How to Convince a Skeptical Boss that Remote Works

Dear Sophaya,

I work from home three days a week and have done for a long time. My job requires a lot of concentration. Since the office is open-concept; it can be extremely distracting to get work done. Our office has a lot going on and there are a couple of people who constantly interrupt me with non-work related stuff. I have a good balanced routine going and I believe I am well respected by my colleagues and senior leaders. I always meet my deadlines and have received great job performance reviews for the 3 years I’ve worked here.

Recently I got a new boss. He has made it clear that he thinks anyone who works from home is “a slacker”. He’s convinced that the only way an employee can be productive is if they come to the office daily. I really value my current schedule as it cuts down on my 90-minute commute plus I can work my preferred hours, get my job done without interruption and still get to the gym once in a while without sacrificing deadlines. I’m worried my new boss is going to change things. I’m not sure what I’m going to do if he tells me I have to come into the office every day.

How do I convince him I can be trusted to work from home?


Anxious at home

Dear Anxious,

Addressing existing biases against remote work is a drag but it’s pretty typical since there are still many people in the workforce who are suspicious of the practice. Bosses get anxious because they haven’t done it themselves or they have had a bad experience in the past. While this is changing somewhat, there is still a fair amount of ignorance and suspicion, particularly with older managers who think line of sight automatically means productivity (the jokes on them since remote professional know this is just pure fantasy). You and I know how efficient and productive remote work can be because we know how to organize ourselves and stick to our deadlines.

Our best advice for managing a skeptical boss is bring up the topic yourself rather than waiting for him to do it. At least then you can lead the discussion rather than waiting for the bad news then reacting with dismay when something happens you don’t like. Think of this as a mini job interview – do your prep before you have this conversation. Build a business case that emphasizes YOUR professional capability regardless of your work location. This doesn’t have to be braggy thing, just focus on your skill sets and expertise. Lay out your normal  remote work process for him. Walk him through how you organize yourself to meet your deadlines. Enlist the help of other respected voices as references e.g. if your old boss is still around, ask them if they will vouch for you and speak to your successful track record. If all else fails, ask for a trial period to prove your capability. Negotiate check-ins, ways to demonstrate you are available regardless of your location and success metrics so there is agreement on how your performance will be measured.

If your case is good and your new boss has a heart, then he’ll give you the benefit of the doubt. Fingers crossed for you! Hopefully taking the initiative followed by your stellar ongoing performance and professional follow-through just may convince him that remote work is the way to go!

Best of luck, let us know how it goes!

Photo by Igor Miske