Feature Story
Before AI was the answer to everything, the mandate was to automate. And this was something I bought into completely.
I was deep in it to the extent I could be with the tech stack I had. I was making notes of what triggers I could use, the sequences to build, and finding every possible place I could remove manual effort from my teams workflow. This felt smart at the time and I felt like a progressive leader.
I was being efficient and building for scale which was what every CEO and board wanted.
But I learned the hard way that not everything should be automated. It’s like the saying, just because you can, doesn’t mean you should.
That realization started with my post-renewal email.
On paper, this totally made sense. The trigger was the closed won opportunity, the timing was immediately, I crafted a message that was generally applicable and professional so from an operations standpoint I was checking all the boxes.
What I was missing though, was everything else.
Treating the renewal like a transaction was wrong. This was a milestone and I was missing the big opportunity to strengthen the partnership, mitigate risk and to drive strategy.
Buy automating this email, my team missed the ability to have the right discussion with our customers and to answer basic questions like:
Why did you renew?
What do we need to accomplish over this next term in order for you to renew again?
What are your current priorities and how do we fit in?
How will you continue to measure our success?
Most important of all … We lost the ability to say thank you. Not in an automated way, but in a way that says, thank you for choosing us. Thank you for trusting us. In a real and human way that people can feel.
I read this recently, but did you know that people say Thank You more to Claude and ChatGPT then they do to other people. Let that sink in.
We’re expressing gratitude to technology, more than we are to each other. And now we are focused on automating those moments away.
Scary.
Automation is a tool, but it shouldn’t be your default. Some moments in the customer journey carry emotional weight that no trigger sequence can replicate. The post-renewal email is one example.
Let’s stop giving away moments that matter.
The AI conversation in CS right now is almost entirely focused on what we can hand off. We’re hearing things like summaries, QBR prep, health scoring, renewal risk flags, and onboarding tasks all being outsourced. And yes, in your business, these things might make sense to offload.
But maybe we’re overcorrecting.
We’re all so focused on capacity and coverage that we’re automating the moments that actually build trust and relationships. Then we stand back and wonder why customers feel like their being managed and treating us like vendors and not like partners.
Here is how I’d flip this to avoid making big mistakes.
Instead of asking “what can we automate?” start asking, “what shouldn’t we automate?”
For me this might look like this:
Success Plans and Value Validation
AI can help structure it but it should replace the conversation where you and your customer have a discussion and align on what success means. You risk losing the opportunity to build a relationship and look for context that might otherwise be missing.
Emotionally Loaded Moments
Escalations, gratitude, or realignment - these are important opportunities to lean in and seek to understand. Conducting discovery when something has changed in their business requires you to be present and engaged.Context and timing matter here.
Commercial and Revenue Conversations
Expansion discovery, renewal discussion and pricing conversations can be prepped with AI but we should not try to delegate to it.The moment your customer feels like their renewal is a workflow is when you are seen as a tool not a partner.
The goal isn’t to automate less, but it should be to automate with intention. You need to think about what should be human first and then build AI and automation around everything else.
But like I always say … It depends.
If your business calls for all automation and AI, go all in, but I still believe there is a place where humans add value that these tools and systems can’t.
THE RESOURCE
The “Human First” Audit
Before your next AI strategy session with your Ops Team, run everything through this filter:
Does this moment carry emotional eight for the customer?
Would the customer notice or care if this came from a person vs. a system?
Does this interaction create information, insight, or trust that we’d lose if we automated it?
If the answer is YES to any of those questions, DO NOT AUTOMATE. No exceptions.
Use this as a team exercise. Pull up your customer journey map, walk through every touchpoint and ask these 3 questions. You’ve now built your “Do Not Automate” list before you build anything else.
I’m sure you’ll be surprised what stays and what goes.
FROM MY WORLD
Quick updates … Events, podcasts, awards, news, etc.
EPS #7: It’s not them. It’s You. Why Execs Aren’t Showing Up and What to Do.
How to rearchitect your business review process to host conversations your customers find valuable.
The Spy Turned CCO at People.ai featuring Natalie Wolf
Listen to Natalie’s path to the C-suite and her advice on ownership, courage, and owning your own playbook.
CCO SUMMIT SILICON VALLEY
Chief Customer Officer Summit Silicon Valley: April 15th
Join me and tons of leading CCOs and those shaping the future of customer-centric strategy for a day of unrivaled networking, learning, and discussion.
ATLCS SUMMIT
I’m the Keynote Speaker at the ATLCS Summit: April 23rd
Summit is the premier gathering for CS thought-leadership in the Southeast. An interactive, one-day event built for customer practitioners and leaders.
NEW CUSTOMER SUCCESS COURSE
The CS Architect Workshop is closing in 3 weeks and we only have a few spots left.
If you're building a CS program for the first time or finally ready to stop patching the one you have, this is for you.
Over 10 weeks, in a small cohort setting, we build together. Not theory. Not slides you'll never open again. Actual frameworks, real feedback, and a program you walk away with.
Here's what we cover:
How to create customer segments that actually matter (not just sorted by ARR)
How to design an intentional, outside-in customer journey instead of one built around your internal convenience
How to define what a healthy customer looks like in YOUR business, not someone else's benchmark
And so much more
You'll leave with a playbook, a clearer strategy, and the confidence to lead it.
10 weeks. Small cohort. I teach and build alongside you.
Investment: $4,000
We close in 3 weeks and seats are almost gone. If you've been waiting for the right time, this is it.
👉 Grab your spot here
POLL
What's one moment in your customer journey that you would never hand over to automation, no matter how much time it would save?
Hit reply and tell me.
I'm building something with these answers.
A FINAL NOTE
CLOSING WITH KRISTI
We're not going backward on AI. That's not the point.
The point is that efficiency without intention isn't strategy. And when we automate the moments that matter most, we don't just save time, we actually trade something we can't get back.
So build your automation roadmap, yes, absolutely, but start with the list of your non-negotiables.
The customers who stay aren't staying because your sequences are clean. They're staying because someone made them feel like it was worth it.
Make sure that someone is still a human.
See you next week,
Customer Success. Revenue Follows.