sales – James White

The Very Best Salespeople Practise Hard (And Why Preparation Beats Talent Every Time)

James White — Sat, 18 Jul 2026 11:07:09 +0000

Executive Summary

Many salespeople believe confidence comes naturally to top performers. It doesn’t.

Just as professional golfers spend countless hours preparing before The Open Championship, the best salespeople rehearse the conversations, questions and objections they’ll face long before they sit in front of a prospect.

In this article you’ll learn:

What Can Salespeople Learn From The Open Championship?

Every July, millions of people watch The Open Championship.

We admire the incredible approach shots, pressure putts and dramatic finishes. We celebrate the winner lifting the famous Claret Jug.

What we rarely see is what made those moments possible.
The early mornings.
The hundreds of balls struck on the practice range.
The countless hours spent working on putting, bunker play and course management.
Recently I watched Rory McIlroy preparing for The Open. He wasn’t competing. He was preparing.

It reminded me of something I see repeatedly in sales.
The very best performers don’t simply turn up hoping to have a good day.

They rehearse.

They prepare.

They practise.

Professional golfers understand something many salespeople forget:

Confidence is built long before performance begins.

Why most discovery calls fails (and how I run mine)

Why Do Most Salespeople Underperform Under Pressure?

Unfortunately, many salespeople treat live customer conversations as practice sessions.
They spend hours preparing proposals.
Very little time preparing themselves.
The first time they deliver a new introduction is during a real sales meeting.
The first time they ask a difficult discovery question is with an actual prospect.
The first time they deal with an objection…
…is when somebody objects.
Imagine if Rory McIlroy’s first drive of tournament week happened on the first tee on Thursday morning.
It would be unthinkable.
Yet many salespeople do exactly that every single week.

Why MSP Prospects Don’t Buy (And Why You Usually Discover It Too Late)

What Should Salespeople Practise?

From coaching hundreds of sales professionals, I’ve found four areas consistently separate top performers from everyone else.

1. Practise Your Opening

Your opening isn’t about explaining what your company does. It’s about giving your prospect a reason to keep listening.

Can you explain—in under a minute—why your organisation matters?

Not your services.
Not your certifications.
Not your technology.

Why should your prospect care?

2. Practise Your Discovery Questions

Great discovery isn’t improvised.
The strongest questions have already been thought about.
Refined.
Tested.
Practised.
The better your questions, the more valuable information you’ll uncover—and the more relevant your recommendations become.

3. Practise Handling Objections

Every MSP hears the same objections.

“We’re happy with our current provider.”
“We’ve got no budget.”
“Can you send me some information?”

None of these should ever catch you by surprise.
If you hear them regularly, your response should already have been rehearsed dozens of times.
Preparation allows you to remain calm instead of becoming defensive or reactive.

4. Practise Asking For Commitment

This is where many opportunities stall.

The meeting has gone well.

The prospect is engaged.

Everyone appears positive.

Then the salesperson finishes with:

“Let me know what you think.”

Instead, practise confidently asking for the next step.

Whether that’s arranging a technical workshop, introducing decision-makers or booking another meeting, progressing opportunities requires deliberate practice.

Why most discovery calls fails (and how I run mine)

Does Practice Really Build Confidence?

One of the most common things I hear is:

“I wish I was more confident.”

Confidence is rarely the starting point.

Preparation is.

The golfers competing at The Open don’t suddenly become confident standing on the first tee.

Their confidence comes from knowing they’ve already hit that shot hundreds—if not thousands—of times before.

Sales works exactly the same way.

You won’t rise to the pressure of an important sales meeting.

You’ll fall back on the preparation you’ve already done.

How Can MSP Salespeople Improve Quickly?

You don’t need to spend six hours a day practising.

Even thirty minutes each week can dramatically improve your performance.

Role-play objection handling with a colleague.

Record yourself delivering your introduction.

Review your discovery questions before every meeting.

Practise asking for commitment until it feels natural.

Small improvements made consistently create a significant advantage over time.

The Value Gap: Why Prospects Think You’re Too Expensive

Final Thoughts

There are no shortcuts to becoming exceptional in sales.

The best salespeople don’t simply work harder.

They prepare harder.

So before your next prospect meeting, ask yourself one question:

3. Practise Handling Objections

Because when pressure arrives—and it always does—you won’t perform at the level of your ambition.

You’ll perform at the level of your preparation.

Frequently Asked Questions

Does practising sales really make that much difference?

Yes. Practising common sales scenarios allows you to communicate more naturally, ask better questions and respond confidently when objections arise.

What should I practise first?

Start with your opening, your discovery questions, common objections and how you’ll ask for the next step. These four areas have the biggest impact on sales performance.

How often should salespeople practise?

Like any professional skill, little and often works best. Even 20–30 minutes each week can significantly improve confidence and consistency.

Is role-playing worthwhile?

Absolutely. Role-playing allows you to test different approaches in a safe environment before using them with real prospects.

Let’s Talk After the Summer? Why MSP Prospects Delay Buying Decisions

James White — Sat, 11 Jul 2026 08:35:08 +0000

Executive Summary

Every summer, MSP salespeople hear the same response:

“Let’s pick this up after the holidays.”

It’s tempting to assume annual leave has killed the opportunity.
In reality, holidays are rarely the reason deals stall.
More often than not, prospects delay because they don’t yet feel enough urgency to act. If the business problem was significant enough, they would find the time before they went away.

In this article you’ll learn:

Every Summer, MSP Sales Pipelines Slow Down

July and August can be frustrating months for managed service providers.

Decision-makers disappear on holiday.

Projects pause.

Meetings get postponed.

Pipelines appear to grind to a halt.

After more than 30 years in B2B sales, I’ve noticed something interesting.

The businesses that continue winning work throughout the summer aren’t necessarily selling better services.

They're simply uncovering urgency better than everyone else.

Because holidays rarely stop people buying.
They simply expose a lack of urgency that was already there.

Why Do Prospects Say "Let's Talk After the Summer"?

This is one of the most common questions I hear from MSP sales teams.

Typically, the conversation has gone well.

An IT Director says they’re reviewing suppliers.

A Managing Director admits they’re unhappy with support.

Someone downloads your cybersecurity guide.

Discovery goes well.

Everyone seems positive.
Then comes the familiar response:

“Let’s revisit this after the holidays.”

Many salespeople immediately blame timing.

I think that’s the wrong conclusion.

Instead, ask yourself:

If ransomware hit their business tomorrow, would they still wait until September?

Probably not.
Urgency nearly always beats inconvenience.

Why MSP Prospects Don’t Buy (And Why You Usually Discover It Too Late)

How Can MSP Salespeople Create Urgency Without Being Pushy?

One of the biggest misconceptions in sales is that urgency comes from pressure.

It doesn’t.

Pressure comes from the salesperson.

Urgency comes from the prospect recognising the cost of doing nothing.

Those are two very different things.

Good salespeople don’t invent urgency.
They help prospects discover it for themselves.

Why Prospects Don’t Buy: The 6 Hidden Reasons MSP Deals Stall

Help Prospects Visualise Life After the Decision

Rather than pushing harder, help them picture the benefits of making the decision before they leave.

Questions like these work well:

People naturally like clearing their desk before going away.
You’re simply helping them remove one more item from the list.

