Connect with Jessica on LinkedIn →
Summary
- HR leaders are expected to absorb the weight of the organization's hardest moments. Everyone knows whose desk the rock lands on.
- Key reframe: being able to carry something does not mean it is easy. HR leaders who forget this eventually break, not just bend.
- Jessica got sober in January 2020 while serving as a Director of HR and was promoted two months later. No one at work knew. That experience shaped her view of what employees carry in silence.
- Immediate takeaway: build a peer network of HR professionals outside your organization now, before you need somewhere safe to send the late-night text.
Who This Episode Is For
HR leaders, chief people officers, and HR business partners who are holding too much and want practical strategies for building resilience, training managers, and responding to employees with less policy and more humanity.
What You'll Learn in This Episode
- Why HR is one of the loneliest roles in any organization and how a peer community outside the company changes that.
- How to respond to a crisis or difficult world event at work when you do not have all the answers.
- What makes a culture book different from a handbook and why honest transparency steadies a workforce during turbulent times.
- How to structure manager training so managers stop routing every hard conversation back to HR.
- Why bereavement policies that define qualifying relationships fail employees and what to do instead.
- How to support one employee in a personal crisis without triggering the expectation that every employee gets the same response.
Key Takeaways
HR Is Not an Exempt Position
HR leaders carry the same economic anxiety, political weight, and personal loss as every employee they support. They are also expected to hold space for everyone else at the same time.
- Your ability to carry something is not proof it should only be yours to carry. EAP exists for HR too. Use it.
- The loneliness of HR is structural: you cannot discuss a colleague's crisis with anyone inside the building. That requires a deliberate solution, not willpower.
- Your colleagues do not see your burden because you have managed it invisibly. That is a skill. It is also a cost.
- "Just because I can carry it doesn't mean it's easy." Jessica D. Winder, Hidden Gem Career Coaching
Build Your Peer Community Before You Need It
The most reliable support system for HR leaders is other HR leaders outside the organization. Not colleagues who share the same conflicts of interest. Peers from other companies who can take your unfiltered question without anything being at stake.
- Start on LinkedIn, at conferences, in professional associations. Relationships that matter are built before you need them, not during a crisis.
- A peer network is where you send the real question: the employee in a domestic safety situation, the termination with legal exposure, the thing you cannot ask anyone inside the building. People who have been there will answer.
- Grief support for employees applies to HR leaders too. Name what you are carrying with people who can hold it safely.
Lead With the Person, Not the Policy
When times get hard, HR leaders default to policy. Scripts. Checklists. The handbook. In the moments that matter most, that is exactly wrong. The clearest example: a termination where the manager reads from a script while the person across the table stops hearing anything.
- Recognize that shock blocks information. Policy details delivered during a termination are not retained. Follow up in writing the next day. Do not lead with documentation.
- Ask: "Is there someone you can call right now who can support you?" Most HR leaders have never been told they are allowed to do this. They are.
- When an employee calls with news of a loss, listen first. Send the bereavement policy by email. Never lead with the handbook in a moment of grief.
- Scripts exist because someone got burned legally. Use them as a guide. Do not replace a person with one.
Acknowledge What Is Happening in the World
When something heavy happens outside the organization and employees are already watching the news on their phones, silence from leadership is its own message. Employees, especially younger workers, make job decisions based on whether a company acknowledges what matters to them.
- You do not need answers. "I don't know what you're going through, but here are the resources" signals that the company sees what is happening.
- Remind employees of what is available: EAP, mental health apps, therapy coverage. Send the list when something happens. Do not assume they remember it exists. For more on how EAP fits into a broader support strategy, the distinction matters more than most HR teams realize.
- Personal crises do not require organization-wide responses. Paying for two employees' hotel rooms during a wildfire evacuation is not a precedent that you owe every employee a hotel. It is a human response to a specific situation. The logic that individual support must be universal is a myth that keeps companies from helping anyone.
Replace the Handbook with a Culture Book
Most employee handbooks are records of everyone who did something wrong. They are legal documents, not culture documents. A culture book is honest about what it is actually like to work at the company, including the parts that do not make the careers page.
- Assess the gap between the culture you have and the culture you say you have. Build the culture book from the real version, not the aspirational one.
- Send it during the hiring process. Ask candidates if they read it. Ask whether the culture is one they want to sign up for. Transparency before someone joins is one of the most stabilizing investments HR can make.
- The culture book holds the organization accountable to what it says it is. That accountability matters more during turbulent times than any policy update.
Equip Managers Before You Need Them
Most managers are battlefield promotions. They are the last person standing and suddenly the person their team brings everything to. When an employee is grieving or in crisis, the manager is the first person they encounter at work. How that conversation goes often determines whether the employee stays.
- Run monthly cohort sessions where new managers role-play the hardest scenarios: terminations, underperformance conversations, bereavement responses. Role-play builds muscle memory that policy never will.
- Send weekly micro-learning nudges. A Slack message with one statistic or one tip keeps knowledge active between sessions without adding another meeting.
- The goal is not to route every hard conversation back to HR. It is to give managers the skill to handle the first 24 hours themselves, so employees feel supported by the person closest to them.
About Jessica D. Winder
- Chief People Officer, author, and co-founder of Hidden Gem Career Coaching, with more than 15 years of HR leadership across tech, telehealth, and B2B SaaS.
- Three-time VP or SVP of People, including Refine Labs, a remote-first marketing agency where she built the company's culture infrastructure from scratch.
- Keynote speaker on HR transformation, compensation transparency, and leading as a working parent. Her talk "The Audacity to Interview Pregnant" draws from interviewing for an SVP role while four months pregnant with her second set of twins.
- Got sober in January 2020 while serving as Director of HR. None of her colleagues knew. That experience shapes her entire framework for what employees carry in silence and why organizations should stop assuming everyone is fine.
Connect with Jessica on LinkedIn →
Frequently Asked Questions
How should HR leaders protect their own mental health when employees are constantly bringing them their problems?
Build a peer community of HR professionals outside your organization before you need it. These are people who can take a 11pm text about a real crisis without putting confidentiality at risk. EAP exists for HR too, not just the employees you manage. Take every PTO day available and set hard boundaries around when you are unreachable.
What is the biggest mistake HR leaders make when times get hard?
Retreating into policy and script instead of staying human. When the handbook becomes the first response to a person in crisis, the moment is lost and cannot be recovered. Lead with the person. Follow up with the documentation by email. In a bereavement or termination conversation, the human response in the room is the only thing that cannot be sent later.
What should HR leaders say when something difficult happens in the world and they have no answers?
Acknowledge it and say that you do not have answers. Remind employees of available resources: EAP, mental health apps, therapy coverage. Give explicit permission to step away if the event is local or affected them personally. Employees who hear nothing from leadership during a crisis often make job decisions based on that silence.
What is a culture book and how is it different from an employee handbook?
A culture book describes what it is actually like to work at a company. Most employee handbooks are legal documents built from past violations. A culture book is sent during the hiring process and tells candidates the real expectations: the hours, the work environment, the hard parts. It holds the organization accountable to the culture it says it has, which matters far more during turbulent times than a policy update.
Should a bereavement policy define which relationships qualify for leave?
Restricting bereavement leave to defined relationships fails employees because grief does not follow legal categories. Someone raised by a grandmother loses a parent-equivalent. A close friend's terminal diagnosis affects a team member's ability to work regardless of FMLA eligibility. Rethinking the immediate family definition in bereavement policy is one of the highest-impact steps HR leaders can take.
Related Episodes
