Now, I usually don’t do this fluffy stuff.
As you’ll soon see, I like to get straight to the point and get you wins fast and as often as possible.
But before we dive into it, let’s take a brief moment and start with WHY.
Why are you here? What’s the goal of all this?
Obviously, to convince your boss to let you work from home. But let’s take it a step further.
Whether it be to ask to work from home to avoid a dreaded commute, spend more time with family, or even travel the world, the real goal here is to be FREE.
And to do whatever makes you happy when you are free.
That’s WHY you are here.
And HOW do we get you to be free? By walking you step-by-step through the frameworks and scripts to do just that.
More specifically, this post will teach you all the SECRETS of:
- How to Ask Your Boss to Work From Home – This includes playing to egos, directly asking, leveraging your time at the company, etc.
- The Hidden Benefits of Working From Home – This includes employer benefits, other work from home companies, employee empowerment, etc.
- How to Overcome Your Boss’s Fears and Objections of You Working From Home – This includes addressing no work from home policy, measuring work from home productivity/results, data security/privacy, etc.
- Putting Together a Presentation and Presenting It to Your Boss – This includes setting up the meeting, having & ending the meeting, and following up from the meeting.
But before we dive in, I need you to promise me one thing.
Are you ready?
Share with one person that you are going to ask to work from home.
That’s it. Nothing more.
Email, call, text, post on social media, just tell someone that’s what you want, and you have the guide to do it.
And if they ask WHY… Well, you should already have your answer.
Heck, you can even email me if you’d like (email@example.com) if you need someone to commit to.
And yes, I will reply!
Now that we are committed to ourselves and have shared with someone else, it’s time to dive in.
Company First Approach
How to Ask Your Boss to Work From Home
Overcoming Fears & Objections
Companies With Work From Home Policies
How Working From Home Will Actually Work
Finalizing The Presentation
The Meeting With Your Boss
The Outcome of Your Meeting
Company First Approach
So you may be wondering why I’m qualified to talk about this topic.
Well if so, then I’m happy to share that after multiple failed attempts, I was able to convince my boss to let me work from home with this exact proven method.
Additionally, I want to make sure you are fully equipped for success here so I am also giving you a free copy of the book, “How To Convince Your Boss To Let You Work From Home”.
The free book will go into 10x more detail than this post, with even more statistics and examples to back it up. Again it’s free!
Now that you know where you can access those free resources, let’s get to it!
Make no doubt about it…
The best way to get approval to work from home is by having a 1:1 conversation with your boss that is guided with a powerpoint / Google Slide presentation.
Everything we are going to go through here is to help you set up and have that conversation with your boss, along with creating your presentation.
Before we discuss those topics, it’s critical to equip you with the ideal mindset when approaching to request to work from home.
And that mindset is to show that working from home will help not only you grow, but the company also.
This is what is known as a Company First Approach.
Furthermore, when it comes to asking/convincing your boss or company to let you work from home, I’ve found the best way to get approval is by playing into their ego.
We are going to stroke their ego by showing that you:
- Love your job
- You love working for the company
- You have a plan to become a better employee (your presentation)
Ok, now let’s walk through the elements of the conversation and presentation.
How to Ask Your Boss to Work From Home
It’s important to be transparent.
Which means both in the conversation and presentation make it clear that you are asking to work from home.
So how does this fit into our presentation?
This should be your 3rd slide.
1st Slide = Title, 2nd Slide = Agenda/Outline
Overview of Your Time at the Company
- How long have you been there?
- What have you been able to accomplish so far?
Why You Enjoy Working for the Company and What Your Future There Looks Like
- How will working from home improve your future at the company?
- E.g., Avoid work office distractions and to be more deep-work focused and deliver high-quality work.
Skills/Knowledge You Want to Gain to Make You a Better Employee
- How will working from home potentially help you get there?
- E.g., Save time commuting to use for additional learning and extra work time.
It may not be obvious, but in this third slide, we are creating a vision/future in which you work from home.
Furthermore, we will be directly stating that we believe that working from home will help not only you grow, but the company also. Again, this is our “company first approach”.
Powerful phrases to tell your boss/company that you want to work from home are:
- I believe I will positively impact the company by working from home because [insert reason].
- I’m confident that allowing me to work from home will help the company do [insert reason].
At this point, your boss probably has a million questions. Rightfully so, it’s a big ask and a big decision to be made.
If they have already started asking, don’t stress. This is a good sign!
Up Next: All the reasons why it’s beneficial for your company (company first approach) to have you work from home.
Company Benefits of You Working From Home
In a negotiation, everyone wants to feel like they won. So that’s exactly what we are going to do.
We will make your boss feel like they’ve “won” by telling them all the benefits the company will receive when you’re working from home.
In other words, we will give them several reasons that your boss can use to rationalize to themselves and others (if needed) on how this is a smart decision for the company.
But in reality, we both know who the real winner will be from this, YOU!
Okay, so what are these employer benefits?
Saving Time & Money
By allowing employees to work from home, companies can save money on:
- Commuting costs, work vehicles, mileage reimbursement, etc.
- Office space, work equipment, etc.
- Company entertainment (events, meals/catering/food, etc.)
- Paying for sick days
- Health benefits and phone plans
- And much more…
A study compiled by Global Workplace Analytics estimates that companies save $100,000 per employee they don’t have to relocate.
Furthermore, the study states that the average real estate savings with full-time work from home employees are $10,000 per employee per year.
Now that’s a lot of money your company could be saving, even for just one employee. Just think, that’s $10,000 savings is an absolute minimum, imagine if everyone was able to work from home.
Subsequently, not having to plan or record all these extra costs saves a lot of employee time. For example, an accountant recording asset depreciation, HR finding a catering service, or IT setting up an office workspace.
From another time-saving viewpoint, who enjoys driving in bumper-to-bumper traffic? You’re right, NO one.
Instead of getting ready to go to and from the office and making the actual commute, the extra time can be spent doing something more meaningful.
If you want to stroke your boss’s ego, it’s best to say that this extra time will be used to work more.
Otherwise, you can go with a healthier work/life balance as an alternative (i.e., spend time with family, new hobbies/skills, etc.).
