A Step-by-Step Guide to Creating a Great Leave Experience

Alex Coonce (Chief People Officer) and Patrick Quigley (CEO) from Sidecar Health joined us on The Modern People Leader. We talked about building a strong CEO–CPO partnership, why culture must scale before headcount does, and how companies can become AI-native while staying transparent with employees.----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode287Sponsor Links:🔗 Learn more about Wellthy at wellthy.com/mpl🔗 Book a conversation with Compete at compete.com/mpl----  (06:17) How Alex joined Sidecar Health and the early hiring story(10:46) What Sidecar Health does and how their healthcare model works(16:52) The CEO–CPO partnership and how they built trust working together(17:57) Early disagreements, culture decisions, and navigating leadership dynamics during COVID(20:35) How Patrick’s expectations of the CPO role evolved beyond traditional HR(25:27) Frameworks for understanding the business: market, business model, and leadership dynamics(28:54) Decision-making: when the CPO leads vs. when the CEO steps in(31:32) Building a culture of ownership: “give speeding tickets, not permission slips”(32:25) Navigating uncertainty and employee trust during constant change(34:51) Leading the “people business” alongside the company business(39:53 Leadership changes and how to bring teams along during major org shifts(42:43) Managing leadership transitions and the “Olympic team” mindset for executives(46:43) AI strategy and preparing the organization for the AI era(48:24) Building an AI-native culture through experimentation and tool adoption(50:33) Why AI adoption was driven culturally through the people team, not just engineering(52:30) Operating lean: scaling a company without adding as much headcount(55:03) Rethinking career growth when management roles are fewer in the AI era(56:31) Curiosity, experimentation, and the future of AI adoption in organizations---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Kim Smith from Tilt joined us on The Modern People Leader. We talked about how personalized leave support creates a better employee experience, what managers and HR teams often miss during leave transitions, and how to build a modern leave process that balances compliance, communication, and care.----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode286Sponsor Links:🔗 Learn more about Tilt at hellotilt.com/mplMPL Links:🔗 Go sign up for MPL Build.(05:43) Kim’s Career Story: How Her Own Leave Experience Led Her into Leave Management(10:16) Life on a Two-Person People Team at Tilt(11:02) What Tilt Actually Does: Explaining Leave Administration in Plain Language(12:26) Why Great Leave Experiences Need to Be Personalized, Not Checklist-Based(16:29) The Two Types of Employees Who Show Up During Leave(18:35) What Employees Should Ask Their Manager Before Going on Leave(25:14) A Step-by-Step Walkthrough of Designing a Great Leave Experience(31:15) Kim Reflects on Her Own Leave Experience While Working at Tilt(34:46) Why Knowledge Transfer and Coverage Planning Matter So Much Before Leave(36:15) Why HR Often Resists Personalized Leave Support and How to Rethink It(39:51) How Kim and Janisa Designed the Employee Leave Experience at Tilt(41:59) The “Rule of Five” for Helping Employees Re-enter After Leave(44:30) Balancing Tech and Human Support in Modern Leave Management(47:11) How AI Can Help HR Teams Manage Leave More Effectively---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Melissa Theiss, Head of People Ops at Kit, joined us on The Modern People Leader to break down how HR leaders can build real business acumen using practical frameworks like Track-Racehorse-Jockey, her PeopleOps maturity diagnostic, and a 90-in-90 listening tour. We also walked through how to turn employee feedback into an actionable backlog and use it to shape a people strategy that supports the business first while staying people-centric.----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode285Sponsor Links:🔗 Book a conversation with Compete at compete.com/mpl🔗 Learn more about Wellthy at wellthy.com/mpl🔗 Learn more about Tilt at hellotilt.com/mplMPL Links:🔗 Go sign up for MPL Build.----  Timestamps:(06:51) Melissa’s career path(10:16)Melissa’s work outside Kit and her newsletter, The Business of People(11:45) what Kit does and how MPL uses it(14:50) “How does the business make money?”