Hire a Virtual Assistant in 60 Minutes

I've spent the last ten years building Wishup and personally overseeing the hiring of over 1,500 virtual assistants. In that time, I've watched founders make the same hiring mistakes repeatedly—and I've made plenty myself.

Here's what I've learned: hiring the right VA is never about finding someone cheap or nearby. It's more about having someone who actually frees up your time instead of creating more work.

This guide covers everything I wish I'd known before hiring my first assistant back in 2015.

Why Most Founders Fail at Hiring VAs (And How to Avoid It)

An average entrepreneur I speak with has tried hiring a VA at least once before. Most tell me the same story: "They seemed great in the interview, but they couldn't handle basic tasks without constant supervision."

The problem usually isn't the VA—it's the hiring process.

After reviewing hundreds of failed VA relationships, I've identified three patterns:

• Unclear expectations: You hire someone for "admin work" without defining what that actually means
• Wrong skill match: You need someone who knows HubSpot, but you hired based on personality alone
• No testing period: You commit to 40 hours/week before seeing how they work

Let's fix that.

Step 1: Know Exactly What You're Delegating (And What You're Not)

Before you write a job post or browse profiles, spend 30 minutes with this exercise.

Open a doc and list every task you did last week that meets these criteria:

• Takes under 30 minutes
• You've done it more than 3 times
• Doesn't require your attention
• Would free up mental space if someone else handled it

Common examples from founders I work with:

• Inbox management (filtering, flagging, drafting responses)
• Calendar scheduling and timezone coordination
• CRM data entry and follow-up reminders
• Research (competitors, markets, vendors)
• Social media scheduling
• Expense tracking and receipt organization
• Meeting prep and note-taking
• Customer support (first-line responses)

Step 2: Budget Realistically (Here's What VAs Actually Cost)

Pricing has changed dramatically since 2020. Here's what I'm seeing in 2025:

US-based VAs: $30-$75/hour

• Best for: Teams who need same-timezone communication and cultural familiarity
• Drawback: Higher cost limits how much you can delegate on a tight budget

Offshore VAs (Philippines, Latin America, India): $8-$25/hour

• Best for: Maximizing hours within budget
• Drawback: You handle all vetting, training, and management yourself

Managed VA services: $1,200-$3,000/month (typically 40-160 hours)

• Best for: Founders who want pre-vetted talent and ongoing support
• Drawback: Monthly commitment required to get best value

Wishup is a Fully Managed Service Platform and you get a virtual assistant starting from $9.99/hour.

I've tested all three models across different business stages. For most founders earning over $100K/year, the managed route saves more money than it costs because you skip the 20+ hours typically spent interviewing and onboarding.

Step 3: Choose Your Hiring Path Based on Your Situation

There's no single "best" way to hire a VA. Your right path depends on three factors: urgency, budget, and delegation skills.

Freelance Platforms (Upwork, Fiverr, Freelancer)

When this works:

• You need someone for a one-off project
• You have time to screen 15-20 candidates
• You're comfortable managing contractors independently

When this doesn't work:

• You need someone to start this week
• You've never hired a VA before
• You want accountability if things go wrong

My take: I still use Upwork for specialized one-time projects (like a graphic designer for a single campaign). But for ongoing executive assistant work, the quality is too inconsistent and you'll spend more time managing than delegating.

Specialized VA Agencies

When this works:

• You specifically need US-based talent
• You prefer working through an established company structure
• You're willing to pay premium rates

When this doesn't work:

• You're bootstrapped and need to maximize hours
• You need to scale from 10 hours to 40 hours quickly

My take: Great for enterprise companies or well-funded startups who prioritize same-country talent. Less ideal for solopreneurs or early-stage founders watching every dollar.

Managed Platforms (Including Wishup)

When this works:

• You want someone who can start immediately
• You value pre-vetting and ongoing training
• You prefer predictable monthly pricing
• You might need to scale hours up or down

When this doesn't work:

• You only need 2-3 hours per week
• You want direct access to a massive talent pool to screen yourself

My take: Full disclosure—this is the model we built at Wishup because it solved my own problem. After wasting months on bad hires early on, I wanted a system where someone else did the vetting, training, and quality control. That's what we provide now.

Step 4: Write a Job Description That Filters Out 90% of Wrong Fits

Most VA job posts I review are too vague to attract qualified candidates. Here's the template I use:

The difference: Notice how specific this is. When I post this way, I get 80% fewer applications, but 90% of applicants are actually qualified.

Step 5: Screen Candidates Like You're Hiring a Co-Founder

Because in some ways, you are. This person will have access to your calendar, email, and often sensitive information.

Here's my three-stage screening process:

Stage 1: Application Review (5 minutes)

Red flags that disqualify immediately:

• Generic cover letter clearly sent to 50 jobs
• No mention of specific tools you listed
• Grammar errors in a written-communication role
• Resume shows they change jobs every 2-3 months

Stage 2: Skills Assessment (15 minutes of their time)

Send a short paid test before the interview:

• "Audit my Google Calendar and send me a Loom video with 3 suggestions for better time management"
• "Here are 10 emails—draft responses to 3 of them"
• "Research 5 podcast booking agencies and compile in a spreadsheet with pricing"

Pay $20-50 for this. It filters out people who won't do the work.

Stage 3: Interview (30 minutes)

Ask scenario-based questions, not hypotheticals:

• "Walk me through how you managed your last client's calendar when there were double-bookings"
• "Tell me about a time you had to reprioritize tasks because something urgent came up"
• "What's your process when you don't understand an instruction?"

