Leading From The C-Suite: Craig Gass of Qualpay On Five Things You Need To Be A Highly Effective C-Suite Executive
An Interview With Doug Noll
Be a thoughtful leader. Taking a thoughtful approach to my leadership style was imperative for me when I became CEO because I understood that I was leading a team of my fellow co-founders. I recognize the strength of everybody around me, but need to ensure we work together as a team. It’s important to consider the collective versus the individual.
As part of our series called “Five Things You Need To Be A Highly Effective C-Suite Executive” we had the pleasure of interviewing Craig Gass.
Craig Gass is CEO and co-founder at Qualpay and zealous about modernizing the payments industry to solve the problem that all businesses have to answer the same question: “where is my money?” Craig has over thirty years of both business and legal experience principally with Financial Institutions and payments companies, including BA Merchant Services and Merchant e-Solutions.
Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
I have over thirty years of both business and legal experience principally with Financial Institutions and payments companies including BA Merchant Services and Merchant e-Solutions. I started my career as in-house legal counsel. But as I continued my career, I wanted to transition to a role within the management team, which ultimately led me to pursue an MBA at the University of Oregon. In 2014, I co-founded Qualpay with a team of industry experts. Together, we’ve built this organization to what it is today, and I’m proud to serve as the CEO of this next-generation payments platform.
Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?
I have a lot of life lesson quotes that I’ve picked up over the years as I’m sure is true of all of us.But one “life lesson quote” that has stayed with me is from Francis of Assisi — “Start by doing what’s necessary; then do what’s possible; and suddenly you are doing the impossible.”
This was a quote my wife had shared with me, and it brought me back to my roots as a lawyer and reminded me to separate a problem into its various parts or issues and solve for each as you can. Sometimes the solution is a process not a single answer.
Is there a particular book that made a significant impact on your leadership style? Can you share a story or an example of that?
I don’t read many business or management books. Often, I read action or adventure books simply to relax. I also enjoy reading books on politics. I was a political science major in college during the Nixon Presidency and the Watergate scandal, so reading about politics has always been an interest of mine. David Gergen’s “Eyewitness to Power,” Tom Brokaw’s “The Greatest Generation” and Al Gore’s “The Assault on Reason” all discuss leadership, use of authority and culture in a political context, but also provides insights that are useful in other contexts as well, like business .
Another book that I found interesting is “Bourbon: The Rise, Fall, and Rebirth of American Whiskey.” Although the book is about Bourbon, it discusses the business of Bourbon as a uniquely American product and how it was built. The books I read are typically written by people who are subject matter experts in their own fields and who are also in positions of leadership. Ultimately, these books provide varying perspectives, which inform my own leadership style and allow me to be a more well-rounded CEO.
What do you think makes your company stand out? Can you share a story?
Qualpay is a small company in a very crowded and large space. To break through the crowd, we have a team of experienced payment professionals using today’s tools to build the next generation in payment technology.
Instead of focusing on how things are always done, the trick for us has been to think outside the paradigm and find ways to integrate payments into broader business solutions.
Through this lens,we’ve found that by eliminating multiple payment vendors, Qualpay is able to provide a customizable solution for our customers. As a small company in a scale industry, Qualpay stands out because we offer innovative solutions to complex problems with an efficient business model.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Recognize the power of team. As I made the transition from my role as General Counsel (a subject matter expert) to my position as CEO at Qualpay, I knew there was tremendous talent among our group of co-founders that I needed to leverage to lead the company to success. I understood that the team, collectively, was far more powerful than the sum of the individuals, and recognizing that helped me to build Qualpay on their shoulders.
Ask difficult questions without clear answers. Understanding the purpose of a question is vital as a business leader. Leaders shouldn’t ask questions necessarily to get the answer or solve a problem, but rather to start the analysis. The answer to a lot of legal questions is more about the analysis and understanding what needs to be solved first and what options are available. Sometimes there is no clear answer and that’s okay.
Bring empathy as a leader. To be a thoughtful leader, you need to understand your team as a whole and recognize each person’s strengths and challenges. That is very hard to do and made more difficult in a remote work environment. Leading from a place of empathy, understanding and thoughtfulness will always be more effective than leading from a place of control.
Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?
Our team was faced with an organization-wide challenge a few years ago, and I could see no clear way to get through it. The obvious answer at the time may have been to dissolve the company — but that was not an acceptable answer. And so to find the way, instead of asking, “What’s the answer?” I made the decision to dig through the analysis and begin disaggregating the things that were causing us to fail. Step by step, we addressed each obstacle and eventually overcame the impossible. This goes back to the quote from Francis of Assisi.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a C-Suite executive does. But in just a few words can you explain what a C-Level executive does that is different from the responsibilities of other leaders?
C-Suite executives cannot be experts in everything but are generally responsible for overseeing functions across all or a large portion of the company, including areas where they have little or no expertise.
As I mentioned earlier, ultimately, as a C-level executive, you look to the team around you — led by subject matter experts and specialists — to inform and empower your role as a decision maker. I think people over estimate the power of a CEO in particular. The real success for most CEO’s lies in the people they around them and the CEO’s ability to listen and learn. At the same time you have to have the confidence to lead. I have worked for a number of CEO’s. None were perfect.
