Thriving in an Uncertain World

Chris Taylor
The Culture People
Published in
8 min readApr 22, 2020

Leading through the pandemic to help our communities emerge stronger

It’s the energy in Square Root’s campus of craftsman houses that I miss most: the close-knit familial vibe, the front porch meetings, and the casual connections.

Fourteen years ago, I started Square Root to help automotive and retail companies act on their data to solve their toughest challenges. Today, the Square Root culture and the team it attracted are my greatest professional accomplishments. As the pandemic disrupts every aspect of our lives, I have been especially introspective on how to lead our team through this uncertainty with conviction, transparency, and empathy. Whenever I am faced with a leadership challenge at Square Root, I contemplate our Thrive value. In normal times, we define thriving as revering individuality, authenticity, and both personal and professional growth. But what does thriving mean during the pandemic? I was struggling with this question as I prepared for our first virtual all-hands quarterly meeting.

First of all, it seemed strange to be talking about “normal” company topics like goals and finances as the world fell apart around us. We don’t manufacture face masks. We don’t support hospitals. Does enterprise software even matter right now? Does anyone really care? How do you lead a team when there are dramatically more important things going on in the world than the Square Root quarterly goals?

A conversation with one of my friends and advisers, Bill Kennedy, put it in perspective for me. There are always more important things going on in the world than whatever is happening in our sphere of influence. Always. Bill reminded me that there are three types of things — things out of our control; things we can influence; and things we can control. For me, it was a useful framework to get out of my own head and focus on what I could do — right now — to help the communities that I can influence, and not to focus on those I can’t.

How can I help the Square Root team, our customers, other entrepreneurs, the Austin community, and my own family become stronger despite all this adversity?

Here’s how I am personally taking action on those things I can influence or control.

To the Square Root Radicals:

We can’t control the macroeconomic impacts of the Coronavirus or when we can work together in the office again, but we can control how we rise to the occasion for our customers and each other.

I realized that one of the biggest impacts I could have would be to help our 45 Radicals have some consistency and stability in these crazy times. My first Square Root priority was to ensure job stability for our team, and therefore the financial stability of Square Root. It’s a good time to be bootstrapped and cash flow conservative with a long history and stable customers. Even though we are projecting revenue slowdowns, we can ride those out by cutting non-headcount expenses and being smart with loans and receivables. I know job security is especially stressful right now. I promise that I’ll continue to be honest and transparent and do everything I can to help us all emerge from this stronger.

Ode to the in-person one-on-ones

My second Square Root priority is fostering a supportive environment where everyone can find their own balance during this upheaval. Despite flipping to a remote workplace in a matter of days, we’re preserving our culture of authenticity, inclusion, and camaraderie from home. Caring about the health, safety, and growth of each other has always been a strength, but now it’s an imperative. It’s why we stopped all business travel and moved to work from home well before it was mandatory. It’s why we’re building new channels for connection. And it’s why we’re encouraging time for mental-health breaks and family time during the workday.

We always valued and nurtured flexibility, adaptability, and empathy, but now I want everyone to think about how we can extend grace to each other. We don’t know when a coworker’s toddler needs their attention, or a friend needs to talk, or when someone just needs a moment. Just as important, take a little grace for yourself. It’s okay to have a bad day, to take a nap or a day off, or to ask for help.

Through this adversity, let’s build new traditions, new ways to connect and communicate, and new strengths that will make our team and our culture permanently stronger.

To our customers & partners:

We can’t control the timing and speed of the recovery, but we can control how prepared we are to move quickly and thoughtfully, and to adapt to rapidly changing conditions together.

Part of our Be Customer Inspired value is that we consider ourselves to be an extension of your team and your partner for innovation. It is core to our culture and meaningful for us personally to do everything we can to help you plan and execute your response to the pandemic. We’re talking every day at Square Root about how we can help you in the coming week, quarter, and year.

There are a few things that we have done over the last few weeks to help immediately. To help corporate and field communication, we’ve turned on or reconfigured our collaboration modules at no charge. We’re also hosting a set of industry-specific peer-to-peer virtual meetings to connect operations leaders in automotive and retail. These informal discussions are about coming together, learning from each other, and making new connections. We’re holding them weekly — let me know if you would like to join.

