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From Friction to Feedback: Leaders on Turning Policy Pushback into Progress

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From Friction to Feedback: Leaders on Turning Policy Pushback into Progress

In the evolving landscape of work, where flexibility once felt like a hard-won victory, certain HR policies continue to stir quiet (and sometimes loud) resistance from employees. 

Why do rules that seem logical on paper—return-to-office mandates, rigid performance reviews, mandatory tech adoption—often land like unwelcome intrusions? 

On HRSpotlight, candid executives, CEOs, HR advisors, and culture builders open up about the single policy that reliably generates the strongest pushback in their organizations, and the thoughtful, human-centered ways they’ve turned friction into alignment. 

From return-to-office mandates met with pleas for autonomy, to annual reviews that feel disconnected from daily reality, to AI tool rollouts that threaten professional identity—these leaders reveal how resistance rarely stems from laziness or entitlement. 

Instead, it signals a deeper need for trust, voice, and purpose. 

Their shared strategies—transparent “why” conversations, employee co-creation, flexible compromises, continuous feedback models, empathy-led transitions—demonstrate that the most resisted policies can become the most embraced when handled with clarity, inclusion, and genuine care. 

Explore which approaches are quietly reshaping compliance into commitment.

Read on!

Najeeb Khan
Head of Training & Events, Teamland

At Teamland, where we collaborate with HR leaders to improve engagement and team performance, one of the policies employees often push back against is the annual performance review process.

Many employees find it outdated or anxiety-inducing, especially when feedback feels one-sided or disconnected from their daily work.

The resistance usually reflects a deeper desire for ongoing feedback and recognition, not opposition to accountability.

We recommend addressing this by shifting to continuous feedback models supported by regular team check-ins and coaching sessions.

This approach helps HR foster transparency, strengthen trust, and turn performance reviews into growth conversations rather than evaluations.

Continuous Feedback Ends Annual Review Dread

Rebecca Trotsky
Chief People Officer, HR Acuity

Policies that try to control where or how people work are the ones employees push back on the most.

But there’s nuance here: Our people aren’t resisting work; they’re resisting a loss of trust and autonomy.

The way to address that resistance is to give teams agency. Let them define their own moments that matter for collaboration, strategy and connection, whether virtual or in person. Back it up with clear intent and make the experience meaningful.

When presence is purposeful, not mandated, employees feel trusted and engaged.

The future of work isn’t hybrid or remote—it’s human.

When we design work around trust and autonomy, people don’t just show up, they show up with purpose.

Agency Over Control Sparks True Engagement

Marcus Denning
Senior Lawyer, MK Law

As the CEO of MK Law I have experienced both the legal aspects of managing an organization as well as the human element of managing a diverse group of professional staff members.

Combining my experience of Commercial Leadership and my knowledge of Criminal Law provides me with a unique understanding of how to handle employee complaints and develop successful methods for removing obstacles that are present at the workplace.

One of the primary reasons that employees resist implementing many HR policies is due to the strictness of the annual performance evaluation process.

Employees typically believe that they are separate from their daily job and therefore will be frustrated by the evaluations.

There is a disconnect between the type of feedback employees receive during their annual evaluation and the employees’ work over the course of the entire year within the traditional model.

Continuous feedback is the best method to reduce or eliminate the resistance to implementing a new HR policy such as a shift to a continuous feedback model.

Managers must continuously communicate with employees regarding their performance and recognize employees for their accomplishments on an ongoing basis.

This continuous communication results in an employee who is more engaged, motivated and productive in their role.

Ongoing Feedback Replaces Stressful Yearly Reviews

David Weisselberger
Entrepreneur, Erase The Case

A common area of resistance among the workplace policies developed by Human Resource departments has been the long-standing, rigid performance evaluation process.

Due to the fact that these reviews are traditionally conducted annually, employees view them as being separate from their daily work responsibilities, which can lead to frustration and a disengaged workforce.

In response to this, I suggest moving away from the traditional performance evaluation model and toward a continuous feedback model.

Under this model, instead of waiting until formal performance review times, managers will provide employees with continuous, timely feedback based on each employee’s performance.

Early recognition of accomplishments and identification of opportunities for growth and development creates an environment where employees feel comfortable communicating openly about their job, while also allowing employees to make proactive changes to their work assignments as needed.

Timely Feedback Stops Annual Review Pushback

Nathan Wadding
CEO, Kindling Culture Agency

One HR policy employees often push back against is mandatory technology adoption—especially around AI tools.

