Engagement

Who the executive AI readiness engagement is for

The leaders the site names: CEO or president, board member, COO, and CFO or strategy lead. Working advisory, not executive education.

Colin Dowling

The four seats the site names

This is not executive education. It is working advisory for leaders who have been told — or already know — that their AI posture is a strategic liability. The homepage names four:

Above the Chief AI Officer layer

The site describes the engagement as executive alignment above the Chief AI Officer layer. A Chief AI Officer or Head of Innovation is responsible for execution. The question the FAQ answers is whether the C-suite and board are asking the right questions, and whether that leader is executing against a framework or a mandate with no guardrails.

The same FAQ says you work directly with a senior practitioner from intake to delivery. That practitioner is Colin Dowling.

Where the published offer sits

The sequence, the five deliverables, and the three fixed fees are on the advisory page. Solo Executive is $20,000, Leadership Trio is $45,000, and Full C-Suite is $75,000. The 15-minute roadmap session is separate, and the session page says it is not a condition of that engagement.

Questions

We already have a Chief AI Officer — or a Head of Innovation. Do we still need this?

Possibly the most common situation we encounter — and one of the most useful applications of this engagement. A Chief AI Officer or Head of Innovation is responsible for execution. What this engagement addresses is executive alignment above that layer: whether the C-suite and board are asking the right questions, whether strategy is being set at the leadership level rather than delegated entirely to a single internal champion, and whether the organization has a coherent framework that the CAIO is executing against — or just a mandate with no guardrails. Many CAIOs have told us privately that the biggest obstacle to their work is the absence of genuine executive conviction at the top. This engagement fixes that. It also gives your innovation leader something to point to when they need air cover.

We already have some AI initiatives underway. Is this still relevant?

Often more relevant. Most organizations running AI initiatives are doing so without a clear outcomes framework, without defined ownership, and without a coherent view of how the pieces fit together. The Readiness Assessment is specifically designed to diagnose exactly that — where you have real momentum versus where you have the appearance of progress. If your pilots aren't converting to enterprise-wide impact, that's a leadership and governance problem, not a technology problem. That's what we fix.

How is this different from hiring a big consulting firm to do our AI strategy?

Large firms send a senior partner to sell the work, then hand it to a team of analysts you've never met. The thinking you're paying for gets diluted before it reaches you. This engagement is different by design — you work directly with a senior practitioner from intake to delivery, and the strategy is built around your business, not adapted from a template. You also get a fixed fee and a fixed timeline. No billable hour surprises, no scope drift, no 200-page deck that sits unread until the next planning cycle.

How much of our team's time does this require?

We've designed the engagement to be light on your calendar by intention — executives don't have 10 hours a week to give a consultant. For the Solo Executive engagement, expect roughly 4–5 hours of your time across the full 30 days: the initial intake session, one or two working sessions during the strategy build, and the final delivery walkthrough. For the Leadership Trio and Full C-Suite tiers, individual executive time stays similar — the additional time is in the cross-functional alignment sessions, which are structured and facilitated so they don't sprawl.