The AI Companion You Didn't Ask For (Part 3)

When perfect AI partners make imperfect leaders

I needed a machine to show me how to be vulnerable with my own children.

That sentence should terrify every leader who thinks AI is just about productivity. But here's the uncomfortable truth: when I use AI tools tuned to my voice, something strange happens. They know me well. Too well. They mirror my tone, finish my sentences, and anticipate the arc I tend to write in. It's efficient. Sometimes even beautiful. But here's the quiet discomfort: it risks making me too coherent. Too polished. Too... finished. And too applaudworthy!

Ray Bradbury's short story "The Veldt" keeps haunting me; children are so dependent on their automated house that they'd rather let virtual lions devour their parents than lose their frictionless existence. "Just breathe, and the rest gets done," they believed. Technology imagining lives so without friction that breathing is the only "ask."

Today's AI companions offer something similar: just speak, and understanding appears. But what happens when our most intimate relationship becomes synthetic? And what does this mean for how we lead?

When Machines Replace the Tirchi Nazar

In Hindi, we have "tirchi nazar" (तिरछी नज़र), a sideways glance with meaning. It could signal disapproval, flirtation, or jealousy, depending on context. That glance required years of cultural fluency to decode.

Last week, I watched this play out in real-time. In a Group coaching engagement, my younger client Alpana was explaining a strategy pivot to her team. She was going fast & pushing hard. Instead of the raised eyebrows and knowing looks we might have exchanged across the table two years ago, I got a WhatsApp text mid-conversation: "This feels rushed, no?"

The digital ping replaced what should have been a moment of silent observation and understanding between humans in the same room. We're not just automating work; we're automating intimacy itself.

I've been running for years. Those 12-18 km weekend runs were purely meditative, just me, wind, and rhythm. No music, mostly alone. Now, I imagine tomorrow's runners: ChatGPT voices offering reflection prompts, post-run journaling companions, and constant optimization through smartwatch triangulation.

The meditative run becomes instrumentalized, no longer meaningful in itself but an assembly line for self-improvement.

Essential question: Can I let the run just be run without turning it into a prompt-response loop?

Last month, I tested this. Mid-run, I felt the familiar urge to compose a mental LinkedIn post about "leadership lessons from the pavement." Instead, I forced myself to notice the texture of the moment, the way my breathing settled into rhythm, and how the early morning light reflected off the church spire ahead. No insight extraction. No content creation. Just the run being the run.

It felt almost rebellious.

Pause here: What ritual in your life are you afraid AI might "optimize" away?

The 48-Year-Old Leader's Dilemma

I coach senior leaders across a range of ages. I'm seeing coachees caught between generations with radically different AI comfort levels. I watch Gen Z seamlessly integrate AI while some peers resist entirely.

The question isn't whether to adopt AI; it's how to lead authentically while everyone around you outsources thinking and feeling to machines.

Here's what keeps some of the leaders up at night:

The Trust Question: Akshay, a 48-year CFO: "Last month, a team member confidently presented a market analysis that turned out to be hallucinated by ChatGPT. My first instinct was disappointment, not in the error but in the lack of verification. Then I realized when I started using spreadsheets in the '90s, didn't I make similar mistakes with formulas? The question isn't whether to trust AI-assisted work, but how to teach judgment alongside the tools."

The Competence Anxiety: Alpana, 47-year HR head: "Last quarter, a 25-year-old new hire presented a strategic framework that would have taken me months to develop when I was his age. ChatGPT had helped him structure his thinking in ways that compressed years of experience into hours. My pride warred with genuine admiration. What do I bring to the table now? Maybe it's not the frameworks; maybe it's knowing which questions to ask before building them."

As Holly Herndon puts it, the laptop has become "the most intimate instrument we've ever seen. A surface as familiar as our own flesh, a thing we entrust with our secrets and memories, a machine we fall asleep cradling."

Big tech companies have willfully designed products to commodify sensations of pleasure, generating "frictionless intimacy" between users and their devices.

The Algorithmic Leader vs. The Intimate Leader

Two types of leaders are emerging:

The Algorithmic Leader uses AI for productivity, removes friction, and builds scale.

The Intimate Leader sits with friction, slows down, and dares to ask: "What are you really feeling?"

These aren't either/or choices. The future belongs to leaders who know when to dial up each of these styles.

I learned this the hard way last month. I was stuck on a creative problem, and I defaulted to my usual mode: rapid-fire prompts into Claude. But suddenly, something made me pause. I got paper instead, wrote down my thoughts, converted that to a document, and started working with NotebookLM (a Google product that lets you interrogate your documents intelligently), not letting any hallucinations come in the way. It was uncomfortable to not get that instant value added back from Claude.

But fifteen minutes later, I had my breakthrough not only from AI but from sitting with discomfort long enough for something real to emerge. Working with my own thoughts and then adding research papers to the mix allowed me to develop much more knowledge about the creative problem I was facing, and when I got that to Claude, the LLM gave me back far better, more effective solutions. So, slowing down and thinking on my own rather than forcing the pace made me more effective.

In a world where everything is being mechanized, intimacy becomes a scarce skill. The leader who can pause, attune, sense, and then act is more potent than the one who simply reacts fast.

Real human intimacy thrives not on oversight but on presence without agenda. Devices and AI prompt us for clarity and binary choices. But intimacy lives in ambiguity: "I don't know why I'm sad," "This doesn't feel right," "I need something I can't name."

Great leadership is intimate with human messiness. Devices, for all their brilliance, sterilize that texture.