While these policies are intended to increase efficiency, they can feel threatening to people whose expertise and identity are tied to their work. The resistance isn’t really about technology; it’s about purpose, pride, and security.

To address this, leaders need to focus on how the change happens, not just the outcome.

Start by defining what AI means to your organization and connect it clearly to your mission. Identify early adopters to model success, provide extra support for those less comfortable, and create forums for open conversation.

Most importantly, honor the experience people bring.

If you respect their value and invite them to help shape the transition, they’ll be far more likely to embrace it.

Honor Expertise to Ease AI Adoption

Hassan Elbiali
Owner, Agendapedia

One HR policy that consistently encounters pushback is mandatory return-to-office requirements after extended remote work periods.

Many employees value the flexibility and autonomy of remote work; sudden shifts can feel restrictive or dismissive of individual needs.
To address this resistance, HR leaders should prioritize transparent communication—clearly outlining the business rationale and listening to employee concerns.

Incorporating flexible hybrid options, gathering regular feedback, and actively involving staff in policy discussions builds trust and fosters buy-in.

By demonstrating empathy and a willingness to adapt, companies can ease the transition and maintain morale.

Empathy + Options Soften Return-to-Office Pushback

James Bernard
Principal Owner, Alcatraz Escape Games

I run haunted attractions and escape rooms in Utah, so I’ve dealt with plenty of team resistance–especially around our actor training requirements and safety protocols.

The biggest pushback I’ve seen is against time restrictions during team activities.

When we introduced the 5-minute rule at Alcatraz Escape Games (if your team is stuck for 5+ minutes without progress, you must ask for a hint), corporate groups initially hated it. They saw it as admitting defeat. But when I showed them completion data–teams using hints strategically had an 87% escape rate vs. 34% for teams who refused help–the resistance melted away.

People want to win more than they want to be stubborn.

My approach is to frame policies around success metrics, not compliance.

Instead of “you have to ask for hints,” I positioned it as “here’s how winning teams manage their 60 minutes.”

At Castle of Chaos, when we mandated that actors complete improv training, I didn’t sell it as a requirement–I showed them footage of guest reactions when actors adapted in real-time versus following scripts. Suddenly everyone wanted that training.

The key is making the policy feel like a competitive advantage for them, not a restriction on them. Show the scoreboard, not the rulebook.

Show the Scoreboard, Not the Rulebook

Gerald Michaels
Owner, Adept Construction

I’ve been running a family roofing company in the Chicago suburbs since 1997, so I’ve seen my share of policy battles with crews.

The one that gets the most pushback? Mandatory pre-job site photos and documentation. When we required every team to spend 15 minutes before starting work photographing existing conditions–not just the roof, but landscaping, driveways, AC units–the complaints were instant. Guys saw it as wasted time when they could be setting up ladders.

I fixed it by showing them the insurance claim we avoided in Downers Grove.

A homeowner tried to say we cracked their driveway during a tear-off, but our pre-job photos proved that crack existed before we arrived.

That single documentation saved us a $3,200 repair bill and kept our insurance rates from spiking. I told the crew: “You’re not taking pictures for me–you’re protecting yourself from getting blamed for damage you didn’t cause.”

The real shift happened when one of our longtime foremen had a customer claim we damaged their gutter during a Villa Park job. He pulled up his time-stamped photos showing the gutter was already dented, and the complaint died immediately. Now the same guys who fought the policy are the ones who take the most thorough photos–they realize it’s 15 minutes of protection against weeks of headaches and disputes that could tank their reputation.

Fifteen Minutes of Photos Beats Weeks of Headaches

The HR Spotlight team thanks these industry leaders for offering their expertise and experience and sharing these insights.

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In Conversation With Nicholas Wyman

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In Conversation With

Nicholas Wyman

Author

Attract, Retail & Develop: Shaping a Skilled Workforce for the Future

Hi Nicholas, thank you for joining us! Before we dive into “Attract, Retain & Develop”, please tell us about yourself and your current role.

Nicholas Wyman:

Thank you, it’s great to be here.

I’m Nicholas Wyman, a workforce practitioner and CEO of the Institute for Workplace Skills & Innovation America, where I focus on building skills-based career pathways that connect people to meaningful employment.

My work sits at the intersection of business, education, and public policy, helping employers solve talent shortages while creating opportunities for individuals. Over the past two decades, I’ve worked with employers across industries, and both private companies and government agencies, to rethink how they attract, develop, and retain talent.

