Known by many as “Digital Dan,” Dan Massey is a master at aligning strategies, reducing silos, and ensuring technology is not just an enabler but a driver of business value.
In leading a 5,000-person organization responsible for technology, digital, data and analytics, and enterprise operations at Regions Bank as chief enterprise operations and technology officer, Massey has a unique ability to bridge technology, operations, and innovation at the highest level.
On a recent episode of the Tech Whisperers podcast, we explored Massey’s many leadership talents. Afterwards, we spent some time talking about another important influence on Massey’s approach to technology leadership: music.
Considering that the structured logic of coding, problem-solving, and system architecture often mirrors the rhythms, harmonies, and improvisations of musical composition, it’s not surprising that a significant number of technologists are also musicians. The creativity, discipline, and pattern recognition required in both fields reinforce one another.
Massey is a prime example of this dynamic duality. By day, “Digital Dan” leads a sprawling team responsible for ensuring operational excellence. By night, “Danny” Massey channels his creativity into writing, producing, and performing music. His ability to balance these two realms speaks to the deep connection between technical leadership and artistic expression.
Leading a large-scale organization in a fast-moving environment requires the ability to think both analytically and creatively. Music provides a mental and emotional counterbalance to the pressure cooker of executive decision-making, as well as a complementary force that enhances Massey’s leadership, sharpening his ability to listen, collaborate, and inspire.
In our discussion after the show, we took a closer look at the interplay between Massey’s two worlds. What follows is that conversation, edited for length and clarity.
Dan Roberts: How does your experience as a musician shape your leadership style, particularly when it comes to collaboration and teamwork?
Dan Massey: I started as a bass player and spent many years anchoring bands as part of the rhythm section, which provides the foundation of the song and drives it forward, allowing the front person — the lead singer and/or guitarists — to do their thing. Playing in a band, orchestra, or choir is the height of teamwork and collaboration. Everyone knows their part and executes it well. Beyond the technical proficiency, there’s also a chemistry to this: When a band is truly in sync, there’s a magical quality to the sound.
The experience of playing music and performing in bands has directly influenced my leadership style. A big part of my philosophy as a leader comes down to listening, collaborating, and working hard to perfect our craft, as well as leaning into professional chemistry to create a uniquely capable team and continually enhance our overall performance. For example, leveraging quality data and analytics allows us to deliver more personalized experiences for our customers whether they are in the digital channel or working with an associate in the contact center or branch. Each member of the team is leaning into their expertise in a way that complements the other, ultimately creating a unique and positive experience for our customers.
Technology leadership requires both precision and creativity. How does music help you balance those two elements in your work?
Technology and music share a critical relationship between precision and creativity. On the music side, writing a song and doing the musical arrangement requires creativity within some established constructs. For example, there are elements of song structure, such as a verse, chorus, and bridge, and mathematically driven beat structures that dramatically affect the nature of the song. The combinations result in common themes and patterns, yet when you add in vocal melodies and lyrics, you have an unlimited ability to create unique variations. Once you have the song constructed and arranged, the execution needs to be precise.
I find these same concepts relate directly to the strategy, design, and execution of technology projects. There is a tremendous amount of creativity on how business strategy, process engineering, data and analytics, software, and hardware all come together to solve business problems and meet customer needs. Once designed, these solutions have to be secure, scalable, and highly available. As a result, precise execution is critical. Being on beat and hitting the right notes is the product of many takes in the recording studio, just as writing and testing code is critical to ensuring the final product is the highest possible quality.
At the same time, playing music in a band and leading a technology organization both require continual attention and adaptability. In music, that might come in the form of improvising and responding to the dynamics of your bandmates during a live performance. You have to be nimble in those situations, and it takes a lot of practice and experience to build your chops and be able to listen and adjust in the moment. This is something we’re all too familiar with as technology leaders. Especially with the speed of change and innovation, you have to make smart calls under pressure and be able to navigate quickly evolving business priorities, unexpected challenges, and new opportunities.
