replace the connection itself.

In my experience, I have yet to encounter an automated interaction that didn’t leave me feeling at least a little frustrated. CEOs may argue that these changes boost shareholder value in the short term, but consumer sentiment is a long game. Over time, people will notice when a brand feels less personal. They’ll talk about how it “isn’t like it used to be,” and soon enough, a new player will come along to disrupt the status quo by doing things better.

Maybe I’ll feed this writing into a chatbot for kicks. But here’s the truth: the best connections, whether in writing or customer service, are built on authenticity.

 

Below is my originally written version of this article.  I used ChatGPT to have it re-written for me.  The polished version above is very good, so maybe I’m being hypocritical here.  But I stand by the intention of my article.  Be careful what you use AI to do… if you don’t check your work, you may find that the message you send to your recipient is not coming across as intended.

 

“I hope this email finds you well…” is not what I expect to see in a professional email from anyone in current times.

If I get an email from anyone with this as the first sentence, I’ve mentally deducted 10% or more perceived credibility from you.  If I continue reading and it becomes even more clear that your email came directly out of the AI Chat-bot then you’ve lost all credibility.

I think we are in a time when everyone’s emails are starting to look like 2nd grade homework assignments that their parents did for them.  Maybe you did the brunt of the work, then stuck it in the chat bot for refining… ok, it’s a tool, we are just using the tool, that’s not bad right?  Maybe… but the more emails that I get which are perfect grammatically, and tend to have an overuse of adjectives, I become more skeptical of the source, and therefore question the credibility of the person who sent the email.

I’m not sure of the main point, but from my perspective, AI feels very much like how we felt about the internet in 2001. (The year I graduated college and the year the internet bubble burst.)  There are clearly TONs of amazing uses for this technology.  The engineering ramifications are already AMAZING.  But on the human level, I feel like we are losing something important.  Or maybe to take it a step further, there is an opportunity for companies to lean-in to developing truly personal relationships and not just pretend.

For example, my company provides customer service.  Our customers call us and talk to us on the phone.  If I got to (pick any large ISP or Cell phone provider)’s website and try to call, there will inevitably be a message trying to get me to use their AI Chat via sms or “live” chat on the website.  You know you’ve been there.  Cussing at the screen, or typing the most offensive things known to man all in hopes that there may be a person somewhere on the other side watching realizing that they are pissing off customer after customer with their “new technology.”  As we go down this road, this progression, is my small business eventually going to outsource it’s “low-level” services to a chat bot?  If I do that, and everyone else does that too, then we will ALL have these great customer service robots there to help us?  Maybe I’m just naïve and I need to let the technology develop further and I’ll see the benefit.

Here is my truth…my businesses will always have the goal of providing exceptional customer service.  Our customers are the most important people on the planet, so we will never take any shortcut, or use any tool that we feel could potential take away from that goal.  I believe that as larger companies implement some of these technologies that de-humanize many business interactions, there will be tons of opportunities to provide better service experiences.  I agree that those service experiences SHOULD utilize the best technologies to improve those interactions.  Although, as it currently stands, I personally have yet to have an automated interaction with another company where my opinion of that company was not tarnished in some way.  I’m sure the CEOs of those companies “increased shareholder value” in the short term, but consumer sentiment is not instant.  Over time, conversations about how (pick any large consumer facing org.) has changed, and they are not like they used to be, will start, and soon enough a new player will come along to disrupt and do things better.

Maybe I put this writing into the chat bot to see what it says…