The Modern People Leader: Forward-Thinking HR 245 - The Leave Experience Is a Culture Test
Jennifer Henderson (CEO, Tilt), Jessica Winder (SVP People, CoLab Software), Allison Whalen (CEO, Parentaly), and Justin Clifford (CEO, Bereave) joined us to talk about what most companies get wrong when it comes to employee leave. We discussed parental and bereavement leave through a human lens—from compliance and continuity to return-to-work strategies and performance review pitfalls.
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🔗 Go download Tilt's Modern HR Leader's Guide to Leave that Works - this is a full recap of this conversation.
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(06:26) The 3 core challenges of employee leave: compliance, continuity, and care
(09:58) What “support” actually looks like during leave, not just compliance
(16:09) Real-life examples of how broken leave policies hurt employee trust
(18:57) Bereavement leave: why 51% of people leave their jobs within a year of loss
(21:09) Building better return-to-work frameworks and communication plans
(23:56) “Did you know?” HR comms and surfacing underused employee benefits
(25:38) The manager’s role: why they’re the most powerful force during leave
(26:49) Jessica’s childcare breakdown story + creative leave support solutions
(30:22) Small, meaningful ways to show real care during a return to work
(32:02) Why policies mean nothing without psychologically safe manager behavior
(34:14) Performance reviews: how leave-related bias undermines careers
(36:16) The need for written re-onboarding plans for every returning employee
(37:42) The “10x” moment: leave as a defining employer brand experience
(40:52) Why many managers never wanted to manage people—and how that shows up
(43:44) SOPs for grief: standardizing human touch, not just tasks
(44:57) Why outsourcing leave support can actually free managers to show up better
(46:48) What not to do: excluding managers from leave conversations entirely
(48:14) The untapped business value in training middle managers
(50:04) Jessica’s fears returning from leave as a senior executive
(52:12) Why sales comp during leave is never perfect—but always worth refining
(54:45) Err on the side of employee-favorable: retention > replacement
(56:07) Every leave situation is different—so start planning 3–4 months ahead
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