Read about The Value Gap

Why Discounting Is Usually the Wrong Answer

Every summer I see MSPs making the same mistake.
They panic.
Then they discount.

Perhaps it’s:

Please don’t.

The moment you reduce your price simply because it’s July or August, you’re telling the prospect your pricing wasn’t fixed in the first place.

That’s incredibly difficult to recover from.
Instead…
Increase value.

What Can MSPs Offer Instead of Discounts?

Value-added offers reinforce your expertise without reducing profitability.

For example:

Instead of Discounting	Add Value Instead
Reduced onboarding fee	Priority onboarding before September
Lower monthly support	Complimentary Microsoft 365 security assessment
Discounted project work	Cyber Essentials readiness review
Reduced consultancy	Staff cybersecurity awareness training

The investment stays the same.

The perceived value increases.

Everybody wins.

Sometimes the Best Close Is Simply Being Honest

If you’ve built trust throughout the sales process, sometimes honesty is the strongest close available.

You might say:

“I’d genuinely love to help solve this. If we can get everything agreed before you go away, we’ll spend August preparing everything so you’re ready to hit the ground running when everyone returns. How does that sound?”

No pressure.
No manipulation.
Just a genuine desire to help.
Surprisingly often, that’s exactly what prospects need to hear.

My Experience Working with MSP Sales Teams

Across hundreds of sales conversations I’ve reviewed with MSPs, I rarely see deals lost because someone went on holiday.
Instead, opportunities usually stall because discovery didn’t uncover enough business impact.

The prospect liked the salesperson.
They liked the company.
They even liked the proposal.
They simply didn’t believe solving the problem today was significantly better than solving it in six weeks’ time.

That’s a discovery issue.
Not a holiday issue.

Why Most Discovery Calls Fail (And How I Run Mine)

One Final Thought

Don’t confuse timing with urgency.
Prospects don’t delay because it’s summer.
They delay because the pain of staying where they are still feels smaller than the effort of making a decision today.

Your role isn’t to create pressure.
Your role is to help them recognise the cost of waiting.
When you do that well, summer becomes far less of an obstacle than most MSP salespeople believe.

Why Most Discovery Calls Fail (And How I Run Mine)

Diary of an IT Sales Expert Podcast – How I Manage Long Sales Cycles

Frequently Asked Questions

Why do MSP deals slow down during the summer?

Holiday periods can delay meetings, but they rarely stop important buying decisions. Businesses still make decisions when the need is urgent enough.

Should I discount my MSP services to close deals before the holidays?

Generally, no. Discounting weakens your value proposition. It’s usually more effective to offer additional services or implementation benefits instead.

How do I create urgency without pressuring prospects?

Focus on helping prospects understand the consequences of delaying their decision rather than trying to force them into making one.

What questions help uncover urgency?

Questions that explore business impact work well, such as:

What happens if nothing changes?
What’s the cost of waiting until September?
How would your business benefit if this was already underway?

Why do prospects delay decisions?

Most delays happen because the perceived cost of staying the same is still lower than the perceived effort or risk of changing.

Why MSP Prospects Don’t Buy (And Why You Usually Discover It Too Late)

James White — Sat, 27 Jun 2026 09:27:09 +0000

Executive Summary

If you’ve ever delivered what felt like the perfect proposal, only to hear “We’ve decided to stick with our current provider” or “We need to think about it,” you’re not alone.

Most MSP sales aren’t lost because your price was too high or your proposal wasn’t compelling enough.

They’re lost because concerns that existed throughout the buying journey were never uncovered during discovery.

In this article, you’ll learn:

The five hidden reasons MSP prospects don’t buy.
Why objections rarely appear at the end of the sales process.
The discovery questions that uncover concerns before they become deal killers.
How the best MSP salespeople prevent objections instead of trying to overcome them.

They Don't Stop Buying At The End. They Stop Buying Much Earlier.

Every MSP owner has experienced it.
The discovery meeting felt positive.
The chemistry was good.
The proposal reflected everything the prospect asked for.
You leave the meeting convinced you’re about to win another managed services contract.
Then…

Nothing.

The follow-up email gets a polite response.
“We’re still discussing internally.”

A week later:
“We’ve decided not to move forward.”

Most salespeople immediately assume something changed.
In reality, very little usually changed at all.
The concerns were there from the beginning.
The prospect simply never voiced them.
After working with thousands of B2B salespeople over the past three decades, I’ve found that the strongest performers don’t have better closing techniques.
They have better discovery conversations.
They’re not experts at handling objections.
They’re experts at preventing them.
By the time a prospect objects to your proposal, they’re often just putting words to concerns they’ve held for weeks.
That’s why discovery—not closing—is where MSP sales are really won.

Why Do MSP Sales Stall After The Proposal?

One of the biggest myths in sales is that objections happen at the end.
They don’t.

They develop quietly throughout the buying journey.
Every unanswered question…
Every unspoken concern…
Every assumption left unchallenged…
Adds another brick to the wall between you and the sale.
Then, when the proposal arrives, the prospect finally has a reason to delay.
“It’s more than we expected.”
“The timing isn’t right.”
“We’re going to stay where we are for now.”

Those aren’t always the real reasons.
They’re often the safest reasons.
The real concerns appeared much earlier.
Let’s look at the five most common ones.

1. Is Solving The Problem Important Enough?

One of the easiest traps to fall into is mistaking activity for intent.
The prospect replies to emails.
They attend meetings.
They ask intelligent questions.
They compliment your proposal.

None of that guarantees they’re committed to making a change.
Many MSP salespeople continue investing time simply because the prospect is being polite.
Politeness isn’t commitment.
Interest isn’t urgency.
One question I often recommend is:

“Can I ask you something honestly? Based on everything we’ve discussed, how important is solving this problem to your business this year?”

That single question changes the conversation.
If they tell you it isn’t a priority, you’ve saved yourself weeks—or months—of chasing a deal that was never likely to happen.
If they tell you it is important, you’ve confirmed you’re working on a genuine opportunity.

My Experience

Across hundreds of MSP sales reviews I’ve conducted, this is probably the biggest early indicator of pipeline quality.
Salespeople often measure engagement.
Successful salespeople measure commitment.

Why This Matters

A prospect who isn’t genuinely motivated rarely becomes more motivated after receiving a proposal.

The proposal simply gives them another opportunity to delay making a decision.
Instead of asking whether they like your solution, find out whether solving the problem matters enough for them to act.

2. Why Don't Prospects Believe Your MSP Can Deliver?

This objection has become far more common over the past few years.
Not because MSPs have become worse.
Because buyers have become more cautious.
Many businesses have already switched IT providers once.
Some have switched twice.
They’ve experienced poor communication, missed SLAs, failed migrations or promises that never materialised.
So when they sit across the table from you, they aren’t necessarily questioning managed IT services.
They’re questioning whether your MSP will be any different.

They might never say it out loud, but they’re thinking:

“Will they really answer the phone when we need them?”
“Will the onboarding disrupt the business?”
“Are they overpromising like the last provider?”
“Will this still feel this good six months from now?”

Until those concerns are addressed, they’ll struggle to move forward—no matter how impressive your proposal looks.

One of my favourite questions is:

“Can I ask what concerns you most about moving your IT support to another provider?”

It’s a simple question, but it often unlocks the real conversation.

