How to Close Six-Figure Sales Deals with Strategic Preparation

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Most salespeople lose big deals before they even get on the call.

They think they’re losing because they didn’t handle objections well enough. Or because they didn’t create enough urgency. Or because the prospect “just wasn’t ready.”

But that’s not what’s happening.

They’re losing because they showed up unprepared. They tried to wing it. Research shows that most B2B sales involve 6-10 decision-makers, with engaging multiple stakeholders raising deal close rates by up to 30%. They relied on charisma and pressure tactics instead of doing the actual work that closes deals.

Here’s the truth: the bigger the deal, the less pressure works. And the more preparation matters.

I’ve closed deals ranging from $10K to $500K+. Industry data shows that the average sales close rate for high-ticket deals in 2024 was 29%, highlighting how challenging these complex sales can be. And I can tell you right now, the six-figure deals never close because you pushed harder. They close because you prepared better.

Let me show you exactly what that preparation looks like.

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Why High-Pressure Sales Tactics Fail for Six-Figure Deals

Let’s start with why the traditional “high-pressure” sales approach falls apart when you’re selling big tickets.

When you’re selling something for $500 or $2,000, pressure tactics can work. Scarcity. Urgency. “This offer expires tonight.” “Only 3 spots left.”

The buyer doesn’t have much to lose. The decision is relatively low-risk. A little pressure might be the push they need to take action.

But when you’re selling something for $50K or $100K or $500K, everything changes.

At that price point, the buyer has a lot to lose. This is a business-critical decision. There are multiple stakeholders involved. There’s board approval. There’s budget allocation. There’s implementation risk.

And when you try to pressure someone into a decision that big, you know what happens?

They shut down. They pull back. They say they need more time. They ghost you.

Because pressure at that level feels manipulative. It feels like you’re trying to rush them into something they’re not ready for. And people with big budgets don’t respond well to manipulation.

They respond to preparation.

What Real Sales Preparation Looks Like for Big Deals

Most people think preparation means having a good pitch deck. Or knowing your talking points. Or being ready to handle objections.

That’s not preparation. That’s basic sales hygiene.

Real preparation means you’ve done so much research and pre-work that by the time you get on the call, you already know. Studies show that 44% of sales professionals rank phone calls as the most effective way to close deals, making proper preparation for these conversations critical.
You need to know:

• Exactly what their problem is
• Why they haven’t solved it yet
• What a solution would be worth to them
• Who else needs to be involved in the decision
• What their buying process looks like
• What objections they’re likely to have
• How to position your solution as the obvious choice

You’re not discovering this stuff on the call. You already know it before you dial.

And when you show up with that level of preparation, you don’t need to pressure anyone. The deal closes itself.

Five-Step Pre-Call Research Framework for Closing Bigger Deals

Here’s what I do before every big deal call. And I mean every single one.

This isn’t optional. This is the difference between closing at 20% and closing at 60%+.

Step 1: Deep dive on the company

I’m not talking about reading their About page. I’m talking about understanding their business model, their revenue, their growth trajectory, their challenges.

I look at:

• Their financials if they’re public
• Recent news articles or press releases
• LinkedIn posts from their executives
• Customer reviews and complaints
• Competitor analysis
• Industry trends affecting them

I want to understand their business better than 95% of the vendors they talk to.

Step 2: Map the decision-making unit

Who’s actually involved in this decision? It’s never just one person for big deals.

I identify:

• The economic buyer (who controls the budget)
• The champion (who’s pushing for this internally)
• The technical evaluator (who’s assessing feasibility)
• The end users (who will actually use the solution)
• Any potential blockers (who might oppose this)

I look them up on LinkedIn. I read their posts. I understand their priorities and concerns.

Step 3: Understand their current state

What are they doing now? Why isn’t it working? What’s the cost of the status quo?

I try to quantify this. If they’re wasting $200K/year on an inefficient process, I need to know that number before the call.

If they’re losing customers because of a broken experience, I need to understand the customer lifetime value they’re losing.

Numbers matter. Vague problems don’t close deals. Quantified problems do.

Step 4: Research their past buying behavior

What tools are they already using? What vendors have they bought from before? What does their tech stack look like?

This tells me:

• What their buying process probably looks like
• What they value in a vendor
• What price points they’re comfortable with
• What integrations matter to them

I use tools like BuiltWith, Crunchbase, LinkedIn Sales Navigator. Whatever it takes to get this intel.

Step 5: Identify likely objections

Based on everything I’ve learned, what objections will they probably raise?

I write them down. I prepare answers. I gather proof points and case studies that address each one.

