Cultivating Connection: The Power of ‘Woulda Coulda’

a pair of shoes with two arrows pointing in opposite directions representing a choice and connection

Picture this scene: 20 eager leaders, many of whom were meeting for the first time, gathered in the room. The air was charged with an electric energy, yet the sense of connection among them was tentative at best. The initial awkwardness of such first encounters was all too familiar—a scenario I’ve encountered countless times throughout my career.

In today’s whirlwind of a world, where digital interactions often overshadow face-to-face connections, it’s easy for workplaces, and the relationships within them, transactions rather than meaningful interactions. But here’s the thing: it’s the depth of our connections that can turn a group of strangers into a tight-knit community of allies and friends at work.

Here’s what our research at SkyeTeam has continued to demonstrate: the cornerstone of any thriving workplace is the authentic connections among its people, which pave the way for collaboration, empathy, and lasting friendships. Relationships matter!

As Michelle Johnston and I launched the new leadership program, we were deeply aware of this disconnect. Our goal was ambitious yet clear: to weave a tapestry of connection in less than an hour!

Our secret weapon? A seemingly simple icebreaker and connection exercise I cheekily dubbed ‘Woulda Coulda.’ This wasn’t just about warming up the room; it was about cutting through the professional veneer to uncover the rich, personal stories each leader carried with them. To empower us to own, and share our stories and life journeys (well a snippet of them).

Fostering Connection

Here’s the lowdown: We asked everyone to flit from person to person, sharing their responses to a couple of seemingly simple questions:

  1. Woulda – “What did you dream of becoming as a kid?”
  2. Coulda – “Ever faced a fork in the road, a real game-changer moment in your life or career?”

It was fun to see the activity play out. The room was buzzing! This activity quickly moved from simple, to deep as people shared their stories. There was laughter, the occasional “me too!” as everyone unpacked their life’s suitcase. More importantly relationships were nurtured. Connections were cultivated and it created the space to nurture genuine relationships, setting the stage for a transformative leadership experience where we’d all be #bettertogether.

To help set the wheels in motion I shared my own ‘Woulda Coulda.’ Buckle up; here they come.

Woulda: The Dream of Open Roads

My Woulda? I had many career aspirations when I was little. However the one that I chose to share was my grand plan of becoming a long-distance lorry driver. Yep, you read that right. It was the promise of seeing the world that appealed to me! Fast forward to now, and while I’m not driving a truck, I’ve managed to globe-trot across more than 20 countries. In a way, I’m living my own version of that dream, sans the lorry!

Coulda: The Leap Across the Ocean

And the Coulda? This one’s a bit closer to the heart. It was the decision to move to the USA. Talk about a leap of faith! We left the familiarity of being close to relatives, trading it for the unknown thousands of miles away. It was challenging at times. But looking back, I wouldn’t change a thing. That choice was the domino effect that led me to New Orleans. To meeting Michelle, and to the incredible group we’re working with today. If I’d played it safe, who knows where I’d be?

Forging Deeper Connection: The Power of Sharing Our ‘Woulda Coulda’

So, why am I sharing all this? Because ‘Woulda Coulda’ turned out to be more than just an icebreaker. It was a reminder that our paths are woven from our dreams and the choices we make. It’s about the roads we travel, the detours we navigate, and how they shape us into the leaders we are today.

Now, over to you. What’s your ‘Woulda Coulda’? Ever think about that dream job as a kid? Or that pivotal moment that could’ve rerouted your life’s GPS?

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