AI Coaching for CEOs
You need to understand AI before your company can act on it. This is where you start.
The CEO's AI Dilemma
Your board wants an AI position. Your leadership team wants direction. Vendors are pitching you AI solutions every week. And your peers are talking about AI like they've already figured it out (most haven't).
Meanwhile, you're making decisions that will shape your company's relationship with AI for years — and you're doing it without having personally experienced what these tools can actually do. Not in a demo. Not in a pitch deck. In your actual work.
That's the dilemma: you need to lead on AI, but you haven't had the space to learn it yourself. Not because you lack the ability — because you lack the time, the right format, and someone who'll be honest with you about what matters and what doesn't.
What You Get From a Session
Strategic Clarity
Understand what AI can and can't do for your specific business. Cut through the noise with an honest assessment.
Boardroom Credibility
Speak about AI from personal experience, not talking points. Your board and investors will notice the difference.
Vendor Evaluation Skills
Know the right questions to ask AI vendors. Understand what's real capability versus marketing.
Personal Productivity
See AI applied to your own work — board prep, strategic analysis, communications, research — in real time.
Team Leadership
Guide your team's AI adoption from a position of understanding, not theory.
Decision Confidence
Make AI investment and strategy decisions with firsthand knowledge of the technology's capabilities.
How It Works
Confidential Intake
You complete a detailed intake covering your role, strategic priorities, what your board is asking about AI, and where you're spending time on work that AI might handle better. Everything is confidential.
90-Minute CEO Intensive
The first 30 minutes cover what you need to know about AI as a business leader — not technical details, but the strategic landscape. The remaining 60 minutes are live demonstrations using your actual CEO-level workflows: board prep, strategic analysis, competitive research, communications, and decision support.
Ongoing Support
You leave with a written summary, custom templates, tool recommendations, and two weeks of email support. As you start using AI in your daily work, questions come up — you'll have someone to ask.
The Honest Truth About AI for CEOs
AI is genuinely transformative for certain workflows. It can dramatically accelerate research, analysis, writing, and decision preparation. A CEO who understands how to use AI tools effectively has a real advantage — in personal productivity and in strategic decision-making.
But AI isn't magic. It won't replace your judgment, your relationships, or your strategic instincts. And most of the AI pitches you're hearing from vendors are overselling what the technology can reliably do today.
What a coaching session gives you is the ability to tell the difference. After 90 minutes, you'll know what AI does well, where it falls short, and exactly how it applies to your specific situation. That clarity is worth more than any vendor demo.
Your Coach
Sacha Windisch — 20+ years in technology transformation across global financial institutions, startups, and enterprises. MIT AI Product Design graduate. Based in Montreal, working with executives across North America and globally. No vendor affiliations, no platform to sell — just honest guidance based on what actually works.
Frequently Asked Questions
Is this confidential?
Completely. Everything discussed in the session stays between us. Many CEOs appreciate having a private space to ask questions they wouldn't raise in front of their team or board.
Will this help me evaluate AI vendors?
Yes. After the session, you'll understand what questions to ask vendors, what capabilities are real versus marketing, and how to assess whether an AI investment makes sense for your business.
How much time do I need to commit?
The session itself is 90 minutes. Before that, you'll spend about 15 minutes on an intake form. After the session, you'll have templates and tools you can start using immediately — no multi-week homework.
I'm not technical at all. Is that a problem?
Not at all. The session is designed for business leaders, not engineers. Everything is explained in practical terms. No jargon, no code, no technical prerequisites.
What if I've already tried ChatGPT and wasn't impressed?
That's actually very common. Most executives who try AI tools on their own get underwhelming results because they're using generic approaches. The session shows you how to use AI in ways that are specific to your actual work — the results are dramatically different.
Book Your CEO AI Intensive
90 focused minutes. Personalized to your business. Completely confidential. No vendor pitches.
Book Your Session