Step 6: Start with a Paid One-Week Trial (Not a Three-Month Commitment)

This is the step most founders skip—and it's why half of VA relationships fail within 60 days.

Here's how I structure trials:

Week 1 Setup:

• Assign 10 hours of real work (not fake test tasks)
• Include 2-3 different task types to test versatility
• Set clear deliverable deadlines
• Schedule a 15-minute check-in on day 3

What to evaluate:

• Do they complete tasks without needing hand-holding?
• Do they ask good questions when something's unclear?
• Do they proactively update you, or do you have to chase them?
• Is their work quality acceptable, or does it need significant revision?

If they pass the trial week, extend to one month. If they pass the month, commit to ongoing work.

What to Delegate First vs. What to Wait On

Not all tasks should be delegated immediately. Here's the sequence I recommend based on working with 500+ founders:

Month 1: Start Here

• Email filtering and inbox management
• Calendar scheduling
• Meeting note-taking
• Basic research tasks

Why these first: They're low-risk, easy to evaluate, and immediately free up time. If your VA struggles here, they'll struggle with everything else.

Month 2-3: Add These

• CRM updates and data entry
• Social media scheduling
• Expense tracking
• Customer support (tier 1 responses)

Why wait: These require more context about your business. Let them learn your voice and systems first.

Month 4+: Consider These

• Content drafting (blogs, emails)
• Project management
• Client communication
• Light bookkeeping

Why much later: These need significant trust and business understanding. Rush this and you'll create more problems than you solve.

The 10 Tasks Founders Delegated Most in 2025

Based on our internal data from 1,500+ active VA placements:

1. Inbox and calendar management (93% of clients)
2. Meeting scheduling and prep (87%)
3. CRM updates and lead follow-ups (71%)
4. Social media scheduling (64%)
5. Expense tracking and receipt management (58%)
6. Research and competitive analysis (52%)
7. Travel booking and logistics (47%)
8. Customer support (first-line) (43%)
9. Project follow-ups and SOP documentation (38%)
10. AI tool setup and automation (29% - new in 2025)

That last one surprised me. More founders are now hiring VAs specifically to implement AI workflows—things like setting up ChatGPT automations, building Zapier connections, or managing AI tool subscriptions.

Common Mistakes I See Founders Make (And How to Avoid Them)

Mistake 1: Hiring for personality over skills

The VA who's friendly and enthusiastic in the interview might not know how to use your CRM or manage your calendar efficiently.

Fix: Test skills before personality. You can train someone to match your communication style. You can't easily train someone on tools they've never used.

Mistake 2: No documented processes

You expect the VA to "figure it out" based on watching you work. Then you're frustrated when they don't read your mind.

Fix: Record a 5-minute Loom video showing exactly how you want a task done. Do this once, reuse forever.

Mistake 3: Delegating everything at once

You hand over 15 different responsibilities in week one. The VA is overwhelmed, you're disappointed, and nobody wins.

Fix: Add one new task per week. Master the basics before expanding scope.

Mistake 4: No regular check-ins

You assume silence means everything's fine. Three weeks later you discover nothing was done correctly.

Fix: Schedule a 15-minute weekly sync for the first month, then move to biweekly once things are smooth.

Why We Built Wishup the Way We Did

I started Wishup in 2015 after burning through five VA hires in six months. Each one seemed perfect in the interview. Each one couldn't handle basic tasks without constant guidance.

The problem wasn't the individual VAs—it was that no one had trained them on what US founders actually need. They knew how to check email, but not how to prioritize a founder's inbox. They could schedule meetings, but not how to juggle timezone conflicts diplomatically.

So we built a program that covers:

• 8 weeks of training (not a one-day orientation)
• Tool-specific training: Google Workspace, Slack, Notion, HubSpot, Asana, and 120+ other platforms
• US business communication norms (because "following up" means different things in different cultures)
• AI productivity skills: ChatGPT, Zapier, Make, and other automation tools founders use in 2025
• Real client simulations: We test VAs on actual founder scenarios before they ever meet you

By the time a Wishup VA appears in your shortlist, they've already completed 50+ hours of training and passed skills assessments.

What Makes Our Model Different:

• Hire in 60 minutes: You can have a working VA by tomorrow if you need it
• Under 5-minute response time during US business hours (we actually track this as an SLA)
• Predictable flat-rate pricing: No surprise invoices from time tracking
• Instant replacements: If a VA isn't working out, we swap them immediately—no additional cost
• Money-back guarantee Try it risk-free
• $100 Benefits: Get a free bokkeeper (worth $500) and business tools ($500) when you hire a Wishup VA.

We serve founders across major US cities including New York, Houston, Seattle, San Francisco, Los Angeles, Chicago, Miami, and Dallas.

Final Thoughts: Hiring a VA Is About Buying Back Time, Not Saving Money

The biggest mindset shift I see in successful delegators is this: They don't ask "How much does a VA cost?" They ask "How much is my time worth, and what becomes possible when I free up 20 hours per week?"

If you're earning $100K/year, your time is worth roughly $50/hour. If you're spending 20 hours on admin work, that's $1,000/week of opportunity cost—$52,000/year.

Hiring a $15/hour VA for those 20 hours costs $15,600/year. You net $36,400 in reclaimed value, plus you get your evenings and weekends back.

That's the calculation that changed everything for me, and it's the one I share with every founder I speak with.

Start small. Test thoroughly. Scale gradually.

And if you want to skip the trial-and-error phase I went through, book a call with our team. We'll match you with a VA who fits your needs—usually within 24 hours.