What makes it difficult to crack working remotely

My previous article hit you with a bunch of ways to make remote work a success as a superstar developer and manager. But let’s be real—remote work isn’t all sunshine and rainbows. Things can go sideways quickly 💩, and when you throw people into the mix who aren’t exactly remote-work savvy, it can turn into a full-blown disaster, demotivating the entire team.

In this article, I'll break down some of the common challenges remote work can bring—and share a few tips on how you can tackle them without losing your sanity.

TL;DR

Remote work sounds like a dream, but it’s not without its pitfalls. In this article, we’ll explore the common challenges that come with managing and working in remote teams, from communication breakdowns to maintaining productivity. You’ll learn how to tackle these obstacles by adopting the right mindset, fostering strong team values, and using practical strategies like mentorship and pair programming. Whether you're a seasoned remote worker or just starting out, these tips will help you navigate the complexities of remote work without losing your sanity—or your team’s motivation.

Maturity

Maturity isn’t necessarily about age; it’s more about professional, personal, and emotional growth. Sounds lofty, but really, it’s just the ability to handle responsibilities, work independently, and communicate effectively—speak up rather than bottle it all up. It’s not just about getting the job done; it’s about getting it done well and on time.

Simply put: adulting. It’s that mythical state we’re all supposed to have mastered by now. Spoiler alert—it’s hard.

Some developers struggle with remote work because they need more guidance and supervision. This is especially true for junior developers still learning the ropes—or for any developer who's new to the company. Then there are those getting up to speed with your tech stack, custom-crafted patterns, and codebase quirks. They may need some extra hand-holding, even if they don’t ask for it.

Managing time effectively or communicating needs clearly? For some, it’s like herding cats. And when people—myself included—are hit with too much information all at once, their brains just tap out. Like a computer that’s been running too long and desperately needs a reboot.

This can lead to misunderstandings, missed deadlines, and subpar work. And let’s not forget the tension and conflict that builds up when people feel lost, unsure if they’re working on the right thing, or isolated because they miss the usual banter with colleagues.

Pair Programming

While pair programming can’t solve every problem, it’s one of the best ways I’ve found to tackle this issue. Pair up less experienced developers with more seasoned team members. Pair programming—where two developers work together on the same code—can be a fantastic way to mentor and level up junior developers. It does require a few things to work well: solid internet connectivity, availability (time zone challenges can get tricky), emotional intelligence, and, of course, patience on both sides.

To get the most out of these sessions, structure them to include code reviews, discussions on design decisions, explanations of best practices, and actually coding together. That way, both developers can build confidence and learn from each other while getting real work done.

Mentorship

Another helpful approach is assigning a mentor to these developers. A mentor can provide guidance, answer questions, and offer valuable feedback on their work. Having that extra layer of support can help them feel more connected to the team and give them the confidence they need to grow.

Training

You can also provide training and resources to help them sharpen their skills. This could be online courses, workshops, books, or even in-house sessions like brown-bag lunches, lean-coffee meetups, or ad-hoc knowledge-sharing discussions. Encourage them to take ownership of their learning journey and actively seek out opportunities to grow.

Team Cohesion

Since it’s easy for people to feel disconnected without regular in-person interactions, you and your team should prioritize fostering team cohesion. Building team cohesion in a remote setting can be tricky, but it’s not impossible.

One effective approach is organizing virtual coffee breaks or happy hours where the team can relax and chat about things unrelated to work. These informal sessions give everyone a chance to connect on a personal level, breaking down some of the isolation that can come with remote work.

Another option is hosting online games or trivia competitions—whether it’s something light like Skribbl.io (watch out for that domain name) or a more engaging game like Jackbox, these activities allow for some friendly competition and plenty of laughs. The key is to create spaces where people can interact casually, just as they would in a traditional office environment.

You can also get a bit more creative with activities that encourage personal sharing or collaboration. Setting up a virtual “show and tell” session, for instance, lets team members showcase their hobbies, cool gadgets, or even something they’ve learned recently. It’s a simple way to get to know each other better and opens up conversations that go beyond project updates.

Similarly, organizing team wellness challenges or collaborative playlists helps strengthen the feeling of being part of a community, even when everyone’s working miles apart. These small but meaningful activities build rapport and remind your team that, despite the distance, they’re still part of a supportive and connected group.

Communication

I’ve seen firsthand how hard it can be for people to speak up. Frustratingly so, as if there's an invisible barrier of fear, uncertainty, and doubt swirling like a cyclone, sucker-punching them in the gut, stopping them from reaching out. But here’s the thing: the consequences of not speaking up are often far worse.

Being shy or introverted doesn’t help either. I’ve learned that if you want to grow and improve, you have to punch your comfort zone in the face.

