Interview: Stephanie Lee on Change Management and Transitioning to a Remote-First Approach

Stephanie Lee is the Remote Lead for cargo.one. Cargo.one is a tech company in the cargo air space working to digitalize the process of booking cargo spaces. The cargo.one team is based all over the world and works remotely.

Stephanie is also one of Remote’s top remote work influencers for 2022. As the Remote Lead for cargo.one, Stephanie leads the company’s remote strategy and designs the operating system for the company.

We spoke to Stephanie about effectively transitioning to remote work permanently and the challenges companies might face in the process.

Why do you believe that remote-first is the way to go for companies in general?

So I think remote-first is the way to go for any company that wants to stay agile in the world that we live in. Prior to the pandemic, I had different reasons for saying that, but today I think the reality is everyone’s had a taste of remote work, and a lot of people appreciate the flexibility that comes with it.

As a competitive advantage, it makes sense for companies to have remote work policies. If you want any form of remote work policy to work, it needs to be remote-first. If you’re office-first, it builds in inequities over time.

It’s also more flexible as a business model. You’re no longer limited to a physical space for business operations to happen. This means that no matter what happens, whether there’s another pandemic or an individual employee has a personal situation where they need to work on the road, things can keep going because you’re already optimized for remote work.

It makes complete sense to me for companies to go in that direction. I know a lot of companies are trying out the hybrid model right now. I think for the hybrid model to work, even though that’s the most difficult model, in my opinion, you have to be remote-first.

Why do you say hybrid is the most difficult model to implement?

It’s the hardest model because you need to design your employee experience two levels at a time. If you’re remote-first, you’re only looking at the virtual experience for everyone. In-person events like retreats are integrated into your virtual-first experience.

If you want to go hybrid, then you have to think about both the virtual experience and the physical experience. That’s why I said remote-first is the way to go. If you operate on an office-first basis, your remote people, by virtue of not being as physically present, will lose out.

And I’m talking about things like career progression, participation, and engagement. When you optimize for remote employees, that’s how you level the playing field. The physical experience becomes a nice add-on.

Some leaders worry that if they do not have offices, this will result in a poor work culture. What would you say to them?

It will result in a poor culture if you do not optimize for remote-first. I’m not going to say it’s going to be absolutely perfect, but it’s not inevitable. For anyone who is willing to invest the time and resources into developing a remote work strategy, I think it can really work because the human connection can happen regardless of physical space.

We’re not used to creating connections in a remote-first setting. While it isn’t impossible, it’s very different from the default that we’re used to. That’s why people resist it.

I worked for my previous company for more than five years. I met my colleagues maybe once or twice a year. And yet, some of my closest friends are from that company. I recorded a podcast with a former colleague based in Munich. We recorded and launched 15 episodes. We’d only met twice in real life at that point.

He’s still one of the people I would call if I had questions in a heartbeat. So it is possible to build those remote relationships.

You need to be very intentional, however. I think that’s what the barrier is with some people. They believe that these relationships can only happen in person, but that’s not always the case.

Maybe I drank the Kool-Aid a while ago, but I firmly believe building relationships remotely is possible.

If you think about human relationships, people can have long-distance relationships. They’ll get close to someone and fall in love. That’s not impossible, it’s just difficult.

And no one is saying that it doesn’t have its challenges. When you’re no longer reliant on the physical space to create connections, to get your work done, then it can be quite liberating because then people can find a better balance between work and life.

What challenges do you think companies will face when transitioning to a full time remote-first approach?

From an office-first approach, the challenges are largely twofold. I think the first one is the change management that needs to happen, because you’re basically building a new habit for the entire company and that could be met with resistance.

It doesn’t mean that it’s not going to work. It means that, realistically, you need to put in the work for it to happen. This is very different from establishing a company from the ground up as a remote company, because then you get to come up with the rules of engagement from the start.

When we’re talking about change management, that can be tricky. It has to be a main point of focus. And this leads me to my second point. I think a lot of companies are not investing the resources to do it. So when you think about the resources that I’m talking about, it can’t be everyone’s job to figure out how to transition. You need one person to drive it forward.

And that’s where we’re seeing heads of remote coming in. You need to dedicate the resources to make it happen. If not, ambitious companies will focus on their business goals, and figuring out remote-first will become this hard thing that nobody wants to do.

In Singapore, a lot of companies treated remote work as a stop-gap solution until they could return to the office. Right now, in Singapore, many people are rushing back to the office because it’s been a difficult two years and they haven’t really changed the way they work. They’ve just been waiting to go back.