Increased Employee Productivity
Companies with work from home policies on-average find their employees take less sick days.
More specifically, there are 63% fewer unscheduled absences for work from home employees, compared to in-office employees.
Taking it a step further, work from home employees typically continue to work even when they’re sick (without infecting others). They are more likely to return more quickly to work after surgery or a medical issue than in-office employees.
Another big productivity drainer is office distractions.
Whether it be workplace gossip/politics, unnecessary meetings, or your desk neighbor dropping in to ask a question because they are bored or distracted, these distractions are practically inevitable.
Even more so, they can ruin your focus, causing you to be unproductive.
In contrast, employees who work from home typically choose a distraction-free work environment so they can produce deep, focused, high-quality work.
Improved Employee Recruitment & Retention
According to The Wall Street Journal, “It costs upwards of twice an employee’s salary to find and train a replacement. And churn can damage morale among remaining employees.”
What this really means is: It’s expensive to hire and train new employees.
Even firing employees can be expensive, but that’s another story.
Being able to retain top talent decreases company recruitment and turnover costs. And one tactic for retaining top talent and attracting top talent is offering employees the ability to work from home.
Taking it a step further, this perk can also be leveraged in favor of a company as a hiring trade-off for monetary compensation.
In other words, it’s perceived that the majority of job candidates will accept a lower salary for the ability to work from home because of the comparatively lower supply of work from home jobs.
When a company allows its employees to work from anywhere, they can also hire from anywhere.
For example, a Chicago-based company isn’t limited to only Chicago for hiring. They don’t have to convince anyone to move there and can hire from the estimated 4.8 billion working-age talent pool.
Work from home job boards make it easy for companies to attract and hire top talent.
Touching more on retention, by offering employees the freedom and flexibility to work from home, this increases trust and fosters a sense of loyalty between employers and employees.
Diving a bit deeper, this psychological benefit is known as reciprocity. When companies give their employees the ability to work from home (on their own schedule), it conveys trust between everyone.
By nature, employees are likely to reciprocate this trust by performing high-quality work and staying at their job.And lastly, according to Global Work Place Analytics, “95% of employers say telework has a high impact on employee retention.”
The bottom line?
Offering employees the ability to work from home increases employee retention and recruitment.
More Employee Empowerment
Let me take a wild guess; at one point in your career, you’ve had a boss who complained about everything.
Or, even worse, wouldn’t let you make any decisions or asked for constant project status updates.
Aka micro-managed you.
In one way or another, we’ve all been micro-managed before, and it’s NOT FUN.
But by working from home, it forces your company to let you be independent and self-directed — two skills companies want in their team.
Which usually results in a decrease in micro-management and an increase in autonomy in the long-run. This will be more evident once you are working from home.
Empowering employees also improves their accountability, communication effort, and motivation.
This is just the tipping point of employee empowerment. Let’s go deeper.
One of the best ways to empower employees is to reward them based on results, not just for showing up to the office.
Working from home helps accelerate this results-driven environment for both the company and employee.
Employees who feel in control of their work schedule typically enjoy their job.
By allowing employees to work from home (empowering them), companies build a team of employees who feel personally responsible for the company’s success.
Better Work-Life Balance
It’s no secret. Poor work-life balance negatively impacts employees’ health and happiness.
Less control over this balance can lead to more stress and turnover. And that’s not good for any company, mainly because it can make others stressed and leave.
When comparing in-office employees to work from home employees, work from home employees report a better work-life balance as the top reason they work from home.
Having autonomy and flexibility over work and personal schedules allows employees to manage their responsibilities effectively and avoid getting burned out.
Adding Company Benefits to Your Presentation
Now that you are an expert in understanding the benefits your company will receive when you are working from home, it’s time to put your powerful knowledge into action.
More specifically, adding bullet points from the sub-sections above into your presentation. This should be your 4th slide, right after your overview slide.
From experience, I’d recommend taking the chapter sub-sections and putting them as the bullet points. Then adding notes to speak about in the “Speaker Notes” section (at the bottom) to review when you’re practicing.
And as you probably already know, the fundamental presentation rules of thumb, don’t include a lot of information on the slides (3 – 5 bullet points) and don’t only read word-for-word off the slides.
Pro-Tip: List what you believe will be the most important company benefits first (in order).
BOOM! You have just given your boss countless company benefits as to why you should be allowed to work from home.
Up Next: Overcoming common fears and objections that may be holding your boss back from letting you work from home.
PS: If you need a few more points to push your boss over the edge, see below.
- How Companies Benefit When Employees Work Remotely – Harvard Business School
- Latest Work-At-Home/Telecommuting/Mobile Work/Remote Work Statistics – Global Workplace Analytics
- Advantages of WFM Strategies For Companies – Global Workplace Analytics
- Pros and Cons of Telecommunication Work – Global Workplace Analytics
Overcoming Your Boss’s Fears & Objections
It might be hard to believe but it’s normal to fear change.
Fear is primarily the culprit that stops people from taking action and achieving their desires.
And that’s why fear is the #1 reason that stops bosses/companies from letting employees work from home.
Essentially, they say no based out of fear.
So that leaves us with, how do we help our boss/company overcome these fears?
The best strategy I’ve found to be successful is to bring up these fears before they are realized and share thoughtful, pre-planned solutions.
Thinking proactively about your boss’s biggest fears and how to solve them is one of the most critical parts of your conversation and presentation.
It shows you are serious about working from home.
Ok, now let’s discuss some of the most common objections and how to overcome them.
No Work From Home Policy
Due to COVID, the majority of companies, at some point, have been forced to have their employees work from home.
If this was you, great!
Use this experience to show your boss you can work from home again.
If your company did not allow work from home during COVID or before, don’t panic.
Instead, ask yourself, does anyone at your company right now work from home? Or has anyone in the past?
If someone has already gained approval, they will be your best advocate.
Talk to them and leverage their success as yours.
If no one has worked from home or there is no company policy, you are still okay.
We have two options to solve this:
- Share successful companies in your industry that have work from home policies.
- Propose that you working from home will be a “trial run” for the company, and you will be a “guinea pig” for others.
