Don’t Automate the Handshake

A human handshake beside a laptop with publication notifications, titled Don’t Automate the Handshake.

I was on a recent video call with a businesswoman I admire. She’s someone whose opinion matters to me, so when she smiled and spoke with excitement, I was pleased.

“Thank you for your two emails this week,” she said. “They were wonderful and super helpful.”

My mind raced. What two emails had I sent her? Hmm, since I can’t think of them, they must have been automated. Now what do I do?

“Thank you,” I said. “I’m glad I could help.”

She had asked to receive notifications when a publication was updated. The automation had done its job, and she appreciated the messages, but I hadn’t remembered what had gone out.

I made a mental note: If emails go out under my name, I need to remember what’s in them so I can continue the conversation. From her perspective, those helpful messages were part of our working relationship.

That’s when I realized our responsibility for automated communication continues after we hit send.

Use Automation Responsibly

Those notifications were welcome because she had requested them and they met a need. But an automated message can also arrive right on schedule and miss the moment.

Imagine telling someone you’ve had a rough week, only to receive a cheerful message three minutes later: “Fantastic! Are you ready to take the next step?”

Well, yes. Away from this conversation.

The message spelled your name correctly and included a handy calendar link. Somewhere, a system did exactly what it was told to do, while you wondered whether anyone had read what you wrote.

When Efficiency Feels Empty

Think about a good handshake. Someone looks at you, acknowledges you, and gives you a moment of their attention before moving on.

Now imagine that person looking over your shoulder for someone more useful while shaking your hand. Same grip, very different experience.

We can create that same feeling with our messages. We ask how someone is doing, but their answer has no effect on what happens next.

A person says they’re overwhelmed, and we send another offer. They mention a setback, and we remind them that our special pricing ends Friday.

The problem begins when we build a process that keeps talking without making room to listen. We may be moving people through the steps while giving them fewer reasons to trust us.

Adding a first name won’t fix that. We’ve all seen messages that feel like a form letter wearing a name tag.

Clear the Busywork

There’s plenty of work I’d gladly hand over to AI. Sorting notes, organizing information, and preparing routine drafts don’t need to consume the best part of the day.

If something is highly repetitive, that’s a good time to let AI carry the workload up to an agreed human checkpoint. Decide ahead of time where it should pause so you can verify the result or slightly adjust anything requiring a human touch.

For example, after a conversation, AI could organize your notes, identify the next steps, and prepare a follow-up email. At your checkpoint, you read the draft and make sure it reflects the conversation you actually had.

Maybe the next step is correct, but the tone is too cheerful for someone facing a difficult decision. Maybe one sentence needs to acknowledge a concern before you get down to business.

That checkpoint gives your judgment a place in the process. It also means you can begin with a useful draft instead of staring at a blank screen and trying to remember where you put your notes.

For routine notifications like the ones my colleague requested, you can approve the message and its trigger ahead of time. A brief summary of what was sent can then keep you familiar with the communication going out under your name, so you’re ready when someone brings it up.

The time savings become more valuable when you decide what to do with them. You could use a few recovered minutes to answer someone thoughtfully, make a phone call, or ask a question you would otherwise have skipped.

Keep the Human Moments

Some moments deserve more of us. A client shares a concern, a friend celebrates a win, or a colleague admits they’re struggling with something they usually handle well.

AI can help you prepare for those conversations. You can use it to gather relevant information or work through how to explain something clearly, then bring your own attention to the exchange.

Consider a client who mentions that their first book is finally finished. You could send the usual message about the next marketing step, and the project would keep moving.

But you could also take a moment to say, “You finished it! How does it feel to have the whole story on the page?” The marketing plan will still be there after you let them enjoy what they accomplished.

That question gives them room to respond as a person. Perhaps they’re thrilled, perhaps they’re exhausted, or perhaps they’re worried about what comes next.

Now you have something worth listening to. Their answer can help you understand how to approach the next step together.

The same is true when someone brings you a problem. Before reaching for the fastest answer, consider whether they need advice, a decision, or a little room to explain what happened.

You don’t have to turn every exchange into a long conversation. Sometimes one thoughtful sentence is enough to show that you were paying attention.

Before You Hit Send

Before sending an AI-assisted message, pause long enough to read it from the other person’s side. Does it reflect what they actually said, what they need, and what you sincerely want to communicate?

Then consider what they might expect from you. Someone asking about a delayed project may want a new delivery date, but they may also be wondering whether they’ll have to keep chasing you for updates.

You can subtly address that possibility with a useful sentence: “I’ll send you another update Thursday, even if we’re still waiting on the final piece.” That gives them something concrete without making a speech about how much you care.

A friend asking for your opinion may expect honesty delivered with kindness. A new customer may need a clear next step and a little reassurance that they understood the process correctly.

You won’t always know their expectations. Use what you know about the person and the conversation, and ask when the uncertainty matters.

Small adjustments can make a message feel considered. They also help you avoid sending polished paragraphs that leave the other person’s real question unanswered.

Keep Your Human Touch

This week, choose one repetitive task and let AI help you handle it. Set the human checkpoint, then use some of the time you save to give someone your full attention.

Ask about the book, return the call, or follow up on the concern they mentioned last time. Give the conversation enough room for their answer to matter.

Whatever you do, don’t automate the handshake.

Copyright © 2026 by CJ Powers