The $285 Billion Leadership Question: Why Your Executive Team Isn't Ready for What Just Happened

“How much per session?”

I hear this at least three times a week from senior leaders comparing executive coaches. It’s the wrong question, but I understand why they ask it.

When you’re evaluating five proposals that all promise “transformational leadership development,” price becomes the only concrete metric. Everything else dissolves into corporate speak about “enhanced presence” and “strategic mindset shifts.”

Here’s what that question reveals: you’re treating leadership development like buying printer paper. And if that’s your approach, you’ve already lost most of the value.

Last week, Anthropic released an AI tool that erased $285 billion in enterprise software market value. RELX dropped 14%, Wolters Kluwer fell 13%. The panic stemmed from a sudden realisation: most CEOs can’t articulate how their companies will survive when AI agents replace the per-seat licensing model that has powered their businesses for decades.

According to BCG’s annual AI Radar survey, half of CEOs believe their job stability depends on getting AI right in 2026.

The problem is clarity. The same gap that prevents leaders from articulating precise AI requirements also kills team inspiration, succession planning, and strategic execution.

The Price-Per-Session Trap

When KPMG negotiated a 14% discount on their 2025 audit fees, they didn’t just save $59,000. They demonstrated what separates leaders who shape markets from those who react to them.

KPMG International told Grant Thornton UK: pass on your AI cost savings, or we’ll find another auditor. Grant Thornton folded. The fee dropped from $416,000 to $357,000.

This is an operating event with real commercial impact. Leaders who can clearly articulate a strategy create negotiating power. Most can’t.

The Conference Board reports that C-suite teams show significant divergence on AI priorities. Tech leaders identify different human capital priorities than CHROs. CMOs disagree with tech leaders on where AI matters most. Despite years of investment, the vast majority of enterprise leaders acknowledge that they are nowhere near full AI integration across core business processes.

Senior leaders know AI matters. They’ve attended the conferences, read the articles, and sat through the briefings. But when asked to explain precisely how AI changes workflow, resource allocation, or talent strategy, most default to vague abstractions about “digital transformation.”

This articulation gap is the same one preventing inspiring leadership. You can’t inspire people towards a future you can’t clearly describe. And you can’t rework business models around AI if you can’t specify what you actually need.

Why Most Leadership Development Disappoints

I’ve reviewed dozens of coaching proposals. Most follow the same pattern: 12 sessions spread across six months, a generic competency framework, promises about “enhanced executive presence,” and zero accountability for business outcomes.

The proposals look similar because most coaches sell the same thing: time. An hour here, an hour there, conversations that feel productive but don’t connect to what’s actually broken in your organisation.

Three reasons these investments fail.

No baseline measurement. Most coaching starts without an objective assessment of current capability. No 360-degree feedback gathering stakeholder perceptions. No interviews revealing what people won’t say in surveys. You can’t improve what you don’t measure. Yet coaches routinely skip this because it’s uncomfortable and time-consuming.

No connection to business reality. Generic frameworks treat all leaders identically. But the capabilities needed to lead a fintech through Series B are completely different from what’s required to integrate two manufacturing businesses post-merger. If coaching doesn’t start with your situation, it won’t solve your problems.

No sustained practice. Knowing what to do and being able to do it under pressure are different skills. You don’t become an inspiring leader by understanding theory. You become one by practising new behaviours in safe environments, receiving feedback, adjusting, and repeating until they become automatic.

This is why asking about session pricing misses the point. You’re not buying hours. You’re buying a development and performance methodology that changes how leaders show up when it matters.

What Actually Drives Performance

When employee engagement dropped to a 10-year low in 2024, most organisations responded with surface fixes. Engagement surveys. Culture consultants. Workshops on psychological safety that changed nothing about how people actually worked.

The fundamental issue persists: leaders don’t know how to create environments where people do their best work.

Research on engaging leadership shows that when leaders inspire followers with a clear, compelling vision, they build self-efficacy, optimism, resilience, and goal achievement.

You already know this. What you might not know is why your previous attempts failed.

The same pattern appears in AI adoption. BCG’s “The Widening AI Gap” report found that C-level executives deeply engaged with AI are 12 times more likely to be among the top 5% of companies succeeding with AI innovation.

