Automating the Boring Stuff
The highest-ROI automations for an owner-operator's first year.
Notes from Randall Harper. Thirty years working alongside owner-operators, executives and boards — companies of all types and sizes — across entertainment & media, hospitality, service based business, lifestyle businesses, financial services, retail and not-for-profit, in Australia, Asia, the United Kingdom and the United States. What follows is the thinking I keep returning to.
The principle: automate the repeating
Any task you do more than once a week, in the same way, with no real judgement required, is a candidate for automation. The point is not to look modern; it is to reclaim the hours you currently spend on work that does not need a human. Start with the dullest, most repetitive tasks. Save the interesting ones — the ones where your judgement actually adds value — for yourself.
The high-ROI starting list
- Automatic invoice send-out when a job is marked complete.
- Automatic payment reminders at 1, 7, and 14 days overdue.
- Booking confirmations and reminders by SMS the day before.
- Review request emails 48 hours after job completion.
- Lead capture from your website routed straight into your CRM or inbox.
- Recurring invoices for retainer or contract work.
Tools that do the heavy lifting
You rarely need code. Zapier, Make, and the native automations inside Xero, ServiceM8, HubSpot, or your job management tool cover almost every small-business workflow. Set up one automation a week for a month and you will have reclaimed hours per week, permanently, for the cost of an afternoon's setup time.
Automation hygiene
Every automation needs an owner. Document what it does, when it fires, what could go wrong, and how to turn it off. Test it monthly. The downside of a silent broken automation — invoices not sending, leads not arriving — is large enough that a quarterly audit pays for itself many times over.
What not to automate
Anything where the customer would notice the lack of a human touch. Apology emails. Quotes for unusual jobs. Negotiations. Hiring conversations. The skill is not maximising automation; it is choosing which work deserves your attention and which work no longer does.
Want this as a PDF?
Tell us where to send it and we'll email you a copy to keep.
The contents of this paper are the opinion of Clear Point Advisory only. Readers should rely on their own judgement and obtain professional advice appropriate to their circumstances.