Typical responses include:

“We’ve been promised fast response times before.”
“Our last migration was a nightmare.”
“I’m worried about the disruption to the business.”
“We’ve had providers disappear after we’ve signed.”

Now you know what evidence they’re looking for.

Instead of simply telling them you’re different, show them.

Share client success stories.

Walk them through your onboarding process.

Explain how you’ll minimise disruption.

Demonstrate your SLA performance.

Introduce them to customers who have successfully made the same transition.

The best MSPs don’t win because they promise more.

They win because they reduce the buyer’s perceived risk.

My Experience

One thing I’ve noticed working with MSPs is that technical capability is rarely the deciding factor.
Most providers can deliver excellent IT support.
What separates the winners is their ability to make prospects feel confident before they’ve signed the contract.
Confidence sells.
Technology supports it.

3. Why Don't Prospects Trust You?

This is probably the most uncomfortable objection because sometimes it has nothing to do with your company.
Sometimes it’s you.
Perhaps you’ve rushed discovery.

Perhaps you’ve spent too much time presenting.

Perhaps you’ve answered questions before fully understanding the business.

Or perhaps you’ve simply sounded like every other MSP they’ve spoken to.

Trust isn’t built through impressive PowerPoint slides.
It’s built by making the prospect feel understood.
If you genuinely feel trust is missing, don’t ignore it.
Address it.

One question I’ve used for years is:
“Can I ask you an awkward question? I get the feeling there’s still something making you hesitant. Have I missed anything, or is there something you’re unsure about?”

Most salespeople avoid asking that question because they’re afraid of the answer.
The best salespeople ask it because they want the answer.
You can’t rebuild trust until you understand what’s damaged it.

The Trust Equation

In my experience, trust in MSP sales is built through four simple behaviours:
Listening more than you speak.
Asking thoughtful follow-up questions.

Demonstrating genuine curiosity.
Providing evidence instead of promises.
Prospects don’t expect perfection.
They expect honesty.
Ironically, acknowledging uncertainty often builds more trust than pretending to have every answer.

4. Why Don't Prospects See Enough Value?

One of the biggest mistakes MSP salespeople make is talking about technology instead of business outcomes.

Your prospect isn’t buying:

24/7 monitoring
Microsoft 365 management
Endpoint protection
Faster response times
Backup software

They’re buying something much more valuable.

They’re buying confidence.

They’re buying fewer interruptions to their staff.

They’re buying reduced downtime.

They’re buying protection from cyber threats.

They’re buying the freedom to focus on growing their business instead of worrying about IT.

If those outcomes haven’t been explored during discovery, your monthly fee becomes the only thing the prospect has left to compare.

That’s when your proposal starts looking expensive.

During discovery, ask questions such as:

“What impact does your current IT support have on the business today?”

Then follow up with:

“If nothing changed over the next twelve months, what would that cost the business?”

Now you’re discussing:

Lost productivity.
Staff frustration.
Security exposure.
Downtime.
Customer experience.
Missed growth opportunities.

That’s a completely different conversation from discussing antivirus software or response times.

Features vs Outcomes

Your MSP Talks About	Your Prospect Thinks About
24/7 Monitoring	Less downtime
Cyber Security	Reduced business risk
Microsoft 365	Staff productivity
Backup & Recovery	Business continuity
Fast Response Times	Peace of mind
Strategic IT Reviews	Better business decisions

The best MSP salespeople don’t spend their meetings defending their price.

They help prospects understand the cost of doing nothing.

When buyers understand the commercial impact of staying where they are, investment becomes much easier to justify.

5. Are You Speaking To Someone Who Can Actually Say Yes?

This catches more MSP salespeople out than almost anything else.

You’ve built a fantastic relationship with the Operations Manager.

The Technical Director loves your proposal.

The IT Manager thinks you’re exactly what the business needs.

Then comes the sentence every salesperson dreads.

“We just need to run this past the owner.”

Suddenly you’re back to square one.

The person you’ve invested weeks with can’t actually make the decision.

This isn’t their fault.

It’s yours.

You should have established the buying process much earlier.

One simple question can prevent weeks of frustration:

“Apart from yourself, who else will need to believe this is the right investment before we move forward?”

Notice the wording.

You’re not asking who signs the contract.

You’re asking who needs to believe.

That subtle difference often reveals everyone involved in the decision-making process, from business owners and finance directors to board members and operational stakeholders.

Great salespeople don’t just identify decision-makers.

They understand how buying decisions are made.

That’s a huge difference.

In complex B2B sales—particularly managed services—multiple people influence the final outcome.

Your job is to uncover that process before the proposal lands, not after.

The Common Thread Behind Every Stalled MSP Sale

Looking back at these five reasons, there’s one pattern that connects them all.

None of them are really about closing.

They’re about discovery.

The prospect wasn’t interested enough.

They didn’t believe you could deliver.

They didn’t fully trust you.

They couldn’t see enough value.

Or they simply weren’t the person who could make the decision.

None of those problems suddenly appeared when you sent the proposal.

They were there all along.

The proposal simply exposed them.

This is why I spend so much time coaching MSP sales teams on discovery. A great discovery meeting isn’t about gathering information to write a proposal. It’s about understanding the prospect’s business well enough to remove uncertainty before they ever have to make a buying decision.

The better your discovery, the easier the proposal becomes.

Key Takeaways

If there’s one lesson I’d like you to take away from this article, it’s this:

Great MSP salespeople prevent objections instead of trying to overcome them.
Prospects buy certainty before they buy managed IT services.
Trust is built by asking better questions, not delivering better presentations.
Value comes from understanding business outcomes, not explaining technical features.
Most stalled deals can be traced back to something that wasn’t uncovered during discovery.

The next time a proposal goes quiet, don’t immediately assume it’s the price.

Ask yourself:

What concern did I fail to uncover?

More often than not, that’s where the answer lies.

Frequently Asked Questions

Why do MSP prospects go quiet after receiving a proposal?

In many cases, the proposal isn’t the problem. It simply gives prospects time to reflect on concerns that were never discussed during discovery. These concerns might relate to trust, perceived value, risk or internal decision-making.

How can MSP salespeople uncover objections earlier?

By asking open, consultative questions throughout the sales process rather than waiting until the closing stage. Great discovery creates honest conversations where prospects feel comfortable sharing concerns before they become objections.

Should MSPs discuss pricing early in the sales process?

Pricing should never be a surprise, but it should follow a thorough understanding of the prospect’s challenges, goals and the commercial impact of those challenges. When value has been established first, pricing discussions become far easier.

Why do prospects say they need more time to think?

Sometimes they genuinely do.

However, it’s also one of the safest ways to avoid expressing an underlying concern. Rather than accepting the response at face value, good salespeople explore what still needs to happen before a decision can be made.

What's the biggest mistake MSP salespeople make during discovery?

Talking too much.

Many salespeople spend discovery meetings explaining services instead of understanding the prospect’s business. The best discovery meetings are driven by curiosity, thoughtful questions and active listening.

If you're finding that too many proposals are ending with "We've decided to stay where we are" or "We need to think about it," the problem may not be your proposal at all.

It may be your discovery process.

At James White Sales Success, we help MSPs build structured, repeatable sales processes that uncover objections earlier, improve conversion rates and create a more predictable pipeline of high-value opportunities.

