“HR Heretics” | How CPOs, CHROs, Founders, and Boards Build High Performing Companies

Kelli and Nolan tackle a listener's frustration with a painfully slow reorg process, diving into the eternal tension between perfect planning and actually running the business. When HR and legal reviews stretch into week four, should you keep waiting for perfection or pull the trigger? Towards the end of the episode, Kelli and Nolan get into brass tacks offering tactical timelines to execute a reorg based on hypothetical examples.

*Email us your ‘Dear Heretics’ questions: [email protected]

**For coaching and advising inquire at https://kellidragovich.com/

HR Heretics is a podcast from Turpentine.

—Support HR Heretics Sponsor: Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics —

KEEP UP WITH NOLAN + KELLI ON LINKEDIN

Nolan: https://www.linkedin.com/in/nolan-church/

Kelli: https://www.linkedin.com/in/kellidragovich/

—

Timestamps:

(00:00) Intro

(00:19) The Reorg Dilemma

(00:56) Challenges in Big Companies

(03:00) Balancing Perfection and Speed

(04:43) HR & Legal Risk

(08:55) Sponsor: Metaview

(10:49) Employment Lawyers’ Limitations

(12:33) Intellectual Trap

(13:28) Workshopping Different Scenarios

(15:23) Wrap

Tom Clayton, COO of Peek, shares his unconventional playbook for building world-class teams. From his data-driven "employee attribute chart" to his rule of "don't be a brand b***h," Tom breaks down how he's scaled companies from 50 to 2000+ employees.

He dishes on everything from why he sends champagne to candidates' hotel rooms to why he encourages employees to quit and start their own companies.

If you’re listening on podcast platforms, be sure to check out our Substack or YouTube channel to see Tom’s framework slides onscreen:

Substack: https://hrheretics.substack.com/p/smart-hiring-with-tom-clayton

YouTube: Smart Hiring with Tom Clayton

*Email us your questions or topics for Kelli & Nolan: [email protected]

For coaching and advising inquire at https://kellidragovich.com/

HR Heretics is a podcast from Turpentine.

—

📰 Be notified early when Turpentine's drops new publication: https://www.turpentine.co/exclusiveaccess

Support HR Heretics Sponsor:

Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

KEEP UP WITH NOLAN + KELLI ON LINKEDIN

Nolan: https://www.linkedin.com/in/nolan-church/

Kelli: https://www.linkedin.com/in/kellidragovich/

—

RELATED LINK:

The Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to go from $0 to $100 Million: https://www.amazon.com/Sales-Acceleration-Formula-Technology-Inbound/dp/1119047072

—

TIMESTAMPS:

(00:00) Intro(00:37) The Employee Attribute Chart Explained(03:41) Contextual Attributes(05:00) Answering with Cues vs. Direct Questions(10:46) Training Others on the Attribute Chart(11:28) The Value of Multiple Interviews(13:15) Emotional Investment in the Group(14:17) Speed Dating Analogy for Interviews(14:27) Sponsor: Metaview(16:21) Expediting the Interview Process(17:03) Job Simulations and Work Trials(18:36) Difficulties with Senior Exec Simulations(20:39) The Importance of the "Mock Exec Meeting"(21:57) Making Intangibles Tangible(22:54) Evolution of Team Building Attributes(23:09) Team Building and Outreach(26:47) Don't Be a "Brand B***h"(29:11) The Value of Personal Touches(32:31) Sustaining Great Teams During Hyperscale(35:00) Meta's Performance Process(38:39) Encouraging Entrepreneurship(42:23) Altruism in the Industry(42:31) Wrap

Kelli and Nolan unpack the delicate art of layering – that awkward moment when someone gets a new boss – while calling out the pitfalls of secret searches and celebrating the often-forgotten heroes of early startup days. Equal parts tactical advice and therapy session for growing companies.

*Email us your questions or topics for Kelli & Nolan: [email protected]

For coaching and advising inquire at https://kellidragovich.com/

HR Heretics is a podcast from Turpentine.

