Top 9 Remote Work Lessons from AMA with Sara Sutton, CEO and Founder of FlexJobs

As the CEO and Founder of FlexJobs, the leading service for professional remote and flexible job opportunities, Sara shared her expertise and remote work lessons in our leadership community, The Watercooler

Watercooler remote work community

Every few months, we invite one of the 1,000+ managers who are a part of our leadership community, The Watercooler, from all over the world to participate in an “Ask Me Anything” (AMA) session. It’s an opportunity for managers, executives, and business owners to gain in-depth insights on remote work lessons. 

Last month, we had an AMA with Natalie Gould, CFO for Balsamiq, the remote software company that builds Balsamiq Wireframes – a product used by 500,000+ companies.

Other past guests have included Amir Salihefendic, CEO of Doist, Valentina Thörner, Happiness Team Lead at Automattic, and David Heinemeier Hansson (DHH), CTO at Basecamp.

Sara Sutton has long been passionate about helping people find jobs. She started her career in 1995 when she co-Founded JobDirect, the first online entry-level job service (sold to Korn|Ferry International in 2000). She is an expert and speaker on a wide variety of topics related to the future of work, such as the impact of remote work, the hybridization of the workforce (freelance v. employee), gender equity, economic development, unemployment and underemployment, and entrepreneurship. On these topics, she has appeared in hundreds of media pieces, including with Time, Marketplace Money, the Wall Street Journal, Fast Company, CNN, NBC, Forbes, Inc., and many others.

For her work in the employment and technology fields, she was named as a Young Global Leader (YGL) by the World Economic Forum and is honored to serve on the Advisory Group for the YGL program. Sutton holds a BA in Society, Technology, and the Environment from the University of California at Berkeley and resides in Boulder, Colorado, USA.

Sara believes a modern workplace should address the needs of today’s workforce, and that utilizing workplace technology to support telecommuting, freelance, part-time, and flexible work will achieve societal, environmental, and economic benefits for both employees and employers. As a result, she is committed to providing education and awareness about the viability and benefits of remote working and work flexibility. So in addition to FlexJobs, she has also launched an advocacy initiative, 1 Million for Work Flexibility; a resource for integrating remote work into business models, Remote.co; and The TRaD* Works Forum (*Telecommuting, Remote, & Distributed), a conference that brings together thought leaders, policy makers, and organizations looking to further leverage the diverse benefits of remote and distributed teams.

I learned so much following Sara’s AMA. Here were the top 9 remote work lessons I took from her:


Question #1

“I started working remotely from home in 2011. My daughter was two years old, and I was waitressing as a single mom. I couldn’t afford daycare. I remember scouring the Internet for work-from-home jobs that weren’t scams or MLM pyramid schemes but they disguise themselves pretty well and I ended up wasting a lot of time looking for remote work. What are signs in job postings that might indicate scams or that the job posting isn’t 100% on the up-and-up?”

Sara’s Answer:

Thanks for your question, and you’re very right that scams are a big problem in the remote job market! It’s the reason I started FlexJobs – to create a safe place for jobseekers. It’s actually estimated that for every one legitimate remote job, there are 60-70 scam jobs. Some are very simple and easy to spot, but others are far more sophisticated. Here are some things to keep in mind.

First off, pay attention to the URL of the site you’re on. You may think you’re on a well-known company’s career page, but scammers create copycat websites that look similar to a legitimate company’s page, but are really just a scam. If anything looks off (poor grammar, misspellings, vague job descriptions, lots of talk about making money, etc.), open a fresh browser and do a search for the company’s name and the keyword “careers” to find their true careers page. Then, see if you can find that same job in their real listings. If you can’t, you were probably just on a scam site.

We’ve actually detailed 9 of the most common job scams people should be aware of, so I recommend reviewing this blog post for more information. It also has examples of actual job posts that are scams so you can see the kind of red flags to avoid!

And before you even get to the job posting itself, make sure you’re using the right keywords in your online search. Keywords that legitimate companies use to describe their at-home jobs include telecommuting, remote job, and virtual job. Scammers typically use the phrases work-from-home and work-at-home jobs.

Rest assured, though, if you’re using FlexJobs, you’re guaranteed to not find any scams because EVERY SINGLE job and company is vetted by our research team before being added to our site. 😬

Question #2

“What’s the #1 thing you believe you can’t compromise on as a leader of a remote team?”

Sara’s Answer:

Proactive communication is truly the foundation of any healthy company in my opinion, and especially a strong remote work program. Proactive, open communication is critical to getting and staying on the same page when you work remotely, building good working relationships, ensuring expectations are clear, and giving honest, constructive feedback when problems come up. Leaders of remote workers (even partially) should make sure the right variety of communication methods are in place for their teams AND that their teams use them for the right functions/processes/etc. It’s something we discuss a lot on our teams, and we are a couple of articles we wrote on our sister site, Remote.co, about it to help other remote leaders and teams:

Question #3

“What do you think are the most common mistakes that remote leaders make?”

