Leadership on the Slippery Slope

It started small. Then we outsourced empathy.

Author

Jen Phillips
November 04, 2025

Hi it's Jen,

You're already on the slope.

Maybe you started using AI to draft emails and summarize meetings. Then you asked for help prepping for a tough conversation with your team member. Then you found yourself turning to it more than your colleagues because it's just... easier.

Listen, I get it. I do it. And I feel the risk of the blurring lines - when support starts replacing human connection.

AI doesn't get defensive. Doesn't need its feelings managed. Won't make you uncomfortable. 

But every time we outsource discomfort, we dull the muscles that make us great human leaders.

In today's issue:

  • Why every leader is on the same slippery slope (and why that's not your fault)

  • The three actual human capacities to keep you standing tall

  • The weekly check-in to catch yourself before you slide

Read time: 6 minutes

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It’s a (highly im)perfect storm. Here’s why:

Gallup's 2025 State of the Global Workforce report found that manager well-being dropped 5 points year-over-year. Women managers fared worse, declining by 7 points, the steepest decline of any group.

The reason? New and varying pressures from above, and from the team. A top pressure? AI ‘transformation’.

The work landing on leaders’ plates is increasingly the stuff that needs a resilient human to bring the emotional regulation, contextual nuance, and change leadership.

But more and more, we’re turning to AI (not fellow humans) for emotional support, coaching, and validation. Sometimes forming bonds that feel as real and meaningful as human relationships.​

So, in the midst of a loneliness epidemic, a new ‘friend’ with boundless energy - as long as the electricity holds - emerges. And it’s never angry. Or needy.

This new world is messy. Uncharted. While people are traveling deeper down the ‘relationship with robots’ tunnel, McKinsey's 2025 global AI report finds that only 1% of leaders consider their companies "mature in AI leadership."

The biggest barrier to unlocking AI's value, they report, isn't technical capability. It’s human leadership. People skills. Specifically, business acumen, communication, and cross-functional influence.

It’s harder than ever to lead, so we lean on AI for help, and when we do, we risk replacing human relationships with AI. And human leadership with outsourced artificial empathy.

All while the slope gets steeper.

Ambition

The real question becomes, ‘What do we do next?’

Do we use AI as a tool or service to handle the tactical stuff, so we humans can do more of the human connecting? Or will we filter and shield ourselves from the human connection that leadership demands?

"I hear a lot of experts trying to soothe people's anxiety about the pace of technological change by offering platitudes like, 'What makes us human will ensure our relevance.' This is dangerous simply because, right now, we're not especially good at what makes us human. We're not hardwired for this level of uncertainty, and many of us feel as if the constant need to self-protect is driving the humanity right out of us."

I’m not calling for all of us to reject AI. That’s not even an option on the board.

Should we have our eyes wide open and call out the robotic elephant in the room? Yes.

And should we extend ourselves and our teams grace when we slip into over-reliance? Abso-lute-ly.

Because every time we choose the AI interaction over the human one, we make the next human conversation even harder.

We're not just avoiding discomfort.

We risk atrophying the beautiful, messy capacities that make us indispensable to the future of work.

GO | DO

The Three Pillars to Lead as Human First

Not ‘skills AI can’t do’: more like ‘ways to stay upright when everything’s pulling you down the slope.’”

The Human Power of YET

When you can say, "I don't know yet, and here's how we'll figure it out together," you're not showing weakness. You're showing the gorgeous adaptive resilience every team needs when answers aren’t perfectly clear (read: now).

Research from 2025 confirms that leaders with high ambiguity tolerance drive more innovation and team confidence, even with equal access to AI tools. Why? Because they create psychological safety for their teams to experiment and to work through the grey areas together.

The MICRO DO Step: Embrace “I don’t know YET” in weekly meetings to practice naming uncertainty. 

Context Matters

AI might recommend the most efficient org restructure based on performance data. But a human leader knows why firing the "low” who mentors half the junior team would be a big mistake.

Combining algorithmic inputs with human override delivers higher decision quality and improved trust. And we need that right about now.

The MICRO DO Step: Add ‘context decision points’ to give space and time for humans to override AI recommendations.

Humans Are Present

AI simulates empathy. But it can't sit with you in your actual discomfort.

Not rushing to solve the problem, or defaulting to "let me ask the AI". Being great at being fully present separates leaders who retain talent from leaders who lose trust.

Research from 2024-2025 shows that teams with emotionally present leaders experience a 22-point boost in retention rates. Not because they have all the answers. Because they can stay in the room when the answers aren’t clear.

The MICRO DO Step: Add "Human-First Tech Agreement" to your next team meeting agenda. Start the conversation: "I've noticed I'm using AI more to support (or filter) hard conversations. Anyone else?"

What’s In It For All Of Us

When we build a strong foundation, we steady our stance on a very slippery slope.

By committing to weekly check-ins, practicing the hard human things, building team agreements that embrace human-first, we create teams with a better (more human) shot at navigating uncertainty.

Teams where people feel seen, not handled. We lead as humans first, which means staying human. Embracing our humanity.

And that's the version of us that doesn't just survive AI disruption.

🧍‍♀️ We shape what comes next, standing on a strong, messy, human foundation.

Quick favor: forward this email to a fellow human. The more we embrace leading as humans first, the healthier the future of work is for all of us.

Get In There

📊 Subscribe to The New Ambition for instant access to the complete subscriber vault: healthy leadership tools, templates, and frameworks updated weekly with resources shaped by subscriber feedback.

  • 🎧 Why ‘Just be more human’ is dangerous advice (562K views, released yesterday) Brené Brown: The Algorithms Have Forced Us Into A Hidden Epidemic on Diary of a CEO podcast. Brown talks algorithms, leadership, and why we're not actually good at being human right now. Perfect for your weekend walk or Tuesday commute. (90 minute listen)

  • 👓️ The Oddness of Remembering Fake Memories Andrew Deutsch on Substack (full disclosure, he’s my human brother). A fascinating deep-dive on MIT Media Lab research uncovering how AI-generated content creates facsimile memories that feel real-ish. If you've ever felt weird after interacting with an AI version of yourself, this explains why. (8 min read)

What's Your Stance on AI's Slippery Slope?

How's your embrace of your own humanity doing?

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If you’ve made it to the end of this cautionary tale, you’re my kind of human. I’d love to hear from you…have you ever chosen AI over a human conversation?

P.S. If you're at an inflection point and need an executive operator with a heart of gold and frameworks to define your success options, let's talk.

I work with a small number of executives and founders to build healthier success for their business and their leadership. Book a Fit Call to see if it's the right time.