Automation Without Abandonment: A Case for Human Contact in a Digital World
If you regularly read my blog and newsletter, you already know I have a complicated relationship with technology.
Sometimes I feel like I’m doing fine… right up until I’m not. Based on the feedback you’ve shared with me over the years, I’m not alone. A lot of smart, capable people, many of them leaders, quietly feel the same way:
“I can run a business, lead a team, and make big decisions… but this “simple” online thing has me stuck.”
Here’s the issue I’m still chewing on.
So many online services are “free” (or inexpensive) to subscribers, but when something goes wrong, there’s no phone number to call. No human being. No voice. Just an online help desk, a chatbot, or an email form that says, “Tell us what you need,” as if that’s the easiest part.
The problem for me is this: I often don’t know what question to ask.
When something isn’t working, I can usually describe the situation. I can tell you what I clicked, what I expected, what I saw instead, what I tried next, and how I ended up going in circles. But turning that experience into a neat little “support ticket” feels like being asked to diagnose your own car before you’re allowed to speak to a mechanic.
And then, when the written response comes back, it’s often packed with jargon or steps that assume you already understand the system. “Clear your cache.” “Disable extensions.” “Authenticate via SSO.” “Check your DNS.” By the time I’m done reading the instructions, I’m more tired than I was when I started.
What I want to say is: “I just want to talk to someone.”
Now, I can hear a technology consultant (Scott Klososky comes to mind) giving me the tough-love version of reality: “This is the world now. Get over it.” And maybe he’s right. Maybe expecting a phone number from every service is unrealistic.
But I’m still not convinced we have to accept the extremes:
Option A: Everything is automated. Good luck.
Option B: Every company staffs a full call center forever.
Surely there’s a middle ground, especially for organizations that care about trust, loyalty, and long-term relationships.
Why this matters more than “customer service.”
This isn’t just a personal gripe. It’s a leadership issue.
Because the moment your customer (or employee, or vendor) feels stranded, something important happens: their confidence drops. They start second-guessing themselves. They waste time. They feel embarrassed. Then frustration kicks in. And once frustration shows up, people do one of two things:
They quit (cancel the service, abandon the process, disengage from the change).
They escalate emotionally (angry emails, public complaints, or “I’m never using this again”).
Neither outcome is good for anyone.
And here’s what I’ve noticed: the more “modern” and “efficient” a system becomes, the more it can accidentally create a sense of distance. The company feels far away. Untouchable. Like there’s no door to knock on, only a maze to navigate.
That’s not a technology problem. That’s a design problem.
Related Read: Before You Hit Send: The Efficiency Trap for Business Owners
The “middle-ground” solution I’m looking for
If I ran one of these software companies (which I do not), I wouldn’t promise unlimited phone support for every user at every price point. But I would build in at least one or two “human ramps” for the moments that matter.
Here are a few practical middle-ground ideas, things I’ve seen work in other industries and that leaders could adapt:
A clear escalation path. Not every issue needs a live person, but some do. Make it easy to move from self-service to human help when the situation is complex or time-sensitive.
Live “office hours.” Even one or two scheduled windows per week where customers can talk to a real person (or join a live group Q&A) can dramatically reduce frustration.
Screen-share support (by appointment). A 10-minute screen share can solve what 20 emails cannot. It’s efficient and humane.
Plain-language responses. If you’re going to offer written support, write like you’re helping a smart friend who wasn’t trained on your product. Less jargon, more context.
A concierge layer for business customers. If the product is used by teams and leaders, there should be an option (even paid) for a named point of contact when something important breaks.
Notice what all those have in common: they don’t reject technology—they simply acknowledge a truth about people.
When we’re confused, we don’t need more menus. We need clarity. And sometimes clarity comes fastest through a conversation.
A Question for Leaders
If you lead a company, here’s the question I’d like you to sit with:
Are we designing our systems, both internal and external, around efficiency for the organization, or around the experience of the person on the other side?
Because it’s possible to be “efficient” while quietly exhausting your customers and employees, and it’s possible to modernize in a way that builds confidence instead of draining it.
Technology will keep advancing.
That’s not up for debate. The real question is whether we can build cultures and processes that help people keep up, without making them feel small in the process.
And for what it’s worth, I’m still working on this myself. I may eventually “get over it.” But I hope we don’t lose the expectation that some level of direct human contact is not only reasonable, but it’s wise.
If you’re navigating technology changes, customer experience challenges, or internal process upgrades, and you want to do it in a way that actually works for your people, this is exactly the kind of leadership muscle we build through executive coaching: clarity, communication, and practical systems that don’t leave others behind.
