The 3 Challenges Of Flex Work Structures (And How To Solve Them)

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Flexibility at work brings productivity, camaraderie, and a host of other benefits. 

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But that doesn’t mean challenges don’t occur.

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To understand what challenges organizations face, Willo interviewed and surveyed over 100 HR and talent leaders around the world, from organizations ranging from 100 to 20,000 employees. 

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The leaders we spoke with said challenges typically fell into one of three categories: Productivity, Cultural, and Financial. 

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This blog is an intro to our findings; read the Embracing Flexibility report for all the data.

1. Productivity And Output

The key to productivity is understanding flexibility inside of workplace constraints, with the goal being to minimize constraints where possible. 

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Case Study: Teams Over Multiple Time Zones

Fintech company Synctera expects that employees will be online from approximately 9 am to 5 pm in their local timezone. 

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With four time zones to manage across the US and Canada, the majority of the team will be online together around noon to 3 pm Eastern time (9 am to noon Pacific; 1 pm to 4 pm Atlantic).

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Attending team meetings is an expectation—west coast employees don’t get to ditch morning meetings in the name of flexibility.

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To combat the risk of meeting creep, the company also blocks every Friday from approximately 3-6 pm eastern time. This, said Zoe, is a time for everyone to wrap up the week strong so they can enjoy the weekend.

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“Flexibility is saying, ‘As long as you’re showing up to meetings and you're getting your work done—that's fine,’” explained Zoe Schafer, Director of People, Synctera. “You can log off at 4:30 pm and no one is going to say ‘You owe us 30 more minutes.’ There’s no punching a clock.”

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Productivity is also informed by collective feeling. An individual employee may have the tools they need, but if they perceive unfair treatment compared to colleagues, they may not be as productive. 

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A key example of this is companies where employees must be on-site given the nature of their work, such as manufacturing or transportation. 

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Case Study: Blending Fairness With Work Needs

The majority of HelloFresh’s approximately 20,000 employees work on-site in distribution centers or in transportation.

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While many other colleagues can work remotely, there’s an element of fairness at play.

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First, the company decided to follow regional norms for each market. These expectations are clearly communicated to candidates on job descriptions.

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Second, managers apply a level of human flexibility to all on-premise jobs.

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“From a management perspective, we give employees freedom [within cultural norms],” said

Thomas Klein, Global Head of International Talent Acquisition at HelloFresh. “In Germany, we will say a time you have to work, but you can come earlier or a bit later. If you start a bit later in the morning, then you leave a bit later. We have core working hours in Germany.”

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2. Culture And Connection

Flexible work arrangements can improve or detract from culture; the key is in implementation. 

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For example, if a company operationalizes existing ad-hoc flexible arrangements, employees are likely to feel more respected and trusted—boosting culture as a result. 

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But there is also a risk of teams that are like ships passing in the night; you’re aware of one another but don’t build connections.

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“We weren't feeling a big productivity loss [when we switched from hybrid to remote-first]. What we were seeing was a connection loss.” — Michelle Brooks, Chief People & Culture Officer, Security Compass

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Promoting a healthy culture will always be organization-dependent; there is no one-size-fits-all. However, there are common threads. 

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Case Study: No Brilliant Jerks 

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Job van der Voort, CEO at Remote, believes the key to connection is everyone feeling like they can reach out to one another. 

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If you have a brilliant jerk problem in your company, people will begin to feel uncomfortable—that is what Job feels is the true breakdown of connection and culture, not being in different physical spaces. 

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“The most important thing we can do is create a really safe workspace,” Job said.

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3. Financial 

Flexibility can both remove and add costs, so the key is balancing that with overall budgets. 

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Case Study: IRL Get Togethers

The Human Resources Professionals Association (HRPA) has regular retreats for executive planning, team building, and more. However, Jodi Kovitz, the CEO of the HRPA, was clear that it’s not just about physically being in the same space. If you’re spending money, there has to be a better reason.

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“You have to give folks a real, meaningful reason to come together—whether it's a cross-functional strategic planning, a retreat, or intentional relationship building,” said Jodi.

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How To Overcome The Challenges Of Workplace Flexibility

The key to overcoming the challenges of flexible work arrangement lies in implementation. 

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Here’s what (and how) top organizations design for success:

• Performance management
• Ways of work
• Technology
• Employee set up

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To learn all the details and read even more case studies of companies implementing flexible work arrangements, read the entire Embracing Flexibility report. 

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Read the Embracing Flexibility Report now

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