Sara’s Answer:

One of the biggest mistakes companies make when integrating remote workers is using “casual flex,” where the scope of the remote work program isn’t clearly defined, goals haven’t been laid out, hasn’t been thought through, and—most importantly—isn’t measured for impact. It’s great to be open to trying new things, and often trying an ad hoc remote arrangement a certain team member or team comes from a really good place… BUT, it’s rarely going to work well that way (for the team member or for the company’s culture).

Question #4

“What’s the best advice you have for someone who is managing a remote team for the first time?”

Sara’s Answer:

Managing remote workers is a bit different than managing in-house teams, but not as much as most people think. Both really rely on management best practices such as proactive communication, be engaged, having KPIs to assess productivity, provide support and training when needed, and care about your team, their success, and your mission. There are others, of course, but here are some just to give an idea. In fact, it’s very rare that you’ll see really good management advice for anyone NOT be good for remote managers, also.

Here are a few areas though on where differences can come in:

  • Remote managers need to shift in management practices to rely less on visuals, body language, and “facetime” and focus more on more on proactive communication, regular check-ins, goal-setting, and results-focused management.
  • All managers can benefit from relying less on face-time and more on process and results, but especially for first-time remote managers, over-communicating is better than under-communicating.
  • Just because you’re managing a remote team (particularly of employees), it doesn’t mean that culture isn’t as important as if you were in an office… in fact, company culture is more important to be conscientious of in a remote environment because you can’t fall back on in-office casual culture to develop.

For more, here is an article I wrote for Fast Company on How to Hire and Manage Remote Employees. 😊

Question #5

“First, know that we have used your site on some of our job searches. One thing I like about it is we can still be location specific. Some of the other sites require you don’t mention a location. We are a remote first company, but we still have reasons for looking for candidates based out of specific states or countries.

We’re just starting a salary and professional growth improvement project, so I’d like to ask you what advice you have related to setting salaries in multiple locations.

Our current system is: “You are paid a little better than someone with your same job in your geographical area.”

Sounds simple right. 🙂 But defining the “same job” in multiple locations and trying to find reliable data for those markets – including trying to incorporate different social net/benefit systems into that calculation – can be difficult.

What advice or resources do you have for small companies exploring salary setting policies in various locations?”

Sara’s Answer:

it can be tricky.

I’ve seen companies try to approach it with a “one rate for the role” and just stay equitable across the board, but the obvious problem is that doesn’t account for cost of living adjustments, market competition considerations, etc.

So we recommend trying to create a winning compensation package that will be considered a win-win by both the employer and the worker. To do that, it’s good to consider a number of data points (some of which I’m sure you’re already doing, so I apologize for any duplicity):

  • Try to get a sense of the candidate’s ideal range early on in the application process, and whether it’s in our budgetary ballpark.
  • Use several salary comparison resources (Glassdoor, Salary.com, Payscale, your PEO’s resources, etc.).
  • Consider similar roles on your team and their compensation levels.
  • Research similar job listings from other companies to see if they include a pay range.
  • Have a real sense of the value of the role will have on your company.

I hope that helps! 🤑😉

Question #6

“How do you go about determining values alignment in a candidate when hiring onto your team?”

Sara’s Answer:

This is always a bit tricky, of course. I’d say the first way to assess values alignment is to keep a keen eye out throughout the entire hiring process (from application received right up until offer) for clues on where each candidate falls on the spectrum.

For example, there can be early clues in a cover letter, simply by how they introduce and convey themselves as a candidate. In a resume, look at the organizations they’ve been involved with, and notice things such as whether any of the organizations on there have cultures that align with yours well (or not)? And how long did they stay?

The interview is the biggest, most clear opportunity to ask questions that pull this information out. Be sure to ask questions that help show the candidate’s true colors. I often ask things such as:

  • What’s important to you in a job?
  • What are you looking for in a company?
  • What 5 words would you use to describe yourself? Now, what 5 words would your best friend use to describe you? (Are they the same?)
  • How do you define success in your career?

Just try not to give away what you’re looking for, and then don’t lead them. You want to catch them a bit off the cuff so that they don’t give you a canned answer.

Question #7

“How do you deliver constructive feedback remotely?”

Sara’s Answer:

For me, it’s pretty similar to how you would in an office, with perhaps an extra consideration for communication method. First, I think about the recipient’s preferred method of communication, and then I think about whether I believe it will work for the situation at hand. If I’m a little uncertain, I also consult my VP of People and Culture for her insights. Typically though, I would never give constructive feedback via text and email only when it’s really appropriate.

