Convincing Your Boss to Let You Work From Home

Convincing Your Boss to Let You Work from Home -

by Chris Durst    04/21/2016  – Parts excerpted from “Work at Home Now,” a book co-authored by Christine Durst and Michael Haaren.

If you’re already employed doing something you love – but you’d also love to eliminate or reduce your commute – then this information is for you.

Before reading on, it’s important to first remember that telework is a management option rather than an employee right or “benefit,” and is justified by the advantages it offers the company – not the employee.

In other words, your employer’s first question is likely to be “What’s in it for the company?”

With that in mind, your biggest mistake could be going to your boss and simply stating, “Can I work from home? It would be so much better for ME because __________ (fill in the blank).”

On the flip-side, your best shot at a “YES” is to show your boss how letting you work from home will make him/her look like a hero to his/her boss.


Have a plan, not a request
In most cases, if you have a decent boss, they’ll probably be sympathetic to your reasons for wanting to work from home, but the harsh truth is that your child-care issues (or an aging parent, an outrageous commute, unreliable transportation, etc.) are not his or her problem. Further, unless your boss also owns the company, s/he has to make decisions that the upper management will approve of. In other words, the company has a goal (usually money-driven) in mind and “helping Employee X spend more time with her children” usually isn’t on it.

That’s the harsh reality – companies can’t make decisions based on “feelings” instead of earnings. If they did, profits may suffer, and jobs may be put at risk – including yours.

So let’s explore how you can wow the boss with a company-oriented plan, instead of a self-oriented request.


Creating a Winning Telework Proposal


Here, we’ll walk you through a step-by-step process for creating a winning proposal. Those steps will include:

1.    Drafting an attention-grabbing opening statement
2.    Outlining the benefits to the company
3.    Breaking down your daily tasks and commitments
4.    Proposing a schedule and highlighting your flexibility
5.    Suggesting methods for quantifying your productivity
6.    Reminding your boss what a valuable asset you are to the company
7.    Describing your home-based workspace and equipment


1. Drafting an attention-grabbing opening statement
Length: 1-3 paragraphs

Open your proposal with a short statement that will make your boss want to read more. (Though this section will appear first, you’ll want to write it last, so you can weave in supporting statistics and other data you find in your research.)


2. Outlining the benefits to the company
Length: 2 pages

We usually refer to this as the “What’s in it for them” section of the proposal (“them” being your employer, of course). Here, you’ll show in detail how you’ve considered a telework arrangement from the employer’s viewpoint, and you’ll lay out the compelling reasons why it would directly benefit the company.
This is often the “make or break” part of a proposal. Be prepared to roll up your sleeves and spend plenty of time searching for facts and statistics that will “hit home,” so to speak, with your boss.

3. Breaking down your daily tasks and commitments Length: 2-3 pages, depending on your job descriptionThis section of your proposal is the “reality check” – an assessment of whether your job can actually be done from home. To show your boss you’ve given this proposal due thought, you’ll need to analyze every aspect of your job – the tasks you manage, who you interact with, what resources you use, how you deliver your work, etc. – and explain which duties you can do from home, and how. 4. Proposing a schedule and highlighting your flexibility Length: 2-3 paragraphsThe key to an acceptable telework schedule (“acceptable” as defined primarily by management, of course) is to transition into the arrangement conservatively, at a pace your boss can be comfortable with. (If you perform well, the schedule you yourself would prefer will hopefully follow.) While aggressive schedules are easy for management to refuse, a well-planned “trial period” might seem not only eminently reasonable, but even an exciting experiment – one that could spearhead a larger telework program within the company. 5. Suggesting methods for quantifying your productivity Length: 1 pageIt’s important to remember that most managers have never supervised a remote workforce, and you may be asking yours to take a step outside his or her managerial comfort zone. Regardless, managers often note (or by stonewalling even minimal telework initiatives, betray) their concern that employees will be unproductive if unwatched. In this section of your proposal, you can ease any such concerns by suggesting ways in which your productivity can be measured. 6. Reminding your boss what a valuable asset you are to the company Length: 1 pageMaking a case for “you” as a viable work-at-home candidate is an important step in sealing your telework deal. (Indeed, it helps to approach the entire campaign as if you were applying for a job.) After all, it would be a pity to persuade the boss to embrace the idea of telework – but not for you! Use this section of your proposal to “strut your stuff,” and remind your boss of all the wonderful attributes and accomplishments that make you the ideal candidate for off-site work. 7. Describing your home-based workspace and equipment Length: 1 pageIt may sound mundane, but it’s important to “paint a picture” of your work environment for your boss. This will not only help him or her visualize you working there, but also show that the space is professional-grade and free of distractions. Ideally, your proposal will include photographs of your home-based work space, but you can make do with a diagram and a written description.


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