04 - 9 Things I Learned After Teaching 1,300 Professionals How to Sell

I didn’t plan to teach.

I planned to build...

But when you scale a business to 700+ clients across 65 industries — and you’re watching the same problems repeat across every sector, every size, every market — you realise the knowledge has value beyond your own pipeline.

So I packaged it. Built programs. Taught it...

1,300 professionals later — here’s what I actually learned.

1. Most people are selling before they’re ready to sell.

They haven’t defined who they serve. They haven’t built a clear offer. They don’t know what problem they actually solve at a commercial level.

But they’re out there pitching anyway.

And then wondering why nothing converts.

The sequence matters. Clarity first. Sales second. Most people have it backwards.

2. Confidence is not a sales skill. It’s a byproduct of preparation.

Everyone wants to feel confident in sales conversations.

But confidence doesn’t come from mindset work. It comes from knowing exactly who you’re talking to, what they need, why your solution fits, and what happens next.

Prepare the structure. The confidence follows.

You cannot shortcut this with motivation.

3. The follow up problem is actually a pipeline problem.

“I’m not good at following up” is one of the most common things I heard.

But following up isn’t a discipline issue. It’s a structural issue.

If you don’t have a defined next step agreed at the end of every conversation — you’re not following up, you’re chasing. And chasing feels uncomfortable because it is. You haven’t earned the right to the next conversation. You just assumed it.

Build the next step into every meeting. The follow up problem disappears.

4. People price on fear, not value.

I watched hundreds of business owners discount before the client even asked.

They’d quote a number. Feel uncomfortable with the silence. Then immediately offer a lower price or add more scope.

The client hadn’t said a word.

Fear of rejection drives more margin destruction than any competitor ever will. Pricing is a structure problem. Not a confidence problem. When you can articulate value clearly — the number holds.

5. Everyone wants a shortcut. Nobody wants a system.

The hardest thing I dealt with as a teacher was this:

People would come in looking for a tactic. A script. A hack. Something that would make sales feel easier without changing how they operated.

The ones who got results were the ones who accepted that sales is a system — not a skill you turn on and off. They installed the structure. They ran the process. They stopped improvising.

The ones still looking for shortcuts are still struggling.

6. The biggest revenue leak is not losing deals. It’s not following through on won ones.

I saw this constantly in agency businesses.

A client signs. Everyone celebrates. Then delivery starts and the account goes quiet. No structured check-in. No expansion conversation. No one asking “what else do you need.”

The client doesn’t renew.

And the business goes back to hunting for the next new logo.

Retention is a sales function. Most businesses don’t treat it like one.

7. The operator who can’t get out of their own sales process is the ceiling.

This one is the hardest truth.

In enterprise I’ve seen it in sales directors who can’t delegate deals. In small business I’ve seen it in founders who are the only person who can close.

The business cannot scale past the individual.

The fix is never “work harder.” The fix is always structure. A system that works without you in every conversation. A team that knows what to do without asking. A process that runs whether you’re in the room or not.

8. Selling is a spiritual game.

I learned this from Tony Robbins. And it took me years to fully understand what it meant.

It doesn’t mean prayer before a sales call.

It means this — the moment you walk into a conversation needing the sale more than the client needs the solution, you’ve already lost. The client feels it. Every human does. Desperation has a frequency.

The best salespeople I’ve ever worked with had one thing in common. They were genuinely detached from the outcome. Not because they didn’t care. But because they believed completely in what they were offering and trusted the process to deliver the result.

That’s the spiritual game.

It’s not about mindset posters or morning affirmations.

It’s about doing the inner work to show up without neediness. To serve the client’s problem — not your own pipeline.

Structure gets you to the room.

This gets you the deal.

9. The deal size you close is determined by the identity you carry.

This one is uncomfortable. Most people don’t want to hear it.

But after 1,300 conversations it became impossible to ignore.

The professionals who struggled to close large deals — not because of skill, not because of process, not because of competition — but because somewhere deep down they didn’t believe they were worth sitting across the table from someone writing a seven figure cheque.

They’d get to the final stage. Everything was aligned. The client was ready.

And then they’d discount. Or over-explain. Or go quiet. Or find a reason the deal wasn’t quite ready to close.

It wasn’t a sales problem.

It was an identity problem.

Your personal sense of worth becomes your commercial ceiling.

I’ve watched $50,000 per year salespeople become $500,000 per year closers — not because they learned new techniques but because they did the inner work to believe they belonged at that level.

The structure and the system matter enormously. I’ve built my entire body of work around that belief.

But no system in the world will get you across the line if you don’t believe you deserve to be there.

The million dollar deal starts with the million dollar identity.

— Jag