Leading a remote team and being a digital nomad — cautionary
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Leading a remote team and being a digital nomad — cautionary tale.

by Claudio CossioMay 22nd, 2019
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A few days ago the team from <a href="">Remoters</a> published an essay I wrote regarding remote work and how it can be a viable way to set up a team — <a href="">Remote work in the spotlight, how to make it work and not die trying</a> — I am a firm believer in remote work and that it is a way to give organizations or teams the freedom they need to have a better work/life balance.

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Leading a remote team and being a digital nomad — cautionary tale.

A few days ago the team from Remoters published an essay I wrote regarding remote work and how it can be a viable way to set up a team — Remote work in the spotlight, how to make it work and not die trying — I am a firm believer in remote work and that it is a way to give organizations or teams the freedom they need to have a better work/life balance.

I got some great feedback on the essay and wanted to follow up with another post, this time it is on a more personal note. There is always another side of the coin to every story and wanted to share with the HackerNoon community some of the lessons I learned in the process of leading a remote team and being a digital nomad (not by choice, but for family reasons).

It has been great leading a remote and distributed team at SoftwareDevTools (Nearsoft is our parent company) since 2015, earlier that year I had to relocate to Nearsoft’s HQ in Sonora (Northern Mexico) from Mexico City.

One of the reasons I joined the organization was for their freedom culture, you see I have family in Barcelona and this required me to travel 2–3 times a year to Spain and for Nearsoft it was not a deal breaker that I worked on a 9 hour difference time zone. I am happy to be part of such an amazing organization and culture, had some time to adapt to a flat organization but once the Nearsoft way set in the benefits of self-managing the way you work are phenomenal.

Since 2012 I have been going back and forth from USA/Mexico to Europe since my base was Barcelona at the time, it was not fashionable and there was no term for doing that….until the term Digital Nomad grabbed media attention, for me it was always “road warrior“ just being constantly on the move for business reasons not so much a lifestyle choice. But for the last 4 years, I spent 3–6 months of the year in Europe, the rest of the year was spent traveling all over North and South America.

But some major changes have happened over the course of last year, I got married (2nd time’s the charm) and have my second child as well. So I made an effort to stay on land more often, even though this year I have not done a very good job at that, for now, I have done one trip to Asia and two trips to Europe (65,000+ miles) which is definitely taken its toll on the mind and body.

In addition to a growing team, which started as just two persons inside a 100+ company and we now are 14 people and 300+ Nearsoftians. We managed to launch the product brand which is SoftwareDevTools to sell apps in the marketplaces like Atlassian and Freshworks to provide solutions for Agile Retrospectives, a Slack chatbot for daily standups, integrate Trello with Freshdesk / Freshservice and a Scrum Poker app for estimates. Now we have 400 clients all over the globe and pretty much work around the clock to serve our customers and partners.

With this context in place, I would like to share with you the lesson I have learned so far this year and the 7 years of being constantly on the road to launch Startups, mentor founders and build digital products.

Being part of a team and constantly homeward bound.

I love creating products and this cannot be done by yourself, you have to work with other people and build a relationship that will inspire one another to deliver outstanding results, this has shown throughout these couple of years building SoftwareDevTools and collaborating with my fellow peers at Nearsoft. But having the perks of working remotely is not all rosy.

SoftwareDevTools team in Hermosillo — Nearsoft HQ.

Until a few weeks ago I started to notice some behavior changes, to be honest, it was my spouse and colleagues that pointed out that I was being more aggressive and short tempered. This got me thinking and I have to thank them for taking the time to care for me and letting me know that I was not being the best of myself; many digital nomads who are constantly on the move are always on the newest trend and “hunting” for opportunities. It is a necessity since you are either freelancing or have the luxury of being part of a company that works remotely — but the feeling of always on the lookout — hustling.

