How to Decide if Working Remotely is the Right Move For You (or Your Employee) (2023)

How to Decide if Working Remotely is the Right Move For You (or Your Employee) (1)

When I had my first interview with HubSpot, I’d been a proud Californian for exactly two weeks. I cringed as I emailed my recruiter, “I’m so excited for this opportunity, but I just moved -- and I can’t do it again.” His reply was swift and easy, “Oh, that’s no problem, we’re open to this position working remote.”Once I’d stopped popping bottles in disbelief over my good luck, the reality set in. Could I do it? Was I cut out for remote work? Would I feel cut off from the company and my role? HubSpot makes it look easy, but there are a lot of logistics, planning, and thoughtfulness that go into hiring a new remote worker or transitioning an existing HubSpotter to remote status. And then there are the tough personal questions you have to ask yourself. Not the least of which is, “Can I do my best work as a remote employee?”

Because this is such a sensitive topic, HubSpot Senior Recruiter Sara DeBrule and I (Meg Prater, writer on the HubSpot Sales Blog), decided to collaborate on this helpful list that tackles remote work from two points of view:

  1. A current employee deciding whether remote work is right for them.
  2. A manager hiring a remote employee or fielding a request for an in-person employee to go remote.

So, let’s get started.

Questions to Ask Yourself About Going Remote

I’ve talked to some colleagues who state emphatically, “I could never do remote work,” and others who treat it as a mystical land of plenty.

The fact is, it’s a tricky balance between both. Some days, I feel like no mere mortal can keep me from crossing every last item off my meticulously crafted to-do list. Other days, I’m lucky to cross five items off that list, feel like I haven’t communicated with an actual human in at least six light-years, andonly remember how to speak dog.

To work remotely, it’s helpful to be structured, resilient, and, above all, forgiving. We all have our days. What matters (especially) in remote work is that you can pick yourself up and move forward productively.

Here are a few questions to ask yourself and your manager before considering a remote position.

Be honest about your habits, personality, and the nature of your work.

1. How are you motivated?

Are you self-motivated or does it take the buzz of an office and a cheerful smile from a coworker to get you going in the morning? There’s no wrong answer here, but it’s important to know you can draw from internal motivation to produce results and succeed in a remote environment.

2. How do you get energized during the work day?

Do you complete your best work by throwing ideas off colleagues or brainstorming at after work happy hours? That doesn’t mean you won’t thrive in remote work, but you should consider how these experiences will change outside the office. Will you feel the same lightning strike if you’re conducting that same brainstorm during an hour-long structured meeting or quarterly visit to the office? If not, consider whether this is the right move for you.

3. Think about your ideal day at the office.

Do you get in early, knock out a few tasks in relative silence, breeze through a few meetings, and grab lunch at your desk while checking off the rest of your to-do list? Or would that ideal day start with a coffee meeting, include lunch with your team, and end with a company trivia session and happy hour?

Again, neither answer means you can or can’t swing remote work, but the key here is maintaining a happy, healthy work life, and if you’re happiest and most inspired around colleagues and at company events, consider what you’re giving up if you go remote.

Questions for Interviewers/Managers to Ask Potential Remote Employees

When you’re interviewing a potential new hire for remote work, it’s important to learn how they’re motivated, how they structure their days/challenges, and where they draw energy from throughout the day. If you’re working with existing employees, it’s important to consider the request through a similar lens. Here are a few questions to ask both candidates:

Characteristics, habits, or traits you’re looking for in a remote hire.

1. How do they stay organized?

  • “How do you organize yourself and/or your team around projects?”
  • “How would you communicate about/manage projects from outside the office?”
  • “Would you consider yourself assertive? If so, tell me about a time you exercised that assertiveness.”
  • “How do you organize your day?”
  • “How and where do you do your best work?”

2. Are they collaborative?

  • “What’s your process for working with others?”
  • “If someone asks you to start a project, what are your first steps?” (If they lean on in-person interactions like calling a meeting or swinging by someone’s desk, this could be a red flag, as opposed to someone who tends toward introspection to solve a problem or kick off a project.)

