Balance: I spoke to this earlier in the article — leaders who exemplify a good work-life balance will have employees who feel valued in all areas, and ultimately show up for you when it matters.
We are living in the Renaissance of Work. Just like great artists know that an empty canvas can become anything, great leaders know that an entire organization — and the people inside it — can become anything, too. Master Artists and Mastering the Art of Leadership draw from the same source: creation. In this series, we’ll meet masters who are creating the future of work and painting a portrait of lasting leadership. As part of this series, we had the pleasure of interviewing Lindsay Gonzalez.
Lindsay is the Founder of SWIM, a fractional COO service company leading early-stage tech companies from 0–1. Lindsay has 13+ years of experience leading companies from startups through high-growth stages and beyond, taking a systems-driven and people-first approach. As a 3X founding member of successful tech companies and a 2X employee #1, Lindsay has handheld some of the most visionary leaders through countless difficult decisions. She played a key role in growing Zeta Global to over 1,000 employees by leveraging data-driven cloud technology that took them to a recent IPO at a 1.27b valuation. In 2017, after more than a year at sea working on medical aid and oceanic research projects, Lindsay helped to found and grow EarthToday, a Netherlands-based mass-scale nature protection engine. She also helped produce this Weather Channel documentary and this Discovery docuseries about the Arctic ice melt in the Northwest Passage. In 2020, Lindsay led Playground through a successful $2.3M raise, then joined the team full-time to launch a scaling web 3 social platform. She started SWIM in 2022 to help tech leaders achieve success. For Lindsay, it’s all about building technology that allows more of our differences to create more joy and less tragedy. She does that by growing for-purpose companies with impactful technology, starting with building strong teams poised to accelerate in strategic markets.
Thank you for joining us. Our readers would enjoy discovering something interesting about you. What are you in the middle of right now that you’re excited about personally or professionally?
Thanks for having me! Lately, outside of the time spent with my clients, I have been working alongside my business partner and co-founder, James Reid, to build SWIM and dream up where we want to take it in the future. After years in the weeds of building other peoples’ companies, it feels so exciting to build my own, especially in this moment when the world is truly re-thinking the role that works plays in our lives. With SWIM, we’re wanting to create a magical team of operators who care about culture, social impact, and the environment, to give the founders building meaningful technology a true leg up.
We all get by with a little help from our friends. Who is the leader that has influenced you the most, and how?
Throughout college, I worked as a TA for an artist and professor named Emil Lukas. He had a way of leading the most unsuspecting students through a creative process, and I watched so many of them transform the way they think about art and exercise their own creativity. Football jocks and bio-chem majors would step into an entry-level art class with the “I have zero artistic bones in my body” mentality and finish the course with a whole new way of seeing. It left a big impression and has taught me the value of teaching with empathy. I think it’s why I love managing people; I get to show younger employees that they can take up new skills and interests to help them grow in their roles.
Sometimes our biggest mistakes lead to our biggest discoveries. What’s the biggest mistake you’ve made as a leader, and what did you discover as a result?
Many years back, an older male leader at a company I worked for made a few harsh comments about something one of my younger female employees wore to the office. The outfit was a bit tight, but not inappropriate, and I knew his issue was more about her body type than the clothing. He asked me to speak to her about appropriate office attire, and after kindly resisting a few times, I gave in. She quit a few weeks later. I truly regret not standing up to this man sooner — we had several follow-up conversations with the larger leadership team about the matter, and it became clear to everyone involved that he should never have felt entitled to comment in the first place. Since then, I have learned to examine asks from leaders more closely and not simply do as I’m asked. It’s OK to question leadership. Sometimes, doing exactly that can help everyone learn and grow. I encourage employees who work for me to question me, as well, and some of the best learning moments have come from it.
How has your definition of leadership changed or evolved over time? What does it mean to be a leader now?
I used to conflate influence with leadership. But just because someone has the loudest voice in the room doesn’t mean their words are the worthiest of attention. Lots of people can take up space — today’s leaders, though, need to make space for others by listening and letting new voices be heard.
Success is as often as much about what we stop as what we start. What is one legacy leadership behavior you stopped because you discovered it was no longer valuable or relevant?