What drives me is the belief that talent is universal, but opportunity is not. Employers have a powerful role to play in closing that gap.

What’s the origin story for your latest book, Attract Retain & Develop: Shaping a Skilled Workforce for the Future? How did it evolve from an idea to a tangible title? Tell us more about this journey.

 

Nicholas Wyman:

The idea for my latest book came directly from the frustrations I was hearing from employers everywhere. They were struggling to find talent, yet often overlooking capable people because of outdated hiring practices.

I realized there wasn’t a practical playbook that combined real-world workforce strategies with leadership and culture in a way that business leaders could immediately apply.

The book evolved over several years as I gathered case studies, tested ideas through our programs, and refined what actually works in practice.

My goal was to create something actionable rather than that leaders could use to build resilient, future-ready teams.

Your book argues that traditional hiring models are outdated. What specifically is broken in the way most organizations recruit today, and what mindset shift do HR leaders need to make first to truly “disrupt” their approach?

 

Nicholas Wyman:

The biggest problem is that many organizations hire based on traditional proxies for talent, like degrees, credentials, and job titles, instead of actual capability.

This approach unintentionally filters out incredible candidates who have the skills but not the traditional ‘pedigree’. It also slows hiring and contributes to persistent talent shortages.

The mindset shift is moving from credential-based hiring to skills-based hiring, asking, “What can this person do, and how can they grow?” rather than “Where did they go to school?”

Once leaders make that shift, they open the door to a much broader, more capable talent pool.

Your own career path, from chef to global workforce practitioner, is unconventional. How did that experience shape your philosophy on talent, and what can employers learn from non-linear career journeys when evaluating candidates?

 

Nicholas Wyman:

Starting my career as a chef taught me things that you can’t learn from a text book: soft skills like time management, communication and team-building, and critical thinking. Kitchens are performance-based environments, you either deliver or you don’t, and that shaped how I view talent.

My transition into workforce development reinforced that many of the most capable people willing to take initiative and problem-solve come from non-traditional backgrounds. Employers who overlook non-linear career paths miss out on adaptable, resilient, and highly motivated individuals.

Today’s workforce is far more dynamic, and hiring practices need to reflect that reality.

Through your work with the Institute for Workplace Skills & Innovation America, you’ve helped create thousands of skills-based career pathways, including apprenticeships for people with disabilities. What lessons from those programs can HR leaders apply to build more inclusive and effective talent pipelines?

 

Nicholas Wyman:

One of the biggest lessons is that inclusive hiring isn’t charity, it’s actually smart business with a proven ROI for both individual businesses and for the economy, and our society, at large.

When employers focus on skills and provide structured pathways like apprenticeships, they uncover talent that was previously overlooked. We’ve seen firsthand that with the right support and mentorship, individuals thrive and become highly loyal, high-performing employees.

Another key lesson is that partnerships matter. It’s key to work with community organizations and training providers, as that reduces the burden on employers. Inclusion expands your talent pool and strengthens your organization at the same time.

Many employers are concerned about automation and AI reshaping jobs. Based on your research and workforce experience, what skills should organizations be prioritizing now to future-proof both their workforce and their business?

 

Nicholas Wyman:

AI is transforming work, but the real challenge that comes with utilizing this technology is ensuring trust, good judgment, and human capability. The risk isn’t just that AI will replace tasks, but that people may over-rely on it without critical thinking.

That means the most important skills are human skills: adaptability, communication, ethical judgment, and problem-solving. Technical literacy is important, but the ability to question, interpret, and apply technology responsibly is what creates value.

Organizations that invest in these durable human skills will be far better positioned to navigate whatever comes next.

As an author, what are 3 other books you’d recommend to our audience? Why?

Nicholas Wyman:

As someone who works at the intersection of workforce strategy, business performance, and human capability, I tend to look beyond mainstream HR titles. Talent systems rarely fail because of policy. They fail because of behavior, stress, culture, and leadership blind spots.

Three books that have shaped my thinking:

Atomic Habits by James Clear

Clear’s central argument is simple: outcomes are driven by systems, not willpower. That applies directly to organizations. Engagement, productivity, and inclusion are the result of repeated behaviors reinforced over time. If leaders want change, they must design better systems and reward the right daily actions. Culture is not a slogan. It is an institutionalized habit.

The Mindbody Prescription by John Sarno

This book explores how chronic stress manifests physically. In organizations, that same stress shows up as burnout, disengagement, and turnover. Too many workplaces wear chronic pressure as a badge of honor. It is not. It is a performance tax. Sustainable output requires healthier environments and leaders who understand the cost of hidden strain.

