How to Ask for Remote Work (And Get a Yes!)


At Sunsama, we embraced remote work long before it became a necessity for most companies during the pandemic. Back in 2019, after completing Y Combinator's accelerator program, our small team made the intentional decision to go fully remote.

Over four years later, that pivot to remote-first has paid off. Our globally distributed crew operates like a well-oiled machine, iterating rapidly and staying aligned through our virtual rituals.

We've distilled the best practices from our years of experience making the case for remote work in this post. We'll guide you on how to ask for remote work and make your pitch as compelling as possible

Let's start with the most critical first step - being crystal clear on exactly why you want to go remote in the first place.

Be clear on why you want to work remotely

You must first articulate your motivations to yourself. This clarity will help you communicate your request with conviction. A clear understanding of your motivations and goals for seeking remote work shows that you have given the matter serious thought. It demonstrates that your request is not casual or impulsive

Your 'why' will allow you to provide specific, tangible reasons behind your request. For instance, if you want to reduce distractions like office chatter, mention how working from home can increase your focus and productivity. If you have personal responsibilities, such as caring for aging parents, share that to highlight your need for a flexible schedule.

It doesn't have to be some noble cause. Maybe you want more flexibility to travel and explore new places. Maybe the city your office is in doesn't fit with your lifestyle anymore. Whatever it is, be upfront about it.

Getting crystal clear on your motivation also helps manage expectations if your boss eventually shoots down the idea. Is remote work an absolute must for you or just a nice-to-have? Knowing where you truly stand will determine your next move.

Gather supporting points

We all know the generic stats and studies about how remote work can boost productivity and well-being. But your boss doesn't just want to hear the textbook points β€” they'll want to know how you specifically would handle working remotely for your company.

Gather some supporting points to make your case for remote work. The key is identifying real, tangible examples from your own track record versus hypothetical situations.

Here are some ideas, and questions to help you gather proof points that demonstrate you already have what it takes to thrive as a remote employee.

  • Experience: Think back to when you've worked remotely for the company before, even if temporarily. How did you perform during those stretches? Can you point to specific projects, tasks, or metrics that show you were successful working remotely?
  • Effectiveness: If you currently have a hybrid setup with some remote days, reflect on those days specifically. Identify examples where you delivered work high-quality work, attended meetings, and collaborated with the team while off-site. See if colleagues can provide testimonials about your ability to work effectively remotely on those days.
  • Collaboration: Take stock of the virtual tools you use effectively - video conferencing, messaging, project management apps, etc. If you've ever taken the lead on remote projects or virtual meetings, highlight your ability to facilitate and organize these activities.
  • Independence: Note down instances where you've met deadlines or delivered high-quality work while working independently or with minimal supervision.
  • Security: Highlight your knowledge of the company's cyber policies, software, and systems required for secure remote work.
  • Set up and Tools: Describe your home office setup or dedicated workspace, including any equipment or tools you have to ensure productivity and professionalism.

Initiate a conversation

When initiating the conversation about remote work with your boss, it's best to request a meeting in person rather than starting over email. An in-person discussion allows for a more nuanced conversation and reduces the chances of an outright dismissal before you've had a chance to make your case.

Instead of spilling the beans ahead of time, keep it vague when requesting the meeting. You could say something like:

"Hey, I had a couple of ideas I wanted to run by you about potential adjustments to my work setup. Think we could find a half-hour to discuss this week? I believe these ideas could really benefit my productivity and alignment with company goals."

Your goal here is to get a face-to-face meeting and plant the seed that this is an important discussion that could be mutually advantageous. Then once you're face-to-face, you can fully dive into your prepared talking points.

Present your remote work plan

When the time comes for the face-to-face meeting here's how you can start the meeting β€”

"Thanks for taking the time to discuss this. I've been thinking a lot about how I can really take my productivity and work to the next level. After weighing the pros and cons, I truly believe a remote work setup could be a game-changer for me and beneficial for the team overall. I've put together a detailed plan to show how it can work."

Then talk about how you've thought about thriving in a remote environment while continuing to contribute at a high level to the team's success.

Here are some key elements to include as you put that plan together:

  • Work Schedule: Clearly define your working hours to ensure availability for meetings and collaboration with teammates across different time zones if necessary.
  • Communication Strategy: Detail how you will communicate with your team and supervisors. This includes the tools you'll use (like Slack, email, Zoom), the frequency of updates, and how you will be available during work hours.
  • Set-up and Tools: Describe your dedicated home office or set up in a distraction-free space with all the tech, webcam, monitors, etc. Highlight how you plan to ensure work is not disturbed by internet issues.
  • Security Measures: Describe the steps you will take to secure work data, especially if you deal with sensitive information. It might involve using VPNs, secure passwords, and following the company's IT security guidelines.
  • Daily rituals: Propose replicating daily planning and review routines asynchronously by sharing in team channels. For example, we use Sunsama to plan our work day and then post our daily plan to a Slack channel. It's an async version of a daily standup meeting. Sharing our daily plan keeps us focused, and calm, and helps us realize when a teammate might need help.
  • Weekly review: Suggest an asynchronous weekly review or team update using recorded videos or written docs.

πŸ‘‰ You can duplicate the weekly review template we've created for you in Notion as a starting point here. Then customize it to fit your needs.

