"Everyone has a plan until they get punched in the face."
Mike Tyson said it best, didn't he?
I was thinking about this quote while staring at my computer screen, thinking about how our "perfect" customer success plans often fall apart in real time.
You know that feeling?
When you've color-coded your spreadsheets, mapped every stakeholder, planned every milestone... and then Tuesday happens with the fun surprise of leadership changes, integrations breaking, and the new CTOs deciding to "evaluate all vendors" three months before renewal.
We plan like nothing will ever go wrong. We build these beautiful 90-day roadmaps and business reviews like we're conducting an orchestra, not managing human beings with their own chaos, budget cuts, and bad decisions.
But here's the thing - your customers are getting punched, too.
Their champions leave. Their priorities change overnight. Their budgets get slashed. Their integrations break at the worst possible moment. They're not trying to ruin your renewal - they're just trying to survive their own reality.
The punches that hurt
I've been doing this long enough to know there are four types of disasters that kill renewals:
Champion chaos. People leave, get promoted, or just stop caring. New hires want to prove themselves by questioning everything. Your relationship-based success plan just became someone else's audit target.
Product disasters. Bugs that break core workflows. Features that don't work as promised. Integrations that suddenly stop talking to each other. Security incidents that make everyone panic. Your engineering team says "we're working on it" while your customer evaluates alternatives.
Business earthquakes. Budget cuts because the economy got weird. Mergers that change everything. New leadership with completely different priorities. Your perfect renewal timeline just became someone's cost-reduction initiative.
Internal chaos. Your sales team overpromised (shocking). Support response times are terrible. Implementation is taking forever. Everyone's pointing fingers while your customer loses faith in your entire company.
The worst part? These things happen in clusters. Never just one crisis at a time - always three, all at once, all urgent.
What I learned from getting punched repeatedly
After getting my plans destroyed enough times, I finally figured something out. The problem wasn't that I couldn't predict these disasters. The problem was that I was planning like they wouldn't happen.
So I changed how I think about planning entirely.
I plan heavily for four things: The first 90 days (when everything usually breaks), renewal prep (start way earlier than feels necessary), champion changes (they will happen, not if), and major integrations (they will be messy, plan accordingly).
I don't overplan these things anymore: Monthly targets that change every month anyway, specific feature requests that get reprioritized, training schedules more than two months out. Who are we kidding? None of us knows where we'll be in six months.
I always have backup champions now. Always. I don't care how solid that relationship feels or how much your main contact loves you. People leave. They get busy. They stop returning calls or attending syncs. I'm starting to map at least a few people who could advocate for us if our champion disappeared tomorrow.
I know my top three risks at all times. Right now, what are the three things that could kill this renewal? I write them down. Then I write down what I'll do about each one. Not "monitor the situation" - real actions with real timelines.
How to respond when you get hit (because you will)
Here's what I do now when everything explodes:
First: I don't panic. I know, easier said than done. But panicking makes everything worse. I get the actual facts first. What really broke? Who's actually affected? What's the real timeline? I alert my team with information, not anxiety.
Second: Time for the uncomfortable conversation. I call the customer. I reset expectations honestly. Yes, it's awkward. Yes, they might be upset. But pretending everything's fine while scrambling behind the scenes is way worse. I focus on what we can actually deliver and when.
Third: Quick wins to rebuild trust. I fix what can be fixed immediately, even if it's not perfect. I find alternative solutions. I rebuild relationships that got strained. I show progress, not just promises.
The key things I learned? Your customers want to see how you handle problems, not avoid them. They need you to be reliable when things go wrong.
Hit me with that Jazz
I stopped planning like a project manager and started responding like a jazz musician.
Project managers try to control every variable and stick to the plan no matter what. Jazz musicians know the song will change, and they get good at improvising with whatever happens.
The best customer success managers don't avoid problems; they get really good at solving them quickly and transparently.
Your customers will trust you more after you handle a crisis well than if nothing ever goes wrong because they know that when (not if) their world gets chaotic, you'll be the vendor who shows up and figures it out with them.
Plans are great, but responses are everything.
There's much more to say about this. But we'll pause here for now.
Keep being the reliable one, as I know you are.
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