This second tactic will help your boss rationalize to others who might ask why you are allowed to work from home and not them.
The best way to reduce in-office tasks is to:
- Make a bullet-point list of what you are responsible for at your job
- Split into in-office responsibilities and work from home ones
- Write down alternative solutions to these tasks
A few ways to think about potential solutions are:
- Can someone else temporarily take over that responsibility?
- Can I delegate that responsibility to someone else?
- Or perhaps trade that responsibility with someone or something else?
There’s a high probability that almost all in-office responsibilities can be solved.
And if worst comes to worst, an alternative solution is to ask your boss to remove it from your plate altogether.
No System to Measure Productivity
It’s no secret: What gets measured, gets managed.
Productivity is often measured to ensure that employees are working.
Plus, it’s another way for companies to evaluate employees against their responsibilities and each other objectively.
Software tools are commonly used to measure productivity and time.
Do any of these tools sound familiar to you?
- Project Management (Asana, Basecamp, Trello, etc.)
- CRMs (Salesforce, Hubspot, etc.)
- Work-space Communication (Slack, Microsoft Teams, etc.)
- Time-tracking (Toggl, Clockify, etc.)
If yes, that’s great! You might already have a system in place to measure your work.
If no, DO NOT worry! There are several free and easy solutions to use.
The most popular options are:
- Asana: Add all your tasks, due dates, and mark complete once done. Share with your boss so they can monitor your progress.
- Note: You can also take screenshots of work completed within two time periods to compare in-person versus remote.
- Toggl: A simple time tracker with powerful reports that tracks work time across all devices.
- Status Hero: Replace costly stand-up and status meetings with brief, daily check-ins.
Note: It’s helpful to have a baseline before asking to work from home. This way, you can compare previous work periods (e.g., working at the office versus home).
So, if you don’t have a baseline, it’s best to start using one of the three tools mentioned above (recommend Toggl).
Having a system in place that can measure your productivity gives your boss an effective solution to manage you when you are working from home. Ultimately, helping overcome their fear of how to manage you.
Fairness to Other Employees
The fear of fairness is quite common, and it can sometimes make for awkward and frustrating situations.
It may be hard to believe, but bosses/companies WORRY about what other employees might think if you’re working from home and they aren’t.
People tend to care more about what others are doing, rather than minding their own business. Especially if there isn’t already a work from home policy in place.
To overcome this fear, we are going to arm your boss with the viewpoint that you working from home is a “trial run” for others in the future who also deserve this opportunity.
Essentially you are going to be a guinea pig in a small, controlled company experiment.
You and your boss will set success criteria to determine whether or not the trial run was successful. And whether or not to make it available for other team members.
It’s essential that you work with your boss to define success. This is where your productivity system comes into play.
One way to define a successful trial run is to compare productivity between two time periods (before & after). Or have a set list of what needs to be done while you work from home.
Note: More on this topic with expectation settings in Chapter 6 (How Working From Home Will Actually Work).
This primarily means having a secure connection and data storage.
Chances are you probably had or will have to use a Virtual Private Network (VPN).
There are many VPNs out there, and they are simple to use. The best one I’ve found is ExpressVPN.
ExpressVPN is a paid VPN ($13/mo), but there are many free VPNs too.
These file storage softwares are great for sharing and collaborating on and for using offline (without service/WiFi) and on the go with their mobile apps.
If there are any other security and privacy issues, it’s best to speak with an IT team member.
What about if you have in-person meetings with clients / external relationships?
If this relates to you, it’s essential to set expectations with them by having a separate conversation after getting approval to work from home from your boss.
Instead of the in-person meeting, it’s best to keep the meeting times and frequency the same, instead propose a virtual meeting.
The majority of the time, your client / external relationship will be excited for you and ask how you got approval to work from home.
Heck, they will probably be even a bit jealous and say they wish they could do the same. If they do, send them this post.
Anyways, the takeaway here is that you’ll only want to bring in your clients to this decision process when appropriate.
Legal, Tax & Visa Concerns
Ok, so a lot of people get hung up on this.
Am I going to have to pay foreign taxes? Or my company?
Disclaimer: To be clear, I’m not a lawyer nor an accountant, so I can’t give professional advice.
Although, here’s how I would think about it.
Think of a time when you took a phone call or wrote a work email from home or in another state or country, like going on vacation and bringing your laptop to do some work.
It’s essentially the same thing.
As long as you’re not going into another country and taking away work from a local, you should be fine.
Lastly, make sure you’re paying attention to tourist visa restrictions for countries you plan to travel to. That’s on you, not your company.
Time Zone Differences
If you plan to work from home and travel, then time zone differences might be a fear.
It may sound something to the tune of… “2 PM EST is what time in Lisbon, Portugal? Will you be online then?” or “Will you be working when we are working?”
The secret here to overcoming this fear is to set clear expectations with visual help.
More specifically, a time table of overlapping work hours.
I HIGHLY recommend using and bookmarking the tool Time Buddy – Clock & Time Zone Converter to help out with this.
Its carefully thought-out design lets you effortlessly compare multiple time zones at a glance, plan virtual phone calls / meetings, and view potential new travel location time zones.
Unexpected Work From Home Costs
Let’s be real. It’s almost always cheaper for a company to have you work from home rather than in an office if you think about it.
No office space or commuter costs, less cost on company events & meals, paying for less sick days, and office equipment. The average real estate savings from a work from home employee is about $10,000/employee/year. And the list goes on…
The fear of unexpected costs is best overcome with an offensive play that lists the cost savings of working from home.
Realistically the only friction point here might be the cost of work from home equipment.
A few common scenarios:
Scenario: You work on a desktop/laptop at the office and aren’t sure if you can bring it home.
- Solution 1: You may need to purchase a computer with your own money to use for work.
- Solution 2: Ask if it’s unreasonable to bring home the computer.
Recommendation: Laptops are more versatile. Don’t bring home a desktop if you are going to be frequently traveling.
In some cases, you may be able to get your company to purchase the computer/office equipment (desk, extra monitor, chair, etc.) for you and write it off as a business expense.
Note: This also applies to the software tools mentioned above (project management, VPNs, cloud sharing, etc.).
