Cathryn Lavery of BestSelf Co: Five Things You Need To Know To Successfully Manage a Remote Team

No water cooler moments — remote workers can’t pop into someone’s cubicle for a quick catch up and as a leader, you can’t keep pace on what’s happening in your company through office eavesdropping. Instead, it would help if you were more intentional with your communication.

As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Cathryn Lavery.

Cathryn Lavery is an entrepreneur and creator. As co-founder and CEO of BestSelf Co., Cathryn helped take the company from zero to 8-figures in less than two years. BestSelf Co. won Shopify’s Build a Business Competition in 2016 and the Build a BIGGER Business competition in 2017 — making BestSelfCo. the only company to win both awards consecutively.

Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

I grew up in Northern Ireland and went to university in England and Scotland, where I trained to become an architect. After graduating in 2011, I secured my dream job as an architect in New York City. I was super excited to emigrate to the US and start a new life. But things didn’t work out as planned!

I’d already interned for the company I was moving to New York City for. They knew my work and I’d accepted a salary of $40,000. A couple of months before moving over, I got an email to say my pay was being cut by 25% to $30,000 because there wasn’t enough work. It was a blow, but I was reassured by their promise to increase my salary once the workload increased. But that wasn’t the only goal post to move…

I arrived in the US with just a few hundred dollars to my name and two weeks to find my feet before starting my job. But one week in, my new employer rang with the news that they still didn’t have enough work for me. They were pushing my start date back a further six weeks. It was at that point I realized that I couldn’t trust a job to look out for me.

So, to help me get through those first six weeks with no income, I started to hustle and do things on the side. I launched my first Shopify store and continued working on it alongside my architecture job after I started. About two years in, I realized architecture wasn’t for me. Besides, my Shopify store was generating more income than my paid job — and I was only putting a couple of hours into it each week.

At that point, I quit my job to become a full-time entrepreneur and I’ve not looked back.

Can you share the most interesting story that happened to you since you started your career?

Winning Shopify’s Build a Business competition and then the Build a BIGGER Business competition in two consecutive years — the only company to have done so. It was an incredible experience that opened so many doors and connected me to some incredible people. In fact, the competition was one of the reasons I set up a Shopify store in the first place! I was attracted to the incredible prize, which was something money can’t buy.

I first entered in 2012 and came nowhere near to winning, but that only made me hungrier. I decided to enter again with BestSelf Co. in 2016. I set a goal, figured out what I needed to do, and got my head down. It’s all about persistence.

The win gave me some of the best experiences of my life as well as opening doors that wouldn’t have been possible otherwise. For example, I ended up playing Monopoly with Daymond John for over 6 hours. We played until 2 am while staying at the Great Gatsby mansion. I found out later that Daymond uses Monopoly as a way to test people. It turns out that Monopoly is very revealing. It shows you how people make decisions, strategize, and use money. You can also see how people play and whether they’re willing to cheat! Daymond liked the way I played, and this transformed into a deal where he endorsed the Self Journal and gave it out to everyone in his co-working space.

This story is a reminder that it’s how you cope with rejection that matters.

I didn’t win in 2012, but I didn’t give up either. I’ve learned that sometimes rejection is the best thing that can happen to you because of what it inspires you to do afterwards. I’ve learned to not believe in regrets. Regrets are all about the timeline. In the thick of it, things may feel terrible and upsetting, but as you zoom out, you often see the ‘failure’ ended up serving you in ways you couldn’t have expected.

In other words, focus on the timescale and not the problem to find the silver lining.

Not all gifts come wrapped. Some gifts are tough to swallow at the moment; it’s only later — after time has passed — that we realize how incredible they actually were.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

There was a time when I went to the wrong job interview and ended up getting the job!

As part of becoming an architect, I needed to spend a year in an office. To increase my chances, I secured six interviews with different firms on the same day. I had two in a row and the first company kept me longer; joking that they were doing it because they wanted to hire me! It meant I was in a rush to get to the next interview. And that’s when the mistake happened…

There are two firms in Belfast with very similar names. I ended up going to the wrong one.

When I walked into the office and announced that I was here for my interview, they said they had nothing scheduled. They assumed it was their fault so they looked through my portfolio and interviewed me anyway.

30 minutes later they offered me a job.

I didn’t realize my mistake until I got an email from the company I was supposed to interview with. They wanted to know where I was!

