Most approvals do not fail because somebody said no. They fail because nobody said anything — it sits with a person who is on holiday, or who read the notification on their phone and meant to come back to it, and the work behind it waits until somebody notices and asks.
The native build
This is the step people leave out, and then wonder why nothing fires.
monday can notify somebody when a date arrives. It cannot notify somebody because a status has been sitting a while, because a status column does not record when it was set. So the first automation is not the reminder — it is the date:
Then the reminder hangs off it:
Two automations, and you can now see and chase anything that has stopped moving. For a lot of teams that is the whole problem solved.
Why it stops working
Usually within a fortnight.
The first one gets read. The fifth is recognised before it is opened, and by the twentieth the sender is a category the recipient has learned to skip. That is not rudeness; it is what anybody does with a notification that arrives whether or not it matters.
The damage is worse than nothing, because now there is a system that appears to be chasing and is not. The approval is not just late, it is late and unattended, and the person who set the automation believes it is handled.
Three rules that keep a chase worth reading:
The better question
Which is not the same as what is overdue.
A date-based reminder answers this passed its date. The useful question is what is somebody else waiting on, and for how long — because that is the order in which things should be chased, and it has nothing to do with whether a date was ever set.
You can approximate it natively with a board view filtered to the approving labels and sorted by the date column. It is worth building. It will only ever cover one board, which is fine until approvals live on four of them.
Questions
Add a date column set by an automation whenever the status changes, then: when date arrives and status is still the approving label, notify the person. The date is the part people leave out, and without it there is nothing for the reminder to fire from.
Once after a day, then once more, then stop and tell a human. A reminder that repeats indefinitely trains the recipient to filter it, and after that the approval is in a worse position than if nothing had been sent at all.
The approver first, always. Escalating on the first miss costs you the relationship and teaches people that the tool reports them. Escalate only after the approver has genuinely had a chance and has not taken it, and make sure a person chose to escalate rather than a schedule.
What we built
Deliberately, and this is the part we argued about most.
Signoff knows how long each approval has sat and with whom, across every board, and it surfaces the ones that have stopped moving in one list ordered by how long they have been holding somebody up.
What it does not do is send the chase by itself. It shows you what it thinks should be chased and you press the button, or you press leave it — because you know that Dana is on annual leave and no piece of software does. Automatic nagging is the thing that stops being read; a message somebody chose to send is not.
Escalation exists and asks first. It never goes to a manager on the first miss, and it never goes anywhere without somebody deciding it should.
Keep reading
What to do in the next twenty minutes when a file was replaced after sign-off, how to work out what each approver actually saw, and the habits that stop it recurring.
What a dashboard widget genuinely solves, why a cross-board view quietly stops matching some boards, and the half of the problem a list of items cannot cover.
One board, one status column, and one automation per transition.
Three approvals a month, free, with the chasing included. Enough to find out how long things have actually been sitting.