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How Successful Remote Teams Evaluate Employees: A Look inside Automattic, GitHub, and Help Scout

By Jeremy Duvall · April 1, 2019

During my first full day of work at Automattic, the only thing running through my mind was "Am I going to get fired?"

That's an unusual feeling, especially when you're hours into a new job. To clarify, this had nothing to do with Automattic or any of my coworkers. They were all friendly and welcoming, encouraging me to take my time getting adjusted to my first remote position.

Still, I had this lingering fear in the back of my mind: I was used to seeing my coworkers and supervisors on a daily basis, and using in-person skills to feel out how I was doing. Now, I was missing those seemingly crucial cues, and that made me fear the worst.

I was suffering through Imposter Syndrome—the feeling that I was a fraud, that I wasn't worthy of my position, and that sooner or later, someone was going to find out.

I had a sneaking suspicion that I couldn’t be the only one who felt this way. After interviewing leaders at established remote teams, my suspicions were confirmed: This feeling is largely normal. "The struggle is real. Those first few days working remote seem so awkward, and you'll spend at least 10% of your time wondering if you're doing the right thing," confirms Greg Ciotti, Content Marketing Lead Shopify and former marketer at Help Scout.

So I started thinking: Is there any way to prevent Imposter Syndrome in remote teams? And what's it like for managers who need to evaluate these conflicted remote employees? Here are some best tricks of the trade from companies like Help Scout, GitHub, and Automattic.

Make New Teammates Feel Welcome from the Start

Remote environments can be intimidating for new employees, particularly if they’re coming from a traditional, co-location office setting. One practice that helped me early on at Automattic was having a veteran employee as a "buddy" to help me navigate the uncharted waters.

I'm not alone in my desire for camaraderie in remote workplace. Ciotti recommends the buddy approach to help new employees feel welcome. There’s even science indicating that employees who have friends at work "get sick less often, suffer fewer accidents, and change jobs less frequently."

Ciotti offers five tangible takeaways for buddies paired up with new employees:

  1. Shoot the new employee a quick email before they start to welcome them to the team. Don’t use email? Slack or any other communication tool will work.

  2. Offer to be available for any random questions—even the ones that seem silly. (Speaking from experience, new people tend to hesitate on asking genuinely important questions.)

  3. Check in with them on your team's chat app every couple of days in their first week to see how it's going. (My buddy and I checked in with each other once every two weeks, always on a Friday.)

  4. Tell them about your team retreats or what it's like to hang out with the team in-person. (In my case, my buddy and I chatted about "Grand Meetups," the annual all-person gathering at Automattic.)

  5. Share some "unwritten rules" like the difference between the #general and #offtopic communication channels in Slack. (Similarly, my buddy enlightened me on Automattic's #BurritoFriday tradition.)

Above all, buddies should make new employees feel comfortable and act as a go-to for questions employees might otherwise feel embarrassed to ask.

Measure Output, Not Input

Matt Mullenweg, CEO of Automattic, has some strong doubts about the normal 9-to-5 grind. "If someone shows up in the morning dressed appropriately and isn’t drunk or asleep at his desk, we assume he's working. If he's making spreadsheets and to-do lists, we assume he's working really hard. Unfortunately, none of this gets at what an employee actually creates during the day," Mullenweg says in a Harvard Business Review post.

One potential solution to this conundrum? Have managers hover over employees either by roaming up and down the aisles in a traditional sense or obsessively checking to see when someone logs in or out. According to Ciotti, that's the shortcut to burnout:

Fires only burn when they have room to breathe, and you’ll end up suffocating enthusiasm, motivation, and camaraderie by looming over people all day, every day.

Instead, productivity at Automattic is measured by output, not input.

"At Automattic we focus on what you create, not whether you live up to some ideal of the 'good employee,'" explains Mullenweg. For developers, that might mean looking at how many commits they’ve had over a given time period. For the support staff, that could be total number of tickets answered. The underlying message is to find a metric outside of hours spent to evaluate productivity.

