Cultivator of Talent: Having the right team in place is the best way to guarantee success and growth. Put the time in at the beginning to find the right talent, even if it feels tedious or overwhelming.
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 Aaron Cooper.
Aaron Cooper is the CEO of Oncourse Home Solutions, a company committed to helping homeowners navigate the unexpected, reduce costs and make home ownership enjoyable for all. Aaron leads a team of innovators and problem solvers, all with the goal of empowering customers to confidently manage their households. Aaron lives in Chicago with his wife and three sons.
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?
I’ve been in my current role as CEO of Oncourse Home Solutions for just over a year. I’m most energized by the responsibility I have of building out our team and increasing the momentum behind our mission, which means an absolute obsession with both the employee and customer experience. In just a short amount of time, we’ve hired the right talent and made huge investments alongside these efforts, so watching this team come together, lift one another up and focus on our company’s growth is inspiring.
From a personal standpoint, I’m really excited to be participating in the Chicago Triathlon with two of my sons, ages 12 and 16. I completed the Triathlon last year as well, and my older son totally smoked me, so the stakes are high this year to get out there and prove myself. I’ve been taking time to focus, train, and strengthen my body to prepare for this challenge.
We all get by with a little help from our friends. Who is the leader that has influenced you the most, and how?
No one leader has it all or can do it all. With that in mind, I’ve had many mentors, peers, and leaders who have shared their wisdom and knowledge, pushing me to be a better version of myself. Here’s what I’ve learned from them:
A previous boss of mine inspired me to be clear, concise and always get results. I remember coming to him with what at the time was the largest business issue I had ever faced. In no more than 20 minutes, he had added valuable perspective that allowed me to simplify the issue, giving me the confidence to fix it. He had a remarkable way of focusing on what really matters, and I did my best to adopt his ability to stay laser-focused on speed, as well as staying cool under pressure. There is no one else like him, and I channel his energy when I need to solve a complex problem.
One of my first bosses taught me an invaluable lesson about the importance of showing gratitude. This was early in my career, and I was fresh out of college with a heavy workload. Despite feeling overwhelmed at times, my motivation was kept high because my boss showed sincere gratitude. Simple gestures, like genuine praise and positive acknowledgment, helped me and the rest of the team to feel seen and truly appreciated for our efforts.
There was another boss that challenged me to think strategically and not take “no” for an answer. She’d continually send me back to the drawing board until I found a way through to ‘yes,’ and I’d channel my frustration with this grueling process into meaningful work that was always way better than where it started.
And lastly, I want to call out by name my peer and friend Phyl Terry, who is a true inspiration to me. Phyl is the founder and CEO of Collaborative Gain, a peer network of executives that is founded on the idea that asking for help is a core leadership discipline. The way that Phyl shows up, stands behind the organization’s mission and always is there to support its network is inspiring, and it encourages me to do the same.
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?
Every leader makes mistakes, and I can certainly look back and recognize the ones I made along the way. But, I think the real benefit of making mistakes is what comes from them– humility, grace, growth and an opportunity to course correct. It becomes easier to support others through mistakes once you have a lot of experience with making them yourself, plus it allows you to become more reflective and more sharp. I’ve also learned that the most important thing that leaders can do is own their mistakes, address them quickly and move on.
How has your definition of leadership changed or evolved over time? What does it mean to be a leader now?
I think being a leader is less about being “in charge” and more about hiring the right people. It’s about empowering them to bring their best to drive the work forward. As a leader, you can’t do it all — there’s too much to be done, and you need to stay focused on the bigger picture. Letting your team know you trust them not only builds confidence but encourages them to show up in new ways. I used to say that my superpower was my capacity to take on a million things at once. And while I will still say yes to new things, I’m perfectly okay now with letting go of things that I know my team can frankly do much better than me.
