Katie Wood
Remote working challenges are something I thought I had a handle on – until the third Zoom call of the day froze mid-sentence, my dog started barking at a leaf, and I realised I hadn’t spoken to another human face-to-face in nearly 48 hours.
In theory, remote work is the dream. No commute. Total flexibility. The holy grail of work-life balance. But in reality, it’s a bit messier. We’re navigating loneliness, blurred boundaries, weird power dynamics, and a whole lot of cultural drift. And that’s just the employee side – leaders are trying to manage engagement, performance, and connection without the usual tools (like actually seeing people).
The real remote working challenges aren’t just about Wi-Fi or time zones. They’re about connection. Or rather, the lack of it. The casual chats that used to happen while waiting for the kettle to boil now require a calendar invite. Building trust takes longer. And maintaining energy and momentum when your “team” is just faces in little boxes? That’s no small feat.
But, it’s not impossible. In fact, I’ve experienced first-hand how powerful remote relationships can be – deeper, even, than some in-person ones. So in this piece, I’m unpacking the remote work hurdles that no one prepares you for, plus the less-obvious ways to navigate them. Whether you’re an employee feeling adrift or a leader trying to keep your culture alive via Slack emojis, this one’s for you.
Table of Contents
- Communicating
- Feeling Invisble
- Too Many Tools
- The Work-Life Blur
- Culture Drift
- Lack of Recognition
- Solving Remote Working Challenges
The Challenges of Remote Working
Communicating ≠ Connecting
One of the biggest remote working challenges I’ve faced – and seen in almost every team I’ve worked with – is this sneaky little illusion: because we’re communicating, we must be connecting. Spoiler: we’re often not.
We’re sending messages, sitting on back-to-back Zooms, throwing around emojis like digital confetti… but still, something’s missing. In a remote setting, the real challenge isn’t if we’re talking — it’s how we’re showing up when we do. Because meaningful connection doesn’t happen by accident anymore. It’s not born in Slack threads or buried in bullet points. It happens through energy, intention, and a little bit of courage.
In the office, we used to rely on tiny, unspoken moments: nods in meetings, side chats in the kitchen, the kind of informal interactions that built trust over time. Remote strips that all away, which means we need to be much more deliberate if we want to create a connection that actually lasts.
Here’s what I’ve learned makes a real difference:
✋ Be proactive, not performative
We can’t just wait for team relationships to happen anymore – we have to build them. That means sending the message, scheduling the chat, jumping into the comment thread. These moments don’t need to be big, but they do need to be intentional.
👂 Listen to understand, not just to respond
In a virtual space, active listening becomes even more valuable – and harder to fake. I’ve found that repeating back what someone said, asking thoughtful follow-ups, and showing you’re really there creates space for connection, not just conversation.
🧠 Use the right channel for the right moment
Not every chat needs to be a meeting. Some of the best exchanges I’ve had have started with a voice note or a casual reaction to a LinkedIn post. Video call fatigue is real – varying how we communicate can make our touchpoints more human and less transactional.
🤝 Real relationships can happen virtually
Here’s something I’ve learned first-hand: you can form deep, genuine connections with people you’ve never shared a room with – if you’re intentional about it. Over the past year, I’ve built two meaningful professional relationships entirely through LinkedIn. We connected over shared values and mutual goals, and those conversations quickly became something deeper; the kind of connection that feels just as real as anything built in person. So much so, I’ve made plans to visit them next time I’m nearby.
So, don’t underestimate the power of small, thoughtful outreach. Whether it’s responding to someone’s post, dropping a message to say “this made me think,” or setting up a casual virtual coffee – how you show up matters far more than where you are.
Feeling Invisible (and What to Do About It)
One of the remote workers challenges no one warns you about is that weird, creeping feeling of being invisible. You’re showing up, doing the work, replying to the threads – but somehow, you’re not seen.
In a physical office, visibility used to happen passively. Someone would walk past your screen, overhear a client call, or catch the edge of your third coffee-fuelled brainstorm. Now? No one knows what you’re doing unless you tell them – which feels awkward, especially if you’re not naturally a “look at me” kind of person.
The trouble is, when no one sees your work, they can’t value it. And when that happens repeatedly, motivation drops, imposter syndrome creeps in, and opportunities start floating right past.
So what do we do? We get intentional about being visible – without turning into a walking billboard.