3. Are they a self-starter?

  • “Tell me about a time you recognized something was broken in your business. What did you do?”
  • “How do you overcome obstacles?”
  • “How do you recognize difficult situations and identify solutions?”

4. Do they know what they’re signing up for?

  • “What resources have you read to understand what a remote work experience would be like?” (Did they view remote companies on Glassdoor and read reviews? Do they follow certain remote work blogs? Have they talked to fellow remote employees?)
  • “What is it about remote work that appeals to you?”
  • “What are your concerns about remote work? What do you think will be the obstacles?”

Red flags to consider.

Note: These aren’t hard-and-fast rules. A red flag might not correlate to a person’s ability to succeed in a remote position. But these areas are worth digging into if initial answers are worrying.

  • If their response to “How do you successfully collaborate” relies on in-person interaction (i.e., desk fly-bys, meetings, coffee breaks), ask why those are their preferred methods for discussing new projects and how they would handle these same situations outside the office.
  • Ask, “What energizes you at work?” If the answer is, “Solving complex projects,” or “Finding a quiet spot in the office to churn through email,” you might have a good remote candidate on your hands. If their answer is, “Grabbing mid-morning coffee with colleagues,” or “the company's great team-building opportunities,” ask clarifying questions to understand how this person will find that energy outside of your organization's physical walls.
  • Ask how this person likes to be managed. You’ll have a better pulse on this if your remote candidate already works for your company. Regardless, ask “As a remote employee, what are you looking for in a team and manager?” If the answers revolve around hands-on management and a close-knit team, these could be red flags. If, however, answers point toward independence and the ability to ask for help and community as needed, this could be a sign this person is a good fit for remote work.

Establish your company's remote work policies and expectations.

Whether you’re dealing with a new hire or a longtime employee, it’s likely they don’t know much about about your company'sremote work policies, or the unique guidelines in place for each department and team. Set clear expectations for remote work during the interview or approval process. Here are a few ways to do that successfully:

  • Establish how your company does and does not support remote workers
  • Be honest about what stage the company and your team is in when it comes to remote work
  • Connect them with other remote workers in similar roles
  • Leverage current remote employees to interview late-stage remote candidates
  • Identify how success will be measured
  • Establish a routine for checking in with managers, colleagues, and mentors
  • Define the path for career advancement as a remote employee. How will expectations and career growth change for current employees if they go remote?

These can be difficult questions to ask, but it’s important for both parties to understand whether their best work will be completed remotely.

The future of work is becoming more and more remote every day. Remote work isn't for everyone, but for some it's the way they work best. So, next time you're thinking about what working remotely might look like for you or your employee, think through these questions and topics to really decide if working away from the office is the right move for you.

Originally published Sep 10, 2018 8:30:00 AM, updated January 19 2023


How do you know if a remote job is right for you? ›

Signs You're Ready for a Remote Job
  • You're Excited By Remote Work. ...
  • You Thrive When Working Alone. ...
  • You Have Top-Notch Communication Skills. ...
  • You Can Navigate Technical Problems Yourself. ...
  • You Know How to Deal With Distractions. ...
  • You Loathe Your Commute. ...
  • You Have Health Issues. ...
  • You Need Some Flexibility.

Is it better to work remotely or at your workplace? ›

Work/life balance

The ability to work remotely offers a better work/life balance. Working away from the office can make you feel in control of your life and give you more time to plan both work and home tasks. This gives a sense of achievement and makes employees more productive.

How do I decide who works remotely? ›

Characteristics of positions that DO lend themselves to telework
  1. Job duties can be conducted outside of the worksite.
  2. Teleworking does not affect the service quality or organizational operations.
  3. Teleworking does not add additional cost to the employer.
  4. Teleworking does not negatively impact team performance.

Why you should let your employees work remotely? ›

Add in the lack of a commute, and remote workers typically have more time and fewer distractions, which leads to increased productivity—a huge benefit of working from home for both employees and employers alike. When done right, remote work allows employees and companies to focus on what really matters—performance.

