AI Coaches Can’t Do The One Thing You Need Most
Photo by Elias Maurer on Unsplash
The empty promise of AI coaching
Everyone is turning to AI coaches to help them think through challenges. For the most part, it works. But AI falls short in a few critical ways, one of which makes all the difference.
And it’s robbing you of real growth and connection.
AI is not listening
Have you ever been on a call with someone who is busily typing away as you’re speaking? Maybe they’re taking notes of what’s happening. Maybe they’re texting about lunch. Either way, they’re not listening. Not in a real way.
Perhaps they’re giving the appropriate responses — a well-timed ‘uh-huh’ or ‘interesting!’ They may even ask a pertinent question.
You won’t feel seen or heard, though. Not until they give you their full attention.
We don’t expect this of AI, of course. We know it’s not listening. Yet we still might think its trained responses are profound.
Why? Why do we settle for it? And if it can’t do this basic communicative task, what else can’t it do?
Other things your AI coach sucks at
Besides listening, AI falls down in several other ways…
It’s painfully generic.
Like a horoscope, AI is specific enough to sound personal but bland enough to blend.
We seem to keep forgetting that AI is simply a ‘next word’ predictor. It’s trained on billions of words to come up with the next best fit ones. And the next.
It’s only going to come up with something you find interesting, new, and novel by accident.
Which is why AI is great for making something sound “normal”, or common, or placid; it has perfected that.
There is no connection, no ‘there’ there.
My fridge might be smart and tied into my wifi network, but that doesn’t mean it’s connected to me. It’s a ridiculous thought, even to type out.
So perhaps it’s obvious to say that AI lacks connection, too. You may feel connected, but true connection loves you back.
Maybe you think feeling connected is enough. Like touching your own hand in a mirror.
Remember your first crush? Where you foolishly thought that showing them your strength of feeling was enough to spur reciprocal sentiment? They may even pretend back, a first and clumsy attempt at fake-it-until-you-make-it.
AI isn’t even trying to make it. It’s not trying anything.
Which brings me to my next point.
AI cannot react; it can only respond.
Again, imagine asking someone a personal question, and before they answer, you say to them:
“Don’t react to what I’m about to tell you. Instead, just give me the most probable amalgamation of all possible answers. Make it palatable, but also make it sound unique. Flatter me, but not too much. I want to be lulled into a sense of clarity, even if fleeting. I want to feel better.”
(We don’t need to supply this prompt; it’s built in.)
“You don’t really want to work it out. You want to be fooled.” — The anatomy of a magic trick, from Christopher Nolan’s The Prestige.
You cannot surprise the machine. Or delight it. Or provoke it. All you can do is feed it your endless stream of data. It will chew on it, byte after byte, and spit back a reconstructed version from everything its consumed thus far.
It doesn’t digest; it literally has no stomach for it.
Its timing sucks, and it has no rhythm.
Humans use all sorts of linguistic and paralinguistic cues to shape their interactions. Pacing, pauses, strategic silence, gesture, and tone.
In text, too. It’s the punctuation. Or emoji. Or interleaving of replies. The quickness of response. The hesitations and ‘ … ’ while you rewrite.
In human interaction, these are cues we take in without a lot of conscious awareness. On some level, we do notice. We react and respond accordingly, much of it beyond our control.
This creates the richness and connection we feel. Also the doubt, insecurities, and uncertainty.
AI has none of that. Its response is a prediction and is therefore predictable. Its delivery is too. Immediate and always on.
It’s unrelentingly there for you. It has no cycles or sleep, nor does it take a moment to think or reflect or question you or itself. As such…
AI can’t confront or challenge you.
If you feel confronted or challenged, it’s by accident, not design. A never-ending clock that will inevitably get something eerily right.
Maybe you don’t want to be confronted. After all, that’s what people are for. And you’re tired of it.
In that case, go on. Prompt away. Maybe you’ll be delighted by the happy accident that a machine is also capable of surprising you. Ta-da.