Also, I would consider if you need documentation regarding the feedback. For example if you do and if you give the feedback by video or phone, be sure to let the person know that you’ll follow up by email with a summary of what you’ve discussed as a good way to make sure you’re on the same page afterwards.

Question #8

“What can co-located teams learn from remote teams?”

Sara’s Answer:

There are differences between distributed teams and remote teams, and there are more challenges in my opinion when it’s a hybrid situation of some people on-site together and others working remotely.

We’ve heard and seen a lot of success with co-located teams trying to approach situations as if they were all remote working. Such as, if one team member can’t be on video, then nobody should be on video because of the difference in communication cues between video and voice. This can have many benefits, such as having the in-office workers well-equipped to work remotely if needed suddenly (natural disaster that shuts the area down, which is unfortunately not all that rare these days), which is great to minimize loss of productivity that typically happens during those situations.

I would say that successful remote teams typically are implementing “best practices” of communication, collaboration, and management. And that can always be something that any team should be inspired by. 😊

Also, a big thanks for your shout out to Remote.co as such a helpful resource for the remote community! We really appreciate it, and my whole point in starting it was to be just that–to help others who are interested in integrating remote work into their culture or starting a remote company from scratch to have a trusted place to learn from others who have done it.

When I started FlexJobs as a remote company, I had to figure out so much on my own, especially when it comes to culture. It was not easy, but it’s definitely possible to create a fantastic work”place” culture in a remote environment, and we’ve won culture awards to prove it… including just this week being named a Top 50 Places to Work by Outside Magazine! (I love Outside, so I’m super excited about this one!) 🙂

Question #9

“I work in a Portuguese software house with around 110 people, all working at the same site. We only allow remote as an exception. We’ve had several internal discussions about having people remote, but we are afraid that it could severely impact our culture. I, personally, have difficulty in imagining our culture without us being present, seeing and touching each other.

So my question to you is: How do you foster healthy bonds with remote people, to whom you have never given a handshake, a kiss or a hug?”

Sara’s Answer:

Having a strong company culture is an absolute must for the long-term health of a business, so questions about how to maintain and nurture a culture that includes remote workers is a very justifiable and common concern. The culture of the company needs to be creatively extended to your remote workers – who will be more engaged and productive if they really feel like part of something larger.

Healthy bonds are developed in a respectful, open, communicative, and trusting environment where people feel valued and heard. Everyone doesn’t have to be in the same building to make that happen.

Like so many other parts to making remote work successful, it does require intention and thoughtfulness. When starting FlexJobs as a remote company, I was very conscientious in considering how I could translate the best “traditional office” elements and activities to a virtual environment.

Some of the ways we’ve done this have included:

  • Virtual coffee breaks with each other, when we turn on our videos and have “watercooler” chats (no shop talk allowed!)
  • Virtual lunches (sometimes we’ll order pizza to everyone’s house)
  • Desktop yoga classes with one of our team mates leading on video
  • Virtual Happy Hour trivia on Friday nights after work, and
  • Virtual team celebrations, such as baby showers which we’ve done for expectant co-workers by sending gifts in advance (optional) and/or treats

Halloween is a really fun example of our remote culture in action, and The Atlantic even did an article a few years ago on “The Rise of the Remote-Work Holiday Party” which included us in it. Many brick-and-mortar companies often have a big bowl of candy in the office and sometimes people even dress up in costumes. For us, we have translated that into finding out which candies each person on our team likes (which we do during on-ramping), sending out Halloween care packages so everyone receives treats in the mail, and even having video meetings in our Halloween costumes! This is a light-hearted example, but you’d be surprised at how excited and appreciative people are of these gestures. Just by considering people’s preferences, putting in some effort, and encouraging people to celebrate and enjoy, we are able to convey our company culture in the remote environment. Plus, it helps to avoid some of the feelings of isolation or disconnect remote workers might feel.

Other ways to help remote workers feel more connected to your culture could be occasional meetings or visits to the office or even creating an Employee Resource Group for your telecommuters, by your telecommuters. Remote.co, FlexJobs’ sister site, has a great article, “Building a Healthy Remote Company Culture” that you may want to check out. Even though this content focuses on 100% remote teams, there are ideas in here for hybrid companies to use as well.

I hope you’ll consider formalizing remote workers as a part of your overall strategy! Companies with remote workforces (both the hybrid model with in-office and at-home workers, and completely remote workforces) see benefits like reduced turnover, improved productivity, reduced real estate and operating costs, a lowered carbon footprint, a larger talent pool to find highly-qualified hires, and more satisfied workers.

And it’s very important to keep in mind that, for some professionals, remote work is the only way they’re able to work: that includes people with disabilities or health issues, military spouses, parents, primary caregivers for elderly parents or health-challenged family members, and others.

Written by Mandy Moore

Operations Manager at Know Your Team. My goal is to love what I do every single day. Follow me on Twitter at @therubyrep.

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