💡 Narrate your work, not just your wins
This isn’t about humblebragging on Slack. It’s about creating a narrative around your contribution. I’ve found that “here’s something I’m working through” lands better than “here’s what I smashed.” It opens the door to collaboration, shows thought process, and reminds people you’re not just quietly operating in a vacuum.
🧭 Anchor what you do to what matters
Don’t just talk about tasks – talk about impact. Instead of “updated the spreadsheet,” it’s “cleaned up client data so the sales team isn’t flying blind.” Show how your work connects to the bigger picture. People remember that.
🌱 Don’t confuse visibility with ego
This one took me a while to learn. Talking about your work isn’t bragging – it’s ensuring your contributions aren’t invisible. Especially in a remote environment, it’s not about self-promotion. It’s about self-advocacy.
🧠 If you’re a manager: create space for quiet wins
Some people will always shout louder. That doesn’t mean they’re contributing more. I try to actively notice the ones who are quietly holding everything together – and find ways to pull them into the spotlight. Ask, “What’s something you’re proud of that no one’s noticed yet?” You’ll be surprised what surfaces when people feel safe enough to share.
Too Many Tools, Not Enough Clarity
I think we can all agree, one of the most infuriating remote working challenges is when you’re juggling between 5 different forms of communication. Your tools – the ones that were supposed to make everything smoother – start slowing you down. Or worse, driving you up the wall.
Somewhere between the seventh Zoom invite of the day and the third platform no one really uses but no one’s brave enough to kill, remote work became… clunky. It’s not just bad Wi-Fi or app fatigue. It’s deeper. It’s decision fatigue. It’s cognitive friction. It’s a hundred little micro-moments where the tech gets in the way of the thinking.
Here’s how we start untangling it:
🔧 Reduce tool friction, not just tool count
Yes, tool overload is real. But even good tools can become painful if they’re used badly. One of the worst offenders? Tools without clarity. Who owns it? When are we supposed to check it? Why are there twelve versions of this document?
Instead of just deleting apps, map how people actually interact with the ones that matter. Where are the sticking points? What causes rework? Then fix those. Cutting tools doesn’t fix chaos. Designing for clarity does.
🧭 Create ‘digital traffic rules’ – and enforce them gently
Most remote teams don’t need new platforms. They need new agreements. Like:
- What’s async and what isn’t?
- Where do we give feedback? (In the doc? In Slack? In someone’s DMs at 11pm?)
- Is a calendar invite sacred, or a suggestion?
Get these norms written down. Not as policy, but as shared guardrails. When everyone plays by the same traffic rules, the road gets faster.
📶 Stop normalising terrible setups
If someone came into a physical office and their chair was broken, you wouldn’t just say “Tough.” So why do we accept glitchy Wi-Fi, echoey mic audio, or working off one tiny laptop screen?
If people are working remotely, they need the tools to do it well: better headsets, stipends for routers or ergonomic gear, quiet rooms for calls.
The Work-Life Blur
Ah yes, the great promise of remote work: flexibility. Work where you want, when you want, in clothes that may or may not include a waistband. And on paper, that’s exactly what we got.
But, for a lot of people, flexibility hasn’t made work easier. It’s just made it always there. The kitchen table became the boardroom. The 9–5 became the 7–11. And “I’ll just finish this after dinner” became “Wait, it’s midnight?”
This is one of the sneakier remote working challenges; the myth that we’re all enjoying perfect work-life harmony when really, the boundary line has completely evaporated. So, lets work out how to re-draw it.
🧱 Create fake boundaries that feel real
f there’s no physical office, you need to build psychological ones. I start my day with a fake commute – a walk around the block, a podcast in the car, something to create that “leaving the house” energy, even if I’m just going to the next room. End-of-day rituals matter too. Shut the laptop. Close the tabs. Change your environment. Signal to your brain that work mode is over.
🛠️ Design your week like a city – zones, not chaos
Instead of time-blocking every hour (which most people abandon by Tuesday), try zoning your week. Mornings can be for focus work, afternoons for meetings, Fridays for strategy and planning. You’re building flow, not friction. This also helps teams coordinate more easily – if everyone knows when you’re doing deep work versus when you’re up for a call, you get fewer interruptions and more respect for boundaries. Structure = freedom.
🧃 Replace “always available” with “always accountable”
This one’s big. Remote work thrives on trust, not presenteeism. Let people know what you’ll get done and when – not that you’ll be constantly online. I’ve started sharing simple “here’s my focus for today” updates instead of being permanently green on Slack. Visibility ≠ availability.
