TL;DR
Automate work that repeats weekly, follows the same steps and has one clear owner. Leave judgement calls and anything you cannot describe as a rule alone for now. Measure the result in hours returned per month, not in the number of tools connected.
Start with the work you repeat weekly
The first candidate is rarely the most exciting task. It is the one that happens every week, takes the same steps each time and produces a predictable output. Report assembly, invoice routing, lead assignment and status updates are typical examples.
If nobody can write the steps down, the process is not ready. Automating an undefined process only makes the confusion run faster.
Good first candidates
- Moving data between two systems that both have a stable interface
- Sending the same notification when a defined event happens
- Assembling a recurring report from sources that do not change shape
- Routing inbound leads to the right owner based on stated criteria
- Chasing documents or approvals that are simply waiting on a reminder
Leave these alone for now
- Anything that requires a judgement call on money, contracts or hiring
- Processes where the steps change every month
- Tasks that happen once a quarter and take an hour
- Any workflow where nobody will own the failures
Measure hours, not tool counts
A workflow that saves twenty minutes a week is not worth maintaining if it needs an hour of attention each month. Write down the before number accurately, then check it after a full month of real use.
The other number worth tracking is failure rate. An automation that runs clean most of the time and quietly drops a lead is worse than the manual process it replaced. Add an alert for the case where it should have fired and did not.