(15:20) Track-Racehorse-Jockey and how VCs evaluate a business(15:34) Track: market context and competitive landscape(17:56) Racehorse: business model and revenue engine (product-led growth, pricing, AI credits)(19:17) Jockey: leadership team signals and what to assess(20:18) Coaching HR leaders through business jargon and discomfort(22:59) Learning business acumen: newsletters, courses, and choosing an industry you care about(25:21) PeopleOps maturity diagnostic and how it works(25:44) The PeopleOps maturity score, priorities, and avoiding “too much process too early”(29:14) Example areas: compensation philosophy, interview structure, compliance, global workforce basics(31:13) How Melissa built the diagnostic over time(34:05) How often to re-run the diagnostic and keep improving over quarters(37:49) Managing feedback like a product backlog(44:38) Listening tours and what leaders uncover that surveys miss(48:44) The “90 and 90” listening tour structure, questions, and how to scale it past 100+ employees(53:33) Honesty in 1:1s and the value of quieter, thoughtful feedback(54:24) Building a cohesive people strategy from the three inputs(55:27) Weighting trade-offs and why “people-first” can fail if the business is not healthy---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Jessica Zwaan joined us on The Modern People Leader for MPL Build’s first-ever AMA, alongside Jalene Vandermey-Jackson from Workleap. We talked about what traditional HR mindsets must be let go to become builders, how to collect lightweight employee feedback to help build the right products, and more.----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode284Sponsor Links:🔗 Learn more about Tilt at hellotilt.com/mpl🔗 Try AskChartHop at ChartHop.com/AI🔗 Learn more about Wellthy at wellthy.com/mplMPL Links:🔗 Go sign up for MPL Build.---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Diane Sadowski-Joseph, Co-Founder of Clarinet, joined us on The Modern People Leader. We talked about why most AI adoption stalls at “talking the talk,” how to choose the right AI use cases using the “trifecta” and the Five Frictions framework, and how “click cutters” can unlock compounding gains by removing cognitive and workflow friction.----  Here’s everything Diane referenced: https://modernpeopleleader.kit.com/fivefrictionsSponsor Links:🔗 Learn more about Wellthy at wellthy.com/mpl🔗 Learn more about Tilt at hellotilt.com/mpl🔗 Try AskChartHop at ChartHop.com/AIMPL Links:🔗 Go sign up for MPL Build.---- (07:08) Diane’s career story and path to founding Clarinet(14:43) Why AI shows up in every episode and the “why companies are stuck” question(15:58) Why AI adoption feels hard despite tool abundance (DIY, bandwidth, readiness)(21:46) The “trifecta” criteria for identifying a good use case(27:39) An example of a bad AI use case: what broke and why it was abandoned(36:25) The “Five Frictions” framework and where to start(42:50) Example 1: time-to-hire goal and candidate feedback GPT workflow(47:03) Example 2: exec reporting and “hyper-personalized” dashboard pushes(52:39) “Click cutters” and how to find them---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Liz Bronson, VP of People at Skimmer, joined us on The Modern People Leader to talk about intentionally “flatlining” her career for a period of time to prioritize parenting. ----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode282Sponsor Links:🔗 Learn more about Tilt at hellotilt.com/mpl🔗 Learn more about Wellthy at wellthy.com/mpl🔗 Try AskChartHop at ChartHop.com/AIMPL Links:🔗 Go sign up for MPL Build.---- (08:30) From teaching to HR: early roles, mentor, and learning the business(10:54) VMware era: growth, recruiting focus, and family move to Austin(11:55) Consulting chapter: building “Liz Bronson Consulting” and supporting startups(13:18) COVID shift: reevaluating priorities and deciding “it’s my turn”(15:12) Landing at Skimmer: growth, doubling, and why it is working(20:53) Intentional career “flatlining” for parenting and how she made it work(24:52) The “do it all” myth: stress, trade-offs, and household coping strategies(30:57) The career trade-offs no one talks about(32:14) Negotiating the partnership reset with her husband and what changed post-2020(41:49) The “must-have list” and choosing roles that fit life stages(45:08) The job-search grind after a reset, protecting mental health, and rebuilding momentum(48:27) Building a caregiver-friendly workplace, parental leave returns, and flexibility in practice(51:13) Influencing leaders, the business case, and the “why” behind policies and RTO mandates(55:36) Career advice for HR leaders, understanding the business, and becoming a stronger partner---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Isabel Naidoo, Chief People Officer at Wise, joined us on The Modern People Leader to share how Wise builds a cohesive employee experience across global offices while still honoring local identity. ----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode281Sponsor Links:🔗 Try Viva’s $950 one-month trial at execviva.com/mpl🔗 Try AskChartHop at ChartHop.com/AI🔗 Learn more about Wellthy at wellthy.com/mplMPL Links:🔗 Go sign up for MPL Build.