Questions to anticipate when asking your manager if you can start working remotely

Deciding that you're going to ask your manager if you can transition from your in-office software developer job to moving to a new city and working 100% remotely can be a big decision. There are likely tons of concerns you have about how to approach this. You've probably practiced your pitch hundreds of times, thought through all kinds of details and prepared for every scenario you could think of.

A different approach

First off, a story. When I brought up the idea of moving and switching to a remote arrangement with my manager, I had been planning the conversation for days, maybe even weeks. I had played out every internal dialogue in my mind, imagining every scenario I could think of, what my "pitch" would be, why I was proposing this. When it came time to have the conversation I spoke for several minutes straight, basically vomiting out all my thoughts in what probably seemed like a well-reasoned but slightly incoherent ramble.

In short, the conversation started out one-sided. It wasn't until I stopped talking that my manager asked me a simple question, one that was so simple I hadn't thought to discuss - "So when are you thinking of moving?"

Assuming you have a good manager and have established a good relationship with them, they likely want you to succeed just as much as you do. They want to help you out.

This is not to say that you shouldn't think through things ahead of time, but is to say that it can be incredibly easy to focus only on what's in your own head and not what will be going through your manager's.

This is the wrong mindset to be in.

When you approach them about this, the dream would be you're so prepared and able to sell it so well that they can't say no. In order to do this, you want to get out of your head a bit and into your manager's.

When you're stuck in your head it becomes easy to make assumptions and miss obvious things. You lose a bit of the bigger picture and more importantly, context.

You might assume your manager is thinking what you're thinking... they're not. They likely want to say yes, but there will be a lot going through their head too.

Their concerns

In order to better anticipate the questions you may get asked, consider the following concerns your manager will likely have:

Costs - Managers typically have some sort of budget they oversee, one that they also need to report on to whoever they report to, even if it's just to the rest of their colleagues. Concerns with you working remotely may be how much it will cost the company (you may need to travel back to the main office once in a while, get setup with home office equipment, etc.) and affect the budget they manage.

Logistics - Logistics can get complicated quickly and concerns can range from bigger items such as how you will re-integrate with the team and how you will mentor others to more mundane things like desktop support. It is their job to keep things running smoothly so they won't want this change in work arrangement to affect day-to-day operations.

Legality - Fairly self-explanatory, will you legally be able to work in the city (or cities, if you plan on moving around) you are moving to, especially if it's in another country?

Politics - Another item that can get complicated quickly, but thoughts might be how will the organization and your team react to you working remotely, especially if the majority of the company works in-office and is HR going to present any hurdles.

Retention - If your manager is considering a remote work arrangement, they likely want to keep you at the company. Moving to another city where there will be new companies and a new network for you may introduce thoughts of a potential flight risk. Developers are a hot commodity and in short supply, so a move to a new city (especially if it's a big city or tech hub) may cause this concern.

Prepare

With these concerns in mind, use the below questions as a checklist to prepare yourself for the conversation. And don't forget that it's exactly that - a conversation. Between two people who will have overlapping and differing points of view and concerns.

• How long will this arrangement last?
  • Is this a short term thing, then you move back? Or more permanent?
• When exactly are you thinking of making this move?
  • This falls under logistics - your manager will probably have to get approvals from their boss if they have one and from HR, communicate it to the team, etc. They will also need a timeline to plan for this. And those concerns listed above - your manager will need time to think through them and get answers.
• There is an office in "X city" you are moving to - why not work from there?
• Are you expecting the company to pay for the move?
• Will you be willing and able to fly back for occasional important meetings, planning sessions, software version releases, team building events?
• For those with some sort of leadership responsibilities, how do you plan on transitioning those responsibilities either to someone else on the team or maintaining them in your remote role?
  • Remember that this does not necessarily need to even by a "leader" in title, but can be things like leading a small team or mentoring a team member.
• What will the timezone overlap look like?
  • Will you work the same hours as the main office? Will there be "core hours" where you overlap with the main office for several hours?
• Do you have the right communications and tools in place?
  • Do you have a laptop? Does it have VPN setup? Who can support you if the laptop crashes? Will the company need to provide you a cell phone? Do you have a video calling/conferencing solution in place for that visual connection?
  • Is there a documentation solution in place? All developers hate documentation, but it becomes ever more important to those working remotely.
• Are you going to forget to check in your code?
  • A concern for any developer, but even more so when you live in another city or are traveling, making it harder to get important code or documents off your computer should you fall ill or disappear.
• Are you going to jump ship as soon as you land?
  • This probably won't be asked out right, but you may get some form of this question.