What I look at before recommending AI to a business

Lately, I've been thinking about why so many businesses feel disappointed after investing in AI.

The story is usually very similar.

They hire an AI expert. A few automations get built, maybe an agent gets deployed, and everyone gets excited because something has finally happened.

To be fair, it does create value.

A few months later, the founder is still working ridiculous hours. Operations still feel messy. Marketing still isn't running consistently. They still don't feel fully in control of the business.

"Do I just need more AI?"

I'm not convinced that's the right question.

If I was working with that business, I probably wouldn't spend much time talking about AI in the first meeting.

I'd spend most of my time trying to understand the business.

Where is it going?

What's changing over the next year?

What are you actually trying to achieve?

Once I understand that, I'd ask them to walk me through how the business works today.

How do you find customers? How do you sell? How do you onboard people? How do you recruit? Which parts of the week feel chaotic? Which tasks always seem to take longer than they should?

Most of that conversation is me listening.

People are usually very aware of the pain points. They've just never had the time to step back and look at everything together.

After that, I look at the technology.

What systems are you using?

How connected are they?

Where is information being copied from one place to another?

Are there systems you've outgrown but nobody wants to touch?

How open are you to changing the stack if there is a better way?

By then, I normally have a pretty good picture of what's actually going on.

Some opportunities involve AI.

Some involve automation.

Some involve redesigning a process that's been slowly getting worse over the years.

Sometimes the biggest win is simply removing work that nobody should be doing anymore.

The reason I approach it this way probably comes from my background.

I spent more than sixteen years working in technology, including roles at Accenture and Salesforce, helping deliver transformation programmes for some of the largest organisations in the world.

One thing I took away from that experience is that successful technology programmes rarely start by asking:

"Which tool should we buy?"

They start by understanding the business, agreeing where it's heading, and making technology decisions that support that direction.

I don't really see a reason why small businesses should be any different.

Obviously, the scale is different. The budgets are different. The speed is different.

The thinking doesn't have to be.

That's why I've become a bit uncomfortable with the way AI is being adopted in some businesses.

There's so much focus on building the next agent that we're skipping the conversation about how the business itself needs to evolve.

AI is genuinely transformational.

I just think it works much better when it's part of a broader plan than when it's treated as the whole plan.