How I Think About Employee Engagement as a Former Operator

From my previous roles—VP of Learning & Community, Head of Operations—I know what managers and leaders are up against. Each company, and certainly each leader, has their own take on what "Teambuilding" means.

We all know it’s important to have a team that is engaged, connected to the mission, and growing their skills. We certainly know how important it is to retain our best talent. But in the midst of week-to-week sprints and quarterly cycles, it’s easy to miss just how simple it can be to strategically build on your team culture.

As a company culture and meeting nerd, here are three ways I used to build meaningful connection without adding more "work" to the calendar:

1. Create Rituals for the time you already spend together

Start by changing the way you use the time you already have.

• The "5- Min After" Rule: Explicitly state that the meeting starts at 5 minutes past the hour, and the first 5 minutes are for random commentary or catch-up. This tends to happen anyway, so stating it as an intentional norm works wonders.
• Gratitude Shoutouts: Start the meeting with a values-based shoutout or rotate who leads an opening question each week.
• The Coffee Closer: When the agenda allows, wrap 10 minutes early and randomly assign breakout rooms for an optional “virtual coffee” pairing for those who can stay on.

2. Lead with Questions

Where it makes sense, ask your team for input often. It sounds simple, but shifting from telling to asking is the fastest way to build a culture of ownership. Try questions like:

• "What do you think would make us a stronger team?" or "If we were to do something to help us grow our skills as a team, what do you think the team would appreciate most?"

The Pro Move: I’m a huge fan of scaling questions, which I both teach and model in my Communication Skills workshop. Instead of a broad "How is everyone?", try: "On a scale of 1-10, how connected do you feel to the team these days?" The magic is always in the follow-up: "What would it take to move that number up by just one point?"

3. Build in space for internal networking through a “Cross-Team Connect”

In larger meetings like All Hands, we used an 8-minute ritual to strengthen cross-team relationships and recognize personal wins that won’t show up in a slide deck (like buying a home, finally mastering the perfect latte, or becoming an auntie).

• The Ritual: In a live breakout to either start or end the meeting, employees share a win or answer a question prompt, with each person giving their partner a public shoutout in the company recognition channel. It’s the right amount of structure to make peer recognition scale.

From Building Teams to Facilitating for Them: What I’ve Learned

After leading 100+ workshops with over 2,500 participants, I’ve observed two things that are vital for leaders to know:

• People are never more engaged than when THEY are the ones talking. In my sessions, I call on people—not like law school, but in a way that is warm and unintimidating, even for the introverts. There is so much wisdom in your employees; sometimes hearing from each other is more valuable than hearing from an outside expert.
  
• Choosing a facilitated experience allows YOU to be a participant. It is really hard to break out of your usual leadership role. Bringing in a facilitator allows you to listen to your team and join in alongside them. It shakes up the day-to-day norms and allows you to show up with your colleagues as a peer.
  

What participants are saying:

"This was mind-blowing how much I didn’t know I didn’t know about questions...Game changer for sure." — Nancy N.

"Mollie was great! Super engaging, kind, approachable...She's got a great demeanor and we're really happy with how the event proceeded." — Cristina with YAPI

"I've always considered myself a decent conversationalist, but majorly guilty of the conversational mis-step you mentioned. Thanks for being a bright spot in my day!" — Shannon

I’ve polled every group I’ve led, and the average appreciation score for these kinds of learning experiences is 4.6 out of 5. Employees feel cared for when you spend an hour (or even a "power half hour") together to pause, develop skills, and apply something new. I recommend a quarterly learning event for every team—it pays dividends.

If you’re ready to get something on the calendar, here are three experiences I lead with Confetti:

• Communication Skills: Learn question techniques and avoid the conversational missteps we all make.
• AI Prompting 101: Stop "guessing" with AI and start building better prompts together.
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• Custom Values Workshop: A deep dive into how your team actually lives out your company mission.

Employee engagement doesn’t require a massive program, a new platform, or a packed calendar. It’s built in the moments you already have—how you open meetings, the questions you ask, and whether people feel seen, heard, and invited to participate. As a former operator, I’ve learned that the most effective cultures are designed with intention, not excess. When you create space for real dialogue and shared experience, engagement stops being an initiative and starts becoming how your team works together every day.