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Stop Winging It: How To Improve Your Sales Conversations

Over the last few articles in this four-part sales series, I’ve talked about why sales feels uncomfortable for so many advisers, what’s happening psychologically for clients during the decision-making process, and some practical ways to make sales conversations feel more natural and effective.

But I want to finish with something that ties it all together.

Because the biggest mistake advisers make with sales is expecting themselves to just be good at it – without ever practising.

The link between sales and professional athletes

Think about professional athletes for a second. They don’t just show up on game day and hope for the best.

They train, they practise, they review. Then they improve one thing at a time.

Sales is no different.

But most advisers approach it completely differently.

They have the meeting.
Feel like parts of it were awkward.
Replay it in their head on the drive home.
Then move on to the next one.

No practice, no review, and no intentional improvement.

And because of that, every sales conversation keeps feeling emotionally loaded.

One good meeting gives them confidence, but one awkward meeting knocks it again.

That’s exhausting.

The advisers who look calm and natural in sales conversations usually aren’t naturally gifted communicators. They’ve simply had more reps. They’ve spent time improving the skill instead of just hoping confidence would eventually arrive.

Because confidence doesn’t magically appear.

Repetition comes first.

Sales is a skill – not a personality trait

A lot of advisers still think sales ability is something you either “have” or you don’t.

But my story proves that’s not the case.

When I first started my financial planning business, I was naturally good at marketing – but sales was a challenge.

I’d spend all this time bringing in leads, only to hear the same thing in meetings over and over again: “I’ll think about it.”

It was incredibly frustrating. At one point, I nearly gave up.

But deep down, I knew I could help these people, so I put my big girl pants on and took ownership. I started working on sales the same way I worked on other things I wanted to improve – and that’s when my meetings started to change.

The lesson? Sales is a skill, which means it can be trained.

And like any skill, improvement comes from deliberate practice – not just experience.

There’s a huge difference between repeating the same meeting 100 times and actually getting better at it.

If you want your sales conversations to improve, you need a process.

Not a perfect script, not a different personality – just a process for improving on purpose.

The habit that changes everything

Here’s the simplest way to think about it.

Train.
Play.
Review.
Improve.

That’s it.

1. Train

Before the meeting, practise the parts you find hardest.

Not the whole conversation – just the bits that make you uncomfortable.

Opening the meeting.
Explaining your process.
Talking about ongoing fees.
Sitting in silence after asking a big question.

You can practise with a colleague, with a coach, or honestly, even with ChatGPT.

The point is to stop making real client meetings the only place you ever rehearse.

2. Play

Then have the meeting.

Stay present.
Don’t try to sound perfect.
Don’t try to “perform”.

Just focus on the conversation.

One thing I see advisers do all the time is put massive pressure on themselves to get everything exactly right. But clients aren’t looking for perfection. They’re looking for clarity, confidence and connection.

And ironically, trying too hard is often what makes the conversation feel awkward.

3. Review

This is the bit almost nobody does properly.

After the meeting – ideally straight after – do a quick review.

Not a 45-minute analysis.
Five minutes is enough.

Ask yourself:

What worked?
What felt awkward?
What would I do differently next time?

That’s where improvement starts.

One of the biggest advantages advisers have now is access to technology that can help you review your sales conversations far more objectively and efficiently than ever before.

One thing I’d recommend is using meeting transcripts from programs such as Claras as part of your review process. You can press the PII button so all the personal information is removed, then upload the transcript into ChatGPT and ask it to review the conversation.

It can help identify things you may not notice yourself – where you interrupted too quickly, missed a buying signal or failed to ask a better follow-up question.

Reviewing properly turns experience into improvement.

Improve one thing at a time

This is where most people go wrong.

They try to fix everything at once.

Athletes don’t do that – they focus on one thing, then practise it repeatedly until it becomes natural.

Sales works exactly the same way.

So instead of trying to overhaul your whole process overnight, pick one thing for your next meeting.

Pause longer after asking questions.
Explain fees more clearly.
Talk less.

Ask one better follow-up question.
Slow the conversation down.

That’s how confidence gets built.

The advisers who become great at sales conversations usually aren’t the smoothest or most polished people in the room.

They’re the ones who stopped winging it.

P.S. Want more tips for scaling your business? Book your free Scale Session, follow me on LinkedIn or join my Scale Squad.