Why Remote Work Still Feels Hard (And What Makes It Actually Work)

In 2020, we wrote about how to manage remote teams:

Daily check-ins. Video calls instead of emails. Collaboration tools. Clear accountability. Visible leadership. Employee engagement.

Five years later, everyone does these things.

Zoom is infrastructure. Slack is standard. Daily standups happen everywhere. Collaboration tools proliferate.

But remote work still feels hard for most organisations.

Managers exhausted from “managing remotely.” Teams anxious about visibility. Productivity concerns constant. Culture feeling fragile. Isolation still widespread.

Why? Because the advice treated remote work as a management problem, not a systems problem.

What We Got Right (And Wrong)

Let’s revisit the 2020 advice and what actually happened.

We correctly said:

✓ Technology infrastructure matters
✓ Communication needs to be intentional
✓ Accountability must be explicit
✓ Supervision looks different remotely
✓ Employee wellbeing needs attention

All true.

What we missed:

✗ These tactics only work if systems underneath them work
✗ Remote work exposes problems that were already there
✗ You can’t “manage” your way out of systemic dysfunction
✗ The problem isn’t remote work—it’s broken Strategy, People, and Performance

After supporting 200+ remote/hybrid organisations, the pattern is clear:

Remote work works when systems work. Remote work fails when systems don’t.

The tactics (check-ins, tools, accountability) are just tactics. They amplify whatever system exists underneath.

Good system + remote work = high performance
Broken system + remote work = visible chaos

The Five Challenges Revisited

In 2020, we identified five challenges. Five years later, let’s revisit them with a systems lens.

Challenge 1: “Insufficient Supervisor Support”

Original advice (2020):
More check-ins. Visible leadership. Regular communication. Accessible managers.

What organisations did:
Daily standups. Weekly one-on-ones. Manager office hours. Leadership town halls.

What actually happened:
More meetings. Team feels monitored (not supported). Managers exhausted from constant check-ins.

The system problem:

If performance expectations aren’t clear, supervision becomes micromanagement.

Example:

A manager schedules daily 15-minute check-ins with each of 7 team members.

Time spent: 75 minutes/day just on check-ins (plus prep, plus follow-up)

Team perception: “She’s checking if we’re working. She doesn’t trust us.”

Manager intention: “I don’t know what they’re doing. I need to stay on top of things.”

Why this happens:

In an office, you could see who’s working. Walk by desks. Observe activity. Have impromptu chats.

Remote work stripped that away.

So managers compensated with more check-ins.

But the real problem: Performance expectations weren’t clear.

Managers didn’t know:

What does success look like for each person this week?
How do I know if they’re on track?
When should I be concerned?

So they checked in constantly—to find out what they should already know.

What actually works:

Clear performance expectations tied to strategy:

What are you accountable for this week/month/quarter?
What does success look like? (Measurable outcomes)
How will we track progress?

Weekly reviews focused on outcomes (not activity):

What did you achieve? (Results, not hours)
Where are you stuck? (Support needed)
What’s your focus next week? (Priorities)

Manager capability to coach remotely:

Ask “How can I help?” (not “What did you do today?”)
Focus on removing blockers (not monitoring presence)
Trust outcomes (not observe activity)

Example:

Same manager, different approach.

Before system fix:

Daily check-ins: “What are you working on today?”
Team feels monitored
Manager exhausted

After system fix:

Clear weekly goals for each person
Monday: Quick alignment on priorities (15 min team call)
Friday: Review what got done (30 min team call)
Ad-hoc support when requested (not scheduled surveillance)

Result:
Manager time: 75 min/day → 45 min/week
Team trust: Up
Performance visibility: Clear

The lesson: Supervision works remotely when expectations are clear. Otherwise, it’s just monitoring.

Challenge 2: “Access to Information and Collaboration”

Original advice (2020):
Use collaboration tools. Document everything. Over-communicate. Create knowledge bases.

What organisations did:
Bought tools (Slack, Teams, Asana, Notion, Confluence, Miro, etc.). Documented obsessively. Messaged constantly.

