Stay Classy, Contractor: A Survival Guide

Every office is a community, and most are weird little communities. Having hired contractors over the past ten years and now working as one, here are a few things I have learned to sort out the strangeness and up the niceties in the contractor lifecycle.

Insist upon introductions.
Pretend you are Alice in Wonderland, for just like that marvelous book, you will meet all sorts of characters who think you are quite odd. Many of them will perpetually be in a terrible hurry somewhere, but you do need to tell each person you meet your role, the length of your contract, what teams you are working with, and some relevant piece of your background experience. Stationing yourself near the printer is particularly helpful when trying to meet everyone.

Two bonus Alice tips: Avoid eating cakes in their entirety (or really anything lying around in the break room), and do not mention your cat.

Bring one piece of memorabilia in for validation.
Most of us in Contractor World have worked for at least one company in a long-term capacity. Doubtless, you received some silly swag from a company retreat, party, or from an industry event. I have a large glamour shot of a ferret with former colleagues' signatures that works well for this purpose. The reason to bring old office swag in? Something to point at if (when) someone mistakes you for an intern. Introductions mitigate the risk of this happening, but accept the compliment on your youthful vitality, point to the ferret image, and say, "I'm a contractor, actually. I'm hoping this office cherishes ferrets as much as my last office did."

Defeat the Mean Girls.
Ask for every style guide and documentation available to understand the office etiquette, even and especially from groups you may only be working with indirectly. Know the guides better than staff do. Often as a contractor you are marooned in a desk where you cannot know the email chains that encircle your reputation if you misstepped. Make sure to resolve any confusion face to face, always including HR, and take pains to thank your manager for helping you understand the office culture.

Serve up your opinion, but start through private channels.
One of the main things you'll miss as a contractor is that feeling of responsibility to a team, that ownership of some part of a project. Being copied on team emails can be deliciously tempting: a moment to step in and share your great insight! This usually backfires. Try emailing the project lead instead of replying to all and offer your opinion in a way that doesn't reflect badly or undercut anyone else's domain expertise. (e.g. "When I worked for ___, we solved this by _____ and it worked really well.") Be prepared for your vote to be ignored and your email unanswered.

Don't take the fish.
At one startup, about an hour before the weekly company meeting that the founders had introduced me at the week before, I was asked to leave. With a forced smile and assurances that "Google has police escort contractors out before meetings," my supervisor followed me back to the workspace island I was working from and then watched as I walked to the elevator.

Dropping the news right before a meeting makes your exit a walk of shame, so muster up a few casual "Rachel, I should have that document finished in about an hour," remarks on your way out, then work from remote during the private, recurring meeting. Make sure to submit your receipts from the coffee shop, and vow to ask about team meeting attendance first thing at the next job. Rejoice that you are excluded from some big, long meetings in this role.

Speak softly and carry a voided check.
Particularly at smaller companies there is unbelievable lag time about payroll. Be prompt in returning your W-9, contract agreement, and anything else that needs your signature. HR will be pleased that you share their devout belief that their forms are important. Use an invoicing service that allows you to see if a client has looked at an invoice and makes it easy to send gentle reminders. If at all possible, lawyer up enough to have someone who can call and inquire firmly about unpaid invoices.

Leave a forwarding address.
Mysteriously, after your email access is cut off, many unsolved issues on projects are attributed to you. Make sure to write your own goodbye email copying as many officemates as appropriate and address the email from your internal account to an external account; attach a document detailing your work. Do write a note to yourself on the overall experience and keep a record of the names of those you worked with so you can recognize them in future contexts. Try to assist the company by finding someone to replace you as the contract ends.

Above all, remember that 'permalancing' is not a word.

Kristen Taylor works with companies as a digital storyteller and content strategist. She drinks raw milk, blogs at kthread.com, and tweets from @kthread.

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