You know what’s worse than not getting the job?
Getting the job and realizing two weeks in that it’s nothing like what you expected.
I’ve seen this happen to Filipino remote workers repeatedly.
They’re so excited to land the position that they forget to ask the questions that actually matter.
The ones that determine whether you’ll still be happy (and employed) six months from now.
Let me show you exactly what to ask.
Do Your Homework First
Before the interview, spend 30 minutes researching the company:
Check their website and LinkedIn presence
Look for reviews from current or former employees
Determine how long they’ve been operating
Find out if they already have remote workers (or if you’re their first experiment)
This research tells you which questions to prioritize.
Work Hours and Time Zone Expectations
“We’re flexible” is not an answer.
You need specifics.
Ask: “What are the core collaboration hours, and how much flexibility exists for the rest of my workday?”
This reveals whether they’ve actually thought through the time zone difference.
Good response: “We need you available from 9 AM to 12 PM Eastern for team meetings, but the rest of your work can be done asynchronously.”
Red flag response: “We’re a team, so we expect everyone online when we’re online.”
See the difference?
Ask: “How much of the work is synchronous versus asynchronous?”
If everything requires real-time collaboration and they’re 12 hours ahead, you’re signing up for night shift. That’s fine if you know it upfront—it’s not fine when you discover it after you’ve quit your other job.
Internet and Technical Infrastructure
Let’s be real: Internet in the Philippines can be unreliable. Power outages happen. Your connection drops during thunderstorms.
Companies hiring from the Philippines should know this and have a plan.
Ask: “What’s your policy if my internet goes down? Do you provide equipment and an internet allowance for backup connectivity?”
Good response: “Yes, we provide a monthly internet allowance and expect you to have a backup option like mobile hotspot. If there’s an extended outage, just let us know.”
Red flag response: Confusion or annoyance that you’re asking.
Also clarify:
Will they send you a laptop, or do they expect you to use your own?
If it’s your equipment, is there a tech allowance?
What happens if equipment breaks?
These aren’t unreasonable questions. They’re standard for remote work.
Payment Terms and Tax Compliance
Nobody likes talking about money in interviews, but you need to.
Ask: “What currency will I be paid in, what’s the payment method, and what’s the exact schedule?”
Why this matters:
USD vs. PHP makes a huge difference with exchange rates
PayPal, Wise, and bank transfers have different fees and processing times
Monthly payment when you’re used to bi-weekly can disrupt your budget
Ask: “How do you handle tax compliance for Filipino contractors? Will you provide documentation for BIR filing?”
Some companies provide certificates of income or tax documents. Others leave you to figure it out yourself.
If you’re hired as a contractor (which is common), you’re responsible for your own taxes—meaning quarterly payments to BIR. If nobody explained this, April will bring an unpleasant surprise.
Communication Culture and Expectations
“We use Slack” tells you nothing.
Ask: “What’s your communication culture? Are there expectations to respond outside of core hours?”
Some companies respect boundaries—you’re online during your shift, and that’s it.
Others expect constant Slack availability, with responses required at 10 PM because someone in another timezone had a question.
Both approaches are fine, as long as you know what you’re signing up for.
Ask: “How many meetings should I expect per week, and are they recorded for timezone differences?”
If they’re scheduling five meetings weekly at 3 AM your time without recording them, that’s a problem.
Good remote companies:
Record meetings so people in different timezones can watch later
Batch meetings into specific days to minimize interruptions
Contract Terms and Job Security
This is boring but critical.
Ask: “What’s the contract structure, probation period, and notice requirements for both parties?”
You need to know:
Is this a 3-month contract, 6-month, or ongoing?
Is there a probation period where they can let you go with minimal notice?
How much notice must you give to leave (and how much they must give you)?
I’ve seen Filipino workers terminated with zero notice after 28 days because the contract specified “30-day probation period with immediate termination rights.”
They never asked about it in the interview.
Don’t be that person.
Career Growth and Development
If you want to build skills and advance your career, these questions matter.
