What Sixty Days Actually Means

I named my entire consulting concept after a sixty-day window. Today is Day 60. I've been turning that over since morning coffee.

Leigh Sutton
Leigh Sutton Corporate lifer. Aspiring free agent. 4 min read
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The phone note entry I’ve been most certain about is item nine: renewals consulting: the 60-day save. The others have question marks, false starts, one I crossed out the next morning. Item nine is just a statement. Confident even in note form.

The premise is specific enough to say in a sentence: enterprise accounts aren’t lost to the competition, they’re lost to neglect in the final sixty days before a contract expires. I watched this happen for years before I named it. The account goes quiet. The relationship manager assumes quiet means satisfied. Nobody asks the questions that feel too direct to ask. The renewal window opens and the client has already decided somewhere they didn’t tell you about. You’re fighting to hold something that should never have reached this point.

I’ve built three case studies around this. I have a pitch for it that comes out clearly now. I know exactly what it looks like when a company is sixty days out and nobody is watching.

Today is Day 60.

I noticed it while making coffee this morning and I’ve been turning it over since.


The follow-up to the second contact went out yesterday. The first contact’s follow-up has been out since June 15. Neither has turned into a scheduled call yet. I know that’s not an unusual pace. What I’ve been asking myself today is: in the renewal situations I’ve handled, was the waiting the hard part?

It wasn’t. The hard part was the period before the follow-up. The sixty days when you had to be actively in the room, asking the things that felt too direct, surfacing concerns before they settled into decisions. By the time the follow-up email went out, the real work had either happened or it hadn’t. The follow-up was confirmation. Not strategy.

I’m not sure what to do with that observation. But it won’t leave me alone.


Here is what I know about sixty-day windows, applied as honestly as I can to where I’m standing.

The first thing: the accounts that went badly didn’t fail because of price or features. They failed because the relationship manager started assuming. We’ve had this account for six years. They know us. We’re fine. The assumption was the problem. The moment you stop asking questions because you think you already know the answers, that’s when the window starts closing.

I’ve been asking questions. The blog is sixty days of questions. I think I’ve been paying attention. I want to be careful about that sentence, though. Watching an inbox first thing in the morning is not the same as asking the uncomfortable question. Checking the analytics is not the same as being in the room. Whether I’ve been paying attention or just watching, I’m not as sure as I was when I started that paragraph.

The second thing: the most useful thing I ever did in a renewal situation was ask one question the client didn’t expect. Not strategic. Not clever. True. Is there anything you haven’t told me yet? You’d be surprised how many times something came out that changed what happened next.

I don’t know what my own unanswered question is right now. That’s the thing that’s been bothering me more than the waiting.


When I wrote the 60-day save in my phone note I was thinking about other people’s problems. A VP of Sales who doesn’t know her account is about to walk. A renewal manager who gets credit for the auto-renews and then spends a quarter explaining the churns. People who need someone in the room who is paying actual attention.

I was not thinking of myself as the account that needed watching.

I’m sixty days in. Two conversations pending, neither scheduled. Three pages in a document I haven’t named. A follow-up sent yesterday morning. An outreach inbox I check before I check the one that pays me.

The accounts I lost were the ones where I stopped wondering.

I don’t think I’ve stopped. I’m not entirely sure that’s the same thing as doing this right.