27 Training Ideas To Start Closing 5-Figure Deals

27 Training Ideas

Table of Contents

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Hi all,

Web 3 Feb

Here’s the time today.

Yup ridiculously late start.

This morning I woke up late (9.30….5 hours late!) and jumped immediately onto a sales call with my head of business development Ion.

That got me thinking about the nature of sales training in general as it’s something that’s a big part of Ion’s day now as he works with the rest of the team.

And so I thought I’d share some of my insights into improving your ability to close deals through using following sales training ideas for meetings:

Elevator Pitch Training

Elevator Pitch Training

So one of the most important aspects of any pitch you make is your ability to fashion and deliver an effective elevator pitch.

That is describing – with clarity and ‘bounce’ (i.e energy) – what value is it the product or service you’re selling gives.

In the case of this blog – if I was ‘selling’ someone on the idea of subscribing to the blog than my pitch might be –

‘My blog is your go-to resource to get real-world insights into matters relating to personal development and entrepreneurship delivered in such a detailed manner – that it’s unlike any ‘similar’ blog – that’s typically ghostwritten and not ‘in-the-weeds’ enough to drive true value you need’


I guess that’s not bad. 

But – this is ONE part of the journey

The other part of it is actually delivering this elevator pitch.

Tonality, speed, emphasis…bodily expression – all of it comes into play when trying to build a solid elevator pitch.

Cold Calling Intro Training

Cold calling

What about taking an elevator pitch and wrapping it into a strong intro? One of the biggest challenges you’ll face when pitching is having a strong intro.

How do you effectively deal with ‘who’s calling?’ or ‘what do you want?’

Lol – there’s going to be many sales people that will argue endlessly over the best way to approach this – but regardless – 

Having a strong intro up your sleeve is definitely going to be important to your success.

Again – it’s about being able to deliver a strong intro no matter what type of person you get in front of you

Scenario Planning 

 Scenario Planning

When thinking about sales training ideas whether it’s inside sales training ideas, retail sales or any types of sales training – one of the areas commonly overlooked is scenario planning.

This is about mapping out all of the potential situations you could find yourself in – and mapping out appropriate responses for each of these situations.

The question I have is – how many of us actually do that?

The answer is probably very few of us.

So with this in mind – try and practice various scenarios which include (but are not limited to) – 

  • Getting past a gatekeeper 
  • Dealing with budget issues
  • Talking to an non-decision maker
  • Needs time to ‘think about it’

As you start to map out the various scenarios you can build responses for each engagement, you’ll then well…

Be prepared for anything.

Scenario planning of course – leads me onto my next area of focus for sales training which is:

Objection Handling

Objection Handling

This section would be worthy of an entire book all by itself – and rightfully so – because of the multifaceted nature of objections and what format they come in.

Some of the scenarios we pointed to above make up objections, and there are going to be many more besides – so running your team through the gauntlet of ‘objections’ that could be thrown at them is an excellent way to get better at the ‘sale’.

Objections – in truth – don’t change that much from company to company or product to product.

If you were to ask Jordan Belfort lol (or read his book at least ‘The Straight Line Theory’) – you’d learn from him there REALLY there are only a couple types of objections that people use.

They’re all just variations centred around the same types of objections.

This can be around ‘budget’, ‘timing’, trust and any other time constraints

Best Books For Sales Training

Sales Training Books

This is an important one in my mind that you must encourage your salespeople to engage in – and that’s self education. 

It’s silly to think that your training is going to be the most complete out there – and that there’s no value in them drawing in tips and techniques from other sales literature that’s out there.

Some might disagree with this – but I think the more sources they can draw from to then practice with – the better!

Best Videos For Sales Training

Sales Training Videos

This is similar to the above – but this time we’re talking videos – i.e identifying videos that are well worth watching because of the live sales examples they provide as well as all they demonstrate that you can’t get through the written word –

Which I’ll go on to underline now:

Tonality In Sales Training


Again this one comes from Jordan Belfort – and it’s something that many many sales people don’t think about.

It’s a simple thing that separates the good sales people from the great salespeople – and ultimately boils down to not WHAT people say – but fundamentally the WAY you say something.

It’s incredible how much of a difference this can make.

I’m thankful that I’ve got a partner whose Italian in Strawberry – so this has been nailed into me – the importance of tone that is.

