The Journey: #78: CS Is Not Set It and Forget It

Picture the room. I'm sitting in an ELT meeting, and I tell the group I need three days, completely unavailable, and I actually said it just like that, "pretend I'm on PTO," because that was the only way I knew to protect the time from getting eaten by everything else. Some people got it immediately, nodded, moved on, no issue. But a couple of them smirked. Someone made a comment about how nice it must be to disappear for three days, someone else called it overkill, and then the meeting just moved on to the next agenda item, the way passive aggression in an ELT team meeting always does.

This was pre-COVID, so we were still fully in office, which meant the next fight was just getting out of the building. I chose to work from home those three days, and I got pushback on that too, because apparently sitting at my desk with my headphones on while everyone watched me not answer Slack messages was somehow more legitimate than actually removing myself from the noise. Open floor plans are great, until they're not. I needed to be somewhere nobody could tap my shoulder for a "quick question," so I went home, sat at my desk and got to work.

And the work itself wasn't a quick check, it was structured, because "I have a feeling something's off" doesn't hold up in a room full of people who just called you overkill. I built out real criteria across five areas and used them to actually double click into what was true versus what we'd just been assuming. People, are the right folks in the right seats based on what the business needs today, not the org chart from our last reorg.

Process, which of our workflows were running because someone built them once versus because they were still the best way to get the outcome. Tech stack, was every tool we were paying for actually doing what we needed it to, or were we guilty of having “shelfware”.

Data, did I actually trust the numbers we were reporting up, or were we measuring what was easy instead of what was predictive. And customers, had our segmentation kept pace with who our customer base had actually become, or was it still built for who they used to be.

That last bucket is where I found the thing that stuck with me most. We had an entire segment of customers we were talking at instead of with, because at the time, that felt like the only way to scale. We didn't have the resources to do it any other way, so we'd built automation rules and triggers with zero logic behind them, just pushing content out to customers on a timeline that made total sense on our internal calendar and absolutely no sense on theirs. It looked efficient on a dashboard, but if you were the customer you probably felt like you were being spammed.

Peeling that back was uncomfortable, because it meant admitting we'd optimized for our own convenience and called it a strategy. But once we saw it clearly, we rebuilt the program around strategic moments of actual human intervention. We found specific points where a real person showing up added real value and made the customer feel like a partner instead of a lead in someone's marketing sequence.

If I hadn't blocked that time and gone looking, we might have kept running that program exactly as it was, patting ourselves on the back for the automation while quietly eroding trust with everyone.

A few weeks later I came back to that same ELT room with my findings and my recommendations. The people who'd smirked and made comments didn't have much to say this time. Funny how that works.

The Takeaway: Nothing in customer success is set it and forget it. Not your process, not your tech stack, not your org structure, not your comp plans, not your data. If you built it more than two quarters ago and haven't stress tested it since, you don't actually know if it still works, you just know it hasn't broken yet.

FROM MY WORLD

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Customer Success. Revenue Follows.