I’m not waiting for the objection to come up on the call and then scrambling to respond. I’ve already thought through my response.

This entire research process takes 1-2 hours for a potential six-figure deal.

Most salespeople won’t do it. They think it’s too much work. They’d rather just “get on a call and see what happens.”

And that’s why they lose.

How to Create a Pre-Call Planning Document That Closes Deals

Once I’ve done my research, I create a planning document for the call.

This is for me. Not for the prospect. It’s my game plan.

Here’s what’s in it:

Their situation (as I understand it)

• Current challenges
• Cost of inaction
• Desired future state
• Timeline pressure (if any)

Key stakeholders

• Names, titles, roles in the decision
• Individual priorities and concerns
• Relationships between them

Our positioning

• Why we’re uniquely positioned to solve this
• Proof points and case studies to reference
• Differentiators vs competitors they’re likely considering

Call objectives

• What needs to happen on this call for it to be successful
• What questions I need to ask
• What information I need to uncover
• What commitment I’m asking for at the end

Anticipated objections and responses

• List of likely objections
• Prepared responses with proof points
• Questions to ask instead of defending

This document is usually 2-3 pages. I review it right before the call. Sometimes I have it open during the call as a reference.

It means I’m never caught off guard. I’m never scrambling. I’m always three steps ahead.

How to Open a High-Value Sales Call Like a Pro

The first 5 minutes of a big deal call set the tone for everything that follows.

Most salespeople open with small talk, then launch into their pitch. “So, tell me about your business. What challenges are you facing?”

That’s lazy. And it signals that you didn’t do any homework.

Here’s how I open:

“Hey [Name], thanks for taking the time today. Before we dive in, I want to make sure I’m not wasting your time. I did some research on [Company] and from what I can see, you’re dealing with [specific challenge]. Is that accurate, or am I off base?”

This does three things:

1. It shows I did my homework
2. It demonstrates I understand their business
3. It gives them a chance to correct me or add context

Then I follow with:

“Based on what I’ve learned, I think we might be able to help with [specific outcome], but I want to ask you some questions first to make sure this is actually a fit. Sound good?”

Now I’m positioned as a consultant, not a salesperson. I’m there to diagnose, not pitch.

And because I’ve done my research, I’m asking smart questions that drill into the real issues.

Not generic discovery questions. Specific, informed questions based on what I already know.

Strategic Sales Questions That Uncover Decision-Making Insights

Here’s where preparation really pays off.

Instead of asking surface-level questions like “What keeps you up at night?” or “What are your biggest challenges?” – I’m asking questions that dig into specifics.

Questions about quantification:

• “You mentioned [problem]. What’s that costing you annually?”
• “If we could solve [specific issue], what would that be worth in terms of revenue/savings/efficiency?”
• “What’s the cost of not solving this in the next 6-12 months?”

Questions about decision process:

• “Walk me through what needs to happen internally for a decision like this.”
• “Who else needs to be involved in evaluating this?”
• “What does approval look like? Single decision maker or committee?”

Questions about past attempts:

• “Have you tried to solve this before? What happened?”
• “What didn’t work about previous solutions you’ve tried?”
• “What would need to be different this time for it to work?”

Questions about timeline:

• “What’s driving the timeline on this?”
• “What happens if this doesn’t get solved this quarter/year?”
• “Is there a specific event or deadline that’s creating urgency?”

Questions about competition:

• “Who else are you looking at for this?”
• “What do you like about what they’re offering?”
• “What concerns do you have about going with them?”

These questions accomplish two things:

First, they uncover information I need to close the deal effectively.

Second, they position me as someone who thinks strategically about their business, not just someone trying to sell them something.

How to Build Your Sales Case During Discovery Calls

As they answer your questions, you’re building your case in real time.

You’re not pitching yet. You’re listening. You’re taking notes. You’re asking follow-up questions.

And in your head (or in your notes), you’re connecting the dots:

“Okay, they’re losing $300K/year on this problem. Our solution costs $100K. That’s a 3x ROI in year one. That’s my anchor number.”

“They tried a competitor 2 years ago and it failed because of [reason]. Our approach specifically addresses that. That’s a key differentiator.”

“The CFO needs to approve anything over $50K. I need to position this in terms of cost savings and ROI, not just features and benefits.”

By the time you’re ready to present your solution, you already know exactly how to frame it for maximum impact.

How to Structure Your Sales Pitch for Maximum Impact

Most salespeople think the pitch is where the magic happens.

It’s not. If you’ve done the preparation right, the pitch is just confirming what they already know.

Here’s how I structure it:

“Based on what you’ve told me, here’s what I’m hearing…”

I summarize their situation back to them. Their challenges, the cost, the urgency, the desired outcome.

