Undercover Boss Analysis of Stephen J. Cloobeck: CEO of Diamond Resorts International
Name: Stephen J. Cloobeck
Title: CEO of Diamond Resorts International
Headquarters: Las Vegas, NV
Product or Service: Hospitality and Vacation Resort Brand
Brief Overview:
In this week’s episode of “Undercover Boss”, Stephen J. Cloobeck, CEO of Diamond Resorts International, goes undercover to gain perspective into the lives and jobs of the employees at his company.
Analysis
Quite the disguise.
Position 1: Resort Engineer
Overview: Stephen Cloobeck goes under cover as “Jack Fisher”, assist Randy at his first trial position of resort engineer. He stands by with a fire extinguisher as Randy welds a broken AC unti on the building rooftop. He later helps Randy replace old lights with new standard Diamond Resorts lights.
Result: A small fire breaks out, but the pair is able to contain it. Cloobeck overcomes his fear of the ladder (not the corporate one, that’s for sure). Cloobeck learns that Randy once owned an RV repair business, but the company that purchased it owed Randy 240k before declaring bankruptcy. Randy and his wife are now forced to work two jobs to prepare for retirement.
How he made amends: Cloobeck awards Randy $150k to pay off his entire mortgage, and throws in an additional $50k in cash as icing on the cake.
What he should have done: Cloobeck really didn’t change anything about this role in particular, but in this short segment, you would be hard pressed to find even one real job related issue. Our first thought was lack of safety while welding the roof unit, but they did have a fire extinguiser and wet cloths (I’m not AC technician, but that sounds reasonable).
Cloobeck earned some major generosity points by paying off Randy’s mortgage. He also had his own share of business deals gone bad, so this act really brought his empathy to the spotlight.
"Damn, I knew we should have used Priceline."
Position 2: Booking Agent
Overview: Stephen listens in as Sarah answers calls from customers looking to make reservations at various locations.
Result: Sarah makes a number of painfully apparent errors – such as not spelling a destination location correctly in the system, preventing her from providing potential reservation dates. After about 4 in a row, Cloobeck explodes, reveals his identity, and marches directly to Sarah’s supervisor. He is displeased with their training, to say the least.
Doing his short stint as a booking agent, he learns that Sarah is working towards a business degree in college, while working for Diamond Resorts.
How he made amends: Cloobeck first apologizes, stating that it is not Sarah’s fault for her lack of proper training. He states that he will now be personally training each team member at the facility. Cloobeck awards Sarah and friend a first class trip to Hawaii (hoping she will learn the Hawaiian resort names, half jokingly), and pays her $15k, to cover her school loans.
What he should have done: Was it actually the entire team booking agents who required training, or just Sarah? That’s the real question. Either way, a CEO of a company this size has got to have better things to do than spend time retraining the entire squad of booking agents.
Cloobeck should have pressured their direct managers to improve their performance and training, and setting some new standards. It’s their job to train the agents – not the CEO’s.
Raisin' the roof. Well, sanding it at least.
Position 3: Painter
Overview: Stephen follows Greg from building to building, performing various touch-ups, such as sanding down walls to be repainted, and calling in leaks to the technical team.
Result: The job itself is relatively unpleasant – Greg is forced to use a hand sander on the ceiling, rather than a power sander, which adds considerable time to the job. The safety glasses and masks they use are on the lowest-of-the-low-end of things, and make it difficult to see/breath.
Greg notes several difficulties with the job, specifically the fact that there are hundreds of buildings for each employee to monitor, spreading them very thin. He also notes his displeasure with the fact that he had been there for several years with no pay increases. Cloobeck learns that Greg enjoys cooking on the side, and because he has car trouble, has trouble making it to work.
How he made amends: Cloobeck states that he will be upgrading the safety googles and masks, as well as providing electric power sanders, to assist Greg and the other Painters. He says he will work to improve the staffing issues. He enrolls Greg in a “meat of the month club” (it’s like Clark Griswold’s “jelly of the month club, but with meat”), and buys him an industrial freezer. Additionally, Greg is given a new hybrid truck, and a $20k cash bonus. Cha-ching!
What he should have done: New power tools for better efficiency? Check. New goggles and masks for better safety? Check. New employees for better staffing? Check.
Cloobeck aced this round, and his added generosity did not go unnoticed.
"...And this is where the overbooked reservations go!"
Position 4: Front Desk
Overview: Amanda shows Stephen how to work the front desk at one of the resort locations, checking people in and out.
Result: Stephen is shocked to see that the front desk was still using an archaic hand written paper system for scheduling and bookkeeping. Amanda describes her displeasure in how they are told to deal with overbooking – they are essentially told to inform the customer that an unfortunate maintenance issue is preventing them from assigning the room. Apparently, several customers didn’t take this so well.
Cloobeck learns that Amanda’s mom has multiple sclerosis, and Amanda is struggling to chip in with her medical bills. Amanda states that she would go to Ireland, if she could go anywhere.