To help you over the next few months, we have tasked our data science and engineering teams to proactively integrate relevant COVID-19 and economic data sets into our industry models. We’re making these new models available to help you plan for recovery differences in each city, and build individual plans that factor in the unique circumstances for each retailer. Our data science team and industry experts are also at your disposal to model the unprecedented future we all face.

And as we think forward to later this year, we are reworking our product roadmap to prioritize products and features that we feel will most help the unique set of challenges in executing a recovery strategy. For instance, we’re reworking the feature set and bumping up the public release of our field and retailer collaboration tool, Visits, so that it is available when we shift into recovery mode. It is part of our innovation philosophy to iterate with our customers, so please let us know your ideas.

Lastly, we miss you! A big part of the Square Root culture is living our Be Customer Inspired value and having that time to personally connect. We’ve started hosting virtual happy hours with our friends and clients, and I hope we’ll all have a chance to put out our “hair on fire” for a few moments and just be able to chat about how we’re all doing personally.

To fellow entrepreneurs:

We can’t control how the pandemic affects our industries, but we can control how we help each other navigate the change.

If you’re anything like Square Root, you started the year with high energy and an ambitious plan, and now that plan is in the trash (and on fire). We kicked off our year with a Star Wars-themed Q1 meeting entitled The Rise of Square Root, and we just wrapped our virtual Q2 meeting themed Home Alone. How quickly the world has changed.

Running an organization is lonely in the best of times. In these times, the stress, isolation, and self-doubt can be crushing. I’m a huge proponent of entrepreneurs helping entrepreneurs. I have been leaning on my fellow entrepreneurs heavily in the last few months, while also trying to be a resource for others wherever I can. I’ve been at this entrepreneurial thing for a long time; let me know if and how I can help — even if it’s just an empathetic ear.

To Austin:

We can’t control the Federal and State responses, but we can influence how we come together as a city.

Square Root’s entire DNA is based on the unique culture of Austin, and we give back where we can. As a science-loving dad of two daughters, one of the causes I am most supportive of is STEM education for girls. I’m still trying to fathom the long-term effects school closures will have on students, especially disadvantaged ones. Square Root increased our charitable giving budget by 50% and launched a matching donations program. We donated the additional funds to my favorite STEM program, Girlstart. Our women’s resource group, the Radical Girl Crew, is also compiling blogs and live Q&As for Girlstart to promote careers and female role models in technology. We’ve also taken some of the funds we would normally spend on team lunches and donated them to the Austin Food Bank to help feed the increasing number of families that need help.

Then there are the small things we can all do in our neighborhoods. I’m working between calls from my front porch so I can say hello to the neighbors, make a connection, and see if they need anything. I believe one of the lasting positive outcomes of all of us sheltering at home will be shifting to a front-porch openness versus the usual back-porch isolationism.

To my family:

We can’t control that schools are closed and we’re stuck in the house, but we can control what memories and traditions we’re creating.

I’m grateful for this time together. I recognize I have it easier than most with older daughters, Shelby (9) and Zoe (10), and the support of my wife, Teri, to manage the now 24/7 house-and-school. These next few months will become a defining moment in my daughters’ childhoods. I want to make sure we use the time to become closer as a family and build new traditions like our front yard badminton tournaments. This last month on top of each other has had its stressful moments, but I love being able to step away from work for impromptu Science with Dad or even a hug.

And lastly, to myself,

You can’t control the news, but you can control whether you obsess over it.

We have invested a lot of time at Square Root talking about mental health and connection while we work from home. After over a month, it has become clear that I’ve been running so fast to keep up with everyone else’s needs, I am not taking care of my own — and then even feeling guilty about that! I’ve read a lot about using this time for personal transformation, and I find it inspirational, but also exhausting. We certainly should use this time for personal growth, but our expectations for ourselves need to be realistic and balanced as we navigate these next few months.

If we focus on what we can influence, and help where we can, we can thrive through this uncertainty and emerge stronger together. But it is going to be hard. We are not going to be perfect.

We don’t have to be stronger every day to be stronger overall.

Chris Taylor

Square Root is a diverse team in Austin, Texas building data-curation software for the automotive + retail field. Learn more about our platform + see how CoEFFICIENT can help make your field more.

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Chris Taylor
The Culture People

Chris is the Founder and CEO of Square Root, a serial tech entrepreneur, bootstrap enthusiast, start-up mentor, father to Zoe and Shelby, and husband to Teri.