---- (05:23) Isabel’s Career Story and Path to Wise(10:54) Shift to Culture and the Global Playbook Topic(11:58) Why Wise Needs a Global Footprint: Customer Proximity and Regulation(13:27) Designing a Seamless Employee Experience Across Locations(14:27) Global Consistency vs Local Identity in Workplace Design(16:38) How Wise Creates an Irresistible Office Experience(19:22) Measuring Culture vs Driving Business Outcomes(21:47) Product Operating Model and Avoiding “HR Theatre”(23:05) Rituals That Maintain Mission Focus During Growth(24:31) Company Calls, Demos, and Ownership Through Equity(25:26) Quarterly Planning Rituals and Open Participation(27:38) Observable Signals of Culture and Employee Pride(28:25) AI and How It Changes Talent Strategy at Wise(28:58) Three Focus Areas: AI Usage, Building AI Skills, and Leading AI Teams(32:32) Measuring AI Impact Beyond Usage and Where to Start(35:22) Prerequisites for AI: Data and Operating Model(37:05) Choosing Use Cases, Human-in-the-Loop, and Reinforcing Human Skills(39:33) In-Person Connection and What Sets Strong Cultures Apart(40:34) Value of Community Learning in AI and HR Networks(43:22) Collaboration Model, Flexible Work, and Benefits That Support Performance(45:43) Sabbaticals and Work-From-Anywhere Policies(47:24) AI Use Case Example: Feedback Coach and Scaling Support(48:48) Innovation at Wise: Hiring for Excellence and Practicing Feedback---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Chase Warrington, Head of Operations at Doist, joined us on The Modern People Leader to break down how async-first work enables faster decision-making, stronger culture, and scalable operations. We talked about building trust without offices, the systems and rituals behind Doist’s execution velocity, and why async workflows are foundational to effective AI adoption.----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode280Sponsor Links:🔗 Try AskChartHop at ChartHop.com/AI🔗 Learn more about Tilt at hellotilt.com/mpl🔗 Go deeper on Viva's AI Journey in Roundtable with Jani (only 10 seats)MPL Links:🔗 Go sign up for MPL Build.---- (07:30) Chase’s Origin Story(11:15) What Doist Does: Productivity Tools, Todoist, and Async-First Principles(14:45) Why Async Work Changes How Leaders Think, Decide, and Scale(17:28) Independent Decision-Making as a Non-Negotiable at Doist(20:44) The Doist Operating System: Squads, Quarterly Cycles, and Decision Frameworks(23:17) Rituals That Power Execution: Async Standups, Demos, Retros, and Dashboards(26:30) Communication as Infrastructure: Async Guidelines, Transparency, and Trust(30:45) How Async Enables Better AI Adoption and an Organizational “Brain”(33:44) Inside Doist’s AI Ops Squad: Redesigning Planning, Search, and Workflows with AI(38:17) Vibe Coding, Non-Engineers, and the Rise of AI-Enabled Builders(47:22) Partnering with Head of People Nadia Vatalidis and Scaling People Systems(53:30) The Biggest Misconception About Remote and Async Culture---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Jani Sanguino joined us on The Modern People Leader to share how Viva built an award-winning, manager-led AI transformation. We talked about the three AI competencies they prioritized, their 13-week manager-led learning path, and the most impactful use cases for their business.----  Go deeper on Viva's AI Journey in Roundtable with Jani (only 10 seats): execviva.com/mplDownloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode279----Sponsor Links:🔗 Learn more about Wellthy at wellthy.com/mpl🔗 Try AskChartHop at ChartHop.com/AI🔗 Learn more about Tilt at hellotilt.com/mplMPL Links:🔗 Go sign up for MPL Build.---- (06:03) Jani’s Path Into People Ops(09:28) What Music Taught Her About Org Design(12:55) Why Viva Went All-In on AI(13:46) Winning the Zapier Award(17:32) Viva’s AI Adoption Strategy(19:31) 3 AI Competencies: Prompting, Automation, Business Acumen(22:09) The 13-Week Manager-Led Learning Path(23:35) Picking Use Cases and Measuring ROI(26:46) Handling Resistance and Fear(30:16) Explorer to Builder to Multiplier(32:42) Viva Ambassador Program and Content GPTs(37:29) People Ops Slack Bots: Fixie and Aura(40:04) TA Dashboard Using Lovable(41:45) EAs Helping Clients Adopt AI(43:14) What They’d Change Next Time(45:18) AI Debt and Automation Pitfalls---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

We recapped MPL Live Austin with attendees Cindy Lopez (Senior Director, People & Culture, Pattern Bioscience) and Marlene Arroyo (Founder, Peoplecraft).----  Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode278Sponsor Links:🔗 Try Viva’s $950 one-month trial at execviva.com/mpl🔗 Learn more about Nava Benefits🔗 Check out AirMasonMPL Links:🔗 Go sign up for MPL Build.---- (09:04) Cindy background, why she attended, and what felt different about the event experience(10:57) Marlene background, why she returned, and what she valued from 2024 to 2025(16:14) Cindy’s take on Innovation Hall (missed Day 1, but feedback from others and Day 2 vendor conversations)(18:05) Marlene’s take on Innovation Hall: vendor conversations shifting from “AI can” to workflow integration(19:11) Bingo gamification: origin, how it worked, and what it enabled(21:11) Programming integration: how Day 1 was structured alongside the Innovation Hall(22:53) Day 1 highlights(25:49) Day 2 highlights(34:36) Key learnings from the week---- 📬 Subscribe to our weekly newsletter to get episode recaps💡 Follow The Modern People Leader on LinkedIn😊 Follow Daniel Huerta on LinkedIn😊 Follow Stephen Huerta on LinkedIn---- Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.