It’s also a big part of my family, being the youngest of 5 – tone got you heard amongst the noise.

With 93% of communication being non-verbal – I’d also include tone in this bucket – and I’ve got a whole blog post dedicated to tonality which I urge you to check out

A Power Hour Of Cold Calling

Cold Call

This is something I’m going to write about separately I think – but the power of the power hour is a big one.

This is where you can dedicate a full 60-minutes to one task at the expense of everything else.

The value this extreme focus brings is also extreme success.

There’s lots of value in just getting your head down and focussing on dialing as a way to practice and learn extremely quick – i.e throwing your sales team to the wolves.

After everything is said and done – I’d rate this as being amongst the most effective ways to make things happen and to learn fast

Selling Through Curiosity Training

Curiosity Training

This is knowing, fundamentally what questions to ask to uncover your prospects hopes, fears and dreams.

It’s of course a little challenging to uncover this when you’re dealing with a large organisation but this is definitely a good one to practice.

It’s not dissimilar to the Socratic method where you guide someone via questions to uncover the real reasons for their intended purchase.

Now, this will differ when you’re talking to a business owner Versus talking to a business development manager or someone else working i n procurement.

I.e the motives for someone who’s looking for a vendor for their company versus the motivation decision maker are very different – so it’s important to be mindful of this

Developing Your Industry Knowledge 

Industry Knowledge

You’re oftentime going to be talking to people who have a decent degree of industry knowledge – and so being able to weave industry knowledge neatly into your pitch is going to be critical.

This is ultimately a slow and ongoing process – but you can begin with making sure some industry fundamentals are familiar to you – else you’ll fall apart in front of someone who keeps up with industry news.

This in turn ties in with:

Product Knowledge

Product Knowledge

Much the same as above – know what the product you’re selling does – so you can practice and play games based around testing your sales reps based around knowledge of the product.

All of its features and components and what they actually mean – which in turn (and this should also be practiced) will give them:

Understanding Of How To Apply The Product As A Solution To A Prospect’s Problems


Depending upon the complexity of the product (e.g we sell SEO as well as B2B Lead Generation – with Lead Gen this is simpler as compared to SEO) – you want to be able to weave in a particular product feature of use case as being the ideal solution for your prospect.

Practice Building Instant Rapport With Your Prospect

Practice building

This is definitely something one some of my sales team have struggled with – being unable to build rapport instantly with a prospect.

This can be for all manner of reasons – but it’s important to practice this by having someone ‘play’ a variety of different people based upon the types of prospects you get onto calls with.

The quicker your team can build rapport with someone – the more likely the sales call is going to go well.

Talking of calls:

Being ‘Zoom’ Ready For Your Video Sales Calls

Zoom Calls

Even before Covid – Pearl Lemon were 100% remote – and this means you need to think about some particular details such as:

  • The frame of the video?
  • Are you in the centre of the video?
  • What are you wearing?
  • What’s in the background?
  • Is there any background noise?
  • Do you have a place to be ‘lively and animated?’

Making sure all of these things are nailed is important to the success of your sales process. I’m not sure this is an idea – but more of something that needs to be in place

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Practice Making Best Use Of All Your Sales Materials

Sales Materials

So, at Pearl Lemon, we have lots of different material the sales team can call upon – in terms of slide decks, visuals and technical documentation – and it’s important that your sales team make use of these.

Understanding when and when not to use them is an important part of training also.

We’ve won some clients solely because they’ve seen some of the technical literature we’ve put together and decided that we’re the team for them.

Others want to see some glossy slides – so it always varies. 

And knowing who needs what is important to the success of a sales call

Improve Your Active Listening Skills

Listening Skills

Prospects say….a lot.

Even when they don’t say a lot – so being able to hear what they’re talking about – as well as what they’re NOT talking about is powerfully listening.

In this way you can begin to pick up vital clues that will feed into your pitch as well as any questions you want to ask.

So making sure you’re able to catch all of the details in a conversation to draw upon in that same conversation or later is important.

And there are always details, as well as amusing comments you can refer back to

Asking The Right Questions

Right question

Within each company, as well as within sales in general – there are some pieces of information you want to walk away with from every conversation.

This is answers such as:

  • Budget?
  • Timeline?
  • How many people are we competing against?
  • What would help us win this project?
  • Any ‘no-no’s’/pet peeves?

