Executive AI Coaching

Private, founder-led coaching for leaders navigating AI in complex, high-responsibility environments.

The Focus of Executive AI Coaching

Executive AI coaching exists because leaders are increasingly expected to make decisions about AI before their organisations are ready to fully support them.

Executive AI coaching is centred on artificial intelligence in a business context.

Sessions focus on helping leaders think clearly about how AI affects their role, decisions, responsibilities and everyday work. This may involve sense-checking AI-related discussions already happening in the organisation, forming a grounded point of view on where AI should and should not be applied or navigating expectations being placed on teams and leaders.

Some executives arrive with a defined AI challenge. Others are asked to investigate, explore or respond to AI without clear direction. In some cases, leaders want private, focused coaching to work effectively with AI without joining a group or course.

The format adapts to the situation. Every session is anchored in using AI with judgement, relevance and confidence in real business contexts.

How We Work Together

Starting with context and intent.

Before a session takes place, we start with a conversation.

The purpose of this first discussion is to understand your context, the responsibilities you carry and the areas where you want clarity or support. Some executives arrive with a clearly defined challenge. Others are navigating broader questions around direction, risk, capability or confidence. Both are valid starting points.

This conversation allows us to establish whether Executive AI Coaching is the right fit and ensures that, if we proceed our sessions begin at the right level from the outset.

A focused first conversation

The first session is used to align on context, pressures and priorities.

We explore what is happening in your work today, what decisions are in front of you and what outcomes matter most. Together, we define the focus for the next phase of coaching and agree what progress should look like.

Nothing is left vague. Direction is established early.

Structured coaching in defined blocks

Coaching is delivered in blocks of three sessions.

Sessions run weekly. Each session builds on the previous, with time between sessions to reflect, test ideas and apply thinking to live situations.

Working in blocks keeps the engagement deliberate and contained, rather than open-ended.

Progress through reflection and iteration

Between sessions, you apply what has been discussed to real decisions and situations.

Each session is used to review what held, what changed and what needs adjustment. The coaching evolves based on situational reality for yo with AI in your business.

At the end of each block, you decide whether to continue, pause or change focus.

Who You Work With

Our executive coaching is delivered personally by Carlo Pepe, founder of Koshima.

Executive coaching requires lived experience, commercial understanding and the ability to hold complex conversations without oversimplifying.

Carlo works directly with leaders and senior professionals who are navigating how AI affects their work, their organisations, and the decisions they are accountable for.

Availability is deliberately limited to ensure each engagement receives the depth and focus it requires.

What Our Coaching Helps With

Sound Judgement

Clear decision-making support where AI introduces uncertainty, pressure and risk.

Executive Focus

Focused thinking grounded in live decisions rather than theory or generic advice.

Durable Decisions

Decisions that hold as context shifts, tools evolve, and expectations change.

Who This Is For

Executive AI coaching is suited for:

Leaders and senior professionals with decision-making responsibility
Executives navigating uncertainty around AI, risk or direction
Individuals who value depth, discretion and focused discussion
People who want space to think clearly rather than consume more information

If you are looking for foundational learning, tool walkthroughs or group-based training, other Koshima offerings will be a better starting point.

Taking The Next Step

If Executive AI Coaching feels appropriate for where you are right now, the next step is a short conversation to understand your context and determine whether this format is the right fit. If it is, we will outline how a coaching block could be structured.

If not, we will recommend a more suitable starting point.

Start a conversation