What are the “myths” that you would like to dispel about being a C-Suite executive? Can you explain what you mean?
I’m not sure there are any myths around being a C-Suite executive, but what I’ve learned as CEO is that the work you are responsible for managing is largely work you cannot personally do. As a leader, you must rely on the team you surround yourself with, and you have to trust their ability to share the responsibility.
What are the most common leadership mistakes you have seen C-Suite leaders make when they start leading a new team? What can be done to avoid those errors?
Throughout my career, I have had the opportunity to work directly for a number of CEOs and have come across various management styles that I’ve learned from. When I made the transition to Qualpay CEO, I considered the many strengths and weaknesses of the leaders I’ve worked with throughout my career and reflected on those that stood out.
Being a thoughtful leader is one of the most important attributes. To do so, I considered what I had learned from my former bosses and identified my own personality traits that translate to strengths (and weaknesses) as a thoughtful leader. This thinking shaped my management style, which focuses on recognizing the strengths of the people around me and taking the time to understand the team. Ultimately, this has allowed me to effectively lead and truly bring the company together.
In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?
Taking the time to understand not only the individuals in the organization, but collectively, how the team operates is often greatly underestimated. C-Suite executives tend to focus on the hierarchy over understanding the team dynamics, which is a mistake.
The greatest task for me was understanding that leveraging the power of my team as a group, vastly exceeded that of each individual because they brought their expertise to the table in their own way. As CEO, the trick is to figure out how to take the different parts of the company and make the whole greater than the sum of its parts. That was the genesis of Qualpay.
Ok super. Here is the main question of our interview. What are your “Five Things You Need To Be A Highly Effective C-Suite Executive”? If you can, please share a story or an example for each.
Recognize the power of your team.
When I became CEO at Qualpay, I understood that my role would change as I made the shift from being a subject matter expert as General Counsel to working with others who were experts in areas I was not.
Ask the difficult questions with no apparent answers.
When there is a problem or an existential threat to your company, there is no clear answer. You can learn from diverse ideas and approaches, and ultimately, find the solution to seemingly impossible challenges.
Think outside the paradigm.
As a small company in a very crowded space, we are constantly having to differentiate ourselves from our competitors by thinking outside the paradigm. By looking at the industry in different ways, we find unique and innovative solutions to complex problems.
Be a thoughtful leader.
Taking a thoughtful approach to my leadership style was imperative for me when I became CEO because I understood that I was leading a team of my fellow co-founders. I recognize the strength of everybody around me, but need to ensure we work together as a team. It’s important to consider the collective versus the individual.
Analyze, analyze, analyze.
This goes back to my earlier rule of not asking a question to find the answer but rather the analysis of the question. Understanding the problem and its various components will allow you to better understand and solve the problem.
In your opinion, what are a few ways that executives can help to create a fantastic work culture? Can you share a story or an example?
Executives need to listen to their team. What is your team looking for? What does your team need? In these discussions, you need to listen to your employees to consider what can be changed or evolved, and how the organization can adapt to empower a better work culture and environment.
For example, at the start of the COVID-19 pandemic, like most workforces, our team pivoted to work from home. In a matter of weeks, I had to learn how to manage our company remotely. We overcame the challenge as a team, and we came out as a stronger culture because of it.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)
If I could start a movement to do anything, it would be to focus on the analysis and reasoning in a discussion or debate, instead of narrowly focusing on finding a single right answer.
This goes back to my time in law school and my background as a lawyer, which informed my belief that it’s important to have meaningful discussions with people without jumping to conclusions. Al Gore’s The Assault on Reason shares this idea that everything today is based on belief, leaving little room for analysis. We shouldn’t ask questions simply to find an easy answer, but rather to seek meaningful analysis.
Today, there are fewer and fewer opportunities where people are looking to debate or discuss without being locked into a predetermined answer, and I would want to change that mindset.
How can our readers further follow you online?
Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!
About the Interviewer: Douglas E. Noll, JD, MA was born nearly blind, crippled with club feet, partially deaf, and left-handed. He overcame all of these obstacles to become a successful civil trial lawyer. In 2000, he abandoned his law practice to become a peacemaker. His calling is to serve humanity, and he executes his calling at many levels. He is an award-winning author, teacher, and trainer. He is a highly experienced mediator. Doug’s work carries him from international work to helping people resolve deep interpersonal and ideological conflicts. Doug teaches his innovative de-escalation skill that calms any angry person in 90 seconds or less. With Laurel Kaufer, Doug founded Prison of Peace in 2009. The Prison of Peace project trains life and long terms incarcerated people to be powerful peacemakers and mediators. He has been deeply moved by inmates who have learned and applied deep, empathic listening skills, leadership skills, and problem-solving skills to reduce violence in their prison communities. Their dedication to learning, improving, and serving their communities motivates him to expand the principles of Prison of Peace so that every human wanting to learn the skills of peace may do so. Doug’s awards include California Lawyer Magazine Lawyer of the Year, Best Lawyers in America Lawyer of the Year, Purpose Prize Fellow, International Academy of Mediators Syd Leezak Award of Excellence, National Academy of Distinguished Neutrals Neutral of the Year. His four books have won a number of awards and commendations. Doug’s podcast, Listen With Leaders, is now accepting guests. Click on this link to learn more and apply.