What actually happened:
Information scattered across 15 platforms. “Where’s that document?” daily. Decision-making slower. Collaboration chaotic.

The system problem:

Information is scattered because roles and workflows aren’t clear.

Example:

Team uses:

Slack (daily communication)
Teams (video calls)
Asana (project management)
Notion (documentation)
Google Drive (file storage)
Dropbox (also file storage)
Email (formal communication)
WhatsApp (urgent matters)

Daily questions:

Where did Sarah share that analysis? (Slack? Email? Drive?)
Who owns this decision? (Three people think they do)
Where’s the latest version of this doc? (Six versions in three places)
Who has access to what? (No one knows)

Why this happens:

Tools multiplied. But no one defined:

Who owns what information?
Where does each type of info live?
Who maintains it?
How do tools connect?

Result: Everyone documents everywhere. Nothing is findable.

What actually works:

Structure that matches how work flows:

Map how work actually moves (not how org chart shows)
Define ownership by process (not just by role)
Clarify handoffs (when does work move from A to B?)

Clear ownership of information:

Who maintains client data? (One owner)
Who documents process? (One owner)
Who updates project status? (One owner)

Integrated tools (3, not 15) with clear purposes:

Communication: Slack (daily), Email (formal)
Documentation: Notion (single source of truth)
Project tracking: Asana (status visible)
File storage: Google Drive (organized by team)

Decision: Kill the rest. (Access is burden, not benefit)

Example:

Before system fix:

8 tools, all used differently by different teams
“Where’s X?” asked 10+ times daily
Information duplicated across platforms
30 minutes/day just finding things

After system fix:

3 tools, clear purpose for each
Everything has one home
Ownership clear
5 minutes/day finding things

The lesson: More tools don’t help if structure is unclear. Define workflow first, then choose tools.

Challenge 3: “Distractions at Home”

Original advice (2020):
Set boundaries. Create dedicated workspace. Establish routines. Communicate your schedule.

What organisations did:
Encouraged workspace setup. Allowed flexible hours. Promoted work-life balance.

What actually happened:
People work 6am-9am, 12pm-3pm, 8pm-11pm. Boundaries disappeared. Burnout increased.

The system problem:

People work evenings and weekends not because of distractions, but because roles are unclear and work is poorly distributed.

Example:

Employee reports: “I’m distracted at home. Kids interrupt. Hard to focus.”

Actual schedule:

6am-9am: Work (before kids wake)
9am-3pm: Kids, household, interruptions
3pm-6pm: Kids homework, dinner
8pm-11pm: Work (after kids sleep)

Total work hours: 9 hours/day, split across 17 hours

Manager sees: Flexible schedule, accommodating home life

Reality: Working constantly because workload is unreasonable for one person.

Why this happens:

We diagnosed. Found:

Role overlaps with two other people (three doing redundant work)
Unclear what this person owns vs. others
Decision bottleneck upstream (work piles up waiting for approval)
No prioritization (everything “urgent”)

Real problem: Not distractions. Systemic overload.

What actually works:

Clear roles (who owns what):

Define scope per person
Eliminate redundant work
Clarify ownership (not overlap)

Reasonable workload (distributed properly):

Map actual time required
Align roles to capacity
Redistribute if overloaded

Flexibility that doesn’t mean “work all the time”:

Core hours for collaboration (e.g., 10am-2pm)
Async work outside core hours (by choice, not necessity)
Clear end of workday (not “whenever you finish”)

Example:

Before system fix:

Employee working 6am-11pm (with breaks)
Blames “distractions at home”
Exhausted, considering quitting

After system fix:

Clarified role (removed overlap with 2 others)
Redistributed workload (40% reduction)
Set core hours (10am-3pm collaborative, rest flex)

Result:

Works 9am-5pm most days
Distractions still exist (kids still home)
But workload now fits in reasonable hours

The lesson: Distractions aren’t the problem when workload is reasonable. Fix the system, boundaries become possible.

Challenge 4: “Technical Infrastructure”

Original advice (2020):
Ensure internet. Provide devices. Enable access to systems. Invest in technology.

