--- title: Three Lessons from Five Years of Flexible Work description: Breaking news and analysis from time.com. Politics, world news, photos, video, tech reviews, health, science, and entertainment news. canonical: https://time.com/partner-content/charter/7270372/three-lessons-from-five-years-of-flexible-work/ author: Michelle Peng article:opinion: false article:content_tier: free article:published_time: 2025-03-25T10:30:50.000Z article:modified_time: 2026-04-28T07:07:30.476Z article:section: Charter og:title: Three Lessons from Five Years of Flexible Work og:description: Breaking news and analysis from time.com. 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They are at time.com/newsletters and are separate from a paid subscription.  by [Michelle Peng](https://time.com/author/michelle-peng/) Mar 25, 2025 10:30 AM UTC  Illustration by Charter · Photo by iStock Nattakorn Maneerat, monkeybusinessimages  by [Michelle Peng](https://time.com/author/michelle-peng/) Mar 25, 2025 10:30 AM UTC With high-profile return-to-office (RTO) pushes in both the private sector and federal government, some leaders critical of hybrid and remote work are again pushing the narrative that flexibility creates a trade-off between employee wellbeing and organizational productivity. “It's a funny narrative that productivity and wellbeing are at loggerheads,” says [Ellen Kossek](https://business.purdue.edu/directory/bio.php?username=ekossek), a professor emerita of management at Purdue Business who has studied flexible work and telework for over two decades. Her [early research on remote work](https://apps.it.purdue.edu/sites/Home/DirectoryApi/Files/dc90821c-0fb6-4752-83b4-4b3711c24696/Download) found that access to remote work was also associated with both higher performance and improved work-life balance, trust, and retention. (These findings have been confirmed [again](https://www.nature.com/articles/s41586-024-07500-2) and [again](https://www.dropbox.com/scl/fi/8vyd36kp5g2bnuuop9sbr/WFH%5FFenizia%5FKirchmaier%5F2025Jan.pdf?rlkey=l48f34pkvus4ouvqn8545n940&e=3&dl=0) in recent years.) Five years after the Covid pandemic shuttered offices, one in four paid US workdays were work from home (WFH) days in February 2025—a figure that has remained relatively unchanged since the beginning of last year, according to the latest [Survey of Working Attitudes and Arrangements](https://wfhresearch.com/wp-content/uploads/2025/03/WFHResearch%5Fupdates%5FMarch2025.pdf). Over the past few years, leaders across industries have designed and improved flexible-work policies that promote both productivity and wellbeing, from desk-based tech workers to [frontline retail and warehouse workers](https://sloanreview.mit.edu/article/how-to-get-real-about-measuring-to-outcomes/). Sign up for Charter's newsletter to get the handbook for the future of work delivered to your inbox. Email Address You can unsubscribe at any time. By signing up you are agreeing to our [Terms of Service](https://www.charterworks.com/terms-of-service/) and [Privacy Policy](https://www.charterworks.com/privacy-policy/). Based on our analysis of those experiences, here are some of the practices we think are worth trying: **Prepare managers to support hybrid teams with toolkits and templates.** For AFLAC chief strategy officer [Matthew Owenby](https://www.linkedin.com/in/matthewowenby/), the success of the insurance company’s flexible-work policies—and high engagement numbers across both hybrid and remote teams—comes down to giving managers the tools they need to support their teams. For example, managers are coached to help workers prevent burnout by scheduling breaks and offline hours that keep remote workdays from spilling over into around-the-clock work. AFLAC also offers templates and practices to engage remote workers on mixed teams. When facilitating a hybrid meeting, leaders are encouraged to first greet and call on remote attendees, a practice that makes it easier for them to chime in later on. “We encourage our leaders to… talk to your people that are remote every day,” says Owenby. He shares their three-part template for regular one-on-one check-ins, which includes recognition, going over any recent wins for the employee or their team; disclosure, or sharing anything that has happened that either party needs to know about; and objectives and metrics, which covers how ongoing projects are progressing and whether employees need any support. He notes that the structure allows managers and their employees to develop a regular cadence of communication, minimizing employee anxiety around reaching out to their boss and ensuring that everyone stays aligned on projects and expectations. It also helps first-time managers get up to speed and practice supporting, recognizing, and motivating employees. **Dive deeper:** Read our [FAQ](https://www.charterworks.com/hybrid-work-faqs-managers/) on how to set managers up for hybrid success, including our advice on including managers in enforcing attendance policies, developing hybrid leadership skills among managers, and reducing proximity bias. **Be intentional about connection and collaboration through offsites.** One of our favorite ways to jumpstart connection and collaboration on distributed teams is by scheduling regular in-person offsites. [Research shows](https://sloanreview.mit.edu/article/hybrid-work-how-leaders-build-in-person-moments-that-matter/) that connections between colleagues at offsites remain strengthened for three to five months. To make planning offsites easier for its virtual-first workforce, Dropbox created an Offsite Planning Team (OPT), an internal group that helps teams plan in-person gatherings. In 2024, OPT planned over 90 offsites. The company estimates that this assistance reduced the time team leaders spent planning offsites by 2,500 hours. Dropbox also rolled out a self-service toolkit called “Offsite In A Box.” “It includes instructions, timelines, location recommendations, and a wealth of rich programmatic activities and ideas that planners can choose based on their offsite’s goals,” says [Allison Vendt](https://www.linkedin.com/in/allisonvendt/), Dropbox’s global head of virtual first. The toolkit includes icebreaker ideas, team-bonding activities, agenda-building