The Gifts of Imperfection by Brené Brown

Brown’s work on vulnerability and courage is ultimately about trust. And trust drives performance. Innovation, accountability, and retention depend on psychological safety. High standards and empathy are not opposites. The best organizations combine both. When people feel safe to speak up and grow, performance follows.

For me, workforce strategy is not just about hiring models or talent pipelines. It is about energy, resilience, and behavior at scale. Organizations that understand that outperform those that treat talent as a transactional process.

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Author of Attract, Retain & Develop, Nicholas “Nick” Wyman began his career as an award-winning chef. Transitioning from the culinary arts to the business world, Nick leveraged his leadership experience to become a globally recognized workforce practitioner. As the CEO of the Institute for Workplace Skills and Innovation Group (IWSI), he redefines career pathways, transforming how the modern world views skills and success. Under his leadership, IWSI has ignited over twenty thousand skill-based career paths. Nick is the author of two books and contributes to Forbes, Fast Company, the MIT Press Journal, and CNBC.

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Women’s History Month Series – In Conversation with Stephanie Davis Neill

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HR Spotlight Interview

Stephanie Davis Neill

Women's History Month Interview Series

In Conversation with Stephanie Davis Neill

Our special guest today is Stephanie Davis Neill, Chief Operating Officer at Click Boarding. With over 25 years of leadership experience spanning agile startups to Fortune-ranked companies, Stephanie brings a uniquely structural perspective to HR technology. A lifelong operator and Georgia Tech graduate with deep expertise in Lean/Six Sigma methodologies, she proves that the most effective way to solve complex people problems—such as employee engagement and workload reduction—is through robust, repeatable processes.

In this episode, Stephanie shares her playbook for protecting her peace through structural clarity, explains why she describes the 2026 workforce as “cautious,” and offers critical advice on how to strategically pivot after surviving the “Glass Cliff.”

Thank you for joining us, Stephanie! We’ve heard it said that ‘Nobody plans to go into HR; they are usually dragged into it because they are good at listening.’ Is that true for you? What was the specific moment you realized, ‘Oh, I’m actually meant to do this’?

Stephanie Davis Neill:

As a lifelong operator, I still find myself surprised when I describe my role in HR Technology.  I wasn’t initially sure it was the right fit until I thought about the challenges we solve, like engagement, accelerating readiness to work, and workload reduction for support teams and I thought, “this is what I have been doing my whole career!”. It’s true, when you really do pay attention, you can often clearly see the way forward.

You’ve worked in everything from furniture retail to global logistics. What have you learned about transformation?

Stephanie Davis Neill:

The fundamentals of managing transformation remain remarkably consistent from a startup to the Fortune 100: it is always about people and process. Whether you are hiring seasonal labor or highly specialized skill sets, transformation isn’t about the industry; it’s about facilitating how people and tools come together to deliver something amazing.

If you could describe the current ‘mood’ of the workforce in 2026 using just one word, what would it be? Why?

Stephanie Davis Neill:

Cautious.

As the pace of change continues to accelerate, particularly with macro economic pressures, adoption of AI, and shifts in company remote work policies, many employees remain uncertain about what comes next.  I suspect this is directly impacting the motivation for risk taking and job mobility.

We often talk about the ‘Glass Ceiling,’ but lately, the conversation has shifted to the ‘Glass Cliff’, where women are promoted to leadership only during times of crisis. Have you ever felt that pressure to be the ‘fixer’ in a broken system?

Stephanie Davis Neill:

Shining during a time of crisis can be a great way to get noticed and to accelerate leadership opportunities. I challenge women who rise during these periods to pivot quickly when the crisis is over to demonstrate strategic leadership. It can be very easy to fall into the trap of being the go-to person in every crisis. I once had responsibility for literal crisis management (weather and other disaster response functions) and because it ran so smoothly, it stayed with my team for several years instead of appropriately moving to the risk management team. After that, I learned to not only fight for what I wanted to manage, but also for passing along what I shouldn’t.

HR professionals are the ‘first responders’ of the corporate world, handling grief, layoffs, and conflict. What is your specific protocol for protecting your own peace after a day of absorbing everyone else’s stress?

Stephanie Davis Neill:

My protocol involves creating repeatable systems and routines that “anchor” the work. I rely on fixed organizational process, like our bi-weekly product and client discussions, to ensure everyone is on the same page and working toward the same priorities. This structural clarity helps prevent the “chaos” of absorbing everyone else’s stress because we have a clear, shared path forward.