What organisations did:
Bought laptops. Subsidized internet. Migrated to cloud. Upgraded bandwidth.

What actually happened:
Better tech. Still unproductive. Why?

The system problem:

Good infrastructure doesn’t help if systems are chaotic.

Example:

Company invested heavily:

New laptops for everyone ($2,000 each)
Internet subsidies ($100/month per person)
Cloud migration ($50,000)
Upgraded tools (Zoom, Slack, Asana, Notion)

Total investment: $300,000+

Productivity: Still low.

Why?

Infrastructure was great. But:

Strategy unclear (priorities changed weekly)
Roles overlapping (people doing redundant work)
Performance invisible (no one knew if on track)
Decisions slow (despite fast tech)

Good tech + broken system = expensive chaos.

What actually works:

Good infrastructure (yes, necessary):

Reliable internet
Proper devices
Access to systems
Security handled

Plus clear strategy:

Priorities stable (people know what matters)
Resources allocated (focused, not scattered)
Decision filter (what to say yes/no to)

Plus aligned structure:

Roles clear (who does what)
Workflows defined (how work flows)
Decision rights explicit (who approves what)

Plus visible performance:

Metrics clear (what success looks like)
Tracking consistent (weekly, not annual)
Feedback regular (coaching, not surprises)

Then tech actually enables productivity.

The lesson: Infrastructure is necessary but not sufficient. System must work for tech to help.

Challenge 5: “Isolation and Loneliness”

Original advice (2020):
Virtual social events. Watercooler chats. Team-building. Connection rituals.

What organisations did:
Monthly virtual happy hours. Weekly coffee chats. Quarterly team retreats. Slack social channels.

What actually happened:
Participation dropped over time. People still report feeling disconnected. Events feel forced.

The system problem:

People feel disconnected not because they miss office banter, but because they don’t understand how their work contributes.

Example:

Company runs monthly virtual happy hours.

First few months: Good participation, fun energy

After 6 months: Attendance drops from 80% to 30%

After 1 year: Cancelled due to low interest

HR frustrated: “We’re trying to build connection. Why don’t they care?”

We diagnosed:

Interviewed staff. Asked: “Why did you stop attending happy hours?”

Common responses:

“Feels forced”
“Another meeting on my calendar”
“Don’t feel connected to the mission anyway”
“Work feels transactional”
“Don’t see how my work matters”

The real issue: Not lack of social events.

It was: Unclear how their work connected to organizational goals.

Why this happens:

Isolation isn’t just social. It’s existential.

“What am I contributing?”
“Does my work matter?”
“Am I making a difference?”

When these questions have no clear answer, virtual happy hours feel empty.

What actually works:

Clear strategy (so people understand the mission):

Where are we going? (Vision clear)
Why does it matter? (Purpose meaningful)
How are we getting there? (Strategy makes sense)

Roles that show contribution:

How does my work fit? (Connection visible)
What happens because of what I do? (Impact clear)
Who depends on my work? (Relationships meaningful)

Performance tracking that connects individual work to outcomes:

What did I contribute this week? (Progress visible)
How did that move us forward? (Connection to goals)
What’s different because of my work? (Meaning)

Then social connection becomes natural:

People engage because they’re connected to mission
Events feel meaningful (shared purpose)
Relationships built around real work (not forced)

Example:

Before system fix:

Happy hours dying
People feeling isolated
Connection forced

After system fix:

Clarified strategy (everyone understands mission)
Showed how each role contributes (connection visible)
Tracked progress toward shared goals (collective wins)

Result:

Happy hours voluntary, well-attended
Slack channels active with work and fun
Relationships meaningful (built on shared mission)

The lesson: Connection isn’t about events. It’s about shared purpose.

What Makes Remote Work Actually Work

After supporting 200+ remote/hybrid organisations, here’s what we’ve learned:

Remote work works when:

✓ Strategy is clear → People know what matters, priorities stable
✓ Roles structured well → Work distributed reasonably, ownership clear
✓ Performance visible → People know if succeeding, feedback consistent

Remote work fails when:

✗ Strategy confused → People work hard in conflicting directions
✗ Roles unclear → Work overlaps, decisions stuck, people overloaded
✗ Performance invisible → People don’t know if on track, anxiety constant

The tactics (check-ins, tools, accountability) only work when the system underneath works.

