An AI agent can compare each client's checklist with what has arrived, list what's still missing, and prepare a specific follow-up for each client. Staff approve every message before it goes out.
For many small firms, the work itself isn't what holds a file up. More often the client hasn't sent everything yet, and someone on the team has to go and get it.
That's harder to absorb when the team isn't growing. CPA Canada says the number of CPAs working in Canada hasn't changed much since 2011, while the number of tax filers has risen and there are about 20% more small businesses. In Wolters Kluwer's 2023 survey of Canadian firms, most of them sole practitioners or firms of two to five people, 66% said it was hard to hire the staff they needed.
Missing paperwork got worse this past spring, too. When slips were missing from the CRA's Auto-fill service ahead of the April 2025 deadline, CPA Canada called the problem pervasive, and preparers had to enter the missing information by hand.
What does document chasing involve?
The steps are simple, but there are many of them. Someone checks the client's checklist against what has come in, emails about the gaps, waits, checks again a few days later, finds two items still outstanding, and follows up again. Each round only takes a few minutes. Across dozens of clients, it adds up to hours, and each round pulls someone away from the work that needs their expertise.
Can AI chase missing client documents?
Yes. The agent reads each client's checklist and compares it with what's in that client's folder in Microsoft 365 or Google Drive. It lists what's outstanding and prepares a follow-up for each client that names the exact items, written the way your team writes. If nothing arrives after a week, it prepares a gentler reminder.
A follow-up might read like this (the client is invented):
Hi Daniel,
Thanks for the bank statements. To finish the September year-end we still need the loan statement as of September 30 and the invoice for the equipment you bought in July.
You can add them to the same folder as before. If the equipment was leased, just let us know.
Thanks, Sarah
Naming the exact documents is what gets a response. A request to "send your remaining documents" is easy to put off, while "we need the July equipment invoice" is easy to act on.
Does it email clients on its own?
No. Staff review each follow-up and send it. Anything involving fees or a judgement call about a client stays with your people.
The agent runs inside the AI tool your firm already pays for, under your existing agreements, and documents stay in your folders. Most firms already have one: Wolters Kluwer's 2025 research found that 62% of Canadian firms use AI at least weekly.
What if we already use a client portal like TaxDome, Karbon or Canopy?
Portals like these can already send clients automatic reminders about outstanding requests. Those reminders are usually a general nudge to log in and upload what's outstanding.
An agent adds something different. It works out exactly which documents each client is missing and writes a short, specific follow-up in your firm's voice, which tends to get a faster reply. It can also cover clients who rarely use the portal.
Because your requests live in the portal, the setup would look different from the shared-folder version above. It's best to look at how your firm uses the portal first, and then decide whether an agent would help.
How do you know it's working?
Treat it as an investment you can measure. Record a baseline for a few weeks before you start, then compare after the first month:
- Days from the first request to a complete file
- Follow-ups sent per client
- Staff hours spent chasing each week
Days to a complete file matters most, because it decides when billable work can start.
Where should a firm start?
Pick one service line, such as corporate year-ends. Gather your checklists and a few follow-ups your team has already sent, then run the agent on live clients for two weeks with staff approving every message.
Sources CPA Canada: Canada needs more CPAs; Wolters Kluwer 2023 Canadian tax season challenges report; Investment Executive: tax preparers tapped out as tax slips remain missing in CRA portals; Wolters Kluwer Future Ready Accountant, Canada.