How to Help Your Sales Team Get Better at Conversations

You can’t just tell your sales team to “get better at conversations.”

You can’t run a workshop, fire off a few call recordings, and hope things change.

Because salespeople don’t learn by being told. They learn by doing.

If you’re in sales enablement or lead a team, this is probably obvious. What’s less obvious is how to get them doing the right things, in the right way, often enough to make a difference.

At Skylar, we’ve worked with over a hundred sales teams. And we’ve found that the ones who truly improve at conversations — the ones who start sounding more confident, more consultative, more natural — all follow the same simple framework.

It’s not a magic formula. It’s just these three steps, done right:

1. Show them what good looks like — and make them believe it

First, your team needs content.

Something to learn from. It could be a call recording, a talk from a top rep, a quick demo, or even a few slides.

But here’s the thing: it’s not enough to tell them what good looks like. They have to trust that it’s actually good.

Reps are sharp. They’ve seen a lot. And they can smell fluff from a mile away.

So if the example feels too polished… or too generic… or too far from real life — they’ll tune out. Even if it’s technically “right.”

What works is showing something real and relevant. Something they could see themselves saying. Something that makes them go, “Oh… that would actually work.”

When that happens, it clicks.

Now they’re not just watching a training. They’re seeing a better version of themselves — and believing it’s possible.

That’s when learning starts.

2. Make it easy

Salespeople are busy. Busy selling. Busy updating Salesforce. Busy replying to things that feel more urgent than your training session.

So whatever you want them to do next — it has to be easy.

No long pre-work. No multi-step sign-ins. No “find a partner and role-play this by Friday.”

This is where a lot of programs break down. They have great content — and no adoption. Because the path from “I saw this” to “I tried this” is full of tiny blockers.

3. Let them practice it — the right way

This is where most teams fall short. You can’t expect reps to become proficient at something new if they have just heard it once.

They either ask reps to practice with each other — which sounds nice in theory, but almost never happens in real life. No one wants to block time, break the ice, and give each other fake objections. It’s awkward.

Or, more often, they just practice live on calls.

They try a new phrase, or a new opener, with a real buyer. But they don’t do it very often. It’s risky. And it kills deals when it goes wrong.

At Skylar, we built a third path: Practice with AI.

Your reps talk to an AI buyer, in a safe space, with zero stakes. They try new talk tracks. Handle objections. Test ideas. And they get feedback — instantly — on how to get better.

It’s fast. It’s private. And it works.

The real work is building habits

The truth is, no one gets better at sales in a day.

You can have the best workshop, the best content, the best coaches — and still, most of it will fade in a week unless reps have a way to try, repeat, and improve.

That’s why this framework matters.