5 Leadership Lessons for CEO Founders

Robert Reffkin is the founder and CEO of Compass, a real estate technology company that recently went public and is now the largest independent brokerage in America. On June 28, Cresset will welcome Robert for a virtual event to discuss Compass’ IPO and his forthcoming book, “No One Succeeds Alone: Learn Everything You Can from Everyone You Can.”

Below, Robert shares five leadership lessons for CEO founders, which he will expand upon during the webinar on June 28.

1. Love your customers. Listen to your customers.

At Compass, we have an industry-leading artificial intelligence (AI) team that’s built some amazing AI tools. But the simplest piece of technology we’ve built is actually our most powerful: the feedback button. It provides a way for the real estate agents we serve to tell us what we need to do better. So many companies think they’re going to come up with the next big thing out of thin air. That they know best. We believe that the people we’re building for already have all the answers — why wouldn’t they? It’s our job to listen and then turn their dreams into reality.

2. Dream big and dream concretely.

When I was starting high school, and again before I started college, I sketched out every single course I wanted to take on a huge piece of paper. It inspired and energized me. Of course, I didn’t end up taking half of those courses, but being able to picture every step between where I was and where I was going gave me the energy to begin.

Every time I’ve gotten knocked down in life, I’ve done the exact same thing. When I realized I wasn’t going to succeed as a management consultant at McKinsey and needed to shift careers, when I lost my entire life savings in the stock market in a matter of days, when my long-time college girlfriend broke up with me, when I almost got pushed out of my company one year in because I was leading the company through a major pivot—each time, I was able to bounce back with passion because I forced myself to start dreaming big again.

At Compass, we ask the question, “What does success look like?” before every project. Imagining the outcome of what we’re doing, what effect it’ll have on people, what it’ll actually look like if we accomplish what we’re setting out to do is amazingly clarifying and motivating.

3. Create a culture of collaboration.

One of our core principles is to “collaborate without ego.” Collaborative people give you energy. Collaborative people find solutions. Collaborative people don’t let their egos get in the way of progress.

That’s why I’ve learned at Compass that values aren’t what you say—it’s who you fire. Early on, I made the decision to fire an extremely successful agent who was being verbally abusive to his staff. It was not without risk to the company, since he was making us a lot of money, and we didn’t have that many other highly successful agents at that point. And I’ll be honest, I waited longer to make the call than I should have. But when I did, I was shocked at the response. That one act defined and strengthened our young culture more than 100 speeches about what we stand for.

4. Invest in relationships.

I’ve always invested heavily in relationships. It takes years to build trust and a good reputation and only a few seconds to ruin it. I built relationships with 100 different mentors growing up and in my early career by focusing more on what they were getting out of the relationship than what I was. I tried to put myself in their shoes. I made a point of sharing an insight from my age group that might benefit them, and also made sure they knew that I valued their time by putting their advice into action and writing handwritten letters sharing the impact their wisdom had on my life.

5. Assume anything is possible and then figure out how to get it done.

At Compass, I ask people a couple of questions: “For 10 minutes, let’s pretend you had to do it. After ten minutes, you can say, ‘It’s impossible and I can’t!’ but for these 10 minutes, tell me how you’d make it happen if you absolutely had to.” And, “If this one problem or task were your entire job, how would you approach it?”

You’d be amazed how many times those two questions are enough to unlock the answer. Forcing your brain to believe something is possible often enables you to find the path that makes it possible; seeing how something might work in a perfect world helps you figure out how to make it happen in the real world.

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About Cresset

Cresset is an independent, award-winning multi-family office and private investment firm with more than $45 billion in assets under management (as of 04/01/2024). Cresset serves the unique needs of entrepreneurs, CEO founders, wealth creators, executives, and partners, as well as high-net-worth and multi-generational families. Our goal is to deliver a new paradigm for wealth management, giving you time to pursue what matters to you most.

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