Hello Reader,

This week, I want to tackle one of the most common challenges in sales. One that nearly every salesperson will face at some point:

Booking first meetings with prospects.

Recently, Matthew, a person working in sales, reached out to me on LinkedIn and shared his struggle about booking meetings, stating that booking first meetings with prospects is the biggest challenge.

And here’s the truth: Mathew’s experience isn’t unique.

If you’re reading this and thinking, “That’s me too,” don’t beat yourself up. Even the world’s best salespeople rarely achieve more than a 10 - 15% conversion rate when booking initial meetings. It’s tough because a prospect’s time is their most valuable asset.

So how do you convince someone to give you that time, even if they don’t know you?

Here’s the key: you need to bridge the “value gap.”

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Why Prospects Say No

It’s easy to assume a lack of interest means your product or service isn’t good enough, or that they don’t like you. But that’s rarely the case.

The reality is they simply don’t see enough value in spending their time with you - yet.

So you need to think of it like this: If a prospect had a massive problem and knew you could solve it, wouldn’t they be eager to meet? Of course, they would.

The challenge then, is building enough trust and proving your value upfront to make them curious.

This is where you bridge the “value gap.”

Let’s look at how we can do that.

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Step 1: Share Value Before You Ask for a Meeting

The biggest mistake salespeople make is asking for a prospect’s time before proving they’re worth it. Instead, focus on giving value first.

Here’s how:

Research their industry and role: What challenges are people in their position facing right now? Is there a specific trend, regulation, or pain point you can address?

Share something helpful: Offer a resource, tip, or insight that directly relates to those challenges. Show them you’re invested in solving problems, not just selling your product.

Personalise your outreach: A generic message will almost always get ignored. Tailor your communication to make it clear you’ve done your homework.

For example:

Instead of saying, “Hi, I’d like to discuss our product with you,”

Try saying, “I know many directors in your industry are struggling with [specific issue]. I wanted to share a resource with you that’s helped others in your industry.”

When you offer something useful without expecting anything in return, you’re no longer “just another salesperson.” You’re a problem-solver.

Step 2: Build trust through consistency

Booking meetings is never a one-and-done effort. It takes consistent follow-ups to stay on a prospect’s radar.

Here’s what I recommend:

Pick 30 prospects you’d love to meet.

Plan 10 - 15 touchpoints over the next 8 - 12 weeks.

Use a mix of emails, calls, social messages, and even personalised videos.

Every touchpoint should offer value, not just another “Hey, checking in!” message.

For example:

• Share a relevant article or insight about their industry.
• Reference a recent trend or regulation they might be concerned about.
• Send a short personalised video addressing their specific challenges.
• Pro tip: If you’re in this for the long game, map out a multi-week engagement plan.

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Step 3: Derisk - Make It Easy for Them to Say Yes

Prospects often avoid meetings because they assume they’ll be sold to. Reframe the conversation to remove that pressure.

Try saying something like:

"We might not be a good fit, but I’d love to share a few ideas that could help with [specific problem]. If nothing else, you’ll walk away with some useful insights.”

When you position the meeting as a low-risk opportunity to learn (not a high-pressure sales pitch) you’ll dramatically increase your chances of getting a “yes.”

Because they’re no longer committing to a hard sell, they’re simply exploring a conversation.

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Step 4: Make Them Curious About You

If you can leave your prospect thinking, “I want to know more about this person and how they can help,” you’ve won half the battle.

For instance, to spark curiosity, you could say:

"I recently worked with two organisations similar to yours and helped them reduce [specific problem] by [specific amount]. I’d be happy to share how we approached it."

When you personalise your outreach and show genuine interest, you stand out.

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Bonus: Persistence Is Key

The truth is that most sales happen after multiple touchpoints. If you stop after one or two messages, you’re leaving opportunities on the table.

When you’re patient, consistent, and persistent with value, your chances of booking first meetings increase dramatically.

But remember: the real magic happens when you have a genuine desire to help.

Until next week, keep smiling and stay focused on becoming the go-to problem-solver for your prospects.

James

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