Writing Outreach One Person at a Time Changed How I Describe My Work

Ok, I admit it. I’m becoming one of those LinkedIn DM outreach people.

It feels weird, and I put it off for as long as I could. For about a month I did a little of it, but nowhere near enough. Now my growth advisor has me report to him every day on how many people I reached out to, how many calls I booked, and which part of my audience they came from. If I want to hit the goal I said I wanted, that’s what it takes.

So I’m doing it, slowly and on purpose, one person at a time, and every message is written for the person getting it. The response has been great. At one point I’d booked eight calls in a couple of days and offered a call to about three times that many people, and my calendar is full of holds.

What I didn’t expect was how much it would change the way I describe my work. 33 messages in, saying it over and over has made it feel a lot more like me.

A sentence on a website never gets tested

I’ve written positioning for my own business more times than I’d like to admit. Homepage copy, a LinkedIn headline, an About section. Every one of those got drafted, edited, and shipped, and none of them ever had to survive a specific person reading it.

A DM is different. When I write to an agency owner, I’m picturing that owner, their agency, and what their week probably looks like. Then I have to describe what I do in a sentence or two that makes sense to them. If the sentence is vague, I can feel it while I’m typing, because I know they’ll read it and have no idea what I’d do for them.

When I started, I thought my angle was interesting, but I wasn’t totally sure about it. Writing it fresh for each person forced me to look at it from a lot of different directions. How would a finance person read this? What about an owner who’s never thought about delivery as a separate thing from sales? I’d tweak a word, try a different order, and notice which version I could say without it sounding like a tagline.

Watching the line change in three days

On the first day, the line I sent owners was “I’ve been consulting with agencies on their delivery operations, making sure their services run great, get results, and are profitable.”

By the next day it had picked up something I’d been leaving out: “I’ve focused my agency consulting solely on delivery operations, helping agencies make sure their services keep running great, get results, and stay profitable in the age of AI.”

Neither of those is bad. But neither of them says what I do on a Tuesday. Here’s where it’s landed for now:

Every agency is working on bringing more revenue in. I work on how much of it they keep. I go into an agency one team and one process at a time, crack open how the client work gets delivered, figure out where AI helps and where it doesn’t, and rebuild it with the people doing the work. The point is for the team to do more of the work they love, and for the agency to make more money doing it.

That version names the actual move. One team, one process, the people doing the work. I don’t think I would have gotten there by sitting down to write a positioning statement. I got there by saying it to one person at a time and keeping what held up.

The question that didn’t work

The other thing outreach taught me fast was which questions get a real answer.

My first instinct was to ask owners some version of “have your services kept up?” It sounded like a good question to me. The problem is that owners believe in their agency. Of course they do. Ask them whether their services have kept up, and the honest answer they’ll give you is “we’re strong.”

That answer is true, and it also ends the conversation. So I switched to asking about one service line: “Is there a service line or workflow where you could use a second set of eyes or support?” An owner who’d never say their agency has fallen behind can usually name the one service that’s been bugging them. That’s a conversation I can have, and it’s where my work starts anyway.

I wouldn’t have learned that from a website. Nobody writes back to a homepage to tell you the question was wrong.

“Isn’t this just spam with better manners?”

I had the same reaction, which is a big part of why I put it off. A lot of DM outreach is a template with a first name dropped in, and nobody answers those.

The difference, as far as I can tell, is whether the message could have been sent to anyone else. If I can swap out the name and send it to the next person on a list, it’s spam. If it only makes sense for the person reading it, because it’s about their agency or something they posted or the last time we talked, then it’s a note from someone who wants to talk to them.

That takes a lot longer. 33 messages is a small number by outreach standards, and I’m fine with that.

There were moments in the first few days where I asked myself whether I really wanted the goal I’d set, and whether I wanted to be doing this work at all. I’m still giving it a real try. Seeing who writes back and getting the whole thing moving has been more interesting than I expected.

The line I’ve got now will probably change again before the month is out, and that’s fine. It already sounds more like me than anything I wrote for the website.