Hiring admin help has changed. In 2026 the question isn’t only “Can this person do the task?” but “Can they do it well with the AI tools that are now available?” An assistant who uses AI carefully can get through more work, with fewer errors, in the same hours.

Here’s what to look for when you hire, and the questions that help you spot the difference.

1. A clear area of strength

General help is useful, but the most effective assistants are strong in a few areas, such as inbox and calendar management, CRM and email marketing, or social media. Ask candidates where they do their best work and for examples.

2. Practical experience with the right tools

Look for hands-on use of tools that match your business:

• An AI assistant such as ChatGPT or Claude for drafting and summarising
• An automation tool such as Zapier or Make
• A meeting note-taker such as Fathom or Fireflies
• The platforms you already use, such as your CRM, booking system or email marketing tool

Question to ask: “Tell me about a task you sped up with AI. What did you do, and how did you check the result?”

3. A habit of checking AI work

This matters more than any tool. AI can produce confident mistakes: wrong dates, invented facts, the wrong tone. A good assistant treats AI output as a first draft and checks it before it reaches you or your clients.

Question to ask: “What do you do before sending something AI helped you write?”

4. Care with your data

Your assistant will have access to email, client details and possibly payments. Look for someone who uses a password manager, doesn’t paste sensitive information into AI tools, and is happy to sign a confidentiality agreement.

5. Good written communication

Clear updates, good questions and short written processes save you time. A strong assistant writes down how you like things done so the work stays consistent.

6. Judgement and a human touch

AI doesn’t know which client needs a phone call instead of an email, or when a deadline can flex. Look for someone who asks when something is unclear and flags problems early.

A quick hiring checklist

• Ask for a real example of AI-assisted work and how it was checked
• Give a short paid test task that matches your actual work
• Check how they share passwords and handle client data
• Agree on hours, update frequency and how you’ll communicate
• Start with a few tasks and add more as trust builds

Prefer a team that already works this way?

My Admin Support Team is a small team based in Baguio City, Philippines. We use AI to speed up routine admin, and I check every task before it reaches you.

About the author

I’m Feby Lunag, based in Baguio City, Philippines. I’ve worked remotely for 13+ years, including as Executive Assistant to a SaaS CEO and about 9 years with a US publicly listed company, with 100% Job Success on Upwork. Today I help business owners set up AI-assisted admin, either hands-on or through my Admin Support Team.