RSS Feed for This PostCurrent Article

What is Your Funniest or Most Embarrassing Phone Experience? Win a $300 Headset!

Thanks for all of the great submissions to the contest. We have picked the finalists and the voting page is now up. Read the stories of the finalists and submit your vote!


Everyone has had those embarrassing or funny phone experiences we love to share. Here’s your opportunity to tell the world, and possibly win a new OfficeRunner Wireless Headset System from Sennheiser, provided by (I have one of these myself and I can tell you that it rocks!)

Here’s how the contest will work.

1. In the Post a Comment section below, describe your funniest or most embarrassing phone experience. (You’ll have plenty of space, but obviously people won’t want to read a novel.) Don’t be shy! We will accept submissions until Sunday, August 8. At that time our panel of judges will pick 5 finalists.

2. On August 9 we will announce the finalists and put up a Voting Page where you will have the opportunity to vote for your favorite. The top TWO vote-getters will win a headset. (Voters will be allowed to vote just once).

Yes, I have had a lot of both embarrassing and hilarious phone moments over the years.  One that comes to mind was in my first year of business. It didn’t happen to me, but I witnessed it. I was in a client’s office and he was on a conference call with a prospect. He had the call on speaker phone. The client was a bit arrogant…OK, kind of a jerk. (In those days I would take on anyone that would pay me). He was mocking the prospect as the prospect spoke, making faces, nodding his head, basically acting like a juvenile. He then hit the "mute" button, and said to me, "These guys are real losers, aren’t they?" Well, he thought he hit the "mute" button. There was a moment of silence, and the prospect said, "Who are you referring to as losers?" My client tried to dance around the issue, to no avail. He didn’t get the business, and I didn’t work with him long either.

Let Others Know!
Pass this on to anyone who might want to share their story, or get a good laugh. The link directly to the contest page is

Trackback URL

  1. 63 Comment(s)

  2. By Jason Beaudoin on Jul 30, 2010 | Reply

    My first ever sales job was selling promotional products. My training included being handed a phone book and my boss pointing at the phone. Needless to say I was a little nervous. The first week on the job I was calling my butt off, not having any clue what to say. So, I would introduce myself and ask to speak with whomever handled the purchasing of promotional products for the company. I got one gentleman on the phone, who after my introduction, said in a very upbeat accepting tone- “Absolutely, hang on one second I’ll transfer you right over!”. I was excited, that wasn’t usually the reaction I was getting. So as I was preparing to talk to the buyer I heard…click. That was funny I thought to myself, we must have gotten disconnected by accident. So, naturally I called back and spoke to the same gentleman. He said “Oh no, I’m soooo sorry. We must have been disconnected when I tried to transfer you.” This time, he didn’t sound so sincere. He continued on, “I’ll transfer you right over”. Click. He hung up on me again. I thought it was very funny how excited he was to transfer me, only to hang up on me twice. That didn’t instill confidence in my abilities as a new sales person, but even at the time I did think it was pretty funny.

  3. By Brett on Jul 30, 2010 | Reply

    I was leaving a message for a client last year, while leaning back in my chair and balancing a hot cup of coffee on my stomach. As I reached over to grab my notes, my HOT coffee spilled all over a. . . certain part of my body that doesn’t feel really great when a hot beverage lands on it.

    I yelled one of the seven dirty words at the top of my lungs, which went right into the client’s voice mail. I hung up, called back, got voice mail again, explained what happened and offered a sincere, heartfelt apology.

    I walked down the hall to let my CEO know what happened, so he wouldn’t be surprised when he got a complaint call back from the client. Expecting him to unload both barrels on me, he instead began laughing so hard, I thought he was going to burst a blood vessel.

    It turns out he knew the client for many years, and called him up himself to offer an apology. When the client called the CEO back, they both had a good laugh about it, we actually wound up making a sale(!), and I got my commission.

    At the next sales meeting the CEO told everyone the story, (which got a huge laugh and round of applause), and asked me if I could spill hot drinks on myself more often.

