Ask a Former Assistant: Billy Gleeson (The Late Show withStephen Colbert)

Billy Gleeson,

Former Production Supervisor at The Late Show with Stephen Colbert

Hi Billy! Thank you so much for taking the time to speak with us.

Tell us more about what it was like to work at The Late Show (for 6 years, wow!). What was your day-to-day as a Production Supervisor?

Working in Production, no two days are the same.  The easiest way to describe the role of Production Supervisor at The Late Show was “Air Traffic Control”.  So many departments are trying to launch projects at the same time but Team Production was there to make sure no one was bumping into each other and everyone had all the resources necessary to succeed.

Supported by our Production Coordinator, Assistant Production & Office Coordinator (APOC), and our team of Production Assistants, we were there to provide everything from stage time and personnel to catering, transportation and everything in between.  The key to success was building a fantastic team with a completely diverse skill set who were happy to hop in no matter how big or small the task.  We never knew what challenges a day might hold but a team prepared for anything kept us all at the very top of our game.

Looking back, what stands out as your favorite part of the job?

Managing the internship program.  We had the opportunity to bring in incredibly talented candidates every semester who often went onto jobs at the show, similar productions, or even outside pursuits they were passionate about.  Getting to work with each of these people was a delight and I’ve been lucky enough to remain close with many of them as they continue to grow in all corners of the business.  

Alongside our Production Coordinator, we also initiated relationships with outreach organizations such as GyrlWonder, Ghetto Film School, Veterans in Media and Entertainment, and Lights! Camera! Access! who all support underrepresented communities trying to get into the business.  We began dedicating 50% of the spots in our internship program to these groups and discovered some of our most outstanding talent through these great companies.

You have quite the impressive background in live programming – Conan, NBC Sports, and of course, Colbert. What draws you specifically to live television?

Live television doesn’t give you too much time to overthink.  Whether it’s a taping in front of a live audience or a major sporting event, you have a start time that (for the most part) cannot be moved.  You operate within a pressure cooker and just have to get to the finish line no matter what breaking news story, logistical constraints, or sudden issues may occur.  One thing I know about myself is that I have a tendency to overthink and over-prepare, a luxury that live television takes away from me.  

I never specifically intended to build my career in live television but I think that adrenaline rush and the deadline being out of your control is why I’ve been drawn to this part of the industry for as long as I have.

Once upon a time, you were a Production Assistant at The Late Show. You then rose the ranks considerably. What do you think led to your success? And what lessons from your time as a PA served you later on in your career?

Luckily, I was one of many who found themselves climbing the ladder at The Late Show.  Multiple people who started production assistants, pages and interns have gone onto success at the show in a wide array of departments.  If I was to pick up on any common thread among those people, it was flexibility.  People willing to hop in and lend their talents to multiple teams as opportunities arose often found success a little quicker than those who had tunnel vision for one specific role.  You never know when the right opportunity might arise so presenting yourself as more of a Swiss Army Knife will often open more doors.

For anyone starting out as an assistant in the industry, I would just say to always work to be the best version of yourself in each job you’re given.  Treat every staff member with the same level of respect, no matter where you go and don’t forget where you came from.

Is there anything you know now that you wish you knew earlier in your career?

Networking is a necessary evil.  I guess I did know it and was told “network, network, network” through my college days but I really underestimated the importance, nor did I have any clue how to do it well.  Through trial and error over the years, I’ve discovered the best approach is to: 1/ Make it about them.  We television industry folks LOVE to talk about what we do.  If you send a message just telling us who you are, there’s little reason for the person on the other end to be engaged.  Make sure it’s a two-way street.2/ Look at it as building a friendship.  People who try to be anything but themselves usually come up short so make it conversational and intermittently send messages to stay in touch.

3/ Get in contact BEFORE the job opening becomes available.  Start looking at shows or productions you like and find people there who you might be able to chat with.  Wait until you see an opening to start networking and you’re likely getting buried in a sea of messages of others doing the same thing.

4/ Network with people at your level.  Too many people go after the biggest dog in the yard - an Executive, a Writer, a member of Talent.  People currently in assistant roles are way more likely to want to chat, help, and not be buried in messages of people asking for the same thing.

What advice would you give to Hollywood assistants – Executive and Administrative

Assistants as well as Production Assistants – who hope to achieve similar career success?

See above, haha.

You were previously in charge of hiring decisions for Colbert’s internship program. What do you look for in candidates?

While it’s not a hard and fast checklist, I’d say the key elements we looked for in the hiring process are:1/ Personability.  This is the case for absolutely any job.  We’re going to be spending a lot of time together so would I enjoy working with you?

2/ Preparation. Has this person shown up dressed for an interview or like they’ve rushed here between errands?  Do they know the show and have they come up with some informed questions about the process?  If it's over Zoom, have they checked everything works or am I going to be spending the first five minutes messing with cables?  All these things are a sign of how you would be on the job.

3/ Professionalism.  Someone who comes in “fanning out” over the process and barely being able to keep themselves together is a liability.  Keep your head and dial back the fandom in the room. 

Did / do you have any mentors in the industry? If so, how did you seek them out?

I’ve had different mentors for different times.  Fortunately, I’ve stayed in contact with all of them but I won’t name names in order to save their inboxes.  They’ve naturally developed from job-to-job and sometimes it’s people I’ve sought out, other times I’m lucky enough to have people who have seen something in me.

For those I’ve sought out, it begins as networking.  You ask for 15-20 minutes of their time, sometimes it goes nowhere, but other times it just clicks and you’re onto something.  Could be a producer, executive, writer, crew member - you truly never know so make sure to be kind to everyone because the next person ready to help out could be right around the corner.

What’s up next for Billy Gleeson?

I’ve taken some time off to work on getting back to my stand-up and creative career.  Hopefully a lot more of that is in my future and I’m currently developing some content that I look forward to sharing with people soon.  Right now, I’m just thankful for the journey that has got me to where I am and looking forward to what’s to come.