The key is showing you've thoughtfully accounted for all aspects of making remote work successful, not just for yourself, but for the team and company as well. Come over-prepared with a concrete operating plan your manager can support.

Anticipate the objections and come prepared

While the details of your plan may seem comprehensive on paper, it's natural for your manager to have some concerns or unanswered questions. After all, transitioning an employee to remote work represents a significant change that impacts the entire team dynamic. As you outline the logistics of your proposed setup, take a step back and try to view it from your manager's perspective. Think about some of the objections they might have and prepare responses for those.

Based on our conversations with professionals across various industries, here are some common objections, along with responses to address them:

Objection: If I allow you to work remotely, I'll have to allow everyone to work remotely.

Response: "I understand the concern about setting a precedent. However, remote work arrangements can be evaluated and approved on a case-by-case basis, considering each employee's role, responsibilities, and ability to work effectively remotely. My plan outlines how I can not only maintain but potentially enhance my productivity while working offsite. It's not a one-size-fits-all approach; other employees would need to present similarly comprehensive proposals tailored to their unique circumstances."

Objection: How can I be sure you'll remain as productive and focused without the office environment?

Response: "I've included specific productivity metrics and goals in my plan that we can closely monitor during the trial period. Additionally, the processes I've proposed, such as daily planning, regular check-ins, and weekly progress updates, will provide full transparency into my work and output. If at any point my productivity dips, we can re-evaluate and adjust accordingly."

Objection: What about spontaneous collaboration and team dynamics? Won't remote work hinder that?

Response: "You're absolutely right, maintaining strong team collaboration and dynamics is crucial. That's why I've included detailed strategies for virtual meetings, whiteboarding sessions, and leveraging collaboration tools we already use successfully. While the format may be different, I'll remain actively involved in all team activities and projects, just in a virtual capacity. The daily/weekly sync-ups I've proposed will also help foster that team spirit."

Objection: I'm concerned about security risks with you accessing company data and systems remotely.

Response: "Data security is a top priority for me as well. My plan outlines the robust security measures I'll have in place, including a secure home network, VPN access, multi-factor authentication, and strict adherence to all company IT security protocols. I'm happy to work closely with our IT team to ensure we have rigorous security practices for remote access."

The key is to make it a cooperative conversation, not a debate that you want to win. Approach it as two parties working together to find solutions - not you trying to overcome their objections. With this mindset, you'll be able to reinforce your preparedness.

Suggest a trial

If your manager seems hesitant or has reservations about you permanently transitioning to remote work, suggest starting with a trial period. The key is positioning it as a low-risk opportunity to put the plan to the test, with ample communication and an exit ramp if needed. Come prepared with specific suggestions on trial duration, feedback cadences, and metrics to measure success.

You can say something like this β€”

"I understand that remote work is a big change, so let me propose we go for a trial period first. This will give us a chance to put my plan into practice and see how it works before deciding on anything permanent. For the trial, I suggest X weeks/months. It will provides enough time to work through any initial kinks and see the processes in action over a realistic stretch.
During the trial, we can hold weekly check-ins to discuss what's working well, potential issues, and make any needed adjustments along the way. I'm committed to an open feedback loop.

And of course, you'll have full visibility into my productivity metrics, responsiveness, and meeting attendance - all the factors we've discussed. We can evaluate impartially if I'm able to maintain the same level of performance remotely."

This message will allow your manager to agree in principle while removing the pressure of a permanent decision. It's a wise approach when proposing something like remote work that represents a big change.

What if they still say no?

While you've made a strong case for remote work and addressed potential concerns, there's still a chance your manager may not approve it, at least not right away. Have a plan for how you'll react and your next steps.

It's important to stay composed and professional. Don't argue or get defensive. Express that you appreciate them considering your proposal, even if the answer is no for now. Reacting emotionally could hurt your case long-term.

You can ask for specific feedback on why you won't be allowed to work remotely. Based on the feedback, you can decide if you want to press the issue or let it go for the time being. If you still feel strongly, you can ask to revisit the conversation in 3-6 months.

If remote work is an absolute must for you and not something you can compromise on, be prepared to make difficult decisions about your future with the company. Have an exit strategy if it's a dealbreaker.

The key is to have a productive discussion about why remote work was not approved and determine if there is a reasonable path forward or not. Avoiding an emotional reaction and approaching it as a dialogue keeps lines of communication open. With patience and flexibility, you may be able to change your boss' mind over time.

Build your compelling case for remote work with sunsama

As you prepare your proposal for working remotely, having a structured daily planning process will be key to demonstrating your readiness. With Sunsama, you can establish productive habits and documented routines to show that you have what it takes to thrive in a remote setup.

Sunsama is a powerful daily planner designed for busy professionals like you. By using it consistently, you'll be able to:

  • Plan and visualize your daily tasks and schedule in a structured way
  • Record daily review to document your progress
  • Highlight milestones achieved and roadblocks overcome
  • Build a data-driven history of your productivity
  • Prioritize deep work without any distractions

When presenting your remote work plan, you can draw from your Sunsama dashboard. Show your manager clear examples of how you prioritize deep work, meet deadlines, and remain focused - all without the constraints of an office.

Start your 14-day free trial of sunsama.

Don't just tell your boss you can be a productive remote employee - use Sunsama to show it. Solidify your remote work habits today and strengthen your case.


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