10 lessons over 10 years: Celebrating a decade of caa
Four times a year, I host a company wide town hall. I started doing that when we were just five employees and it continues until today. Admittedly, the meetings are equally exciting and uncomfortable for me. At each town hall, I cover similar topics: successes, challenges (I never call them failures or problems!), team accolades and celebrations, and our plans for the quarter ahead. While it’s easy to get excited to share that quarter’s successes or celebrate team members who have done amazing work, it’s also anxiety-inducing to talk about the challenges or address feedback and questions from the anonymous survey we ask all our team members to fill out prior. But, because I believe in transparency, I know this process ultimately brings the team closer together to accomplish our goals.
This month’s town hall was a particularly momentous one for me: 2025 marks 10 years of caa! Ten years of hard work, long days, expansion to new cities and of our digital platform, welcoming new people and saying goodbye to others. We survived those extremely difficult first five years of a startup, a pandemic, a transition to the virtual world, and so many other struggles and challenges in between.
But our milestone year is also an opportunity to look forward, and at this month’s town hall we did just that, officially announcing a visual rebrand across our entire platform and a name change as well. We are now officially ‘caa,’ a new, shortened company name that I believe perfectly reflects this sleek, nimble, adaptive company that we have become.
While the past 10 years have not been easy, they have been some of the best of my life. I personally have developed more than I could have ever imagined. It might sound weird, but I feel my brain is more malleable than before and it makes me so excited for the future. I am certain that whatever I am hit with, I can manage.
Reflecting on all the transformation we’ve experienced in these 10 years as well as the transformation yet to come, I would like to offer 10 lessons I have learned over this time:
- Leaders are visionaries. We must see the future before it becomes a reality. When I started the company in Miami, I knew that we would soon be in many more markets. When we started onboarding our first personnel, I knew we needed to automate the process as if we were onboarding 20 or 200 people at one time. Even when the naysayers minimalized who we were at any given moment, it was my job to ignore and see the whole picture. It was, and remains, my responsibility to continue to think big and to consider a reality that is not currently here but soon will be.
- Leaders must have a plan A, B, C, D, E, F… They say: Make a plan, and God will laugh. That is why I make a million plans – one always seems to work out. If I can predict future scenarios, I can best prepare my team for a successful outcome.
- Leaders cannot do it alone. When I really reflect on all that we have accomplished, I know it could not have been possible without my team. I take pride in surrounding myself with people who are smarter than me, who have different talents than me, who have different opinions than me. All their contributions individually have enabled us to rise together.
- Leaders must trust their gut. When I think about all the times I made the wrong decision because I did not trust my gut, my stomach literally turns over. It is very easy to let the intellect or the ego drive a particular decision, and override the deep feeling that something is just not right. I lean into that feeling so much nowadays and I find that while it’s not 100% accurate, nine times of out 10, my gut truly knows the answer.
- Leaders are adaptive. I cannot emphasize how proud I am of our adaptability over the past 10 years. Office too small? Let’s move! Someone can’t make a meeting? Someone else fill in! Pandemic? Virtual it is! Readers want more digital? You got it! I know we could not have grown as we have done if I were too married to a particular idea or way of doing things. I have always kept my ear to the ground and made necessary changes.
- Leaders are transparent. As I mentioned above, town halls can be a great source of anxiety when I am basically showing everyone how the sausage is made. But whether it is my team members, our clients, or our readers and subscribers, transparency is what builds trust, and trust is what builds long-term relationships.
- Leaders hold themselves accountable. As I always tell my team: it starts with me. I set the example. If I don’t put the work in, how can I expect my team to? If I don’t deliver what I promise, how can I ask that of others? And if I don’t address a problem, how can I ensure that others will? Hosting these town halls and sharing the good, the bad and the ugly is a way of telling my team: I am accountable. By admitting fault or apologizing when I know I have misstepped is my way of telling people that I know I am not perfect, but I am always trying.
- Leaders must continue to learn. I would never claim that I know it all. First, that is simply not true – no one can know everything. But more importantly, what use am I to my team if I have maxed out? If I do not make a conscious effort to learn and grow, I am basically telling my team: that’s it! This is all you’ll ever get. And who wants to follow that forever? When leaders continue to learn, not only do they bring new and better ideas to the table, they set the example that there is more: more possibilities, more growth in the company, better ways to accomplish tasks or projects.
- Leaders make the tough calls. In football, not everyone might agree with the referee, but they are there to make those tough calls. Leaders, too, function as judge and jury, referee and tie breaker. This is not always an easy or enjoyable place to be. But we must have the overall vision and mission and see the entirety of the situation to make the best decision for the future.
- Leaders are human, too. Listen, I certainly make mistakes. I like to keep them on the small, perhaps embarrassing side, but sometimes I do miss the mark. I am my own worst critic and will start to beat myself up before anyone has to open their mouth. But what I remind myself is that we are all humans and all humans are infallible. All I can do is try my best and do better next time.
What about you? What are your best lessons?
