How to understand what your prospects are thinking (and why most outreach gets it wrong)

The people you want to do business with are being bombarded. Copy-and-paste emails, poorly written LinkedIn DMs, requests that make no sense from people they've never heard of. Every single day.

So when you reach out, you're not just competing with your direct competitors. You're competing with every other person who's already wasted five minutes of your prospect's morning.

Here's a real example that landed in my inbox recently. Someone asked for a 60-minute meeting - to discuss having a meeting the following week. I'd never spoken to this person before. They also claimed they could offer exposure to 100,000 people. When I checked their LinkedIn profile, they had 500 followers.

There's a lot to unpack there.

What that example tells us about how not to sell

Every bad piece of outreach has the same problem underneath it: the person sending it hasn't stopped to think about the person receiving it. Here's what I mean, broken down.

Understand how businesses actually operate

Asking a stranger for an hour of their time to discuss having another meeting is not how business works. Decision-makers are stretched. Their calendars are full. Every request for time needs to earn its place, and a 60-minute speculative call from someone they've never met does not earn its place.

Before you reach out, think about what you're actually asking for and whether it's proportionate to the relationship you have with that person. Which, if you've never spoken before, is no relationship at all.

Respect how busy people are

Last-minute requests signal one thing clearly: you haven't thought about the other person's schedule, only your own. Busy people plan their weeks in advance. Dropping into someone's inbox and expecting them to carve out time at 24 hours' notice tells them immediately that you don't understand how they operate.

Give people enough notice. If you can't, acknowledge it and ask if there's a time that works for them rather than assuming they'll rearrange their day for you.

Get your numbers right

Claiming 100,000 when you have 500 is not a rounding error. It's the kind of claim that takes about 30 seconds to disprove and destroys any trust you might have built. Prospects do their homework. They check. And when the numbers don't add up, neither does anything else you've said.

If your numbers are modest, own them. Credibility built on accurate information lasts. Credibility built on exaggeration lasts until someone looks you up.

Stop exaggerating and start being authentic

Bragging has never been less effective than it is right now. People are tired of inflated claims, manufactured social proof, and profiles that read like a press release. What they respond to is honesty - someone who knows what they're good at, is clear about it, and doesn't need to dress it up.

Authenticity isn't a soft concept. It's a commercial advantage. The more specific and honest you are about what you do and who you help, the easier it is for the right people to recognise themselves in what you're saying.

Do the work properly

Sales is not a quick fix. It never has been. The people who treat it like one - firing off the same message to hundreds of contacts and hoping something lands - are the same people who wonder why nothing is working.

Getting the foundations right takes time. Understanding your prospect, crafting a message that's relevant to them, following up properly, building a relationship before you ask for anything - none of that is glamorous, but all of it works. How to follow up effectively in sales is one of the things I cover in detail here.

Make sure what you say is what they actually hear

This one is easy to miss. The language that makes sense in your world doesn't always land the same way in your prospect's world. Jargon, assumptions, phrases that mean something specific in your sector - all of it can create distance between you and the person you're trying to reach.

Before you send anything, read it back as if you're the person receiving it. Does it make sense to someone who doesn't know your business? Does it answer the question they're actually asking, which is "why should I care about this?"

What your prospects are actually dealing with every day

It's worth pausing to think about the reality of being on the receiving end. A typical sales director or business owner might receive dozens of unsolicited messages in a week - emails, LinkedIn DMs, connection requests with a pitch already attached. Most of them get deleted without being read properly.

The ones that don't get deleted are the ones that feel like they were written for that specific person. That means doing research, referencing something relevant to their business, and asking for something proportionate to the relationship you actually have with them.

How to think like your prospect before you reach out

Before you write anything, ask yourself these questions honestly. They'll save you a lot of wasted effort.

• Do they know who I am? If not, how am I establishing enough credibility to make them want to keep reading?
• What's actually in it for them? Not for me - for them, specifically.
• Am I asking for too much too soon? A 30-minute call is a much easier yes than an hour. A quick question is easier than a call.
• Is my timing right? Have I given them enough notice? Is this a sensible time of the week or month to be reaching out?
• Does what I've written match how they talk about their own problems? Or am I using my language rather than theirs?

If you can't answer all of those confidently, the message isn't ready to send.

What good outreach looks like by comparison

Good outreach is specific. It references something real about the person or their business. It asks for something small and reasonable. It makes it easy to say yes, and easy to say no without awkwardness.

It also sounds like it was written by a human being who spent five minutes thinking about the person they were writing to - not generated in 30 seconds and fired off to 200 people at once.

The bar isn't actually that high. Most outreach is so generic that a little genuine effort stands out immediately.

If you want to work on how you and your team approach prospects - the messaging, the mindset, and the process - take a look at my sales training or get in touch to have a conversation about what would help most.