Hiring Remote: CEOs and Entrepreneurs Share Their Knowledge

Jake Woehlke
RunningRemote
Published in
8 min readMay 17, 2018

The new workforce is going remote.

“According to the temp industry, workers were just another capital investment; only the product of the labor had any value. The workers themselves were expendable.”

-Lisa Mills

Whether its temporary remote work agreements for a day away from the office, or a full-time job with no cubicle in sight: a growing number of companies, CEOs and entrepreneurs are recognizing the importance of finding and managing great talent wherever it may be. In the past, “…workers were just another capital investment; only the product of the labor had any value. The workers themselves were expendable.” This according to Erin Hatton of the New York Times.

Running Remote 2018 Conference

Today, remote work entrepreneurs and CEOs are sharing that knowledge with the eager attendees of Running Remote; a conference dedicated to teaching the elements of managing a robust remote workforce. We caught up with some of the speakers beforehand to ask them to share their best advice on remote work:

On Hiring

First, managers hiring need to put in the effort, both in the hiring and in the process after that. When selecting potential remote hires, “Don’t hire remote unless you’re willing to put in the effort to make remote working a first class citizen in your organization. That means investing in communication workflows and processes. You’ll feel like you’re over-communicating every step of the way but you have to do that to make remote work work.” (Wade Foster, CEO and co-founder of Zapier)

Recognize that “working remotely is a skill like any other, and it’s naive to think that a good developer will necessarily make a good REMOTE developer. Hire people with experience working remotely or running their own business.” Experience counts when you are looking for the right remote candidate (Alex Turnbull, CEO and co-founder of Groove)

Approach hiring from a different way. Giacomo ‘Peldi’ Guilizzoni, the founder and CEO of Balsamiq uses a “blind” approach when hiring remote workers: “We… …usually skip the initial CV step and go straight into a long and detailed online form to fill in. This has the benefit of filtering only those people who really want to work for you, going through the painful process of answering all the questions. Another benefit of this “blind” approach (as you won’t know age, race or even the applicant’s sex sometimes) is that you’ll have to base your filters on the candidate’s answers, instead of giving in to the human flaw of preferring people who look like you.” Along the same lines, Andrei Soroker (CEO and co-founder of Sameroom) believes that the old “CV” way of hiring isn’t working. Instead, he offers applicants “a homework assignment that fits the position and decide(s) whether you want to dig in based on the results. Remember that when hiring remote you don’t really care about the “culture fit.””

https://medium.com/@scotthelmes

Find people who work well on their own; self-sufficient employees do not need to be managed as intensely as others. “Seek for people that are self-managed. After all, you have the whole world at your disposal to hire. Favor self-managed people at foreign time-zones over people close to your time zone that you need to micro-manage.” -Pablo Hoffman, co-founder of Scrapinghub

Ask questions before you hire; the answers your potential employees give can provide valuable insights into both the applicant and the market. Ben Welch-Bolen, CEO and Co-Owner of World Wide Web Hosting, finds that asking questions of his applicants helps to establish standards and expectations of the job itself: “It is hugely important that you ensure people don’t need an office environment and have a strong support group outside of work. Once we tweaked that in our hiring process our employee retention skyrocketed. How do we do that? We ask questions to make sure they understand the social elements of work will be missing and that they have family friends and robust hobbies out of work they can pursue.” On a similar note, Alice Hendricks (CEO of Jackson River) encourages potential remote team leaders to have “a very open and honest conversation about working remote — set clear expectations of what is expected and understand how the employee works best. Clear and open communication about working remote is key.”

On Managing

When managing a remote team, certain elements are key to making the experience a successful one. However, one component in particular was endorsed by all: communication.

“Create and encourage a culture of openness and communication. Go out of your way to make sure everyone on the team understands business, functional and project priorities. Make sure to solicit ideas and perspectives from everyone in the organization. Never let anyone feel left out.” -David DuPont, President and CEO of TeamSnap

Constant communication is also an important piece of the remote team management experience: “Over communicate. Over communicate. Over communicate. Use many forms of communication for your team, both real-time synchronous communication like phone calls and video chats, and asynchronous communication like email and messaging platforms. Don’t be afraid to repeat yourself. Did I mention to over communicate?” -Jody Grunden, Managing Member and Virtual CFO, Summit CPA Use the right tools to enhance the communication, and add some physical meetups with co-workers when possible, this according to Robert Glazer, Founder and Managing Director of Acceleration Partners: “We’ve found that frequent communication produces higher levels of employee engagement. We use video conferencing for many of our internal meetings so people can make a personal connection with their team members. We also host bi-annual company meetings so they can get to know each other in person.”

