Why I Picked Her First

The rule revision still held this morning. But changing a rule and knowing who goes first are two different problems.

Leigh Sutton
Leigh Sutton Corporate lifer. Aspiring free agent. 4 min read
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I opened the reminders note before I opened the inbox this morning. That is not usually how the mornings go.

The note has six names. Two are marked. I reached out in early June, sent follow-ups, and those are past their windows now. The other four are sitting there exactly as I wrote them in May.

Yesterday I decided to revise the rule that was holding them. I wrote about it here, and I slept, and I woke up and it still seemed right. That is actually the test I use. The decision passed. Which meant I was no longer asking whether to change the rule. I was asking which name goes first.

I did not expect that to be the harder question. I had been treating the rule as the obstacle, the thing between me and the list. And it was, partly. But what was also between me and the list was the fact that picking who goes first is its own decision, and I had been deferring it inside the larger deferral. So removing the rule did not automatically produce an answer. It just handed me the next problem.


There are four names, and they are not equivalent. I know all of them, some of them well, but knowing someone is not the same as knowing whether your specific thing solves their specific problem.

The 60-Day Save, which is what I have been calling the consulting idea since it was a bullet point in May and what I can now describe in one sentence, is built around a specific problem: enterprise accounts lost not to competition but to neglect, in the sixty days before contract expiration when everyone assumes someone else is managing the relationship. That problem exists in many places. It is more visible in some than others. So the question was not who I knew best. The question was who already knew this problem.

I went through the four names. Not with a grid. More the way you look for something you left in a room, going around it slowly until something catches.

One of the four worked in enterprise renewals for about two years, eight years ago or so. We did not work directly together on renewals. But I was at a dinner, I want to say 2018, where she described losing an account in exactly the pattern I have spent four months calling “the pattern.” She was frustrated and precise. She knew what should have happened, she named the specific moment the relationship stopped being managed, and she was still annoyed about it years later. I remember sitting across the table and thinking: that is the thing. That is the exact thing.

That is the name.

I want to be careful here. I cannot tell you I made this decision scientifically. I made it by sitting with the four names and noticing which one felt most like calling about a thing she already understands versus a thing I would have to convince her to care about. That is not a rigorous methodology. It is also not nothing, after 24 years of reading rooms.


I wrote the email. It took about twenty minutes, which is longer than the second outreach and considerably shorter than the first.

I have not sent it yet.

I am going to send it this afternoon. I want to reread it once at lunch. There is a word in the third sentence I am not sure about, and I do not proofread emails I care about before 8am. That is not avoidance. It is the same habit I applied to the first two emails, and both of those were better for the reread.


What I cannot answer is what happens if this one also goes quiet. I have three more names after her. I have August, which I have now named as the month I reach out to the rest of the list, though I have not made that a calendar entry yet, and August starts in two weeks. I have a consulting pitch I believe in, for a problem I have watched happen across more accounts than I can count, and I cannot control whether the right person is in the room when I say it.

The rule I revised was protecting me against absorbing too many silences at once. That protection is gone now, which I named yesterday and have not stopped knowing since. What I have instead is a cleaner read on which name goes first and why. The logic is sound. The logic being sound has never been the part I was uncertain about.

I’ll send the email after lunch. Ask me in a day or two whether anything happened.