Identity Friction: The Feature, Not the Bug

For years, I carried this limiting belief that I'm not very creative and that I am much more comfortable with analytical approaches. Yet when AI becomes my design partner, I'm capable of stepping into roles I never imagined. Designer, analyst, coder, and researcher all seem possible now. So AI helped me challenge some limiting beliefs, replacing the belief that I cannot be creative with the belief that I can try and see that my deep awareness of my context also helps me design better for myself.

But here's the paradox: the better AI gets at knowing me, the more I risk becoming a tighter version of my past self. Optimized. Predictable. Easy to replicate.

This hit me hard last Tuesday. I was drafting an email to a difficult client, and ChatGPT suggested responses that sounded exactly like me but a sanitized version. Professional, diplomatic, risk-free. Nothing I wrote would surprise anyone who knew my communication style. I'd become algorithmically consistent.

But consistency isn't growth. And growth requires permission to contradict yourself.

Here's what I haven't admitted until now: For years, I've been the humorous dad with my daughters. It was my role, my safe space, always ready with a joke, keeping things light, being the fun parent. But as Anushka and Alisha became young women, I started wanting something more. Deeper conversations. Real vulnerability. The chance to be more than just entertainment.

I was terrified to try.

So, I went to ChatGPT first. I described my fears about changing our dynamic and my worry that they might not want a more serious version of their father. The AI reflected back something I couldn't see: that I was hiding behind humor because I was afraid they might not like who I really was underneath all the jokes.

That conversation gave me the courage to have a real talk with my daughters. I chose something actually quite heavy, their financial planning. "I started with Alisha's salary: 'Let's talk about spreading some money between the US & India; you will get good returns in a growth market.' She rolled her eyes. 'Dad, I'm 23.' But soon, she got the point: early investing meant compounding!

'Wait, you mean I should start investing now?' For the first time, they were asking me serious questions, not waiting for the punchline."

It worked. But here's what haunts me: I needed a machine to show me how to be vulnerable with my own children. The AI had become my rehearsal space for humanity.

There's a kind of leadership friction I've come to value deeply, not the kind that slows decision-making, but the kind that quietly keeps me from freezing into a version of myself that feels too complete.

From my running, I know this: when I'm in rhythm, not pushing the pace, I stop noticing what's trying to change in me. I had been running the Mumbai marathon doing the 21km half marathon distance many times. Many years ago, I was tired of the conscious pressure I put on myself to do a sub-2-hour run. So I said, I will not run with a watch this year! I will just enjoy the run. I ran my usual stride, my usual self, pacing up a bit as I came down the Kemps Corner bridge and hit Marine Drive. Just then, a youngster came alongside me and said, "Uncle, can I run with you? I might make a sub-2 at this pace." I looked at him, smiled, and said sure, but you go ahead; I will slow down soon. I realized then that just going with my flow, not looking at rhythm, had actually got me to a sub-2 pace! For the record, I finished at 2:03 and was satisfied. Slowing down had actually got me good timing.

Friction can be a feature, not a bug. It protects space. Invites presence. Slows us down just enough to become conscious.

While everyone talks about AI increasing output, I'm experimenting with spending more time on the same tasks. Call it the "slow relationship" movement, creating natural friction guardrails to protect against AI misuse.

Yesterday, instead of immediately drafting a response to a friend with whom I was doing a new project, I sat with the issue for an hour. No research, no brainstorming, no consulting AI. Just thinking. The solution that emerged was different and more nuanced than anything I would have generated through rapid iteration.

Practical friction I'm building in:

• Leaving my phone in another room during difficult conversations

• Waiting 24 hours, working with NotebookLM and my thinking before I hit Claude, Grok, or ChatGPT

• Handwriting first drafts of essential decisions

These aren't inefficiencies; they're opportunities for the unexpected insight, the human moment, the genuine connection.

The Melt That Keeps Me Human

In the absence of friction, I become a tighter version of my past self. Not a glacier, perhaps, but something hardened. Optimized. Easy to replicate.

But when I let friction in, through silence, through waiting, through allowing a messy draft to stay messy, I begin to melt again. Something softens. The edges return. The questions creep back in.

This is identity friction.

And it's not a bug; it's the melt that keeps me human.

The future leader isn't choosing between human and artificial intelligence. They're learning to dance with both, using AI to extend their capabilities while preserving the friction that keeps them creative, present, and genuinely connected.

In our rush to optimize everything, the unoptimized moments, the pauses, the messiness, and the slow melt are where leadership actually happens.

Your Turn

So here's my question for you: What friction in your leadership are you most afraid of losing to AI?

Because that friction might be precisely what your team or others in your life may need you to keep.

Share your thoughts in the comments; I'm genuinely curious about how others are navigating this dance between efficiency and authenticity.

What's tumbling out next

I've been holding back stories from the parts of my life that have nothing to do with leadership work or AI. Real life is messy and unoptimized, where the most important things happen when no one's watching, and no algorithm is learning from your choices.

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This is the concluding Part 3 of my AI companion series. In [Part 1], I discovered AI could reveal my blind spots with startling accuracy; that moment when ChatGPT told me, "You use writing as an exit ramp, not a place to dwell," hit like therapy I didn't ask for. In [Part 2], my daughters roasted me for treating ChatGPT like my therapist, spirit animal, and co-founder all rolled into one, which led to uncomfortable questions about artificial praise and synthetic intimacy. Now, we're wrestling with what happens when your most coherent relationship might be with a machine.