James White

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

James White — Mon, 13 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

Time to drink my own champagne

James White — Sat, 30 May 2026 09:47:30 +0000

In today’s edition, we explore one of the biggest mistakes I made in my first business, why “small businesses” is not a target market, and why it is finally time for me to drink my own champagne and focus on a niche within a niche within a niche. Let’s get to it.

One of the things I talk about a lot is niches.

In fact, if you’ve listened to my podcast, attended one of my talks, or worked with me directly, you’ve probably heard me say the same thing over and over again.

Be something to someone. Not everything to everyone.

And yet, if I’m being completely honest, this is advice I haven’t always followed myself… which means it is time to drink my own champagne.

For years, we have helped business owners from a wide range of industries improve their sales performance. We’ve worked with manufacturers, professional services firms, software companies, consultants, construction businesses and many others.

The challenge with serving everyone is that eventually your message becomes too broad.

You become relevant to lots of people.

But highly relevant to very few.

And relevance is what drives sales.

One of the biggest mistakes I made in my first business was saying our target market was “small businesses”.

There were millions of them. At the time, that sounded fantastic – a huge market with endless opportunity.

The problem? "Small businesses" isn't a target market. It's far too broad.

Looking back, we should have focused much sooner. For example:

Accountants.

Then a specific type of accountant.
Then a specific challenge within that market.

A niche within a niche within a niche.

The businesses that win are rarely the ones trying to appeal to everybody.

They are the ones that become known for solving a specific problem for a specific group of people.

Which brings me to the point of today’s email.

From June onwards, we are going to be focusing much more of our content on MSPs (Managed Service Providers).

I will still be sharing lots of sales content that is applicable to all industries, but the examples and focus will be MSP-driven. I appreciate that if this isn’t your area, then you may decide my email is no longer for you. If that’s the case, then I totally respect and understand that.

Why focus on MSPs?

Because it is our sweet spot.
It is the audience we understand best.
It is where we know we can create the biggest impact.

And it is where we see the same sales challenges appearing time and time again.

Businesses that rely heavily on referrals.
Founders who are carrying too much of the sales burden themselves.
Companies with excellent technical delivery but inconsistent lead generation.
Sales processes that exist in someone’s head rather than in a repeatable system.

The fear many people have is that focusing on a niche means turning opportunities away.

I don’t see it that way.

The service can always be adapted.

The real question is whether your message is relevant enough to get attention. Because when somebody reads your content and thinks, “That’s exactly my situation”, everything changes!

Your marketing improves.
Your sales conversations become easier.
Your positioning becomes stronger.
And your prospects are more likely to engage.

So from June, expect more content around:

Generating leads for MSPs
Building predictable sales pipelines
Creating sales processes that don’t rely on the founder
Increasing client value and retention
Winning larger and better-fit opportunities
Building a business that can grow without everything depending on you

This isn’t a change of direction.

It’s a sharpening of focus.

It’s us doing exactly what I encourage other business owners to do.

Finding our sweet spot.

Doubling down on relevance.

And becoming something to someone rather than everything to everyone.

So let me leave you with three questions.

Is there enough of them?
Are they prepared to pay?
And do you actually enjoy working with them?

If the answer is yes to all three, don’t be afraid to focus.

In fact, it may be the most important growth decision you make.

For us, the answer is clear, which is why it’s time to drink our own champagne.

Focus isn’t limiting. Focus is liberating.

Thanks as ever for being part of my community.

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

Referrals Aren’t a Growth Strategy

James White — Sat, 23 May 2026 13:31:30 +0000

In this week’s edition, we will dig into why you cannot rely on referrals alone if you want to build a business that has long-term value and which can operate without you! And remember, if your business can’t operate without you, then it’s a job, not a business. Let’s get to it.

Referrals can win you business. But they don’t create predictable growth.

Most companies rely on referrals because they’ve worked well enough for years. The problem is they’re inconsistent, reactive, and usually tied to the founder’s relationships.

That leaves you with two choices

Stay Referral-Dependent

Win work when it happens to come in
Rely on timing and relationships
Carry growth personally
Deal with an inconsistent pipeline and revenue

Build a Predictable Growth Engine

A business that:

Generates opportunities consistently
Creates predictable recurring revenue
Scales beyond the founder
Increases in long-term value

That’s the difference between a business that creates income… and one that becomes a real asset.

Every Marketplace Is Changing

AI, automation, cybersecurity, and rising client expectations are changing the business landscape fast.

Clients no longer want what they did before. They want certainty, protection, and outcomes.

The companies that are growing the fastest today aren’t relying on referrals alone. They’ve built:

Consistent lead generation
Structured sales processes
Strong client retention systems
Predictable revenue models

What Predictable Growth Actually Requires

Not more hustle.
Not another salesperson.

