When Someone on Your Team Is Holding Two Jobs: A Manager's Playbook

You have been noticing something. Response times have drifted. Availability during certain hours has become unpredictable. Output has gone in waves -- strong one week, stalled the next. Your gut says something has changed, but you are not sure what.

If you manage a remote team, one possibility worth considering is that the person is managing two jobs simultaneously. A 2024 Resume Builder survey found that 79% of remote workers either hold or are open to holding a second full-time job -- a figure that reflects how dramatically remote work changed the practical feasibility of dual employment after 2020.

This is a guide for what to do once that concern is on the table. Not surveillance, not an immediate confrontation -- a structured, documented, human process that protects the company and treats the employee fairly.

Step 1: Build a Behavioral Evidence File Before Doing Anything

The instinct to act quickly is understandable. Resist it. Acting on a suspicion without documented evidence creates legal exposure, and it risks damaging your relationship with an employee who may have a completely different explanation for what you are seeing.

Spend 3-4 weeks logging specific, objective observations:

• Slack or Teams response times during core hours, with dates and approximate durations
• Specific missed deadlines or incomplete deliverables, with dates
• Calendar patterns: declined meetings, recurring holds that cannot be explained by any team project
• Meeting participation: late arrivals, early exits, distracted engagement
• Output velocity: tickets closed, PRs merged, tasks completed per week, compared to their established pattern

This documentation serves two purposes. First, it helps you determine whether the pattern is real and sustained, or whether you are noticing coincidental variation. Second, if the situation does escalate to HR or legal, you have objective records rather than impressions.

Step 2: Verify Your Moonlighting Policy Exists and Was Communicated

Before you can hold an employee accountable for violating a policy, that policy must have been clearly communicated. Employees cannot be held to a standard they were never clearly shown -- a basic principle of employment law that also applies to company policy.

Check your employment contracts and employee handbook:

• Is there an exclusivity clause that prohibits concurrent full-time employment?
• Is there a conflict-of-interest policy that requires disclosure of secondary employment?
• Was the employee acknowledged receipt of these policies in writing?

If your organization does not have a clear moonlighting policy, this is the moment to involve HR and get one in place -- regardless of how the current situation resolves. Future situations will be much cleaner to handle with a policy framework established in advance.

Step 3: Have the Check-In Conversation

This is the most important step, and the one most managers get wrong by framing it as an accusation rather than a genuine inquiry. You do not yet know what is causing the pattern. Your job in this conversation is to surface the explanation, not deliver a verdict.

The framing that works:

"I wanted to check in because I have noticed some changes in your patterns over the past several weeks -- your response times have slowed, and your availability during the afternoon has been harder to predict. I want to make sure you are okay and understand if something is going on that I should know about."

This approach does several things. It communicates that you have noticed, without being accusatory. It opens space for the employee to explain. And it demonstrates care, which is appropriate regardless of what the explanation turns out to be.

Possible outcomes of this conversation:

• Personal situation: The employee is dealing with a family matter, health issue, or personal crisis. The right response is support, accommodation where possible, and a clear agreement on how work gets managed during the difficult period.
• Burnout or disengagement: The employee is checked out -- not necessarily because of a second job, but because they are not finding the work meaningful or feel undervalued. This is a retention conversation.
• Disclosure of dual employment: The employee acknowledges holding a second job. Now you move to the policy framework.
• Denial without resolution: The behavioral pattern continues without explanation. This is when you involve HR.

Step 4: If Dual Employment Is Confirmed -- Policy Response

If the employee confirms they are holding a second job, the response depends on your policy and the specifics of the situation. SHRM recommends being solution-minded rather than immediately punitive -- working together to find a solution rather than defaulting to termination.

The framework:

1. Determine whether the second job creates a conflict of interest. If the employee is working for a competitor, the answer to that question may drive everything else.
2. If no conflict of interest: assess whether performance has actually been impacted. If not meaningfully, some organizations choose to allow disclosed dual employment with conditions -- no conflicts, no performance impact, formal disclosure on file.
3. If performance has been impacted: issue a formal performance improvement plan with specific, measurable expectations and a timeline. Document everything.
4. If the second job violates an exclusivity clause or conflict-of-interest policy: involve HR and legal before taking any action. At-will employment doctrine generally supports termination, but the process matters.

Step 5: Address the Root Cause

Whether or not the immediate situation resolves through conversation or policy action, understanding what drove the situation helps prevent recurrence.

Financial pressure is the most common driver of dual employment. Compensation that has not kept pace with market rates leaves employees feeling they have no option but to supplement their income elsewhere. Regular compensation benchmarking -- not just at hiring but annually -- reduces this pressure before it drives behavior.

Career stagnation is the second driver. An employee who feels stuck, underutilized, or without a visible path forward may take on a second role that offers the growth or variety their primary job does not. Meaningful one-on-ones that include genuine career development conversations can surface this before it becomes a problem.

Related reading: 5 warning signs your best employee is about to quit and detecting dual employment without surveillance software.