Being a leader also means you have to walk the walk and talk the talk. I roll up my sleeves and put in the hard work to set a positive example for my team and show them that we’re all in this together. I’m passionate about creating a purpose-based culture that provides a sense of belonging. I’ve made sure this purpose is in our DNA so our team knows how important it is to our success.
And lastly, communication as a leader is key. I was at a different organization during the pandemic, and as the CEO at the time, it was my job to be transparent with the team, no matter how hard that was. I communicated consistently and clearly, delivering the same message to everyone at the company to create consistency and instill trust.
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 have abandoned the idea of perfection. There truly is no such thing, and to expect that from yourself or your team is a futile effort. As long as the hard work and rigor is there, you learn from your mistakes, and you work hard to add value, the rest will follow.
What is one lasting leadership behavior you started or are cultivating because you believe it is valuable or relevant?
I’ve become obsessed (in the best way possible) with getting our team dynamic right. I’m fully committed to hiring the right people for the right roles across the board. We’re putting processes in place to develop our team and set them up for success. It’s critical to check in with your team to understand what’s important to them, understand where they want to grow and do whatever you can to foster that.
I also want my team to challenge me. They not only have permission to do this, but they are required to do this. It’s important to allow others to challenge you — it often times changes your perspective and the way you lead. Empowering those around you to challenge the status quo creates a culture of conversation and openness.
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?
Adapting and evolving is the best way to create a better version of yourself as a leader. I’ve always found it immensely helpful to allow my curiosity to lead the way. I read a lot and also make sure to talk to a lot of different people from a lot of different backgrounds. I ask questions. I listen. And I learn.
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?
I would let them know that their very best asset and secret weapon is their people. And that means you have to take the time to understand who they are, what their end game is, and how you can help them get there. Even more than that, being intentional with creating a diverse team will make you a better, stronger leader, equipping you with experiences and perspectives that you might not otherwise have. Fostering those relationships and having a vested interest in your people is when you will see their very best work come to life.
Based on your experience or research, what are the top five traits effective leaders exemplify now?
1. Inspiring: As a leader, you need to inspire others and lead by example. It’s an effective way to build strong rapport and get the very best out of your team.
2. Working Backwards: Too many people try to work forward — they figure things out as they go. While this isn’t always a bad thing, I prefer to identify my end goal and then work backwards to determine what next steps will get me there.
3. Reliable: If your team can’t rely on you — — the person who is running the company — then who can they count on? Reliability is key for productivity.
4. Cultivator of Talent: Having the right team in place is the best way to guarantee success and growth. Put the time in at the beginning to find the right talent, even if it feels tedious or overwhelming.
5. Directness: This might not be the most embraced quality, but being direct is critical. We don’t have time all the time, so being direct with what you need or want and when you need or want it is important. I promise people will appreciate this in the long run.
American Basketball Coach John Wooden said, “Make each day your masterpiece.” How do you embody that quote? We welcome a story or example.
I think this quote is really about making the most of each day. Over the years, and particularly as I’ve gotten older, I’ve done this by being very intentional about aligning my time and energy with the people, work and activities that matter most to me, grounded in my values.
I have a huge calendar that hangs in my home office, and I am intentional about scheduling in time for self-reflection. I journal and write about how the way I spent my time was a reflection of my values that week. Sometimes there’s clear alignment, and some weeks, less so. This practice holds me accountable and reminds me that I am most fulfilled when the choices I make reflect the values I hold.
What is the legacy you aspire to leave as a leader?
I want to be a leader that is remembered for delivering a high return on investments under my stewardship, both financial investments, as well as the sweat equity from employees and partners.
I want to leave a lasting legacy that I made things better — whether it’s a legacy of financial ROI or a legacy of improving the lives and careers of those I’ve worked with along the way. Giving back to the people who have invested in me throughout my journey means everything.
How can our readers connect with you to continue the conversation?
Please connect with me on LinkedIn here.
Thank you for giving us the opportunity to experience a leadership master at work. We wish you continued success and good health!