Leading with confidence: How AI coaching tools provide in-the-moment support

Elly is staring at her screen, about to join a 1-on-1 with Leon, a direct report who’s been struggling to complete projects on time. During this call, she needs to give him constructive feedback. Her heart rate rises. She knows what she wants to say, but questions still linger in her mind:

How will he react? Am I approaching this the right way? What if I make things worse?

Meanwhile, Marc is sitting on difficult news he needs to share with his team. He’s already delayed the conversation twice, plagued by similar doubts:

How do I say this? Is now the right time? What if they respond poorly?

If you’re a manager, these scenarios probably sound familiar. The micro-moments when leaders hesitate before delivering constructive feedback, sending a carefully-worded Slack message, or preparing to offer someone a stretch project are where leadership truly happens. Often, it’s not the big decisions and grand pronouncements that matter most, but the everyday how.

The unmet need: Coaching in the micro-moments

Historically, companies have supported their people with static playbooks, systems, and processes, but even a scalable support structure only gets a company so far. In many moments that truly test leadership – the everyday, high-stakes conversations – managers have had to fend for themselves. If a manager wanted personalized support, they typically had to pay for it out of their own pocket. While some were able to go that route, access to such support has remained out of reach for most, as Greta (a coach and psychologist) can attest.

Fortunately, the landscape is shifting, and managers have access to new tools. People are increasingly relying on generative AI, specifically large language models (LLMs), for guidance on everything from their career to personal finance, life organization, and more.

However, this shifting landscape comes with a crucial caveat. While AI is beginning to fill the coaching gap by offering on-demand support, this support too often lacks context about the company, the team, and the individuals involved.

Worse, without careful curation, LLMs are known to fall into the trap of LLM sycophancy – agreeing with users even when they shouldn't, validating doubts or frustrations that are misplaced, counterproductive, or just plain wrong. This tendency for LLMs to over-agree is compounded when they lack the necessary context to challenge or reframe what the individual is saying.

A good human coach wouldn’t agree when they shouldn’t – but your LLM might.

AI tools (and LLMs in particular) are opening doors to a level of coaching support that would’ve seemed impossible just a few years ago. But as we’ll explore next, not all AI coaching is created equal. When it comes to leadership coaching, the quality of support matters just as much as its availability.

The quality imperative: Beyond generic LLMs

As AI coaching solutions become more widespread, a critical distinction emerges: Not all AI coaches offer the same level of support or enable similar (positive) results. Furthermore, using a generic LLM as a coach may fall foul of sounding supportive whilst offering little by way of progress. Picking the wrong AI coach can have negative consequences if it leads managers and employees astray or inappropriately validates misguided beliefs.

To be effective, an AI coach must be:

• Grounded in evidence. Built on a robust foundation of people science and best-practice coaching methods.
• Context-aware. Able to consider your company’s localized strategic landscape, as well as the specific context of the coachee’s situation, including relevant company data.
• Disagreeable when necessary. Willing to call out bad habits or problematic thinking that could lead to damaging interpersonal decisions.

Effective AI coaching tools offer high-quality support to everyone at the company in a way that has not been possible before. It is truly the great democratizer of coaching at work. Suddenly, those who would never have the opportunity to speak with a people scientist or coach have that wisdom available to them in real-time.

In designing our own AI Coach, we anchored it in Culture Amp’s deep people science expertise and evidence base. Our AI coaching system acts like a scaled and confidential thought partner, bringing best-practice guidance to the most critical leadership moments, both big and small.

Why micro-moments of leadership matter more than you may think

Let’s return to Leon, the direct report who is about to receive constructive feedback from his manager, Elly. His experience in that conversation will be shaped not just by what needs discussing, but by the broader context: Elly’s team size, manager capacity, and the relationship they’ve built.

Our 2023 study on the state of the manager revealed a critical insight: As team size grows, the experience of direct reports declines.

This makes intuitive sense, as a manager's time doesn't increase with each additional direct report. Employees on larger teams likely get less time with their manager, and most managers aren’t able to scale their approach to ensure that all of their direct reports get the support they need to thrive.

If the answer isn’t more time (which it just can’t be), what is it?

Imagine if every manager had more capacity to lead, because they had a conversational supporter on the sidelines – a tool available 24/7 to coach, challenge, and elevate them when they need a little extra guidance.

Our recent study on AI in HR provided an uplifting insight. Managers are already seeking out AI for conversational coaching support during these critical micro-moments of leadership. In fact, we found that managers are using AI tools the most across all levels of the organization, and this use is actually boosting their confidence in their ability to lead.

Managers are 10% points above the C-suite when it comes to the confidence they’re gaining by using LLMs. When we looked at what managers are doing with AI tools, we learned that 60% of managers are using them to have tough conversations (5% points higher than other leadership levels).

We suspect that many of those tough conversations are performance-related, like we saw with Leon and Elly – and getting these conversations right can affect how employees perform in the future.

Poor performance doesn’t come out of nowhere.

It’s the manager’s responsibility to spot lagging performance, intervene early, and foster an environment and interpersonal style that supports improvement and growth.

When managers get stretched too thin, they may miss subtle signals, like someone pulling back or shutting down. But when a manager is "on" and present, everyone benefits. Effective AI coaching can help managers do their best work, and great leadership has a ripple effect.

Our research consistently shows that managers have a powerful influence over the employee experience. What managers do and say impacts their employees' performance, behaviors, and habits.

The challenge for managers and leaders alike goes beyond knowing what to say and into knowing how and when to say it. It’s about having effective conversations, consistently, with every person on the team. This builds and strengthens long-term leadership capability and soft skills over time. But leading humans doesn’t scale neatly, especially when managers are under pressure and facing challenges alone.

AI coaching tools benefit managers, blending the tactical and practical

Our AI Coach gives managers something they may rarely get at work – a sense that they have support and guidance, even in their toughest leadership moments – and it does so in a way that is underpinned by the deep Culture Amp evidence base.

How does this help Elly, Leon’s manager, in the moments before she delivers constructive feedback? It enables her to swiftly identify how to have the conversation in a way that protects psychological safety – an important ingredient of building sustainable high performance. She can practice and refine the conversation by role-playing with AI Coach, applying powerful leadership frameworks and coaching techniques backed by people science.

The implications of this type of democratized support go beyond individual effectiveness. When managers have sophisticated support for micro-moments of leadership and decision-making, the cumulative effect on organizational culture can be profound. What this looks like will vary from organization to organization, but it could lead to performance conversations happening sooner and psychological safety improving through thousands of small interactions. Broad access to quality AI coaching support can amplify the human experience and human interactions at work, in new and exciting ways.

The future of leadership development is here

As the market floods with AI solutions, organizations face a critical choice of what AI tools to adopt and how to adopt them - and amongst them are solutions to help people grow, lead, and work together better.

We stand at the threshold of what may become the most significant democratization of leadership development in organizational history. The shift is already underway.

The question is no longer whether AI-enabled coaching will become part of every employee’s toolkit, including those who manage and lead. It’s how thoughtfully such coaching systems will be shaped to provide effective, evidence-based support when it's needed most.

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