What to Automate (And What Not To)
Automation promises efficiency, but not every task benefits from it. Understanding which activities to automate—and which require your personal attention—is crucial for getting meaningful results.
Good Candidates for Automation
Tasks that work well automated share these characteristics:
- Repetitive: You do them the same way repeatedly
- Rule-based: Clear triggers and predictable actions
- Low-stakes: Errors don't damage client relationships
- Time-consuming: They eat into productive hours
- Process-driven: Steps can be documented and followed systematically
Keep Human
Certain tasks benefit from your personal touch:
- Relationship building: First conversations, important check-ins
- Complex negotiations: Scope discussions, pricing conversations
- Sensitive communications: Delivering difficult news, handling complaints
- Creative decisions: Strategy, direction, judgment calls
- Custom solutions: Unique situations requiring tailored responses
The goal isn't to automate everything—it's to automate the mundane so you have more energy for what matters.
💡 Practical Example
Maria automated her invoice reminders but kept personalising project kickoff emails. The reminders were identical each time and required no relationship finesse. Project kickoffs, however, benefited from acknowledging the client's specific situation and setting a collaborative tone.
Invoicing Automation
Invoicing is often the first process freelancers automate, and for good reason. Manual invoicing consumes time and introduces errors, whilst delayed invoices delay payment.
What to Automate
- Invoice generation: Pull client details and line items from templates or project data
- Numbering: Automatic sequential invoice numbers
- Calculations: VAT calculations, currency conversions, totals
- Sending: Scheduled dispatch or one-click sending
- Tracking: Monitor when invoices are viewed and paid
- Recording: Automatic logging to your accounting system
Recurring Invoices
For retainer clients, set up recurring invoices that generate and send automatically. No more remembering to invoice on the first of each month—the system handles it.
Payment Integration
Connect invoices to payment processors. When clients receive invoices with embedded payment links, they can pay immediately. Less friction means faster payment.
Invoice Checklist
Before automating, ensure your manual process is solid:
- ☐ Invoice includes all required legal elements
- ☐ Payment terms are clear and consistent
- ☐ Bank details or payment links are correct
- ☐ Branding is professional and consistent
- ☐ VAT handling is accurate (if registered)
Payment Reminders
Chasing payment is uncomfortable and time-consuming. Automating reminders removes the emotional burden whilst ensuring consistent follow-up.
Reminder Sequence
Design a sequence appropriate for your business:
- Day before due: Friendly reminder that payment is coming up
- On due date: Payment is due today
- 7 days overdue: Gentle follow-up
- 14 days overdue: Firmer reminder
- 30 days overdue: Final automated notice, then personal contact
Tone Matters
Write reminder templates in your voice. They should be professional but not aggressive—assume good intentions. Most late payments result from oversight, not malice.
When to Step In
Know when automation should hand over to personal contact. Significantly overdue invoices or repeated late payments require human conversation about underlying issues.
💡 Practical Example
David set up automatic reminders but kept thanking clients personally when they paid. The reminders handled the chasing, whilst his personal thank-you notes reinforced positive client relationships and encouraged future prompt payment.
Client Onboarding
New client setup involves many small tasks. Automating the sequence ensures nothing is missed and clients receive a consistent experience.
Onboarding Workflow
When a new client signs up, trigger:
- Welcome email with next steps
- Client record creation in your CRM
- Intake form dispatch
- Calendar link for kickoff meeting
- Contract and proposal delivery
- Project folder creation
- Internal task list generation
Automated Document Preparation
Use document templates that auto-populate with client details. Contracts, proposals, and project briefs can pull from your CRM, reducing manual typing and errors.
Scheduling Automation
Scheduling tools eliminate email tennis when booking meetings. Send a booking link and let clients choose from your available slots. Confirmations and reminders send automatically.
Contract Signing
Paper contracts or email attachments create friction. Digital signature tools streamline agreement execution.
E-Signature Benefits
- Speed: Contracts signed in minutes, not days
- Tracking: See when documents are opened and signed
- Storage: Automatic archiving of signed agreements
- Reminders: Automated nudges for unsigned documents
- Legality: E-signatures are legally binding in the UK
Template Library
Create contract templates for different service types. When starting a new project, select the appropriate template, add client details (automatically where possible), and dispatch for signature. No rebuilding contracts from scratch.
Signing Workflow
A streamlined sequence might be:
- Generate contract from template with client details
- Review and customise any project-specific terms
- Send for electronic signature
- Receive notification when signed
- Automatic storage to client file
- Trigger next onboarding steps
Email Templates
You likely send similar emails repeatedly: enquiry responses, project updates, availability notices, thank-you messages. Templates save time without sacrificing quality.
Essential Templates
Build templates for common scenarios:
- Initial enquiry response
- Project kickoff confirmation
- Deliverable submission
- Revision request acknowledgement
- Project completion and handover
- Follow-up for feedback or testimonials
- Re-engagement with past clients
- "Not available" response with alternatives
Personalisation Hooks
Templates shouldn't feel robotic. Build in personalisation points: client name, project specifics, relevant context. A good template is 80% standard, 20% tailored.
Template Management
Store templates where you can access them quickly. Email client templates, text expanders, or project management tools all work. The key is speed and accessibility.
💡 Practical Example
Sophie created templates for her five most common emails and measured the impact. Previously, these emails took 10-15 minutes each to write carefully. With templates, she spent 2-3 minutes personalising. Over a month, she saved roughly 8 hours—time reinvested in billable work.
The Automation Stack
Building an effective automation system often involves connecting multiple tools. Here's how to approach it:
Core Categories
- Central hub: CRM or freelance platform holding client data
- Invoicing: Invoice generation and payment processing
- Communication: Email with templates and scheduling
- Documents: Contracts, proposals, e-signatures
- Scheduling: Meeting booking and calendar management
- Automation: Connecting tools and triggering workflows
Integration Approaches
Native integrations: Many tools connect directly. Check what your primary tools offer before adding connectors.
Automation platforms: Tools like Zapier, Make, or Power Automate connect applications without coding. When X happens, do Y.
All-in-one platforms: Some tools handle multiple functions internally, reducing integration needs. FreelancerHub, for example, connects client management, invoicing, and payment tracking in one system.
Start Simple
Don't build complex automation immediately. Identify your biggest time drain, automate that, then expand. Complex systems built all at once often break—and you won't know which part failed.
Return on Time Investment
Automation requires setup time. Calculate whether it's worthwhile:
Time Calculation
- Estimate time spent on the task monthly
- Estimate initial setup time
- Estimate ongoing maintenance time
- Calculate payback period: Setup time ÷ Monthly time saved
Worth Automating?
A rough guideline: if the payback period is under 6 months, it's likely worthwhile. But also consider:
- Mental energy saved (not just time)
- Reduced errors and mistakes
- Improved client experience
- Scalability for business growth
Automation Checklist
- ☐ Identify your top 5 time-consuming admin tasks
- ☐ Prioritise by potential time savings
- ☐ Research tools for each category
- ☐ Implement one automation at a time
- ☐ Test thoroughly before relying on it
- ☐ Document your systems for future reference
- ☐ Review and refine quarterly
Effective automation isn't about removing yourself from your business—it's about removing unnecessary friction so you can focus on work that matters. Start with one process, perfect it, then expand your automated systems gradually.