This experience taught me that if you’re confident in yourself, you can still win — even if you make a mistake.

What advice would you give to other CEOs or founders to help their employees to thrive and avoid burnout?

I was pretty close to burnout at uni.

I worked all the time and barely slept. Back then, long hours felt like a badge of honor. I thought I had to put in the hours to be successful, but it wasn’t healthy.

One of the best ways I’ve found to avoid burnout is to understand when you do your best work. It’s not about the number of hours you work, but how productive you can be in the time that you do. There’s little point sitting at a desk when you feel uninspired and exhausted. Better to take a break and come back when you’re feeling motivated.

And anyway, we vastly underestimate the value of ‘down’ time.

Taking time out gives your brain the space it needs to strategize and think about things at deeper levels. I’ve come up with some of my best product ideas when I’ve not been trying. Without space to think, we default to action, which means we’re focused on doing stuff and checking tasks off. Thinking time creates opportunities to mull over the bigger picture — which often morphs into the birthplace of brilliant ideas.

Other strategies include prioritization — following the 80/20 rule — so you can identify the levers that when pulled make the most significant impact.

Another strategy I swear by is to distil your goals into habits. Figure out what steps you need to take every day to move the needle consistently in the direction you want to go. You’ll be surprised how much you can achieve when you take baby steps consistently.

Ok, let’s jump to the core of our interview. Some companies have many years of experience with managing a remote team. Others have just started this, due to the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?

Five years — BestSelf Co. has always been an online, remote company.

Managing a team remotely can be very different than managing a team that is in front of you. Can you articulate for our readers what the five main challenges are regarding managing a remote team? Can you give a story or example for each?

1. No water cooler moments — remote workers can’t pop into someone’s cubicle for a quick catch up and as a leader, you can’t keep pace on what’s happening in your company through office eavesdropping. Instead, it would help if you were more intentional with your communication.
2. Lost in translation — when you’re not face-to-face or in-person with people, it’s harder to understand the nuance of what you’re saying or your tone. In the past, I’d invite my team to hop on for a one-to-one because I wanted a catch-up, they’d interpret the ‘let’s talk’ as an indication they’d done something wrong!
3. Not brainstorming in the same room — there’s a certain vibe you get from being in the same space as someone else who’s working on the same thing. It’s not impossible to do this remotely, but it’s harder.
4. Lack of connection between co-workers who’ve never met. It can be a challenge to create a close team community when team members haven’t met in real life.
5. Worry that your workers are doing what they should be doing? When the pandemic first hit, we ran an online summit sharing insights about effective remote working. One of the questions that kept popping up was how do you know if your team is working if they’re not in the same space as you? Here’s my answer to this… if you don’t know what your people are doing because they’re not sat in front of you, you’ve got a bigger problem! Physical presence at a desk is not an indication of output. Results are.

Based on your experience, what can one do to address or redress each of those challenges?

1. Introduce intentional communication strategies. For example:
2. Team chat channel on Slack so there’s space for your team to socialize with each other
3. Use GIFs — they’re vastly underrated as a way to communicate and connect
4. Hold in-person retreats — we do these twice a year because they help strengthen team bonds and relationships
5. You can stop things being lost in translation by getting on a Zoom call [so you can see each other’s facial expressions] or by recording audio notes [so your tone of voice is clear].
6. We have in-person team retreats twice a year where we factor in time for brainstorming and collaboration. We have regular online working sessions and if the need is sufficient, I’d arrange an in-person working session and fly in the key people involved.
7. We ensure Slack conversations and team meetings aren’t 100% work-related. Having space to socialize is critical. We do a Secret Santa each year with an online opening of gifts on Zoom. We’ve even played games on a Zoom call! There are plenty of ways to create a strong culture and feeling of connection. You just have to be creative.
8. I’m interested in the output my team creates — NOT the hours they work. I don’t need to have my team in the same room to know that they’re working, I just have to look at how the needle is moving on the business. Everyone on the team has targets connected to the bigger business goals. This is all the visibility I need to see how effective my team is. Another way to ensure your team delivers is to hire the right people. Remote workers need to be self-motivated and be able to use their initiative. I look for people who don’t need endless handholding.

In my experience, one of the trickiest parts of managing a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote employee?

