Executives at Crestline Services announced a new “flexible work policy” this week, describing it as a major step toward modernizing the workplace and empowering employees. Shortly after the announcement, leadership clarified that participation in the policy is mandatory and that flexibility will be applied uniformly across the organization.

The policy, outlined in an internal memo distributed Monday morning, emphasizes trust, autonomy, and adaptability while setting clear expectations regarding availability, responsiveness, and work hours. Employees are encouraged to manage their own schedules, provided those schedules align with team needs, client demands, and what the company described as “real-time operational realities.”

“This is about giving people the freedom to work how they work best,” said CEO Lauren Whitaker during a virtual staff meeting. “As long as that happens to be all the time.”

Flexibility, Defined

According to the memo, employees may choose where and when they work, so long as they remain accessible during core collaboration windows, extended collaboration windows, and “emerging collaboration needs.” The document does not define when those needs begin or end.

“Our philosophy is simple,” said Chief Human Resources Officer Michael Grant. “Flexibility doesn’t mean absence. It means readiness.”

Grant emphasized that the company is not tracking hours, but is closely monitoring outcomes, engagement levels, and responsiveness across platforms.

“If the work’s getting done, there’s no issue,” he said. “And if it’s not, we’ll know.”

Policy Rollout

The announcement followed months of internal discussion about employee burnout, retention challenges, and what leadership described as “changing expectations around work-life integration.” Surveys conducted earlier this year indicated that employees valued flexibility, though several respondents noted concerns about unclear boundaries.

Leadership described the new policy as a direct response to that feedback.

“We listened,” Whitaker said. “And we acted.”

Employees were instructed to attend a mandatory training session explaining how to make the most of their flexible schedules. The session included guidance on maintaining availability, managing notifications, and ensuring that flexibility does not interfere with productivity.

“One of the biggest risks of flexibility is misuse,” Grant said during the training. “We want to avoid that.”

Employee Experience

Initial reactions among staff were mixed. Some welcomed the formal acknowledgment that work no longer fits neatly into traditional schedules.

“It’s nice to hear them say they trust us,” said one employee, who requested anonymity. “I just don’t know when I’m allowed to not be working.”

Others expressed concern that flexibility would effectively extend the workday.

“They said we can work whenever,” another employee said. “But also that we should respond quickly. So it feels like the answer is always now.”

Several employees noted that expectations around responsiveness were emphasized more than autonomy during the rollout.

“They kept saying ‘own your time,’” one employee said. “Then they explained all the ways we should be available.”

Mandatory Autonomy

Leadership addressed concerns by reiterating that flexibility is a benefit, not an obligation, while also making clear that opting out is not an option.

“This is the direction we’re going,” Whitaker said. “It’s important that everyone’s aligned.”

When asked whether employees could request more defined schedules, Grant said such requests would be evaluated on a case-by-case basis.

“We don’t want to limit flexibility with rigid structures,” he said.

Employees said the explanation was confusing.

“If you ask for structure, you’re not flexible,” one employee said. “And if you’re not flexible, that’s a problem.”

Performance Implications

Internal guidelines indicate that managers will assess performance based on deliverables, communication, and what the document refers to as “availability alignment.” Employees are encouraged to proactively communicate their working hours, though those hours may be adjusted as needed.

“Flexibility works best when everyone is flexible,” the guidelines state.

Managers were advised to set clear expectations with their teams while remaining adaptable to changing circumstances. Training materials emphasize the importance of balancing autonomy with accountability.

“Flexibility without accountability doesn’t scale,” Grant said.

Employees noted that accountability appeared to be clearly defined, while autonomy remained abstract.

Industry Trend

Workplace analysts say Crestline’s approach reflects a broader trend among organizations attempting to reconcile flexible work with operational control.

“Companies want the benefits of flexibility without losing oversight,” said workplace consultant Dana Morales. “That creates tension.”

Morales noted that many flexible work policies rely heavily on informal norms, which can lead to inconsistent experiences across teams.

“When flexibility is mandatory, it stops being flexibility,” she said. “It becomes a new baseline.”

Crestline executives acknowledged the challenge but said the policy would evolve.

“This is a living framework,” Whitaker said. “We’ll adjust as we learn.”

Communication Expectations

One section of the memo focuses on communication, emphasizing the importance of being reachable across platforms. Employees are encouraged to regularly check email, messaging apps, and project management tools throughout the day.

“The goal is seamless collaboration,” Grant said.

Employees said the emphasis on constant connectivity undermined the promise of flexibility.

“They said we don’t have to be online all day,” one employee said. “Then they listed all the times we should be checking in.”

Several employees described feeling pressure to remain available even during personal time.

“You don’t want to be the person who misses something,” one employee said. “So you just stay on.”

Leadership Perspective

Executives maintain that the policy represents progress and that flexibility ultimately benefits employees.

“This isn’t about control,” Whitaker said. “It’s about trust.”

When asked how trust is measured, Whitaker pointed to performance outcomes and team engagement.

“If people are delivering, the system works,” she said.

Employees said delivery expectations had not changed, though the context had.

“The work is the same,” one employee said. “The hours are just… flexible.”

Looking Ahead

Crestline plans to review the policy after six months, gathering feedback from employees and managers to determine what adjustments may be necessary. Leadership said they are committed to making flexibility sustainable.

“We’re learning together,” Grant said.

Employees remain cautiously optimistic, though some expressed skepticism about how flexibility will function long-term.

“It sounds good,” one employee said. “I just don’t know when it stops.”

For now, Crestline’s flexible work policy stands as a reflection of modern workplace ambitions: promising autonomy, delivering availability, and redefining flexibility as something everyone must embrace — on demand.