—

📰 Be notified early when Turpentine's drops new publication: https://www.turpentine.co/exclusiveaccess

Support HR Heretics Sponsor:

Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

KEEP UP WITH NOLAN + KELLI ON LINKEDIN

Nolan: https://www.linkedin.com/in/nolan-church/

Kelli: https://www.linkedin.com/in/kellidragovich/

—

TIMESTAMPS:

(00:00) Intro(00:13) Layering Question on Dear Heretics(02:06) Initial Thoughts on Layering(02:58) Human Aspect of Layering(03:43) Importance of Coaches & Advisors(04:00) New Hires vs Existing Employees(07:16) Confidential Search on Layering(10:08) Sponsor: Metaview(12:02) Handling Layering: CEO/CPO Perspective(14:13) Expanding Roles in Startups(16:00) New Executives and Fail States(16:57) The Shepherd Role of a Leader(17:18) The Layered Employee's Perspective(18:05) Two Paths: Spiteful vs. Gracious(20:18) Building Something Bigger Than Yourself(20:59) Maturity Matters(21:20) Wrap

Think AI is just about robots summarizing your emails? Think again.

Metaview co-founder and CEO Siadhal Magos reveals how AI's real impact in an org is making sense of workplace conversations, performance reviews, and all the messy human stuff that HR deals with.

Start recognizing the opportunities presented by ‘unstructured data’ to transform HR from subjective guesswork to data-driven decisions, without losing the human touch.

*Email us your questions or topics for Kelli & Nolan: [email protected]

For coaching and advising inquire at

https://kellidragovich.com/

HR Heretics is a podcast from Turpentine.

—

📰 Be notified early when Turpentine's drops new publication: https://www.turpentine.co/exclusiveaccess

Support HR Heretics Sponsor:

Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

KEEP UP WITH SIADHAL, NOLAN + KELLI ON LINKEDIN

Siadhal: https://www.linkedin.com/in/siadhal/

Nolan: https://www.linkedin.com/in/nolan-church/

Kelli: https://www.linkedin.com/in/kellidragovich/

—

TIMESTAMPS:

(00:00) Intro(00:52) Why Unstructured Data Matters in the AI Era(02:18) Frustrations with Structured Data Entry(03:24) Making Sense of Data at Scale (04:01) Data is Everywhere(04:55) AI's Ability to Read Data(06:25) Moving Towards Objectivity with AI(07:16) Using Digital Exhaust for Team Building(09:01) Sponsor: Metaview(11:13) What if the AI Reads Wrong?(11:56) Human in the Loop(12:24) Levels of AI Autonomy(14:54) Problems, Missteps, and Best Practices(15:44) The Gradient of AI Implementation(16:47) AI and Human Nuance(17:33) Capturing Unstructured Data is the Foundation for AI (19:13) Garbage in, Garbage out(19:22) Wrap

Nolan and Kelli talk about the culture shock of moving from corporate behemoths to the startup wild west. They share battle-tested wisdom on surviving the transition - from mastering the art of founder relationships to embracing the (sometimes brutal) transparency demands of startup employees.

Along the way, they reveal how corporate luxuries like two-hour gym breaks get replaced by the exhilarating but exhausting reality of building something from scratch.

*Email us your questions or topics for Kelli & Nolan: [email protected]

For coaching and advising inquire at https://kellidragovich.com/

HR Heretics is a podcast from Turpentine.

—

📰 Be notified early when Turpentine's drops new publication: https://www.turpentine.co/exclusiveaccess

Support HR Heretics Sponsor:

Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

KEEP UP WITH NOLAN + KELLI ON LINKEDIN

Nolan: https://www.linkedin.com/in/nolan-church/

Kelli: https://www.linkedin.com/in/kellidragovich/

—

TIMESTAMPS:

(00:00) Intro(01:30) Understanding Startup Culture(03:26) Founder Relationship Importance(03:52) Pre-Start Relationship Building(05:35) Importance of Being "One with the People"(07:04) Danger of Being Viewed as the Enemy(08:25) Startup Employees Being Smart & Critical(09:19) Connecting with Early Employees(09:30) Sponsor: Metaview(11:01) Understanding "Sacred Cows"(12:28) Tactical Advice - Meeting Everyone(12:57) Goals of Meeting Everyone(14:00) Context Switching Exhaustion(14:25) Energy Management Importance(15:24) Non-Negotiable Self-Care(16:00) Wrap Up

Kelli and Nolan start with a heartfelt discussion about LA fires before diving into the art of handling CEO mandates for attrition targets.

They reveal insider strategies for transforming harsh directives into meaningful performance frameworks, while warning against becoming the dreaded "person of no."

*Email us your questions or topics for Kelli & Nolan: [email protected]

For coaching and advising inquire at

https://kellidragovich.com/

HR Heretics is a podcast from Turpentine.