A scalable sales engine:

Consistent pipeline generation
Structured prospect nurturing
A repeatable sales process
Strong account management and expansion

What Predictable Growth Actually Requires

When those systems are in place, growth stops depending on the founder alone.

That’s the shift. Not sure how to do it?

My Sales Plan Audit is the HOW

Want clarity on what’s holding your business back from predictable growth?

The audit will help you identify

Gaps in your current growth model
What’s limiting pipeline generation
Weaknesses in your sales process
How to build a scalable sales engine that can propel you forward

The Value Gap

James White — Sat, 16 May 2026 07:45:55 +0000

This week, we are going to explore one of the most important factors in why any business buys your service and what you need to do to close the Value Gap. Let’s get to it.

When faced with a decision to buy something, every buyer makes a choice.

And it is a simple one.

Is the product or service I am looking to buy worth the money that the other person or company is charging?

To make this decision, the buyer will consider a number of factors. Here are five of the most important aspects below.

1. What they can physically afford.

Everyone has limits on the money and resources they can access or borrow. We might all want to buy a private jet to take us around the world, but if we don’t have, or can’t borrow, the £50m+ needed to buy or lease the plane, then we can’t buy it. Reality.

2. What they are prepared to spend.

Everyone has their own limits on what they feel comfortable shelling out for a specific item. Whilst some may feel investing over $32m in a giant spider sculpture is good value, others wouldn’t spend that as long as they had breath in their lungs. Beauty is in the eye of the beholder.

3. The extent of the pain and problem they have.

A bottle of water would normally sell for £1 to £2, but if you were walking through a desert without water and needed some to survive, would you spend £20,000 to stay alive? I bet you would. Life with no money is better than money with no life.

4. Their confidence that the solution can solve their current position.

I may be intrigued by a £5,000 tablet that allows me to eat what I want and still lose weight each week, but if I don’t have confidence that it will work and do what it says it will, then I’m not buying.

We covered building belief a few weeks ago. Here is the link if you missed it.

5. The emotional feeling that the end outcome will give them.

Can you put a price on seeing your beloved sports club win a trophy live for the first time in your life, even when the ticket costs thousands of pounds? Many would say, “You bet.” They will always look back and say, “I was there, and that feeling was priceless.”

These (and other factors) contribute to what is known as the “Value Gap”.

The Value Gap is the distance between the buyer’s current position and their desired end position.

If the gap is too large, the buyer stays where they are and the seller loses out.

Sellers will often hear phrases such as:

“I can’t justify spending that amount.”
“We simply don’t have those funds available right now.”
“I like it, but I just don’t like it enough.”
“I just can’t see how it will work for us.”

It’s painful when that happens. All that built-up emotion and energy for the sale just gets lost. But it can AND SHOULD have been avoided.

Your job as a seller is to bridge the gap.

You do that through insight, information and evidence.

But how do you know what they think? And what they really value?

You have to focus on ‘bridging the gap’, but it’s not that easy, I can hear you saying.

You want to understand what the buyer DOES VALUE and how you can take them on a journey they BELIEVE in.

But how??

How can you find out what the buyer REALLY values and what they think to those 5 key points?

By getting inside their mind. By understanding them. By getting to know what makes them tick.

And how do you do that?

By becoming an expert in asking the right questions in the right way at the right time. When you do this, the layers of the onion start to peel away.

If the buyer lets you inside their world or through the layers of their onion,

AND

The buyer truly believes that you are there to help them rather than take advantage of them, then your sales world opens up.

Your Sales Super Power becomes real.

If you want to build the Sales SuperPower, then understand there are levels of questions, and that different questions will need to be used in different scenarios.

First contact outreach
First call
First meeting
Networking meeting
Second call
Demo
Dealing with objections
Closing, etc.

You need ALL of them in your toolbox. Each situation will require a different set of questions.

You must ask questions in the right way, with the right tone and approach to wear the SuperPower cape, though.

We get inside their mind by asking questions, by learning something new about them and their situation.

What concerns them and what excites them?
What worries them and what gives them comfort?
What starts their engines, and what stops them from starting?

The Sales SuperPower comes from listening and asking the right questions.

When we become an EXPERT in asking the right questions, at the right time, in the right way, you can cross the Value GAP in the mind of the buyer, and when you do that, you win business!

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

If not, then what sales question or area would you like me to cover in a future newsletter?

Let me know. I read all replies, even if I don’t have time to reply to them all.

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

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

Knowledge matters…

James White — Sat, 09 May 2026 08:18:43 +0000

In todays edition, we will cover why knowledge of what you sell is vital if you want to really impress those you engage with. And what should you do if you lack knowledge?

