A Leader Willing to Fail Forward

In 1991, Ed Wehmer recognized a need for person-to-person, community-oriented service in the banking industry. With one briefcase and a phone the size of a boot, Wehmer set up a meeting over a card table and a few cold beers in Lake Forest with the goal of creating a customer-oriented bank. Over the course of the meeting, he discussed opportunities within the local banking industry with some associates. Soon, his perseverance and mantra of failing forward transformed the startup finance firm into Chicago’s second largest banking company.

Fast forward from this 1991 meeting to today and Wehmer is in charge of more than 160 banking locations and 4,800 employees. A key to Wehmer’s success is his ability to embrace challenges—no matter how insurmountable they might seem. During Wintrust’s formative years, as the company began to take shape, the idea of taking on big banks seemed impossible. But as Wehmer realized, the task wasn’t as ridiculous as it seemed at first glance.

“People were used to going into banks and getting a handshake from somebody they knew. They didn’t like the commoditized approach the big banks were starting to take, so that’s the hole we decided to fill.” While the task seemed impossible, Wehmer knew that there was a demand for neighborhood banks, and he could provide the supply.

While others may have felt anxious taking on the big banks, Wehmer embraced the challenge because he believed in the mission of bringing banks to the people. This mission-focused perspective is a key component of leadership that Wehmer stresses. “If you don’t care about what you do, you won’t be successful as a leader,” said Wehmer. He continually asserts that he believes in the mission of Wintrust, which has largely led to the company’s success. “If Wintrust lost sight of its mission, consumers would catch on immediately.”

“Our mission is not to line our pockets. Our mission is to provide balanced returns to our four major constituencies—shareholders, customers, employees and the communities we serve,” said Wehmer. “It’s not fair to the people who work here if we do not provide them with something bigger to work for.” Wehmer has a strong point. Leadership is largely about bringing out the best in people. When individuals believe in something, they are more likely to commit to it. It is this very phenomenon that has brought Wintrust to where it stands today. That, and—surprisingly—a little bit of failure, too.

When looking back at his journey, Wehmer mentioned that he knew from the get-go that he would fail at some point. He did not, however, look at failure in the traditional sense of the word. Rather, he looked at it as an opportunity. Simply put, Wehmer believes that taking a risk and never giving up results in a better outcome than never trying at all. His mantra is simple: if one must fail, fail forward. With this belief of failing forward, Wehmer has not only expanded his community bank to 160+ locations, but he has kept Wintrust tied to its community roots.

This concept of failure stems back to Wehmer’s belief that one must always be willing to take risks when leading. In particular, he cites the Great Recession of 2008. “Banking has ebbs and flows. It’s not difficult to see what the market will do in a few years if you look at history,” said Wehmer. “In 2006, when the market was booming, I made a decision that could have been fatal: I decided to stop expanding and instead play defense.” In short, he looked at patterns and went against the flow of other banks that were growing in the strong economy. Instead, he took a risk and halted growth in preparation for a recession. In this moment, Wehmer asserts that he fully embraced his perspective that failure is part of life, but if people and leaders are willing to fail forward and learn from prior mistakes, the possibility for growth is exponential.

He has used this lesson throughout the growth of Wintrust as he has allowed himself to delegate more tasks to his employees. Wehmer’s role is not nearly as hands-on as it was when he started the company, but he has worked with his employees to ensure that they feel confident in their roles. “As a leader, delegation is of utmost importance,” said Wehmer. “While delegating is not always easy, I have worked to help Wintrust employees grow in their roles. I make sure they know that it is okay to make mistakes as long as they learn from them and fail forward.” It is this persistence to fail forward that has kept Wintrust true to its mission.

Even as Wintrust grew into a large banking operation, Wehmer ensured that it maintained its focus on the local community. At the heart of his daily decisions, Wehmer looks at Wintrust’s roots and considers the community in every decision he makes. To this day, he holds firm in his belief that “if it is good for the town, it is good for our organization.” He proves this belief through the efforts of Wintrust. Recently, the company invested in Wintrust Arena to hold sporting events and concerts for the city of Chicago. Additionally, his passion for the community is exemplified by his personal commitment as a trustee for the Ann & Robert H. Lurie Children’s Hospital and Foundation and a participating finance board member of the Archdiocese of Chicago. Through this work, Wehmer continually gives back to the community, allowing him to lead in a manner that engages those around him and makes the world a better place.