A No-BS Guide to Spotting Overemployed Workers

I've been writing a lot about overemployment lately as I think it's a trend that is growing in the post-COVID remote-friendly world. You’ll see tales of it on Reddit, Substacks, even Medium confessionals. And guess what? These aren’t just scammers or slackers. Most are brilliant operators gaming what is truly a broken tech industry culture. But, it still screws your team, your momentum, and your trust. You need to know what to look for - without cracking the whip on your whole team.

Red Flags: Spot the Behavior, Not Just the Person

Here’s what actually shows up on the ground when someone is secretly working two jobs:

1. Split Focus Disguised as Burnout

They miss key context in conversations. Ask for help and they “didn’t hear about that” despite sitting in the meeting. Burnout? Maybe. But it’s worth digging.

2. Predictable Availability Blind Spots

They’re somehow never around for 10am standups, and always “offline” between 1-3pm. OOO get booked pretty often.

3. Surprisingly Surface-Level Work

Output looks... fine. But never proactive. They ship basic pull requests but fade when it’s time for input architecture decisions or roadmap debates. They’re playing defense.

4. Always “Working,” Never Collaborating

They ping status updates frequently, but barely ask questions or join brainstorming. You’ll see them drop notes at odd hours, showing they’re “asynchronous” - but what they’re really doing is buying time.

5. Request for Company issued phone or equipment beyond a laptop.

This is a big one. One of the overemployed's secret to managing multiple jobs at once is to have separate equipment - from computer, monitor to headphones, cameras, and a phone. That way, you reduce the risk of mixing up your contexts. If an employee who doesn't normally need a mobile phone to do their job suddenly requests one, be on alert.

Combine two or three of those red flags, and you’ve got a pattern. Too many leaders rationalize it away as “just remote weirdness.” Don’t. You’re in denial.

How to Confirm It Without Creeping Everyone Out

Good managers don’t spy. But they also don’t let performance rot trickle into the team. Here’s how to get clarity without becoming Big Brother.

Start with Work Output & Expectations

What’s their actual delivery rate compared to historical data? Are there misalignments in availability vs. meeting norms or async work? Don’t get tempted to play detective. Let accountability gaps reveal the problem.

Use shared task tracking, documented expectations, and calendars. When someone’s consistently out of sync, back it with data, not vibes.

Related insight from real-world product teams struggling to maintain trust and performance: Lessons from real performance management conversations that got tricky

Use “One-on-Ones” for Signal, Not Just Support

Skip the small talk. Get into priorities they’re driving, blockers they’ve hit, and things they’re passionate about building. If they’re dodging accountability or seem disengaged long-term, that’s your signal.

Don’t ask “Are you working two jobs?” Too easy to deny. Instead ask:

• “What’s your calendar baseline like these days?”
• “Can you walk me through how you’re dividing between launch work vs learning?”
• “You seem stretched. Anything you’d want to delegate or shift?”

You’re giving them space to come clean - which some will, if they’re cracked from juggling too much.

Check Collaboration Consistency

Candidly ask peers about this person’s team behavior. Are they helpful? Do they go silent mid-week? Are they skipping key seat-at-the-table moments? Peer patterns expose overemployment faster than metrics ever will.

Consider the Tech (Lightly)

Tempted to add keystroke loggers? Don’t. That's a nuclear option. But if you already run Slack or GitHub activity metrics as part of your norm, look for patterns. Are they going dark during sprints? Are commits done at odd hours, always solo? Data doesn’t lie. But it needs context, or you’ll falsely accuse someone solving childcare problems or managing chronic illness.

What to Do Once You Know (And What Not to Do)

Let’s say you’ve reviewed data, had a few concerned 1:1s, and the picture’s clear: they’re overemployed.

You’ve got two choices, and depending on how you handle it, your team will trust you more - or start looking for their own “Job B.”

Option 1: Terminate for Breach of Trust

If they’re truly doing two full-time jobs, that usually violates an employment agreement. But before you push the red button, dig:

• Do they have a second employer listed on LinkedIn?
• Have they admitted to juggling two roles in any way?
• Do you have explicit language in your contract about moonlighting?

If it's rock solid, have the conversation, document it, and exit calmly. Avoid drama. Don’t call them a fraud in public. Leads talk. Damage travels.

Option 2: Reset Expectations, Not Out of Mercy But Leverage

This option is a rare: if they’re high-output, and you caught them early, you might actually recover them. Some people took a second job because managers dropped the ball on structure, feedback, or purpose.

Try this first:

• Lay out unambiguous performance and availability expectations
• Reorient on mission, learning path, and reward
• Let them know transparency matters more than punishment

Then pause. If they come clean and re-commit, stay. If not, time to separate.

This approach only works if your entire leadership team aligns. One weak manager tolerating overemployment destabilizes team trust organization-wide.

Build the Kind of Culture Where This Doesn’t Happen (Much)

Let’s be real: you’re never going to prevent every case. But you can make your workplace not worth the risk.

Be Brutally Clear During the Interviews 

Most overemployed workers exploit vagueness. Don’t give them wiggle room. Everyone on your team should know:

• The measurable definition of success for their role
• What “good” time responsiveness looks like on your team
• What collaboration norms - Slack, meetings, async docs - you expect

Avoid the “we’re chill, just be awesome” trap.

Normalize Visibility Without Surveillance

Use shared roadmaps, progress snapshots, or async standups on video or Slack. Make it easy to see who’s stuck or missing - without shadowing them.

More companies are learning to balance transparency and autonomy this way. Read how others are doing it here

Promote Intrinsic Motivation

People double dip when they stop feeling connected to what they build. Fix that. Remind people what the mission is. Celebrate wins. Invest in boredom-proof sprints.

And please - for the love of all that’s productive - don’t run performance by how fast someone replies to Slack.

Spotting Overemployment Patterns vs. One-Off Burnout Behaviors

Final Thoughts: Find the Truth Without Losing the Team

Here’s the paradox: if you over-police your team, you’ll kill motivation and drive people underground. But if you avoid uncomfortable truths, overemployment will rot your culture from the inside out.

Spot the signs. Have real conversations. Hold the line. But more than that, build a place where people would rather show up with full focus than quietly game the system.

And if your gut’s been buzzing about someone on your team for weeks, trust it. Start tracking work, not just face time.

The best workplaces mix trust with standards - and don’t let either slip.

Ready to have that first conversation? Good. Clock’s ticking.