It taught me so much

I want to share a story that shaped my approach to sales. At the time, that lesson made me feel one foot tall, but looking back now, it taught me so much.

Around 6 months into my first job after I left university, I was asked to go and present to a group of people who worked for Nokia in Helsinki. I had recently joined a computer networking company called 3Com after university, and I had started working in the product sales team selling SuperStack switches. Our team was responsible for communicating the product’s value and supporting the sales team and partners who implemented these products worldwide.

I was lucky in this role that I got to travel the world, and the 7 years I spent with 3Com taught me so much. But I had to start somewhere.

After getting familiar with the products and learning more about the industry and technology, the team believed I was ready to ‘go out into the field’.

It was my first trip abroad and we were about to launch 2 products, the SuperStack 1100 and 3300. Our team was asked to visit customers and our offices across Europe, and my manager Nick asked me to represent the business in Scandinavia. I was asked to travel to Finland first before heading down to Norway and Sweden to share details of the exciting new products we were launching.

The first presentation was seen as an easy starting point. I was asked by the Country Manager of Finland to give a 1-hour presentation to around 20 technical people who worked at Nokia. They were big users of the earlier version of the product, and the sales team were keen to get them to upgrade, as they were a big customer of 3Com at the time.

To give you some perspective, I had completed a computer systems degree but, being honest, technical systems and products were not my strong point. I was confident, had rehearsed my presentation and learned as much as I could about 10/100 switches, but I was better at the talking part than the technical bit.The day of the presentation came along and I ensured I looked smart. I met Teemu, the Country Manager for Finland, outside my hotel and he drove me to the Nokia office.

Nokia aren’t well known now but back in 1997 they were a BIG deal.

Most of the early mobile phones made were Nokias, and I still love my old Nokia 3310. Ask anyone over 50, these phones were used by everyone!!

Introductions were made and I looked out at the audience of 30-plus (others had joined as they had come to listen to the expert ) engineers and started talking.

It is safe to say that the 60-minute presentation/meeting was one of the longest hours of my life.

I shared what I knew and what I had learned, but what I knew was superficial and basic compared to what 12 network engineers knew about switches. It became clear quite early on that I was a beginner and most of these guys were advanced!

I barely knew what the 7-layer model meant (look it up if you haven’t heard about it, but it’s a bit techie), but they knew all 7 layers and knew more about my product than I did.

Whilst I was able to talk about features at a very top level, they wanted the guts.

Why did you build the feature in that way?

Why does it only support 7 VLANs?

Does it support 802.1 P and Q?

It became clear after a short while that I was out of my depth.

I used my lack of knowledge to go deeper into features which I didn’t know that much about, and that itself made me look even more like an idiot. I read out lines from a product manual whilst these guys were doing the practical implementation daily, which I hadn’t done.

I must have looked at the clock some 30 times during that 1-hour period and every time I looked over at the Country Manager for Finland, I could read his thoughts of, ‘Why have they sent this junior idiot over to me?’

What made it worse was that I didn’t, at this stage, know the best way of handling questions you don’t know the answer to.

Nowadays, when I get asked this, I will respond with, ‘That’s a great question, tell me more about your thoughts here’ or ‘Interesting, what made you ask this?’

Or, if needed, reply with, ‘This is an area I am not totally sure on. I could give you an answer, but I want to ensure it’s correct, so let me come back to you on this.’

This can work with 1 or 2 questions, but if you are continually saying it then there is a problem.

I could have (and maybe should have!) fessed up and said we needed to bring an engineer in to speak with them, but I thought I was the ‘Daddy’ travelling overseas as a 22-year-old and I was schooled. It was a valuable lesson I have learned from ever since.

To make matters worse, the Head of IT at the end of the presentation came out, looked sorry for me and said with a sigh, ‘Sorry about my guys in there, they just thought you knew lots about the devices. Not to worry.’

He felt sorry for me, I could tell, but the Country Manager didn’t. He felt I had cost him a deal and it’s not a surprise that I wasn’t asked to come back!

The moral of the story for me?

Build knowledge of your subject area before you present OR become an expert at asking the right questions to dig deeper into what made the person ask the question in the first place!

But ideally, become an expert in your field. Know what the challenges are in your market. Know what interests people and takes up their time and attention.

Nokia stayed as a customer because 3Com was a big enough company to cope with my average performance that day, but you may not get a second chance in your business.

Get a PhD in your customers’ world and problems. Know more about their space than they do and, if you do, it can allow you to open up strong conversations which build trust, respect and very often lead to new business.

Go in blind and knowing very little and you will look like I did 28 years ago — a novice.

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

If not, then what sales question or area would you like me to cover in a future newsletter?

Let me know. I read all replies even if I don’t have time to reply to them all.

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

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

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.