Let’s be honest about what usually happens.
You post a job. Someone applies with a great resume. The interview goes well enough. You send them a login and say “here’s what we need done.”
Then everything slowly unravels.
The work comes in late. Communication is spotty. You’re not sure what they’re doing half the time. And eventually, you realize this isn’t working.
Sound familiar?
That scenario doesn’t mean Latin American remote workers can’t do the job.
It usually means your onboarding was chaotic, your expectations were unclear, and your support system was nonexistent.
The hire gets blamed. But the process was broken from day one.
Immediate Steps: What to Do This Week
Alright, it didn’t work out. Here’s exactly what to do right now.
Step 1: Schedule the termination conversation within 24 hours
Get on Zoom or Teams. Set up a 15-minute meeting.
Not email. Not Slack. A real video call.
Step 2: Prepare your termination script
Write down exactly what you’ll say:
“We’ve decided to end our working relationship. Your last day is [date]. We’ll pay you for all work completed through [date]. Here’s what happens next with equipment and access.”
Keep it under 3 minutes. Be direct. Don’t negotiate.
Step 3: Terminate all access immediately after the call
Within 5 minutes of ending the conversation:
- Disable email access
- Remove from Slack, Teams, or Discord
- Revoke GitHub, project management tools, and CRM access
- Change passwords for any shared accounts they knew
- Remove from payment systems like Wise or PayPal
Don’t wait until tomorrow. Do it while you’re still at your computer.
Step 4: Secure your client relationships and data
Within the next hour:
- Email clients they were working with directly, introduce their replacement or point of contact
- Download any files they created from cloud storage
- Document passwords, project status, and in-flight tasks they were handling
- If they have company equipment, send return instructions with a prepaid label immediately
Step 5: Process final payment within 5 business days
Calculate exactly what you owe:
- Hours worked through termination date
- Any unused paid time off (if they were an employee)
- Reimbursable expenses submitted before termination
Pay it fast. Don’t make them chase you.
Step 6: Check your legal exposure
Answer these questions honestly:
- Did they work set hours that you controlled?
- Did they only work for you, no other clients?
- Did you provide all their tools and equipment?
- Did they take direction from your managers daily?
If you answered yes to three or more, you might have misclassified an employee as a contractor.
In Brazil and Mexico especially, this matters. A lot.
The Cultural Blind Spots That Kill Remote Hires
Here’s a question worth asking: was it really a performance issue, or did you ignore their calendar and culture?
Create a shared holiday calendar right now
Go to TimeAndDate.com. Look up national holidays for their specific country.
Add these to your Google Calendar or project management system:
- Carnival (Brazil): February, usually 4-5 days
- Semana Santa (Holy Week): March/April, entire week off in many places
- Fiestas Patrias (Chile): September 18-19, often extends to full week
- Día de los Muertos (Mexico): November 1-2
- Independence days: varies by country, often multi-day celebrations
Mark these as “no deadlines” weeks in your planning.
Set explicit working hour expectations
In your next hire, include this in the contract:
“Core overlap hours: [specific times in their timezone]. Example: 10am-2pm Colombia time, Monday-Friday.”
Don’t say “US business hours” or “normal working hours.” Those mean nothing to someone in Argentina.
Understand lunch and family time
In many Latin American countries, lunch is 1-2 hours and non-negotiable.
A parent leaving at 3pm to pick up kids from school is normal, then logging back in at 8pm.
If you need specific hours, write them down. If you don’t care as long as work gets done, say that explicitly.
Learn how they communicate feedback
Many Latin American professionals won’t say “no” directly in a meeting with multiple people.
They’ll say “I’ll see what I can do” or “that might be difficult.”
That’s not agreement. That’s polite pushback.
Create a private channel for just you and them. Make it clear that saying “I can’t do this” or “this deadline is impossible” is expected and safe.
How to Hire Better the Second Time
The difference between a failed hire and a great hire is usually your process, not the talent pool.
Write a detailed job description with specific deliverables
Don’t write: “Looking for a social media manager.”