Ask: “What does career progression look like for remote team members? Are there opportunities for skill development?”
Some companies have clear paths: specialist → senior specialist → team lead.
Others are flat—you’re hired to do a task, and that’s what you’ll do indefinitely.
Neither is wrong, but you should know which you’re joining.
Also ask:
Will they pay for courses or certifications?
Is there a learning and development budget?
The best remote companies invest in their people. The worst see you as a replaceable task-doer.
Team Composition and Onboarding
Remote work can be isolating, especially if you’re the only Filipino on a team of people who’ve worked together for years.
Ask: “Can you describe the team I’ll be working with? How do you build team cohesion for remote workers?”
Listen for:
Team size and composition
Mostly remote or mostly in-office?
Are there other Filipino workers?
Ask: “What does the onboarding process look like for remote workers?”
Good companies: Structured plan with clear week-by-week progression and an assigned buddy.
Red flag companies: “We’ll send you login info and you’ll figure it out.”
Performance Measurement and Monitoring
This reveals whether they’re reasonable or will micromanage you into insanity.
Ask: “How do you measure success in this role? What monitoring tools, if any, will be used?”
If they use time-tracking software that takes screenshots every 10 minutes, you can decide if that’s acceptable to you.
Better companies measure output, not activity. They care that you finished the project, not that you moved your mouse at 2:47 PM.
Ask: “What does success look like in the first 30, 60, and 90 days?”
This reveals whether their expectations are realistic or if they’re expecting miracles.
Benefits and Holiday Policies
“Competitive benefits” means nothing. Get specific.
Ask: “What benefits are included, and how are Philippine holidays handled?”
Consider:
Does health insurance work in the Philippines?
Do they respect Philippine holidays, or expect you to work them?
How many PTO days? Do you accrue them monthly or get them upfront?
What’s the sick leave policy? Do you need a doctor’s note?
If a company acts like you’re asking for too much by wanting to know about basic benefits, that tells you how they value their people.
Actual Job Responsibilities
Job descriptions lie—not always intentionally, but they do.
The posting says “content writer” but they actually want someone who writes content, manages social media, designs graphics, and handles email marketing. For the same pay.
Ask: “Can you walk me through a typical day or week? What are the non-negotiable responsibilities versus nice-to-haves?”
This reveals if the job matches the posting.
Ask: “What’s NOT part of this role?”
This question catches people off guard, but it’s brilliant. It forces them to define boundaries.
If they can’t answer, there are no boundaries—you’ll be doing whatever random task someone thinks of.
Red Flags You Can’t Ignore
Watch for these warning signs:
Vague about work hours – “We’re flexible” without specifics usually means “available whenever we need you”
Won’t discuss payment clearly – Legitimate companies have no problem explaining how and when you’ll be paid
Pressure to decide immediately – “We need an answer today” is a manipulation tactic
Casual mention of invasive monitoring – Suggests a culture that doesn’t trust employees
Disorganized interviewer – Usually reflects how the entire company operates
Trust your gut.
How to Ask Without Sounding Demanding
Professional companies expect candidates to ask questions. It shows you’re serious and thoughtful.
Frame questions positively:
Instead of: “I’m concerned about…”
Say: “I want to set myself up for success, so I’d like to understand…”
Time your questions strategically:
Early: Role clarity, work hours, team structure
Mid-interview: Communication culture, growth opportunities
End: Logistics like payment, contracts, start date
If you don’t get to all your questions, send a follow-up email:
“Thank you for your time today. I have a few additional questions to help me make an informed decision…”
Your Interview Checklist
Before your next interview, write down your top 10 questions.
Pick the ones that matter most for your situation:
Reliable internet? Maybe that’s less critical for you
Supporting a family? Payment terms and job security move to the top
Everyone’s priorities differ, but everyone should ask something from each category:
Work hours and time zones
Compensation and payment
Communication expectations
Career growth
Performance measurement
The companies worth working for will appreciate your questions.
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