tools, facilitation guides, and follow-up instructions. Purdue’s Kossek points out that these opportunities for in-person collaboration and connection are especially important for new and early-career employees, recommending that employers schedule offsites to align with the employee life cycle. For example, time onboarding to coincide with a quarterly offsite, giving new employees a chance to jumpstart relationships. Or, a new hire might start with more days in office with team members in the first few weeks of the job before gradually phasing to more remote workdays. When it comes to building your own offsite-planning toolkit, Vendt recommends tapping into existing expertise in your organization, including learning and development, real estate, travel, event planning, and strategy teams. The goal is to design resources to be as flexible and customizable as possible to meet the unique needs of different teams. At the same time, templates and activities should be rooted in the organization’s overall business and culture goals. **Dive deeper:** Read our [guide](https://www.charterworks.com/three-steps-for-planning-your-next-offsite/) to planning your next offsite, including our [worksheet](https://www.charterworks.com/worksheet-events-goals/) on planning programming that helps your team accomplish shared goals. **Offer flexibility within your hybrid-work plan with work from anywhere (WFA) days.** Unlike other big names in financial services that have drawn up hardline RTO policies, Prudential has doubled down on hybrid work. In 2024, it launched a pilot “Work From Anywhere (WFA)” program that allows workers to work entirely remotely from anywhere in the US for four weeks per year. “The goal was to make sure that we were creating a flexible work environment where people can bring their best selves to work,” says [Nya Patel](https://www.linkedin.com/in/nya-patel-2712451/), VP of culture and inclusion at Prudential. “In that, we are creating employees that are going to be more engaged, and with that we are going to have better productivity.” It’s a benefit that workers have used to spend more time with family, travel, and even spend time with coworker friends. As the pilot enters its next phase, Patel says the company’s focus is on getting more employees to take full advantage of their flexible-work benefits, surveying employees to find potential areas of improvement, and adding structure to make it easier to request WFA time. In particular, she’s focused on managers, who set the tone for the rest of their teams. Employees are “not going to use these benefits if they don't see their manager using these benefits,” she explains. **Dive deeper:** Beyond location flexibility, build in schedule flexibility to accommodate time differences, focus time, and family obligations like school pick up. Read our [advice](https://www.charterworks.com/worksheet-team-level-agreement-key-questions/) for writing [team-level agreements](https://www.charterworks.com/template-team-level-agreement/) to get your team aligned on core coordination hours, meeting-free time, co-located working hours, and remote and hybrid collaboration practices. --- ## Read more from Charter [READ MORE](https://time.com/partner-content/charter/) [Open article: How Mastering Hybrid Is an AI Advantage](https://time.com/partner-content/charter/7334714/how-mastering-hybrid-is-an-ai-advantage/)  ### How Mastering Hybrid Is an AI Advantage [READ MORE](https://time.com/partner-content/charter/7334714/how-mastering-hybrid-is-an-ai-advantage/) [Open article: New Findings About Getting Hybrid Right](https://time.com/partner-content/charter/7332119/new-findings-about-getting-hybrid-right/)  ### New Findings About Getting Hybrid Right [READ MORE](https://time.com/partner-content/charter/7332119/new-findings-about-getting-hybrid-right/) [Open article: The workplace divide that's reshaping American business](https://time.com/partner-content/charter/7312868/the-workplace-divide-thats-reshaping-american-business/)  ### The workplace divide that's reshaping American business [READ MORE](https://time.com/partner-content/charter/7312868/the-workplace-divide-thats-reshaping-american-business/) --- ```json [{"@context":"https://schema.org","@type":"NewsArticle","@id":"https://time.com/partner-content/charter/7270372/three-lessons-from-five-years-of-flexible-work/","mainEntityOfPage":{"@type":"WebPage","@id":"https://time.com/partner-content/charter/7270372/three-lessons-from-five-years-of-flexible-work/"},"headline":"Three Lessons from Five Years of Flexible Work","datePublished":"2025-03-25T10:30:50.000Z","dateModified":"2026-04-28T07:07:30.476Z","description":"What we’ve learned about designing policies that promote wellbeing and productivity, with examples from Prudential, AFLAC, and Dropbox.","url":"https://time.com/partner-content/charter/7270372/three-lessons-from-five-years-of-flexible-work/","keywords":[],"thumbnailUrl":"https://static.time.com/v3/assets/bltea6093859af6183b/bltc8ce177aba1a453b/6998c50fa97fc065bda742fa/charter-flexible-work.jpg?branch=production&width=1200&quality=75&auto=webp&crop=1200:675&height=675","author":[{"@type":"Person","name":"Michelle Peng","jobTitle":"","url":"https://time.com/author/michelle-peng/"}],"articleSection":"Charter","image":[{"@type":"ImageObject","url":"https://static.time.com/v3/assets/bltea6093859af6183b/bltc8ce177aba1a453b/6998c50fa97fc065bda742fa/charter-flexible-work.jpg?branch=production&width=1200&quality=75&auto=webp&crop=1200:675&height=675","width":1200,"height":675,"headline":"charter-flexible-work","caption":"","creditText":"","representativeOfPage":true}],"publisher":{"@type":"Organization","name":"Time","url":"https://time.com/","logo":{"@type":"ImageObject","url":"https://time.com/images/logo.png","width":528,"height":156},"foundingDate":"March 3, 1923","sameAs":["https://www.facebook.com/time","https://www.instagram.com/time/?hl=en","https://twitter.com/time","https://www.pinterest.com/timemagazine"]}},{"@context":"https://schema.org","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"https://time.com/partner-content/charter/7270372/three-lessons-from-five-years-of-flexible-work/","name":"Three Lessons from Five Years of Flexible Work"}}]}] ```