—

📰 Be notified early when Turpentine's drops new publication: https://www.turpentine.co/exclusiveaccess

Support HR Heretics Sponsor:

Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

RELATED PODCAST:

KEEP UP WITH NOLAN + KELLI ON LINKEDIN

Nolan: https://www.linkedin.com/in/nolan-church/

Kelli: https://www.linkedin.com/in/kellidragovich/

—

TIMESTAMPS:

(00:00) Intro(01:17) Offer of Support for the California Wildfires(03:44) Dear Heretics(04:00) Question on Mandated Attrition Targets(05:15) Contextualizing Performance Targets(06:32) Genesis of these Performance Discussions(07:00) Examples of Poor Implementation: Tesla's RIFs(08:03) Sponsor: Metaview(10:05) RIFs versus Performance(10:42) How to respond to a CEO who says fire the bottom 5%(12:40) The Importance of Defining 'Why'(13:23) CEOs and the complexity of execution(14:00) Reframing the Problem for CEO's(14:31) The tactical anxiety of HR leaders(15:42) Pre and Post Pandemic Environments(16:23) The danger of being the "no" person/team(17:18) Wrap

Colin Zima, former Looker exec turned Omni CEO, reveals how he runs a 65-person Series A startup with no HR or G&A team. Learn why he believes in minimal bureaucracy, why founders should do the "dirty work," and what really breaks after a Google acquisition.

*Email us your questions or topics for Kelli & Nolan: [email protected]

For coaching and advising inquire at https://kellidragovich.com/

HR Heretics is a podcast from Turpentine.

—

📰 Be notified early when Turpentine's drops new publication: https://www.turpentine.co/exclusiveaccess

Support HR Heretics Sponsor:

Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

KEEP UP WITH COLIN, NOLAN + KELLI ON LINKEDIN

Colin: https://www.linkedin.com/in/colinzima

Nolan: https://www.linkedin.com/in/nolan-church/

Kelli: https://www.linkedin.com/in/kellidragovich/

—

CHECK OUT:

Omni: https://omni.co/

—

TIMESTAMPS:

(00:00) Introduction(01:44) No G&A at Omni(04:50) Learning by Doing(09:10) Maximizing Roles (10:23) The Need for G&A (12:53) Sponsor: Metaview(14:49) Benefits of Doing the Work(15:32) Hiring a People Leader(18:19) Contractors vs FTEs(20:39) In-Office vs Remote (23:08) Homogenous Culture (26:25) Recruiting for Non-Networked People (29:31) Performance Management (32:24) Sales Ops and Performance (34:47) Unique Recruiting at Omni (37:00) Looker Acquisition by Google(42:24) Wrap

From Square to Nextdoor, Bryan Power reveals why copying Big Tech's playbook might be your biggest mistake.

Find out why Square banned hiring from the payments industry while building a payments company. Discover how conventional wisdom about senior talent can become startup kryptonite and why the safe choice isn't always the smart choice.

Bryan Power is a veteran Silicon Valley People executive who's shaped talent strategy at tech giants like Google and Yahoo, built Square from 150 employees, and now leads People at Nextdoor where he champions innovative approaches to hiring and leadership development.

*Email us your questions or topics for Kelli & Nolan: [email protected]

For coaching and advising inquire at https://kellidragovich.com/

HR Heretics is a podcast from Turpentine.

—

📰 Be notified early when Turpentine's drops new publication: https://www.turpentine.co/exclusiveaccess

Support HR Heretics Sponsor:

Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

KEEP UP WITH BRYAN, NOLAN + KELLI ON LINKEDIN

Bryan: https://www.linkedin.com/in/bryanpower

Nolan: https://www.linkedin.com/in/nolan-church/

Kelli: https://www.linkedin.com/in/kellidragovich/

—

CHECK OUT:

Nextdoor:

https://nextdoor.com/

—

TIMESTAMPS:

(00:00) Intro

(00:48) Nextdoor Leadership Transition

(02:10) Founder's Mentality & Return

(04:03) Six Years at Nextdoor - Career Journey

(05:29) Growth vs. Turnaround Experience

(07:59) The False Signal of Company Logos

(10:29) Square's Early Days & Recruiting

(12:25) Leadership Training at Square

(15:07) Sponsor: Metaview

(17:01) Culture and Training Truths

(21:30) Innovation vs. Industry Experience

(25:59) The Pattern Matching Trap

(29:39) Talent Density Discussion

(33:58) Performance Management & Up-leveling

(40:34)) Big Company vs. Startup Dynamics

(43:07) Aligning with Different Leadership Styles

(47:14) Wrap

Happy New Year from HR Heretics!

