7 Tips to Progress Your Career from CIO Orla Daly

March 30, 2022 | New Workplace Leadership | 10 min read

When I first met Orla, I immediately noticed her Irish accent. It drew me in, and I wanted to know more about how she came to live outside Boston, Massachusetts. It wasn’t long before my curiosity about her travels was taken over by my desire to learn from Orla. She has an almost immediate ability to draw you into conversation and a natural talent for putting you at ease — skills that have served her well throughout her career.

As I got to know Orla, I asked about her early days. If you read, Chief Information Officer (CIO) in her title and imagined a childhood of chess matches and late nights playing with code, you are in for a surprise. Orla’s unconventional path to technology is a hint into her deepest motivators and the strengths she brings to her profession. It’s grounded in relationship-building and an adventurous spirit that believes anything is possible.

For as long as she could remember, Orla had a thirst to explore the world. She began to quench that thirst by studying French and German in college — not exactly the educational foundation one expects from a CIO, but one that proved valuable.

Orla saw language studies as a ticket to leave Ireland and a way to better understand others. She considered leveraging her language skills to parlay a job in marketing after graduation, but that didn’t feel right. Instead, she took a step that in hindsight would trigger an unexpected but satisfying career.

Orla, enrolled in a master of information technology degree program in Scotland. From what she describes, I’m not sure Orla knew how much she’d feel at home in the program – but what’s certain is she knew it was a chance to keep learning and it felt like another adventure.

Living in Scotland, Orla got her first taste of how technology could change lives. She was drawn in by her first healthcare application. She developed a system to visualize cancer in the human body. It hooked her on using technology to make an impact. Perhaps for the first time, her master’s program was more than a way to go on adventure, it became a way to ground her professional life.

Joining Exxon in the UK, Orla began to feed her wanderlust. She took advantage of their global footprint and got assigned to France. Two years later she moved to Belgium. It was an incredible career move for Orla. She was in her 20s having fun and felt the joy of her freedom. At Exxon, her business acumen and technical training made her the perfect liaison between functions. She began mastering the integration of technology and business to drive value..

In 2005, after getting married, Orla moved to the United States and was ready to build roots in one place. The transition to life in New England came more easily than she had expected. Soon she felt grounded in her new home.

Yet, her drive to learn from new people and about new places didn’t go away. It simply changed form to match her current life. Today, she and her family enjoy taking vacations in places they have never visited before. Although there is one place, Acadia National Park in Maine, that draws the family for frequent return camping trips. There is something magical about the disconnection from day-to-day life that you experience surrounded by the crashing ocean waves on rock. She finds rejuvenating energy in nature. Stepping away from technology is just the break she needs to come back with inspiration.

Throughout our conversation, I was struck by the important lessons Orla shared. Her reflection was clear proof that she’s committed her life to growing – personally and professionally – in a way that betters others around her. She wasn’t shy about sharing what her journey has taught her:

Build trust and understanding

When Orla told me, “I really want to understand the business and the needs of our customers,” her conviction was clear.

She advocates constant curiosity by asking lots of questions, but also really listening to what others express because that is the foundation for building trust with your peers across the organization. Without trust, you can’t make an impact.

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Focus on the outcome not the output

It’s tempting to get caught up in the plan. Moving through the to-do list, meeting deadlines, focusing on the output, staying on budget. We can’t let ourselves get lost in all the work, we must remain focused on the impact that work is meant to achieve.

Flex your empathy muscles

Seeing a problem or an opportunity through the lens of others is incredibly insightful and helps bridge functions together. It may seem hard at first, but simply taking a moment to pause and reflect before responding can provide the space to do this well.

Embrace diverse points of view

One of the joys of being a CIO is the interaction with people across the organization. Each brings a unique point of view. It takes effort to get to know your team, but that effort always pays off. When we drop our expectations that everyone must show up in a specific way, we open the door to innovative solutions and new ideas.

Knock down your defensive walls

In order to be effective, hard conversations need to take place. It’s critical that you allow a safe space for those to happen. That means showing your vulnerability and accepting the feedback being delivered, so others will model your example.

Resist the temptation to type cast

A complex, global organization is like a puzzle. We have to understand how all the pieces fit together to form a whole. We can’t do that if we don’t explore the attributes of each puzzle piece. The same is true for our people. We need to see their skills, but also their personalities.

Be your most vigilant customer

One of the best things about working for Skillsoft is that every single employee can use our products. By using our own solutions to advance our people, we not only improve employee satisfaction and optimize performance, we make better products for our customers.

Throughout my conversation, Orla made me smile often. So, it’s no surprise that before we wrapped up, she shared one last, important lesson:

Don’t forget to have fun!