First figure out your company’s stand. Most organisations are already working out flexible post-pandemic work options. “About 60% of people who worked in offices can’t wait to return to the old routine and networks,” says PD (name withheld on request), who heads HR regionally for a multinational and is responsible for 300 employees. If you want to buck that trend, play it carefully.

Find the right person to approach. “This is not an issue to take directly to human resources but to your immediate supervisor or team leader first,” says PD. “It’s a business need. Your company will treat it as such, and so should you.”

Practise your pitch. People’s reasons for wanting to work from home will vary — fear of contracting the virus, better work-life balance, fewer distractions, having to care for a loved one, time and money saved on the commute. Don’t expect employers to guess what yours is. Also, articulate what remote working means for you: Is it every day but just until the end of your child’s school year? Until the end of a project? Just two days a week, with the rest spent in the office? Just Tuesdays, when you’re visiting clients anyway? “A number-based request is easier to negotiate than a binary yes-or-no query,” PD says.  

Don’t involve colleagues. Marshalling a group will make it seem like an ambush (or worse, a revolt), could put your supervisor on the spot, and possibly result in a blanket refusal and lingering sourness. “Other colleagues may want the same thing, but for different reasons, or not want it at all. Let that be for the organisation to work out,” says PD. As for time with your boss one-on-one and let them know in advance what you want to discuss, giving them time to prepare too.

Couch it as a mutual benefit. Present it as an opportunity for you and the company, rather than a favour to you. Offer examples of how your switch could be better for the team, for clients, for a project and for the company.

Be ready with a plan. Suggest a trial period with a review at the end, which promises transparency and results in exchange for what you want. “Be clear on how you’ll stay accountable to your boss and your team day-to-day,” PD says.

Offer a contingency. This is a conversation, not a speech. Hear your boss out, ask questions. If it’s not going well, acknowledging that it’s new territory for you and for the company builds trust better.

Consider other cues. PD knows of an employee whose tech company was so invested in their staff working remotely, they gave each member a budget to buy a good office chair. How much your company is already doing for its workers is a good indicator of how it will likely respond to your request. Should it be denied, don’t renegotiate immediately. No one wants to keep fighting the same battle.