You’ve just delegated a major task. At first, you feel relieved. But an hour later, your mind starts racing. Did they understand the instructions? What if they miss something? What if the client complains?
So you check in. Then you check again. And again. Soon, you’re not really letting go—you’re standing over their shoulder, shadowing their every move.
This isn’t oversight. It’s hovering. And hovering kills both confidence and initiative.
Yet the opposite extreme is just as dangerous: disappearing completely. If you never check in, you risk discovering problems only when they’ve grown too big to fix.
Delegation thrives in the middle ground: not suffocating supervision, not total absence, but a rhythm of check-ins that keeps everyone aligned.
As The Delegation Game explains:
“Check-ins are the headlights on a dark road. Without them, you’re driving blind. With too many, you’re blinding the driver.”
The Desire to Stay on Track
Both managers and team members share the same hidden desire: nobody wants to get lost.
Managers want assurance that the work is moving in the right direction. Team members want the confidence that they’re not drifting off course.
Check-ins, done well, satisfy both. They keep the journey visible without stopping the car every few minutes.
When Silence Becomes the Problem
Take Luis, for example. His manager delegated the company’s year-end report and then went silent for weeks.
Luis assumed things were fine. But when he finally presented the draft, it was nothing like what the manager expected. Wrong focus, wrong data, wrong tone.
Both were frustrated. Luis had wasted hours of effort. The manager had to scramble to fix it.
The issue wasn’t incompetence. It was the absence of checkpoints—the “mile markers” that could have flagged misdirection early.
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The Other Extreme: Smothering with Updates
Then there’s Anna’s story. She was assigned a product launch campaign. Excited, she jumped in. But every morning her manager sent messages like: “Where are you on this? Did you talk to the vendor? What about the tagline? Show me what you’ve done.”
Anna spent more time reporting progress than making progress. She felt distrusted and drained. Eventually, she stopped trying new ideas because she knew they’d be second-guessed anyway.
This is the danger of micromanagement: when oversight turns into overreach, creativity and ownership vanish.
How to Agree on Check-Ins That Work
The solution isn’t to eliminate check-ins but to agree on them upfront. Think of them as the pit stops in a race: short, purposeful, and planned—not random interruptions.
Here’s what to clarify when setting them up:
Frequency
Decide how often you’ll check in. Will it be daily stand-ups, a weekly sync, or milestone-based reviews?
- Daily works for new hires or high-risk tasks.
- Weekly fits steady projects with clear direction.
- Milestone-based suits experienced staff handling long-term outcomes.
Format
Pick a format that fits the work.
- Quick huddles for fast-moving tasks.
- Email summaries for ongoing updates.
- Dashboards or traffic-light reports (green/amber/red) for visibility without chatter.
Indicators
Agree on how progress will be signaled. A simple green (on track), amber (at risk), red (stuck) system is often enough. The point is to spot issues early without lengthy reports.
Let the Delegate Lead the Process
Check-ins should be owned by the delegate, not the manager.
When the manager is always the one chasing updates, it feels like policing. But when the team member runs the check-in—reporting progress, raising risks, asking questions—it becomes accountability.
In The Delegation Game I wrote:
“When the delegate manages the updates, they manage the task. When the manager manages the updates, the task never really leaves their hands.”
That’s the difference between oversight and hovering.
A Story of Balance
Consider Jun. He was asked to lead the rollout of a new HR system. Before starting, his manager sat down with him:
“We’ll do a 15-minute check-in every Monday. You’ll update me on three things: what’s complete, what’s in progress, and where you’re stuck. If anything urgent pops up, flag it midweek. Otherwise, you own this.”
The rhythm was clear. The rules were simple. Jun felt trusted, but not abandoned. Problems surfaced early enough to be solved, yet he still had space to lead the project his way.
The project went live smoothly. Jun gained confidence, and his manager gained peace of mind.
The Cost of Getting It Wrong
Skipping check-ins leads to surprise disasters. Overdoing them leads to smothered teams. Both waste time, erode trust, and turn delegation into frustration.
But when check-ins are designed as alignment tools, they:
- Prevent small issues from becoming big ones.
- Signal trust while keeping visibility.
- Free the manager’s time and empower the team.
The stakes are clear: get check-ins wrong, and delegation fails. Get them right, and delegation scales.
The Shift That Keeps Work Flowing
Here’s the shift: Check-ins aren’t for control. They’re for alignment.
The best check-ins are brief, predictable, and led by the delegate. They exist to keep work moving, not to slow it down.
Your Move This Week
Think of one project you’ve recently delegated. Ask yourself:
- Did I agree on when and how we’ll check in?
- Does my team member know what signals to use when something is off track?
- Am I chasing updates, or are they leading the updates?
If the answer worries you, reset the rhythm. Call your delegate and say: “Let’s agree on a simple check-in schedule so you lead the updates. That way we’re aligned without me hovering.”
One small agreement can save weeks of stress.
What’s Coming Next
This is Step 5 of the Delegation Play. By now, you’ve defined results, set boundaries, and equipped your people with authority and resources. With check-ins in place, you have a rhythm that keeps everyone moving together.
Next, we’ll explore why documenting and debriefing matter—the part most leaders skip, but the step where real growth happens (Step 6 & 7).
Delegation doesn’t mean disappearing. It means staying connected just enough to keep the road clear, while letting your people drive the car.