Communication is essential—it’s the glue that holds remote teams together. Without it, things can unravel fast: misunderstandings pop up, deadlines get missed, and relationships take a hit. Time zones, cultural differences, and language barriers only make it worse. That’s why being clear, concise, and considerate in your communication is key.

Use tools like Slack, Microsoft Teams, Zoom, and email to stay connected. Schedule regular check-ins, stand-ups, or one-on-ones to keep the lines of communication open. And be proactive—reach out to your colleagues and ask for help when you need it.

Values

Without a strong set of values, you're like a ship without a rudder. You drift aimlessly, tossed by the waves, never reaching your destination. In a remote team, where face-to-face interactions are limited, having a clear sense of direction becomes even more crucial.

This calls for a solid set of values: honesty, integrity, and respect, for example. You need to be honest about your capabilities and limitations, uphold integrity in your work, and show respect for your colleagues and deadlines. These values help build trust, foster collaboration, and create a positive work environment.

Adopting and buying into company and team values is crucial for the success of any organization, especially in a remote setting. When everyone aligns with the same core principles, it creates a shared sense of purpose, fosters trust, and strengthens collaboration. It’s not just about doing the work, but about doing it in a way that reflects the integrity and goals of the team. Values act as a guide for decision-making and help maintain consistency in behavior, communication, and accountability. Without this buy-in, teams can quickly become fragmented, with misaligned priorities and diminished morale. Embracing these values ensures that everyone moves in the same direction, building a positive, productive, and cohesive work environment.

Mindset

It helps to think and act like a founder. This means taking full ownership of your work, being proactive, and embracing a growth mindset. When you think like a founder, you don’t just do the minimum to get by—you treat the company’s success as your own. This mindset pushes you to go beyond what’s expected, find solutions instead of waiting for instructions, and continuously seek out ways to improve both your skills and the work you're delivering.

A growth mindset is key here. It’s about being open to feedback, learning from mistakes rather than dwelling on them, and constantly looking for opportunities to develop. Challenges become chances to grow, and setbacks are seen as part of the learning process. Adaptability is essential, too—especially in fast-paced environments where things can change quickly. Being able to pivot, adjust your approach, and stay flexible helps you thrive in the long run. In short, thinking like a founder empowers you to not only contribute more but to find personal growth and satisfaction in the process.

It’s easy to get sidetracked when working remotely, so having the discipline to stay focused and productive is crucial. This involves creating a routine, setting boundaries, and holding yourself accountable for your work. By taking ownership of your time and tasks, you can maintain a high level of productivity and deliver quality results.

Leadership

In a remote setting, leadership also requires building trust and autonomy. Without the physical presence of a manager, team members need to feel empowered to make decisions and take ownership of their work. This means setting clear expectations and giving your team the space to achieve goals in their own way while being available for support when needed. Remote leaders must foster a culture of transparency, where team members feel safe sharing their progress, challenges, and ideas. Regular check-ins, one-on-one meetings, and an open-door virtual policy are key to maintaining a connection with your team. Ultimately, effective remote leadership is about balancing guidance with trust, empowering individuals while ensuring everyone stays aligned with the broader vision of the company.

Other Challenges

Let’s face it, working from home makes it easy to blur the lines between work and personal life. Setting boundaries, creating a dedicated workspace, and sticking to a routine can help you maintain a healthy balance.

Remote work can lead to isolation and stress. Regular check-ins, virtual social activities, and mental health resources can help combat these challenges and foster a supportive work environment. Take regular breaks, practice self-care, and reach out for help when needed.

Tools and technology can be a double-edged sword. While they enable remote work, they can also be a source of distraction and overwhelm. Finding the right balance and using these tools effectively can help you stay organized and focused. Don’t cowboy and try every tool under the sun—stick to what works best for you and your team and ensure there is buy-in from everyone.

Conclusion

Remote work is a double-edged sword—it offers flexibility and autonomy but also comes with its fair share of challenges. Whether it's navigating communication barriers, staying productive, or fostering team cohesion, the key to success lies in embracing the right mindset, building strong values, and maintaining open lines of communication. By taking ownership of your work, investing in your team’s growth, and fostering a positive, transparent culture, you can turn those challenges into opportunities for growth. So, punch that comfort zone in the face, stay proactive, and remember—remote work might not be all sunshine and rainbows, but with the right approach, it can still be pretty awesome.

Resources

The hero image and its corresponding thumbnail were generated by DALL-E, an AI model developed by OpenAI via ChatGPT itself.

I'm basing this article on my experience with remote work. I've been working remotely since 2018 and have enjoyed its benefits and experienced the drawbacks thereof. I’ve also referenced the DK Essential Managers guide titled “Managing People”. Check it out.

Thanks

Thank you for taking the time to read this! I'd love to hear your thoughts—is remote work something your team is equipped for and what challenges does your team face? Please share your insights in the comments below.