If you'd like to improve how your team discovers, qualifies and closes opportunities, get in touch to find out how we can help.

About the Author

James White is Founder of James White Sales Success and is known as The IT Sales Expert. Over the past three decades he has helped more than 5,000 businesses improve their sales performance, with a particular focus on helping Managed Service Providers build predictable sales pipelines, improve discovery conversations and win more high-value business.

Why Prospects Don’t Buy: The 6 Hidden Reasons MSP Deals Stall

James White — Mon, 22 Jun 2026 14:25:38 +0000

Executive Summary

MSP sales opportunities rarely stall simply because a prospect is busy. More often, the deal stops moving because something important is missing from the buyer’s decision-making process.

In managed services, prospects are not just buying IT support. They are trusting an MSP with their systems, cybersecurity, data, uptime and business continuity. That means hesitation is often driven by risk, uncertainty, previous poor experiences, unclear value or a lack of urgency.

The six most common reasons MSP prospects don’t buy are:

They don’t genuinely want it.
They don’t believe it will work.
They don’t trust you yet.
They can’t see enough value.
They can’t actually say yes.
The pain isn’t big enough yet.

Understanding which one applies helps MSPs stop chasing the wrong problem and start moving better-fit opportunities forward.

The 7 hard truths about MSP Growth

Why Do MSP Sales Opportunities Stall?

One of the most frustrating moments in MSP sales is when a prospect appears interested, attends meetings, asks good questions, receives a proposal and then disappears.

The natural assumption is that they are busy.
Sometimes they are.
More often, there is something preventing them from moving forward.
The challenge is that prospects rarely tell you the real reason. Instead, they ask for more time, request extra information, stop responding or allow the opportunity to drift.

Across the MSPs James White Sales works with, most stalled opportunities can usually be traced back to one of six reasons.

1. They Don’t Genuinely Want It

This sounds obvious, but it happens more often than many salespeople realise.

People are polite. Most business owners do not enjoy telling someone directly that they are not interested, particularly if you have invested time in meetings and built a good relationship.

Instead of saying:
“We’re not interested.”
They say:
“We need some time to think about it.”
“Leave it with me.”
“Can you send some more information?”

The longer the sales cycle, the more likely this becomes. Rapport builds, relationships strengthen and prospects often become reluctant to deliver disappointing news.
Sometimes a stalled deal is not a sales problem.
It is simply a lack of genuine interest.

2. They Don’t Believe It Will Work

In managed services, this is one of the most common reasons prospects fail to move forward.

Many businesses have been let down by IT providers before. They have heard promises about fast response times, proactive support, strategic guidance and improved cybersecurity. Unfortunately, many have experienced something very different.

As a result, prospects are not just evaluating your proposal.
They are evaluating whether they are prepared to trust another provider with a critical part of their business.

This matters because MSPs are often responsible for areas that directly affect business continuity, cybersecurity and operational risk. CISA highlights that organisations using MSPs need to consider the risks associated with outsourced IT management, including access, security and resilience.

Most prospects will not openly admit this concern.
Instead, they ask for more case studies.
They request references.
They want another meeting.
What they are really saying is:
“Help me believe this will work for us.”

3. They Don’t Trust You Yet

Trust is the foundation of every successful MSP sale.
Without trust, nothing else matters.

MSPs are asking prospects to hand over responsibility for systems, data, cybersecurity, infrastructure and business continuity. That requires a significant level of confidence.

The challenge is that prospects rarely tell you they do not trust you.

Trust issues often appear disguised as:

This is why testimonials, referrals, case studies, customer success stories and social proof are so powerful.

People buy certainty before they buy solutions.

Building trust is one of the most important skills in MSP sales. As I discussed in Desperation is a Stinky Aftershave, prospects can quickly sense when a salesperson is trying too hard to close rather than genuinely understand their situation.

4. They Can’t See Enough Value

This is where many MSPs struggle.
The prospect says:
“It’s too expensive.”
The salesperson immediately starts considering discounts.
But price is rarely the real issue.
Value is.
Business owners do not buy managed services because they want monitoring, patching, endpoint protection or Microsoft licensing.

They buy because they want:

Less downtime
Fewer headaches
Better productivity
Reduced risk
Greater security
Confidence that technology is not holding the business back

This is important because downtime and IT disruption can have a significant commercial impact. Recent industry reporting has shown that unplanned downtime can cost large organisations substantial sums and damage reputation, productivity and customer confidence.

If your proposal focuses too heavily on technical features rather than business outcomes, prospects will struggle to justify the investment.

When buyers push back on price, what they are often saying is:
“I don’t yet see enough value to justify the cost.”

If price objections are a recurring challenge, you may find my article on How To Deal With Price Objections useful, where I explore the three most common causes of pricing resistance.

5. They Can’t Actually Say Yes

This is one of the most common qualification mistakes in MSP sales.
You spend weeks speaking to a prospect.
You understand their challenges.
You build a strong relationship.
You prepare a proposal.
Only to discover that the person you have been speaking to is not the person who can make the final decision.

Perhaps it is an Office Manager.
An Operations Director.
An Internal IT Manager.
Or a Finance contact.

They may genuinely support your proposal.
But support and authority are not the same thing.

Before investing significant time in an opportunity, MSPs need to understand:

Otherwise, you risk selling to someone who simply cannot say yes.

Qualification and process are critical. In How to Build a Scalable Sales System, I explain why documenting your sales process and identifying decision-makers early can dramatically improve conversion rates.

6. The Pain Isn’t Big Enough Yet

This may be the hardest lesson in MSP sales.
A prospect can agree with everything you have said.
They can acknowledge the risks.
They can recognise the weaknesses in their current provider.
They can even admit they need to improve.
And still do nothing.

Why?

Because the pain of staying where they are feels smaller than the pain of change.
Their support is not great.
But it is acceptable.
Their cybersecurity is not ideal.
But they have not suffered a breach.
Their systems are slow.
But the business is coping.

One of the biggest mistakes salespeople make is assuming awareness creates urgency.
It does not.
Prospects act when the cost of staying the same becomes greater than the cost of changing.
Until that happens, many opportunities remain stuck.

This challenge is particularly common in the MSP space. In The 7 Hard Truths About MSP Growth, I discuss why long sales cycles and delayed buying decisions are often a normal part of selling managed services.

What Should MSPs Do When a Deal Stalls?

The biggest mistake salespeople make is trying to solve the wrong problem.
They handle a price objection when the issue is trust.
They send another proposal when the issue is authority.
They increase follow-up when the prospect simply does not want to buy.

The better question is not:
“How do I chase this deal harder?”

The better question is:
“What is really missing?”
Most stalled MSP opportunities do not disappear because prospects are busy.

They stall because one of six things is missing:

The better you become at diagnosing what is really stopping the prospect from moving forward, the faster you will win more deals.
Because in sales, the solution is only obvious once you have identified the real problem.

How to build a scalable sales system for 2026

Desperation Is a stinky after shave

What Questions Should Salespeople Ask Next?

When a prospect says: “We’re reviewing our options.”
A poor salesperson thinks: Excellent. An opportunity.
A great salesperson asks: What made you start reviewing your options now?

Then they listen.
And when they get an answer, they dig deeper.

For example:

This is where sales happen.
Not when you pitch.
When you understand.

