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The age of remote work: Experience and best practices for working remote

Hi Community,

A question(s) that has been top of mind is around remote work in a changing workforce. I have been at two businesses that have varied in this approach. One with a 'No remote work allowed' policy while the other business was 100% remote.

How do you approach hiring, working with, and managing remote employees?

What is your personal experience in managing, or working, remote and best practices to maximizing productivity and communication?




  • edited July 2019


    I'm a remote employee on the PI direct sales team. I can speak to your last question around best practices for maximizing productivity and communication. It might make the most sense for me to describe the ways my managers have best empowered me throughout my remote experience. Keep in mind, my behavioral pattern (Maverick) is kept top of mind in the approach my managers take toward keeping me productive and connected.

    1. TRUST -- I cannot stress this enough. I am remote because I know I don't need constant oversight to take care of my own work. Freedom from micromanagement, ironically, motivates me more than an email from my manager telling me to get my job done. Like many Mavericks, I'm 100% comfortable taking responsibility for my failures and my successes and I'm more motivated to get something done quickly if I feel like I have the autonomy to do it on my own time.
    2. Clear definition of responsibilities and check-ins for accountability. Ex: In the places I'm liable to fall short (detail, process), it helps me to have very clear expectations so that I don't wander off unconsciously. Plus, a concrete, weekly check in provides ample opportunity for me to voice anything I need to express.

    Would love any follow up questions -- this is something I could talk about for days!


  • @Thad Peterson and @Shannon Howard - your perspectives would be great to have here.

  • Hey Steve,

    Such a great question! As a remote worker myself it took some adjusting to when I first started. For me tools like Slack and Zoom have allowed me to still feel like apart of the team and allow me to talk or ask questions in real time.

    As far as productivity goes the key is being able to block off specific times on my calendar to do what I need to accomplish for the day. It really helps when you know how long each task is going to take and can plan accordingly.

    The part that I personally struggle with is taking breaks through out the day so that I am not working all 9 hours of my work day.

    Thanks again for the great post Steve!

  • Hey Steve!

    Great question—thanks for asking!

    I'm currently the only full-time remote employee on the marketing team at PI. I've been working remotely for ~6 years and used to manage a remote team of 25 employees. Not saying I have all the answers or that this is going to work for everybody, but hopefully some helpful insights!

    Some As to your Qs:

    How do you approach hiring, working with, and managing remote employees?

    Hiring: Personally, I look for people by referral. If you've got good people, they probably know more good people! But when it comes to hiring someone who's going to work remotely for your team, you want to check in on a few things:

    • Have they worked remotely before? (Pry deeper - was it successful?) You don't want your first remote hire to have no remote experience. That's setting you both up for failure.
    • Ask about their home office setup. Do they have roommates? Loud noises? Do they have a noise-canceling headset. You want to make sure there are limited distractions—not just for this employee, but for everyone who will be working with them.
    • How do they hold others accountable virtually? One of the biggest obstacles for remote workers is the inability to walk down the hall to have a conversation. What do you do when you need an answer and no one's responding? The ability to be assertive goes a long way here.

    Working with: The book "Remote: Office Not Required" by the founders of Basecamp is a great (albeit old) primer on remote work. The technology is set up for remote work to be successful. The biggest hurdle is the mindset I wrote about in this blog: Many people will assume you're partying in your PJs, because that's where their understanding of remote work is at. Transitioning your team to include remote employees means a reconditioning of what it means to work and how performance is measured. Work-from-home employees are measured by results, not by hours. Contrary to the belief that most WFH employees are slackers, most WFH employees actually work longer hours because there's no physical separation between work and life.

    Managing: Ian nailed it with trust. You have to trust you hired smart, capable people who will get the work done. Otherwise, why did you hire them? My advice to remote managers is to be super intentional in reaching out, scheduling regular check-ins, and providing updates. Remote team members don't have the privilege of passing-by conversations, so they're often out of the loop. In alignment with the "working with" problem, this requires a change in how communication is done. In most office settings, communications happen informally (aka in person). As a result, there's often no record of decisions made or conversations had. If any part of your team is remote, be intentional about summarizing meetings, conversations, and decisions and recapping by email. This provides the added benefit of a reference point, should anyone have questions or confusion about what was communicated.

    What is your personal experience in managing, or working, remote and best practices to maximizing productivity and communication?

    I can't state emphatically enough: I think more companies should be making this transition. It saves on overhead costs, allows people to be more flexible with their work, saves on commute time, and allows companies to make hires who may not want to live in a city or be able to afford city living. I also think it helps us challenge things that are status quo in the workplace but ultimately aren't effective, such as out-to-drinks decision making that excludes more than just remote employees, making decisions that aren't documented in writing, and side conversations in meetings. (As I like to remind people: Microphones don't pick up the main speaker. They pick up sound.)

