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Description
You may be responsible for AI in your organization without having had much time to study the technology, use it deeply, or see how other organizations are approaching it. You still have to make decisions about tools, investments, pilots, skills, roles, and what to tell your team. This gives you a private place to work through those decisions with someone who understands both the technology and the people side of transformation. We use the questions already on your desk. We may also build something small for you, because hands-on experience gives you a much better sense of what AI can realistically do. You can schedule the five hours as 60- or 90-minute sessions when you need them during the eight-week period. - An initial session to understand your role, organization, current AI work, and the decisions you are carrying - Five hours of private coaching scheduled around the questions and decisions that come up - One hands-on AI experiment tied to your own work or life - Help thinking through questions such as where to begin, what to buy or build, what a pilot should teach you, and how to prepare people for changes in work - Short written notes after each session that capture decisions, open questions, and what you agreed to do next
What you'll get from this package
One working AI experiment built around a useful task in your work or life
AI leadership decision brief documenting your choices, tradeoffs, open questions, and next steps
90-day AI leadership plan covering the skills, decisions, conversations, and experiments ahead
Additional details
Coaching delivered via live sessions.
I am direct, curious, and comfortable sitting with questions that do not have an obvious answer yet. I am outside your organization, so you do not have to manage my reaction or worry about how the conversation affects your reporting structure. I will help you think, ask questions, and point out what you may be missing. I will also ask you to use the technology because you cannot build good judgment about AI entirely through summaries and presentations. One session may be a conversation about organizational politics; in another, we may open the laptop and build the thing.
- This package is for one leader, not a leadership team. - It does not include a company-wide AI strategy, stakeholder interviews, workshops, or implementation work. - The five live hours must be used within eight weeks. - Additional coaching can be purchased after the package ends.
Services included:
Decision Making
Communication Skills
Strategic Planning
Leadership Development
AI Fundamentals
AI Strategy
Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
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Nelson also coaches for Build with AI and AI Services. View all.

Offered by Nelson S.
Joined July 2026
5.0
AI Transformation Executive Coach
Many leaders are being asked to lead AI transformation before they have had time to study the technology, use it deeply, or see how other organizations are approaching it. I give them a private place to work through the decisions they cannot easily test with their team, peers, or board. My coaching draws on years leading people analytics and technology work inside Wayfair, Sonos, and Figma, my current work advising and building with AI, and my MBA studies at Columbia Business School. I understand the people and organizational consequences of these decisions, and I use the technology enough to examine what is feasible. I work best with direct communicators. We bring the real decision into the room, test the assumptions behind it, and choose a practical next step. Coaching can move between strategic questions and hands-on practice because leaders need both judgment and firsthand experience.