I absolutely love this question. Working in a fast-paced advertising environment in my 20s and then moving toward startups, I used to play into the ‘always available, always on’ mode. I thought I could impress other leaders by seeming totally dedicated to my work. What was happening, though, is that my employees felt like they had to do the same. And the results were… not great. When people feel like their time outside of work is not valued or respected, they become resentful of leadership, and eventually, they move on. When I started working smarter and truly turning off at the end of a workday, on weekends, and sometimes even for long lunch walk, I noticed a shift. Employees feel empowered to show up during the time they’re paid in full force. They’re more present, more efficient, and more joyful, because they’re shown that their time is valuable. So they treat working time as valuable, too!
What is one lasting leadership behavior you started or are cultivating because you believe it is valuable or relevant?
Setting diversity goals early, tracking to them constantly, and helping leaders adjust to meet them. It’s 2023, and we can’t ignore the importance of representation in the workplace (or the proven value it brings) like the leaders who came before us did. When leaders build their companies with intention, they don’t have to back-track and correct their cultural mistakes later, which will save heaps of time and money. They’ll also attract and retain more young talent. It’s a win-win.
What advice would you offer to other leaders who are stuck in past playbooks and patterns and may be having a hard time letting go of what made them successful in the past?
Take some time off. When I meet a leader who is stuck, I am willing to bet that they’ve never taken a true pause to reflect on what truly matters to them in life — what really makes them feel whole (or, at least, it’s been a while). I have taken extended breaks many throughout my career and will continue to do so. Those periods have been so valuable in helping me to clear my mind, get back to basics, perhaps see and experience new and foreign cultures, and let go of behaviors that no longer serve me. I always re-enter my work-life with more balance than before.
Many of our readers can relate to the challenge of leading people for the first time. What advice would you offer to new and emerging leaders?
Take the time to get to know the people you lead. Listen to them. Understand why they’re on the journey with you. Ask about their goals and take notes so that you can really help them grow. It may not be realistic to know every single person on a deep level, but at the very least, you can know the ones you manage directly and encourage them to become good listeners as well. A leader who actively listens and cares has a positive trickle-down effect that can be felt throughout an entire company.
Based on your experience or research, what are the top five traits effective leaders exemplify now? Please share a story or an example for each.
- Active listening: My last answer covered this, but here’s a bit more context: not too long ago, I briefly consulted for a leader who constantly cut people off in conversation and talked over people. I noticed how one-sided their relationships seemed and could practically feel the eyerolls of others hitting me through my screen. Nobody felt heard, and nobody felt impressed. Today’s leaders need to practice slowing down and listening if they want to motivate a team to work on their vision, even if they think they know best.
- Empathy: I’ve seen many leaders who have had great success or wealth fail to imagine the struggle of those working for them, flaunting their lavish lifestyle without thinking. Leaders need to put themselves in the shoes of the lowest-paid employee often enough to ensure fair treatment and create a growth track at all levels of a company.
- Humility: I see fewer and fewer people, especially those of younger generations, falling for the narcissistic egomaniac who leads through loud intimidation. Many effective leaders have historically had these traits, but I think that the pandemic made us really question who we want to spend our time around, and that heaps of employees in tech have chosen to level up by leaving their fearsome leaders behind.
- Balance: I spoke to this earlier in the article — leaders who exemplify a good work-life balance will have employees who feel valued in all areas, and ultimately show up for you when it matters.
- Kindness: this one is simple. No story or example needed.
American Basketball Coach John Wooden said, “Make each day your masterpiece.” How do you embody that quote? We welcome a story or example.
I’m going to go ahead and say that I don’t quite agree. Not every day can be made a masterpiece. Everyone has hard days — days they simply don’t want to get out of bed, or can’t… I think that it’s important to understand this as truth and treat ourselves and others with grace on the non-masterful days. Doing so might just allow us to show up and be truly present most days, and that should be celebrated.
What is the legacy you aspire to leave as a leader?
I hope that those who consider me a leader think about the time we spent together and smile. It’s that simple. And maybe, if they end up in leadership roles, the people they work with smile when they think of them as well.
How can our readers connect with you to continue the conversation?
Thank you for giving us the opportunity to experience a leadership master at work. We wish you continued success and good health!