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What security training does a small team need? Start with real decisions.

A woman explains a diagram on a whiteboard to three colleagues at a table, one of them with a laptop open.

A payment change that seems to come from a client. An AI tool that wants the whole Drive. Good training is built around moments like these, and every lesson ends with a next step and a person to tell.

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What should security training cover for a small business?

Teach the decisions your team actually makes: checking an unusual request, protecting sign ins, sharing client files, connecting AI tools and reporting a mistake quickly. Use short examples from their own work, and name one person to contact.

Record who took part. Then practise the same decisions again when the work or the tools change.

What is phishing?

What phishing is.

A message that pretends to come from someone you trust, such as a client, a supplier or your own bank. It wants you to click a link, pay an invoice or type a password.

Most of it arrives by email. The same trick also turns up in chats, text messages and shared documents. The defence is a habit: check through a route you already know before you act.

Begin with a moment from a normal workday.

A client seems to ask for a change to their payment details. An assistant asks for access to an entire Drive. A freelancer wants to send project files to a personal account. People at an agency will recognise each of these. A lesson built around them gives people something to do. A slide full of threat terms usually does not.

So choose examples for the roles in your team.

  • designers

    File links and browser tools.

    Who a sharing link reaches, and what a browser extension can read.

  • developers

    Keys, packages and agents.

    Clear rules for secrets, for the code they pull in and for what an agent may change.

  • account managers

    Unusual client requests.

    How to check a surprising request through a route they already know.

Show the next step, not only the warning sign.

It is easy to tell someone to be careful. Be specific about what they should do instead. For a surprising payment request, contact the client through a route you already know. For a new app permission, check what access it really needs before you approve it. For a file shared by mistake, report the details quickly, so the right person can act.

Use a made up example based on a real workflow, with no live client information in it. Ask the team what they would do next. A good answer names a person, a channel or a check they can run. If people know the warning signs and still do not know who to tell, the lesson is not finished yet.

a lesson that changes a workdayone moment

An email from a client asks you to pay the next invoice to new bank details. The payment run is today.

  1. 1

    Recognise it.

    New bank details, by email, in a hurry. That is the unusual request.

  2. 2

    Check it through a route you know.

    Call the client on the number you already have, never the one in the email.

  3. 3

    Report it while it can still be handled.

    Tell the person who runs payments, even if the request turns out to be real.

One lesson, three steps. The last one names a person.

Provider guidance: NCSC (United Kingdom): spotting cyber attacks

Include the tools your team uses now.

AI assistants bring familiar questions into a new setting. What may I share? What can this tool reach? Which action needs a yes first? Show how a useful connector can ask for more access than the task needs. And make it clear that a convincing answer from an assistant is no proof that an action is allowed or safe.

Keep these lessons practical. A copywriter can practise picking a harmless example instead of an unpublished client brief. A developer can compare read only access with a tool that may change live data. Do not assume everyone uses the same assistant, or that one general rule replaces what a client requires for their own information.

What is an AI connector?

What an AI connector is.

A connection that lets an AI assistant use another tool: a Drive, a project tracker, a client’s website. Most use MCP, the open standard that lets an AI assistant use a tool.

Each connector is access. It stays in place until someone removes it.

What counts as a secret?

What counts as a secret.

Anything that lets someone act as you or as your client: passwords, keys, tokens, recovery codes.

They belong in a password manager. Never paste them into a chat with an assistant, a shared document or a code repository.

Build a small routine the team will keep.

Give new people the basics before they get access to client work. Follow up with short refreshers tied to a change: a new tool, a new client requirement or a mistake worth learning from. Plan them as work. Asking people to finish training in their spare time tells them the business does not think it matters.

Keep a record of who completed what. Just do not confuse completion with understanding. Go back to a scenario in a team meeting and see whether people can name the next step. Welcome early reports, and never shame anyone in public. When someone raises something they are unsure about, thank them and sort it out. That response teaches the team as much as any course.

training on your team26.09.2026

  • Anayearly refresher24.09.2026
  • Lucaintroduction26.09.2026
  • MiraintroductionDue

2 of 3 finishedfinished is not the same as understood

A completion record: names, lessons, dates. It shows who took part, not what they will do next time.

Provider guidance: NCSC (United Kingdom): free security training for staff

Connect training with the rest of your security work.

cybee includes security training in the Proof plan: short lessons on topics such as a lost laptop, AI tools, secrets and permissions. You assign them from your AI assistant in one sentence, and each finished lesson is recorded next to the protection and security work your team already does. The cybee icon in the Mac’s menu bar shows each person the training that is due, so nobody has to open yet another app.

When a client asks for proof of training, use the completion record, and say who and what it covers. The Trust Passport for your Macs is a different record, and it does not prove that every training or policy requirement is met. Training pays off when people make the next decision well, and the business can show what it actually provided.

A woman writing in a notebook next to her MacBook at a kitchen table.
Sat 26 Sep 09:50
Training dueMira’s MacBook AirThe security introduction
LessonPayment requests
Assigned byAna
One icon in the menu bar. The lesson waits there until Mira has a moment.
Does a finished lesson prove my team is safe?

What a finished lesson shows.

It shows that a person finished a lesson, and when. It does not certify your company, and it does not promise what anyone decides the next time an odd request arrives.

That is why the record sits next to the conversations in your team meetings, not in place of them.

What to remember.

  • Use the situations your people face in client work.
  • End every lesson with a clear next step.
  • Keep the record of who took part, and check understanding separately.

Sources and further reading.

Product scope and provider guidance can change. Check the linked source for your own setup. Stuck on a word? Look it up in the security glossary.

Put it to work.

Short lessons, assigned from your AI assistant in one sentence, with a record of who finished.

See how training works

Your next client will ask. Be ready.

curl -sSf https://get.cybee.dev | sh

Press Command and C to copy.

Send the setup guide to my Mac

Run it in Terminal, a chat, your IDE or a CLI. Keep working where you started.

Free for every Mac with an Apple chip · Asks before it changes your Mac What it installs Read the install script

Install cybee on your Mac.

Not at your Mac? Send these steps to yourself.

Needs a Mac with Apple silicon. To check, open the Apple menu and choose About This Mac: next to Chip, the name starts with Apple M. Intel Macs are not supported.

curl -sSf https://get.cybee.dev | sh

Run it in one of these places. Keep working there.

  • Terminal

    Open Terminal, paste the line and press Return.

    Then cybee status

  • Chat

    Paste it into your AI assistant’s chat and ask it to install cybee. This needs an assistant that runs on your Mac. A chat in a browser tab cannot reach your Mac.

    Then /cybee in the same chat

  • IDE

    Paste it into the terminal in Cursor, or ask Cursor to run it.

    Then /cybee in Cursor’s chat

  • CLI

    Ask Claude Code or Codex to run it. macOS asks for your password in a window.

    Then /cybee in the same session

Your Mac may ask for your password. That is macOS checking it is you. When System Settings opens, switch on CybeeES under Full Disk Access. Protection starts then. Full Disk Access lets cybee watch what programs do. Your files never leave your Mac.

Want the Proof plan?

The 14 day trial starts in your AI assistant, after cybee is installed. Ask for a Proof plan feature, such as the Trust Passport. The link arrives in the chat and leads to Stripe, the payment service.