The honest take
The thing most people get wrong here is treating these like a ladder. They're not. They're three different shapes of work, and the right one depends on whose work you're actually trying to move forward.
Coaching is for the individual leader. You. Your decisions. Your blind spots. Workshops are for the team. The rollout. The culture. The skill atrophy you can feel happening across multiple people. Fractional CAIO is for organizations that have already worked with me in coaching or a workshop, decided the relationship works, and want me embedded in their strategy across multiple months. Each one is a better answer to a different question.
How to choose
Pick Executive Coaching if...
- You have one specific decision to make or one rollout to pressure-test
- You want a thinking partner for your own leadership challenges
- Budget is tight and you want to prove value before any larger commitment
- You're not sure yet whether the problem is strategic or operational
- The work is yours, not your team's
Pick a Team Workshop if...
- You're rolling out AI to a team or department right now
- Your team is using AI in ways that worry you (skill atrophy)
- Adoption is stalling and you can't fully explain why (hesitation gap)
- You need a shared language across multiple people
- The work is your team's, not yours alone
Fractional CAIO is right if...
- You already have a coaching or workshop relationship in place
- You need embedded strategic AI leadership across multiple months
- Your board is asking questions and you don't have clean answers
- You have 50 or more employees and AI is touching multiple departments
- You've been referred or invited to a fractional conversation
Pricing comparison
| Executive AI Coaching | AI Team Workshops | Fractional CAIO | |
|---|---|---|---|
| Cost | $300/session · $800 sprint (3) · $2,000 quarter (8) | $7,500 per engagement ($3,750 launch offer for first 10 companies) |
By invitation · From $1,750/mo (Advisor) or $3,500/mo (Operator) |
| Format | 60-min 1-on-1 video sessions | Assessment + 3-hour live workshop + full PDF report | Ongoing monthly engagement |
| Who it's for | Individual leaders | Teams, departments, or small companies (up to 20 participants) | Orgs already in a coaching or workshop relationship |
| Commitment | None | One-time per workshop | 6-month initial term when accepted |
| Availability | Open booking | Open booking | Limited · by referral |
| Nonprofit pricing | $200/session | Quotable on request | Standard rate |
| Bilingual (English/Spanish) | Yes | Yes | Yes |
The way this usually works
So here's the path most organizations actually take. Someone reaches out for coaching because they have a specific question, or someone books a workshop because they have a team rollout. We do that work, and it's useful on its own. By the time we've done it, both of us know whether there's more to do together, and what shape that might take.
If the natural next thing is more coaching, we do that. If it's a workshop for the broader team, we do that. If the relationship has earned its way into a fractional arrangement, we have that conversation when capacity allows. None of it requires you to figure out the long path on day one. We figure it out by working together.
Frequently asked questions
No. Coaching is pay-per-session with no retainer. Workshops are a one-time engagement for a team. Neither requires an ongoing commitment. Fractional engagements have a 6-month initial term when they happen, but new ones are limited and added by invitation, not by application.
Yes for one focused conversation. If the team is the focus though, a team workshop usually does more in three hours than three coaching sessions can. Coaching is built for an individual leader working through a decision. Workshops are built for groups working through a rollout or a culture issue.
That's how new fractional engagements happen. The coaching or workshop builds the context, and a fractional conversation comes out of it naturally when there's a fit. The context carries forward, so you're never starting from scratch.
A lot of organizations run both. The right order depends on which problem is louder. If your team is resisting AI, start with The Hesitation Gap (leadership team) so the people carrying the rollout get aligned. If your team is adopting AI fast and you're worried about skill atrophy, start with AI Without Atrophy (broader team). Each engagement is $7,500 (or $3,750 if you're one of the first 10 launch companies). Either engagement works on its own. The combination compounds.
Ready to figure out which path fits?
This is a free 30-minute call. You tell me where your organization is right now and what's actually slowing you down. I'll tell you honestly whether a coaching session, a team workshop, or something else is the right next step. If none of them are a fit, I'll tell you that too.
Book a Free Discovery Call30 minutes. No pitch. We'll figure out together what fits.