FAQ: Why MSP Prospects Don’t Buy

Why do MSP prospects go quiet after receiving a proposal?

MSP prospects often go quiet because they have an unspoken concern. They may not believe the solution will work, may not trust the provider yet, may not see enough value or may not have the authority to approve the decision.

Is price the main reason MSP deals stall?

Price is often the objection, but it is rarely the full reason. In many cases, the prospect cannot yet connect the cost of the MSP service to the business outcomes they care about, such as reduced risk, better productivity, fewer disruptions and stronger cybersecurity.

How can an MSP build more trust during the sales process?

MSPs can build trust by using relevant case studies, client testimonials, referrals, clear onboarding plans, transparent pricing and specific examples of how they have solved similar problems for similar businesses.

Why do prospects say they need more time to think?

Sometimes they genuinely need time. But often, “I need to think about it” means something else is missing. It may indicate a lack of belief, unclear value, hidden stakeholders, fear of change or weak urgency.

How can MSPs qualify decision-makers more effectively?

MSPs should ask early who is involved in the decision, how the budget is approved, what criteria will be used to compare providers and what the buying process looks like. This helps avoid spending weeks with someone who cannot approve the purchase.

What is the most common reason MSP sales opportunities stall?

In many MSP sales conversations, the most common reason is a lack of belief. Prospects may have been disappointed by previous IT providers and need evidence that this time will be different.

The Sale Is In The Follow-Up Question

James White — Sat, 13 Jun 2026 07:11:10 +0000

Executive Summary

Many salespeople lose opportunities because they stop at the prospect’s first answer.

A prospect says they’re “reviewing options,” “not getting value,” or “having a few issues,” and the salesperson immediately starts talking about their services.

The problem is that the first answer is rarely the real answer.

The best salespeople understand that sales success comes from asking follow-up questions, listening carefully, and uncovering the real challenges beneath the surface.

In this article, I’ll explain why the sale is often hidden behind the prospect’s first response and how asking better questions can dramatically improve your sales conversations.

Most Salespeople Stop Too Early

Last week I wrote about what I called “The Stinky Aftershave.”
The central idea was simple:
Most salespeople walk into meetings focused on selling.
The best salespeople walk into meetings focused on understanding.
That is the mindset.
This week, I want to give you the method.
Because once you stop trying to sell, the obvious question becomes:

The answer lies in one simple principle:

The sale is in the follow-up question.

Why Is The First Answer Rarely The Real Answer?

A prospect says: “We’re reviewing our options.”
And the salesperson immediately starts talking about their services.

A prospect says: “We’re not sure we’re getting value from our current provider.”
And the salesperson starts explaining why their support desk is better.

A prospect says: “We’ve had a few issues recently.”
And suddenly the salesperson is halfway through a presentation.

The problem is that none of these statements are the real problem.
They’re simply the starting point.

Great salespeople understand that:

What Questions Should Salespeople Ask Next?

When a prospect says: “We’re reviewing our options.”
A poor salesperson thinks: Excellent. An opportunity.
A great salesperson asks: What made you start reviewing your options now?

Then they listen.
And when they get an answer, they dig deeper.

For example:

This is where sales happen.
Not when you pitch.
When you understand.

What Have I Learned From Working With Thousands Of Business Owners?

Over the last three decades, I’ve worked with thousands of business owners, salespeople and sales teams.

One pattern appears repeatedly.

The salespeople who consistently win more business are not usually the best presenters.

They’re the best listeners.

They don’t rush to recommendations.

They don’t immediately start talking about products.

They spend more time understanding the problem than explaining the solution.

Because of that, prospects trust their advice.

I’ve seen salespeople completely transform their results simply by becoming more curious and asking one or two additional questions before presenting their solution.

What's The Difference Between Hearing And Listening?

One of the biggest mistakes salespeople make is confusing hearing with listening.

Most salespeople hear.
The best salespeople listen.

They listen for:

A prospect might say: “It’s not a major problem, but the team do complain about response times.”

Most salespeople move on.
Great salespeople stop.
Because they know they’ve found something important.

They ask:

Now we’re getting somewhere.

Real MSP Sales Example

I see this regularly when working with MSPs and technology businesses.

A prospect initially says: “We’re just looking around.”
Many salespeople hear: Potential opportunity.

The best salespeople hear: Something has triggered this review.
Through questioning, we often discover:

The original statement wasn’t the real issue.

The follow-up questions uncovered it.

Internal Resources You May Find Useful

If you found this article helpful, you may also enjoy:

Frequently Asked Questions

Why is the first answer rarely the real answer?

Because prospects often give surface-level responses initially. The underlying issue usually emerges through thoughtful follow-up questions.

How can I improve my discovery conversations?

Focus on understanding before presenting. Ask additional questions, explore impact, and avoid rushing to solutions.

Why are great salespeople good listeners?

Because listening helps uncover the real problem. Understanding the true challenge allows you to make more relevant recommendations.

What questions should MSP salespeople ask prospects?

Questions about business impact, frustration, risk, current provider performance, and what prompted the conversation often reveal valuable insights.

How many follow-up questions should I ask?

There is no magic number. Continue asking questions until you fully understand the problem, its impact, and why it matters.

Final Thoughts

The sale is not in the first answer.
The sale is in the follow-up question.
And then the next one.
And the one after that.

Because the deeper you understand the problem, the more obvious the right solution becomes.
The best salespeople are not the best talkers.
They are the best listeners.

So this week, challenge yourself.
Ask one more question than you normally would.
Then ask another.
And another.
You might be surprised by what you discover.

Helpful resources you might find

Desperation is a Stinky Aftershave

James White — Mon, 08 Jun 2026 07:12:36 +0000

Executive Summary

Desperation is one of the biggest deal-killers in sales. When prospects feel a salesperson is focused on selling rather than understanding, trust disappears and the salesperson becomes just another vendor. The best salespeople approach conversations as problem-solvers, listening carefully, asking insightful questions and focusing on the prospect’s challenges before recommending a solution. The less desperate you are to sell, the more likely you are to make the sale.

Desperation is a Stinky Aftershave

You might not notice you are wearing it, but everyone else in the room can smell it.

And in sales, especially in IT and MSP sales, I see this all the time.

A salesperson walks into a meeting with a prospect and, whether they realise it or not, their whole energy says: “I need to sell something here.”

They want to pitch.

They want to prove themselves.

They want to explain the service.

They want to tell the prospect how good they are, how experienced the business is, how quickly they respond to tickets, how strong their cyber credentials are, how brilliant the onboarding process is and how they are different from every other MSP in the market.

And here is the brutal truth.

Most prospects don’t care.

Not yet anyway.

The prospect isn’t thinking about any of that.

They are thinking about themselves:

Their problems.
Their frustrations.
Their risks.
Their challenges.

Before they care about what you do, they need to believe you understand what they are dealing with.

That is where so many salespeople go wrong – they walk into meetings with a preconceived idea of what they want to sell, instead of being curious about what needs to be solved.

And prospects can feel it.

They might not say it. They might sit politely and listen. They might nod along and let you finish your pitch. But deep down, they are thinking: “This person is not listening to me. They are just waiting for their turn to talk.”.

The moment that happens, you stop being an advisor.

You become a vendor.

And vendors get compared on price.