Write: “Looking for someone to create 20 Instagram posts per month, respond to comments within 2 hours during 10am-6pm EST, and grow our following by 10% in 90 days.”
Include:
- Exact software they’ll use (Canva, Buffer, specific tools)
- Success metrics for 30, 60, 90 days
- Communication expectations (daily updates in Slack, weekly video check-in)
- Required overlap hours in their timezone
Create a paid test project
Pay them $100-300 to complete a real task before hiring full-time.
Examples:
- Writer: 1,000-word article on a topic you need
- Developer: Fix a real bug or build a small feature
- Designer: Create 3 versions of a graphic you actually need
- Customer support: Respond to 10 real customer emails
Evaluate:
- Quality of work
- How they communicate questions
- Whether they meet the deadline
- How they handle feedback
This eliminates 80% of bad hires.
During interviews, ask these specific questions
“Walk me through your typical workday. What time do you start, when do you take breaks, when do you finish?”
“What’s your internet speed right now? What happens if your power goes out?”
“Show me your workspace. Do you have a quiet area for video calls?”
“How do you prefer to receive feedback? In writing or on a call?”
“What’s the last project where you missed a deadline? What happened?”
These questions reveal infrastructure issues, communication style, and how they handle problems.
Check 2-3 references and ask specific questions
Don’t ask: “Was this person good?”
Ask:
- “On a scale of 1-10, how would you rate their communication? Can you give me an example?”
- “Did they ever miss a deadline? What did they do when that happened?”
- “How much oversight did they need?”
- “Would you hire them again? Why or why not?”
If they hesitate on “would you hire them again,” that tells you everything.
Build an Onboarding System That Actually Works
Here’s a 30-day onboarding plan you can copy.
Week 1: Orientation (no output pressure)
Day 1:
- 1-hour video welcome call
- Send access to all tools (email, project management, communication)
- Assign a “buddy” on your team for questions
- Share company handbook or key documents
Day 2-3:
- Have them shadow team meetings
- Watch recorded training videos if you have them
- Read through past projects similar to what they’ll do
Day 4-5:
- Assign first tiny task (something that takes 2 hours max)
- Review it together on a call
- Give detailed feedback
Week 2: First real deliverable (with heavy support)
- Assign one complete project that’s representative of their role
- Schedule 2-3 check-ins during the week
- Provide feedback within 24 hours of submission
- Iterate together until it meets your standard
Week 3: Normal work (with normal support)
- Full workload begins
- Daily async check-ins (they post what they’re working on each morning)
- One 30-minute video call for questions
- You’re available but not hovering
Week 4: Independence (with scheduled feedback)
- They’re working independently
- End of week: 1-hour feedback session covering what’s working and what needs adjustment
- Set clear goals for month 2
Create these specific documents before their first day
- Communication norms doc:
“Daily updates: Post in #team-updates Slack channel by 10am your time with what you’re working on that day.
Urgent issues: DM me directly, I respond within 2 hours during 9am-6pm Colombia time.
Weekly sync: Every Tuesday 11am Colombia time, 30 minutes.
Deadline problems: Tell me the moment you realize you’ll be late, not after the deadline passes.”
- Tool access checklist:
List every single tool they need, with login instructions. Check them off as you grant access.
- First 30 days deliverables:
Write exactly what they should accomplish each week, with specific examples.
- FAQ document:
Anticipate 20 questions they’ll have and answer them in advance.
The Real Lesson
Your first remote hire failing doesn’t mean remote work doesn’t work.
It means you tried to hire remotely the same way you hire locally, without adjusting anything for distance, culture, time zones, or legal differences.
The companies that succeed with Latin American remote workers are the ones who:
Define roles with specific, measurable deliverables before posting.
Screen with paid test projects that reveal real ability.
Build 30-day onboarding plans with documented processes and weekly check-ins.
Set communication norms in writing, with exact hours and tools specified.
Respect cultural calendars and create shared holiday schedules upfront.
Get legal structures right from day one, either through an EOR or genuine contractor autonomy.
The talent is there. The opportunity is there.
You just need a system that actually works.
Fix those specific things, and your second remote hire will probably go much better than your first.
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