10 Challenges of Live Event Staffing and Freelance Management

Putting on a successful live event means navigating hundreds (if not thousands) of moving parts. From the lights and sound to the talent and tech, every detail matters—and behind every stage, soundboard, screen, and banner is an army of freelancers and independent contractors.

Whether it’s a corporate conference, sports event, or music festival, these individuals work tirelessly to make sure the show goes on.

However, as every event manager knows, executing a live event is no small feat. The mix of physical labor, digital work, and the ever-present possibility of “act of God” situations (hello, sudden hailstorms) make it uniquely challenging.

And when you add in tight deadlines that can’t move, sourcing talent, juggling schedules, and finding a replacement for that no-show, it becomes clear why live event staffing is considered an art and science.

“With so many moving parts in an on-the-ground event, so much can go wrong,” shares Mandy Johnson, Production Services Director at Jack Morton. “We need to make sure that we’ve got people who are ready to roll with the punches.” 

While there are challenges to live event staffing and freelance management, there are also solutions. Below, we’ll walk you through the biggest obstacles and how a freelance management platform like Worksuite can turn chaos into a well-oiled machine.

Live event production is a high-stakes game. Your margin for error is razor-thin, and the pressure is on. However, once you know what you’re up against, it’s all about coming up with a game plan for leaping hurdles and keeping the production going.

Finding the right talent on short notice is one of the biggest headaches in live events production. With tight deadlines and high expectations, you can’t afford to waste time sifting through endless resumes or dealing with no-shows. You need qualified professionals who can hit the ground running.

Fortunately, an FMS platform can help you match the perfect talent—fast. Worksuite lets you post new opportunities to your internal job boards and get notified about who is available and interested. Surface your top contractors quickly—from event managers and coordinators to A/V pros and photographers to bartenders and servers.

Make staff shortages a thing of the past.

Onboarding a large number of freelancers can be a logistical nightmare. From signing contracts and NDAs to collecting tax forms and personal information, the manual process can be incredibly time-consuming and prone to errors.

Worksuite simplifies this process by automating onboarding and document signing. You can streamline everything from contract distribution to tax form collection. Jack Morton uses Worksuite to manage over 600 contractors, and our onboarding solutions have dramatically accelerated their processes.

“We saw results on day one. Our onboarding time is faster, it’s more efficient. It forced us to rethink how we want to workflow people to make it a better experience for them, and to make it faster and easier for us.” — Mandy Johnson, Production Services Director

Manually performing background checks and ID verifications can be cumbersome and slow—especially if you’re dealing with hundreds of freelancers and independent contractors. However, you can’t compromise security and reliability in high-profile live events.

Worksuite integrates background checks and ID verification into the platform to make it easy to vet your freelancers quickly and efficiently. With everything centralized, you can verify identities, conduct background checks, and guarantee all freelancers meet security requirements without the typical hassle.

Managing insurance requirements is about as exciting as it sounds, but your contractors need the necessary workers’ comp and general liability coverage to protect your event from potential risks. It’s not fun to think about, but mistakes happen—and sometimes, people get hurt. Insurance keeps accidents from turning into catastrophes.

Maintaining compliance with local labor laws when classifying freelancers can be a legal minefield. Misclassification can lead to fines, penalties, and legal disputes. It’s not something you can afford (literally) to get wrong—whether you’re dealing with IR35 classification in the UK or 1099 compliance in the US.

Worksuite simplifies worker classification by providing a streamlined AOR (Agent of Record) service and expert guidance to guarantee compliance with local labor laws. The platform helps you correctly classify freelancers and independent contractors to reduce legal risks and protect your business from potential misclassification penalties.

Related: How Identity Manages 3,000 Freelancers for Mega Events Like The Coronation of HM King Charles III

Live events often require niche skills, such as AV technical expertise or drone videography with specific certifications. Finding and onboarding freelancers with these specialized skills on short notice can be downright challenging.

Worksuite makes it easy to find freelancers with the specialized skills you need. The platform allows you to filter your search by skill set, certifications, experience, rates, availability and more—to quickly connect with the right professionals.

Plus, re-engagement becomes easy when you have an organized system. The last thing you want is to have to go back to the drawing board when sourcing talent for your next event. By streamlining and automating away most of the administrative work, and maintaining a smart dynamic rolodex, you can stay focused on building long-term relationships and producing stellar events. 

From setting up equipment to coordinating schedules, a lot of nitty-gritty tasks need to be done. Missing just one can have a huge domino effect. What’s more, the live event has a very hard deadline. It’s happening on X date—whether you’re ready or not.

You need a centralized location to stay on top of all your freelancer onboarding, assignments, documents, and progress. 

Worksuite’s project management tools help you stay on top of every task and deadline. The platform allows you to assign jobs, track progress, and manage timelines all in one place.

Live events are vulnerable to unpredictable “act of God” situations:

The list goes on and on. These unexpected disruptions can throw even the best-laid plans into chaos.

While Worksuite can’t stop the rain from calling (we wish we could), it can help you navigate the unpredictable by allowing you to make quick adjustments with flexible resource management. The platform allows you to rapidly source backup talent, reassign tasks, and communicate real-time changes to your team.

Paying invoices across different countries and currencies can be a logistical headache. However, you need to stay on top of timely, accurate payments to maintain trust and relationships with your contractors.

Worksuite automates the contractor payment process. It integrates with your finance systems to allow bulk invoice generation, track approval statuses, and process payments in multiple currencies.

If your live event is taking place abroad, with talent from different countries, we’ve got you covered.

Coordinating a mix of in-person labor, digital services, and hybrid freelancers adds another layer of complexity to event management. Not only do you need to keep up with these different workflows, but you also need to empower your teams to collaborate and communicate with all these different groups.

The types of contractors you’ll engage on a live event can vary significantly: 

The list goes on. 

Worksuite provides a centralized platform to organize and manage all types of freelancers—whether on-site, remote, or a combination of both. The integrated platform keeps everyone aligned and productive with bulk communication features, automated onboarding workflows, task assignments, and progress tracking.

Navigating the complexities of live event staffing can feel like juggling flaming torches while riding a unicycle—and if that’s actually part of your event, then you might have even more challenges. From sourcing specialized talent on the fly to guaranteeing timely payments and managing unpredictable challenges, the demands are high and the stakes even higher.

Fortunately, with the right tools, you can turn lemons into lemonade.

Worksuite provides an all-in-one platform to streamline every aspect of your live event staffing and freelance management. Finding talent, onboarding freelancers, managing tasks, maintaining compliance, automating payments—it does it all. Learn more about why experiential branding teams like Jack Morton, Identity, Freeman, and FloSports trust us with their contractor management. Want to get some hands-on experience? Start a free trial and see all the functionality for yourself.