The funny thing is that many business owners were actually better salespeople before they ever hired a salesperson.

I see this regularly when working with MSP owners and IT businesses. The businesses that consistently win new clients focus on diagnosis first and recommendations second.

Not because they had sales training.

Not because they had a CRM.

Not because they had some fancy discovery framework.

They were better because they cared about solving problems

When you started your business:

You didn’t lead with a presentation.
You didn’t start with your packages.
You didn’t launch into a list of features.

You sat down and tried to understand what was wrong.

You wanted to know what was causing frustration.

You wanted to know what wasn’t working.

You wanted to know what was keeping the customer awake at night.

You focused on the problem.

And because you focused on the problem, people trusted you.

As businesses grow, they often lose this.

They replace curiosity with process.

They replace listening with pitching.

They replace problem-solving with product explanation.

And then they wonder why conversion rates start falling.

The truth is simple.

Most prospects don't want your pitch.

Not yet.

They want to know whether you understand their world.

Whether you understand the consequences of getting it wrong.

Whether you genuinely care about helping them.

Trust comes before solutions.

Trust comes before proposals.

Trust comes before sales.

And trust is impossible to build if your prospect feels like you’ve already decided what you’re going to sell before you’ve understood their situation.

The best salespeople aren’t obsessed with making a sale.

They’re obsessed with understanding the problem.

In fact, one of the most effective ways to do this is through structured questioning. I’ve written previously about my LAPS methodology and how it helps salespeople uncover what prospects are really thinking and feeling.

Because when prospects feel understood,

they relax,
they open up,
they tell you more,
and they trust what you recommend.

That’s when sales become easier.

But here’s the important thing…

Mindset Before Method

Whenever I work with sales teams, people often ask me, “What’s the best sales technique?” or “What questions should I ask?”

The truth is, the technique doesn’t matter if the mindset is wrong.

If you walk into a meeting desperate to sell, no script in the world will save you.

If you walk into a meeting determined to understand, you’ll naturally ask better questions, listen more carefully and build more trust.

The mindset comes first.

The method comes second.

And next week, I’ll show you exactly what that method looks like.

I’ll share how the best salespeople uncover what is really going on beneath the surface, why the first answer is almost never the real answer, and how a few simple follow-up questions can completely transform your sales conversations.

Spotting the stinky aftershave is one thing.

Knowing what to wear instead is another.

We’ll cover that next week

In conclusion, the irony is that the less desperate you are to sell, the more likely you are to make the sale. People buy from people who are trying to solve their problem, not people who are trying to hit a target.

So next time you walk into a meeting, leave the stinky aftershave at home.

Don’t go in determined to sell.

Go in determined to understand.

That’s my view anyway…

If you’d like to hear me expand on this topic, I’ve also discussed the importance of curiosity, questioning and trust-building on the podcast.

Do you agree with me?

Have you ever been on the receiving end of a salesperson who was trying far too hard to sell?

Or have you caught yourself doing it?

Let me know. I read every reply, even if I don’t always get chance to respond to them all.

Thanks as ever for being part of my community.

Have a brilliant sales week ahead and remember, Eat or be Eaten.

Frequently Asked Questions

Why do prospects dislike sales pitches?

Most prospects don’t dislike salespeople; they dislike feeling sold to.

When a salesperson launches straight into a pitch, the prospect immediately feels like the conversation is about the salesperson’s targets rather than their own challenges.

Buyers want to feel understood before they hear recommendations. They want confidence that you understand their situation, the risks they face, and the outcomes they are trying to achieve.

The best sales conversations start with curiosity, not a presentation.

How can salespeople avoid sounding desperate?

The simplest way to avoid sounding desperate is to stop focusing on what you want to sell and start focusing on what the prospect needs to solve.

Desperate salespeople enter meetings hoping to present their solution.

Trusted advisors enter meetings hoping to understand the problem.

Ask questions, listen carefully, and avoid rushing to explain your services. The more interested you are in understanding the prospect, the less pressure they will feel from you.

Ironically, that often makes them far more willing to buy.

Why are founders often better at sales?

Many founders become successful because they built their business around solving a specific problem.

When they meet prospects, they naturally focus on understanding the challenge rather than delivering a sales pitch.

They ask questions because they are genuinely curious.

As businesses grow, sales processes and presentations often replace that curiosity. The challenge for sales teams is to maintain the same problem-solving mindset that helped the founder win customers in the first place.

How do you build trust in a sales conversation?

Trust is built when a prospect feels heard, understood, and respected.

That means asking thoughtful questions, listening without interrupting, and taking the time to understand the full situation before offering advice.

Many salespeople rush to recommend a solution after hearing the first problem.

The best salespeople dig deeper.

They explore the impact of the problem, why it exists, how long it has been happening, and what happens if nothing changes.

The more thoroughly you understand the prospect’s world, the more credibility your recommendations will have.

What should MSP salespeople focus on during discovery meetings?

The purpose of a discovery meeting is not to sell managed services.

The purpose is to understand the prospect’s business.

Focus on uncovering:

Current frustrations with IT
Business risks and vulnerabilities
Cyber security concerns
Productivity challenges
Previous experiences with IT providers
Future growth plans
The consequences of doing nothing

The more clearly you understand the problem, the easier it becomes to determine whether your services are genuinely the right fit.

A good discovery meeting should leave the prospect feeling understood, not pitched to.

Why do the best salespeople ask so many follow-up questions?

Because the first answer is rarely the real problem.

A prospect might say they are unhappy with response times, but the real issue could be a lack of trust, poor communication, cyber security concerns, or frustration that their provider is not being proactive.

Great salespeople understand that valuable information is often hidden beneath the first answer.

By asking thoughtful follow-up questions, they uncover the real challenge, which allows them to provide better advice and more relevant solutions.

As I often say, the sale is not in the first answer.

The sale is in the follow-up question.

“Over the last 30 years, I’ve worked with more than 5,000 business owners, salespeople and sales teams. One pattern appears repeatedly: the salespeople who focus most on understanding the problem consistently outperform those who focus on presenting the solution.

Prospects rarely buy because of the best pitch. They buy because they feel understood.

The Difference That Wins Deals

Create Urgency Without Discounting

James White — Sat, 02 May 2026 09:29:40 +0000

In today’s edition, we’re talking about urgency… and more importantly, how to create it without immediately reaching for a discount when things get uncomfortable.

People love a deal. That’s never going to change.

If a buyer thinks there’s even a small chance they can get what you’re offering for less, they’ll usually take that opportunity. Not because they’re difficult, but because it’s human nature.

The problem is what happens when you give in.

Because the moment you drop your price to “get it over the line,” you’re not just winning a deal, you’re setting a precedent. You’re showing the buyer that your pricing is flexible and, more importantly, that pressure works on you.

That’s a tough position to recover from.

The Reasons for the Urgency?

It’s worth asking yourself a slightly uncomfortable question here…

Why do you feel the need to discount in the first place?
Is it genuinely because the price is wrong?
Or is it because you need the deal more than they do right now?

Targets, deadlines, pipeline pressure… it creeps in quickly. And before you know it, you’re trying to solve your urgency problem with their wallet.

But here’s the reality—your timeline and their timeline are rarely the same.

And when you try to force urgency through price, it usually backfires.