    That said, it takes tremendous effort—on the part of the employee and the company. We don't realize how conditioned we are to work in a physical work environment until the ability to stroll up to someone's office is removed. At that point, you realize digital communication is your only option, so you learn how to use it well. It's a big change for folks.

    And, as Thad pointed out, when you're the minority, it's even more difficult. You have to be more assertive than maybe you're naturally wired to be to make sure people respond and spend time educating folks on the remote experience. Remote employees also naturally have less visibility, making it easier to pass them over for promotion or special projects. If you're a remote worker, you have to constantly advocate for yourself.

    For those who think that working remotely means you can't build relationships, I'll say this: When my husband and I eloped, my teammates were our witnesses. Last year, I officiated a wedding for one of my former employees. Just today, I had a phone call with my old admin just to see how things are going and provide career advice. Just because you're at a distance doesn't mean you can't have great personal and working relationships. As with all relationships, you have to be intentional.

    At PI, Slack makes it relatively easy for remote and in-office employees to connect in real-time, have casual conversations, and share fun stuff. At my old company, we had a group text thread that kept us constantly in touch and building personal relationships.

    Alright, I could go on and write a novel over here, but I think those are the most important points. Feel free to tag me in any questions!

  • My husband has been working remote for the last couple of years. He LOVES it.

    1. He's an introvert.
    2. His leader has set very clear expectations.
    3. His team has a communication rhythm that allows him to connect on a regular basis.
    4. Everyone on the team is available to brainstorm and think through issues on an ad hoc basis.
    5. He has a 1:1 with his lead every week.
    6. And he has a 1:1 with the big boss on a monthly basis.

    I've never seen him happier and more enthusiastic about his team in the 25 years we've been married.

    He gets more done. He has a ton of support. And the company doesn't have to pay for floor space.

    win. Win. WIN.

  • That's awesome to hear @Tammy Rogers And great to hear about the specifics that make it work so well. Out of curiosity, are there are lot of other remote folks on the team or is it just him? Also, out of curiosity, what kind of role does he have?

  • I'm a huge proponent of working remotely. People tell me that's because I'm a millennial. I think it's because I like freedom and sustainability in my work life. My motivations aside, there is that question of productivity…

    Admittedly, as an entrepreneur/consultant, I'm a well-skilled at being effective without a task master looking over my head (profile = maverick) and also working without the context of an office. Call it focus, crazy, or crazy focus—whatever you want, I just like to get work done efficiently and fast so I can go enjoy life. My motivation is to spend the least amount of time working on things I don't like, while still getting them done satisfactorily. For the record, it's not work if I enjoy it, so I'm also converting as much of my time to sharing those strengths as well.

    Which I think should be one of the many intents behind adopting a remote worker policy—higher job fulfillment, also higher margins from reduced physical plant costs, better lifestyle and more time with loved ones due to lack of commute, enjoying your work life more by increasing your comfort.

    So best practices include:

    • Having bullet-proof integrity—always be on-time to meetings. In fact, adopt a 'on-time is late and early is on-time' approach. This avoids harsh (often unspoken) criticism or judgments from co-workers about your availability.
    • Pay attention to your background—it's like the clothes you wear, it's how you express, and people have to look at it, so make it pleasant and forgettable so that becomes blasé over time. You want the focus to be on you and your contributions, not the contributions of your art deco piece behind in the (keyword) background.
    • Use visuals—often what's missing is a visual thinking element that helps make your conversations come together and aligned as discussions progress. Don't be afraid to share a whiteboard onscreen or shared doc to record where the conversation was, is and will go. As a corollary, agendas are helpful.
    • Leave time for small talk—often what goes missing in computer-mediated communication is the informal 'small talk' element that actually leads to greater context/understanding and perspectives that may not have been considered in the more formal conversation.

    Managing someone remotely can feel a little like micro-management if you haven't established up front what accountability will look like. Have regular check-ins, have a system to record tasks/deliverables/promises and track them against due dates. Distractions abound when working remotely and you want both parties to be on the same page about expected work scope and effort so at the end of the day you can count your successes and shore up any short-comings.

    That said, I still believe business development (i.e. sales) and expanding your business can only happen effectively with face-to-face, in-person relationships (i.e. not remote). There's data to support this, if you're curious. Just PM me for details.

    I hope this helps!

    Matthew Koren

  • @Matthew Koren So grateful to have your perspective. Loved the practical best practices!

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