Actually Caring: The Engagement Strategy Corporate America Forgot

Written by David Drees, Principal Consultant Culture Wins

Alright, let’s be real—most so-called “engagement strategies” are about as thrilling as a corporate compliance meeting on a Monday morning. If we’re still calling them “engagement strategies,” we might as well be reading off a boring HR script. Let’s be honest, we deserve better. People deserve better.

So, let’s scrap the jargon and get down to the real deal: Radical Empathy and MicroMoments—two powerful (and dare I say, spicy) concepts that make a difference in how we connect, lead, and thrive in our workplaces and beyond. If you’re looking for some beige, HR-approved talking points, you might want to take a detour. But if you’re ready to shake things up, let’s go!

Radical Empathy: Because Basic Empathy is Weak Sauce

Empathy is en vogue right now, caring about people always is right? Right…? Well it should be!

…But radical empathy? That’s where the magic happens. Radical empathy goes beyond just understanding someone’s feelings—it’s actively feeling with them, seeing the world through their lens, and showing up for them in a way that actually matters.

Imagine your coworker, Sarah, is having a rough day. Regular empathy might say, “Oh no, Sarah looks sad. Maybe I should send her a Slack note that says “I hope you have a great day!”

Radical empathy says, “Hey Sarah, let’s grab a coffee. Give me a two-word check in? How can I actually help?” See the difference? One is lip service; the other is human connection. (Also, I stole the two-word check in from Brené Brown – she’s so damn smart – steal it here too - 2-Word Check In)!

Can we make it practical? Sure can! But if you are looking for the next viral post… this is not it, it’s just good old fashioned “giving a shit”:

Be All In – Put the phone down, lean in, and actually listen—people can tell when you’re half-present.
Say “I See You” – Acknowledge struggles instead of brushing them off; sometimes, people just need to hear, “That’s tough. That really sucks and I am sorry.”
Make Recognition Count – A generic “great job” won’t cut it; celebrate people in ways that actually matter to them. But also people LOVE letters, handwritten, personal, genuine mail – I mean it, throw it in the mail box!
Own Your Oops – Messed up? Admit it. Leading with honesty makes it easier for everyone else to do the same.

Micro-Moments: The Tiny, Mighty Game-Changers

Big flashy company-wide events? Meh. They’re nice, but they’re not what people remember. What sticks with us are micro-moments—the tiny interactions, the everyday gestures, the small but mighty acts of connection that happen in the cracks of our days.

Think about it:

The manager who actually remembers your dog’s name and asks about him.
The barista who knows your order before you even say it.
The colleague who gives you a genuine “How are you?” and actually listens to the answer.
The boss who recognizes your effort before you have to wave your own achievement flag.

These are the moments that make us feel valued. And here’s the kicker—they’re free. No budget meetings, no executive sign-off needed. Just people choosing to give a damn in real-time.

Tell me if you’ve heard this before… it’s 2021 in a hospital and shockingly the staff, the nurses, the doctors are burned out worse than a Looney Tunes character exploding from TNT. One suggestion I had for Sr. Leadership was to show up during the nightshift with coffee and conversations.

Fast forward… the CEO shows up at 7:30pm – right after the day and night shift turnover. Everyone is frantic, no one is in the mood to “babysit” the CEO, it’s a real loser…

Fast forward another week to 2:30AM – Now the CEO shows up again, with coffee and a smile. Walking around the quiet halls, asking nurses about their families, asking staff about their favorite sports teams from the medical bandanas they are wearing, asking doctors how they are doing…

Guess how it went now? Do it, guess?!

AMAZING, absolutely amazing. Why? Because the CEO didn’t take the short cut to the night shift at 7:30pm, but now he came in the dead of night, with coffee, and no agenda. Minds blown. Micro-moments made. Huge win. Every time he does it, it shows up in surveys, on social media—it’s HUGE!"

Why This Matters (And Why You Should Care, Like, Now)

You know what’s more effective than another leadership webinar or company retreat? Actually building a culture where radical empathy and micro-moments aren’t buzzwords, but everyday habits. And here’s the thing:

Connection is currency. People don’t stay in jobs just for the paycheck anymore. They stay for how they feel at work.
Engagement is a side effect. You don’t force engagement; you create conditions where people naturally engage because they care.
The best cultures aren’t built in boardrooms. They’re built in hallways, Slack DMs, post-meeting side chats, and those tiny, thoughtful moments that make people feel like they belong.

Cool Ideas You Can Actually Use (Not Just Nod At)

So now that we’ve established that radical empathy and micro-moments are the real MVPs, what do we actually do with that?

Glad you asked. Here are some ridiculously simple but powerful ways to put these concepts into play:

1. Micro-Moment Meetings

Stop making every interaction feel like a TED Talk audition. Instead of long, drawn-out check-ins, try micro-moment check-ins—quick, casual, meaningful conversations that don’t require a calendar invite. A simple “What’s lighting you up right now?” can spark way more connection than a robotic “Any blockers?” (Vomit Emoji)

2. Ditch “How Are You?” for Better Questions

“How are you?” has become a throwaway question. Instead, try:

“What’s something awesome that happened this week?”
“What’s a win—big or small—you’re proud of?”
“If today was a movie title, what would it be?”

Let’s be kickass question askers!

3. Recognize People for Who They Are, Not Just What They Do

Sure, shoutouts for work performance are great, but what about recognizing someone for their energy? Their humor? Their ability to lift up a room? Call it out. Celebrate it. People want to be seen for more than their output. (Say it louder for the people in the back!)

4. Make Room for the Weird and Wonderful

Create space for personal expression. Theme days? Meme battles? Spotify playlist swaps? Give people room to bring their personality into work. It makes everything feel more human and less like an episode of Severance.

5. The “Leave It Better” Rule

Before every meeting, email, or interaction, ask: How can I leave this person better than I found them? A simple compliment? A piece of encouragement? A tiny boost? This mindset shift can change the whole vibe of your culture.

Bringing It Home: Are You In?

We’re not reinventing the wheel—we’re just remembering why it exists: to make the ride smoother for everyone. Radical empathy and micro-moments aren’t complicated, but they are intentional. And the best part? Anyone can start, right now.

So, who’s in? Who’s ready to trade in stale engagement tactics for real connection, trust, and those everyday moments that actually mean something? Let’s go build something people actually want to be part of.

About the Author, David Drees:

David Drees is a speaker and culture advisor who helps organizations move beyond surface-level engagement strategies to create real, human-centered workplaces. He’s worked with global brands like Starbucks, American Airlines, and VMWare, guiding leaders to foster cultures where people feel valued, connected, and empowered.

With a mix of insight, humor, and practical strategies, David makes workplace culture conversations engaging and actionable. He believes that small moments and authentic recognition have the power to change the world —because culture isn’t built in boardrooms; it’s built in everyday interactions.

Based in Chapel Hill, NC, David’s greatest joy is being a husband and a dad to Oliver, Milo, and Beckett. He’s also a proud Ohio State Buckeye—something he’ll happily remind you of, whether you ask or not!

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