How to Create Urgency

So if discounting isn’t the answer, what is?

It starts with understanding, not pushing.

When you take the time to really uncover what’s going on for the buyer (the real problem, not just the surface-level version) they begin to feel understood. And when that happens, conversations move forward more naturally.

From there, you need clarity on timing. When do they actually want to solve this? If it’s not a priority for them now, dropping your price won’t magically make it one.

You can also introduce urgency through real constraints:

your availability,
your capacity, or
timelines that exist regardless of price.

These are far more credible and far more effective.

And then there’s the most important piece…

Helping them understand the cost of doing nothing.

What happens if they wait? What continues to frustrate them? What gets worse?

When that becomes clear in their mind, urgency no longer needs to be manufactured.

Your Rates Are There for a Reason

I was talking about this on a podcast recently using the example of flights.

You don’t negotiate with an airline. The price is the price.

You either see the value in that seat, at that time, for that journey… or you don’t. And that’s exactly how your service should be positioned.

Because the moment you introduce a discount at the point of decision, whether you realise it or not, you’re sending a signal that your original price wasn’t solid.

It doesn’t build trust. It raises questions.

Your pricing exists for a reason. It reflects the value you deliver, the work that goes in, and the outcomes you create.

And if you don’t stand behind it, why should anyone else?

So next time you feel that pull to “just drop it slightly” to get the deal done…

Pause.

Go back to the problem. The impact. The consequence of waiting.

That’s where real urgency lives.

Have a brilliant sales week ahead, and remember: Eat or be eaten.

it’s 3 or 4

James White — Tue, 28 Apr 2026 11:12:48 +0000

In today’s edition, we explore why you need more deals in your pipeline than you think to achieve your revenue goals—and what the implications are if you don’t have this in place. Let’s get to it.

We always need more than we think.

Especially in sales.

I was asked a question some time ago about how you can ensure you hit the targets that you have.

Do you need to be lucky?
Do you need to work incredibly hard?
Do you need to charge higher prices?

All these things help, but there is one simple way of hitting your targets, and that’s to build a pipeline full of leads.

So, what do you need in your pipeline? And what should a good pipeline look like?

I always work on a simple rule:

Ensure that your pipeline and the final stages of your sales process are a minimum of 3 (and ideally 4) times the value of the target you want to hit.

Let’s break it down a bit more.

Let’s say your business wants to achieve a new
revenue target of £500,000 for the year.

You may have certain months that are stronger or weaker than others, but for the sake of this example, let’s say the target is spread across a 12-month period.

To achieve your target, you will need to hit a revenue of £42,000 per month.

So, to hit this number, what should the value of your pipeline be?

The answer is a minimum of £126,000, but ideally £168,000. Let me explain why.

There are two main reasons:

We don’t win all the business that we have (or think we will)
All too often, deals don’t come in when we want them to

I was once told some sage advice by an old Sales Director:

“Plan conservatively but execute optimistically.”

Put simply, don’t do what most salespeople do
and expect that everything will come in. Be realistic.

We always need more than we think.

We might have a good feeling about all the leads we have, but if you are converting more than 2 in 3 leads at the final stage of your sales process, then you are probably too cheap. Even the very best salespeople in the world wouldn’t expect to convert more than 2 out of 3 in the final stages.

In addition, even good deals that will happen often get delayed for different reasons. A person has left or just joined the business, a budget has been put on hold for a few months, or a bigger, more important priority has come up.

Whilst we always try to avoid these issues, they happen. It’s life.

What matters is that we don’t totally rely on them to achieve the targets we want. Doing this means we become prisoners of hope—and no one wants to be a prisoner of anything.

When our pipeline is the same as, or just over, the target, we also exude desperation—which is always a bad thing in a sales deal. We make rash decisions and push prospects to do things “just to hit the target,” and invariably that works against us.

Yet when we have a funnel full of leads that we are engaging with and having good conversations with, the pressure is off. That comes through in the way we work, and that “hidden 10%” is the secret to winning more.

The best way to see your pipeline is like people spinning plates. They continue to put plates up on tall needles and spin them so they can keep adding more. They keep an eye on each plate and give them a nudge now and again to keep them going—until the end of the act, when all the plates come down in an orderly way.

So, what is the best way to build up a 3 to 4 times pipeline?

ABP – Always Be Prospecting.

All too often, people do some prospecting, add some good deals to the pipeline, and then get overconfident. They assume that because they have £500,000 in their pipeline, the year is done. They relax. They take their foot off the gas—and when this happens, the car comes to a stop.

The way to avoid this is to put time aside daily for new prospecting.

Whether that’s contacting people through LinkedIn, sending prospecting videos, making calls, or another form of outreach—build it into your routine.

Make it a discipline. Set yourself mini targets: connect with 3 people a day, create 5 videos, or make 10 calls.

When you do this (alongside your existing sales work), you give yourself the best chance of adding new leads—and you also subconsciously take the pressure off the current deals in your pipeline.

What’s the worst that can happen?

You have too much business coming in?
You can choose who you work with?
You can raise prices due to demand?

None of these are bad outcomes.

So, work on the rule of 3 or 4.

Commit to doing something daily to build your pipeline.

You can never have enough leads—and when you have more than you need, good things start to happen, and targets start to get hit.

Try this out and let me know how you get on. A good starting point is to look at your current target, review your pipeline (especially the final two stages), and identify the gap. If it’s not 3 to 4 times the target, get to work.

Does this cover a challenging sales or business situation you’ve had?

If not, what would you like me to cover in a future newsletter?

Let me know. I read every reply, even if I can’t respond to them all.

Thanks, as ever, for being part of the community.

Have a brilliant sales week ahead, and remember: Eat or be eaten.

You can’t scale without it

James White — Mon, 20 Apr 2026 13:55:29 +0000

I spend much of my time talking to CEOs and business owners and helping them build plans for growth.

Growth is normally a pretty simple equation.

More customers and/or larger customers + increased prices – lower costs of customer acquisition and delivery = profitable growth

Profitable growth = smiley-faced CEOs and leaders

Whilst it seems simple enough, achieving that growth is not a simple task, and especially not for time-poor leaders. The business needs more leads to be converted into customers, and quite simply, this needs to happen without them needing to be involved.

Quite simply, they don’t have the time to engage in all of these conversations when they have other aspects of the business to focus on.

They want business to be brought in and for the tills to buzz whilst they focus on partnerships, delivery, raising money—the list goes on. In their heads, winning business is easy. They did it at the start, and it’s why the company has grown.

All of this is true, but one of the biggest mistakes I see business leaders making when they want to grow their business is not creating a sales playbook or blueprint for success.

The leader has a clear idea of how they want to grow and what others should do to bring new clients on board. For them, sales or winning new business is easy. It happens as a result of the knowledge and skills they have developed over time.

Just because they know what to do, however, doesn’t mean that others are automatically going to know what to do and how to approach certain situations. I always remind CEOs and sales leaders that their sales teams aren’t mind readers or psychics.

Without clear guidance and a blueprint to follow, it is highly likely that the team will drift off course and fail.

We have put together several ‘Business Growth Playbooks’ for organisations over the last few years, and there are three critical factors which we would advise you put in place if you want your future growth to be consistent and strong.

Point 1: Identify past areas of success

Work out where you were strong in the past and use this as the starting point to help others achieve success.

