How a Fortune 500 Customer Success Leader Used AI to Cut Through Review Season Chaos
“One thing after another.”
That’s how Jenny (name changed for privacy), a Customer Success Manager at a Fortune 500 company, described her week. Escalations piling up, mid-year reviews looming, and the nonstop drumbeat of customer issues left little space to think, let alone lead.
For six weeks, I partnered with Jenny in a 1:1 coaching engagement focused on helping her adopt and apply AI in the moments that mattered most: navigating tense client escalations, balancing leadership of a distributed team across multiple countries, and collaborating cross-functionally to drive client success.
Like many leaders, Jenny faced a familiar tension: the moments designed for reflection—like performance reviews—often collided with the busiest operational demands. Reviews risked becoming a box-checking exercise instead of a real opportunity to recognize, develop, and inspire.
That was the pattern we set out to break together.
When I asked if AI had been a helpful sidekick during the rush of mid-year reviews, Jenny didn’t hesitate: “Yeah, very much so actually. It’s helped a lot.”
She explained how it changed the process of writing her own review:
“Especially when I was doing my individual one. It helps you align to the values, and it actually helps you pinpoint how you’ve contributed. Sometimes it’s hard to find an example, and then suddenly it’s like, oh yeah, now it makes more sense. I get that.”
Instead of struggling to translate her impact into company language, Jenny found clarity. “It was really good,” she said.
Encouraged by that experience, she extended the approach to her team. “I’m gonna use it to do them for my staff as well. It’s been very helpful.”
The results of our coaching partnership were immediate:
Clarity under pressure: Reviews that once felt rushed now carried specific, values-aligned examples.
Time reclaimed: Hours of staring at a blank screen gave way to space for higher-value leadership conversations.
Recognition amplified: Team members received feedback that was sharper, more personal, and directly tied to the company’s vision.
Confidence in escalation leadership: Jenny learned how to lean on AI for quick prep in client crises, allowing her to respond with sharper perspective while keeping her team supported.
Jenny described it simply: “It makes you see where you made a difference.”
Last words
In a season often marked by exhaustion and paperwork, she discovered a shift. AI wasn’t just handling the grind—it was helping her honor the work of her team while keeping pace with the relentless demands of her global role.
The deeper truth is this: leadership isn’t just about doing more with less. It’s about creating space to see and celebrate impact—even when the calendar is full and the issues keep escalating.
And sometimes, that shift begins with the right partnership—plus one unexpected ally.
