You have decided to work from home. Telecommute. Listen to the kind of music you want to – dance the way your body tells you. Shower less, love more.
La-di-freaking-da – you still need to convince your traditional in-office boss to let you do it.
We just need to fix these concerns one-by-one in a detailed manner. You need to think through and deliver a proposal – and then you need to be a badass and execute it. He is most concerned with Performance and Communication.
You need to show that for you working offsite is more productive. Tell him why and then show him its true.
Can IT improve work-life balance?
Ask if you can hole up in a conference room for the afternoon, and then show him scary results.
Ask if you can work from the coffee shop/hotel across the street, and then show him scary monster results.
Ask if you can work from home one day and then show him scary monster-who-is-taller-than-average results.
There are two fears about communication – one specific fear is that you won’t be productive simply because you will be out of the loop and the other is that you will be a roadblock that holds up others.
For status the simplest method is to email what you are planning to do at the beginning of the day, and email at the end of the day with what you did. This also acts as a clock-in/clock-out mechanism for the more paranoid set. Over-communicating is a good place to start – you probably aren’t offering twice-daily status updates in person now.
Offer to share your to-do list. When you work from home you will need more structure than you had before so you will most likely be documenting more anyway. Use one of the many tools (RTM, Workflowy, Toodledo) that offer sharing so that your boss can (but most likely won’t often) see that you are in fact adding and deleting items that he recognizes.
For team communication it is harder to stay in the loop. You need some infrastructure in place: broadband internet, slower internet or a close Wi-fi backup, Skype, clear phone, etc. You will need to have your cellphone with you all the time when starting out and will need to act like you are in the office: if you need to run a 30 minute errand or have a doctor’s appointment tell someone.
For on-the-fly information and politics it gets much harder. Since clearing communication roadblocks across the team might (absolutely should) be part of your boss’s job you are indirectly asking him to do more work by communicating differently with you so avoid any special cases that require him to do anything just for you.
Take the initiative on your own to identify how real information travels around the office and make sure you can show him what proactive steps you will take. e.g. “I’ll still be on the morning call and I’ll message Cathy around lunch to see if anything comes out of the Thursday interdepartmental fist fight that seems to always determine our priorities”.
Being in-office also helps – offer to do 3 work from home days and 2 non work from home days. If the days are typically the same (i.e. there is no big planning meeting) offer to still come in on Mondays and Fridays. This calms his SpongeBob nerves as an irrational fear of ninja three day weekends is common. On the days you do come into the office you should turn into a total water-cooler guy and try to catch up with people to see if there is anything you need to know.
So you give him your plan – I’ll work Tuesday – Thursday from home from 7AM to 4PM, be available over IM, on Skype as needed, dial into the stand-up meeting, share my todo list, keep in touch with Cathy about politics, call you once a week if I haven’t seen you, etc.
Setup a timeframe of one month in which you will execute this plan. Tell him that at the end of it if he feels that you got less done you’ll give him the vacation days you would have earned over the period back. If you are a contractor offer to not be paid for 2 of the 20 business day in play, or 10% of your billed time over the period. Also – you should fully intend and be ready to make good on this.
The reason this works is that you are putting a stake in the ground and providing a mutually beneficial outcome for both parties. The boss knows that he is still in charge but has an employee that is taking initiative and will get things done. The added benefit to you is that it puts you in the right frame of mind – the absolute most important thing to understand about working from home is that it is all about execution.