Why did the customers you signed up start to work with you?
What was it that you offered that made them commit to you?

Try to identify two to three common characteristics that stood out from those early successes and use these as the basis for others to build on. Don’t just choose anyone. Know where you achieved past success and what problem you solved for this group of people, and make that the starting point of your playbook.

Either document it yourself or bring someone in to document it. My company can help if you don’t have time.

“Scaling a business is not about doing more yourself; it’s about building systems that allow others to succeed without you.”
Author Unknown

Part 2: Understand your sales journey and process

Whilst you would love to think as a leader that you won every bit of business that you went for, we both know that’s not true.

You had success, sure, but you didn’t convert every call into a meeting or every meeting into a confirmed sale. There were times when you would have shared proposals which didn’t get through, and you learned as a leader that this was all part of the sales process and journey. Your team is going to go on the same path as you.

Outline the journey that you went on with new customers. At what points in the journey did you know when prospects weren’t a good fit? What were the steps in the process that you used when you won a deal? Did you do a demo, a site visit, or arrange for another customer to speak with them?

Help your team to understand the ideal buyer journey and process you went through and what rates of conversion you had at each stage. It will not only help them win business, but it will help keep everyone realistic about what can and can’t be achieved.

“Process is what turns individual success into organisational success.”
Michael Gerber

Part 3: Identify how to handle inbound leads and approach outbound prospecting

This is the nuts and bolts of good selling, and it’s vital that there is a playbook for others to follow. This is especially important if you want your company to be represented in the right way. This sets out the behaviours and ways of operating that you want from your team.

How should they engage with new inbound leads?
What should they do, and what should they not do?
What questions should they ask?
What questions did you ask that got you results?
How did you qualify leads to know whether it was right to spend more time with them?

The list goes on—and this is just with inbound leads.

There is a right and wrong way of engaging with those who don’t know your company, and if you let the team just do whatever they want, you will get the business version of the Wild West, which can cause lots of issues.

Want my simple guide and playbook on this?

It’s here:

Build a clear plan of how to go about winning new business and document it within a playbook which is a live, iterative plan that gets updated and used. Make it something that the team relies on and which you can use to measure results.

It is also vital within this part of your playbook that you include how they should react to typical responses. What should they say or do when someone ignores their call or doesn’t turn up for a meeting?

Don’t forget these small but critical elements. They are vital. And always remember—you may know how to handle these situations, but they may not. Give them the tools to know what to do and say, and you stand a far better chance of achieving the business growth plans that you desire.

As ever, if you need support or want to talk through how you can start to scale and grow your business, my team and I are here to help.

Have a brilliant week sales week ahead and remember: Eat or be Eaten.

Until the next time,

James

Why introverts can be the best at sales

James White — Sat, 14 Dec 2024 10:44:11 +0000

Hello Reader,

If you’re anything like me, you’re naturally enthusiastic and eager to engage in conversations.

There’s a widespread belief that people who are super extroverted and confident are, or will be… good at sales.

But there’s one skill I’ve had to refine over the years that has made all the difference in my sales success: knowing when to shut up.

It might sound counterintuitive, but talking less and listening more is a game changer.

In fact, the best salespeople are the ones who master the art of silence at the right moments.

So, it might not surprise you that introverted people tend to have a better understanding of people.

Because when you’re introverted, you’re not speaking much in groups.

That means you’re probably listening. When you listen carefully, you can hear everything and, as a result, have a better understanding of what’s going on.

That’s a mighty skill to have. It’s easier to learn to be confident than it is to learn to understand people. And that is why introverted people actually have a more substantial chance to be the best salespeople – if they keep that skill and master confidence.

It is still essential that you talk during sales; it’s just that you need to know when to talk… and when not to.

With that in mind, here are three critical times when you should stop talking and give your prospect space to speak.

1. When You Ask a Powerful Question

One of the biggest mistakes I see salespeople make is asking a probing or open-ended question and then immediately following it up with a stream of their own thoughts.

For instance, you might ask a critical question like: “How are you planning to fund your expansion?”

This is a significant question that can drive the conversation forward, but what happens next is crucial.

Most salespeople, eager to keep the momentum going, dive straight into additional comments, rephrasing the question, or offering potential answers. What I’ve learned, however, is that the silence after asking a tough question is your greatest asset.

Here’s why: Pausing after asking a probing question puts the spotlight on your prospect. It shows them that you’re truly interested in hearing their response. More importantly, it gives them the time to think and elaborate, providing insights into what really matters to them.

If you ask, “How are you going to fund your expansion plans?” and immediately follow up with another question or comment, you’re taking away the space for your prospect to think through their answer.

Pausing to let your prospect answer fully (without interrupting them) shows a high level of emotional intelligence. You’re not rushing them, and you’re not undervaluing their thoughts. You’re letting them tell you what they need, what their challenges are, and ultimately what’s driving their decision-making process. That’s powerful.

2. When You Get an Objection

Handling objections is an inevitable part of any sales process. Your prospect might say, “I really like your product, but it’s too expensive”, or “We’re not looking to make a change right now.”

Now, the natural instinct for many salespeople is to immediately start defending their product, justifying the price, or explaining why their solution is the right choice. And yes, early on in my career I’ve made this mistake myself.

However, when a prospect raises an objection, your immediate response shouldn’t be a flood of words trying to fix their concerns. Instead, pause.

Let the objection settle. Ask them for clarification if needed. Something as simple as saying, “Thanks for sharing that, I completely understand your concern. Could you tell me more about what you’re thinking regarding [x]?” can open the door for a more meaningful conversation.

Rushing to answer an objection makes you sound desperate.

When you stop talking and just listen, you give your prospect the opportunity to reframe their objection or even answer their own concerns. More importantly, it allows you to gather the information you need to craft a more thoughtful, personalised response that addresses their specific concerns.

3. When You Discuss Price

This is one of the trickiest moments in any sales conversation, right? I’ve seen it time and time again: salespeople mention the price and then immediately start talking about discounts, added bonuses, or justifications to make the price seem more reasonable.

They do this because they’re nervous about the prospect’s reaction to the price, and they hope that lowering the price or offering extras will seal the deal.

But here’s what you should do: The moment you mention the price, stop talking.

This shows that you’re confident in the value of your offering and that you’re not trying to undercut your own value.

It’s a simple but incredibly powerful move.

If you’ve set the price and then immediately follow it up with a justification, you’re essentially telling the prospect that you’re unsure about the price, and they’ll pick up on that.

When you pause, it lets your prospect digest the information, think about it, and even vocalise any concerns. That moment of silence can often lead to a more thoughtful conversation about the value of your service.

They might even come back with a counteroffer or a question that allows you to dive deeper into their needs and how your service can help.

The Power of Silence: A Final Word

Sales isn’t just about talking. It’s about knowing when to talk and when to listen.

If you can master the moments of silence, you’ll find that your conversations become more meaningful, your relationships with prospects become stronger, and your sales results improve dramatically.

In my early days in sales, I worked hard to rein in my natural enthusiasm and learn to pause at the right moments. But every time I’ve done it, I’ve seen the payoff – whether it’s closing a deal, gaining valuable insights, or building trust with a prospect.

I hope these insights help you take your sales skills to the next level. Until next week, take care and good luck.

James