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The Corporate Rules That Need to Go

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Episode 35 Featuring Jessica D. Winder, Chief People Officer, Winder Law Firm

Most of the rules that run your company were never actually designed. They accreted. One person came in late, one person abused a perk, one person made a leader uncomfortable, and a policy got written for everyone to carry from then on. Jessica D. Winder has spent her career as the first HR executive inside companies, which means she is usually the one handed that rule book and asked to enforce it. Her take is blunt. Most of what we treat as normal is not holding culture together, it is quietly holding people back.

In this conversation with host Kim Bohr, Jessica names five outdated leadership rules she thinks should finally be retired, and she has the standing to say it because she implemented most of them herself. Unlimited PTO that she now calls a scam. Annual performance reviews that became theater. Exit interviews that arrive too late to matter. Secret high performer lists nobody on them ever hears about. And the assumption that the only way to grow is to become a manager.

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🎧 LISTEN, Hear Jessica D. Winder’s Full Conversation

Want the full episode? Listen to Jessica D. Winder on Courage to Advance, where she and host Kim Bohr get into the five corporate rules that need to go, why unlimited PTO backfires without a minimum, and the stay interview every leader should be running.

What makes this more than a list of complaints is that every rule she retires comes with a replacement she has actually run. A PTO minimum instead of a cap. Monthly three question check-ins instead of a dreaded annual review. Stay interviews instead of exit interviews. A dual track so your best expert never has to manage people to earn more. Jessica is a practitioner handing over field tested systems, not a critic lobbing hot takes.

It lands at a moment when SparkEffect’s own research shows how much trust inside organizations rests on fairness, clarity, and whether people feel genuinely seen. Jessica’s whole argument, that the rules you tolerate reveal the culture you actually have, is that research made practical. Kim even admits on air that SparkEffect has no PTO minimum and plans to add one.

What You’ll Discover 

  • Why most handbooks are written for the exception, and what to build instead
  • The difference between a legal handbook and a living culture book, and why leaders confuse them
  • Why unlimited PTO can quietly suppress rest, and the one change that fixes it
  • How to run performance feedback so it builds trust instead of eroding it
  • The stay interview, and why it beats both exit interviews and engagement surveys
  • Why not everyone should manage people, and how a dual track keeps your experts
  • The rule leaders defend hardest, and why writing a policy rarely changes behavior
  • How to retire a resented rule without giving your team whiplash
  • A human centered way to think about AI that starts with abundance, not fear

Episode Highlights 

[00:00] The rules we treat as normal. Kim opens on the quiet cost of unquestioned rules and introduces Jessica D. Winder, the HR executive who builds the rule book and then argues most of it should go.

[03:15] A legal handbook is not a culture book. Jessica splits the two cleanly, the handbook as a legal document that changes with the law, the culture book as a living, breathing document reviewed every six months and re-rolled with the team.

[08:46] Unlimited PTO is a scam without a floor. Jessica explains how an unlimited policy she implemented quietly stopped her top performers from taking any time off, and why a required minimum fixes what a cap never could.

[12:27] When performance reviews backfire. Jessica on why reviews are waste without a real feedback loop, how leaders weaponize raw data, and the monthly three question check-in she uses instead.

[20:04] Ask why they stay, not why they left. Jessica makes the case for stay interviews over exit interviews, including the monthly randomizer and the three questions she asks the people she cannot afford to lose.

[25:46] Not everyone should manage people. Jessica calls forced management a witch’s brew and lays out the dual track that lets experts grow without leading people, plus the leadership pipeline gap coming behind it.

[29:47] Stop writing policies for one person. Jessica names the rule leaders defend hardest, the belief that a new policy fixes one person’s behavior, and why that is magical thinking.

[33:49] AI and the abundance mindset. Jessica, from inside the legal world, on where AI belongs, where it does not, and how it can free leaders to spend more time being human instead of less.

[39:06] What courage to advance means to Jessica. Jessica closes on saying the hard thing with respect, and on being good trouble, shaking things up because you believe they could be better.

Key Takeaways for HR and Talent Leaders

  1. Most workplace rules were written for the exception, and everyone else pays for them. Before you add a policy, ask whether you are writing it for one person. If you are, go talk to that person. Audit your handbook for rules that now apply to almost no one and retire them first.
  2. Unlimited PTO suppresses rest unless you set a minimum. When nothing is use it or lose it, high performers stop taking time and managers invent unwritten norms about who gets to rest. Require a floor, at least two weeks, and have HR flag anyone who has not taken it.
  3. Stay interviews give you exit interview intelligence while you can still act on it. Ask the people still here why they stay and what would make them leave. Run it one to one, a few people a month, and you learn more than any survey or late exit interview will ever tell you.
  4. Growth should not require becoming a manager. Being great at the work does not make someone a great people leader, and forcing the path burns people out. Build a dual track to principal or expert level so your best individual contributors can rise without managing anyone.

About Our Guest

Jessica D. Winder, SPHR, SHRM-SCP, is a Chief People Officer, speaker, author, and founder of Hidden Gem Career Coaching. Known for saying what everyone else is thinking, she challenges outdated workplace norms with honest, practical conversations about leadership, careers, AI, compensation, and company culture.

With more than 13 years in executive HR, Jessica has advised leaders through growth, change, and the messy realities of managing people. She currently serves as Chief People Officer at The Winder Law Firm. She is the host of the Make It Make Sense podcast and creates content that reaches millions of professionals looking for straight answers about work.

Based in Las Vegas, Jessica is a wife and a mom of two sets of twins, and she believes the workplace does not need more corporate jargon. It needs better leaders.

Connect with Jessica D. Winder 

Notable Quotes 

Jessica D. Winder “I think it’s a scam. And mind you, I have implemented it.”

Jessica D. Winder “A lot of times the culture is made by not what you say. But who are the exceptions?”

Kim Bohr “There is a lot of influencers who don’t hold leadership titles that you need to know who they are, because they’re the ones that are going to help make or break these trust moments inside your organization.”

Kim Bohr “What if the rules we treat as normal are the exact things holding our people back?”

Related Resources 

About Courage to Advance 

Courage to Advance explores how visionary leaders are building the organizations they wish existed, companies that prove business doesn’t have to be dehumanizing. Hosted by Kim Bohr, President and COO of SparkEffect, each episode features executives who refuse to accept that traditional corporate practices are inevitable, sharing the experiments, resistance, and breakthrough results of choosing human flourishing alongside business success. 

Subscribe anywhere you listen to podcasts. You can find links to all platforms HERE! 

Visit: https://sparkeffect.com/sparkeffect-podcast-courage-to-advance/ for free resources and tools. 

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