Does playing music help you process complex problems and see patterns differently? If so, how?
One of my favorite aspects of music is the ability to ‘hear’ different parts to fully arrange a song. With the core guitar/piano and vocal tracks, I enjoy imagining in my mind the sound of other instruments and/or harmonies that will fulfill the true potential of the composition. Sound engineering is essentially the technology of music. It goes deep into how to capture sounds (via microphones and pre-amps), how to apply processing to tracks (via reverb, compression, equalization, etc.), and mixing and mastering the composition. This is the true intersection of art and science, where complex patterns and tools, finely tuned, can make or break the final product.
This is also my favorite aspect of my role as a technology and operations leader — the ability to understand the business strategy and see patterns and opportunities across technology, digital, data and analytics, and operations to “build” a creative solution that will meet customer and business needs. Just like in music, it can be quite complex, and the details can make or break the solution. It’s an extremely challenging and rewarding puzzle to solve.
The world of banking technology is high-pressure and constantly changing. Your former boss Anil Cheriyan was curious how music helps you stay centered and manage stress.
For me, perspective is an incredibly valuable thing. These jobs can be very stressful, and it’s easy to get tunnel vision on the problem or challenge of the day or grapple with the strategic
implications of long-range decisions. I find music to be a reminder that the world is broader than the problems of today.
I also love that music is a universal language. It transcends borders and language, it evokes emotion, and it becomes a time capsule of memories and associations. As a result, music refocuses me on relationships and connecting with others outside of having to solve problems — even though I do love to solve problems. And that helps me constructively manage stress and bring perspective to my day-to-day engagements.
If you could design a leadership workshop based on lessons from music, what key takeaways would you want participants to learn?
Most good music is produced through collaboration and teamwork, whether that’s the writing of the song itself or the arrangement and performance of studio recordings or live performances. So a great leadership workshop would be to write and arrange a song as a team. This is a collaborative process that requires you to park your ego and truly listen to and incorporate constructive feedback: Maybe this chord progression or transition could sound better, this lyric makes more of an impact, this instrumentation will complement the melody. The process also requires the ability to provide this feedback in a positive context with positive intent. The end result will be something the team will be proud of and that will connect with the listener.
These lessons are fundamental to great leadership and the ability to create and retain high-performing teams. I always say a member of the senior leadership team wears two hats: The first hat relates to their direct area of accountability — leaning into their area of expertise and executing well. The second is a leadership hat that cuts across all areas of our tech and ops organization to guide the cohesive unit as a team. Learning to park egos, receive feedback on your part even if others may not know it as well as you, and synthesizing this into more effective strategy and execution is a great parallel.
Ultimately, great bands and great IT leaders know that big hits are built on collaboration. It comes down to the interplay and ensemble work of listening to each other, staying in sync, and complementing each other’s roles. The instruments may be different — in IT, your orchestra consists of developers, engineers, cybersecurity experts, and business stakeholders — but the principles are the same. If any one part is out of sync, the whole performance can suffer.
What kinds of music do you most like to play and listen to? Can you share two or three of your favorite bands?
This is a hard question to answer. I love all kinds of music, but when I play music, I tend to lean into the singer-songwriter genre, meaning acoustic-based songs with a lot of vocal harmonies. I have a group of very close friends that I’ve been writing songs and playing with for over 30 years, and I cherish the opportunity to perform with my daughter, Riley, who is a talented violaist and has a beautiful voice.
I could list dozens of bands that have influenced me. If I had to pick some of my favorites, I would encourage people to listen to Ruston Kelly, Gregory Alan Isakov, and Rob Williford, who co-wrote a number of songs with Luke Combs and has some new projects coming out soon. I also suggest listening to Lilah Moons’ debut album 18 Years. She is a very talented new artist, and I had the honor of producing her album and releasing it last September.
For more from Massey on tech, banking, the power of translation, and the art of leadership, tune in to the Tech Whisperers podcast.
See also:
Read More from This Article: How music shapes Dan Massey’s approach to IT leadership
Source: News