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Her CEO said “when this fails, let’s talk.” Here’s what changed his mind about AI coaching

Picture of Kirsten Moorefield

Kirsten Moorefield

Co-Founder & CSO of Cloverleaf.me

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Reading Time: 6 minutes

Kathy Quarles, Head of People at 80 Acres Farms, knew what she was walking into. When she brought the idea of AI coaching to her CEO, the response wasn’t enthusiastic. It wasn’t even neutral.

“The comment was, ‘You go ahead and try this. When it fails, let’s talk,'” Kathy recalls. “There was for sure an expectation that this wouldn’t be something that would latch on as a meaningful tool.”

If you lead a people function, you’ve heard some version of this. Maybe not that direct — but the skepticism is familiar. Development tools get filed under “fluffy HR programs” that won’t survive contact with the daily rhythm of business. And the skeptics have a point: most of those investments haven’t produced visible results. Not because the content was wrong, but because the evidence of impact never showed up in a way the business could see.

What changed this CEO’s mind wasn’t a dashboard or a participation report. It was that people started behaving differently — and the shift was visible enough that the business noticed without being told to look.

Get the 2026 AI coaching playbook to see how organizations are implementing AI coaching at scale.

87% of employees believe algorithms give fairer feedback than their managers, and the behavioral research explains why

Before the 80 Acres story makes sense, it helps to understand the mechanism behind it. A 2024 Gartner survey of 3,500 employees found that 87% believe algorithms could give fairer feedback than their managers. A separate 2025 study published in Behavioral Sciences went further: when negative feedback came from AI rather than a leader, employees experienced less shame and fewer withdrawal behaviors. The feedback wasn’t softer. The content was the same. But removing the interpersonal weight changed how people received it.

This matters because defensiveness is the thing that kills most feedback. A manager delivers a coaching insight. The employee’s first instinct isn’t to absorb it — it’s to evaluate the messenger. Do they have an agenda? Is this fair? Is this personal? When coaching comes from data instead of a person, that entire layer of self-protection drops. What’s left is the actual content of the feedback — and space to decide what to do with it.

Kathy saw exactly this. “People became less defensive about the feedback,” she says. “It allowed this sort of free space of non-judgment coaching which was really unique.” Employees described getting a coaching tip in the morning, sitting with it, deciding how to incorporate it into their day — and doing it without someone looking over their shoulder to see if they followed through. That’s not engagement. That’s behavior change.

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The behavioral shift that convinced a skeptical CEO happened in Slack threads and hallway conversations, not in a quarterly report

80 Acres Farms is a vertical farming company that had done four acquisitions in 18 months when Kathy introduced AI coaching. New teams, new personalities, new ways of working — and the pressure to integrate fast. The company had used assessments and behavioral workshops before. “Everyone was really excited about it at the time we were doing it,” Kathy says. “And then we all have to go back to our day jobs and we’re super busy. To take the time to think about how those learnings apply in the daily rhythm of things — no one has time for that.”

What she observed after introducing coaching that showed up daily — in morning emails, before meetings, in Slack — wasn’t a spike in engagement metrics. It was something harder to manufacture and harder to ignore: people started voluntarily sharing coaching insights with each other.

“We’ll share the daily emails we get and send it to someone and say, ‘Cloverleaf called me out this morning — haha,'” Kathy describes. “And just 30 minutes ago, I had an email shared by two of my team members saying, ‘Oh, this is why we balance each other out so well.’ There was constructive feedback on both ends of how people like to do their work.”

Think about what this represents. These aren’t people completing a required development activity. They’re voluntarily surfacing their own development areas — and doing it with humor, with openness, without being asked. That’s the kind of behavioral evidence that doesn’t show up in a participation dashboard, but it’s visible to anyone paying attention. Including a skeptical CEO.

A leader shared a coaching tip about a defensive employee and it proved the data right in real time

One of the most concrete moments Kathy described was a leader who received a coaching message about how one of their employees tends to receive feedback — specifically, that the employee often gets defensive. The coaching included guidance on how to approach the conversation differently based on that person’s style.

The leader agreed with the insight and shared it directly with the employee. The employee’s response? Defensiveness — exactly what the data predicted. “What’s funny is that we actually saw the feedback that was shared — we lived it then in that moment,” Kathy says.