One thing in common with digital nomads that are on the road, is that we feel like being “on tour”. For some of you this will resemble the “rockstar” mentality and for those that have put on their reality distortion field glasses it will be true for some years, until you feel the pain of what soldiers experience when they are “on tour of duty” and have to deal with feelings of abandonment, regret, loneliness, remorse, etc. If you do not find a way to deal with them, they will accumulate over time and you will start changing, subtle changes will happen but you will start losing touch with the ground. Your team needs a leader to be mindful and aware of how he/she reacts and avoid unnecessary frictions.

Why? Because in order to continue being a digital nomad, live the lifestyle desired (you want that photo in the infinity pool right?), you have to be good at your job and delivering results. No one will work with someone remote if they do not excel at their tasks, so teammates or employers will be happy “dealing” with you; because he/she can deliver. They will cope with your behaviors for the sake of growth and revenue. You will start to go down a path of losing touch with reality.

Also, the sensation of heading home in the distant future starts to become a weight on you. You can ignore it as much as you want, but everybody needs a family and those peers/nomads on the hostel/Airbnb/co-work will never be your loved ones, do not mistake empathy for true feelings of appreciation and care; those are reserved to just a handful of people. For those that have found them in strangers, I salute you but hope reality does not come back to tell you how it is. No one will care more for you than your family.

So find your family, go home and build something that creates roots. You will not regret it, if you are lucky enough that you can travel with your loved ones from place to place, then you have done what my mentor Evan Nisselson from LDV Capital once said: “Home is where I lay my hat down”. But for those of us that desire to stay in one place or have made commitments to be part of something that lays roots, find your home.

Your team needs for you to be in the right mindset and you need to take care of yourself. We know that exercise and meditation will be a key component in your self-care. Find the time to be the best teammate you can be.

Here is a list of great articles and essays from the community:

Anti-hustle and being sustainable.

Started exploring the reasons I was having these mood changes “all of a sudden”, it was just the realization that I could never be constantly “on tour” and that I had just overdone it. I was burned out at the expense of “delivering results” and now that I have a family that needs me home, the remorse and the guilt started to sink in. I had to face myself and start understanding that I could not make them all count, you have to let go of the opportunities and the constant hustle to be productive. Focusing on what matters is the path to sustainability.

I loved this piece from the Basecamp founders latest book — It does not have to be crazy at work:

Rather than demand whatever it takes, we ask, What will it take? An invitation to a conversation.

But this conversation is not only with your team, it is with yourself. Give yourself time to be mindful of your decisions, of your behavior, be willing to make trade-offs, cut things short and most of all find a simpler approach to the tasks at hand, to the opportunities and give yourself room to breathe.

Questions bring options, decrees burn them — Jason Fried & David Heinemeier Hansson — Basecamp founders.

So do not feel obliged to be all in at every opportunity that comes in your way, sit on it and think it over; will this bring me close to our team’s goals and can this be sustainable on a personal or professional level. Am I doing this for my own gain or is this something that will benefit my teammates. You will know when that you have started to change when you start leaning toward the I and not we; because the role of the leader is to be a steward.

I really recommend you take a look at Scott Belsky book — The Messy Middle — where it makes a great point:

A strategy is less about accomplishing your team’s objectives and more about better serving the needs of your network participants.

The role of the leader is to serve your team and your customer’s needs, you need to be aware of the frictions you are generating and discomforts you are provoking. When you lead you to need to respect and tend to the needs of others, when you start making decisions that are unsustainable you are not taking care of your team; you are serving yourself for the short term gain and this is a slippery slope downwards.

Finding the right balance is important, but when you are constantly on the move and not staying put in one place for long periods of time, this will take its toll on you and your team. Be mindful of the decisions you are taking while on the road, take into account your health and most importantly being happy about the direction you are leading your team.

Sustainable growth can only be accomplished when you are serving others and avoid short term goals. Long term outcomes require that you build a healthy team and this includes you. Be vulnerable and reach out for help whenever you feel overwhelmed, don’t be afraid to say “no” to every “good” opportunity that comes your way or discuss it some more with your team.

I will close this essay with a great quote from Scott Belsky:

Success fails to scale when we fail to focus.

Focus on the important things in life, your loved ones and who you serve.

Header Photo by Victor Bayon.