    Andy Y Reply:

    Lol. Brett. Thats a very funny experience you had. LOL. :)

  4. By Joe Catal on Jul 30, 2010 | Reply

    Several years ago I was selling Telephone On-Hold Messages. I had a follow up call to the owner named Bob. I dialed the number, asked for Bob and was connected. I started out with, hi Bob, this is Joe Catal calling you back from ABC Corp. regarding the On-Hold Messages we spoke about last Tuesday. He said he really didn’t remember the call. I said don’t you remember me playing you the short 30 second sample? He said he’s been busy and probably just forgot. I told him I’d play it again for him. He listened to my 30 second spot. When I got back on the line he said: Oh, you’re the guys that produce those phone commercials. Yeah, how much is that? I told him $495 and what we’d do for him. He agreed and gave me the go ahead. When I read back is co. name as ABC Mortgage, he said no, that’s not me. I’m XYZ Insurance agency? Real quickly I realized I had the wrong Bob on the line! I even played him a Mortgage co. demo instead of insurance! I quickly got the right paperwork out and wrote him up. He gave me his credit card info and I wrote the deal, with the wrong person. After that call called the mortgage co. and wrote that deal too.

  5. By Autumn Bostic on Jul 30, 2010 | Reply

    When I first started out on prospecting calls in my Marketing job I was so excited. One day I called a big company and asked for the CEO. The lady on the other end started to cry and said that he had died a few months ago and that his son had taken over. She requested that I talk to him but he was out on leave. I didn’t know what to say except for I am sorry for your loss and decided to just call back another time (like a few months later). I was so embarrassed I don’t think I ever called the account back.

  6. By Kevin Payne on Jul 30, 2010 | Reply

    It was my very first sales job, 18 years ago. Our sales manager came into the sales office and said, “I have dinner for two and an overnight stay at a nice hotel for the first one of you to get five appointments.” I immediately got three and was way out in the lead. Then John, the seasoned veteran sitting across from me got one, then two then three and four. I was getting desperate. I was stuck at three. I called Carmel’s Mexican Restaraunt and asked for the owner, Mike. “I’m sorry, Mike died last night.” Non - plussed, I asked who would be handling the advertising. “Mike’s wife, Dorothy,” was the reply. I, of course, then asked, “Is Dorothy in?” Needless to say, I never got any business from them.

  7. By Drew on Jul 30, 2010 | Reply

    I make mostly outbound calls, but do leave a return phone number on voicemail messages when possible. One day I was making my outbound calls when I received a return call from “Jennifer” (no company name given). For the life of me I couldn’t remember which company she was from. I made small talk while trying to find her information in my files, but just couldn’t place the name with a company. I finally fessed up, and told her that I was having one of those days, and could she please remind which company she was with. She said “Jennifer…your ex-wife…”. OOPS! I didn’t recognize her voice, and had not spoken with her in several years, so assumed she was a prospect calling me back. Didn’t make any money for myself or the company on that call!

  8. By Dan Dobson on Jul 30, 2010 | Reply

    So I am sitting on the toilet in a rest room stall at BWI minding my own business (excuse pun) when this guy in the booth next door says “How ya doing?” I was a little taken a back but being a 40 year sales veteran, I am not shy about meeting new people so I said ” Great how about you?” he says ” I have had a rough day and really need a drink” Well by this time I am thinking this guy might be batting for the other team so I said ” well there are plenty of bars around” and he said “thanks” and I said “don’t mention it”. When he then said something totally inappropriate to the strain of the converrsation it dawned on me that this guy was talking to his wife or someone on his cell phone and I was answering what he was saying to her and it happened to coincide for a short period as far as timing was concerned with his phone conversation. I obviously extended my stay in the stall well beyond him leaving and being as far away from the rest room as time would allow. You talk about being embarrassed.

    Rebecca Schwartz Reply:

    Just one more reason why cell phones should not be allowed in restrooms, LOL.

  9. By Pat on Jul 30, 2010 | Reply

    My favorite ugly sales moment was when I worked for a company that did a horrible job managing their customer info. I called for the name I was provided, and was promptly informed that the person had passed away. I realize that this has probably happened to all of us before, but what made this really bad was that the person had died 10 YEARS before I made the call. I tried to save the call by asking for his replacement, and you can probably guess how well that went.