Other Work From Home Fears & Objections
Ok, before we move onto social proof, it’s important at the end of this point of the presentation to make sure to ask your boss:
“Do you have any other concerns that we have not addressed/solved yet?”
This will help your boss voice any other fears & objections they might have about you working from home.
Once they are done sharing, use the company first approach and discuss potential solutions for their concerns.
Even if you aren’t able to come up with a good answer on the spot, do not make one up.
Tell your boss that you will follow up on their concern soon after your meeting.
Remember, it’s all about talking through the fears and objections, listening to each other, and arriving at a solution, together.
Adding Fears & Objections to Your Presentation
Like company benefits, now that you are an expert at overcoming common fears and objections from your boss, we will add these new insights into your presentation.
Again, I’d recommend taking the chapter sub-sections and putting them as bullet points into your presentation (should be your 5th slide).
Then adding notes to speak about in the “Speaker Notes” section (at the bottom) to review when you’re practicing.
And don’t forget to list the bullet points in order of importance – most important at the top.
Woo-hoo! You made it through the most challenging part of the presentation.
Up Next: Time to supercharge your presentation by sharing and explaining how other successful companies allow their employees to work from home.
Companies With Work From Home Policies
It’s no surprise…
Several successful companies (both big and small) that allow employees to work from home have the research and results to back it up.
The BEST part?
You get to leverage their results as social proof to convince your boss to let you work from home.
Work From Home Companies
Here is a list of some of the top US companies that have work from home policies.
- Microsoft – “During COVID-19, Microsoft was one of the leaders that showed remote work to be successful and improve productivity.”
- Dell – “In 2016, 25% of Dell employees work from home either full-time or a few days a week. The company is aiming to double that share to 50% by 2020.”
- GitHub – “Over 60 percent of its workforce is outside of San Francisco HQ.”
- WordPress – “Everyone works from home, or more precisely, from wherever in the world they wish.”
- Cisco – “Almost 60% of our employees work from home, which has saved us over $200 million a year in travel alone, with our technology.”
- Galactic Fed – “We are a 100% remote company. No offices. No cubicles. No watercooler small talk.”
And many others that have allowed their teams to work from home:
- Johnson & Johnson
Ask yourself… Which companies in your industry allow employees to work from home?
If you didn’t see a company in your industry, don’t stress – here’s a list of the Top 100 Companies with Work From Home Jobs in 2020.
Many of these companies use the work from home “work perk” as a recruiting advantage over their competitors. Your company could also leverage this too.
Leveraging Social Proof
At this point, you may be thinking, “It’s great that all these other companies offer work from home policy, but how does this apply to me?”
The benefit to you is social proof. Pretty straightforward.
Showing your boss that lots of other successful companies (ideally ones in your industry) allow employees to work from home helps your boss understand that what you are asking for is reasonable.
Adding Social Proof To Your Presentation
Now, let’s take action and add this to our next slide (slide 6).
The best way to do this is to:
- Find companies in your industry with work from home policies (from the list or link above).
- Identify quotes that show company benefits from allowing their employees to work from home.
- Add these quotes (ideally two or three at most) and their company logos, along with other work from home company logos.
Boom! That’s it.
Up Next: Setting expectations of what working from home will look like and how it will work.
How Working From Home Will Actually Work
Setting expectations is one of the most important things to do to convince your boss to let you work from home.
The primary goal of setting expectations is to establish a baseline / starting point for how working from home will work.
Without proper expectations, bosses are likely to be hesitant to approve you working from home.
By addressing any unclear areas or concerns, it gets everyone on the same page. And that’s our goal here.
As a result, we are going to set specific and clear expectations on how working from home will work.
What Work From Home Expectations Should Be Set?
The lifestyle you choose will determine the expectations you need to set.
Do you want to work home in one location?
Or do you want to travel to different countries frequently?
Either way, you’re in luck as I’ve included expectations for both primary use cases (travel vs. not travel).
Before we dive into the use cases, let’s make one thing clear.
Regardless of your location, the biggest expectations to set are your primary job responsibilities.
In other words, how do you plan to make working from home a success?
Think about your top three to five job responsibilities and how you will complete them working from home.
For the most part, these will probably not change too much. The only difference is that you will not be one desk away from your boss when doing them.
A few examples of job responsibilities might include:
Team & Client Meetings/Communication
Solution: We can use email or internal communication tools (e.g., Slack) for written communication. All audio communication can be done via phone calls or virtual meetings (e.g., Zoom, Google Hangout).
Maintaining Project Statuses/Timelines
These are broad examples, but most responsibilities can be completed with some type of software.
The underlying purpose of this exercise is to show your boss that you are proactive and have a plan.
Before we move on, there are a few more expectations to set pending your desired lifestyle.
Expectations For Working At Home (Not Traveling)
- How You Will Communicate: Use tools such as Zoom, Slack, Asana, ClickUp, etc.
- Work Equipment and Environment: As mentioned earlier, either you can use company equipment or may have to purchase your own. E.g., Working at home, sometimes at a local coffee shop.
- Data Security/Privacy: Purchase a VPN (ExpressVPN.com) to keep company information safe.
- Work Availability: Even though it may seem obvious, we want to inform your boss that you intend to be working the same hours.
Expectations For Working At Home (Traveling)
The previous expectations (Communication, Work Equipment & Environment, Data Security & Privacy, Availability) all still apply here. Just two more additional expectations to set if traveling. They are:
- How Long and Where You Will Be Traveling: Share a rough itinerary of this timeline, along with expected hours of overlapping availability.
- Travel Emergencies: E.g., Embassies, hospitals, insurance, emergency contact, etc.
Some of these are more edge cases and probably more than what your boss will need to know. However, it’s essential to think through them and show that you thought out every detail.
Work From Home Success Expectations
Lastly, we will want to set the expectation of what success looks like when working from home.
Success is usually broken down into three areas. Below are some ideas for each:
- E.g., Complete all current key responsibilities with no delays, blockers, or issues related to working from home.
- E.g., Able to communicate clearly and effectively and show that I can do the job while working from home.
Evaluating the Arrangement:
- E.g., Monthly or biweekly check-ins to evaluate performance through systems to measure productivity and time reporting.
