The Renewal Call I Kept Not Making

There's a bill I know is going to be higher than I expect. I could check it any day this week. I check it the day it's due, every time.

I do the same thing with renewals I'm nervous about, and I've done it enough times now to know it's a pattern, not a one-off. The account goes quiet. Calls get shorter. Someone new starts showing up in meetings and nobody explains why. I notice all of it, and I tell myself it's probably nothing, and I do not pick up the phone.

Then the renewal is six weeks out and I'm trying to get an executive on a call I should have made in month two.

The part I don't love: I trust people by default. Not a policy I reasoned my way to, just where I start. So when something feels off with a customer, my instinct is to explain it away instead of treating it as data. That's convenient, because acting on it means having a conversation I don't want to have. It's inconvenient later, because by the time I finally have it, I've usually lost the room I would have had if I'd called sooner.

I ran an incubator for four years and then did economic development for a state, so I watched this play out across businesses that had nothing else in common. The warning signs always showed up early and got acted on late. Years after I'd already been living this badly, I read Andy Grove's line about bad news traveling slowly through an organization, and it landed immediately, because I'd been running my own private version of it. Bad news doesn't get hidden from me by other people nearly as often as I sit on it myself before I even bring it to the team.

What I still haven't solved is telling the difference, early, between an account that's quiet because they're busy and one that's quiet because they're gone. I get it wrong in both directions. I've made the call too soon and annoyed someone who was fine. I've made it too late and lost someone who would have stayed if I'd just asked.

If you run renewals or manage accounts — how do you tell the difference before it's obvious?