The Updated Playbook

Don’t start with “how to manage remotely.”

Start with “is our system ready for remote?”

System Check 1: Strategy

Questions:

Can your team articulate the same priorities?
Do priorities change weekly or stay stable?
Does everyone know what success looks like?
Do people understand how their work connects to goals?

If no: Remote work will amplify confusion. Fix strategy first.

System Check 2: People

Questions:

Are roles clear (who owns what)?
Is workload reasonable (or are people drowning)?
Are decision rights defined (who can approve what)?
Do people know who to collaborate with (and how)?

If no: Remote work will create bottlenecks and overload. Fix structure first.

System Check 3: Performance

Questions:

Do people know if they’re succeeding?
Is feedback consistent (or just annual)?
Are expectations clear (or fuzzy)?
Can people see progress (or is it invisible)?

If no: Remote work will create anxiety and micromanagement. Fix performance systems first.

What This Looks Like: Before and After

Before: Remote Work Without Systems

Strategy:

Changes monthly
Priorities unclear
Everything urgent
No one knows what really matters

People:

Roles overlap
Decisions slow (unclear who approves)
Workload uneven (some drowning, others unclear what to do)
Collaboration ad-hoc (chaotic)

Performance:

Tracked annually (if at all)
Feedback rare (surprises at review)
Expectations fuzzy
People don’t know if on track

Management tactics:

Daily check-ins (feel like monitoring)
More meetings (to “stay aligned”)
Over-communication (because clarity lacking)
Constant supervision (because performance invisible)

Result:

Exhausted managers
Anxious teams
Mediocre performance
High turnover

After: Remote Work With Systems

Strategy:

Clear priorities (stable, not changing monthly)
Direction understood (everyone knows what matters)
Resource allocation defined (focus clear)
Mission meaningful (people connected to purpose)

People:

Roles clear (who owns what)
Workload reasonable (distributed properly)
Decision rights explicit (fast decisions)
Collaboration structured (efficient)

Performance:

Tracked weekly (progress visible)
Feedback consistent (coaching regular)
Expectations transparent (people know what success looks like)
Progress visible (people see contribution)

Management tactics:

Weekly check-ins focused on outcomes (30 min)
Fewer meetings (because priorities clear)
Targeted communication (because structure works)
Trust-based supervision (because performance visible)

Result:

Confident managers
Engaged teams
Strong performance
Low turnover

Final Thought

Remote work isn’t going away. Hybrid is the new normal.

But if it still feels hard, the problem isn’t remote work itself.

It’s that your Strategy, People, and Performance systems weren’t built for it.

You can’t “manage” your way out of systemic dysfunction.

Fix the system. Remote work will actually work.

Ready to Fix What’s Making Remote Work Hard?

If your organisation does all the “right” remote work tactics but it still feels chaotic, the problem isn’t the tactics.

It’s that your systems aren’t ready for remote.

Start with a 60-minute diagnostic conversation.

We’ll discuss:

Which system is broken (strategy, structure, or performance?)
Why remote work is exposing it
What it would take to fix it

No pitch. No obligation. Just clarity.

→ Book a Diagnostic Call

About the Authors:

Marilyn Were is Partner, Strategy & Change Management at Afribusiness Consulting. With 17+ years of experience in change management and remote transformation, she has helped organisations across Kenya, Uganda, Zimbabwe, Zambia, and Ethiopia build systems that enable distributed teams to thrive.

Annabell Karanja is Lead Consultant, Organisation Design & Human Capital at Afribusiness Consulting. With 16+ years of experience in HR and organisational design, she has led remote work transformations for 200+ organisations.

Afribusiness has supported organisations to distinguish between remote work tactics and system foundations that make remote work actually work.

Contact: info@afribusiness.co.ke | www.afribusiness.co.ke