Courtney Jackson Says Live Events Have a Skills Problem That Training Manuals Cannot Solve

A delayed opening, an unhappy artist manager, or a sponsor guest who suddenly cannot access the right ticket can change the tone of an event in minutes. Courtney Jackson has spent her career working in those moments where the technical plan matters, but the person responding to the problem often matters more. After years in music touring, global sport, and premium hospitality, she has become increasingly concerned that younger professionals are entering live events without enough chances to develop the interpersonal judgment the work demands.

Jackson sees the issue as larger than whether someone knows how to run a schedule or follow an operational process. Live entertainment depends heavily on emotional intelligence, she says, particularly when circumstances change in front of a crowd, a client, or an artist team. Junior employees can learn the logistics of a tour or event relatively quickly, but the habits that shape a career are harder to develop without observing experienced people navigate pressure in person.

"You can teach someone the mechanics of an event much faster than you can teach them how to read the room," Jackson said. "The difficult part is knowing when to speak, who needs information before they ask for it, and how to stay useful when everyone else is stressed."

Her concern has grown alongside changes in how younger employees enter the workforce. Jackson argues that remote work has reduced the amount of time junior professionals spend in the rooms where interpersonal skills are learned informally. In her view, someone beginning a career from behind a screen misses small but consequential lessons: how senior operators communicate, how problems are escalated, when a conversation should happen privately, and how relationships are built with people whose names may never appear at the top of an organizational chart.

For Jackson, the gap between technical competence and professional judgment shows up in the advice she gives younger operators. She advises juniors to communicate upward before being asked, build relationships with crew members others overlook, and volunteer for the unglamorous operational work that gives them more exposure to how events actually function.

"The person everyone trusts at an event is usually not the loudest person in the room," Jackson said. "It is the person who notices what needs doing, follows through, and does not create more chaos when something goes wrong."

Jackson's perspective comes from years spent managing teams and operations across major music and sporting events, including the Super Bowl and FIFA, as well as music tours for the likes of Katy Perry, Bon Jovi, and Eminem. Her experience has taught her that live events leave little time to deliberate once a problem becomes public, particularly when doors are opening, guests are arriving, or a client needs an immediate answer. That environment has reinforced her view that emotional intelligence should be treated as a professional skill that can be developed rather than an innate quality some employees simply possess.

She also places unusual weight on reliability. Jackson argues that attention to detail and doing what someone promised can separate an employee from the people around them. Her advice to younger professionals is to keep learning while they work and to pay attention to the parts of the job that receive little recognition, because those assignments often expose them to the decisions and relationships that shape larger events.

Jackson has begun formalizing some of those lessons through training and mentorship. During the FIFA World Cup 2026 cycle, she delivered 38 training sessions for teams across the tournament. She serves as a judge for the Stevie Awards for Women in Business, works with the UK-based Event Academy on developing new entrants to the industry, and formally evaluated master's teams at Pepperdine University's Graziadio Business School, which developed a graduate case study on her company. She also mentors a number of younger operators one-on-one, most of them women building careers in live events.

Her focus on development is especially strong when it comes to women entering live entertainment. Jackson has spent much of her career in music and sport, fields she describes as heavily male-dominated, and she is particularly interested in mentoring younger women entering those environments. Her own experience has convinced her that seeing more experienced professionals navigate the industry can affect whether junior employees can picture themselves advancing within it.

"People coming into the industry need to see how experienced operators actually work," Jackson said. "For young women especially, having someone further ahead who will explain the parts nobody teaches you can make a huge difference."

Jackson also sees the talent question becoming more important as technology changes other parts of work. She expects automation to increase the value of in-person experiences because people will continue to seek real human interaction as more daily tasks become mediated by technology. That puts additional pressure on live-event agencies to protect the interpersonal skills that make those experiences feel human in the first place.

Her argument is ultimately practical. Technology can make parts of event work more efficient, but Jackson does not believe it removes the need for people who can interpret a situation, manage emotion, and respond effectively when circumstances change. She believes those abilities can be taught, provided younger professionals have opportunities to observe them, practice them, and receive guidance from people with more experience.

"The future of live events depends on people who know how to work with people," Jackson said. "If we stop creating places where young professionals can learn that, we will eventually feel the loss across the entire industry."