Week #9: Convince your boss you're ready to start working remotely 😎

Thanks for opening this letter. Happy to have you back for another week!

What will you find in today’s letter?

  1. Not fully remote yet? Convince your boss to go remote.

  2. Attend our next Remote Huddle on Tuesday at 1pm EST. Save your spot now.

  3. A great resource for scaling and transforming remote teams!

This week’s read

How To Ask To Work Remotely Full-Time

  1. Ensure you’re providing value. You can do this by becoming a top-performer, crushing your quarterly goals, or creating onboarding documentation because nobody else wants to take ownership or responsibility.

  2. Understand your “why”. If you’ll be standing in front of your boss or maybe even your whole leadership teams, it’s crucial that you have a clear reason why you’re asking to go remote. It’s a question you’ll get asked, no doubt. Try to take a step back and ask yourself, “why do I want to work remotely?”. Whatever your answer is it’s a valid answer and unique to you.

  3. Work up a plan. Before starting the full conversation or setting up a meeting with your CEO, type up a plan. You’ll want to map out your why, the pros, the cons, where you’ll work remotely, how flexible your schedule will be, your communication plan with your team, what equipment you have to be successful, and the equipment you’ll need.

  4. Set up a meeting. After you’ve got 1-3 on lock, it’s time. Gather the key folks that you need to get approval from - that maybe your direct manager, HR, and your CEO (depending on your company size). And crush your pitch.

  5. Experiment with a trial period. This makes everyone feel more comfortable with the idea of working remotely. If it doesn’t work out then we go back to the way things originally were.


🔨Give this a try! At my last job, I did a ton of research on remote work and ended up creating a presentation for my exec team. The presentation was essentially a pitch showing how I’d be a great candidate for remote work. Well, it went pretty well and I got the team approval to go fully remote. Today, I’d like to share the pitch deck I used - you can find it below.

Download the pitch deck

📅Join our Remote Huddle on Tuesday, 1/21! On the webinar will be the founder of Pragli, Vivek Nair. Pragli is a virtual office tool for remote teams.

We’ll talk about the importance of video collaboration and his background with remote work. Also, bring your questions about remote work, challenges, finding a job, and more for Q&A.

Send me the invite

🔍Resource! Last week I had the opportunity to chat with Shauna Moran, who is the founder of Operate Remote. She works with leaders to transform their teams into high performing remote teams through coaching and mentoring. If you’re looking for someone to help your team build healthy habits, processes, and make your organization successful at working remotely get in touch with Shauna by visiting her website here.

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👋See everyone next week! As always hit ‘reply’ if you have any questions.

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