The hard truth about making a workplace “great”. By Leanne Prewitt.
Creating a great place to work is one of the hardest things leaders can do. It requires balance between business needs and employee expectations, between intention and perception, between what seems fair and what feels fair. It’s a constant negotiation and even with the best of intentions, you can still get it wrong. I know this firsthand.
At Ervin & Smith we close our offices between Christmas and New Year’s for an extended winter break. It’s a beloved tradition that gives everyone time to relax, recharge and start the new year fresh. Our team values it, expects it and frankly, so do I. Last year however, I learned a valuable lesson about leadership, culture and the limits of good intentions.
The 2024 holiday schedule presented an awkward quirk: our winter break was set to begin on Tuesday, December 24 which meant that Monday, December 23 was a lone workday before an extended closure. Like many of my employees, I didn’t particularly want to work on the 23rd. But we had already planned to close for 19 days that year — a generous benefit — so simply canceling the workday wasn’t an option.
Then, I had what I thought was a brilliant idea.
We have a policy called Flexible Fridays where we block off Friday afternoons from meetings so team members can use the time as they see fit. For most, this means starting the weekend early. It’s a perk that fosters balance and autonomy and people love it. Seeing three Fridays in December, I proposed a swap: if we worked full Fridays leading up to break, we could take off the 23rd. Three solid workweeks in exchange for an uninterrupted holiday.
I ran the idea by my executive team who couldn’t come to consensus on what the team would want. We came up with the idea to let the team vote on it, thinking this was a collaborative way to gauge interest. If people wanted the 23rd off, great. If they preferred to keep their Fridays flexible, that was fine too. Our director team thought the vote was a good idea. Confident in my solution, I presented it to the broader team.
I was not prepared for the response.
Almost immediately, private messages started trickling into managers. In the public Teams meeting, silence. Then, questions: Was this fair? Weren’t we giving up more than we were getting? Was Flexible Friday actually flexible if it could just be taken away? What I had thought was a creative solution to a scheduling quirk felt to some like a penalty. It didn’t matter that my intent was good — the impact was different. And as a leader, I had to own that.
I responded quickly. I sought direct conversations with those who had concerns. I acknowledged the unintended impact of my decision and clarified my intent. And ultimately, I honored the results of the vote — which, to my surprise, ended in a perfect tie. Half of the team wanted to take the 23rd off, half wanted their Flexible Fridays. With no clear consensus, we made no change. The 23rd remained a workday, my ego took a hit and we moved on.
It’s a joke now — whenever a tricky decision comes up, someone inevitably says, “Is this another December 23rd situation?” We laugh, but the lesson stuck with me. Leadership is full of moments like this — where what you think is a smart, well-intentioned decision lands completely different than expected. The real test isn’t about getting everything right all the time. It’s about how you handle the moments when things go wrong.
You can’t make everyone happy all the time. But you can listen. You can take responsibility. You can repair trust. And sometimes, you can even laugh at yourself. That’s what makes a company a great place to work — not just the policies and perks but the resilience, trust and honesty in how you lead.
My partners and I don’t have it all figured out. But if we’ve learned anything, it’s this: A great workplace isn’t built on perfect decisions. It’s built on how you respond to the imperfect ones.