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February 07, 2024

50 Conversations in 50 Days

Towards the end of last year, the team and I set an ambitious goal: Host 50 conversations with people leaders across industries — all in the final 50 days of the year.

We wanted to both understand how executives and teams were navigating the ongoing changes in the workplace, and offer a safe space to reflect on their year together. Also as I continue leading this work, I knew I needed to put myself in the place of a “student” and listen to how others are helping their teams grow.

Most of these leaders were friends who’ve worked with Experience Institute or have inspired our work, so there was a prior relationship and trust. This wasn’t just some “research study” — it was more of a listening tour full of heart, deep reflection, and care. Below, I’ve summarized the incredible lessons that came from those honest conversations. Let’s dive in:

Theme 1: Do whatever it takes to make work more human.

First, there was a resounding emphasis on empathy and fostering deeper personal connections in the workplace. During many of our conversations, we spoke about the importance of understanding the personal and professional challenges faced by leaders and the need to create space for one another to have an open, honest dialogue without judgment or fear.

More executives than ever are prioritizing wellbeing initiatives. There is a growing recognition that a healthy team is paramount to vibrant cultures, great work, inspiring innovation, and great collaboration. In other words, if people don’t feel like people, they break. It’s not just bad for business, it’s bad for everyone.

Theme 2: The best way to handle change is to create space for it.

So many challenges have surfaced over the past few years that are requiring teams to adapt faster than ever. Many conversations included discussions of market changes, technological advancements, and global uncertainties. The solution we heard most was to create a consistent space for teams to work on the future of their companies amidst these changes. In these spaces — often leadership & development programs — teams who are invited to think creatively and pursue new ideas often rise to the occasion and bring others along with them. In other words, agility starts with the space and resources to try things differently.

Theme 3: Different is good. Really good.

Even though some leaders voiced concern around the lack of action in org-wide diversity initiatives— there was a real sense of joy and meaning around these efforts. Leaders acknowledged the value of diverse perspectives in driving better outcomes across their businesses and fostering workplaces that are more vibrant and full. And there is a palpable desire to continue advocating for inclusion and belonging because of both the short & long term impact those programs can have on people, teams, and society. Of course, there were some challenges here too: ongoing buy-in, competing priorities, and challenging retention numbers for People of Color. But the message was clear, diversity is worth fighting for.

Theme 4: Growth begets growth. Stagnation begets stagnation.

During the end of my conversations, I would always ask about the person’s next “Leap.” The responses ranged from audacious sales goals to learning pottery and everything in between. AND there was often a bit of longing in their eyes — a sort of hope that they would really make time for their Leaps throughout their full schedules.

This often led to conversations around asking for support, coaching, and looking for ways to bring others along for the ride. We spoke about how there was a lingering two-sided nature to their work — supporting the growth of others and neglecting their own. By the end, there always seemed to be a new spark to recommit to their ideas. Not just for themselves, but for the sake of their teams and communities, too.

Theme 5: AI is big. But you can start small.

As you might imagine, AI took up a lot of the airwaves. Leaders who work in tech were well into their roadmap of implementation, but still feeling behind. While those in manufacturing and professional services had mainly built experiments or committees and this year was going to be their year to really dive in. The main areas of AI exploration were: streamlining ops, enhancing customer experience, and widening creativity.

There was a sense of urgency in our conversations, but we also discussed the distraction that technology can be in both time and money. The most confident leaders had a pulse on their customer first and that created a steady hand for choosing initial, worthwhile experiments.

Theme 6: Finding meaning at work isn’t a task — it’s a muscle.

The past few years have caused people to work harder than ever. In many cases, this is due to fear or uncertainty in the market as opposed to an exciting vision and sense of personal/professional purpose. During these conversations, many of the leaders discussed ways to reset their own work, and their broader teams’ work on the “why.”

More importantly, we noted how this isn’t a one-time effort, but needs to be baked into the rhythm of work — 1:1s, performance reviews, offsites, learning programs, etc. It’s easy for people to lose sight of what’s driving their efforts, and the more buried that purpose becomes, the faster burnout can set in.

Theme 7: Less noise, more signal.

One of my last questions to leaders was simply, “What do you need most to support your work?” Most people mentioned being inundated with too many messages, too many meetings, and programs that were too disparate and disconnected from their most pressing issues.

What they were most interested in was smaller, focused communities of like-minded leaders — often within or near their companies — combined with helpful research that supports their work. They often referenced Ei’s writings and programs as a bright spot, and it made us more excited than ever to produce more relevant content, and help companies design cohort programs focused on Leaps they can take together.


Of course, there was more; but these are the ones that stood out to us and seemed most top of mind among the people who shared.

If you were one of the participants, thank you for your time, your care, and your work. The team and I are so inspired by you and feel grateful to be in your corner this year.

And if you’re a People Leader, let us know if you’d like to share a call about your work, your lessons, and your needs this year. We’re rooting for you, too.

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