What the Subject Line Is

I spent Saturday morning writing an email I did not send. The subject line is where I found out what I have actually been avoiding.

Leigh Sutton
Leigh Sutton Corporate lifer. Aspiring free agent. 5 min read
A warm, inviting home office workspace with a coffee cup, laptop, and notepad on a wooden table.
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I sat down Saturday morning to write the email.

Not to send it. I am aware of the gap between those two things and I have been living in it for two weeks. But I thought: you can at least write a draft. You can open a compose window and see what it says. The calls are not calls you have to make from the office. Start there.

I opened a compose window and typed the name. One of the four non-contingent contacts, someone I have known for 12 years, a relationship I built on my own before I ever worked at this company. She runs operations at a mid-size software company, recently promoted to VP, the kind of role where you are suddenly responsible for renewals at a volume you have never managed before. I know exactly what problem she is having, or going to have. I have watched this problem develop in seven different organizations.

I put her name in the To field.

Then I went to the subject line.


This is where I stopped for forty minutes.

I tried Staying connected, which is what a person writes when they want something but do not want to name it. I tried Quick question for you, which is the same problem plus a lie, because I do not have a quick question. I tried Catching up, except that we have not spoken in two and a half years and this is not catching up, it is the other thing.

Then I tried Renewal consulting – interested in connecting? which read like a cold sales email. Which is technically what it is, except that we have a history and I was hoping history would do some of the work.

I closed the draft and went to get more coffee.

I stood at the counter and thought about what I would say if she called me right now and said: Leigh, I have a problem, one of my biggest accounts is up for renewal in forty days and the relationship is shaky. Actually, that is not quite the right framing. I did not think clearly. I stood at the counter and argued with myself about the email for six minutes while the coffee got cold, which is a different thing.

But here is what I would say if she called. I would say: let me see the account history for the last six months. Get me on a call with your account manager. There are four specific things that typically happen in the last 60 days before a company loses an account, and based on what you just described you are in the middle of two of them.

I would say it in those words and I would mean every one of them.


The email problem, I think, is that I have been writing it in the wrong person.

I keep writing I am a renewal consultant. Or: I have 24 years of enterprise account experience. Or: I’m exploring consulting opportunities and wanted to reconnect.

All of those sentences are about me. What I know, what I can do, what I am hoping she will want to purchase. The honest version of that last one.

The only subject line that actually works is about her.

Are you losing an account right now?

That is the question. That has always been the question. The problem I solve is not abstract. It has a specific shape, a specific timeline, a specific set of signals that most people miss because they are still managing the relationship instead of reading it. She will recognize those signals or she won’t, and if she does, she already knows she needs help, and the email will be the most well-timed thing she has received all month.

I went back to the draft and sat there for a while with the cursor in the subject line field. The subject line is the thesis. I have spent six weeks building the thesis out of what I know and what I have watched fail and what I wrote in the case study folder. All of that is mine. But the thesis is not about what I know. It is about what she is standing in the middle of, maybe, right now, without a name for it yet.


I did not send the email.

I sat there and I did not send it, and I am trying to be honest about what that was. Not avoidance, exactly. Not fear, exactly, though I am not going to claim fear had nothing to do with it. Something more like: I was not sure, by the end of Saturday morning, that the version I had written was the version I meant. I have been wrong enough times about the difference between ready and done that I’m trying to take that seriously.

The cursor sat there for a while. I finally closed the window without saving the draft.

What I know now that I did not know on Friday: the subject line is not about me. It is the name of a problem she might be living in and hasn’t solved yet. I have known the answer to that problem for two decades. I just kept writing around it.

I’ll write the email again Monday morning. I’ll probably send it this time.

I’m aware I may have said that to myself Saturday too.