Look to the Team for Feedback

When gathering employee feedback, it's crucial to remember that the relationship isn't just between supervisor and employee. Each employee has a string of relationships with their fellow co-workers. Phil Haack, software coach and author, said he heavily relied on this team atmosphere to evaluate performance when he was an engineering manager at GitHub. He explains that when you create a strong team, it's easy to see who isn't pulling their weight.

For performance reviews, Haack asks each employee to send him a list of three to five co-workers they would like peer feedback from. He then asks those co-workers to provide feedback for the individual in three categories: Start, Stop, and Continue. Each box should focus on behaviors that match the title (behaviors someone might want to stop, for example). Haack adds the boxes aren't mandatory. "If you have three categories, the temptation is to put something in each. You might not feel very strongly that someone needs to stop doing something." In that case, employees can just leave a box blank.

Haack takes those bits of feedback and distills them down into major takeaways, combining duplicates and making sure feedback is worded in a useful manner. The end result is a collection of behavior-based feedback from individuals you work with daily.

Two elements are crucial. First, the format (Start, Stop, and Continue) provides a framework that makes a difficult task (giving peer feedback) easier. The main purpose is to help employees organize their thoughts. Second, the feedback should be focused on behaviors, not personalities. The former is something an employee can improve; the latter isn't.

Ask for Self-Evaluations

When performing a review, Haack considers three points of view:

  1. His own opinions.

  2. Thoughts from co-workers.

  3. A self-evaluation from the actual employee.

Self-evaluations often get a bad rap. As professional relationship author Keith Ferrazzi explains in an article on Harvard Business Review, employees tend to fall in one of two traps (potentially both). First, they become a victim of the Overconfidence Effect, which causes them to overestimate their competence in a given area. Second, they’re likely to make a Fundamental Attribution Error, pinning their successes on talent and wisdom while failing to acknowledge environmental factors.

To combat this, Haack uses all three points of view. The goal of the self-assessment isn't just to see how great everyone perceives they are, but rather to see if the three points of view match up. "The point of that was to help me understand how people saw themselves, how others saw them, and how I saw them and see if there's a big disconnect there," he explains.

Self-evaluations have their flaws when used as the sole assessment method. However, in conjunction with team reviews and the opinions of the team leader, they help to complete the 360-degree view. They also reassure employees that their voice is being heard.

Provide Feedback Often

"I spent a lot of the six months hoping I didn’t get fired." That’s not something you want to hear from one of your employees, but it’s a real conversation Haack had with someone during their first official feedback session.

If employees are more familiar working in an office environment where they receive feedback daily, the silence in a remote position can be the perfect breeding ground for Imposter Syndrome. It's easy to assume the worst about your work when you don't hear otherwise.

Everyone I spoke with for this chapter emphasized the benefits of giving regular feedback outside of formal reviews. Why? Because regular feedback lets employees know where they stand, gets everyone on the same page, and reduces the chance of a surprise during a more formal review.

When Haack was at GitHub, he had regular one-on-one meetings with his distributed team (they live all over the world) using a video conferencing software called Blue Jeans. At Help Scout, team leads have scheduled weekly reviews with everyone in their department. They chat about what has gone well since the last check-in and what's looming on the horizon.

Regardless of whether you check-in with employees daily through a chat app, schedule weekly video sessions, or meet in-person monthly, the key is to provide continuous feedback rather than combining it all into one surprising review at the end of the year. Ciotti does offer one important caveat, "We hold the opinion that you should share praise and own blame." Hold performance-oriented discussions in private, not in public.


One common thread that runs deep across every method of managing a remote team: trust. Employees need to trust that their managers are looking out for their best interest. Managers need to trust that their employees are engaged and motivated at work. Part of this trust is built during the hiring process—selecting candidates who are self-motivated—and the rest is built over time with each positive interaction.

Just like in-person office cultures, remote office cultures can differ wildly.

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