Where is AI Good Enough? The Future of Coaching at the Executive Level

The question senior HR leaders are really asking

AI coaching tools are scaling fast. The cost savings are real. The accessibility is real. But the real question isn’t being asked plainly enough:

At the senior leadership level --- is AI actually good enough? And if not, what does that mean for your organization?

Join Berman Leadership Development and a curated group of 16 senior HR executives for an intimate, off-the-record lunch conversation at Del Frisco's Steakhouse in the Seaport on May 28th, 12:00--1:30 PM.

This is not a panel. It's not a webinar in disguise. It's a table of peers --- CHROs, CPOs, and Heads of Talent and Executive Coaching --- having the kind of honest conversation that rarely happens in public.

Beyond “Is AI impressive?” to “Is it good enough?”

We're not here to debate whether AI is impressive. It is.

We're here to talk about what it can and can't do --- specifically at the levels where the stakes are highest and the answers are rarely clean.

The framing: Is AI good enough, and do the cost and scalability benefits justify the tradeoff?

The real tradeoffs at the executive level

A sharper lens, not a longer to-do list

• A working map of the current AI coaching landscape: what the tools actually do well, where they break down, and which organizational factors determine the difference
• A practical framework for thinking about tiered coaching models across leadership levels, including where AI is genuinely good enough and where the executive exception applies
• Peer perspectives from senior HR leaders in Boston navigating the same tradeoffs at scale
• A clearer, more confident point of view to bring back to your leadership team on AI vs. human coaching decisions
• Unfiltered insight from peers on the real-world state of AI coaching: what's working, what's not, and what's on the horizon

Your hosts

Dr. Stephen Dwight — Chief Talent Officer, Pharmaceutical/Biotech | Stephen has spent his career building leadership capability inside some of the most complex organizations. He brings a sharp, no-nonsense lens to where AI coaching is genuinely useful and where it falls short.

Ellie Eckhoff — Executive Coach & Leadership Team Consultant | Ellie works with senior leaders and executive teams to help them think clearly, align decisively, and lead with impact. She brings deep relational expertise to the question of what human coaching delivers that technology simply cannot replicate.

Dr. Scott Serviss — Partner, Executive and Team Coach | Scott brings a practitioner's perspective grounded in the science of leadership development, helping organizations build the human infrastructure behind high-performing teams.

Hosted by Berman Leadership Development — a trusted partner to senior HR executives

This lunch is designed for a very specific group — and that's intentional.

• ✔ CHROs, CPOs, SVPs of Talent, Heads of Coaching and Leadership Development
• ✔ Companies where tiered coaching decisions have real organizational stakes
• ✔ Leaders who want a peer conversation — not a pitch

Attendance is by invitation only. Space is limited to 16 participants.