Convincing Your Boss (or Team)

Checklist for Convincing Your Boss (or Team)

If your going-remote plan includes the need to convince your boss, then the first step is to complete the Questionnaire for Individuals: Are You Ready to Work Remotely? This is because the ammunition you’ll need for convincing your boss will come from your written-out YES answers to the various questions; those answers will demonstrate you’ve got what it takes to make your remote venture a success. (Ideally you’ll have very few items—if any—remaining in your NOT YET camp before you broach the subject with your boss.)


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To begin your boss-convincing plan, let’s turn again to the Meghan M. Biro comment quoted earlier, this time in full:

“When my role is to be a virtual team member, I need to be self-motivated, focused, curious, flexible, and, above all, collaborative. When my role is to be an entrepreneur managing virtual teams, I need to be empathetic, emotionally intelligent, sensitive to what others need, and willing and able to provide whatever tools are necessary for success. In either role, I must … be self-aware—in tune with my skills, capabilities, strengths, and weaknesses.”

This time, consider this description in light of your manager. Do you think she or he is “empathetic, emotionally intelligent, sensitive to what others need, and willing and able to provide whatever tools are necessary for success”? Perhaps that’s too much to know the answer to right away, but keep it in mind as you proceed.

Regardless of how well received your request to work remotely might be, you’ll want to take the time to consider the prospect from your boss’s perspective. What about productivity? Reliability? What about team morale? From there, the goal is to decide how best to demonstrate that you’ll be fully accessible, responsive, and, above all, productive.

Another major consideration: pretty much every expert says that if one team member works remotely, even just some of the time, then the team needs to function as if everyone were remote. At first blush that sounds like a tall order, but it’s also true that the work practices of remote teams are superior to standard on-site practices—because they call for everyone being more intentional in their actions. Even just advertising how to be reached when—as well as what one is currently working on—communicates to everyone the dedication to the mission that every team member and team leader wants to see.

Now, the task at hand, broken down into steps.

  1. So that you’ll be well apprised of all the concerns your boss or team might have, you’d be wise to read Chapter 5: Transitioning Toward the Remote Option, especially the “Actually Going Remote” section, as well as the entirety of chapters 7 through 9. (Chapter 10 is less relevant to your objective here.) Along the way, take notes regarding what applies to your work situation, as well as what new practices or tools would be called for. (The items that follow share more about what kind of notes you should take.)
  2. Draw up a first-draft plan of what you would need to do or acquire in order to work as successfully as you do now. (This task will be well informed by the to-do list you created from your “Are You Ready to Work Remotely?” questionnaire.)
  3. Consider how to quantify all that you do. At the very least, you’ll want to pitch just how you’ll demonstrate that you’re fulfilling all your obligations while working remotely. If possible, show how going remote will add value.
  4. Draw up a first-draft plan of what you think your team would need to do (or acquire) in order to maintain the team’s current level of productivity with you working remotely.
  5. Spend some time thinking through the likelihood that your team would be willing to adopt the practices necessary to maintain your current level of productivity.
  6. If you’re starting to think this all might be a tough sell, consider getting feedback from your teammates: share what you’re contemplating and ask how receptive they might be to your plan.
  7. Prepare a proposal and timeline to present to your boss that addresses the following:

Finally, schedule a time to meet with your boss and present your proposal—perhaps with him or her reading it with you right there, ready to answer any questions. While the shyer ones amongst us might prefer to simply submit the proposal and wait for a reply, that approach could also lead to some pretty nervous hours, days, or even weeks before your boss gets back to you. Taking this more assertive approach would be one way of demonstrating just how serious you are about making this work.

Parents Working From Home