HR is often described as a thankless job—you’re the villain when things go wrong and invisible when things go right. Why do you stay? What is the specific moment that reminds you ‘This is why I do this’?

Stephanie Davis Neill:

I stay because I love helping facilitate how people, tools, and resources come together to deliver something amazing. The “why” becomes very clear when you see the personal connection our teams make with clients. We recently finished a large implementation where the client didn’t want to let their consultant go and even asked for his personal information just to send a thank-you note. Hearing that our team has made that kind of impact, even at the very beginning of a partnership, is incredibly exciting.

“Transformation isn’t about the industry; it’s about facilitating how people and tools come together to deliver something amazing.”

That operational philosophy from Stephanie Davis Neill is a powerful reminder that at the core of every successful business transformation, the fundamentals of people and process remain entirely constant.

A huge thank you to Stephanie for sharing her expertise and proving that the best HR strategies are built on solid operational foundations.

As COO, Stephanie Davis Neill leads efforts to retain and grow Click Boarding’s customer base while optimizing operations for scalable growth. With over 25 years of experience in operations across startups, private-equity-backed firms, and Fortune-ranked companies, she is a proven change leader, most recently serving as VP of Customer Success & Direct Sales at Aaron’s. Passionate about building efficient processes, she applies Lean/Six Sigma methodologies to drive strategic problem-solving and cross-functional collaboration. Her expertise spans B2B account management, customer experience, and service management. A Georgia Tech graduate, Stephanie enjoys traveling and volunteering when not at home in Marietta, Georgia, with her family and rescue dog, Peanut.

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Women’s History Month Series – In Conversation with Advita Patel

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HR Spotlight Interview

Advita Patel

Women's History Month Interview Series

In Conversation with Advita Patel

Joining us is Advita Patel, an award-winning business communications consultant, professional confidence expert, and the 2025 President of the Chartered Institute of Public Relations. As the founder of CommsRebel and co-founder of A Leader Like Me, Advita specializes in building inclusive, high-performing environments. She is also the host of the Decoding Confidence podcast, with her highly anticipated book of the same name launching in May 2026.

In this interview, Advita breaks down the exhaustion of the modern workforce, the amplified pressures of the “Glass Cliff” for women of color, and why true empathy in leadership requires active practice, not just assumption. From setting non-negotiable boundaries to challenging the dangerous reliance on “gut feeling” in hiring, Advita provides a masterclass in leading with clarity and intention.

Thank you for joining us, Advita! If you could describe the current ‘mood’ of the workforce in 2026 using just one word, what would it be? Why?

Advita Patel:

Tired. The last six years have felt relentless for many people: constant change, new technology, economic uncertainty, and very little space to breathe or reflect. That’s why taking charge of the things we can control and prioritising our wellbeing matters more than ever. When you’re running on empty, you simply can’t show up properly for anyone else.

We often talk about the ‘Glass Ceiling,’ but lately, the conversation has shifted to the ‘Glass Cliff’, where women are promoted to leadership only during times of crisis. Have you ever felt that pressure to be the ‘fixer’ in a broken system?

Advita Patel:

Absolutely, and not just as a woman but also as a woman of colour, that pressure is amplified. There’s this unspoken expectation that you have to constantly prove yourself, outperform, and somehow fix what others couldn’t. You’re pitted against each other, and you genuinely believe you need to give twice as much just to be seen as half as capable. What makes it worse is that when you can’t fix a broken system, you internalise it as personal failure. It’s no wonder so many women burn out.

HR professionals are the ‘first responders’ of the corporate world, handling grief, layoffs, and conflict. What is your specific protocol for protecting your own peace after a day of absorbing everyone else’s stress?

Advita Patel:

Strong boundaries, and I don’t negotiate on them. My laptop stays in my office, and I don’t check anything work-related after 6pm. I know how tempting it is, especially when there’s an on-going issue. But if you don’t model your own boundaries, you can’t expect others to respect them either. Burning yourself out helps no one, and the long-term cost of not protecting yourself can be devastating.

Without naming names, tell us about a time you had to deliver tough news (a termination, a restructuring) that actually taught you something profound about leadership or empathy.

