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Executive AI Coaching

Get time back for the work that needs you.

One-to-one AI coaching for founders, CEOs and COOs. Build practical ways to prepare for meetings, work through business information and follow up on commitments, with your judgement guiding the results.

Book a 30-minute call with Sid How coaching works

We’ll discuss where your week goes, what you’ve already tried and where practical support could help.

A full working day leaves little room to rethink how you work.

You prepare for meetings, find the background, write the follow-ups and keep track of what you promised. Even with a capable team, a surprising amount of coordination ends up with you.

You may already use AI for the occasional draft or question. The next step is making it useful in the flow of your day, without giving yourself another system to maintain.

We work with you to build and practise useful workflows around your responsibilities. You learn how to run them, assess the results and adapt them as your needs change.

How we work together

Four weekly sessions, plus an optional follow-up.

  1. Discovery / Before we begin

    Start with your responsibilities.

    A short questionnaire helps us prepare around your role, tools and priorities. You bring your work and your questions; you do not need a technical brief or a list of AI ideas.

  2. First session / 1 hr 45 min–2 hours

    Build the foundations together.

    The longer first session combines discovery, appropriate setup and work on an initial useful workflow. We explain the approach as we go and give you time to practise.

  3. Three weekly sessions / 1 hour each

    Apply and refine it through real work.

    Over the next three weekly sessions, we refine what you have tried and develop further workflows around your priorities. Between sessions, you put them to use and bring back questions, examples and anything that needs attention.

  4. Optional follow-up / 30–45 min

    Come back for follow-up or support.

    An optional fifth session is included a few weeks later. Use it to review progress, address questions or get support with the workflows you have been using.

Make room in your working week.

Your priorities shape the coaching.

Walk into meetings with the context at hand.

Bring your agenda, previous notes and relevant documents into a concise brief. Learn to review open questions and decide what needs your attention.

Get the follow-up ready to review.

Turn meeting notes and your instructions into a draft covering decisions, actions and next steps. Refine the message before sending it.

Review commitments in one place.

Bring agreed actions from selected notes and updates into a weekly review. Check owners, dates and outstanding questions, then decide what to follow up.

Work with the information your day depends on.

Your calendar, meeting notes and business documents can provide useful context for these tasks. We help you decide what to use and explain any proposed connections before setup. We work with your existing subscriptions, permissions and company policies to help with setup, and help craft the initial context documents to get you started.

More capacity, with the capability to keep building on it.

Useful workflows you can run yourself.

Keep applying what you have practised to recurring work. Understand how the workflows operate and how to adapt them as your responsibilities change.

Confidence grounded in practice.

Learn how to give AI useful context, check its work and recognise when a task needs your judgement. Build a clearer sense of where it can help you.

Personal guidance to refer back to.

Personalised guides help you repeat what was covered. A private closing report captures progress, remaining barriers and useful opportunities to explore next.

In practice

Executive AI coaching in practice.

01 / Founder & CEO

A personal AI chief of staff for a busy founder

A personalised morning brief bringing email, calendar and priorities together before the working day begins.
02 / Business founders

Turning order emails into a shared view of the business

A shared customer and order dashboard, with hourly email updates and daily briefs showing what needs attention.
In practice / The full story
Case study / 01 · Founder & CEO

Helping a founder bring priorities into focus

Our work with the founder and CEO of a consumer brand focuses on applying AI to the responsibilities of leading a business: understanding what needs attention, finding relevant information and preparing for the work ahead.

01

Putting AI into practice

The founder was already using AI across several projects. What they wanted was a manageable set of priorities, rather than another long list to work through. Through individual coaching, we began organising the setup around their responsibilities and how they preferred to work.

During the first session, we created a dedicated workspace with business context and instructions pointing to relevant information in existing tools. We also connected task management and set up a weekday morning briefing.

An initial briefing brought together information from emails and the calendar, giving the founder a practical example of how AI could surface what needed attention. The focus was on making that information useful for deciding where to spend their time, rather than adding another summary to read.

02

Extending what’s possible

Alongside the coaching, we are configuring workflows around the founder’s working week, with review steps before information is shared or changes are made.

The aim is to reduce the effort involved in gathering context and organising work, creating more room for leadership, planning and judgement.
In practice / The full story
Case study / 02 · Business founders

Helping founders bring everyday operations into clearer view

Our work with the founders of a small consumer products business focuses on coordinating the work they handle together: keeping track of customer orders, understanding what has changed and deciding who needs to act next.

01

Putting AI into practice

Through hands-on guidance, we helped the founders bring their emails and order information into their AI setup. We worked with their existing tracker and real customer correspondence, so the session centred on the orders they were already managing.

During the first session, they used AI to review open orders and compare their tracker with recent emails, surfacing potential status changes and discrepancies for review. They also set up daily briefings designed to bring together priorities from their inboxes, calendars and order information.

This gave them a practical starting point for asking what had changed on an order and what needed attention. We also worked through how to make responsibilities clearer, including assigning a primary owner and tracking individual tasks.

02

Extending what’s possible

Alongside the training, we helped establish shared tracking and create a visual dashboard from their existing order information.

The aim is to give the founders a clearer view of the work they manage together, with less effort spent piecing together updates and checking who is handling the next step.

The engagement is ongoing, with the founders testing these workflows in their working week and bringing questions back to subsequent sessions. The focus is on building capability they can keep using and adapting as the business evolves.

A few practical questions

Do I need experience with AI?

No. We work from your starting point. If you already use AI, we build on your current habits and focus on recurring work you still handle manually.

How much time should I set aside?

There are four weekly sessions. Allow one hour and 45 minutes to two hours for the first session, then one hour for each of the next three. The optional fifth session is 30–45 minutes a few weeks later. You will also need time to try the workflows in your normal work between sessions.

Will this work with my existing tools?

We review your tools, subscriptions and access before committing to a particular workflow. You provide your own approved AI account and subscription; we help identify the appropriate setup.

How do you handle confidential information?

Before coaching, we agree which information and tools we’ll use and who needs access. We can start with screen-sharing, selected documents or anonymised examples.

You use your own approved accounts. We explain any proposed connections and access requirements before setup. Recordings are optional and agreed in advance.

We ask for your permission before using your work in examples or materials shared outside the engagement.

Will AI send messages or make decisions for me?

We establish appropriate review steps. Drafts and recommendations support your work; you decide what to approve and act on.

Is coaching remote?

Coaching is primarily online, with in-person options in Vancouver and Auckland.

What if I need a custom tool or more support?

We identify what is practical within the coaching and explain when additional development is needed. Custom builds and ongoing support are scoped separately.

What would you like to spend less time doing?

Bring a recurring task, a part of your week that takes too much attention or a question about where to start.

In a 30-minute call, Sid will discuss your responsibilities, what you’ve already tried and whether Executive AI Coaching fits your needs.

Book a 30-minute call with Sid

Want to bring your team into this? Explore Team AI Enablement. ↗