Trial Period Timeline:
- E.g., Start trial period on June 1st and evaluate on June 30th.
- E.g., Have a meeting at the end of the trial run to discuss future arrangements.
The most effective way to set success criteria is based on objective timelines and numbers. Therefore it’s black and white if the arrangement worked.
Pro-tip: Don’t be too harsh on yourself with these criteria, no one is perfect, and sometimes things are uncontrollable. Give yourself a little wiggle room here.
Setting Clear Expectations
Now that we know what expectations to set, we need to share them in a clear and concise way.
I’ve found the most effective way to do this is to share your significant expectations (role responsibilities) in the presentation.
Followed by sharing additional expectations in a separate game plan document.
Luckily, I’ve done all the hard work for you and created a proven game plan template that you can use.
>> Here’s your Work From Home Game Plan template. <<
If meeting in-person, you’ll want to have this additional expectation document physically printed. Or, if the meeting isn’t in person, have a hyperlink readily available to access the document during the presentation.
It’s ideal to go through all the expectations with your boss during the presentation.
The SECRET here is to directly ask if these expectations are unreasonable with “no-oriented questions”.
For example, “Is it unreasonable to think that we can use Slack for all our online communication?”
This method allows us to identify if anything is not reasonable or not fair. You can then address right there and figure out a solution.
Lastly, this game plan is great for everyone to reference in the future. Make the document shareable and have it bookmarked for easy access.
Adding Expectations to Your Presentation
To make sure we are on the same page, we add this to your presentation in two parts.
- Listing your primary responsibilities in the presentation. Followed by brief notes on how you will be successful at them when working from home.
- Filling out the Work From Home Game Plan template with all additional expectations. This will be shared in physical form or a hyperlink that we will use during the presentation.
Up Next: Now that you’ve got the major sections of your presentation done, it’s time to put on the finishing touches and present it to your boss.
Finalizing The Presentation
For the longest time, the single biggest thing holding me back from working from home was creating the presentation.
But luckily for you, along the way, you’ve already done the hard work and added the following points to your presentation:
- Directly asking your boss to work from home
- Sharing company benefits of you working from home
- Surfacing and providing solutions to common fears & objections
- Showcasing other companies that allow employees to work from home
- Setting expectations of how working from home will work
Note: If you haven’t started on your presentation yet, that’s okay. There’s a SECRET towards the end of this chapter to get started quickly.
Or if you want to avoid the heavy lifting of creating the presentation and didn’t take advantage of my presentation template earlier.
Then grab a copy of my proven presentation template to get results even faster:
Alright, so at this point, what’s left?
The last two small steps before we meet with your boss are:
- Add an “Ending / Next Steps” slide
- Making the presentation look professional
Ending / Next Steps Slide
The last slide is pretty straightforward.
We are going to list a few bullet points that highlight the next steps of the presentation/meeting.
This slide uses an “assumptive-close” approach.
For context, the assumptive close approach is a common sales tactic.
This means that we are sharing next steps as if the default outcome (assumption) of this presentation is to have you start working from home.
Here are some assumptive close bullet point ideas for your last slide:
Next Steps For Your Boss:
- E.g., Other internal approval/documentation to proceed
- E.g., Review the work from home game plan
- E.g., Decision timeline – when is it realistic to make a decision on this
Next Steps For You:
- E.g., Share the presentation, work from home game plan, and other deliverables
- E.g., Implement a system to measure working from home
- E.g., Anything else your boss/company needs from you
To be clear, when finishing delivering your presentation, you will likely not get an immediate “Yes” from your boss to work from home.
This is okay and should be expected. It’s a big decision to be made, and we don’t want to force them into an answer.
Instead, the assumptive close approach helps continue the meeting’s momentum into future conversations because it’s likely that future conversations are needed before you get approval to work from home.
Polishing the Presentation
While these may seem like minor details in your presentation, they go a long way in showing you are serious about working from home.
Here’s a simple checklist to make your presentation look and feel professional:
- Use your company’s branding – logo, color schemes, font type, etc. Ask design teams for brand/style guidelines and assets to follow/use.
- Clear and concise bullet points (and slide titles) that focus on the value your company/boss is receiving.
- Add relevant images throughout to help emphasize and humanize the bullet points. E.g., Company logos of other work from home companies or people happily working from home.
And as mentioned earlier, if you haven’t started creating your presentation, don’t stress.
Here’s the secret way to get started.
Copy everything you’ve typed in the “My Notes & Next Steps” sections (from the end of each chapter) and paste it into the “Speaker Notes” section (at the bottom of each slide).
Then add three to five bullet points from that “Speaker Notes” section to the slide.
These notes (at the bottom of each slide) are what you will be talking about in your presentation.
It may sound obvious, but the bullet points on your slides help your boss follow along. And for you to use as cues for the topics you are going to share on that slide.
Here’s an example:
Bullet point (on the slide): Saving Time – No Commuting to the Office
Talking point (speaker notes section): “By working from home, I’ll save 2 hours a day from commuting to the office. This will allow me to save that time and energy and instead use that time to work more and energy to be more focused throughout the day.”
If you think about it, these bullet points (on the slide) are essentially a high-level summary of what you will say.
And now that we have gone through all the actual slides/content in the presentation, it’s time to practice delivering the presentation.
Practicing the Presentation
If you are uncomfortable at giving presentations, you are not alone.
The best way to get over this discomfort is to practice. As you’ve probably heard before, practice makes perfect.
That’s why we’ve created a list of multiple ways you can practice your presentation.
Here are some techniques to practice delivering an effective presentation:
- Practice in front of a mirror. Make sure to speak at a normal talking volume to make it feel natural.
- Present it to a friend or family member and have them give you feedback.
- Record yourself presenting and watch the replay to see where you can improve.
- Print out a picture of your boss, stick it on a wall, and pretend you are presenting to them.
Additionally, these may seem like no-brainers, but it’s critical to know when giving a presentation, you should:
- Speak at a normal conversational volume level.
- Take your time, and speak clearly and concisely. Don’t rush through it.
- Avoid looking at and read off the slides word for word.
- Pro-Tip: Know your opening/closing lines between slides, any significant questions/asks (to work from home), or transition statements.
