How to Adapt: 7 Tips from Upwork’s Former CEO

  • By Maddie Rosenthal
  • 22 June 2020
“Upwork has maintained a hybrid remote-working structure across 500 cities for 20 years. It’s a part of the company’s DNA.”

In case you missed it, Tessian hosted the world’s first Virtual Human Layer Security Summit on June 18. While the majority of presentations, panel discussions, and fireside chats were focused specifically on how the sudden transition from office to home impacts cybersecurity, a few speakers touched on the new world of work more broadly.

One of those speakers was Stephane Kasriel, Former CEO of Upwork.

For context, Upwork has maintained a hybrid remote-working structure across 500 cities for 20 years. It’s a part of the company’s DNA. The point? He’s in a better position than most to offer advice on how to adapt and overcome the challenges that come with distributed workforces.

While you can watch his interview with Tessian Co-founder and CEO Tim Sadler below, we’ve summarized his top 7 tips. 

1. Lead with empathy.

The Golden Rule.

Above all else, Stephane recommends leaders treat others the way they want to be treated. While it may seem obvious, it’s an excellent reminder, especially now as our employees are grappling with so much fear, anxiety, and stress around the pandemic and other triggering social and political issues. Put yourself in their shoes and identify the tools, resources, and support they need to thrive. 

“This is not normal remote-work. People may be sick, they may be scared of being sick, they may have people close to them who are sick, they may have children at home, they may have multiple people on Zoom at any given time and not enough bandwidth to connect. Rule number one is empathy. This is a tough time for everyone and leading with care and love is one of the best things we can do.”
Stephane Kasriel Former CEO of Upwork

2. Err on the side of over-communication.

Let’s face it, communicating is often easier in-person. That’s why it’s so important we over-communicate when working remotely. 

How? Repeat yourself, touch base frequently over Zoom or Slack, share minutes post-meeting, schedule frequent catch-ups with people outside of your immediate team, and never assume people know what you’re thinking. 

3. Take advantage of a global talent pool.

One of the most compelling arguments in favor of remote-working is the diverse talent pool recruiters suddenly have access to.

Whereas traditionally, we’re forced to employ people who live near offices or headquarters, remote-working structures allow organizations to find people who are truly passionate about their work and who are aligned with company values. 

Importantly, this isn’t just a benefit for employers. It’s a huge bonus for employees, too. Many of us opt to live in major cities because, well, that’s where the jobs are. If given the choice, we’d forgo higher-than-average costs of living and relocate to work online and out of the office. Win-win!

4. Be considerate of time zones and working hours.

Whether your entire team is based in the same region or you have employees dotted across continents, business and security leaders must be considerate of time zones and working hours. 

We simply can’t expect people to be available and online 24 (or even 12!) hours a day, especially now when people are working hard to balance the needs of children, roommates, partners, and even parents. 

That means switching from a very synchronous model where everybody’s online at the same time to something that’s more asynchronous. Take advantage of tools like Loom, encourage employees to use email, Slack, and other channels, and implement sign-off processes that are smooth, regardless of where and when people are working. 

Looking for more collaboration tools? Check out this blog: 11 Tools to Help You Stay Secure and Productive While Working Remotely.

5. Measure success based on facts specific to your organization, not headline statistics.

Most of us have read at least one headline around how employee productivity is lower when they’re working from home. If you ask Stephane, this simply isn’t true. At least not in Upwork’s case.

“There is no data that shows that worker productivity goes down when people are working remotely. In fact, there’s tons of data that shows the opposite,” he said.

Remote working doesn’t just improve productivity. It boosts retention. Stephane says that people who work remotely stay with the company twice as long as the people who are based in the HQ locale

The bottom line: what works for some may not work for others, and vice versa. Measure success within your own organization to see what works for you and your people, not for everyone else.

6. Ask for, listen to, and document feedback.

It takes a village to be successful and diverse opinions are needed for businesses to thrive. 

Ask your employees how they feel about company culture, policies, procedures, and their workloads and heed their advice. While you may not be able to action all of their feedback, ensuring that they feel heard will help bolster a sense of community.

At Tessian, we use Peakon to track and document employee satisfaction. What do you use?

7. Stay agile.

The outbreak of COVID-19 has catapulted us into the future.

“The sobering fact is, the virus has done more in three months than I've been able to do in 10 years. We've really gone into the future in a big way. I think what really matters here is to understand what's working, what’s not and fix it quickly.”
Stephane Kasriel Former CEO of Upwork

Adopt new technologies. Embrace new ways of working. Lean on peers and professional networks for advice. 

Fortunately, there are plenty of trailblazers who have done some of the hard work for us. Upwork, of course, is one and they’ve put together an incredible content hub for business leaders with advice around building and managing remote teams. 

Looking for more resources? Tessian has also created content hub with advice for security, IT, and compliance leaders. This includes information about BYOD policies, Data Loss Prevention (DLP), and how to spot COVID-themed phishing attacks. Check it out!

Maddie Rosenthal