How to evaluate an EA service in 15 minutes

Most founders spend more time picking a restaurant than choosing an executive assistant service. They browse websites, read testimonials, maybe book a demo. Three months later, they're frustrated with poor communication and missed deadlines.

You can avoid this trap. A proper evaluation takes exactly 15 minutes and four specific questions.

Start with their intake process

Call their sales line. Don't fill out a form. Don't book a demo. Just call and say you want to hire an assistant next week.

A good service will ask about your specific needs before mentioning price. They'll want to know your industry, typical tasks, communication style, and urgency level. Bad services will immediately pitch their packages or redirect you to a generic intake form.

Time this conversation. If they can't give you clear next steps within five minutes, they don't understand their own process.

Ask about their matching methodology

Every EA service claims they "carefully match" assistants to clients. Most are lying. They assign whoever is available.

Ask this exact question: "Walk me through how you would match me with an assistant." Listen for specifics. Do they mention your industry experience requirements? Your communication preferences? Your technical needs?

Time Inc.'s former CEO Andy Serwer once told me that his best assistant understood media industry deadlines without explanation. She knew that "end of day" meant different things for magazine deadlines versus breaking news. That's what good matching looks like.

If the service talks about "personality fit" or "cultural alignment" without asking about your work style, they're guessing.

Test their backup and coverage policies

Here's what separates professional services from freelance coordinators: what happens when your assistant is sick, takes vacation, or quits.

Ask: "If my assistant is unavailable for two weeks, what happens to my work?"

Good services have clear coverage policies. They'll tell you about backup assistants who know your account, handoff procedures, and response time guarantees. Some maintain detailed client notes that any assistant can access.

Bad services will mumble about "finding temporary coverage" or suggest you wait until your assistant returns. This is a red flag. Your business doesn't pause for anyone's vacation.

Demand specific pricing and contract terms

Pricing conversations reveal everything about a service's business model and confidence level.

Ask for their pricing structure upfront. Monthly rates should be clear and published. If they won't quote prices without a "consultation," they're probably overcharging or their pricing is inconsistent.

Good services typically charge between $1,200 and $4,000 per month depending on skill level and location. Services that quote project rates or hourly minimums are usually targeting different clients than busy executives.

Ask about contract length and cancellation terms. Monthly contracts with 30-day notice are standard. Annual contracts with early termination fees suggest the service knows their retention rates are poor.

Look for operational red flags in real time

During your 15-minute evaluation, watch for signs of operational problems:

Does their sales person know their assistants' backgrounds and locations? If they can't tell you whether their assistants are based in the Philippines, Latin America, or the US, they don't know their own team.

Do they ask about your existing tools and systems? A service that doesn't care about your calendar platform, project management setup, or email system will create integration headaches later.

Can they explain their quality control process? Good services monitor work quality, provide ongoing training, and have clear escalation procedures. If they can't describe these systems, they probably don't exist.

The communication test everyone skips

Before ending the call, ask to speak with a sample assistant for two minutes. Not your assigned assistant. Just someone from their team.

This reveals their actual communication quality. You'll hear their English fluency, responsiveness, and professionalism firsthand. You'll also see whether the service is comfortable with this request.

Services that refuse this request or seem surprised by it are hiding something. Confident services will connect you immediately or schedule a brief call within 24 hours.

Skip the demos and testimonials

Most services offer elaborate demos with screen sharing, sample task walkthroughs, and client testimonials. These presentations are scripted marketing theater.

You learn more from a direct 15-minute conversation than from an hour-long demo. Demos show you what the service wants you to see. Direct questions reveal what they actually do.

Testimonials are meaningless unless they include specific results and timeframes. "Sarah helped me get organized" tells you nothing. "Sarah reduced my email processing time from 90 minutes to 15 minutes daily over six weeks" gives you actual data.

Trust your gut on response quality

Pay attention to how the service handles your questions during evaluation. Do they give specific answers or marketing speak? Do they seem rushed or genuinely interested in your needs?

The sales conversation predicts your ongoing relationship. A service that provides vague answers during sales will provide vague work quality later.

If they can't clearly explain their process, pricing, and policies in 15 minutes, they can't manage your work effectively either.

What good looks like in practice

A proper EA service evaluation should leave you with concrete information: monthly pricing, assistant location and background, specific backup procedures, clear contract terms, and realistic timeline for getting started.

You should understand exactly what tasks they handle well and which ones they don't. You should know their communication methods, reporting structure, and quality controls.

Most importantly, you should feel confident that they understand your specific needs and have a plan to meet them.

If you finish the conversation with more questions than answers, keep looking. The right service will make their capabilities and limitations crystal clear from the first call.