Open Coaching Session for Leaders in AI Transformation

You’ve been handed AI adoption, or you’re about to be, and the decision on your desk can’t wait for a full-scope engagement.

This is a fit if you:

• Lead a function, team or program where AI is changing how work gets done: Chief of Staff, VP of People, AI program lead, COO or function head

• Have a specific decision in front of you: a role change, a rollout, a headcount question or a governance gap

• Want an outside read from someone who has worked with both large enterprises and startups

• Have company budget for coaching or professional development

Not quite right? If you need a finished deliverable, see the Role Redesign or AI Adoption Diagnostic packages. If you’re paying for yourself, the Founders & Independent Practitioners session is built for you.

You leave with a clearer decision and a written record of the session that you can share inside your organization.

• A pre-read review: I go through the materials you send ahead of time, so the hour goes to your decision rather than background.

• 60 focused minutes on the AI decision in front of you: what’s really at stake, the options, and the tradeoffs your team may not be anticipating.

• A written summary within [2] business days: the decision as framed, the options we discussed, my recommendation and the next steps.

Why it matters: a summary you can forward turns one conversation into something your leadership can act on, and it documents the coaching for your company’s records.

1. Book your session. Choose a time that works for you. All sessions are held virtually.

2. Complete a short intake. Tell me your role, your organization’s size, and the decision you’re facing.

3. Send your materials 48 hours ahead. This could be a strategy doc, a rollout plan, an org chart, or whatever gives me context. I’ll review it before we meet.

4. Meet for 60 minutes. We spend the full hour on your challenges, not on background.

5. Receive your written summary within [2] business days. It covers my recommendation and your next steps. You’re free to forward it inside your organization.

I’ve spent my career where a new technology meets the people expected to absorb it.

In 2005 I co-founded BlogHer, when blogging was still new and social media norms untrusted and untested. We built frameworks for trustworthy engagement, which I've done with emerging tech ever since. I’ve led global marketing teams at AWS and ConsenSys (blockchain), and in 2024 I co-founded Optionality, a community for experienced professionals exploring new models for work and meaningful careers. I started my career in traditional media (Time Inc, The New York Times Syndicate, Penguin), writing for national publications such as Fast Company and Inc.

Today, through my advisory practice Candor Partners, I work with leaders on a problem I call structural lag: Organizations deploy AI faster than their people and institutions are ready to absorb it. Human Agency Architecture (HAA) is the framework I built to close that gap. It gives leaders a practical way to decide what AI should handle, what people must keep deciding, and how to protect the judgment and development their organizations depend on.

I also convene the AI Operators Exchange, a private working group of senior enterprise operators, and I advise AI organizations on Narrative Positioning and GTM.

Read and connect

• Substack: The Architecture of Work

• Optionality

• LinkedIn