10 Steps to Turn Fresh Reps Into Confident Cold Callers

cold calling confidence

How do you take somebody with no cold calling experience whatsoever, to being a fully competent and confident prospecting superstar?

Sadly, I still see many companies who lack any form of structure or process, in training their sales reps in becoming effective at utilising the phone.

The act of giving somebody a handset, a list of contacts, and the instruction to ‘start dialling’, is still prevalent and hopeful (at best) strategy. Its lazy, and is ultimately just setting reps up for failure.

Here Rich and Connor dive deeper into these 10 steps:


1. 1-2-1 Mindset/mentality session

Cold calling is really hard. It requires bravery, resilience, and mental toughness. Cold call reluctance as a result, is still prevalent across many sales teams where reps are anxious and fearful of picking up the phone. They get nervous about rejection or feel awkward being an interruption.

Therefore, it’s imperative that before I start training somebody at cold calling, I discuss the importance of having the right mindset and uncovering the hidden mental barriers which will hold the person back.

Acknowledging the realities of this with the salesperson up front, will show that you understand their concerns and get them to realise you are on their level. It also enables you to discuss and agree on strategies for dealing with rejection ahead of time, rather than after the fact, when it can often be too late.

2. Whiteboard session call structure, scripts, and objections

There’s nothing quite like getting a marker pen in your hand, and painting a process out on a whiteboard. It just feels like you’re being creative, not to mention the obvious benefits for more visual learners.

Whiteboarding enables you to take sales people through a step-by-step class in an interactive fashion, more engaging than just running through a slide deck. It helps them appreciate sales calls as a process and workflow, and something which can become repeatable.

It enables them to better understand the pitfalls and likely moments of calls where objections are going to pop up. It helps them figure out most likely moments where they need to try and close prospects or qualify out.

It’s the theory before the practice.

3. Listen to call recordings of the good, the bad, and the ugly…

I predict that any sales person will learn more about how to cold call by listening to real sales call recordings for an entire day, than if they were to sit in a classroom listening to a trainer preach for a week.

There's no more impactful way of helping sales people get familiarised with what real sales calls sound like than giving them access to best practice conversations that end in booked appointments.

But critically, its important they hear the calls that don’t go so well, so that they gain an appreciation that its not all happy, smiley conversations.

It brings some reality to the theory, and moreover - listening to libraries of recorded calls one after another is immensely more productive than live call shadowing.

4. Rapid fire objection handling role-play

You’ve drawn out your list of objections on the whiteboard and talked around ways to handle them, now let’s get the sales people practising them. Best way for doing this shouting out an objection from your whiteboard, and getting the sales person to say their response.

Try mixing up the objections, whilst re-visiting the same ones again and again. This starts to build the crucial muscle memory which sets the top reps out from the rest.

I’ve found doing this in the office in front of the rest of the sales team also has the added benefit of getting them comfortable of ‘selling’ in front of their peers.


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5. Use Refract to record sales call role-play openings.

Practice makes perfect. This is no more true in sales than it is when perfecting your craft in sport or playing an instrument. Effective role-play is crucial to helping green sales reps get ‘game-ready’, whilst building their confidence in the process.

Practice the first 30-60 seconds of the sales call rather than the entire conversation. Breaking it up into bite-sized chunks helps reps learn in a more manageable format, and doesn’t overwhelm them.

The problem with role-play is that traditionally, it’s been carried out in false environments and settings. If you are practising role-play cold calls, then practice on the phone. Doing this face-to-face is false and unnatural.

Even better, record these calls through products like Refract, so you get the benefits of post-call review and feedback. Reps get to hear HOW they sounded, and more times than not, can self-diagnose the areas where they could have improved. Their learning curve just got that much quicker.

6. Set scenario challenges to practice value propositions

Understanding and relaying your company’s value proposition(s) is possibly one of the most crucial parts of a sales person’s sales call, yet despite this, most sales reps struggle to deliver this in an impactful way.

They resort to feature bashing or confusing prospects with jargon or complicated language. They need this to sound crisp, to the point, and aligned with the problems you solve for your ICP.

I’m gonna sound like a broken record here, but the only way to improving here, is to practice. I’ve found setting video based scenario challenges to sales reps, getting them to practice delivering the value proposition again and again, is the route to building that all important muscle memory.

This also gives them a safe place to practice versus messing up with real valuable prospects.

7. Listen to best-practice call recordings from the playbook

After practice, comes call listening. Mixing in the practical activities with the power of hearing actual sales calls, just delivers that further reinforcement and transparency, which new sales reps need in order to get comfortable before they get on the phone themselves.

I’ve also learned that for the right type of coachable sales person, they really crave and enjoy listening to the ‘game-tape’.

At this stage of the learning journey, giving them access and exposure to the best in class conversations, will give them the appreciation of what ‘good sounds like’, and massively increase the chances of them replicating this when they start to speak with prospects.

8. Call velocity shadowing session

Whilst call shadowing is a time inefficient process for getting reps listening to sales conversations, there is one unspoken huge benefit of getting reps to observe you making calls live. Whilst quality of conversation is still King in sales, achieving the right level of activity to generate quality conversations is still crucial.

Getting inexperienced sales people to simply observe the process and importance of rattling through calls at pace, and clocking up the dials gives a more rounded appreciation of what’s. expected of them to achieve the right results.

Lead from the front and set the benchmark, while sharpening your own prospecting skills in the process. What’s not to love?!

9. Use Refract to record role-play calls end-to-end

Like a jigsaw, it’s time to put all the pieces together and start practising sales calls from start to finish. Again, recording these in products like Refract, enables you to do rapid post-call debrief sessions, whilst encouraging reps to self-diagnose and critique.

Try a variety of call types, with some more trickier than others, mixing in different objections and call outcomes. One off-shoot benefit of capturing all of these practice call recordings, is they also become great learning material for future fresh sales reps.

10. Make real calls and capture recordings for feedback

Now is the time to put all of the learnings and rehearsal into practice. Setup ‘power-hours’ initially to get reps to start making calls to real prospects. Observe how they conduct themselves and how comfortable they are at making dials.

Sit close to them so they feel they have your support, but don’t breathe down their necks so they feel under pressure.

Again, use platforms like Refract to review conversations as they happen and deliver real-time feedback back to reps, so they can quickly fix mistakes ahead of their next conversation.

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