You may not realize it, but you don’t need to quit your job to work remotely. Most managers will consider remote arrangements if you present a solid case. Here’s how to build a strong business case to make it happen.
Step 1: Build Your Case (Before You Ask)
Document your professional wins for 2-3 months before requesting remote work. You’ll need proof you can deliver quality work without constant supervision.
Track these metrics:
- Projects completed on time or early
- Goals exceeded (sales numbers, tickets closed, campaigns launched)
- Times you’ve worked independently while your manager was out
- Instances where you solved problems without hand-holding
Save emails where your manager praised your work. You’ll reference these during your request.
Step 2: Know What You’re Actually Asking For
Be specific with your request. “Can I work from home?” is vague and easy to dismiss.
Define your request:
- Full-time remote or hybrid (which days)?
- Trial period duration (30, 60, 90 days works well)
- Your proposed schedule and availability
- How you’ll handle in-person requirements (quarterly meetings, client visits)
Starting with a trial period gives your manager an easy out if they’re nervous. It also gives you a chance to prove it works.
Step 3: Address Concerns Before They’re Raised
Managers worry about three things: productivity, communication, and team cohesion. Prepare to address these issues before you make your ask.
Your proposal should include:
Productivity plan: “I’ll maintain my current project load and continue our weekly check-ins. I’ll use [project management tool] to keep all deliverables visible.”
Communication plan: “I’ll be available on Slack 9-5 EST, respond to emails within 2 hours during business hours, and keep my calendar updated for video calls.”
Team involvement plan: “I’ll attend all team meetings via video and come to the office for [specific events/meetings] or with 48-hour notice when needed.”
Step 4: Time Your Request Strategically
The best time to ask is when you have leverage. Specifically:
- Right after completing a major project successfully
- During performance reviews when discussing goals
- When your manager is hiring and struggling to fill roles (shows remote work helps retention)
- After a company-wide announcement about flexibility or culture initiatives
Don’t ask during a crisis, right before busy seasons, or when your manager is under pressure. Choose your time strategically.
Step 5: The Actual Conversation
Request a formal meeting (don’t ambush your manager!). If your manager prefers written proposals, send a meeting request via email.
Email template:
Subject: Proposal for Remote Work Arrangement
Hi [Manager],
I’d like to discuss transitioning to a remote work arrangement [or: working remotely X days per week]. I’ve put together a proposal outlining how I’ll maintain my productivity and communication.
Over the past [timeframe], I’ve [specific accomplishment] and [specific accomplishment], demonstrating I work effectively with autonomy. I believe a remote arrangement will [increase my productivity/reduce my commute time allow me to start earlier/other specific benefit].
My proposal includes:
- A 90-day trial period starting [date]
- Daily availability 9-5 EST via Slack and email
- Continued attendance at all team meetings and [specific in-person commitments]
- Weekly progress updates using our existing check-in format
I’m happy to adjust this based on team needs. Can we schedule 20 minutes to discuss?
[Your name]
Step 6: How to Handle Objections
“We need you in the office for collaboration.” Response: “I can come in for [specific meetings/days]. For daily work, I’ll be more accessible via Slack than I am at my desk since I won’t be in other meetings.”
“How do I know you’re actually working?” Response: “Judge me on output. I’m proposing we track [specific deliverables]. If my results drop during the trial period, we can revisit.”
“It’s not fair to the rest of the team.” Response: “I understand. Would you be open to offering this to others who want it? I’m happy to share what works during my trial.”
Step 7: Get it in Writing
Once approved, send a follow-up email summarizing what you agreed to:
- Start date
- Schedule (which days remote/in-office)
- Trial period length and evaluation date
- Specific expectations
This protects you if your manager leaves or “forgets” the arrangement.
If They Say No
Ask what would need to change for them to reconsider in 6 months. Get specific requirements, then deliver on them and ask again.
If it’s a hard and final no, it may be time to start looking for a remote role. Some companies will never adapt, and that’s valuable information about your future there.
Remote work is a legitimate way to work if you’ve earned trust and can demonstrate results. Most reasonable managers will work with you if you have a good work history and you bring a solid proposal to the table.
Good luck with your proposal!
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