“Enshittenification” has such a distinctive ring to it, doesn’t it? It captures the sordid flavor of the thing it describes. Please pardon the crassness of a cussword wrapped in 6 otherwise innocent syllables. I didn’t coin the term (Cory Doctorow gets that honor), but it refers to the gradual worsening of a product or service over time, usually through a (largely) benign misalignment of incentives between producer and consumer, and usually done for rational and completely defensible motivations on the part of the producer.
Outsourcing, automation, disposable parts, tiered support, cheaper materials, phone trees, chat bots. You get the idea.
You also know what it feels like to be on the receiving end of these things. Yes, they enable lower costs, greater availability, anytime self-service, and a host of other like benefits that are largely invisible unless we can will ourselves to imagine a world without such miracles of scaling, automation and commoditization.
But if you’ve ever thought to yourself “They don’t make ‘em like they used to” or “What do I have to do to talk to an actual human who cares?”, that’s you feeling the tradeoff.
If the swelling of spammy marketing emails arriving in my inbox pretending to know me (to varying degrees of convincingness) or the rising prevalence of chat bots as a first line of defense to get actual customer support is any indication, AI is poised to enshittenify many industries. Again, these are all for rational and defensible motivations of the parties clamoring to add AI to the mix of how they engage with the world of customers and leads.
To be on the receiving end of this AI-fueled innovation? Less clamoring.
Surely this varies on a case-by-case basis. If an AI agent can actually (and accurately!) answer my question or solve my problem without me waiting for the next available representative, count me among the clamoring! It depends on the execution, and on the service.
Which brings me to coaching.
Coaching itself is a service that is intrinsically high-touch, highly tailored to the receiving individual (if not outright unique), and, whether we like to admit it or not, powered deeply by being cared for (or at least the perception thereof… believe me, some coaches fake it better than others).
You might be excited to incorporate AI into your coaching, to ride the tide of the cutting-edge hotness. Perhaps it’s to have a competent note taker in the mix, or to help identify patterns or themes in whatever’s going on with your client, or even more clever and carefully considered applications you may have in mind.
If that’s you, I offer a simple question for your consideration. Would your clients share this excitement?
I ask because I’ve been on the receiving end of coaching that recorded the sessions, used AI to generate a transcript, and another AI to give a summary of that, and that transcript and summary is what I was ultimately given as the takeaway from our session.
Did I find this an impressive or even valued addition to the (quite good) coaching conversations I had? Dear reader, I did not. If anything it diminished the memory of it all, and not just because of the soft focus, quasi-accurate degradation of the actual substance of the conversations, degradation which missed the nuance that good coaching–with its intentional listening–prides itself on evoking.
No, it was something else.
“Here you go, here’s what a mathematical averaging and correlative pattern matching inference engine thinks is important and relevant in your situation.”
“I couldn’t be bothered to take 5 minutes to write up and share what I thought most useful, but here’s the output from an automated process that you yourself could cook up with a file upload and a little copy-and-pasting using commodity tooling.”
“You can read through the raw dump and mechanically generated distillation thereof, isn’t that nice?”
“You paid $500 to talk with me for 90 minutes, but I’m going to let a machine be responsible for what you’ll ultimately have to remember it by.”
My coach didn’t say any of that, but that’s what I heard.
This characterizes the enshittenification of coaching as being on the receiving end. If you wish to be a high touch, high ticket coach who is sought out for your ability to deliver great value to your clients, consider that incorporating these “innovations” might run counter to that.
Let me end this all on a positive note, and not just wagging my index finger at you. There’s a silver lining to all this, for coaches interested and willing to take it. AI is here to stay, the number of requests I get to integrate CoachAccountable with AI note takers and the like is proof enough of that. A lot of your colleagues are weaving AI into their workflows, and even into what they pass off to their clients. You’re likely tempted to as well, if you don’t already.
Here’s where you can use this to your advantage. To the degree that AI pervades coaching, you can stand out by proudly saying you don’t do it. That you don’t invite a machine to listen in on what are generally intimate conversations. That you personally care and are willing to take the time to summarize and share what you thought was most important. That your attention to and awareness of our progress is enough to effectively coach us, without relying on a maximally probable patterned inference, derived from whatever an LLM was trained on which happens to resemble, hopefully enough, our situation.
In other words, if coaching is going to be enshittenified by AI, you can double down on the fact that you still offer the fully human touch. At the sort of hourly rate you’d probably like to command, we clients will thank and appreciate you for it.
You’re also able to compose and share notes easily, with Key Insights that pull for easy creation and sharing of what matters most.
In other words: high-touch, detailed attentiveness comes out of the same efforts that keep your client present to progress and moving forward with clarity, all offered up with minimal marginal effort, by you, a human who demonstrably cares.




