Your Team Won’t Take Initiative? Start Here.

Ever feel like your supervisors are stuck in “wait and see” mode?

They wait for problems to escalate.
They wait for you to make the first move.
They wait… and wait… while opportunities sail on by like that one sock that’s just out of reach behind the dryer.

If you're the leader of a team of supervisors, and you’re wondering why no one is stepping up, here's the hard truth: initiative doesn't grow in silence. It grows when people feel seen, trusted, and supported in real time.

And that starts with one ridiculously simple leadership behavior:

Frequent, informal check-ins.

But First: Why Isn't Your Team Taking Initiative?

Let’s be clear. Your people want to do well. But initiative is a fragile thing. It needs reinforcement, clarity, and trust to grow. Without that?

You get supervisors who play it safe.
Or second-guess themselves.
Or ghost their own staff until the quarterly review.

And you? You’re stuck with a team that only moves when you push—and then you’re left wondering if you hired the wrong people or just forgot to water them.

You’re not alone. A lack of initiative is often a systems issue, not a people issue. It’s a product of unclear expectations, inconsistent feedback, and leadership that feels... distant.

The Fix? Start Checking In (But Not the Formal Kind)

You don’t need to roll out another performance management system or invent a new acronym. You just need to start having quick, low-pressure, human conversations that build connection and surface what’s really going on.

And even more importantly—your supervisors need to be doing the same with their teams.

If your leadership team isn’t regularly checking in with the people doing the work, they’re leading from a distance—and performance suffers at close range.

3 Informal Check-In Styles (Pick One, Please)

These aren’t weekly performance huddles. These are 2–5 minute touchpoints designed to say: “Hey, I see you. Your work matters. And I’ve got your back.”

1. Observe First

Spend five minutes shadowing (yes, creepily nearby but with good intentions). No need to interrupt or hover—just be present.

Afterward, say something simple:

• “I noticed how you handled that interaction—nice job staying calm.”

• “You’ve got a really efficient system going. Is that something we could teach others?”

Why it works: People do more of what gets noticed. You don’t need a parade—just acknowledgment. Bonus: you get a real-time pulse check without needing a report.

2. One-Question Walk-By

On your next lap around the office, drop in with a single question:

• “What’s going well today?”

• “What’s been frustrating you lately?”

• “What’s one thing that would make your day easier?”

Why it works: These questions aren’t earth-shattering, but they open doors. They say, “I care more about what’s going on with you than what’s going wrong with the printer again.”

For more inspiration, check out this Forbes piece on why informal conversations create stronger teams.

3. The Daily Text

Text. Sticky note. Chat rooms (if you’re still using AOL). Doesn’t matter. Reach out to 1–2 supervisors a day with:

• A quick thank you.

• A “what do you need today?”

• A “just checking in—how’s your team holding up?”

Why it works: You become a consistent, non-threatening presence. And when people get used to hearing from you, they’re more likely to speak up before things blow up.

Modeling Is Everything

If you want your supervisors to lead this way, you have to go first. Be the kind of leader who checks in without checking boxes.

Here’s what happens when you model it:

• They start doing it too.

• They feel more supported and less isolated.

• They learn what “good leadership” actually looks like.

Want to hold them accountable without adding to your workload? Try this:

• Ask supervisors to share one team insight per week during your check-ins with them.

• Use a shared doc or Slack thread to log “quick wins” and “what I’m hearing this week.”

What Happens When You Don’t Follow Up

Let’s be real: check-ins are a trust builder only if you do something with what you hear.

If someone shares a frustration and never hears back? That door closes fast.

You don’t have to fix everything—just circle back. Say, “I brought that issue up in leadership—still waiting on a response, but I wanted you to know it’s not forgotten.”

Trust builds in the follow-through, not just the question.

Start Small, but Start Now.

You don’t need a spreadsheet, a strategy session, or a team of consultants named Chad.
You need 15 minutes a day.
And a reminder that leadership isn’t about big gestures—it’s about small ones, done consistently.

👉 Want to give your supervisors a leg up?
Grab my free download:
[The 4 Supervisor Habits that Lower DSP Turnover Fast]
(It’s like giving them a playbook for better leadership… without adding to their to-do list.)

You’ve got this. And if today’s check-in is just, “Hey, I noticed you didn’t look completely overwhelmed—nice job,” ……that’s still a win!