It’s 12:37 am, and I just closed my laptop after three hours of playing with a new AI tool.
Not because I had to. Because I wanted to see what it could do. And honestly? It’s wild how fast this stuff is moving. Every week, there’s something new that makes you rethink how you’ve been working.
That’s what’s keeping me up tonight. Not fear. Excitement mixed with this weird realization that everything I thought I knew about leadership is shifting under my feet.
When It Started Clicking
I had coffee with a 26-year-old founder last month. Her company does in three clicks what takes most companies seventeen steps and two departments.
She wasn’t showing off. She just asked, “Why do companies make this so complicated?”
And I realized: we do. We overcomplicate everything because that’s how it’s always been done. But what if it doesn’t have to be?
That conversation changed how I’ve been thinking about our own processes. We’ve been building AI into our workflows for months now, and the biggest barrier isn’t the technology. It’s getting people to unlearn the old way of doing things.
Including me.
What I’m Learning Fast
Here’s what’s becoming clear: the leaders who are winning right now aren’t the ones with all the answers. They’re the ones willing to experiment, break things, and admit when something isn’t working.
Satya Nadella did something brilliant at Microsoft. He started inviting founders from tiny acquired companies to executive strategy meetings. Not to present. To participate.
That’s genius. Because the best ideas aren’t coming from the people who’ve been doing this for twenty years. They’re coming from people seeing problems with fresh eyes.
I’ve been doing this with our team. Bringing in people who normally wouldn’t be in the room. The conversations are messier. But they’re also ten times more valuable.
The Shift That Changed Everything
I used to run meetings like checkpoints. “What’s your status?” “Why are we behind?” “What’s the plan?”
Then I read about Jean-Philippe Courtois at Microsoft killing their “inspection culture” meetings. He replaced them with coaching conversations. Listening. Actually helping instead of just checking boxes.
I tried it. First meeting felt weird. I wasn’t grilling anyone. I was just… talking. Asking what they needed. Where they were stuck.
Two weeks later, one of my managers told me it was the first time in months they didn’t spend the night before a meeting preparing defensive slides.
That hit me. We’d been wasting so much time on performance theater instead of actual work.
What’s Actually Working
I’m using AI tools every day now. ChatGPT for brainstorming. Claude for writing. Various tools for data analysis. Some days I feel like a kid in a candy store.
Walmart’s chief people officer admitted she uses ChatGPT for everything from executive searches to travel planning. I love that. She’s not hiding it. She’s using the tools, learning from them, and being transparent about it.
That’s the energy. Not “I’m threatened by this.” But “let me figure out how this makes everything better.”
Last week I tested a new tool in a team meeting. Messed it up twice before getting it right. Everyone laughed. Including me. Because it’s okay to be learning in public.
That’s the shift. We’re all learning together. And the leaders who pretend they’ve got it all figured out are the ones falling behind.
What I’m Seeing (That Worries Me)
I’ve watched companies announce big “AI transformations” and then… nothing changes. Because the CEO gave a speech, handed it to IT, and walked away.
It fails 73% of the time. Not because of bad technology. Because transformation isn’t a project you delegate, it’s a mindset shift that starts at the top.
I’m in this every day. Testing tools. Asking questions and breaking things. Because if I’m not willing to do it, why would anyone else?
What I Actually Believe
Leadership right now isn’t about knowing everything. It’s about being curious enough to learn everything.
It’s about building teams where people feel safe to experiment. Where asking “what if we tried this differently?” isn’t met with “that’s not how we do things.” Where the best idea wins, regardless of who said it.
We’re in the middle of the biggest shift in how we work that I’ve seen in my career. And honestly? I’m having the time of my life figuring it out.
Not because I have all the answers. Because I’m asking better questions. And the people around me are too.
That’s the game now. Stay curious. Stay humble. Keep learning.
And maybe post your thoughts at 1 am when you probably should be sleeping.
Rupesh Sanghavi
Cloverbites By Rupesh Sanghavi 
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