Common Challenges of Flexible Working and How to Address Them Proactively
Published: 12/05/2025
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In this article, we are going to investigate common challenges of flexible working and what steps you can take to tackle them before they become an issue. We will also briefly touch on the structural and setup questions.
Flexible working has become the norm in today’s workplace, but it still presents challenges for both early adopters and those trying to make the switch today. Curiously, those are not unique stand-alone challenges either, but rather common roadblocks many companies run into. The solutions for them exist, but aren’t being discussed often enough, leaving businesses to poke and prod until they find a way. To save you time, however, we are willing to summarise the said common challenges in one article and propose some solutions.
It’s important to point out that the ways we are talking about aren’t necessarily the only correct options. There are multiple ways to address the challenges we’ll be discussing, and ultimately, your approach should be in line with your goals, values and circumstances. However, these are the solutions that worked for us and our clients, hence we’re confident to share them.
The biggest challenge of flexible working is creating a suitable environment. It includes aspects such as ensuring a shared work environment for remote and in-person teams, setting the hours during which flexitime is available, and several more. There is an easy way to put these, at first sight, different challenges under the umbrella of one solution.
You can accommodate flexible work by employing digital tools that easily connect teams and let you adjust the way your business runs. They let you adjust the limitations, the requirements and other aspects you need to create a structured and efficient workplace. Additionally, such tools will help you address other common issues we will discuss next.
How come challenges that are seen as common lack documented solutions? Simply put, because they are seen as ‘common’, people refrain from talking about them or asking questions, not to make themselves look unprofessional. But we aren’t ashamed to talk, let alone educate others.
Let’s address the elephant in the room. While the most commonly spoken about concern regarding flexible working is the communication gap and difficulties connecting scattered teams, there’s a bigger challenge: ensuring security and compliance. A heavier focus on digital aspects and an extended use of online solutions typically exposes companies to more threats, especially if the workers aren’t trained on cybersecurity. From falling to phishing and accidentally compromising the company’s data, to more serious infringements like GDPR violations, flexible working often increases security risks. The most straightforward solution would be to put your teams through security and compliance-oriented training, but such courses can be costly, time-consuming and, ultimately, ineffective. There is, however, another method that is easier and less dependent on your workers’ vigilance. Namely, it’s putting measures that work as a security net.
Most digital solutions of today come equipped with layers of protection to preserve your data, keep track of your business staying compliant and many more. With additional setup, you can put in blockers to automatically activate when a user is exposed to potential harm, or to send a notification to the IT team if a threat of compromise is spotted. It’s still a good idea to train your teams on security and compliance, regardless - there is no such thing as too much protection. Especially when dealing with sensitive matters such as client data.
Moving to a more lighthearted topic, another common issue observed in mixed offices is the death of company culture. When interacting with your colleagues in person every day, bonds and values, both of which are the foundation of the culture, are actively cultivated. However, when half of the office is working remotely and people only see each other once or twice a week, if ever, the office culture as we know it becomes impossible.
The first step to rectifying this is accepting that, alongside the working model, the concept of company culture changed. This means the traditional means, such as weekly company drinks or lunches, are no longer relevant. Instead, establish new consistent rituals that let your teams stay together and expect to block out time for bonding. For example, a weekly recurring team call where everyone catches up for 20 or so minutes. More long-term, think about regular in-person events, such as group activities, outings, etc.
If left unaddressed, challenges stop being bumps in the road and instead turn into serious setbacks. It’s best to begin tackling them from the get-go, proactively seeking solutions before they become unnecessary. There are a few tools and strategies you can quickly add to your business and optimise as you go.
Flexible working, despite being widespread and the ruling work model these days, still induces paranoia in some companies, especially when it comes to gauging productivity. To put your mind at ease, it’s recommended that you invest in a time tracking solution. Alongside providing receipts of where your team’s time goes, it brings on heaps of additional benefits. For example, it’s a great tool to ensure you bill your clients correctly and on time. Or, it can give you insightful reports within minutes, which can become the cornerstone of your strategy moving forward.
The best part is that while offering ample benefits, time tracking solutions are very affordable. For instance, at Timesheet Portal, we offer a pay model in which the clients pick and choose what features they require and pay for them exclusively. This makes our solution suitable for companies of any size, as well as those that are only starting out. Both upgrading and downgrading are accessible from within the platform itself, requiring no involvement of the sales team. In other words, you have full control of what you’re paying.
Ensuring there are several communication outlets runs deeper than simply connecting your teams. Naturally, when your workers can’t talk face-to-face, it’s a must to create an environment in which they can keep the conversation going, but not all communication has to be direct to be efficient. A setup consisting of several integrated solutions can build a centralised platform that supports seamless collaborations, thorough visibility and the erasure of departamental siloes. In other words, it gives your teams an ultimate hub that’s designed to keep them connected.
What your setup entails will largely depend on what your team needs to support their day-to-day operations and the level of communication that needs to be maintained. Some of the standard additions are a shared document drive, a holiday calendar, a shift scheduler and the premises to leave comments on the progress/deliverables of others. Naturally, this list will expand based on the different solutions you add. The ultimate goal is ot build a setup that works for you.
Flexible working either makes or breaks work-life balance, depending on your team’s mentality. Given that your employees’ well-being should be one of your key priorities, it’s important you eliminate the possibility of things going the wrong way before they get a chance to. Thankfully, there are ways to do that with little to no effort using designated tools.
We’ve spoken about it in another article, but for flexible working to be efficient, there needs to be a structure. If your company is only adapting to full-time hybrid working instead of treating it as a temporary solution, or if you’ve only started working with mixed teams, finding the optimal setup may be time-consuming. But there’s a solution to help you speed the process up.
Smart scheduling isn’t going to take away all your worries in relation to rotating your teams’ physical presence on site, but it’s a technology that learns and adjusts to your processes the more it’s included in them. For starters, when you first get a scheduling solution, simply feed into it the information on how often your workers need to show up in person. The first few automated schedules will most likely need adjusting, but such tools are made to be trained based on trends, which means the accuracy will increase as you go. If the tool supports employees swapping shifts with one another, such data will be recorded and used too. Not only is smart scheduling convenient when finding the optimal balance, but it also helps your team adjust their workflows based on each other’s availability, which is visible to everyone in a centralised hub, further supporting team collaboration efforts.
The biggest and most common challenge of flexible working is the least spoken about, despite its ability to get your business in serious trouble—security and compliance. The best way to address it is through a combination of solutions that prevent threats and training your staff to be cybersecurity literate. Another, less incriminating one is maintaining company culture. The first step is to acknowledge that it is going to take a different shape from the one you’re used to. Then, it’s finding both recurring and rarer ways to engage to nurture it.
The best way to tackle these challenges before they begin affecting your progress is by bringing digital solutions on board as soon as you can. Time tracking and scheduling tools can help you find the perfect spot in terms of how much flexibility you can give your teams to enhance their productivity instead of stunting it. Adding more solutions and ensuring they all integrate will also help you build a centralised platform for your teams to communicate and collaborate, nurturing better rapport and alignment as they go. A healthy balance between structure and flexibility is what will elevate your business to a new level.
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