Flexible Work Arrangements: The Good, the Bad, and the Ugly
When Phil and I first started Henderson Properties in 1998, we were living examples of what’s become known as flexible work arrangements.
With two young boys at home, our 1,700-square-foot house quickly became both an office and a playground. We managed our growing business from our kitchen table, with our children always close by. I took business calls with a toddler on my hip and mapped out routes to show rental properties with two kids in the backseat. I learned that success in both family and business means adapting on the fly.
As the business grew, so did the need for more structure. I realized that the same adaptability that allowed us to get off the ground could also empower our team. That’s why we implemented flexible work hours and an optional work-from-home day on Fridays.
Our goal was to give our employees the freedom to manage their work in a way that suited their personal lives. When people feel in control of their time, I know firsthand that they’re more motivated, productive, and happier at work.
But with flexibility comes responsibility.
I’ve seen how blurred boundaries can lead to missed deadlines—and how some employees, despite having flexible schedules, still struggle to find satisfaction. Flexibility must be balanced with clear expectations and accountability. At Henderson Properties, we’ve learned to build trust within our team while ensuring that our flexible work policies support—not hinder—our goals.
If you’re considering implementing more flexible work arrangements at your workplace, I’m here to tell you that it has its upsides and downsides. Here’s the “good, bad, and ugly” of what you can expect.
The Good: Empowering Employees Through Choice
One of the biggest advantages of flexible work arrangements is employee empowerment.
We’ve seen how flexibility around schedules and work environments improves morale and productivity. They’re more likely to take ownership of their work and feel a stronger connection to their roles. Autonomy boosts job satisfaction and builds a culture of trust and accountability.
Our approaches aren’t the only ones you could consider. I’ve heard of other companies who have rolled out compressed workweeks to give employees longer weekends to spend with their families. You could also consider flexible start and end times so employees can end their day in time to pick up the kids from school. Depending on the type of business you run, you can offer more work-from-home days than we do—all the way up to fully remote options.
Listening to and balancing your team’s needs with your company’s daily needs and long-term goals will drive better results.
The Bad: Inconsistencies and Challenges
We quickly found that not all employees thrive with the freedom to manage their schedules.
Take our optional work-from-home Fridays, for example. As much as we wanted to trust our team to stay productive, we couldn’t help but notice that by the time Friday rolled around, the work output often took a dip. It’s one thing to offer flexibility but another to get the work done on time and up to our standards.
And let’s be honest—no matter how accommodating you try to be, some people just aren’t happy. Even with a flexible schedule, we’ve heard complaints about the lack of structure or difficulty balancing work with personal life. Be clear that a flexible work arrangement is a benefit your company has granted that can be taken away if it’s not working out as we had hoped.
One thing to note: We don’t allow work-from-home for people on a performance improvement plan. We need them in the office so we can give them the attention and feedback they need to meet the plan’s requirements.
Flexible work arrangements are not a one-size-fits-all solution. Just as my family had to juggle the demands of a growing business, you and your employees will need to adapt as you go along.
Flexible work was a tremendous leap of faith for us. Let’s be honest—does an employee give it their all while working from home? Maybe not, but if morale is boosted and deadlines are met, it should all balance out.
The Ugly: When Flexibility Leads to Friction
While flexibility can boost morale and productivity, it can also lead to serious issues. We’ve learned the hard way that without clear boundaries, flexibility can sometimes create more problems than it solves. Here’s what we’ve encountered:
Blurring of boundaries. When employees have the freedom to set their own schedules, it’s easy for the lines to get crossed. Instead of working a focused eight-hour day, some might find themselves working late into the evening, leading to burnout. Employees who can’t “switch off” feel they’re always on the clock.
Abuse of the system. While most of our team members thrive with flexible arrangements, others let responsibility slide. Some might slack off, assuming their flexible schedule means fewer expectations. This can breed resentment among those on the team who are pulling their weight.
Communication breakdowns. When employees work different hours, important messages can be more easily missed. We’ve had mistakes and delays that could have been avoided if everyone had been on the same page.
While flexible work arrangements offer many benefits, they also require careful management and clear policies. Without them, the very flexibility meant to empower employees can end up creating friction within the team.
If you decide to go this route, it’s crucial to set clear expectations, establish boundaries, and make sure everyone understands the importance of maintaining the same high standards, regardless of where or when they’re working.