Should I take a remote job that pays less? ›

On average, you should ask for a raise every one to two years, especially if your current employer doesn't automatically give you one. Don't accept a pay cut just to work at home. In general, most employers are willing to negotiate a remote work arrangement without you taking a hit on your earnings.

Should I take less money for a remote job? ›

And there's no right or wrong answer. If you would give almost anything to work remotely, then a pay cut may not be such a sacrifice. If not, then don't rush to accept a remote position offering a salary you feel is too low. Instead, keep looking for an ideal role in the location and salary range that works for you.

Are people happier working remotely? ›

Are Remote Workers Happier? A survey report conducted by Owl labs suggests remote workers are happier and stay in their jobs longer. They also found that workers who were working at home reported being happy 22% more than workers who always work in an onsite office environment.

What should you not do when working remotely? ›

Avoid distractions while working from home as much as you can. Even though it is essential to check your emails throughout the day, you do not have to keep them open all the time. Block an ideal time to review your emails. The same goes for social media, and it is more distracting since it is more recreational and fun.

Does remote work make employees happier? ›

A survey by mental health research website Tracking Happiness found that the ability to work remotely is positively correlated with employee happiness. Fully remote workers reported a happiness level roughly 20% higher than those who worked in the office 100% of the time.

What is the 3 2 remote work policy? ›

3:2 model: Employees spend three days in the office and two days at home. This hybrid work policy is easy to coordinate and allows everyone to be in the office on the same days of the week.

How do I set boundaries when working remotely? ›

How To Maintain Boundaries Between Work and Home
  1. — Create a Dedicated Workspace. ...
  2. — Set and Keep a Regular Schedule. ...
  3. — Get Dressed. ...
  4. — Recreate Your Commute. ...
  5. — Ban Distractions. ...
  6. — Set and Stick to Boundaries. ...
  7. — Take Breaks. ...
  8. — Take Time Off.

Can you allow some employees to work from home and not others? ›

According to the Civil Rights Act, it is unlawful and may result in a federal prosecution, including jail time if found guilty. Specifically, working from home discrimination is a real issue. It is one of many forms of workplace discrimination.

What are the drawbacks of working from home? ›

Top 7 Disadvantages Of Working From Home
  • Lack of community and teamwork.
  • Lack of Motivation.
  • Unmonitored performance and those frequent breaks.
  • Lack of Office Equipment and Security Concerns.
  • Distractions and lack of a good working environment.
  • Burnout.
  • Risk to productivity.
Apr 27, 2023

How do you take advantage of working remotely? ›

Set a schedule and stick to it... most of the time. Having clear guidelines for when to work and when to call it a day helps many remote workers maintain a work-life balance. That said, one of the best benefits of remote work is flexibility when the job allows for it.

Will remote work end? ›

Remote work 'is a trend that's not going away,' Almanac CEO says. Almanac CEO Adam Nathan joins Yahoo Finance Live to discuss post-pandemic remote work, the debate between remote vs. hybrid vs. in-person, companies requiring office attendance, and the outlook for the modern work crisis.

Is it healthier to work from home or office? ›

People who work from home may find it easier to maintain their physical health than those who work in an office. Since they don't commute in the mornings and evenings, they might use the extra time to rest or complete an exercise program.

Is it better to work from home or work from home office? ›

Is work from home better than work from office? Both work from home and work from office has its own advantages and disadvantages. If you wish to cut-down the commute time and increase productivity, then work from home is better. However, if you focus on better collabaration then working from office is better.

Is remote productivity better than in office? ›

New research finds that fully remote workers are less productive than their in-office counterparts. A new study looks at the productivity of remote workers versus those in-office. It showed that productivity was lower among a group of workers randomly assigned to WFH.

Is back to office better than remote work? ›

Those working remotely appreciate ditching the commute, cutting the costs of going to the office, and even having a better work-life balance, Stuart said, while those who prefer working in the office appreciate the sociability of it, the networking, and the spontaneity.

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