5 Tips for remote work success from the founders of PowerToFly

This is Part 2 of our Q&A with Katharine Zaleski and Milena Berry, co-founders of remote work platform PowerToFly. In Part 1, Zaleski and Berry shared their observations about why remote work is on the rise. Here they offer their tips for creating a successful remote work relationship.

1. Use daily reports

This is essential—and the first and most important rule for operating remotely. Being transparent about what you’re working on helps everyone know where they stand, prevents overlaps and miscommunications, and allows managers to make quick agenda fixes when necessary.

2. Give feedback: “Bad news is better than no news”

This idea came from “The Hard Thing About Hard Things” by Ben Horowitz. It’s one of our favorite books because it stresses how you should never sugarcoat feedback. Employees suffer because they are deprived of an opportunity to improve, and employers are hurting their companies in the long run by letting problems fester. Positive feedback is equally essential. Let your employee know when you are happy with their work (ideally face-to-face, using video conferencing). Otherwise they have no way of knowing whether they’re meeting the mark.

3. Escalate the medium, not the message

With any contractor, or boss, confusion can set in when you don’t meet at a formerly agreed upon time. If email isn’t reaching them, then you try something else (chat, video, etc.). The same should apply in a remote relationship. We provide talent and clients with multiple points of contact so that they can take another approach when emails aren’t going through. Remember, it’s always better to try a different medium than to send another annoyed email!

4. Schedule a one-on-one

Just because you aren’t physically together, that doesn’t mean you can’t meet (virtually). At PowerToFly, we make sure that direct reports have at least one weekly video call or voice call each week. This allows us to hear any issues that can’t be interpreted via email or group chats. It’s also a great way to get team members to suggest improvements that they’re scared to formalize in email messages or in front of others.

5. Make sure the sun never sets on you

One of the advantages to staffing remotely is that the sun never sets on your company. At PowerToFly, we work twenty-four hours a day because teams are spread out from New York to India. Time zone converters keep us in check when we’re about to call a teammate who is deep into a REM cycle. Our favorite tools are World Time Buddy and Time Zone Converter. We also use a Google spreadsheet to keep track of who is online at what time.

More tips on staying connected

At Highfive, we’re focused on enabling companies and people to work from anywhere while staying connected face-to-face. For more tips, check out this post on how to stay connected while working remotely from one of Highfive’s own remote workers.

Leaving the Office Behind: A Guide to Remote Work


How employees and managers can build the best culture for remote work

Whether you’re a work-from-home employee, frequent traveler, or manager in charge of distributed teams, you need the right setup and the right tools to make remote work effective. This guide covers the the dos and don’ts to help you build a successful remote work culture.

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