From “Can We?” to “Should We?” How to Decide What’s Worth Automating in Your Business

Rebecca Wilson
|
October 10, 2025
|
AI & Automation
“If it’s repeatable, it’s automatable.”

That simple phrase often surprises founders when I say it.

Many people think automation means setting up an email sequence, a CRM workflow, or a calendar booking link. But that’s only scratching the surface. Automation isn’t limited to what’s built into your apps, it’s any process that can happen without you manually pressing the buttons.

Whenever someone poses the question "Can that be automated?" It is incredibly rare that I say "no". If something is repeatable, it can be automated.


The more interesting question is — should it be?

From “What can we automate?” to “Should we automate this?”

When I first start conversations about automation, founders often tell me,

“I know there are things we can automate, but I can't see what they are.”

As we start mapping out their workflows, a pattern emerges. By the end of our chat, we’ve usually uncovered too many things that could be automated, and every time, suddenly, the question changes.

It’s no longer “what can we automate?”


It’s “what should we automate?”

That’s the real art of automation, not in finding what’s possible, but in deciding what’s valuable.

“Can we?” is almost always yes

Nearly any digital task can be automated in some way, especially if you add AI into the mix.

If a task happens more than once and follows a predictable pattern, there’s a way to streamline it; whether that’s sending updates, renaming files, logging information, or even creating summaries and reports.

With AI now able to interpret context, even tasks that once required a human touch; like categorising, writing, summarising or interpreting - are becoming automatable.

So yes, you can automate it.


The real question is whether you should.

How to decide what’s worth automating

Over time, I’ve found a simple lens that helps founders decide what’s worth automating and what’s better left manual.

I call it The 3 Rs + 1 H Framework:

Lens Question to Ask Why it Matters
Repetitive Do we do this more than once a week/month? High repetition = high time-saving potential.
Rule-based Can this be done by following clear steps or criteria? The clearer the rules, the safer the automation.
Routine decisions Are the decisions predictable, not strategic? Routine decisions drain attention but add little value.
Human value Does this task benefit from human connection, creativity, or judgment? If yes, automate around it, not instead of it.

If a task is repetitive, rule-based, and low in human value, it’s a great candidate for automation.

If it involves emotion, trust, creativity, or relationship-building, it’s usually better to automate around it - freeing up your time so you can show up where it matters most.

A quick note on edge cases

Even when something looks automatable, it’s worth asking what happens if it goes wrong.

If an error would create real risk - like sending incorrect client information, missing a compliance step, or damaging trust - that’s a sign it might be too high-stakes to automate fully.

In those cases, partial automation (for example, generating a draft for human review) gives you the best of both worlds: efficiency with oversight.

(That’s a whole topic in itself - one I’ll explore more deeply in a future post.)

The Human-First Experiment

A recent example from my own work:


I’ve been sharing my Human-First Automation Playbook on LinkedIn (grab it here if you are interested www.timewisely.co.uk/14-shifts); rather than automating the delivery, I chose to send each copy manually.

Yes, I could have set up an instant download and saved myself time.


But this time, I wanted to do it differently.

Manually sending each one gives me a moment to research who’s requesting it, see how they describe their business, and personally say hello. And once they type their email it redirects to a link directly to the document so they dont hae to wait.

It’s not the most efficient approach (and it definately wouldn’t make sense for every business) but for me, it’s a strategic choice. It helps me stay connected to the real humans behind the downloads.

It’s a perfect example of the “should we?” question in action:


I could automate it. But in this case, the human value outweighs the time saved.

Automation should create space for more meaningful human moments.

How to find your “shoulds”

If you’re wondering where to start, try this simple exercise:

1️⃣ Observe  - Spend a week noting down everything you do more than once.
2️⃣ Evaluate - Circle the ones that don’t need your creativity or decision-making.
3️⃣ Score each task on:

  • Time it takes
  • Frequency
  • Risk if done wrong
  • Human value involved

4️⃣ Prioritise  - Start with the low-risk, high-frequency wins.

Example:

“If your team spends 20 minutes a day updating a project tracker, that’s over 80 hours a year - time that could easily be saved.”

Automation doesn’t need to be big or flashy. It just needs to give you back meaningful hours every week.

Final thoughts - Automation as a thinking skill

Automation isn’t just about technology. It’s about how you think about work.

When you treat automation as a strategic decision (not a default), you build systems that free your people to do their best work.

The goal isn’t to automate everything.


It’s to automate intelligently - so that your business runs smoothly, and your humans can do what humans do best.

The question isn’t “what can we automate?”


It’s “what’s worth automating?”