Advita Patel:

I was once asked to send out a restructure email just before a Bank Holiday weekend. The thinking was that it would get ahead of the rumours without leadership having to field questions straight away. I pushed back. Dropping news like that with no context, right before people disconnect for a long weekend, is unfair and causes unnecessary anxiety. The response from senior leadership? “Everyone’s an adult, they’ll understand.” That moment crystallised something important for me: empathy isn’t instinctive for everyone. It has to be actively practised, not assumed.

Have you ever felt pressure to soften your delivery or ‘be nice’ in a way that male counterparts aren’t? How do you balance empathy with the need to be firm on policy?

Advita Patel:

Yes. I was told my tone came across as aloof and cold, which genuinely surprised me because warmth is a big part of who I am. But I noticed the feedback only surfaced when I challenged or disagreed with something, and that told me a lot. Real empathy isn’t about backing down or over-softening to avoid discomfort. It’s about recognising that people aren’t difficult, they’re just different. It means understanding someone’s perspective without needing to agree with it, and holding your position without becoming defensive. Giving people space to be heard is empathy. Disappearing into agreeableness is not.

The age-old tension is between ‘People’ and ‘Profits.’ Can you share a specific example where you had to fight for a budget or a benefit that didn’t have an immediate ROI, but you knew was critical for the culture?

Advita Patel:

How to fight for a budget without a clear ROI? That’s practically a book I could write. In the work I do, it’s rarely possible to show an immediate return because it forms part of a much bigger picture. So, alongside attaching metrics to spend, I always talk about the consequences of not doing something, not just what success looks like if we do. That reframe gives budget holders the full picture rather than just our version of it.

We talk a lot about ‘gut feeling’ in hiring. How are you using data to challenge your own biases, or the biases of hiring managers, when it comes to promoting women and underrepresented talent?

Advita Patel:

Gut feeling is based on your lived experiences. And if your lived experiences have been sheltered and you haven’t had much interaction with people who are different from you, the bias you show in your gut will be aligned to your version of what good looks like. That’s why so many teams and boards have similar faces. This, in many cases, isn’t intentional. People will generally believe they have hired the best. But what they may not realise is that they are measuring best to their personal criteria. And if someone who is different or looks different is being interviewed, the natural reaction is that they are not a good fit. This is why data and evidence are needed to help slow your thinking down and help you tap into your reflective side of the brain.

If you could ban one corporate buzzword forever, what would it be?

Advita Patel:

Leverage. We don’t use that word at home, in conversation, in real life. I genuinely have no idea why it became so embedded in workplace language.

“Giving people space to be heard is empathy. Disappearing into agreeableness is not.”

That powerful distinction from Advita Patel fundamentally challenges how women are often conditioned to operate in corporate spaces. Her insights remind us that true leadership isn’t about fixing fundamentally broken systems at the expense of our own well-being; it is about establishing non-negotiable boundaries and using data to dismantle the biases hidden within our “gut feelings.”

A huge thank you to Advita for her candor and for giving us practical tools to protect our peace while driving meaningful organizational change.

Advita Patel is an award winning business communications consultant and professional confidence expert. She is the founder of CommsRebel, a consultancy supporting organisations to build inclusive, high performing workplace cultures, and the co-founder of A Leader Like Me, an international agency focused on inclusive leadership and employee experience. Advita is the host of the Decoding Confidence podcast, which explores confidence at work through honest conversation and practical insight. Her forthcoming book, Decoding Confidence, will be published in May 2026. An international speaker and award winning podcaster, Advita regularly speaks on confidence, leadership, inclusion, and communications. In 2025, she was the President of the Chartered Institute of Public Relations in 2025.

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Employee Leave Isn’t the Problem. The Real Issue Is Lack of Planning.

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March 09, 2026

Employee Leave Isn’t the Problem. The Real Issue Is Lack of Planning.

By Rachel Shaw

Leave management is one of the most frustrating and most predictable parts of human resources.

And that is exactly the problem.

Employers often feel caught off guard when an employee needs time away from work for a medical condition, family care or a personal matter. The process becomes emotional, reactive and operationally disruptive. But the reality is this: over the course of any employee’s tenure, leave is not an exception. It is an inevitability.

Every workforce will experience illness, injury, pregnancy, caregiving needs, mental health events and life transitions. These are not outliers. They are part of the employee lifecycle. Yet many organizations still treat leave as a one-off rather than building systems that anticipate it.

The issue is not that employees need leave. The issue is that too many organizations are not designed to handle it well when it comes up.

  • Leave Management Is a Systems Issue

Most employers have compliance mechanisms in place. They know how to issue an FMLA notice or respond to a doctor’s note. But compliance alone is not a strategy.