What separates the winners from the rest? Clarity. The ability to articulate requirements, align stakeholders, and communicate strategy under uncertainty.

How We Work

At The Clarity Practice, we combine ICF-aligned executive coaching with our Three Pillar Clarity Method: mindfulness-based self-awareness, strategic thinking frameworks, and visual communication methodology.

Over 70% of individuals who receive coaching benefit from improved work performance, relationships, and communication skills, according to the International Coach Federation's Global Coaching Client Study.

Beyond Individual Coaching

Here’s what most leadership development misses: changing one executive’s behaviour doesn’t transform organisational performance. You also need team capability and execution discipline.

We work across three levels:

• Individual executive coaching for C-suite leaders navigating high-stakes transitions: post-merger integration, regional expansion, succession planning, and board pressure to demonstrate AI readiness.
• Team training that builds a coaching mindset across your leadership group. When your entire senior team learns to ask better questions, listen more effectively, and create psychological safety, you change how decisions get made and how quickly you execute.
• Facilitation that directly impacts project success. Strategic off-sites that produce actual decisions, not just discussion. Workshops that align cross-functional teams on execution. Sessions that turn vague strategic intent into clear action plans with accountability.

Most organisations invest in one without the others. You need all three working together. The CEO’s coaching surfaces what needs to change. Team training builds the capability to execute it. Facilitation creates the forums where strategy becomes action.

What to Evaluate Instead of Price

When you compare coaching options, here’s what actually matters:

• What will measurably change? Look for coaches who commit to specific outcomes. We use 360-degree feedback at the start and track improvement against defined behavioural metrics. If a coach isn’t proposing rigorous assessment, they’re not serious about outcomes.
• How does this connect to my business challenges? Generic frameworks don’t solve specific problems. The engagement should start with your actual situation. If the proposal doesn’t reference your business context in detail, it won’t deliver business results.
• What credentials demonstrate proven methodology? ICF certification and Leadership Circle training signal rigorous methods, ethical standards, and ongoing professional development.
• What happens after sessions end? Real behaviour change requires ongoing practice. Ask what sustainable mechanisms are built into the programme. Peer learning structures? Check-in protocols? Ongoing measurement?

The AI Leadership Gap Nobody’s Addressing

Here’s what the $285 billion market crash revealed: it's a leadership crisis.

Gartner predicts that by 2030, at least 40% of enterprise SaaS spend will shift to usage-based, agent-based, or outcome-based pricing. The per-seat licensing model that’s powered software businesses for decades is breaking down.

If AI agents can execute sales workflows without humans logging into Salesforce, the economic foundation shifts. If one person supported by AI can do the work of five, your SaaS vendor’s growth curve flattens.

Leaders who can’t articulate how this affects their business model, talent strategy, and competitive positioning will fail. Not eventually. Soon.

The articulation problem that limits AI adoption mirrors what’s happening in leadership effectiveness. Research shows that the major bottleneck in AI is translating vague human needs into precise software requirements.

Ambiguity in specifications becomes noise in execution. Vague objectives produce inconsistent results. This is true whether you’re deploying AI agents or trying to inspire your team.

The same clarity tools that help leaders articulate vision help them specify AI requirements. The same frameworks that build alignment across C-suite priorities work for defining AI strategy. The same communication methods that inspire teamwork are used for explaining the transformation to stakeholders.

As an executive coach, Leadership Circle practitioner, fractional CMO, and AI ethics professional, I work at the intersection most leadership development ignores: helping Singapore C-suite leaders close the gap between understanding AI matters and knowing how to transform their organisations around it.

What Leadership Actually Looks Like Now

Stop thinking about leadership development as training. Start thinking about it as business infrastructure.

Leaders who create cultures where people do their best work share three characteristics:

Clarity of purpose. They make work meaningful by showing how individual contributions connect to larger outcomes. Not mission statements. Consistent communication about why decisions matter and how work creates value.

Trust through delegation. They create space for people to decide without seeking permission for everything. Research shows that empowering leadership and fostering bottom-up decision-making directly enhances employee involvement and performance.

Visible commitment. They demonstrate priorities through consistent actions, not words, at town halls. The fastest way to destroy inspiration is to say one thing and do another.

These are skills that require deliberate practice in safe environments before you deploy them under pressure.