But here’s where the story shifts. The leader pulled back, reread the coaching tips on how this specific employee best receives feedback, adapted their approach, and went back. The second conversation was productive. The employee engaged with the constructive feedback.

This is the kind of moment that separates coaching that changes behavior from coaching that generates activity. The leader didn’t just receive an insight — they applied it, watched it fail, recalibrated using assessment-grounded coaching data, and tried again. That loop — insight, application, feedback, adjustment — is behavior change happening in real time. And it didn’t require a workshop, a scheduled session, or a follow-up from HR.

The signs coaching is working look like less defensiveness, voluntary vulnerability, and leaders adapting to each person on their team

Most organizations try to prove coaching’s value with the metrics they already have: participation rates, completion percentages, satisfaction surveys. These numbers feel safe because they’re easy to collect. But they don’t answer the question a skeptical leader is actually asking, which is: is this changing how people work?

The evidence that changed the CEO’s mind at 80 Acres wasn’t a report. It was that he could see it. People talking about their development openly. Leaders adjusting how they give feedback based on who they’re talking to. Team members explaining their working styles to each other using shared language. The real ROI of coaching showed up in behavior before it showed up in any metric.

Kathy describes what this looks like from the inside: “It makes it real. We can continue to build on it — build it into performance conversations, other development and coaching opportunities. As we build careers and have people span into different levels and jobs and functions, we can take our learnings and evolve it even more.”

If you’re trying to earn trust for coaching investments, look for these signals instead of dashboard metrics: Are people less guarded when receiving feedback? Are they sharing development insights with each other without being asked? Are leaders adapting their approach based on who they’re talking to — not defaulting to one style for everyone? Are conversations about growth happening outside of formal reviews? Those are the signs that coaching is actually working. And they’re the evidence that converts skeptics — because they’re visible to the business, not buried in an HR platform.

A pilot generated the behavioral evidence to convert a CEO who expected coaching to fail

Kathy didn’t try to convince her CEO with a pitch deck. She piloted coaching with a couple of small groups first — tested whether people found it accurate, useful, and genuinely reflective of how they work. “We actually piloted it with a couple small groups to start to see if we received good feedback, if people liked it, if they were finding it useful,” she says. “It allowed us to test it, and if it didn’t work, we just wouldn’t move forward.”

This is the approach that works when leadership is skeptical: don’t argue for the investment upfront. Start small enough that the risk is contained. Let the behavioral evidence accumulate. Then let the business see it. The pilot groups at 80 Acres generated the visible shifts — less defensiveness, voluntary sharing, adapted conversations — that made expanding easy to justify. The CEO didn’t need to be convinced by data. He was convinced by watching people change.

“I feel good about it,” Kathy says now, looking back. “Most importantly for me, I want to be able to provide things and support things that have benefit to our employees and our company.” That benefit didn’t show up in a satisfaction score. It showed up in how people started treating each other — and in a CEO who went from expecting failure to seeing coaching as part of how the company operates.

Build the case for AI coaching with the playbook behind these results

The behavioral shifts Kathy describes — less defensiveness, voluntary vulnerability, leaders adapting in real time — don’t happen by accident. They happen when coaching is built into the daily rhythm of work, grounded in assessment data, and delivered without the interpersonal weight that triggers self-protection. The 2026 AI Coaching Playbook for Talent Development lays out how to build this into your organization — from pilot design to stakeholder buy-in to measuring the outcomes that actually matter.

Picture of Kirsten Moorefield

Kirsten Moorefield

Kirsten is the co-founder & COO of Cloverleaf.me -- a B2B SaaS platform that provides Automated Coaching™ to tens of thousands of teams in the biggest brands across the globe – where she oversees all things Product and Brand. She often speaks on the power of diversity of thought and psychologically safe cultures, from her TEDx talk to her podcast “People are Complicated,” her LinkedIn Lives with Talent, Learning and Development Leaders, and her upcoming book “Thrive: A Manifesto for a New Era of Collaboration.” While building Cloverleaf, Kirsten has also been building her young family in Cincinnati, Ohio, where she lives with her husband and two young kids.