Lastly, if you need some more inspiration or another perspective on practicing a presentation, here are two high-quality resources from a Harvard Instructor:
- 5 Key Steps to Rehearsing a Presentation Like the Best TED Speakers
- How to Rehearse for an Important Presentation
Or if you would like me to help you practice the presentation, or create the presentation with you / potentially for you.
Then book a private one-on-one coaching session with me to get results even faster: firstname.lastname@example.org
Either way at this point, your presentation should not only be looking good but also sounding good too.
Up Next: Now, it’s time to set up the meeting and deliver the presentation to your boss.
The Meeting With Your Boss
At last, the moment you’ve been waiting for, you are finally ready to meet with your boss!
This may seem like another big obstacle to overcome because it’s easy to think that many things could go wrong. Plus, you may get nervous and stressed out about presentations.
But take a deep breath and remember, you’ve got this!
The hardest parts are already done. Now, it’s merely having a conversation and sharing what you know.
To make life easier, I’m going to walk you step-by-step through the meeting.
Before we go into the specific frameworks to have a successful conversation, let’s break down this meeting into bite-sized pieces so you know what to expect.
Breaking down the meeting will help us focus on what we can control and not stress about what we can’t control.
The meeting consists of four parts:
- Setting Up the Meeting
- Having the Meeting
- Ending the Meeting
- Following Up From the Meeting
Setting Up the Meeting
The first conversation should be with your boss / direct manager. Ideally, this person supports you, and you aren’t afraid to approach them.
Getting your boss on board is essential. They will be your best advocate if additional approval is needed.
There are two ways to go about setting up the meeting – verbal and written communication.
The preferred method here is written communication (specifically email).
This method allows you to craftily word your message, give your boss time to digest & respond to the message, and leave a communication paper trail.
If you can’t use written communication, then it’s preferred to set up a time with your boss in a one-on-one setting.
Since you know your boss better than me, go about scheduling a meeting with them as if it were any other routine meeting. In other words, don’t overthink it.
An email script that works very well in setting up the meeting looks like this:
Subject Line: Share Work Environment Improvement Ideas
Hi [Boss’s Name],
I wanted to see if we could schedule a meeting to share some ideas I have for improving my work environment. More specifically, I’m looking to become more productive and more valuable to [Company Name], and have an idea I would like to discuss with you.
I’ve gone ahead and sent over a calendar invite for [insert specific dates and times] to discuss. Please let me know if that time doesn’t work for you.
If not, I’m available at [insert specific dates and times]. Please advise.
Looking forward to sharing more with you soon!
The SECRET here is to send a calendar invite proactively.
Don’t go back and forth on coordinating times. Look at their calendar (if you have access) and schedule it.
It’s best to send the calendar invite right after you send the email.
If you can’t see their calendar, still send a calendar invite right away, but with a time you believe they will be available.
Additionally, in the outreach email, include other times you are available.
For example, “Please let me know if that time doesn’t work for you. If not, I’m available Wednesday and Thursday from 2 PM – 4 PM.”
This allows for backup times if the first one doesn’t work. Plus, it reduces the friction of securing a time and potential questioning of the meeting’s reason.
Having unnecessary communication on meeting logistics allows your boss to question/think more about the purpose of the meeting. Making them likely to ask more questions before agreeing to it.
This might lead to you explaining more, making your boss nervous, or putting up a wall of caution when meeting with you.
Or they might make assumptions based on the limited context that becomes difficult for you to overcome during the actual meeting.
Getting back to the logistics of the meeting. It’s best to schedule the conversation either that same week as the outreach message or the following week.
Also, make sure to know if your boss is taking a vacation around that time before reaching out.
Oh, by the way, block off 1-hour for the meeting. Don’t let time restrict your presentation.
The reason being is that everyone feels better to finish a meeting early and have extra time, rather than having to extend past the original slotted time and feel late for something else.
If your meeting is virtual, add a Zoom or Google Hangout link to the calendar invite. This is so you can screen share your presentation.
As for the outreach message’s timing, it’s ideal to send this message mid-to-late week (Wed / Th), in the later afternoon (2 PM – 4 PM).
Reason is that on Monday, everyone is focused on work, Friday everyone is checked out for the weekend, mornings people are tackling their priority projects. As the day goes on, people become more willing to listen / susceptible to ideas, and of course, no one should be distracted by emails on the weekends.
Jumping back to the verbal communication method.
If this is the primary option for you, most of the above still applies to you – the same timing, message, time expectation, etc.
The main difference is that when you talk to them, secure a time right then and there.
Ask them to open their calendar (have yours ready to go on your phone) and book a time on the spot.
Boom! You’ve got your meeting. Great work!
Having the Meeting
Going into the meeting, remember to take a deep breath and remember, you and your boss are on the same team in this meeting.
It’s just like any other conversation you’ve had with them. And if you are a little anxious, just know that this is a healthy sign from your body.
A few tactics to help calm the nerves before a meeting include:
Smile! – It increases endorphins, replacing anxiety with the state of being relaxed, making you feel good about the meeting.
Quick Exercise – Another way to increase endorphins. Try some air squats or take a morning run/exercise the day of the meeting.
Deep Breaths – Pretty obvious, but this circulates oxygen throughout your body to calm you down.
Power Poses / Stances – It’s up for debate, but spreading out can help with confidence. Typical poses include standing with a wide base (feet spread apart), standing with hands on hips, arms raised in a “V” overhead, etc.
Talking Outloud – Before the meeting, talk out loud at a conversational-level to clear your throat and sound normal.
Adjust to Your Surroundings (In-person) – If possible, arrive in the room a few minutes early and get comfortable by letting your body naturally adjust to your environment.
Once you are relaxed, it’s time to confirm that the entire technical setup works.
If you are in a room with your boss, bring your laptop to use for the visual presentation.
Or, if you only have a desktop computer, email your boss right before the meeting and have them pull it up on their computer. Ask to use their mouse to control the presentation.
If it’s a virtual conversation, have your presentation ready to go in a tab, and clear out the rest of your applications/tabs to avoid distractions.
Now, onto the actual presenting part.