This is where facilitated workshops deliver what lectures can’t. Well-designed workshops create space for leaders to surface real obstacles (usually their own fear of losing control), practise new behaviours, receive immediate feedback, and build peer accountability that lasts beyond the session.

Combine that with ongoing coaching that holds you accountable when you’re back in operational chaos, and you’ve got a system for sustainable change.

Five Questions for Choosing a Coach

What’s your assessment methodology?
Red flag: “We’ll have a conversation about your goals.”
Green flag: “We start with 360-degree feedback and stakeholder interviews to establish baseline capability.”

How do you measure ROI?
Red flag: “Leadership is hard to quantify.”
Green flag: “We track specific behavioural changes and business outcomes defined at programme start. Here are our client results.”

What are your credentials?
Red flag: “I’ve been coaching for 15 years.”
Green flag: “I’ve led global teams and transformation projects.”

What happens after the engagement ends?
Red flag: “You can always book more sessions.”
Green flag: “We build sustainable accountability structures so change outlasts our formal engagement.”

These questions separate serious, outcomes-focused coaches from people selling motivational conversations.

Start With the Right Question

If you’re a C-suite leader facing engagement challenges, retention problems, or leadership bench gaps while navigating AI disruption, you need more than generic development programmes.

You need a methodology that connects to actual business challenges, delivers trackable outcomes, and builds sustainable capability.

That’s what we do. We work with senior leaders across Singapore and Asia, navigating high-stakes transitions: post-merger integration, regional scaling, succession planning, culture transformation, and AI readiness.

We combine the Three Pillar Clarity Method with ICF-standard coaching, Leadership Circle frameworks, rigorous measurement, and practical support accessing Singapore government funding.

But we’re not right for everyone. If you want the cheapest per-session rate or prefer feel-good conversations without accountability, we’ll disappoint you.

If you’re serious about building leadership cultures that drive business performance while your industry faces existential disruption, let’s discuss what real change looks like in your organisation.

Stop asking “how much per session.”

Start asking, “What will this change about how we perform?”

Ready to move beyond generic leadership training? Contact The Clarity Practice to discuss how executive coaching built for Singapore leaders delivers measurable performance improvements. 

Common Questions About Executive Coaching

How long does executive coaching take to show results?

Most clients see behavioural shifts within 8-12 weeks when working with a structured methodology that includes 360-degree feedback and regular accountability checkpoints. Full leadership transformation, where new behaviours hold under pressure, typically requires six months of sustained practice.

What’s the difference between executive coaching and leadership training?

Training transfers knowledge. Coaching builds capability through practice, feedback, and accountability. Most leaders have attended enough workshops to know what good leadership looks like. The gap is between knowing and doing. Coaching closes that gap by working on real situations in real time and holding you accountable for applying what you learn.

Can you actually measure executive coaching ROI?

Yes, and you should demand it. Start with a baseline using 360-degree feedback, define specific behavioural outcomes tied to business metrics, then track progress. Useful indicators include retention rates, team performance scores, engagement data, and speed of strategic execution.

What credentials should I look for in an executive coach?

Most coaches in Singapore sell 'conversations.' We sell measurable shifts in leadership performance. We use ICF standards as our ethical anchor, but our sessions are driven by real-world experience navigating M&As, culture shifts, and AI disruption. This isn't just a formality; it’s the difference between a nice chat and a rigorous developmental process that respects the complexity of your actual job.

How is The Clarity Practice different from other executive coaches in Singapore?

Three things set us apart. First, we combine ICF-certified coaching with a proprietary methodology (the Three Pillar Clarity Method) that integrates mindfulness, strategic frameworks, and visual communication into a single system. Second, we tie every engagement to business outcomes you can track, not vague promises about “growth.” Third, we operate at the intersection of leadership development and AI transformation, helping C-suite leaders who need clarity on both fronts simultaneously.

What’s the connection between AI transformation and leadership coaching?

The clarity gap that stalls AI adoption is the same gap that undermines leadership effectiveness. Leaders who struggle to articulate precise requirements for AI implementation also struggle to inspire teams, align stakeholders, and drive execution. Coaching that sharpens strategic clarity and communication capability addresses both problems at once, which is why we see it as a single challenge rather than two separate ones.