This does two things: it shows I was listening, and it gets them nodding in agreement.

“Here’s how we’ve solved this exact problem for companies like yours…”

I reference a specific case study. Not generic. Specific. Same industry or same problem or same size company.

I walk through:

• Where that company was (similar to where they are)
• What we did
• What the results were (quantified)
• How long it took

“Here’s what this would look like for you…”

I don’t pitch features. I pitch outcomes. Specific, quantified outcomes based on what they told me.

“Based on the $300K you’re currently losing annually, and based on what we’ve achieved with similar clients, I’d expect we could cut that loss by 70-80% within 90 days. That’s roughly $210K-$240K in savings in the first year.”

See how that’s different from “Here are our features and pricing”?

“Here’s what the process looks like…”

I walk them through implementation. Timeline. What we need from them. What they can expect from us.

This addresses the “how hard is this going to be” concern before they even ask.

“And here’s the investment…”

I present pricing in context. Not just “$100K” but “$100K to solve a $300K problem, with ROI in the first 90 days.”

I anchor the price to the value. I show them it’s not a cost, it’s an investment.

How to Handle Sales Objections When You’ve Done Your Research

Here’s where preparation really shines.

When an objection comes up, I’m not caught off guard. I already anticipated it. I already prepared for it.

“That’s more than we budgeted.”

I already know their revenue. I already know the cost of their problem. I already have ROI numbers ready.

“I understand. A lot of our clients said the same thing initially. But when we looked at the numbers – you’re currently losing $300K a year on this. We’re talking about a $100K investment that saves you $240K in year one. From a CFO perspective, that’s a no-brainer investment. Have you run those numbers internally?”

“We need to see a demo first.”

I already have a demo ready. But I don’t just show features.

“Absolutely. Before I show you anything, let me make sure I’m showing you the right things. You mentioned [specific challenge]. Let me show you exactly how we solve that…”

Then I customize the demo based on what they told me matters.

“We need to get approval from [person].”

I already knew that from my research. I’m prepared for it.

“Makes sense. What information would you need from me to take to [person] to make that case? Would it help if I joined a call with them to walk through the ROI?”

See how this works? I’m not scrambling. I’m not defensive. I’m prepared.

How to Close Big Deals Without Pressure Tactics

Here’s the thing about big deals when you’ve prepared well: you rarely need to “close” in the traditional sense.

You’ve already established:

• Their problem is real and expensive
• Your solution solves it with proof
• The ROI is obvious
• The implementation is manageable
• You’ve addressed their objections

At that point, the close is just about logistics.

“So here’s what I’m thinking. Based on everything we’ve discussed, this seems like a strong fit. What would need to happen on your end to move forward?”

Then you shut up and listen.

They’ll tell you exactly what needs to happen. Who needs to approve it. What timeline they’re working with. What concerns still need to be addressed.

And because you’re prepared, you can address all of that.

“Okay, so you need CFO approval and you need to run this by your implementation team. How about this: I’ll put together a one-page ROI summary you can take to your CFO, and I’ll set up a 30-minute technical call with your implementation team to address their questions. Can we schedule both of those this week?”

You’re not pressuring. You’re facilitating. You’re making it easy for them to say yes.

Post-Call Follow-Up Strategy That Moves Deals Forward

Preparation doesn’t end when the call ends.

Most salespeople send a generic “thanks for your time” email with a calendar link or proposal attached.

That’s not follow-through. That’s just checking a box.

Here’s what I do:

Within 2 hours of the call, I send an email that includes:

A summary of what we discussed

• Their key challenges (in their words)
• What they’re looking for in a solution
• Their timeline and decision process

Specific next steps

• What I committed to doing
• What they committed to doing
• Specific dates/deadlines for each

Relevant proof points

• Case studies I mentioned
• ROI calculations specific to them
• Any resources that address their concerns

A clear ask

• What I need from them to move forward
• When I’ll follow up if I don’t hear back

This email is customized to them. It references specific things they said. It shows I was listening and I’m on top of things.

And because I prepared well for the call, writing this email takes 15 minutes. Because I already have all the information and all the assets ready.

Why Preparation-Based Selling Closes More Six-Figure Deals

Let me explain why this preparation-based approach closes bigger deals than pressure ever will.

It builds trust

When you show up prepared, the prospect knows you’re serious. You’re not just trying to hit quota. You’re actually trying to solve their problem.

Trust closes deals. Pressure destroys trust.

It positions you as a peer

You’re not a salesperson begging for their business. You’re a strategic partner who understands their business and can help them solve a real problem.