Before you dive into the presentation itself, it’s always helpful to have work/personal banter to break the ice.
This could be asking them about something they are excited about in their personal life, a comment of praise about a team member, a recent work project, or simply asking how their day is going.
The point here is to get them talking about themself and ease into the presentation.
Once there has been some good banter, then it’s time to transition into the presentation. As mentioned earlier, it’s an excellent tactic to know your opening/closing and transitioning lines.
Here’s an example of transitioning into the presentation.
“Anyways, as stated in my email, the reason we are talking today is because I want to share a few ideas I have for a more productive workspace and being more valuable to [COMPANY NAME].
I believe the ideas shared here can be extremely impactful; therefore, I’ve put together a presentation to explain them.”
Then open up the presentation and direct your attention to it. Your boss should also naturally turn their attention to the screen too.
A few points to keep in mind to make your presentation effective and more of a conversation than a lecture:
- Lead the Conversation: You are in control of this presentation. Step up to the plate and lead.
- Make Eye Contact: This shows you are serious and so you can see your boss’s expressions and reactions.
- Have a Confident Voice: If you aren’t confident about this plan, your boss won’t be either.
- Take Pauses / Don’t Rush: After each slide, take a brief pause to let the information sink in and allow time for questions before moving on.
- Don’t Hide Anything: Be upfront and honest. Not sharing critical information is a fast way to lose trust and the opportunity to work from home.
- Ask If They Have Questions: At the beginning of the presentation, tell your boss they are free to ask questions throughout the presentation. Additionally, you can ask them every few slides if they have any questions. If they ask a question that you will answer in an upcoming slide, tell them it’s a great question, and you will answer it in a few slides. It’s essential to stay on track with clear and concise answers, and not get side-tracked from the presentation too much.
Most of these points probably sound like proper presentation etiquette. If so, that’s great because it shows you already have excellent standards of what a successful presentation looks like.
Above all else, you’ll do well if you treat it like any other professional conversation. Just have confidence in yourself and your game plan.
Ending the Meeting
This part is the last slide of your presentation (Ending / Next Steps slide).
Aside from what we discussed in Chapter 7 with the assumptive close, again, the purpose of this slide is to address any outstanding concerns and create next steps.
You’ve already rehearsed responses to the majority of objections your boss is likely to have.
To be clear, if you don’t have an answer to their concern/objection, don’t make something up. Tell your boss you will follow up with a response after the meeting.
Now that concerns are out of the way, that leaves us with next steps.
Rather than waiting for your boss to ask for your proposal for next steps, we are going to beat him to the punchline with a SECRET negotiation tactic that expert Ramit Sethi calls The Briefcase Technique”.
Here’s how it works:
When discussing the next steps, either your boss may ask, “e.g., How is this going to work?”, “How do we proceed from here?, etc.”, or you will need to initiate next steps.
When this time comes, say something like this:
“I’m glad you asked about the specifics. I’ve done a lot of research into how other companies have implemented successful work from home policies.
*[Cue briefcase technique]*
And I created a game plan that outlines and addresses all the logistics and concerns of me working from home.
- How I’ll execute my job responsibilities and communicate with others.
- My home office setup and security measures to protect company data.
- My proposed work from home schedule and availability.
- Ways we can measure this work from home arrangement and check-in.
Would it be unreasonable to go through this plan right now?”
At this point, if you haven’t already grabbed your copy of the Work From Home Game Plan, recommend to do so therefore you can print it out or send via email.
The Briefcase Technique is effective here because it makes it difficult for your boss to say no. It shows that you’ve already thought out and offered proactive solutions for all potential challenges.
PS: This is a great negotiation tactic for getting a raise or landing a new client too.
Following Up From the Meeting
This might be hard to believe, but the follow up is probably the most critical part of the meeting.
Well, you may have given a rockstar presentation, but that doesn’t mean anything unless we initiate action from the meeting.
The most effective way to follow up is within 24 – 48 hours after the meeting with some form of written communication (email preferably).
24 – 48 hours because it’s still fresh on their mind. And written because everything is clear and concise, and easy to reference back to.
Additionally, this email gives you the opportunity to:
- Share materials from the meeting (presentation, etc.)
- Follow-up on any questions you didn’t answer
- Restate next steps for both sides
To make things easy for you, here’s a proven email script to following up:
Subject Line: Follow Up From Work From Home Discussion
Hi [Boss’s Name],
Thanks for taking the time the other day to listen to some ideas for improving my work environment and becoming a better employee at [Company Name].
This message aims to follow up on our wonderful conversation and share with you important notes, promised deliverables, and next steps for everyone.
Here are important notes and promised deliverables:
- Presentation [Link Here]
- Work From Home Game Plan [Link Here]
Additionally, I promised an answer to your question regarding [e.g., company data security].
After evaluating potential solutions, I believe it would be best for us to [e.g., have me purchase a VPN (ExpressVPN.com) to keep company information safe].
Lastly, I wanted to resurface the next steps to keep the conversation going and arrive at a solution to allow me to work from home.
- [Bullet from your last slide. Both for you and your boss.]
- [Bullet from your last slide. Both for you and your boss.]
- [Bullet from your last slide. Both for you and your boss.]
Please let me know if you have any questions about the next steps above.
Excited to get this going and executing on a solution that works for everyone!
In a small likelihood, your boss may have already sent you an email before you have time to send this follow-up message. Regardless if they do or not, you should still send this follow-up message.
Heck, you can even have this email drafted up before the meeting and fill in some details shortly after, and then hit send the following morning.
The point here is to send the email and follow up on your promises – unanswered questions, sharing of presentation / game plan, etc.
If you send the message and don’t hear anything back after 72 hours, then it’s best to send a friendly nudge making the excuse that you wanted to confirm that they received your message.
For example, “Hey [Boss’s Name] – Hope you are doing well. Kindly checking in here to make sure you received my follow-up. Thanks!”
Chances are they saw the message and are either working on the next steps or having trouble moving forward.
If so, don’t pressure them. Instead, work with them.
Ask if anything is unclear. Or if someone or something is holding them back from approving.
Common examples include approval from other team members/management or fear of saying yes.
