Wisdom in a Wink
Inspiration, challenges, and tools to stay in demand as a leader.
From Trust to Co-Evolution: Learning With AI
Hi Leaders,
What if the real opportunity with AI isn’t just how we use it, but how we learn with it?
We’ve spent months exploring trust and balance in our partnerships with technology. Now, the next frontier is co-evolution. Not control. Not replacement. Mutual learning.
When we treat AI as a col...
by Katy Caroan —
Oct 17, 2025
ai
co-evolution mindset
leadership
From Passive to Powerful: Claiming Your Human Upgrade
Hi Leaders,
What if the real danger of AI is not being replaced, but replacing ourselves with shortcuts?
Every day, smart tools make life easier. Spellcheck fixes our words. GPS tells us where to turn. Algorithms serve up the next “perfect” choice.
Convenient? Yes. But when we hand over too much,...
Oct 02, 2025
digital dependency
human vs machine
reclaiming humanity
From Knower to Learner: Leading with Curiosity
Hi Leaders,
What if your greatest strength in an AI-driven world is not having all the answers, but asking the right questions?
Many leaders equate expertise with knowing everything. It feels safe, authoritative, and expected. But in reality, clinging to being “the knower” can limit growth.
Why T...
by Katy Caroan —
Sep 18, 2025
ai
leadership
learning
From Fear to Freedom: Rethinking AI’s Role
Hi Leaders,
What if the biggest myth about AI isn’t what it can do, but what it takes away?
We’ve been told the story: AI will replace us. It stirs fear and resistance. But here’s the truth: AI isn’t here to erase human value. It’s here to expand it.
Why This Shift Matters 🤖✨
AI excels at handlin...
by Katy Caroan —
Sep 04, 2025
ai
growth
unlearning
From “Aha!” to Always: Turning Training into Lasting Change
Hi Leaders,
What if the real test of a great workshop isn’t what happens in the room, but what happens after?
You’ve seen it: a training day full of energy, rich discussions, and bold commitments. Everyone leaves inspired. But back at the office, the daily grind creeps in. The ideas feel riskier....
by Katy Caroan —
Aug 14, 2025
growth
leadership
learning
The Leadership Mistakes No One Talks About—Until It’s Too Late
Hi Leaders,
You’re not new to this. You’ve earned your seat, delivered results, and built trust.
But lately, something feels...off.
Your ideas don’t gain traction.
Your name isn’t in the room.
Opportunities seem to go to someone else—someone louder, bolder, maybe even less qualified.
Let’s name i...
by Katy Caroan —
Jul 31, 2025
leadership
unlearning
webinar
Are You Working Hard Yet Fading Into the Background?
Hi Leaders,
What if the real danger to your career isn’t failure—but becoming invisible?
You’ve likely built your reputation on competence, consistency, and collaboration. And yet, something’s off. The recognition doesn’t match the effort. Your voice isn’t carrying. Opportunities go to others. It...
Jul 18, 2025
Ready to Practice Boldly?
Hi Leaders,
What if practicing—not just learning—is the missing piece to your next leadership breakthrough?
This summer, I’m inviting a few bold leaders to practice with intention, creativity, and courage. Are you one of them?
Why Bold Practice Matters 🎯
We don’t grow by playing it safe. We grow ...
by Katy Caroan —
Jul 03, 2025
bold leadership
unlearning
What Happens When Teams Feel Seen?
Hi Leaders,
Ever felt like your team should be clicking—but something’s off?Whether you're leading a board, an executive team, or scaling a fast-growing group, the real unlock isn’t in another strategic offsite. It’s in helping people feel seen, heard, and safe—so they can lead with confidence an...
by Katy Caroan —
Jun 20, 2025
Beyond Insight: Practice Makes Human
Hi Leaders,
We’ve all had that aha moment. A brilliant coaching question that stops us in our tracks. But here’s the truth most leadership programs gloss over:
✨ Insight alone isn’t transformation. ✨
You don’t become a better listener by hearing someone talk about listening. You become a better l...
by Katy Caroan —
May 30, 2025
The Surprising Power of Saying Nothing
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Hi Leaders,
In fast-paced teams and busy minds, silence can feel… awkward. But what if the quiet moments you avoid are the ones that unlock the clearest insights?
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Why It Matters 🔍
Silence isn’t emptiness—it’s a leadership tool.
It calms the noise, clears the clutter, and invites reflection.
W...
by katy caroan —
May 01, 2025
leadership
silence
unlearning
Unlearning to Move Forward
Hi Leaders,
What if your next breakthrough wasn’t about adding something new—but letting go of what no longer serves you?
That’s the power of unlearning. Not the easiest task, but one of the most powerful tools in a leader’s toolbox. Let’s get curious and dig into what unlearning can unlock for y...
by Katy Caroan —
Apr 17, 2025
beliefs
perspective
unlearning
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