Ask Sophaya: How to manage two jobs during a transition while working remotely

Ask Sophaya: How to manage two jobs during a transition while working remotely

Ask Sophaya Remote NationDear Sophaya,

I am transitioning from one job as a fundraiser working in a central office to another job where I will be an event organizer working remotely. During the transition, which will take several weeks, I’ll be working for both companies remotely. Some of the work will get done while I’m traveling; the rest will be from my home office. What suggestions do you have for managing two jobs remotely?

–Remote worker in transition

Dear Remote Workers in Transition,

Congratulations on the new opportunity, it sounds fabulous! We wish you ALL the best! You have an interesting and unique situation as each of your stakeholders – old job, new job – really need different things from you yet the remote work skills needed for both jobs are the same.

First things first, schedule time with both your bosses and key team members to set expectations and negotiate the basics.

Considerations for your current fundraising position:

Appreciate that they aren’t used to you working remotely plus they know you’re leaving. It’s likely they will worry you are going to leave them hanging and in your absence, things could go badly if you aren’t transparent, available and consciously in touch throughout this period. They will need to feel you are still engaged even though you are out of the office working on new stuff so prep them for your physical absence by reviewing your game plan for your transition up front.

  • Define your deliverables with everyone face-to-face if at all possible. Include identifying delivery dates and dependencies so everyone understands what you are doing during this time.
  • Be clear on your schedule, availability and contact info so everyone knows when and how to reach you.
  • Make sure to let everyone know what it will look like when you are unavailable as well. Luckily there are lots of ways to do this through automated notices via email or setting your availability status via tools like Skype or IM.
  • Check that you have access to all files, documents, info you need to get your work done – this means electronic access regardless of where you’re located.
  • Make a point of sending key players informal communications periodically through quick channels like IM or text. “Just thinking about you, have a great day!” “Thanks for sending over that report, very helpful!” These informal touchpoints let folks know you are still there even if you happen to be remote.
  • Schedule routine check-ins with your boss – these can be via email update or via phone/video chat, whatever works best for your boss. This will help eliminate any concerns which occur if there is too much silence. If your boss is used to having you in their line of sight and consult you often, then you need to check in more often at agreed upon times. This is where clear expectations will come in handy.
  • If someone has been hired to replace you and they are starting as you transition, make sure to add this to your expectations conversation…you want to do what you can to set them up for success and not undercut them during their initial days, but you also want to be realistic about how much time you can devote to their training when you are remote.

One small thing, I don’t recommend you talk about the new job with any of your old team if at all possible. If you show too much enthusiasm for the new position, your old team could take offense or assume you’ve checked out – why burn that bridge?

Starting out right with your new position:

Appreciate that new remote workers need to take a lot of initiative to connect with their new team. Folks don’t know you, they aren’t familiar with your working style and they have jobs of their own…presumably they are pretty busy with their own stuff so scheduling time to “meet” them is a crucial way to show respect.  Some of the steps for accommodating the new job are similar to the last list, but there are crucial differences.

  • Define your role, responsibilities, current priorities and standing deliverables is a must so you can organize yourself and figure out how to accommodate both your to-do lists.
  • Also, presumably, there will be some opportunity to do some new hire orientation, training or something so you can get at least some foundational information to get yourself started. I’d recommend pulling together a list of questions so you can show initiative without making any assumptions right away. Here’s a few to get you started. E.g. Is there an approved vendors for events, organizational preferences as to how events run, is there an existing schedule for events for the rest of the calendar year, what are the organization’s pet peeves, how do you do deposits for stuff like event venues, what’s the reimbursement process for any out of pocket expense, do you get a corporate credit card, are there existing budgets for stuff, are there spending limits, do you have contract signing authority, etc.
  • Be clear on your schedule, availability and contact info so everyone knows when and how to reach you. Make sure to adjust your preferences to suit your new team’s communication protocols, any team norms that are in place and team scheduling preferences. Accept that you may have to adopt two ways for a short period of time to suit old/new circumstances.
  • Make sure to let everyone know what it will look like when you are unavailable as well. Luckily there are lots of ways to do this through automated notices via email or setting your availability status via tools like Skype or IM.
  • Check that you have the devices, system access to all files, documents, info you need to get your work done – this means electronic access regardless of where you’re located. It may also mean a system review with someone who knows where to find things and how to get things done.
  • Make sure you know the organizational structure and have identified resources you can call upon to answer questions and help you get things done.
  • Make a point of introducing yourself to your new team members. As a remote professional, it’s up to you to tell people a little about yourself. Share a few personal details that illustrate your personalities, work style and approach to projects. I always tell people I’m a geeky foodie who likes to sail, cook for crowds and who hates a lot of drama. I take work, but not myself, seriously and I naturally assume the best unless proven otherwise.
  • If possible, use video or at least the phone rather than just email to connect with new colleagues initially. If face-to-face is possible, make the effort. Whatever you can do to show people you are more than just a disembodied voice or words on a screen makes you more real to your new teammates.
  • Schedule routine check-ins with your boss – these can be via email update or via phone/video chat, whatever works best for your boss. I recently wrote a post on creating visibility with your boss and your team. This will help eliminate any concerns which occur if there is too much silence. If your boss is used to leading remote teams, they will understand the value of routine touchpoints. If they are less experienced, then the onus will fall on you to push for the time so you can stay top of mind with your new boss.
  • When you start a new job, you have a short window – I like to call it the “honeymoon” period – when you can ask lots of questions. As you are the new person on the team, you aren’t supposed to know anything so you get to ask anything. When you work remotely, ask questions but do it in an organized way. Compile your questions and then schedule time with the right resources. Send the questions in advance so they can review them beforehand.

As with your old position, I don’t recommend you discuss the transition arrangement too much with anyone as it could cause confusion or undercut their confidence that they have your full attention. Instead, I’d focus on a clean transition with the old team and establishing a good first impression with the new team for your best future success!

Let us know how it goes!!

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