What Great Leaders Do Between Big Milestones

The applause is deafening. The annual kickoff is a hit. Everyone’s high-fiving, the goals are locked, and the energy is so contagious you could probably power a small city with it.

Fast forward six weeks: that buzz has fizzled. The team’s knee-deep in email threads and budget spreadsheets, and suddenly no one’s cheering. The excitement didn’t disappear—it just…wandered off like your New Year’s resolution to hit the gym.

I used to think leadership was about nailing those big moments: the launches, the offsites, the all-hands where you hire a guest speaker who probably charges more than your car is worth. But here’s the secret I wish someone told me years earlier:

👉 Culture isn’t built in bursts. It’s built in the everyday, ordinary, sometimes boring moments between the spotlight events.

The Myth of Event-Based Culture

We’ve all been trained to think culture happens at events. And yes, events add to culture, but they aren’t (and shouldn’t be) the only culture strategy you deploy.

Culture actually lives in things like:

• That Tuesday morning stand-up where everyone looks a little sleepy.
• The awkward silence before the meeting actually starts.
• How you respond when a deadline is missed.

These “in-between” moments are where trust gets built and values actually stick.

Small, Consistent Actions > Big, Flashy Gestures

During one rough quarter, I realized we were far from our next milestone. Energy was flatlining. So I experimented with little things. Spoiler: they worked better than another expensive offsite.

Here are a few ideas to adapt for your own team:

Win Wednesdays (or Gratitude Fridays)

Spotlight one small, specific action from someone on the team:

• “Sarah stayed late to help debug code.”
• “Marcus asked the brave question we were all secretly thinking.”

These weren’t KPI updates…they were human moments. And they had ripple effects on motivation.

The First Five Minutes

I started every recurring meeting with something fun. A quick round of “weekend highlights.” Or a ridiculous “would you rather.” (One Tuesday, we debated whether to fight one horse-sized duck or 100 duck-sized horses. Productivity? Solid. Connection? Off the charts.)

The Check-In With “No Agenda”

Once a month or quarter, try to book 15-minute 1:1s just to ask: “How are you, really?”

No performance reviews. No project talk. Just listening.

One person later said those tiny check-ins were why she stayed. That’s retention strategy 101—forget foosball tables. (Want more prompts? Try an energy audit to spark ideas.)

Connection Doesn’t Need a Budget Line

Leaders sometimes overcomplicate this. They think culture-building requires a giant initiative. In reality, it’s the little gestures that land:

• Asking an engineer about his kid’s first day of kindergarten meant more than our last happy hour.
• Using something like Confetti’s Meeting Kits turned a dull budget review into a surprisingly fun session by starting with: “What was your childhood dream job?” Suddenly, we weren’t just coworkers crunching numbers—we were former wannabe astronauts, ballerinas, and marine biologists.

These things often take just two minutes. And they matter more than a balloon arch at the next offsite.

Why the In-Between Matters

Big milestones are fun. They photograph well. They make the company look shiny on LinkedIn.

But loyalty? Loyalty is built when:

• You remember someone’s coffee order during crunch time.
• You publicly thank the person who always takes meeting notes.
• You own your mistakes in front of the team (instead of playing corporate dodgeball).

Start ridiculously small. Trust me: it works.

• Add a two-minute “human moment” to the start of one meeting.
• Pick one day a week to celebrate a tiny win.
• Schedule one no-agenda check-in a week with a different team member.

Perfection isn’t the goal. Consistency is. Your people don’t need you to be a motivational superhero. They need you to be human. Regularly.