As a leader, you need to master the art of giving feedback to your remote team. You can let things sit, or they fester. With a remote team, you don’t have the luxury of being able to pop into someone’s cubicle or ask them to come to the office to see you! Instead, you have to rely on the tools available.

Constructive criticism by text, Slack, or an email can come off as too harsh.

I recommend getting on a zoom call and giving feedback that way so the individual can pick up on the nuances and your tone. If it’s not possible to get on a Zoom call, I’d record a Loom video so they can see your facial expressions and hear your tone of voice on their screen.

Another alternative is the ‘record’ app in Slack, which you can use to record your voice while giving feedback.

Can you specifically address how to give constructive feedback over email? How do you prevent the email from sounding too critical or harsh?

I wouldn’t recommend giving feedback over email because it’s too hard to communicate your intended nuances and tone. Instead, I’d recommend recording a Loom video of your screen as you walk through your feedback. Not only is this option a lot quicker, but it also prevents things being lost in translation.

Can you share any suggestions for teams who are used to working together on location but are forced to work remotely due to the pandemic. Are there potential obstacles one should avoid with a team that is just getting used to working remotely?

One of the most important things is to leave time and create space for teams to keep being social with each other. If people are used to an office environment, they may find remote working more isolating. There is no physical water cooler where people can have a conversation and catch up. There are ways to create a similar experience online. For example, you can create a team chat channel on Slack for chit-chat conversations and connection. We also have weekly calls to talk about our weekend plans.

One of the biggest obstacles is adjusting to working from home. You’re going to encounter new distractions — especially if you’re homeschooling children. Expectations need to change with remote working. Your team may not work the same hours as they would in the office, but that can be a good thing. Not everyone is at their peak between 9–5. Remote working can create flexibility for people to discover when they work best.

Remember, you don’t measure productivity by hours active on Slack. You measure it by the results your team achieves and the work they get done.

What do you suggest can be done to create a healthy and empowering work culture with a team that is remote and not physically together?

Everyone on the team must be committed to the mission of the company. We’re all united around a common WHY. Everyone feels called to step up and do what’s right by the business and our customers because of a shared value we call Absolute Ownership.

It’s essential team members feel purposeful in their work too. Everyone’s work is important and necessary. No one should feel like a number because everyone is a vital cog in the BestSelf Co. machine — all pulling together to do show up in the best way we can. This desire to impact is baked into everything we do — from the way we serve our community, to how we create products based on customer needs, to our internal Slack channel where we showcase and celebrate customer success stories.

I’ve said it already, but building a connected culture is also important. BestSelf Co. feels more like a family because everyone cares for and looks out for each other. Everyone is willing to step in to help where needed because we all care about winning.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I want to inspire people to invest in personal development so they can become their best self — not just for personal gain, but because of the ripple effect it has on everyone around you.

Your best self is personal… it’s whatever it means to you.

But when you improve yourself, other people see it — and that transformation inspires others to seek out the best version of themselves too. You shouldn’t stop learning just because you left school. Learning needs to be a lifelong commitment. Self-education is that tool, which empowers you to keep growing, expand your comfort zone, and raise the standards and aspirations you have for your life.

Best of all, you never know the impact your personal ripples make as you become a better person.

Looking back, if I hadn’t committed to personal development when I did, there would be no BestSelf Co. In turn, we wouldn’t have impacted the people we have — both our customers and the team. My life would be radically different too. For example, I’d probably still be working in a job and industry that wasn’t for me.

Personal development and a desire to be your best self opens a door for a more successful and fulfilling life. It’s why I’m passionate about creating products, tools, and resources that can guide people along that path.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Not getting what you want either means you don’t want it enough, or you have been dealing too long with the price you have to pay.” — Rudyard Kipling

For me, this quote captures the idea that you can get anything you want if you’re willing to commit to it and work for it. This quote reminds me that I have control over my life and my results are down to me.

A lot of the time, people fall short of where they want to go because they stop too soon. They want something big, but don’t take the right daily actions, which means they don’t see sufficient progress so get disillusioned and disinterested.

This quote is a reminder that you have to do the boring stuff too. It’s a reminder to stick to your habits instead of constantly switching up or trying something new. Taking the right actions over a long period of time is what gets results because that’s when the compounding effect kicks in.

Thank you for these great insights!

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Cathryn Lavery of BestSelf Co: Five Things You Need To Know To Successfully Manage a Remote Team was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.