Chasing is rarely anyone's actual job. It's something everyone does a little of, between the work they were hired for. That's why it's one of the best candidates for automation in a finance practice: the task is repetitive, the rules are clear, and the cost of it slipping lands on the people least able to absorb it.
Why chasing slips
Nobody holds the whole list
What's outstanding for each client tends to live in several places at once: an inbox, a task list, a spreadsheet, somebody's memory. Each is partly right. None is complete. So the question "what are we still waiting for?" takes twenty minutes to answer, and gets asked less often than it should.
Reminders cost goodwill
The first request is easy to send. The third feels awkward, because it comes from a person, and it reads as that person being impatient. So it gets softened, delayed, or not sent at all.
The busy weeks are the worst weeks
Chasing competes for time with the deadline work it exists to support. When the pressure is highest, chasing is the first thing dropped, which is precisely when it was needed.
What a chasing system actually holds
Sending emails is the easy part. The value of a chasing workflow is that it keeps one accurate list, and everything else follows from that list. For each client and each period, it holds:
- what's due, and by when;
- when each item was requested, and how many times;
- what has arrived, and when it arrived;
- which named person at the firm takes over if the reminders run out.
With that list in one place, "what are we waiting for?" becomes a screen, not a meeting.
How the reminders run
- The request goes out in your firm's name, from an address clients already recognise, in wording your firm wrote.
- Reminders follow a schedule you set. For example, a gentle nudge after five days, another after ten, and a firmer note the third time.
- Reminders stop the moment the item arrives. Nothing damages trust faster than chasing a client for something they sent yesterday.
- After the last reminder, a person takes over, with the full history in front of them, so their call starts from the facts.
The hard part: knowing it arrived
Stopping reminders at the right moment depends on the system knowing that a document has come in. There are three common ways to do that, and most firms use more than one.
- A link per request. The client uploads through a link tied to that specific item, so arrival is certain. It's the most reliable option and asks the most of the client.
- A monitored inbox. Clients reply or forward as they always have, and the system matches the sender and attachment to what's outstanding. It's easiest for clients and needs the most careful matching.
- The ledger itself. For some items, the evidence of arrival is in Xero or QuickBooks rather than in a file, and the system can check there.
Where people stay in the loop
Automating the chase isn't the same as automating the relationship. A good chasing workflow leaves three things firmly with people:
- The words. Your firm writes every template. The system sends them; it doesn't compose them.
- The exceptions. A client who's unwell, bereaved or in dispute can be paused with one click, and stays paused until someone decides otherwise.
- The escalation. When reminders run out, a named person picks it up. The system never escalates by getting louder.
Automation should take away the remembering, not the relationship.
Start small
The best first chasing workflow covers one document type, for one group of clients, for one period. Monthly receipts for bookkeeping clients is a common starting point. Run it for two or three cycles, look at how many items arrived without a person having to chase, and adjust the schedule and the wording before extending it to anything else.
That small start also shows your team the list in action. Once people trust the list, they stop keeping their own, and that's when the time savings actually appear.