Where organizations struggle is in the absence of a clear, coordinated leave management program that addresses:

  • how leave is requested and tracked
  • how coverage is handled operationally
  • how supervisors respond in the moment
  • how leave interacts with ADA obligations and workplace accommodations
  • how employees are supported during and after the leave period

Without this infrastructure, every leave request becomes a disruption instead of a manageable workflow.

Proactive employers recognize that leave is a predictable operational reality and build programming around it.

  • Planning Reduces Stress for Everyone

When employers take the time to define their leave processes in advance, the experience changes dramatically.

Supervisors are no longer guessing what to do or reacting emotionally in the moment. HR is not reinventing the wheel with every request. Employees are not left feeling guilty, unsupported, or confused about their rights and responsibilities.

Clear programming allows organizations to respond consistently and with confidence. That includes:

  • clear expectations for how and when employees request leave
  • defined processes for job coverage and workload redistribution
  • structured communication points during leave
  • thoughtful return to work practices that support reintegration

This is not about eliminating the operational impact of leave. It is about managing it intentionally.

  • Flexibility Where It Works

One of the most effective ways to reduce the strain of leave is through thoughtful flexibility.

In some environments, that may mean remote work or modified schedules. In others, particularly in the public sector, healthcare or frontline environments, it may mean shift swapping, modified assignments, or creative scheduling.

Not every role can be done from home. But every organization can evaluate where flexibility is possible.

When employees can adjust schedules for medical appointments or caregiving needs without immediately moving into formal leave status, organizations often see reduced absenteeism and improved morale.

Flexibility, when structured well, becomes a pressure valve that supports both operations and employees.

  • Supervisor Frustration and the Culture of Leave

One of the most significant risks in leave management is not legal. It is cultural.

Supervisors often carry the operational burden when someone is out. That burden can lead to frustration, especially when leaves are extended, intermittent or complex.

Left unaddressed, that frustration can show up in subtle but damaging ways such as tone, comments, skepticism  or disengagement. Employees quickly pick up on this and it erodes trust.

At the same time, employers are right to be attentive to potential misuse. That is part of good program management.

The solution is not to ignore concerns or to assume the worst. It is to train supervisors to operate with professional judgment, to follow process, avoid assumptions, document appropriately, and escalate concerns through the proper HR channels rather than reacting emotionally.

Employees should not feel like they are doing something wrong when they use a benefit or protection they are legally entitled to.

The way supervisors respond in these moments defines the organization’s culture far more than any written policy.

  • ADA and the Continuation of the Conversation

Another common breakdown point is what happens when statutory leave ends.

When FMLA or state leave entitlements are exhausted, the conversation is not necessarily over. Employers may have additional obligations under the Americans with Disabilities Act to evaluate whether additional leave or other workplace accommodations are reasonable.

Too often, organizations treat the end of FMLA as the end of the process.

In reality, it is often the beginning of a different conversation, one that requires individualized assessment, interactive dialogue and thoughtful decision-making.

Organizations that build a coordinated ADA and leave management program, which I often refer to as programming the interactive process, are far better positioned to navigate these transitions consistently and defensibly.

  • Supporting Employees, Not Just Complying with the Law

At its core, leave management is not just a compliance function. It is a human one.

Employees request leave at some of the most difficult moments in their lives: a cancer diagnosis, a complicated pregnancy, a parent in decline, a mental health crisis or recovery from injury.

How an organization responds in these moments matters.

Employers that approach leave with clarity, structure and empathy see measurable benefits: higher engagement, stronger retention and increased trust in leadership.

Those that operate in crisis mode often see the opposite: burnout, resentment and turnover.

  • Mental Health and the Evolving Workforce

Mental health-related leave requests continue to rise across industries.

Employees are more willing to seek support, but they are still highly sensitive to how those requests are received. Stigma has not disappeared. It has just become quieter.

Supervisors need guidance on recognizing potential leave triggers, responding without prying into protected medical information and connecting employees with HR and available resources.

Organizations that treat mental health with the same seriousness and neutrality as physical health create a safer and more stable workplace for everyone.

  • The Cost of Not Planning

The cost of poor leave management extends beyond legal exposure.

It shows up in:

  • operational disruption
  • supervisor burnout
  • inconsistent decision making
  • employee disengagement
  • avoidable turnover

Replacing experienced employees is expensive. More importantly, it disrupts the organization’s continuity and culture.

When employees see that their colleagues are treated with fairness, respect and professionalism during leave, it reinforces their trust in the organization.

