“To create a fantastic work culture, a management team should have mentors and coaches to help guide them in their leadership challenges” with Anthony Tassone, CEO of GreenKey Technologies

…The management team should have mentors and coaches to help guide them in their leadership challenges. We should be open to self-reflection and criticism, as well as confident enough to seek guidance and support when it’s needed. I have both a mentor and a coach and value their feedback enormously. For employees, knowing that their manager seeks outside advice and values personal growth also closes the gap of vulnerability within a team.

As a part of my series about about how leaders can create a “fantastic work culture”, I had the pleasure of interviewing Anthony Tassone. Anthony is the founder and CEO of GreenKey Technologies, a Chicago-based financial technology firm that provides artificial intelligence and natural language processing solutions for trading desks at top tier banks and other global finance firms. Prior to starting GK, Anthony spent 15 years in systematic global trading and product development roles across derivatives markets.

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

Growing up on the south side of Chicago I caddied at a golf course until age 15, when I caught a lucky break by getting a job working as a runner at the Chicago Board of Trade. That opportunity eventually led to clerking for several larger-than-life Chicago traders who inspired me to learn anything and everything about financial markets. The early exposure to the personalities in the business, along with my interests in science and quantitative finance, enabled me to start trading at 21. I’ve always enjoyed the challenges of building models, analyzing data and finding patterns in the markets, and those skills have benefited me as markets have evolved over the last 20 years. I took the plunge into entrepreneurship after realizing the enterprise multiple assigned to trading revenues is approximately 1x. I decided I’d rather build my own company with recurring revenue streams and IP and use what I’d learned in the industry to create long-term defensible value for others and myself.

Can you share the most interesting story that happened to you since you began leading your company?

The most important thing I’ve learned, through trial and error, is to value and appreciate character over skill set when hiring. As a trader you work in an exacting environment with very smart and educated people. Production ability is valued above all else, including character, and I approached my initial hiring with that mindset. I came to understand that particular hiring truism is actually one of the many elements of irrational behavior found in finance. Now I prioritize hiring nice people with ability, and the result is a great team of people working together toward one goal, irrespective of ego.

Are you working on any exciting projects now? How do you think that will help people?

Our mission at GK is to help financial institutions use AI and natural language processing to automate boring human tasks, which makes their businesses more efficient. The resulting cost benefits and improved workflows also increase transparency into their transactions and provide accountability to regulators and customers. Our technology is a win-win for everyone.

Ok, let’s jump to the main part of our interview. According to this study cited in Forbes, more than half of the US workforce is unhappy. Why do you think that number is so high?

In general, a lot of people don’t feel they have a purpose at work. They aren’t connected to a business mission and don’t trust management to look out for their best interests. That feeling of vulnerability results in a paralyzing work culture, and as a business gets bigger the disconnectedness only increases.

Based on your experience or research, how do you think an unhappy workforce will impact a) company productivity b) company profitability c) and employee health and wellbeing?

An unhappy workforce negatively impacts all of those things. Culture is like the operating system of a company, and if the culture is terrible then the system is prone to outages and inefficiencies. If the culture is well-planned and developed, great things get done quicker.

Can you share 5 things that managers and executives should be doing to improve their company work culture? Can you give a personal story or example for each?

1. Teams should be small. Fewer than 12 people on any given working team creates a foxhole environment where each member can be valued and productive. That keeps employees better connected to the company’s mission and the tasks at hand.
2. Recognize that after a certain point, money doesn’t motivate people or create loyalty. I overpay my employees to take salary out of the equation as far as their happiness at GK is concerned. Each employee will have different motivations to succeed at his or her job, and those incentives should be tailored as much as possible to each individual.
3. Develop cultural traits and codify them for all employees to live by. At GK we conduct personal evaluations during the hiring process and pay special attention to how candidates exhibit our company values. Management also uses our cultural principles to guide company decisions and disarm debates about decisions big and small.
4. Implement a “small things” framework, which is a real-time feedback mechanism for employee reviews. Our work culture allows for colleagues to comment on problems immediately with no negative personal consequences, leading to fewer communications-related mishaps. At GK we’ve codified the values of teamwork and solving problems, and knowing everyone is aligned in those priorities removes ego from any debates.
5. The management team should have mentors and coaches to help guide them in their leadership challenges. We should be open to self-reflection and criticism, as well as confident enough to seek guidance and support when it’s needed. I have both a mentor and a coach and value their feedback enormously. For employees, knowing that their manager seeks outside advice and values personal growth also closes the gap of vulnerability within a team.

