Remote Job Red Flags

I applied to 50 remote jobs in three months. About 15 of them had serious red flags. Here's what I learned to watch out for.

Red Flag #1: "Must Be Available 24/7"

One job posting said "flexible hours" but the interview revealed they expected me to be online from 6 AM to 10 PM across multiple time zones.

That's not remote work. That's never sleeping.

What to look for: Ask about core hours, meeting schedules, and response time expectations during the interview.

Red Flag #2: No Clear Communication Tools

I asked one company what tools they use for communication. The hiring manager said "we'll figure it out."

If a company doesn't have established remote communication practices, you'll be the one dealing with the chaos.

What to look for: Ask about their tech stack—Slack, Teams, Zoom, project management tools. Established remote companies have this figured out.

Red Flag #3: "We're Trying Remote for the First Time"

Nothing wrong with companies adapting. But being their guinea pig for remote work means you'll face:

• Unclear expectations
• Constant policy changes
• Managers who don't trust remote workers
• Pressure to "prove" remote work works

What to look for: Ask how long they've been remote and what percentage of the team works remotely. If you're the first, proceed with caution.

Red Flag #4: Excessive Monitoring

One company wanted to install tracking software that took screenshots every 10 minutes and monitored my keystrokes.

Hard pass.

What to look for: Ask about productivity tracking and monitoring tools. If they can't trust you to work without surveillance, the culture is broken.

Red Flag #5: Vague Job Description

"Looking for a self-starter who can wear many hats" usually means "we don't know what we need, but we need someone to do everything."

Remote work requires clear expectations. Vague job descriptions lead to scope creep and burnout.

What to look for: Specific responsibilities, clear deliverables, defined success metrics. If they can't articulate what you'll be doing, run.

Red Flag #6: No Video Interviews

If a company won't do video interviews, something's off. Either:

• They're not who they say they are (scam)
• They don't have proper remote infrastructure
• They're hiding something about the team or culture

What to look for: Insist on at least one video interview. Meet your potential manager and teammates. See their faces. Read the room.

Red Flag #7: Upfront Payment Requests

This should be obvious, but I still saw it: companies asking for money upfront for "equipment" or "training materials."

Legitimate companies provide equipment or reimburse you. They don't ask you to pay them.

What to look for: Any request for money before you start working is a scam. Period.

The Green Flags

Not all remote jobs are bad. Here's what good ones look like:

• Clear communication about hours and expectations
• Established remote work policies and tools
• Video interviews with multiple team members
• Specific job descriptions with measurable outcomes
• Trust-based culture, not surveillance
• Transparent about challenges and how they solve them

What I Accepted

I ended up accepting a remote role that:

• Had been fully remote for 3 years
• Used Slack, Notion, and Zoom
• Had core hours (10 AM - 2 PM my time) but flexible otherwise
• Trusted me to manage my own schedule
• Provided clear quarterly goals
• Introduced me to 5 different team members during interviews

It's been great. But I almost took one of the red flag jobs out of desperation.

Your Move

Remote work can be amazing. But bad remote jobs are worse than bad office jobs because you're isolated and unsupported.

Trust your gut. Ask hard questions. Don't settle for red flags just because you want to work from home.

The right remote job is out there. Don't waste time on the wrong one.