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Article 6 min read

Startup Central — The human guide to leading remote teams

WFH is here to stay. In this guide, we talk to startup leaders about how they're facilitating productive, human collaboration from anywhere.

By Sammi Chen, Startup Marketing Associate

Last updated January 13, 2021

At this point, most people’s social media feeds have already been flooded with work from home guides and tips. But many of these resources glossed over an important aspect of working from home: the human factor.

The Zendesk for Startups team talked to Liis Saar, Director of CX Tools & Systems at FabFitFun, Max Yoder, CEO and co-founder of Lessonly, and Lindsey Kugel, Director of Partnerships at Search Inside Yourself Leadership Institute (SIYLI) about the messy, human reality of remote work, and why keeping it real is so important. Here’s what we learned.

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Key learnings

  • Create watercooler moments. This kind of friendly banter builds relationships, it gives people a much-needed sense of connection with coworkers.
  • Stop putting perfectionism on a pedestal. The times when leaders are vulnerable and human are the times when they get the most support.
  • Give your people props. People like being acknowledged for the good work they’re doing, especially during tough times.
  • Ask questions, share feedback. Talk to your team, and don’t assume your colleagues know something just because you know it.
  • Learn the answer. Leaders should not be expected to have the answer to everything, but they can learn the answer through collaboration and discovery.
  • Make time for life. Even if it feels like there’s not much to do right now outside of work, we should still unplug and unwind.

Create watercooler moments

It’s time to unlearn the idea that taking extra time to schedule catch ups with coworkers is a waste of time. Mixing work time with personal time may look like a burden, but in reality, it greases the wheels needed to get things done as a team.

When someone is having a human moment, people support them. When a level of trust is established, the hesitation to reach out to a team member for help is reduced.

“Building personal relationships feeds into the sense of comradery. It’s easier for someone to pick up the slack if needed or work together and be more productive as a team,” says Kugel.

Watercooler moments are important, a normal day at the office includes casual interaction and side conversations that break up the day. This kind of friendly banter not only builds relationships, it gives people a sense of what’s going on in the company and what everyone else is working on.

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Stop putting perfectionism on a pedestal

Human beings are vulnerable. We crave comradery, interaction, and appreciation to keep us motivated and moving forward. At the end of the day, we’re not perfect. We make mistakes as we learn and that is what makes us whole and who we are as individuals.

“Perfectionism is a plague of modern culture. Perfection forces us to hide the parts of ourselves that don’t map to a perfect thing. It forces us to reject that we’re human,” says Yoder.

“Perfectionism is a plague of modern culture. Perfection forces us to hide the parts of ourselves that don’t map to a perfect thing. It forces us to reject that we’re human.”
Max Yoder, CEO and Co-Founder, Lessonly

“The alternative to perfectionism is wholeness,” says Yoder. Being able to acknowledge that people have qualities that are average, below average, and above. Self-awareness supports the wholeness of the organization. Being vulnerable makes a person relatable. The times when leaders are vulnerable are the times when they get the most support.

“Effectively, wholeness is saying I am a human, therefore I will do human things. I will forget things. I will interrupt, and I can apologize when I do it. I will be a full person and I’m not ashamed of it,” says Yoder.

Give your people props

Appreciation rounds and positive feedback all lead to an increase in morale. People like being acknowledged for the good work they’re doing. A pat on the back (even if it’s a virtual one) goes a long way.

“It’s a way of getting all the feel-goods, and finding out the things that are going on because someone is being appreciated for what they’re doing, a project that they’re on,” says Kugel.

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Ask questions, share feedback. Rinse. Repeat.

There’s never been a better time to overshare. Sharing before you’re ready is encouraged and helps clarify doubts around a task.

Beware the curse of knowledge. “If I know something, I assume you know it too, which means I’ll under explain and leave out important details when I talk. If we know that it’s human bias, then it’s our responsibility, not just a nice to have,” says Yoder.

The feedback loop is crucial to understanding. It makes people feel empowered and useful and teaches us that there is more than one way to get something done.

Learn the answer

Good leaders learn. Effective leaders know that simply reading something doesn’t change behavior. In order to really learn, we have to take what we’ve read and apply it, which is done through practice.

“We should remember that leaders learn the answer, and there is a difference between learning the answer and knowing the answer. Leaders learn the answer by balancing some level of certainty and uncertainty. We’re certain we can get something done, we just don’t know how yet, ” says Yoder.

Make time for life

One of the biggest challenges of working remotely is managing a healthy work-life balance. We no longer have a commute to break up the start and end of the workday and being constantly connected can cause boundaries to blur.

A lot of people are pouring themselves into work, so we have to be clear and persistent around the message that ‘you have to take time off.’

“A lot of people are pouring themselves into work, so we have to be clear and persistent around the message that ‘you have to take time off’ just like you would take time off in normal times. There’s nowhere to go but that doesn’t mean that we can’t be unplugging,” says Yoder.

The shift to digital has accelerated more in the last ten months than it has in the last ten years. These shifts have forced us to adapt the way we communicate, especially as managers and leaders.

But a packed Zoom meeting doesn’t have the same energy as a packed office, and we’re beginning to understand the importance of communicating often and effectively. And remembering to remain human should be at the core.

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