Either way, it’s best to uncover these and show your boss that you’re here to help. Work with them to address any remaining concerns or next steps to getting the final approval / yes.
Simply put… It’s your freedom; make it happen!
But before we move onto the final chapter, I want to congratulate you!
You’ve earned it. Seriously. Bravo!
You’ve learned all about the benefits of working from home, overcoming common objections, companies with work from home policies, setting expectations, and much more.
Additionally, you’ve put together a rockstar presentation and rehearsed it like a pro.
And when it came time to the meeting, you stepped up to the plate and gave your boss a presentation they won’t forget.
You’ve done everything you can in your power to convince your boss to let you work from home, and you should count that as a success.
And more importantly, you should be proud of yourself for what you’ve accomplished. I’m proud of your effort. Well done!
Up Next: Now, it’s up to your boss/company to give you their final decision.
PS: Here’s the email scripts for easy access:
The Decision: Work From Home Approval or Rejection
Ok, now it’s time for the moment we all have been waiting for – the decision from your boss.
The two outcomes of your efforts are either approval or rejection from your boss/company.
And to be clear, rejection does not mean no forever.
It’s just a no for RIGHT NOW.
So let’s talk about handling these potential outcomes and the next steps to take from them.
Work From Home Rejection
Whether it be a date, asking for a raise, or in our case, being able to work from home, no one wants to be rejected.
If rejected, your initial reaction might be anger towards your boss. You might want to find a new job or tell them you quit unless you can work from home.
A million things were going through my head when I got rejected by my boss the first time.
The most important thing here is not to stress and assume the worst-case scenario. It’s easy to do this because we often suffer more in imagination than in reality. Thanks, Seneca.
Showing anger or resentment will only push you and your boss further apart from each other. And in this dynamic, you are on the same team.
Instead, take a deep breath. And remember it’s just a no, for right now.
If faced with rejection, our next step should be to ask why.
Why couldn’t we be approved to work from home?
Is it because of fear or an objection? Or maybe they can’t trust you because you’re too new to the company? Or the benefit is unclear to them?
At the core, our goal is to identify what’s holding them back.
Note: They may have shared this reason with you when they told you no. They probably said we couldn’t let you work from home because [insert reason].
If they didn’t share the reason, the most effective way to uncover this reason is by simply asking.
Here’s an ideal way to phrase this:
“Thank you for sharing your decision regarding my ability to work from home.
I trust you have thought a lot about this decision, and it was not easy to make.
You’re probably going to hate me for this and think I’m the worst employee ever, but is it unreasonable to ask… why you were unable to approve of me working from home?”
If you are going to use any part of that phase, make sure to use the bolded part in the last line.
That line is dangerously effective for asking for practically anything. Plus, it’s a “no-oriented” question.
When your boss tells you why they can’t allow you to work from home, it’s important not to interrupt them and react with a knee-jerk reply.
Instead, let them talk and listen to them. You can even display you are listening to them by writing down their feedback.
Once they are finished, take a deep breath and give them a chance to share anything else.
The more information they provide you, the better your response will be.
Once they are done, then it’s time to address their reason(s) for rejection.
You can show you understand them loud and clear by repeating their concerns at the start of your response. Followed by offering a solution to overcome the objection.
After you have proposed a potential solution, you should ask for their feedback on it. Here are a few ways to phrase the feedback ask:
- What do you think of that proposed solution?
- Is it unreasonable to think that this would work?
- Is there any potential solution you can see working here?
The key here is to get them talking and working together to overcome any final concerns.
And remember, if you don’t have an answer, don’t make something up. Simply acknowledge and appreciate them sharing their concerns, and that you will follow up soon.
Sometimes, all that’s holding them back is just a few minor details, but it can be solved with more clarity.
And if it’s a flat-out “no” with a hard no reason (e.g., they say it’s against company policy – common objection), it’s best to try and propose a 2-3 week “trial run” with a post-evaluation.
Or propose being out of the office for two days a week and revisit the plan every few weeks until you work your way up to being able to work from home full-time.
And if those attempts get rejected too, and working from home is a deal-breaker for you, well, then there are a few alternative options.
To be clear, I wouldn’t advise these as initial strategies; however, I’ve seen them be successful.
- Approach your boss’s manager with the ask to work from home and explain to them the circumstances.
- Tell your boss you are quitting unless you can work from home.
- Substitute compensation for the ability to work from home. (e.g., next review, don’t ask for more money, ask to work from home).
- Consider getting a new work from home job (e.g., We Work Remotely: Remote Jobs, Remote.co: Remote Jobs, etc.).
The bottom line?
A “no” doesn’t mean no forever. Don’t give up.
Work From Home Approval
On the other hand, if you’ve followed this post (and the book) and put in the effort, there’s a high probability that your boss tells you that you are approved to work from home.
If “Yes” is the decision, I want to be the first to say Congratulations!
It’s well-earned and well-deserved.
Even if it’s only a two-week trial run, that’s still a huge success!
Not only am I incredibly proud of you, but I’m excited about what you will be able to do now that you are free!
Go out and set the world on fire! (Not literally)
In other words, spend more time with family and friends, travel the world, or take back control of your time by avoiding the dreaded commute to the cube farm.
Set out to do what you’ve always wanted to do!
Now in the case that you are approved for a short trial period, all you have to do is execute on the plan and expectations you laid out.
The key here is to show them that you are just as effective working from home as an office.
This can be done by:
- Sharing time measurement reports (project management, time tracking).
- Showing that you made all your meetings, no delayed communication, no tech setup/privacy issues, etc.
- Comparing expectations and reality (we said “X” and “X” happened).
After your trial run is over, you will most likely have another conversation with your boss. Be prepared for this conversation with bullet points on expectations versus reality.
If the trial run was successful, the most critical thing in this conversation is to ask that, moving forward, that you want to work from home full-time.
Same process as before (handling objections, setting expectations, benefits to the company, etc.), just different time lengths.
Anyways, I don’t want to shy away from your success. Again, congratulations!
Now It’s Your Turn…
Which tactic from today’s post are you going to try first?
- Are you going to try using the company-first approach?
- Or how about downloading the free work from home book?
Let me know by leaving a comment below, right now.
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