How to ask your boss to work from home after the pandemic?

Can you ask your boss to work from home?

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Have you been enjoying working from home for the last year and a half but your company started talking about going back to the office? Or maybe you’re already back and dreading the daily commute?

Asking your boss to continue working from home can be a scary idea (I’ve been there!), but if you don’t ask – you won’t get it! You can always ask the question – there are really no bad sides to it – and even if you receive a negative answer, you won’t keep thinking ‘What if?’.

Plan it

This is the most crucial thing to do before asking your boss to work from home after the official return to the office. Ask yourself the below questions before you get into the process:

  • Is my boss generally ok with working from home? – some people sill have the outdated idea that if you are working from home, you are not working at all. Try to find out discreetly what your boss’ opinion is and if they are generally open to let people have more freedom.
  • Is my boss the decision maker? – in many cases, especially in big corporations, your boss or even your boss’ boss might not be able to make this decision. It may be down to HR, country manager or someone else setting up the rules and deciding the faith of employees.
  • What are the benefits? – list the benefits for yourself, your boss and the business. Exhaust the list as much as you can. You don’t have to use all the points when you actually request the change to your working arrangement, but it’s good to be prepared for any pushback.
  • What could be the objections? – prepare a list of objections that you expect to receive and address your solutions to them. Presenting the objections upfront by yourself, shows that you really thought this through and it will support your case.
  • How will you report your performance? – in the last year and a half we all have had a challenging time, adjusting to the work from home and having to learn to communicate in different ways to make sure our work is still recognised and appreciated. Think how you could enrich this going forward. What would be your KPIs? Milestones in the near future? How will you report your success to your boss?
  • What would be the arrangement? – suggest a number of days when you could come to the office if absolutely necessary (for example once or twice a month). You can also suggest a trial basis to ease the business into the idea.

Start introducing the idea

Once you have exhausted the above topics, you can start introducing the idea to your boss. Start mentioning during your catch-ups that you enjoy working from home, you can even mention that you would love to continue doing so, but just throw it into the conversation and don’t expect any answer. You can mention that your stakeholders are planning to continue video meetings or that it’s easier to focus in the quiet environment of your own home.

This is not a must-do step, but it is the way I like to approach it. This gives me a chance to ease my boss into thinking about it and getting them on board in a gentle way. It is also a great opportunity to spot if they are keen on the idea or are a bit hesitant.

When I requested to continue work from home the last time this is exactly what I did. I slowly introduced the idea, poked here and there to see how my boss is reacting. I also took his personal experiences with WFH to show that I understand the challenges and that we are on the same page in the end.

Once I saw that my boss is open to the idea (he was not at the beginning!) I moved on to the next step.

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Ask during a catch up

A good option before officially asking to work from home is to advise your boss that you will be making the request. If your work environment is a bit more formal, you can send an official email, but if it is more relaxed you can just say during your regular catch up ‘Hey, X, I would like to discuss working from home after we return to the office during our next catch up. Let’s have a chat if we could make this work’.

If you were introducing this idea slowly, your boss will not be surprised that you want to officially ask for this and it might be easier to move this forward.

Before the next meeting, make sure you read through the list that you made during the planning phase.

  • Pick 3 benefits to the company (and your boss if there is a good one),
  • bring up 1-2 objections and show the solutions for them,
  • give a high level idea of reporting your performance
  • and suggest the working schedule – here a little tip. If you are ok with working few times a month from the office, suggest only once or completely remote. You can then get to the desired outcome during the negotiations. I wouldn’t start with giving up all your leverage and suggesting more days in the office, as it is quite likely your company will want to increase the number of days you suggest.

Follow up with an official email

After the catch-up and the conversation with your boss – even if they are negative about the idea or even say no initially, make sure that you follow up with an official email. Regardless of if your work environment is official or relaxed, this is a good practice as helps you document what was said and gives your boss a tool – they can forward your email to the decision-makers without having to come out with their own explanation, why should you work from home.

Keep the email simple and repeat the same key messages that you mentioned in your conversation. If your boss has raised any objections, make sure that you address them here as well.

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What if they say no?

That’s a risk, but what if they say yes? There is nothing wrong with asking questions.

Just remember that negative answer doesn’t mean that you can’t negotiate well or that you didn’t prepare well enough. Very often these decisions have nothing to do with your ‘pitch’, but more with internal policies.

If it’s still a remote role that you want, but the company said no? There is plenty remote or more flexible roles right now on the market, as companies realise that this is the way to recruit the best talent. Don’t be afraid to reach out outside of your company and see what’s available!

Have you asked your boss to work from home yet?

If this is the type of work conditions you want – make sure you follow the steps and actually ask the question!

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Let me know in the comments if you have done it, how it felt and if you got your request approved!

Rooting for you!

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