Last Updated on

How to ask your boss to work from home is tricky. Right now, there is an opening to engage your boss in a more realistic conversation about working from home. It is easy to argue that we are at home during a crisis and trying to work, but this is also an opportunity.

The work at home discuss has taken an interesting turn as there are three main opinions:

1. Those who absolutely hate working from home. Working at an office is a break from home life and gives the opportunity for adult conversation.

2. People who love working from home and want nothing to do with commuting or office politics.

3. Workers who want a combination of office and home office days that allows more flexibility for a better work-life balance.

Social distancing has given office workers the ability to try out working from home. So, if your goal has always been to work at home, this is your time. Make sure you are taking the following steps to prepare to ask to work from home permanently or at least more frequently.

picture of woman holding mug with caption work life balance: how to ask to work from home after social distancing ends
  • Pinterest
  • Twitter

Set the Groundwork

The first major step before asking to work from home is to set the groundwork. It is incredibly important to show your ability to manage yourself at home.

Remember a primary reason why companies have traditionally not allowed people to work from home is TRUST.

You need to gain the trust of your boss during this time of social distancing.

What does this mean?

1. Be Incredibly Professional

Don’t become a negative distraction for your boss. This is not the time to fall for your co-worker goading you into an argument where your boss needs to be the mediator.

It is not the time to complain about other workers. Your boss is also stressed out and doesn’t want the distraction.

Show that you are mature and are incredibly professional. This is the time to make sure you dress appropriately for video conferencing and remember you are on video conferencing. The viral video of the woman forgetting she is on a video conference and using the bathroom is not okay!

Make sure that distracts are addressed during phone calls and conferences. Everyone is being polite about the difficulties of working at home, but hearing kids in the background or dogs barking is just annoying.

Use proper phone and communication etiquette every time.

Be on time for meeting. Better yet, be early and prepared for meeting.

There can be no slipups in showing that you can communication properly without constant management supervision.

2. Know How to Use Technology

Don’t be that person who is always having technical problems. At this point, there are no excuses for not understanding how to video conference or for not understanding your company’s computer programs.

Constantly calling the tech hotline is a good reason for why you are not ready to work from home.

Keep your online calendar current for all to see.

3. Be Obnoxiously Available, Responsive and Flexible

This goes without saying, but you need to be available.

Try not to let phone calls go to voicemail during working hours. Don’t be that person who never answers the phone.

Respond to emails and phone messages quickly. The faster the response the better, but never more than 24 hours.

Don’t be rigid with your hours. Having the benefit of working at home does require flexibility.

Prepare for the Ask

1. Tracking Goals and Objectives

Remember a key question will be why should you be allowed to work from home?

Data will help answer that question. There needs to be a tangible measurement that you are meeting your customers’ needs better from home.

Use metrics to your advantage to highlight your accomplishments.

It is important to track all accomplishments to prepare for the ask. If you are struggling to stay productive at home, it is important to address those issues now.

Pushing to work from home will not be successful if you are not as or more productive at home versus the office.

2. Providing Frequent Updates to Your Boss

Communication is critical. A big reason why remote work can be discouraged is the need to key an eye on people. Some members of management make a career of babysitting and micromanaging people.

If your boss doesn’t know what you are doing, the assumption is you are goofing off.

Make sure you are reaching out daily and/or weekly to decisionmakers. Decisionmakers are not limited to your boss.

Progress reports are an effective tool for communication. These reports help document your productivity and highlight key goals and objectives. It is hard to argue against facts. This is also a good way to start promoting yourself and the value of working from home.

3. Take on Additional Tasks

Again, the goal is to show how efficient and more productive you are when you work at home. The additional tasks don’t need to be world changing, but should add value.

Think of tasks that would make working remote easier and more efficient,

make your boss’s job easier,

improve productivity within your team,

make coworkers or employees’ jobs easier, or

take a free online class and discuss potential application for the team.

There are plenty of tasks or projects that probably don’t require a huge time commitment, but would add value to the organization. Take the time to brainstorm ideas.

4. Career Plan

Everyone should have a career plan. Take this time to develop a 10-20 year career plan that can be shared with your boss. This career plan needs to clearly demonstrate that working from home won’t impact your future contributions to the company.

back of woman with sweater and header be smart and prepared: after social distancing ends, how to ask to work at home
  • Pinterest
  • Twitter

Create the Proposal

The document needs to reflect how your company communications. If your company communicated via PowerPoint presentations, make a PowerPoint presentation.

The proposal needs to clearly answer the question: how do you bring more value to the company by working at home?

Frequency of working at home needs to be addressed. Are you going to work every day at home or a few days a week?

This proposal must tie to your career plan as the company is investing in you for the long-term.

Facts matter and need to support your case. This is where your progress on goals and objectives should be highlighted.

Use business buzzwords like productivity, value creation, efficiency, and cost control.

Brainstorm a list of questions that will likely be asked and address those questions in the proposal where relevant.

Remember your proposal is an ask and not a mandate. You need to bring a solution to a problem.

Better yet, if the proposal can make your boss look good, it will likely be better received by your boss. Remember your audience. Your boss is thinking “what’s in it for me?” Make sure to answer that question!

The Big Ask to Work from Home

Timing is going to be everything for the big ask. You need to read the corporate environment and your boss to determine the best timing.

Set up a meeting with your boss to review your proposal. This is a serious ask, so make the setting a formal meeting and not just a side conversation.

Prepare yourself for the conversation. During preparation, review answers to potential questions.

Remember to listen to feedback and take notes.

Don’t expect a yes right away and expect to be asked to do more work on your proposal. This is a classic stall technique while the boss is trying to figure out what to do with the proposal.

Promptly, respond back to questions asked and additional work requested.

Follow up after a couple of weeks with your boss. There are many bosses who will hope that you will just drop the request if your boss does nothing as a response.

Be prepared to execute your plan quickly. Once you get the yes, don’t waste time or everyone will think you were not serious.

Remember to say “thank you” and keep the commitments in your proposal.

Know your next steps. After about a month, your boss needs to commit to allowing you to work from home. If that commitment is not there, recognize that the answer is probably “no”. There is no reason to burn bridges.

Final Thoughts

Below are two articles that expand on the theme of career advice tips. Many of these tips can be used in addition to the recommendations above to impress your boss and get what you want at work.

Getting the answer yes to asking to work from home takes a lot of preparation. Feel confident that the steps provided will give you a fighting chance. There are some companies where working from home is never going to be in their DNA. For many companies, their eyes are being open to the possibility.

Take the risk, be brave and ask to work from home.

Good Luck,

WhipperSnapper Finance

Read On

How to get promoted at work with career work advice tips #careeradvice
  • Pinterest
  • Twitter
Rose faded background with words: How to impress your boss and stand out is about helping your boss succeed and getting your next promotion. #careeradvicetips #impressboss #promotion | via @whippersnapperfinance
  • Pinterest
  • Twitter
0 0 vote
Article Rating
Would love your thoughts, please comment.x


Free Financial Challenge Workbook for signing up!

You have Successfully Subscribed!

Pin It on Pinterest

Share This