These are just a smattering of general questions you want the answers to in order to progress a sales conversation.

And talking of this:

Organising The Follow Up On The Same Call

Follow up

Never leave a sales conversation without a next action.

What could be an important next step to progress the conversation?

What else is needed to progress the call closer towards the sale?

This should always end with

  • Organising a followup call with the prospect + a decision maker OR
  • Organising a follow up to discuss the proposal you send across

So making sure whatever the scenario is – you make these things happen

Practicing Email Sales

Practicing Email Sales

This is something that is often overlooked – but how do reps send emails?

Do they answer all the questions from the prospect? 

(Even the hidden/inferred questions?)

What case studies and due diligence are they sending?

What about the style and tone of the email?

Are there any obvious howlers?

Practicing How To Leave Voice Notes And Voicemails


This is one that isn’t worked upon enough at all.

Much of our business dialogue is now happening over Whatsapp – and this comes with leaving prospects messages via Whatsapp (really high response rates) – as well to a lesser degree – voicemails.

So practicing the art of leaving a fun and informative whatsapp message is a great way to make an introduction or follow up.

Bonus tip: We do this with Skype and LinkedIn as well 🙂

Making Room For Your Teams Individual Strengths

Teams Individual Strengths

No two sales people sell exactly the same. 

Recognising this is important when developing your team.

Some reps are a lot more technically led, others focus upon rapport build, some are aggressive closers, others take a more casual approach (red flag lol).

But recognising the advantages of each sales rep, as well as weaknesses – and allowing them room to work based upon these variations is important – but equally:

Using A Sales Reps Individual Traits Are Key Selling Points

Sales reps

Is something that is not considered enough. My head of sales always uses him being Greek or being based in Barcelona as means to incite and bring in humour into a conversation.

So identifying individual traits within each of your sales team and seeing how this can be weaved into the narrative is important.

I’m British Indian so I often use the two to talk about Indian work ethic with British standards.

What can your team use?

Having Sales Mentors and Buddies

Sales Mentors and Buddies

Teaming people up so they can work together, or having a more experienced person mentor a less experienced person are both also key.

My head of sales has been in sales for 14 years and comes from a background of hard cold-calling.

He’s the most experienced person on the team and is able to offer insights and advice to the 22, 27 and 34 year old sales reps who’ve had much less experience than him – insights they wouldn’t ordinarily get

And it gives my head of sales the opportunity to sharpen his sword – so developing buddies and mentorship is a great way to bring up the general standard.

Pitch Practice

Pitch Practice

Intense but practical – this is literally doing pitches back to back and listening correcting and improving based upon hearing how people pitch.

It’s a hard and fast way to improve your own sales pitch.

Engage In Role Play

Engage In Role Play

This feeds off of the last point – that when you engage in pitch practice – you’re also engaging in role play.

So working through the different types of sales situations you come across and switching roles based upon the person and prospect is a good way to work through challenges

Listen To Call Recordings

Listen To Call Recordings

If you’re not recording your calls (we record 1 in 4 calls – particularly the ones on video) – then you’re missing out.

It’s an excellent way to analyse a sales call and identify points for improvement.

I did a sales call with my head of sales and he highlighted that I missed out on a couple of key things which I didn’t realise at all which were:

  • Understanding who else was involved in the decision
  • Not pushing fast enough to get closer to the sale
  • Booking the next call too far out (i.e 6 days later)

We also recorded the call – and getting that quality of instant feedback is excellent – as it demonstrates key areas for improvements

Buddy Up On Calls

Buddy up on calls

Much like what I just described in the point above – why not do calls together from time to time?

One of the things we’ve begun to institute is doing calls together every so often.

It’s a great way to get instant feedback and to learn from each other’s pitches.

There are always techniques and strategies that other people in your sales team use – that you perhaps don’t – and this can come out and be learned from when you buddy up!

Final Thoughts

Final thoughts

I’m not sure I have any haha.

But no seriously, there are (I’ve just done the count) – 27 ideas (and there are definitely still more) to help raise the level and skill of your sales team.

In our office we’ve pretty much done over 20 of these – possibly all of them – and I can definitely vouch for their effectiveness in building – in what I have – a small sales team of 4 people excluding myself.

So – I hope this helps you on your journey to building a really solid sales team 🙂