How he made amends: Cloobeck says he will be changing script used to deal with overbooking situations, specifically by proactively contacting customers much earlier to let them know of overbookings and provide new arrangements. Amanda is offered a position to work in Ireland, and is awarded a $50k cash bonus.
What he should have done: Stephen Cloobeck nails the overbooking problem, but fails at the easy layup – the paper based bookkeeping system. He even says himself “C’mon, its 2010!”
Cloobeck, get back in there and upgrade this site to a modern day scheduling and reservation system. Ditch the paper, save some trees, and make it easier on your employees at the same time.
Grade:
For the most part, YES.
Stephen Cloobeck earned a “B” grade for his appearance on Undercover Boss.
Admittedly, it was within inches of an “A”, considering his generosity - but you can’t buy your way through this test. He missed the necessary IT upgrades for the front desk team, and took a rather unorthodox approach to the training issues of his booking agents.
Finally, the one side note that cemented him in “B” territory was the fact that he opted not to stay in a low grade hotel while away from home, and instead stayed in a fancy 5 star hotel. A minor detail, but still – to get the truest sense of what it might be like not to be CEO, he should have lowered his standards a bit just for that week or so.
Don’t like our grade? Drop us a rebuttal, and leave a comment below.
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Since its debut on CBS, I have watched a majority of episodes of Undercover Boss. I was amused by Mr. Cloobeck’s arrogance and conceit. He was cavalier regarding his wealth and position, taking pride in himself rather than in his deserving employees. His overblown assessment of his abilities, as well as his properties, was ‘uncovered’ as he demonstrated his incognizance of the day-to-day operations of DRI properties.
Anyone else think his wife married for love? womp womp
Cloobeck was truly an arrogant narcissistic dick. This show was really him taking the opportunity to flaunt his wealth and make sure he was scene. I think he just wanted also to advertise his product.
He has purchased his wife, not sure if he’s humble enough to actually know that though.
Wow, this guy is a the king of all doosh bags. How about that violation of HR policy by calling that call center rep “babe”?
Wow, this guy is a total tool.
A tool? Perhaps, but he sure was a generous one.
I was so looking forward to the new episode however I turned it off after the first 5 minutes or so. This CEO was way to stuck on himself and his wealth.
Agreed – a complete douche bag.
He was looking for people to kiss his a$$ and stroke his ego.
Yuk.
Funny thing is his “WEALTH is as FAKE as his TAN” His empire is made up of a bunch of unhappy members just google it if you don’t believe me.
Don P.
What a total douche bag, my favorite part was the very last scene of him in the hot tub or whatever with a glass of champagne, so humbe. I’m actually glad I saw that episode now I will never stay at one of his resorts.
I’m a unfortunate owner of points in Diamond resorts, so the doosh bag was throwing his money about, well owners money really! As one of his first great moves on taking over the company was to practically double the maintenance fees.
I’m in the UK so we cannot see the us ‘Undercover boss’ but he looks to be a bit odd ( plastic surgery on the eyes ect??)
Can someone put this episode on u-tube please, so we in the UK can see it!!
This man is not a nice man. The fact that the sales agent even got a second chance is surprising because on a daily basis, this company fires sales agents for reasons such as a client getting disconnected from a phone call. They hire masses of agents and train them – it takes about 3 months, and entire classes are already gone – FIRED. good thing they hire in between though to have agents to replace those that were fired for any perceived transgression. This company is not loyal to their staff and this man and his rules are heartless.
Total douche… How does he think he is soo important that he needs a personal sercurity commando doing sweeps of hotel rooms for him. He says there are alot of ‘crazies’. For him? Does he think he is some sort of celebrity? I bet no one would even recognize this guy AFTER this show premiered.
[...] hospitable side of yourself. People will follow your lead into some amazing places. Interestingly, an analysis of this CEO rated him with a “B” grade. I think what the analysis failed to take into [...]
I thought he was a man who cares deeply for his employees and really made a difference in their work loads and personal life. He lives a high life, of course, he worked hard to get there. Dont attack him personally,,,if so,,its because your jealous. I would love to work for this man.
I just watched uncover boss, never saw this program before,I was in tears for what Stephen did for all his people, what a wonderful, kind, caring, giving man he is. He literally changed the lives of these people, not to mention improving his business, which will benefit so many other people. I am 67 years old and this man brought tears to my eyes with each gift he gave, you could feel his heart. God bless him, we need more like him, what a better world this would be. He is so successful, and will continue to be, he’s smart, but not self absorbed, it’s not always about money, his heart is huge. May God keep blessing him. Thank you.
Mr Cloobeck,I just watched this Undercover Boss show for the first time and was so impressed the way you run the business.A true man of integrity,and what you did for your employees touched my heart, so special. My name is John Russo and I’m about to leave the entertainment business,where I wear many hats,specializing in keeping celebrities content and safe.I am a very personable man.I have just purchased a home in Scottsdale and I may be looking for some work,it would be my honor to be part of your team,I would like to send you a some references and tell you a little about myself or your GM in Scottsdale.I hope email gets to you,if not Bless You for what you did for your staff.
Thank you,
John Russo