checking the box

Beyond Checking the Box: Show Your Team What Success Looks Like

by | Jun 28, 2025 | Asking For a Friend Featured

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Paint a Clear Picture of What Success Really Means

So, you’ve done the work. You’ve identified the habits that matter most—the practical, tactical behaviors that, when done well, drive the results your team is here to achieve. You’ve communicated them. Maybe even created a job aid or a snappy acronym. And now? Some of your team members are just checking the box.

They’re technically “doing the thing”… but not really doing the thing.

You know what I mean. They’re checking the box. Going through the motions. Phoning it in. And not even with great reception.

They say, “Yeah, I’m doing it,” but you can practically hear the unspoken:
“…and see? It doesn’t work.”

Let’s talk about that.

checking the box

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Step 1: Double Down on Clarity

Yes, again. Yes, even if you swear you were already clear.

This time, go beyond simply defining the habit. Instead:

  • Connect the dots to the bigger picture. Show how this habit impacts actual business outcomes. That might mean doing a little digging—who’s doing the habit well, and what results are they seeing? If their customer satisfaction scores, sales numbers, or productivity metrics are higher, use that. Draw the line. Make it real.

  • Break down what “good” looks like. Get specific. Don’t assume everyone shares your mental image of excellence. Illustrate it. Tell a story. Use examples. Better yet, use real success stories from your team.

  • And yes, use your 5×5. That means communicate the expectation five times, five different ways. Email, team meeting, Slack, one-on-one, interpretive dance… okay, maybe not that last one. But the point is: repetition and variety matter.

  • Include a check for understanding. “Does that make sense?” won’t cut it. Ask them to explain it back to you. Even better—have them show you what great looks like.

Step 2: Show Up Curious

Now that you’ve reinforced what “good” really means, it’s time to dig into what’s getting in the way.

And no, not with an eye-roll or a sigh. With curiosity.

Ask:

  • What’s hard?

  • What’s getting in the way?

  • What’s slowing you down?

  • What would make this easier?

  • Is this a skills issue, a tools issue, or something else entirely?

Because checking the box isn’t usually about laziness—it’s often about uncertainty, disconnection, or quiet frustration.

Maybe they tried once and felt it didn’t work. Or were they’re afraid to ask for help. Maybe they think no one’s noticing either way.

Your curiosity can surface all of that. And once it’s out in the open? You can do something about it.

See Also: How to Support a Struggling Sales Person

Step 3: Stay Connected

This part matters just as much as the first two.

Once you’ve clarified and explored the obstacles, keep the connection going. Ask:

  • “What do you need next?”

  • “What support would make the biggest difference right now?”

  • “What would success feel like—for you?”

And listen. Really listen.

That ongoing loop of feedback and support helps people re-engage. It signals, “I see you. I want you to succeed. And we’re in this together.”

What Would You Add? How do you help your team move from “checking the box” to spending their time on what matters most?

When your team is phoning it in, it’s tempting to dial up the pressure. But real results don’t come from more rules or heavier oversight. They come from going back to the basics—with more intention:

Clarity. Curiosity. Connection.

These are your leadership power tools. And when you use them well? You don’t just get compliance. You get commitment.

And that’s when the magic happens—when the habits you know will work actually start working, because they’re being done with heart, purpose, and skill.

So… what would you add?
What’s worked for you when your team’s technically on board, but not really all in?

Want more human-centered leaders in the workplace? Share this today!

  Want more human-centered leaders in the workplace? Share this today!

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Karin Hurt

Karin Hurt helps human-centered leaders find clarity in uncertainty, drive innovation, and achieve breakthrough results.  She’s the founder and CEO of Let’s Grow Leaders, an international leadership development and training firm known for practical tools and leadership development programs that stick. She’s the award-winning author of four books including Courageous Cultures: How to Build Teams of Micro-Innovators, Problem Solvers, and Customer Advocates and Powerful Phrases for Dealing with Workplace Conflict, and a hosts the popular Asking For a Friend Vlog on LinkedIn. A former Verizon Wireless executive, Karin was named to Inc. Magazine’s list of great leadership speakers. Karin and her husband and business partner, David Dye, are committed to their philanthropic initiative, Winning Wells – building clean water wells for the people of Cambodia.

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