If your remote work strategy is an interim one, it’s not going to gain traction. You will always have one foot out of the door.

That’s the case for everything we want to invest in.

The other thing that gets really challenging is, for companies that need to work across borders and cultures, if they don’t have some element of asynchronous work, then it’s going to be very difficult because everyone is going to be in meetings all day which will sap people’s energy.

I suppose companies shifting to remote-first after adopting an interim strategy during the pandemic will need a completely different strategy…

Yes, but that’s exciting, because if they’re saying they’re moving to remote-first, then they’re actually committing to making the change versus saying ‘oh, we’ll figure it out.’ It infuses your entire employee’s lifecycle. Once companies commit to it, then great changes can be made.

What are some ways managers can adopt remote-first mindsets and unlearn biases based on proximity?

Managers who do not already micromanage will have an easier time making the change because they will be more comfortable with not needing to see people working.

In an office, we take it for granted that we can see someone working and we can just tap them on the shoulder and be like, hey what’s the status with this piece of work?

In a remote-first setting, you need to figure out a different way to check in with people and build that trust. And on the mentoring and coaching side, it’s also really important to figure out how to build psychological safety and trust your team because mental health challenges and burnout are difficult to spot in a remote-first setting.

And especially when they had to go through the pandemic and it was a stressful global experience that was a very real situation for a lot of people.

So the way to do this is by being really intentional, building that connection with the team, and making sure that in your touchpoints and your one-on-ones, you’re not just looking at the work, but looking at the person. Are you walking with them on that journey, even though you’re not in the same office?

And if you’re a hybrid manager of a hybrid team, it’s extra challenging because you have to figure out how to bridge the way you manage someone in person and the way you manage your other colleagues remotely.

And you have to be very clear that you’re not letting your biases influence the performance reviews, for example.

Do you have any tips on spotting burnout when someone’s working remotely?

At cargo.one, we definitely keep an eye on engagement.

On a one-to-one level, it’s about being sensitive to changes over time in the way someone is engaging with their work. If you’re using Slack, for example, it’s the way they’re engaging with written messages. Maybe they seem like they’re participating less? Or they’re less engaged in conversations? That’s one side.

During one-on-ones, we try to have video meetings by default. I know phone meetings are helpful when it comes to managing energy, but at least when it comes to one-on-ones, it’s great to have the video on because you can see how someone is doing or if they’re distracted and drifting off, for example.

We also need to normalize conversations around mental health. People should feel they’re able to say ‘hey, I’m struggling, can I get help with this?’ or even, ‘I need to take a personal day’.

They need to know they won’t get in trouble if they need to do that. It helps if leadership sets that tone.

There are many ways to approach this. But I think the main thing is to be more sensitive about how someone is doing. And just talking with them and being human. It’s not that difficult.

What are some ways to encourage collaboration and team culture and distributed global teams?

You need to look at both the micro moments and macro events. So you can have macro events, like a fun happy hour, for example. The idea is that you create situations where people can interact with each other as human beings.

At the macro level, this could be launching coffee chat systems where people reach out to someone they don’t typically work with for a social catch-up. So you could build relationships that way.

At cargo.one, we launched a virtual Christmas event last year with rooms everyone could pop into. We had events like ‘name the tune’ and a treasure hunt. That gave people the opportunity to talk to each other.

Of course, there is also organizing retreats and off-site meetings so people get the chance to meet in person.

And then for collaboration, it’s about finding a system that works. Make sure that the project management system you use is available to everyone. And then have clear rules of engagement, and clear guidelines around how to use the system.

I think one thing that doesn’t come through very often is that everything is in the process of refinement. You have to take a very iterative approach. It’s not one and done. You’re not going to be like, ‘we’ve nailed it, we’ve figured out how to collaborate’.

Every team is different. So it’s about working with your team to figure out what works now, what might need changing down the line, and how can you iterate together.

Where do you see remote work in five years?

I’ve always thought that remote work is the future of work. The pandemic accelerated this shift. I think in five years, we’re going to see more companies go remote-first. At this very moment, a lot of companies are experimenting with remote work because they have to, but they are not fully committed to going remote-first.

I think in five years, we’re going to see more people embrace remote-first because they’re going to hit some of the roadblocks we talked about, especially with hybrid work.

There will be a lot more startups and businesses tailored to helping remote companies thrive. If the last five years are any indication, the next five years are going to be very exciting. I’m keen to see how everything goes!

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