Welcome back to the FNDN Series, where we continue our deep dive into startup people and reward practices, with industry leaders from across the startup world. In our conversation with Adam Weber, Executive Coach to CEOs, Chief People Officers, and other C-suite leaders, we unpack what it truly takes to thrive at the executive level. From the five signals of great executives to navigating dysfunction when the CEO is part of the problem, Adam shares the discipline and intentionality behind senior leadership — and what aspiring CPOs need to start building today.

Chapters:

00:00 Introduction to the FNDN Series
01:05 Guest Introduction: Adam Weber
01:27 The Current Landscape for CPOs on Executive Teams
03:58 Overcoming Imposter Syndrome as an Executive
05:09 Preparing for Pushback Before the Meeting
06:34 Tying People Initiatives to Business Priorities
07:14 The Transition from VP of People to CPO
08:03 The Risk of Over-Softening at the Executive Level
10:23 The Five Signals of Great Executives
13:42 Navigating Dysfunctional Executive Teams
15:08 When the CEO Is the Problem
17:38 Coming to the CEO with Solutions, Not Just Problems
22:54 How to Script Difficult Conversations with the CEO
24:00 Leadership Is a Discipline: Don't Bury the Lead
27:26 How to Prepare for the Path to Executive Leadership
30:46 Taking Bold Swings and Standing Behind Them
36:08 The Evolving Remit of the CPO and AI Transformation
41:31 Knowing When to Say No to Expanding Your Function
43:22 The Human Element That AI Can't Replace
49:17 Final Words for Aspiring People Leaders

Connect with Adam Weber

Visit: https://adamweber.co https://linkedin.com/in/meetadam/

Resources Mentioned

People Mentioned: Christine Song — cited as an example of a CPO who says the hard things out loud Sarika — People leader responsible for AI workforce transformation Benjamin Langner — Guest on a previous FNDN episode discussing what not to use AI for

Quote Referenced: Danny Meyer, CEO of Shake Shack — "Business is problems."

Events: Startup People Summit 2026 — Sign up to the waitlist at startupeoplesummit.com

More FNDN Episodes:

Spotify: https://open.spotify.com/show/4GeBIeZOKrFxG1oiiPxmiM 
Apple Podcast: https://podcasts.apple.com/us/podcast/fndn-series/id1794263484

CPO, ChiefPeopleOfficer, ExecutiveLeadership, PeopleOperations, StartupLeadership, ExecutiveCoaching, LeadershipDevelopment, FiveSignals, CandorAtWork, ExecutivePresence, StartupCompensation, PeopleAndCulture, AITransformation, WorkplaceLeadership, CPORole, LeadershipDiscipline, HRLeadership, StartupPeople, CareerGrowth, StartupBestPractices