How To Negotiate A Remote Work Arrangement

Hey everyone! Today I have a killer post for you by Mrs. Adventure Rich from She was able to convince her employer to let her work remote! As someone who works from a computer at home, I can tell you that it’s not a bad way to do it haha. She has some great tips for anyone that wants to try and do the same. Enjoy! ~M$M

What started as a typical day in late May 2016 quickly spiraled into a day filled with dreams and possibilities. As I took a break at work, I resorted to my favorite search and browsed jobs in the Midwest.

Not jobs for me…jobs for my husband.

At the time, I lived with my husband and son in southern California. My career at a Fortune 50 company was strong and we were enjoying our time and our local community. But we longed for more stability, a lower cost of living area to settle down and a community to thrive in.

We did not see this as a real possibility in southern California and were searching for jobs near one of our families (my family in the Midwest, his family on the East Coast).

On that day in May, I stumbled on a job posting at a prominent employer in the Midwest near my family. It sounded perfect. Similar to my husband’s current role, though in a different industry. I immediately texted the job over with something along the lines of “APPLY?!?!?!?!”

New Job Possibilities

Over the next few weeks, my husband applied, interviewed and realized that the job was not exactly what we thought it was and he may not be the right fit. But the company reached out and asked if he was interested in another job and by mid-July, he received an official job offer.

We were thrilled! We finally could see a feasible path back to an area we loved and a place to settle in. But there was one, glaring elephant in the room… my job.

While the job offer my husband received was competitive for the Midwest, I have brought home the larger salary throughout our entire relationship and marriage. Losing my salary would majorly impact our financial goals and our ability to save and invest. And financials aside, I love my job.

I did the only thing I could do. I approached my employer to negotiate a remote work allowance. I did so by taking the following actions.

How To Negotiate a Remote Work Arrangement

1. Research company policies and technology needs

My first step when considering a request for a remote work arrangement was to research my employer’s policies and remote worker technology needs.

I am fortunate to work for a company with many remote workers and a developed work-remote program.

Home office security information, internet access requirements, and other remote work policies and procedures are readily available and I began to scour the requirements to make sure I could comply with each.

My specific organization, however, does not typically allow for full-time remote work (~98% of my organization works at a company office location). As a result, I discovered that my request would fall into an “exception” category (not a standard allowance).

2. Prepare a pitch

After learning of my employer’s policies and procedures, I began to develop a case for why working remote would be beneficial for my company, my leadership, my team, and myself. I had to be honest with myself about what would be better in a “work from home” set up and craft a pitch that reflected my reasoning.

A few of my reasons included the following:

  • At the time, my husband and I were parents to a 1-year-old. We both worked full time and, while we were managing, would greatly benefit from additional support. A move to the Midwest would create a network of support from friends and family (especially my parents), allowing me to be a more focused, engaged employee.
  • The lack of commute would create a better lifestyle, allowing me to dedicate time to my work without the overhanging weight of driving 2 to 2.5 hours a day for the office seat.
  • Many of the people I work with are on the East Coast. When working on the West Coast, I wake up 3 hours “behind” and cannot respond as promptly to early morning requests. By working on Eastern Time, I would be able to reply and meet with coworkers right off the bat, avoiding delays and holdups.

While brainstorming the benefits of working remote, I also tried to think through the potential downsides of working remote and how I would mitigate them.

A few of my downsides and mitigation plans included:

  • Less connection with the greater team: Working remote creates a significant separation from a team. I proposed several workarounds, including a willingness to travel to offices on a regular basis, a dedication to set up “virtual coffees” and periodic meetings with team members in order to remain connected, and a willingness to take on projects and roles that involved personally reaching out to members of our team on a regular basis (example: organizational project tracking).
  • Difficulty for my manager: I am fortunate to have excellent managers and relationships with my managers. But I did want to make sure they knew I would try to make their lives easier if I was working remote. To that end, I guaranteed that I would be readily accessible during work hours (company phone, email, and IM), provide a detailed weekly summary of my projects and work, and remain flexible for late-in-the-day meetings (2 pm Pacific is 5 pm Eastern!).

3. Conduct a professional meeting with management

With my pitch in hand, I asked my manager for a meeting. This meeting actually took place after my husband applied for the new job but before he received a job offer! I wanted to give my leadership as much time as possible to consider my request and gain necessary approvals.

During my initial meeting, I spoke to my manager in an open and honest way. I knew the decision would not be an easy one for my manager and I did not assume he would say yes. Much to my relief, he was quite supportive of my proposal but asked that I set up time with further levels of leadership (since he was not able to grant approval himself).

The next level leadership discussion was not quite as easy. I was asked to provide more detail about my motives, my plans, and my guarantees to help make a remote office successful. The meeting closed with an agreement that the leadership team would consider the request.

4. Follow up after the meeting to address any further concerns voiced in by management

While I had hoped for a more emphatic “yes!” right away, I was thankful that my management was considering a remote work allowance.

During the meeting with my team’s “next level leadership” (above my manager), my leadership raised several concerns about working remote. So, while waiting for a verdict, I decided to respond to each of the concerns. I met with my leadership a few days later to walk through each of the concerns he raised and my proposed solutions to the concerns.

This second meeting may not have greatly affected the outcome, but it could not have hurt. My leadership expressed appreciation for my careful consideration of their concerns and my proposed solutions.

5. Remain truly open to the possibility that management may say “no” (and have a plan for that situation)

With the meetings and solutioning complete, I had to do something incredibly hard… I had to wait.

By this point, my husband had a job offer in hand and we holding on responding to the offer while we waited for my employer to come back with a “yay” or “nay” to my remote work request.

During this waiting period, my husband and I worked through different scenarios. It would be one thing if my leadership says “yes” and allows me to work remote. But what if they say “no”? Would we stay in California? Would we move to the Midwest with my husband’s job and begin my job search there?

Through many difficult conversations and number crunching sessions, we developed a plan for each possible scenario. I also resolved to be open to any response and thankful for my employer’s consideration, regardless of the outcome.

6. If the remote work status is granted, show appreciation and go above and beyond to make the transition smooth

It may have seemed like excruciatingly long weeks of waiting for an answer, but in reality, my management granted my remote-work situation within a week or two of our discussion. I was ecstatic! The final piece of the puzzle was in place and we were able to move to our new home!

Knowing that the decision was not an easy one for my management, I tried to go above and beyond. I expressed my sincere gratitude to both my manager for his support and my leadership for their permission. I then took steps to make the transition as smooth as possible, sticking to my promises and mitigating any adjustment pains I could see.

One Year In

Now, after over one year of working remotely full time, I can say the new setup is an excellent fit for my life. I am able to spend more time with my son in the mornings and evenings, arrive at work energized and ready to work hard, and avoid portions of the job that previously brought me stress (e.g. commuting!).

In addition, my husband and I are settling into our new home, exploring the area, and becoming “locals” in our new hometown. I am thankful to my employer for the remote work setup and I believe the situation has proven to be mutually beneficial.

Posted in: Career Advice

About Millennial Money Man

Bobby Hoyt is a former band director who paid off $40,000 of student loan debt in 18 months on his teaching salary and then left his job to run Millennial Money Man full-time. He helps other Millennials earn more through side hustles, save more through budgeting tools and apps, and pay off debt. He is a personal finance expert who has been seen on Forbes, Reuters, MarketWatch, CNBC, International Business Times, Business Insider, US News, Yahoo Finance, and many other personal finance and entrepreneurship media outlets.

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