When Managers get in the way: a Rooftop Lesson
There’s a rooftop restaurant in midtown Manhattan called The Haven. It’s the kind of place that sells an experience as much as a meal: city lights twinkling around you, the hum of conversation, the soft clink of glasses. My husband and I went there on a crisp Saturday evening (last weekend) ready to unwind and enjoy the night…celebrating his birthday.
The experience started strong. Our waiter was attentive without hovering- one of those rare gems who pays attention to details before you even have to ask. He noticed something small, yet huge: the three oversized appetizer plates headed our way would never fit on our tiny two-top. Rather than squeeze them in or let us juggle plates, he immediately offered a solution. “Let me move you to this four-seater right next to you,” he said, already setting the table for us.
It was seamless, thoughtful, and generous. A true hero moment. We relaxed. We laughed. We felt taken care of. The kind of service that makes you think, I’ll come back here again.
And then… it flipped.
Just as our entrées were about to arrive, the manager appeared. Not with a warm smile or an apology, but with an abrupt request frame as a “favor”: could we please move back to the smaller table? Another party “needed” the four-seater. The irony? There were still an empty two-seater nearby, along with this original one. My math still has 2+2 equaling 4…meaning he could’ve joined the two and let us enjoy our meal. The disruption was jarring- we were mid-meal, mid-conversation, and now mid-move.
In that moment, the glow of the evening dimmed. The waiter’s heroism was overwritten by the manager’s short-sightedness. The message to us as customers? Your comfort is less important than my seating chart. The message to the waiter? Your judgment doesn’t matter here.
What had been a wow moment became a why moment.
The BIGGER lesson
This isn’t just about a rooftop dinner. It’s a leadership trap I see in organizations everywhere. Managers feel the need to “step in,” to control the moment, to enforce policy, and in doing so, they erase the magic created by the people closest to the customer.
Frontline employees often see what leaders don’t. They anticipate problems, smooth rough edges, and create those small sparks of delight that customers remember long after the transaction. When managers overrule those instincts, they don’t just disrupt the experience, they crush initiative. They tell employees: don’t bother noticing, don’t bother acting, because someone above you will undo it anyway.
And customers feel it. They feel the difference between being cared for and being managed.
The TAKEAWAY
Leadership is not about inserting yourself into every decision. It’s about knowing when to stand back. Sometimes the best way to lead is to let great judgment play out. Protect your employees’ hero moments. Amplify them. Celebrate them.
Because it only takes one poorly timed interruption to unravel ten good experiences.
At The Haven, we walked in expecting a memorable night. We left with a reminder: managers can make or break not just a meal, but a moment.
