Don’t spend time searching for work from home jobs. You can keep the job that you love, but do it remotely – if you have the right plan to influence the right people. I was a remote work pioneer for The Clorox Company – one of the very first fully remote brand marketers. I went remote back in 2010. What started as a 3 month remote work experiment led to 8 years of me leading large businesses and distributed teams from 3 time zones away in my home office in the Philly suburbs. One of the most frequent questions I am asked is “How do I ask my manager to work remotely?”.

Here are 4 steps to give yourself the best chance of getting your boss to say “Yes” to working remotely.

1. Understand yourself

  • While the work/life integration benefits of working remotely might be enticing, it’s important to know that it can also be EXTRA work to be really successful, especially if you are working in a distributed team where the majority of people are co-located. So, before you move forward, check in with yourself on areas like these…
  • Are you an introvert or extrovert? Extroverts should figure out how they’ll get the interaction they need to draw energy from being around others. Will you be able to get your team to enable remote access to things like team happy hours, or a co-worker’s baby shower celebration? Introverts will need to decide how comfortable they will be with asserting themselves via video or phone call with their team members and senior leaders. It can be hard enough finding your voice when you’re in the room, but it’s an added challenge virtually.
  • Are you willing to put in the extra time to influence from a distance? When you are co-located you get the opportunity to influence and build relationships in some of the smallest moments, like the elevator ride or a discussion at the water cooler. When you are remote you will need to recreate those moments virtually.
  • Can you manage your time and workload independently? Are you a self-starter with the diligence to work and hit deadlines without the constant oversight of your manager? On the flip side, are you able to create boundaries between life and work, even with having a home office, so that you lower your risk of burnout?

2. Understand your audience

  • Find out if the company has a flexible work policy. Some companies do, but many do not have an established policy and treat these requests on a case by case basis. If you will be a first fully remote person for your company or function, you will need to be even more prepared to make your case.
  • Identify your decision makers and engage with them to understand the barriers to them saying yes. This could be just your direct manager, the most senior person in your function, or also HR. Getting their perspective is the most important step toward crafting a proposal to get to yes.
    Identify your advocates. Approach colleagues who can speak to your manager on your behalf on your work product and work ethic to reinforce why your remote work proposal should be accepted.

3. Have a plan to make virtual feel seamless

Now that you understand the concerns the decision makers have, layout your plan for how you will do your work effectively and stay connected to your manager, your senior leaders, and your teams. This includes areas like:

  • Setting performance objectives with your manager and direct reports.
  • Discussing communication norms and availability expectations (especially if you will be in a different time zone).
  • Recommending a plan and travel budget for a cadence of in-person connections to build relationships and trust.
  • Demonstrating your proficiency with the technology tools needed for virtual communication and collaboration.
  • Agreeing to a structured feedback loop so that you can learn and quickly and course correct. I recommend doing an online survey with your key stakeholders after three months of working remotely.
  • Laying out your plan for a disruption-free home office or co-working space.

4. Don’t give up at the first “No”

  • Reframe it as a time-bound test or pilot. For example, ask to work remotely around an upcoming holiday when less high-profile work is happening. Or ask to work from home one day a week for a month. This will allow you to try out your remote work plan and show your manager how you will stay connected.
  • Timing is everything with this type of request. If your manager is not an advocate for remote work, are there another managers that might be? Look for other roles in the company that might be more open to being remote. And, in the future, there could be corporate changes that will open up a new window to ask again.

“Sacha gave me one-on-one coaching to develop a solid plan that influenced my senior leaders to allow me to be one of the first fully remote marketers for my company.”

Christine Parker
Senior Associate Brand Manager

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Join the others we’ve helped with developing a personalized plan to get to “Yes.”


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