Because a remote team cannot inhabit a conference room every Monday morning, our CEOs and entrepreneurs advocate finding (and utilizing) the right communication tools and platforms to help your team grow and function together:

  • “Use great communication tools. We obviously love using iDoneThis for asynchronous team communication. We love Slack as well.” -Walter Chen, Co-Founder and CEO of iDoneThis
  • “Have and use an online project management tool. Keep expectations documented and transparent. The remote employees may miss context or expectations by not being in the office, having side conversations, and missing some of the meetings that you’re in. You can resolve this by keeping milestones, due dates and tasks clear and documented in an online project management tool.” -Seth Viebrock, Founder and CEO of Origin Eight
  • “Use a couple of tools that work for everyone and try not to overdose on the rest. At Ghost this means Slack for all our communication and Asana for all of our project management.” -John O’Nolan, CEO and Founder of Ghost
  • “Without tools like Slack and Time Doctor, managing remote teams can get very messy.” -Andrew Ruditser, Co-Founder and CEO of Maxburst
  • Gary Kanfer (from Big Drop Inc) advocates using time-tracking software: “We can see if they are putting in the hours that they said they would do.”
  • Running Remote speakers also advocate time tracking software TimeDoctor for their teams. ““Since we started using Time Doctor 3 years ago, we have increased revenue 1000% as a business.” -Luke Sartain, LSG Creative. “If clients dispute the work, Time Doctor enables me to prove the work was done. The best part is being able to track the exact time that was spent and relaying costs back to the customer.” -Adrian Barber
  • “15Five identifies and resolves cross-team issues, stimulates design discussions, fleshes out inefficiencies and averts mistakes. It illuminates individual achievement and brings forth many good ideas.” -Eric Raab

Of course, sometimes too much is too much. That is why Nathan Gilmore (Co-Founder of TeamGantt) advocates management of communication to increase focus and productivity: “Try to reduce as much unnecessary IM Slack chat as possible. One of the best perks of remote work is the extended periods of focus that can’t be achieved in a busy office. If everyone is “Slack”ing off or using IM a lot then the real work can’t get done. We try and do as much of our communication through email and TeamGantt. This way I can work for a few hours then when I’m ready for a break I check my email or TeamGantt to see what people need from me.”

The 2018 Running Remote Conference Main Speaker lineup

Utilizing communication and the right tools with a remote team, the remote team manager can also foster collaboration and engagement across team members, time zones and cultures. “Develop a rapport with them via IM conference calls and one-on-one Skype chats (video or audio-only). Also help them feel engaged — we do this in a variety of ways. For example our CEO holds an all-company meeting via conference call every two weeks. Many of our teams have short production or “stand-up” meetings each morning.” (Chuck Vadun, Communications Director at Fire Engine RED) Also, “Have a regular video call to assess how they’re doing — it’s important to have face-to-face connection.” (Leah Mason, Director of Operations at Four Kitchens)

“Create a culture of collaboration supported by the right tools and processes so that you can still get the ‘water cooler effect’ even if people aren’t just down the hall.” -Govind Davis, CEO & Chief Architect at MCF Tech

Along the way, make sure to be present for your team. “As a manager or remote supervisor you must continually remind your staff that you are available. You don’t need to be available 24/7, however you need to be “seen” in the office on a regular basis through a chat program (i.e. Google hangouts, Facebook chat). Staying in touch virtually is vitally important when you don’t see your staff face to face often.” -Jimmy Walicek, CEO and Co-Founder at WAKA Kickball & Social Sports

You’ve established a culture of communication, utilized tools to foster that communication, and encouraged engagement among your remote team. What comes next? Find a way to make “sure that they have enough to do to feel productive and for you to measure productivity. It doesn’t matter when they do the work (for most positions) it matters that they’re getting it done. Incredibly efficient people tend to gravitate toward successful remote work. If they get 120% of the average productivity done in 5 hours a day… do you care? No, you don’t. Don’t micromanage your best people, otherwise they’ll find someplace else to shine eventually. (Aaron Bright, M.D., Co-Founder and CEO of Hippo Education)”

Finally, remember what hiring and managing any team (remote or otherwise) is all about: results. “Employees are accountable and autonomous and are free to work when, where, and how works best for them, as long as results are being achieved.” -Lindsay Goodine, Director, Culture and Development at ICUC

The experts speaking at Running Remote come from different backgrounds, work in different industries, and run different teams. However, one thing is for certain: they are among the first to recognize the importance and value in engaging the new remote workforce, and these workforce trailblazers will be in Bali in June to help you. Join them, and join the remote work revolution.

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Jake Woehlke
RunningRemote

Creator, marketer, and support consultant taking time to become a financially independent digital nomad. Come wander with me. // jakewoehlke.com