The First Outreach Message

Apr 04, 2025

 

5 minute read

Okay so picture two single people out there in the world. The classic romantic comedy meet-cute setup. 

Guy bumps into girl, girl drops her stuff, both start to pick the stuff up, each of them apologizing profusely… 

Their eyes meet…

And the guy says…

“Go to dinner with me?” 

Yeah… that wouldn’t work, would it? (I mean, unless you’re suuuper hot

Yet that’s exactly what dozens of recruiters a week are trying to do with hiring managers.

Perfect strangers, bumping into each other online, and without any preamble…

Without any buildup, or any stepping stones…

The recruiter asks for a big commitment. (And yes, a 30 minute “free” call is a big commitment. Hiring managers are busy) 

And this is something that every “How to write the perfect outreach message” article on Google, and every “guru” on LinkedIn seems to be promoting. 

“Just ask enough people to get on a call and eventually one of them will.”

100 people a day. 

1000 people a day.

Whatever it takes to get those 5 calls a week, right? 

Well… I happen to think differently, and if you’re reading this then maybe you do, too. 

Not just because the “ask for a call in the first message” approach is annoying. 

But it’s ineffective. And getting worse by the week. 

So let’s look at a few pitfalls to avoid in this first message and figure out how to send a better one. Sound good? 

3 things we’ll cover that will turn your first message into the beginning of a profitable relationship:

  1. Don’t try to do too much
  2. Don’t forget the basic ways humans interact
  3. Don’t burn a bridge because someone’s not ready

Don’t try to do too much

You might be the perfect recruiter for your prospects. 

But they don’t know that yet. 

You need to deliberately walk them through your sales process so they can find out. 

But an outreach message that asks someone to get on a call in the very first message… Or the very first cold email… Or the very first cold call… 

It’s trying to do too much. 

Yes, getting a prospect onto that discovery call so you can close them *is* the end goal. 

But that goal is down the road. 

It’s like asking that attractive person out to dinner as soon as you open your mouth. 

Instead you’ve got to have a conversation. See if there’s any sort of connection at all. Suss out whether they’re single & open to getting to know you more… and then you can suggest dinner. 

It’s not different in business.

Prospects need to know a little bit about you before they’ll commit to a call. Even a short call. 

They need to like you a bit. Or at least believe you can help them do something they need. 

And they need to trust that you’re not going to waste their time. 

Now in the world of recruiting sales, you’re building this know, like, trust factor through the conversation you’re having. 

And the first message will almost never achieve all three & then slam dunk a call booking. 

But it can start the conversation. Where you can then build enough rapport for someone to consider getting on a call with you. 

So the first message isn’t about booking a call at all. 

It’s about getting a response. Any response.

And once you’re talking… You can steer the conversation in the right direction. 

How do you do this?

Don’t try to describe your service, assume things about your prospect, build rapport, *and* ask for something all in one message. 

Just start the conversation. I’m a fan of using questions for this. For example: 

“Several of our clients had success with XYZ last month. Is this something you’ve seen?” 

Or

“Hey I noticed you’re based in _____, I visited last year & loved it. How long have you been there?” 

You’re having a conversation. Breaking the ice. Not “booking a call” 

Which brings us to our second point: 

Don’t forget the basic ways humans interact

Ever go to an in-person networking event? One of my first jobs after college was putting on cocktail hours, golf tourneys, etc for a business association in San Francisco. 

And I noticed that the most successful people…

The presidents. The business owners. The partners. 

They weren’t pitching. They weren’t asking for business meetings. 

They were just chatting. Talking about traffic. (Bay Area… IYKYK) Talking about their vacations. Finding common ground. 

The hungry 23 year olds like me were trying to muscle our way into conversations and “talk business,” delivering pre-rehearsed pitches. 

But that’s not really how normal people interact. 

They talk about this and that. Common things. Interesting things. 

And eventually the conversation can move toward business. But jumping right into a pitch just makes you look desperate, inexperienced, and tone-deaf. 

**It’s not any different online**

Just because you’re meeting people at the virtual, 24/7 networking event that is LinkedIn doesn’t mean that those people are excited to hear a sales pitch from a perfect stranger they’ve never interacted with before. 

Those little profile pictures represent real people. 

And real people don’t come to networking events to hear a dozen sales pitches a day. But they do like to meet people. People who they might someday do business with. 
And one of those people could be you. 

So don’t hurry too much to get to the pitch. Remember that you’re talking to a person, not just a prospect. And have a conversation before you start spouting off about how amazing your results are and stuff like that. 

Because there’s one more big reason to avoid pitching immediately.

Don’t burn a bridge because somebody’s not ready

No matter how meticulous you are about building your prospect list, most of the people on it simply don’t need you right now. 

But that doesn’t mean they’ll never need you. 

Maybe next month. 

Maybe next year. 

I’ve had people know me, follow me online, & chit chat with me for 3 years before we decided to work together. 

But if you take the lazy route of Connect>>>Pitch>>>Appointment…

Then you’ll all but guarantee that the 95% of hiring managers who don’t need you now… will decide to **never** work with you. 

It’s the difference between trying to start a transaction and trying to start a relationship. 

When you’re going after a transaction, there are only two real options: either the prospect buys or doesn’t buy. 

And the people who don’t buy disappear forever. 

But when you’re going after a relationship, your options open up significantly. 

Some of those people will be ready to buy, and they’ll appreciate you taking the time to get to know them a bit before pitching them. 

Others won’t need to buy right now, but if you have a good conversation and are organized, then you can hit them up in a month or three to check in. 

Still others will be excited to read your content, watch your videos, & listen to your audios, getting to know you the whole time. 

These people will keep you in mind for when they do need your services… And they’ll also be much more likely to recommend you to anyone they know who could benefit from working with you. 

How likely are any of those outcomes from someone you annoyed by asking for a call before you knew anything about them? 

So when you’re doing cold outreach, don’t focus so much on the transaction. Focus on the relationship. 

It might take a little longer. But it will last a lot longer, too.  

Conclusion

That first impression is crucial. 

Don’t throw it away by doing what so many less-skilled-than-you recruiters are doing: 

***Jumping straight to an annoying cold pitch***

So remember these three things when you’re crafting that cold outreach message: 

  1. Don’t try to do too much
  2. Don’t forget the basic ways humans interact
  3. Don’t burn a bridge because someone’s not ready

And take some of the pressure off of that first message. Don’t try to book a call immediately. 

Just start a conversation. Try it this way & watch your reply rates go up, and after having a few of these conversations, watch your number of booked calls go up, too.

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