It’s very nice to suggest ideas, but it seems like we have to “change the culture regarding work culture.” What can we do as a society to make a broader change in the US workforce’s work culture?

I’d start with school and educational values. What kids learn in U.S. schools is largely not what will make them functioning and productive members of society. We need to take a hard look at today’s work environments and be honest about what our children can expect of their future professional lives. Contrary to today’s educational values, it’s not just about academic ability and performing on tests — although quantitative skills should now be considered essential learning. Interpersonal skills, creativity and mental strength are just as important to success in the workplace, which translates to satisfaction in the workplace.

We should talk to kids about embracing optimism. For most people, it’s a mindset and a choice that should be acknowledged as such. Choose to be happy and work at achieving it.

I also think that hiring people with diverse backgrounds and nationalities makes for a more trusting environment without small mindsets. I’d love it if most American kids took gap years in other countries and could learn firsthand how other people live. At the same time, they’d probably recognize what incredible opportunities we have here and value them all the more. I’ve lived and worked in Europe, Asia and the Caribbean and that global experience has certainly shaped my professional mindset and management style.

How would you describe your leadership or management style? Can you give us a few examples?

My personal leadership style is hugely self-reflective and I’m constantly gathering feedback and insights from my peers and team. There are always personal deficits to recognize and improve, but at the same time I have preferences around time management and workflows that I know would be difficult for me to radically change. For example, I try not to have a lot of meetings. I prefer to use email to sort out problems and phone conversations to make decisions. I’m not a caretaker of employees, and I like to give people the tools they need to do their jobs while I’m out in front evangelizing the business. Admittedly, that dynamic can lead to a situation where I’m focused on the big picture while the team is stuck in the details, and I can do a better job of remembering that sometimes. I like to promote talent from within and especially recognize where people are better at certain things than I am. In those cases, I step back and give them the authority to be in control of what they do best.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’ve been extremely fortunate to have many invaluable mentors over the years who’ve guided me through the industry and given so freely of their time. Most recently, though, Laurent Paulhac has become a hugely important influence on me and the company. Laurent is a successful entrepreneur in the finance industry who is also genuinely warm and insightful. The weight of his words is extraordinary and I value his opinions immensely.

The story of how Laurent agreed to mentor me is a great one. We both happen to be interested in the obscure art of bow-hunting, specifically deer. After exchanging many emails about the business and our mutual hobby, Laurent invited me to his country home in rural New York over Halloween 2018, where he told me about a particular deer in the area that he and his neighbors had been watching for years and had nicknamed Tank, Jr. He then put me in a tree observation platform with a bow to see what I could make of the situation. After a few hours of waiting, I killed the deer with the first arrow I’d ever shot. It was a dramatic moment of fate that luckily for me, Laurent took as a sign and agreed to formally mentor me. I’m grateful for all I’ve learned from him so far and for what he’ll bring to GK in the future.

How have you used your success to bring goodness to the world?

It’s yet to be deployed, but GK is in the planning stages of adapting our voice capture technology for use in emergency services, specifically for police in the field and 911 call centers. Analyzing that data in real-time will have huge real-world benefits for first responders and potentially save lives as a result.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Einstein’s famously said that the most important question to be asked of humanity is, “Is the universe a friendly place?” I think an individual’s response to that speaks to his or her outlook on life. Einstein argued that if we agree it is friendly, we can focus on using technology and science to understand it, rather than build defenses to destroy what we perceive as unfriendly. I choose to believe the universe is friendly and that perspective informs everything I do.

You are a person of great influence. If you could inspire 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. :-)

Service should be a higher priority in our country and on our planet. It’s the most rewarding thing you can do, and the service-oriented mindset is a profound perspective to bring to all aspects of life, including work. I’d like to start a call to service on Sundays where people commit to giving a couple hours of their time to someone else. It’s a small commitment that can yield big dividends for our kids, our culture and our future.

Thank you for these fantastic insights. We wish you continued success!