  • A Final Thought

Leave is not the problem.

The absence of planning is.

Organizations that move from reactive response to intentional design, build clear processes, train supervisors and align ADA and leave programming, are able to manage leave in a way that supports both operations and people.

That is the goal.

Not perfection. Not zero disruption.

But a workplace where employees can navigate life’s inevitable challenges without fear and where employers can respond with consistency, clarity and care.

That is what good leave management looks like.

About the Author

Rachel Shaw, founder of Rachel Shaw Inc., is a nationally recognized ADA and leave management expert and sought-after speaker known for helping organizations turn legal compliance into operational strength. With more than two decades of experience, she designs in-house systems that allow employers to manage accommodations with both legal precision and human-centered leadership. She is the creator of the ADA Interactive Process Hallway® protocol, now used by thousands of organizations to manage disability accommodation requests confidently, consistently, and with care.

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Attract Retain & Develop – Nicholas Wyman

by

ATTRACT RETAIN & DEVELOP

Shaping a Skilled Workforce for the Future

– NICHOLAS WYMAN

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New book by Workforce Specialist Nicholas Wyman offers a fresh approach to Leadership and Skills-Based Learning for the future.

Key Takeaways

Disrupt

Break free from outdated hiring models and embrace bold, game-changing workforce strategies.

Thrive

Create a high-performance culture where employees feel valued, motivated, and driven to succeed.

Evolve

Reskill, adapt, and future-proof your workforce to stay competitive in an era of rapid change.

Connect

Attract top talent and build unstoppable teams by fostering deep engagement and visionary leadership.

PRIMARY AUDIENCE

  • Business owner
  • Hiring Managers
  • HR Professionals
  • Entrepreneurs

ABOUT THE AUTHOR

NICHOLAS WYMAN

Nicholas “Nick” Wyman began his career as an award-winning chef. Transitioning from the culinary arts to the business world, Nick leveraged his leadership experience to become a globally recognized workforce practitioner.

As the CEO of the Institute for Workplace Skills and Innovation Group (IWSI), he redefines career pathways, transforming how the modern world views skills and success.

Under his leadership, IWSI has ignited over twenty thousand skill-based career paths. Nick is the author of two books and contributes to Forbes, Fast Company, the MIT Press Journal, and CNBC.

Short Thesis

In today’s volatile job market, marked by talent shortages, automation, and evolving employee expectations, workforce expert Nicholas Wyman delivers a timely guide for business leaders in Attract, Retain & Develop. Wyman offers practical, forward-thinking strategies to help organizations future-proof their workforce and build thriving workplaces. Drawing on decades of experience in workforce education and skills development, including his leadership of IWSI America, Wyman challenges outdated hiring models and presents a results-driven approach to finding, training, and retaining top talent. Through real-world case studies and expert insights, he provides a clear blueprint for sustainable workforce success.

Excerpt

Over the decades my journey has taken me from being an award-winning chef to leading the international Institute for Workplace Skills and Innovation (IWSI), where I’ve built up expertise in job skills training. Our group employs eight hundred apprentices at any given time and has successfully graduated more than 20,000 others. We have a network of more than three hundred small, medium, and large employer partners. Although I hung up my apron a few years back, I still keep in touch with my culinary roots. My philosophy today leans toward farm-to-table, focusing on organic, locally sourced ingredients, and I try to live a lifestyle that’s clean and healthy.

My goal here has been to not create yet another “formula” book on the workings of the workplace. And just to be up-front, I’m no McKinsey-style management guide. You won’t find robotic, data-driven analysis or structured methodologies here. What you will find are practical ideas, including some key ingredients such as mentoring, mastering change
in a tech-driven world, and building a resilient, innovative workforce culture. To this I have mixed in (hopefully) some entrepreneurial hustle (the same hustle that gets startups off the ground).

This book is a culmination of my diverse (some say crazy) background. From culinary to corporate, talent development to embracing change, my aim is to offer fresh insights into the workplace. Those insights often take a different track from the age-old “get into a good college” mentality. Not that I have anything against college students. It’s just that in the modern age, there are many options to consider. As a hiring manager or business owner, you need to have a keen awareness of who’s out there seeking employment and what they can offer your team. You need to know how you will captivate them and demonstrate why you want them on your team—and how you will entice them to stick around for a while.

Join me on a journey as we explore innovative strategies, redefining the future of work. The path for which I advocate is a path less traveled, but one rich with creative solutions and ideas that can lead to impactful change.

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