Never Assume Someone’s Further Along Than They Are

We’ve all done it — looked at someone’s online work and thought, “They’ve got this sorted.” Until we sit across the table from them and realise: they don’t.

That was me this week.

A client came to me for training in digital marketing. I’d seen their content, their design, their online presence. It looked good. Professional. Polished. So I turned up, ready to teach advanced techniques — funnel design, customer journey mapping, layered email automations.

But five minutes in, I was dragging the conversation back to basics — things like linking a domain to a website, scheduling a social post, and understanding the difference between organic and paid reach.

They weren’t an expert. They had people. And those people made them look like an expert. But that’s not the same thing. Not even close.

We Keep Teaching at the Wrong Level

This experience punched a hole in something I see all too often — our assumptions about what people already know.

When you’ve been in a field long enough, it’s easy to forget what it was like to be new. You throw out jargon like “conversion pathways” and “lead magnet segmentation,” thinking it’s common sense. It’s not.

The gap between perceived and actual knowledge is a silent killer in training, onboarding and client success. You don’t just miss the mark — you alienate the person entirely.

And worse still, they nod along to save face.

We’re Embarrassed to Ask for Basics

My client didn’t say they didn’t know how to do basic things. In fact, they probably thought they were supposed to know by now. They didn’t want to look foolish.

And that’s the problem.

People will choose silence over embarrassment. Every time. And when they do, they miss out on the very thing they came for: knowledge. Confidence. Capability.

If I’d just asked, “What do you already know? What do you want to know?” — we would have gotten further, faster.

But I assumed.

And assuming is lazy empathy.

The Real Job Is Meeting People Where They Are

We don’t help people by being impressive. We help them by being accessible.

Training, teaching, mentoring — none of it works if you’re more concerned with showing what you know than finding out what they need.

Next time, I won’t come in hot with my best slide deck. I’ll come in with a question.

“Where are you actually at?”

That question will save everyone a lot of time, shame and frustration — including me.

That's all for this weekend. Just one short read about how our assumptions can cost us dearly.

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See you next Saturday.

Dante

P.S. I write, speak and train all over the place — check below for some helpful links.

Dante St James

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