Is AI Making Your Leadership Feel Less Human?
Welcome to Love Mondays - your weekly dose of practical tools and fresh thinking to help you lead through change, build better teams, and make every Monday matter.
If you want to go behind the scenes of the big conversations I’m having with global leaders and change-makers, join the newsletter list for Conversations That Matter here.
A team member sent me a reel recently that made me laugh: set in 2050, two people are standing face-to-face…but instead of talking to each other naturally, they’re whispering prompts into ChatGPT first, waiting for the app to tell them what to say next.
Funny, until you realise it's not that far-fetched. I'm thinking it's more 2030 with an AirPod feeding you AI-generated lines in real time. But maybe we're talking even sooner than that.
Just last week, a friend told me how they’d started noticing AI-generated replies sneaking into text conversations - especially when things got a little tense or the subject matter became a bit too deep. The words were smooth and perfectly phrased. But they didn’t sound like the person.
I've been noticing the same trend creeping into workplace communications. Messages that hit all the right notes but somehow feel... hollow. Because increasingly, they are.
The future of “outsourced conversation” isn’t decades away. It’s creeping in right now.
The Muscle We're Already Losing
Conversation is quietly disappearing from the workplace:
Real-time conversation is becoming optional - even awkward. That’s a problem because conversation is a muscle. And the less we use it, the weaker it gets.
And now with AI, we may be skipping the reps entirely. If hard conversations are delegated to tools, prompts, or scripts - when do we learn to lead through discomfort? When do we build the presence, empathy, and resilience that leadership requires?
The stakes are higher than efficiency. We're talking about the fundamental ability to have human conversations that build trust, create clarity, and move people forward - conversations that no algorithm can replicate.
"The art of communication is the language of leadership." - James Humes, author and former presidential speechwriter.
How to Lead in the Age of AI — Without Losing Your Voice
Gallup’s research found that the #1 factor for strengthening team communication is the manager.
And LinkedIn data confirms that while AI literacy is the most in-demand skill of 2025, the skills rising alongside it are distinctly human: conflict resolution, public speaking, customer engagement and support, and innovative thinking.
The future isn’t either/or. It’s both. The leaders who will thrive are the ones who know when to lean on technology and when to lead with humanity.
So how do we keep the human edge in leadership while embracing the tools that make us more efficient?
1. Design for Connection, Not Just Efficiency
Yes email is more efficient, but not everything should be typed and sent. If what’s being discussed impacts how people feel, collaborate, or trust each other, it deserves more than a message. It deserves your presence, your attention, and your willingness to slow down and show up.
Efficiency matters, but leadership is relational. The most effective leaders know when to shift from quick communication to meaningful conversation. And the only way to stay confident in real-time conversations is to keep having them.
Next time you're about to write it out (or ask AI to), ask yourself: Could, or should, this be a conversation instead?
2. Prep With AI, Show Up Human
AI can be a powerful tool to help you prepare for important conversations - whether you're giving tough feedback, navigating change, or aligning your team. Use it to think through scenarios, anticipate objections, and organise your thoughts before you step into the room.
You might ask things like: "What are three key points I need to cover?" "How might they push back on this decision?" "What's the best way to frame this feedback?"
Once you're in the conversation, set the AI aside. Real leadership happens in the moment - listening actively, adjusting based on what you hear, and showing up with emotional intelligence.
The Leadership Work That Can’t Be Automated
I keep coming back to this: as AI gets smarter, what becomes more valuable are the things it can’t do for us.
The check-in that builds trust. The question that sparks a new idea. The conversation that clears the air. That’s where leadership happens. Conversation isn’t just how we communicate. It’s how we lead.
Just this morning I had breakfast with a CEO who makes a point of personally taking team members who leave the organisation after significant periods of service out for lunch to say “thank you”.
He showed me a truly moving text message he had received from an employee who was leaving after 17 years: a heartfelt note about how much those personal touches, like that one, had meant throughout their working journey.
He could have delegated this. HR could have handled the farewell process. But he understood that some leadership moments require your actual presence, not just your signature on a card. And in an age where everything can be automated, scheduled, and optimised, he chose to show up personally. That's the irreplaceable human work of leadership.
Working across fitness, events and energy transition. I’m creating a wild & varied work-life with the goal of challenging myself & adding value at every turn.
2wHaving listened to lots of podcasts around this recently the word that comes to mind for me is "balance". CHAT GPT is my regular go-to but I've realised that if I use it to write messages entirely, it will stop feeling like me and the communications won't be truly authentic. It certainly makes life easier and maybe I will learn and eventually be able to write as well as it does but I've decided to use it mindfully and hopefully that will keep me on track with it.
Creative Connector | Optimizing people-centered systems by blending structure, creativity, and care - bringing people, ideas, and details together like a mosaic.
3wHolly, your Love M❤️N DAYS series always fuels my week with fresh perspectives and keeps me thinking about the conversations that matter most in leadership I’ll happily let AI help me prep, but the best leadership moments still come from showing up human - messy, real, and full of trust.
Director | Technical Strategist, Digital Marketing, Digital Transformation and AI Automation
3wWhat 🙀 yes, 🙌 I actually said it.
Director | Technical Strategist, Digital Marketing, Digital Transformation and AI Automation
3wIt’s called #talking #emotion
Founder Honeysweet Creative and Transnational Space Alliance Summit
3wThank you Holly. I love this. I am finding AI to be an invaluable tool but, for years, I have been urging my younger colleagues to pick up the phone, stroll into the office, get face to face. 90% of the time a situation that is involving 15 back and forth texts or emails can be dispatched successfully in a 3 minute (and usually pleasant) conversation. A thought to share: joining a volunteer service organization like Rotary International does several things: 1) allows you to engage with your community 2) provides a forum in which to grow as a leader as one joins committees or gets involved in leadership and 3) offers you a chance to meaningfully serve humanity through any number of projects in which that club is engaged. The art of in person collaboration is nowhere more practiced and rewarding.