Together, we've built something extraordinary: a community of forward-thinking HR professionals who dare to question the status quo, welcome straight talk, and thrive on healthy debate.

In today's special year-end episode, we're sharing some of our top moments, most controversial takes, and the conversations that simply blew our minds with new approaches to people, hiring, managing, and shaping the culture of high performing teams. Think of this as your ultimate HR Heretics highlight reel – where spicy takes meet practical wisdom.

So whether you're a longtime heretic or just discovering us today, buckle up. Come January 2nd 2025, we'll be back with new guests.

*Email us your questions or topics for Kelli & Nolan: [email protected]

For coaching and advising inquire at https://kellidragovich.com/

HR Heretics is a podcast from Turpentine.

—

Support our Sponsor:

Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

—

KEEP UP WITH NOLAN + KELLI ON LINKEDIN

Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/

—

LINKS:

Molly Graham: https://open.spotify.com/episode/3gegNOB1RSWuKofaWcjYWS?si=AGhfhyhgRsu8LSUlN7wtjg

Tomas Tungusz: https://open.spotify.com/episode/1B4aYWnV9pJkcQuCgq1tTy?si=d-iRpEMrQX62JwiKQi9nGg

Vijay Pendakur: https://open.spotify.com/episode/4ccUUyNPVUjBEc3V9h1SEf?si=LLhIXfbkSMaWaIyPnfHmfA

Patty McCord: https://open.spotify.com/episode/2nHxmrGnGFJ23ropYPc4YE?si=9WzJ1VdnQjS4vlS7kbBy8A

Andy Price: https://open.spotify.com/episode/2LmfYrgz58M1bjU4kj8t7i?si=UpCAZwNkR_SVg-29AY-_Zg

Colleen McCreary: https://open.spotify.com/episode/0WuLzUYeDaPIsOTbtTCZFD?si=EnzuH3v-S9SO1zTCBvBwng

Brett McQueener: https://open.spotify.com/episode/666pMzHni919QMMhe4NPWQ?si=vRyeGi3XSEuHaEjKZQFVew

Matt Oberhart: https://open.spotify.com/episode/6lYnLlZrBGNZOdw97NoElB?si=vwJTyZp4SIyQzgDQY6eOFA

LJ Brock: https://open.spotify.com/episode/0Jj5U59L703HKVZNg9QJef?si=5Oz5FpnDT9yHO2YekmY9jw

DHH: https://open.spotify.com/episode/6AD2rSoIi9gF0WlZ3gqoz3?si=Km774GZJSraHW4ljuI0f-g

Peterson Conway: https://open.spotify.com/episode/5jQ2TsSMMmlWuJ3vAayHoR?si=SdnrYwnZQQSo4f5tR2XLfw

--

TIMESTAMPS:

(00:00) Intro

(00:15) Molly Graham

(00:53) Tomas Tungusz

(02:03) Vijay Pendakur

(03:15) Patti McCord

(04:44) Andy Price

(05:50) Colleen McCreary

(06:41) Brett McQueener

(07:49)  Matt Oberhart

(08:44) LJ Brock

(09:46) DHH

(10:56) Peterson Conway

(12:21) Nolan's Best

(14:14) Kelli's Best

(15:02) Wrap

(15:08) Sponsor: Metaview

It’s been quite a year!

Kelli and Nolan bare it all in their 2024 wrap-up. Get their must-read books, binge-worthy podcasts, and raw personal journeys - including Kelly's identity crisis and Nolan's toughest year yet. Plus, hear why 2025 might be the year to go 'risk on' and why your company's headcount could be holding you back.

No fluff, just real talk from two HR leaders who've been there.

*Email us your questions or topics for Kelli & Nolan: [email protected]

For coaching and advising inquire at https://kellidragovich.com/

HR Heretics is a podcast from Turpentine.

—

📰 Be notified early when Turpentine's drops new publication: https://www.turpentine.co/exclusiveaccess

Support HR Heretics Sponsor:

Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

KEEP UP WITH NOLAN + KELLI ON LINKEDIN

Nolan: https://www.linkedin.com/in/nolan-church/

Kelli: https://www.linkedin.com/in/kellidragovich/

—

TIMESTAMPS:

(00:00) Intro

(00:53) Reflections on 2024

(07:24) Best of 2024 - Books

(11:13) Best of 2024 - Podcasts

(14:47) Sponsor: Metaview

(16:20) The Real Talk: Our Raw 2024 Stories

(19:16) Bold Predictions and Why 2025 Will Hit Different

(28:45) That’s a Wrap 🎁