Last weekend, my sister and I pulled off a big surprise party for our mom—and she was completely shocked!
Friends and family came together, kept the secret, and helped us create a moment of pure joy. But here’s the thing: the magic wasn’t just in the surprise itself—it was in the anticipation of the big event.
We spent hours imagining how she might feel, who should be there, what details would make her feel most seen and celebrated. The thoughtfulness behind the scenes is what ultimately made the surprise unforgettable.
And it got me thinking: leadership is a lot like planning a surprise party. The thoughtfulness that goes into planning an event is at the heart of intentional leadership.
Throughout my career, I’ve had the privilege of designing and facilitating programs for students, founders, and leaders. At the heart of this work has always been a focus on creating meaningful, memorable experiences. Whether it was curating surprise retreat activities or sending specially crafted gift boxes, I’ve learned that the element of unexpected delight can leave a lasting impact. Behind each moment was a lot of intentional planning, always rooted in the desire to align the experience with purpose and to meet people with something they didn’t see coming, but deeply appreciated.
Great leaders don’t wait for someone to ask for help. They anticipate needs before they’re voiced. They read between the lines, act with empathy, and lead with strategic foresight. They plan not just for efficiency, but for meaning.
When leaders anticipate, they show up in ways that make a difference:
✨ Proactively care
✨ Put emotional intelligence in motion
✨ Guide with strategic foresight
✨ Create moments of delight
It’s the difference between reacting and responding with intention. Between managing the moment and shaping the experience.
At a surprise party, anticipation makes someone say “You thought of everything.” That’s leadership at its best.
When was the last time you planned something with someone else’s joy in mind? How often do you pause to imagine what someone else might need before they ask? Who in your world deserves a “you thought of everything” moment? How do you show up in the moments that matter? Where are you leading with intention vs. habit?
LEADERSHIP & CULTURE
How to Navigate the Biggest Pitfalls of a Growing Business ⚠️
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From hiring mistakes to culture shifts, join Inc. and a panel of founders and leaders for a breakdown breakdown of the most common pitfalls in growing a company and how smart leaders handle them.
ENTREPRENEURSHIP
Startup Ignition Podcast 🎧
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Startup Ignition provides resources and community for ambitious entrepreneurs and visionary startups. Hosted by John and Tyler Richards, this podcast helps to fuel bold startup dreams through founders’ stories and experiences.
INNOVATION
Are you AI ready? 🤖
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AI is already in your inbox, embedded in your workflows, and shaping industry strategies. The real question is: are you harnessing its full potential or just skimming the surface?
Join the Small Giants Community and the Trybl team for a free, hands-on workshop designed to meet you where you are. Walk away with the clarity, practical tools, and confidence you need to use AI with purpose and intention.
PERSONAL GROWTH
Negotiating Salary 💵
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Learn key salary negotiation techniques and how to improve your bargaining skills from Harvard Business School with this free 15-minute online lesson.