Decision-makers buy from peers, not from vendors.

It shortens the sales cycle

Ironically, spending more time on preparation actually speeds up the sale. Because you’re asking the right questions, addressing the right concerns, and moving the deal forward efficiently.

Pressure tactics drag things out because the prospect keeps stalling.

It increases deal size

When you understand their problem deeply and can quantify the value of solving it, you can charge accordingly.

You’re not competing on price. You’re competing on value. And preparation lets you demonstrate that value clearly.

It improves close rates

I’ve tracked this. My close rate on deals where I do this level of preparation is 3x higher than deals where I wing it.

3x. That’s not a small difference.

Sales Call Preparation Template and Checklist

Let me give you a template you can use for your next big deal.

Pre-Call Research Checklist: □ Company financials/revenue (if available) □ Recent news or press releases □ Executive LinkedIn profiles reviewed □ Current tech stack identified □ Competitors they’re likely considering □ Decision-making unit mapped □ Quantified cost of their problem □ 3 likely objections identified □ Relevant case studies selected

Call Planning Document:

• Current situation summary (2-3 sentences)
• Key stakeholders and their roles
• Top 3 questions to ask
• Positioning statement (why us)
• ROI anchor number
• Call objective and desired next step

Post-Call Follow-Up:

• Summary of discussion
• Specific next steps with dates
• Relevant proof points attached
• Clear ask

Copy this template. Use it for every deal over $10K. I guarantee your close rate will improve.

Five Sales Preparation Mistakes That Kill Big Deals

Let me save you some time by pointing out the mistakes I see people make when they try to implement this.

Mistake #1: Doing surface-level research

Looking at someone’s website and LinkedIn profile isn’t enough. You need to go deeper. Read their reviews. Check their financials. Understand their market.

If your research doesn’t give you insights you can use on the call, you haven’t researched enough.

Mistake #2: Not customizing your approach

Just because you prepared doesn’t mean you should dump all your research on them. Use what’s relevant. Follow their lead. Be conversational.

The preparation is for you, not to show off to them.

Mistake #3: Preparing but not practicing

Don’t just research and write a document. Actually practice your opening. Practice your questions. Practice your pitch.

If you sound robotic because you’re reading from a script, preparation won’t help you.

Mistake #4: Over-preparing on features, under-preparing on value

Don’t spend all your time memorizing product details. Spend your time understanding their business and how to quantify the value you deliver.

Features don’t close deals. Value does.

Mistake #5: Not adapting based on what you learn

Your preparation is your starting point, not your script. If they tell you something that contradicts what you researched, believe them and adapt.

Rigid preparation is almost as bad as no preparation.

How to Scale Your Sales Preparation Process for Multiple Deals

“But Jeremy, I can’t spend 2 hours preparing for every single call. I’ve got too many deals in my pipeline.”

Fair point. Let me address that.

First, this level of preparation is for big deals. Six figures and up. If you’re selling $2K packages, this is overkill.

But for big deals? 2 hours of prep for a $100K opportunity is a no-brainer investment.

Second, you can systematize parts of this. Create templates. Build a research process. Use tools to speed up the intel gathering.

Over time, you’ll get faster at it. What takes 2 hours now will take 45 minutes in a few months.

Third, qualify harder. If you’re spending this much time on preparation, make sure the deal is real. Don’t waste prep time on tire-kickers.

And finally, hire support. If you’re closing enough big deals, hire a sales engineer or an SDR who can do some of the research legwork for you.

Your time is best spent on the actual calls and the strategic thinking. The research can be delegated once you have the process dialed in.

Four-Week Plan to Implement Preparation-Based Selling

If you’re currently trying to close big deals with charisma and pressure instead of preparation, here’s how to make the shift.

This week: Pick your biggest active opportunity. Do the full research process I outlined. Create the planning document. Prepare like you’ve never prepared before.

Next week: Get on the call with that preparation. Notice how different it feels. Notice how the conversation flows. Notice how much more confident you are.

Week 3-4: Implement this for every deal over $25K in your pipeline. Track your results. Compare your close rate to your previous approach.

I’m willing to bet your close rate goes up by at least 50%. Probably more.

Because at the end of the day, people don’t buy from the best presenter or the pushiest salesperson.

They buy from the person who clearly understands their problem and can confidently solve it.

And the only way to get there is preparation.

Not pressure. Preparation.

Most business owners waste years figuring out what actually works. In my Master Internet Marketing program, I compress that learning curve into 7 weeks — covering copywriting, funnels, ads, and more. If you’re ready to invest $5k and get serious about your skills, apply here.

Now go pick your biggest deal and start doing the research. You’ve got work to do.