📣 Make your shutdown visible (and a little bit fun)
Don’t just log off – exit. You don’t need a formal sign-off script, but letting your team know “I’m done for the day” sets the tone. Bonus points if you make it light: a quick GIF, a “see you tomorrow, brain cells permitting,” or even a Slack emoji combo that signals “door’s closing.” Normalising shutdown rituals helps everyone feel okay about actually ending the day.
Culture Drift – How to Stop The Slide
One of the subtler challenges of remote working is culture drift – and it creeps in quietly. The energy changes. Messages get more transactional. Meetings feel like box-ticking exercises. The vibe that once made your team feel like a team is gone without any warning.
In the office, corporate culture was ambient – shaped by the everyday moments we didn’t even think about. Remotely, those don’t happen unless we make them happen. And if we don’t, culture slowly slips into the background, unnoticed until it’s almost gone.
Stopping the slide starts with intention – a few small shifts that can make a big difference.
🧭 Use culture check-ins, not just project updates
Culture drift isn’t just about what’s not being said – it’s also about what’s never being asked. Try starting a monthly meeting or async thread with questions like:
- “What’s one thing that still feels ‘us’?”
“What’s started to feel a bit… off?”
It opens up a culture conversation without needing a formal engagement survey.
🛠️ Turn default processes into culture touchpoints
Culture lives in how you do the boring stuff. Look at your day-to-day ops – onboarding, feedback loops, calendar invites. Are they cold, generic, overly templated? Or do they reflect what you actually value? I’ve seen people add voice notes to onboarding docs or rename their Monday standup “The Week Ahead & The Vibes.” It works.
🧃 Create one shared ritual that isn’t about work
It doesn’t need to be big or branded, but there should be something your team does that isn’t about hitting a deadline. A “drop your weekend photos” thread. A collaborative Spotify playlist. One team I know has a Slack channel where everyone posts what they’re snacking on. It’s silly – but it’s theirs. And that’s the point.
🧠 Lead with energy, not just efficiency
Culture follows behaviour – and if leadership is robotic, transactional, or just plain tired, that tone trickles down. Remote culture needs leaders who bring human energy. That could be as simple as ending a meeting with “what’s one thing that made you laugh this week?” or taking time to acknowledge effort, not just results.
The Recognition Recession
Here’s one of the most damaging remote workers challenges: career drift. The sense that you’re doing decent work, showing up, hitting deadlines… but nothing’s moving. No new opportunities, recognition, or sense of direction.
In the office, career growth was layered into the rhythm of the day. You got pulled into new conversations. Someone floated your name for a bigger project. A leader saw something in you, because they saw you. Remotely, those signals don’t show up unless someone deliberately sends them.
Without that structure, people feel like they’re stuck in neutral. But what’s getting in the way?
🔁 Stop treating development like a scheduled event
In remote environments, the “career conversation” often gets booked once a year and buried under performance metrics. That’s not enough. Growth needs rhythm – informal check-ins, reflection rituals, stretch debriefs. If you’re not talking about what’s next, don’t be surprised when people start looking elsewhere.
🤝 Mentorship is progression
In-office mentoring used to happen passively. Now it has to be built. That means finding ways to get people seen, challenged, and coached beyond their role. Create intentional pairings. Rotate responsibilities. Let people shadow strategy calls. If you want people to grow, put them where the learning lives.
🌱 Progress needs signals, not just goals
One of the trickiest challenges of remote working is mistaking capability for progression. “You’re doing great – just keep it up” sounds like praise, but it lands like a dead end. Growth needs feedback and forward motion. I’ve seen people benefit from learning logs, where they jot down one thing they got better at each week. It builds momentum, and gives leaders something real to reflect back.
Solving Remote Working Challenges Starts Here
If you’re struggling with the challenges of remote working, you’re not doing it wrong. You’re just navigating systems that were never really built for humans, let alone humans in different postcodes, juggling different time zones, inboxes, and energy levels.
These challenges aren’t fixed by throwing another tool at them. They’re solved by rethinking how we work together: how we lead, communicate, build culture, and grow. That’s where we come in.
At Farleigh, we help teams with tailored team and leadership development and expert culture consultancy – remotely, hybrid, or whatever comes next. If you’re ready to stop surviving remote work and start designing something better, let’s talk.