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When Do I Bring Up That I Want to Work From Home? 5 Tips for Having THAT Conversation With Your Boss

August 5th, 2021

A lot of employees have gotten a taste of what it’s like to work from home. For some people, it’s just not their cup of tea and they would prefer to work in the office. But there are some who have become accustomed to it and want to continue to work from home post-COVID. There are also other people who still want to give it a try because it would better suit their lifestyle.

work from home conversation

If you want to continue to work from home, you will need to have a conversation with your boss about the possibility. Their stance on the subject can vary based on their personal preferences, company policy, and other considerations. But if you personally want to work from home, you need to bring it up. You also need to be prepared to make a good argument for why you should be able to work remotely.

Here are some tips for having a conversation with your boss:


1. Be real about the possibility

It is important to be realistic about your work situation. Does it make sense for someone in your role to work from home? Are there potential issues that could arise? Remember that your desire to work from home may not be in alignment with company objectives. Perhaps a hybrid solution is more realistic. Be open to a number of work arrangements.

2. Do your research before stating your case to work remotely

Do some research and find out if your company has a formal policy about working from home. Does the company have a particular feeling about this type of work arrangement? Are other people already working from home? If no one works from home and your company is against it, there may be no sense in making a case.

3. Book a meeting to discuss it with your boss

Requesting to work from home is not a casual conversation. You need to set aside some time to formally speak with your boss about it. Let them know what you want to speak about so they will have some time to prepare for the conversation.

4. Be ready to state your case

If you want to work from home, you will need to state your case as to why it is viable for you. Speak about why you are a good candidate to work from home. If you have a proposed schedule and plan for how to communicate with the office, make sure to present it to your boss. Be as detailed as possible. You need to show you have given this some serious thought.

5. Identify and address concerns your boss many have

Be ready to address counter-arguments and resistance. Expect your boss to raise concerns about how you are going to manage your workload and how it will potentially impact other people you work with regularly. Put yourself in your boss’s position and be receptive to their concerns and feedback.

Be willing to compromise and come to an agreement that works for all parties.

Read More About Remote Work on Our Recruiting Blog

5 Legitimate Reasons Employees Should Continue to Work From Home in 2021

10 Legit Work From Home Jobs for Parents & Caregivers

The Home or the Office? 4 Hybrid Workplace Solutions for 2021


IQ PARTNERS is an Executive Search & Recruitment firm supporting clients across the country. We help companies hire better, hire less & retain more. We have specialist teams of recruiters in Executive Search / Board & C-Suite, Technology, Media, Digital & Marketing, Accounting & Finance, Financial Services & Insurance, Cannabis, Startup, Data Science, Consumer, eCommerce & Retail, Operations & HR, Manufacturing, Supply Chain & Engineering, Legal & Professional Services, Pharmaceutical & Life Sciences, Non-Profit & Sustainability, and Sales. Click here to view current job openings and to register with us.

Kourtney Savona

Kourtney Savona

Kourtney is a top-performing recruiter focused on helping clients hire the best sales and operations candidates in the market. With 6+ years of experience, she specializes in recruiting Rockstar across many different industries in North America. Prior to becoming a recruiter, Kourtney started a career in sales. From door-to-door, hustling in the winters to becoming a top-performing sales representative for one of the largest telecom companies in Canada. Kourtney knows what separates a good salesperson from a great one. She has the ability to source exceptional candidates for complex roles using innovative, and creative out-of-the-box thinking. Kourtney earned a Bachelor’s Degree of Business Administration with a concentration in Entrepreneurship with Honors from the Goodman School of Business from Brock University.

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