What to ask before signing with any EA service

Most EA services will tell you they're different. They'll promise dedicated assistants, rigorous vetting, and seamless communication. Then you sign the contract and discover your "dedicated" assistant rotates every three months.

The wrong questions get you generic answers. The right questions reveal how the service actually works.

Who exactly will be doing the work

Don't ask "Will I have a dedicated assistant?" Everyone says yes. Ask "What happens if my assistant quits or goes on vacation?" This tells you if they have backup systems or if you'll be scrambling to brief someone new.

Ask for the assistant's resume before you sign anything. Some services assign college interns to executives paying $4,000 per month. Others won't show you resumes until after you've paid.

Get specific about location and time zones. "Our assistants are US-based" often means they're US citizens working from the Philippines. Nothing wrong with that, but you should know.

How they handle the money conversation

Pricing pages list starting rates. Real costs include setup fees, minimum commitments, and overage charges. Ask "What will I actually pay in month six?" Include examples of typical tasks you'll assign.

Some services charge extra for "complex" tasks but won't define complex until you're already using them. Calendar management might be included. Travel booking might cost extra. Get the task list in writing.

Ask about unused hours. Do they roll over? Disappear? Convert to credits? This matters more than the hourly rate if your workload varies.

The trial period reality check

Free trials sound great until you realize they're using their best assistant as bait. Ask "Will my trial assistant be my permanent assistant?" Most services say no.

Find out what happens during onboarding. Some services dump you into their system with no guidance. Others assign account managers for the first month. The difference affects how quickly you'll see results.

Test their response time during the trial. Send a Friday afternoon email. See how long it takes to get an answer. This tells you more about their operations than any sales pitch.

What happens when things go wrong

Every service will mess something up. The question is how they handle it. Ask for specific examples of mistakes they've made and how they resolved them.

Get cancellation terms in plain English. Some services require 30-day notice. Others lock you in for six months. A few will refund unused balances. Most won't.

Ask who you contact when your assistant misses a deadline or books the wrong flight. Is it the assistant directly? A manager? A support ticket system? This matters when you're dealing with urgent fixes.

The questions they don't want to answer

Ask about assistant turnover rates. High-quality services track this metric and share it. Services with retention problems won't give you numbers.

Find out how many clients each assistant handles. Some services spread assistants across 10+ clients. Others cap it at three or four. This affects the attention your work receives.

Ask what training assistants receive beyond their initial hiring. Good services invest in ongoing education. Cheap services hire once and hope for the best.

The litmus test question

Here's the question that separates professional services from resume mills: "Can I speak with three current clients who've been with you for over a year?"

Legitimate services will connect you with happy long-term clients. Services with retention problems will deflect with privacy policies or offer to share testimonials instead.

The clients they choose tell you something too. If every reference is a solopreneur, they might not handle complex corporate needs. If every reference runs a similar business to yours, that's actually a good sign.

Don't sign anything until you've had these conversations. The 20 minutes you spend asking hard questions will save you months of frustration later.