No judgement, but also no accountability.
It’s easy to tell AI that you’re going out again with that married man; it’s much harder to tell a person who might have their own thoughts and feelings about that.
That’s the comforting beauty of a one-sided conversation.
“You don’t really want to work it out. You want to be fooled.”
— The Prestige
Coaches will promise judgement-free accountability, but they’re people, too. And people are messy AF.
We’ll do our best, but between us is the awareness of a certain assessment of the situation, even if we don’t show it. We call this “what people might think”. It looms over us, especially the unsaid bits.
AI is free from this problem, as it doesn’t think. It has no idea what society might say, either.
So, if you want a “coach” for divulging your secrets to and making it ok, AI’s your guy.
Dispelling the magic | doing the math
All these things add up. We get to choose whether the sum is something truly magical or merely foolish.
AI will tell us, in its uncanny way, that the answer is 7, but if we look more deeply, we know the score.
Numbers aside, the broader implication is this:
There is no partnership with AI.
It’s not possible.
Shattering the AI illusion
Twenty years ago now, I was heading up I-5 with my long-distance surfer boyfriend. For reasons young and mundane, we were on the verge of splitting up.
He was driving and I was flipping through my phone, looking for someone I could reach out to. I wanted to share this pain, to ease this ache.
When I scrolled to his name and number, I felt awash with cosy relief. There was someone I could talk to. He was a comfort only a few taps away.
But he was right there. And I realised that my imaginary long-distance surfer boyfriend and my very real, grumpy one beside me were not the same guy.
And while I longed to call the faraway one, it was the present one I really wanted.
I wasn’t ready to let go of my computer-mediated substitute just yet.
You might not be ready, either.
That’s ok. AI has its uses. Even for coaching-like conversations.
Everybody gets bored of meal substitutes eventually. You long for something green. Or juicy. To sink your teeth into.
And when you do, here’s what you remember…
What we’ve been missing
True growth goes deeper than the dazzle. Can you say that you were a different person after a conversation with your AI coach? Probably not.
Maybe that scares you anyway. Besides, some of you don’t really want it. The lifestyle without the truly gritty bits; a starving artist without the suffering. Or the art.
Working in real conversation takes you further. Real conversations don’t pull punches. And other things…
A human conversation feels better.
When you interact with a real, responsive person, there are moments.
You talk in metaphors. Something makes you smile. A question cuts to the core. You sit with doubt. You stumble on the next bit. You move forward together.
Put another way, how often do you walk around in a daze, mind still blown over that thing the AI pointed out to you?
Do you hear its voice in your head?
Or feel that hopeful feeling that you know, maybe, just maybe I’m making progress here? You laugh because you surprised yourself even thinking something so abjectly optimistic.
The answer is no to all. It’s never happened.
But that’s just how it works with a coach. By design and with intention.
Person-to-person coaching includes all of you, not just the thinking-in-words part.
As people in conversation with other people, we can’t help but leak our identities all over the place. It’s in our appearance, it oozes out of our opinions, and it’s in our words and how we say them. We can’t help it.
Where AI holds up a mirror for you to navel-gaze into, a coaching conversation “is more like two people side-by-side, looking in that mirror together.” says Fabio Salvadori.
What you see is fundamentally different.
In the AI mirror, the other-human perspective is entirely absent. Or as ChatGPT might say:
No judgement. No reaction. Just a series of predictable words.
— from AI Tells, Beyond the Em Dash
The one thing AI can never do (and people can’t help doing)
All of these qualities point to the same thing. It’s the thing that makes us human and dynamic and responsive.
That thing is noticing.
The most important quality a coach, conversational partner, or friend can have is the ability to notice. This requires listening. With a mind and a whole body.
It also requires presence, thought, connection, and care.
So here’s the real question that AI will never dare to ask, but I, messy human that I am, will:
Why are you reaching for something that is devoid of all that?
This story was first published on Medium on 9 July 2025.