  10. By Brian Sholder on Jul 30, 2010 | Reply

    One time when I worked at a bank’s call center I received a call from a little old lady. She could have been the sweetest lady I have ever spoken to. She told me that she was standing in front of an ATM machine and she wanted to get money out of her account. I told her she just needed to put in her ATM card punch in her pin and complete her withdrawl. She advised me that she did not have an ATM card. I told her that she needed on to use the machine. Then she replied can’t I just punch in my account number and you just push money through for me. Stunned by that comment I said, “Do you think I am standing in the machine ma’am….She replied well aren’t you??? I told her that people do not actually stand in the ATM machines and she didn’t believe me.

  11. By bill morgenstein on Jul 30, 2010 | Reply

    This goes back a number of years ago:

    I was president of a company called Kitty Kelly Shoe Co. in NY. In the days of switchboards the operator informed my assitant that David Rockefeller was on the phone. Of course I knew that it was my crazy friend joking as whenever he called me his mentioned a celebrity’s that was calling. He was totally bald with a cherubic face and you had to love him. So I laughed and said “put him on”. “Good morning skinhead I bellowed into the phone” Dead silence! “Skinhead, are you there?” It turns out it was in fact David Rockefeller who was soliciting our company to become charter sponsors of the Urban Leage. He was at the time Chairman of Chase Manhatten Bank and he was devoid of a sense of humor as I fumbled and tried to apologize and explain the mix up. Very, Very embarrassing.

  12. By Mark Kuecker on Jul 30, 2010 | Reply

    An inbound telemarketer called my home, and I always take them because they all need practice and sometimes it’s fun. Like my Discover call.

    “Mr. Kuecker? (badly butchered.) “Yes, this is Mr Kuecker. (repeated butchered pronounciation.)

    “Mr Kuecker, I’m calling with your Discover card.” To which I quickly and shortly responded, “Why do you have MY Discover card?”

    They hung up.

  13. By Robert J. Payne on Jul 30, 2010 | Reply

    Early in my sales career I worked for a small lead gen firm in Philly. One of our clients was Sun Microsystems. I was going through my daily calling routine…calling my direct dials, leaving voice mails, asking for referrals…when all of a sudden my phone rings. I had a pretty good conversion rate on inbound calls, so naturally I was pretty excited. I pick up the call introduce myself and hear: “Yea, this is Mike with XYY company. You called earlier and left me a voice mail about my son…” One hell of a way to get a call back!

  14. By David Crawford on Jul 30, 2010 | Reply

    When I worked for a local phone company I overheard a fellow telemarketer have the following conversation. I’ve filled in what the customer said, based on the reps report.

    “Would you like to buy one of our new telephones?”
    “No, I’m dying of cancer.”
    “Well, how about a rental then?”

    Sad call but the quickest wit I’ve ever heard.

  15. By Rebecca Schwartz on Jul 30, 2010 | Reply

    A large part of my job is making sales and customer service calls to radio stations across the U.S. and Canada. Several years ago, I was calling on some stations in Quebec, and it soon became apparent that it was common practice for receptionists to answer the phone in French rather than English. My standard reply to their greeting became, “I don’t speak French. Could you please speak English?” and usually they’d switch languages with no problem. But then came the day when, a bit trigger-happy, and not exactly sure of what the receptionist had just said, I repeated my cheerful request, “Can you please speak English?” … only to be met with a long pause, and a constrained voice saying, “I WAS speaking English.” Oops! Turned out that the secretary had simply answered the phone by giving the radio station’s nickname, and I had totally missed it. Needless to say, I was quite embarrassed, but thankfully the lady was quite understanding, and we moved on with the call. It has made for a good story to laugh about in subsequent years — and it taught me an important lesson about listening carefully before I speak!

  16. By Daniel on Jul 30, 2010 | Reply

    So I am cold-calling my salesforce accounts yesterday, and I felt compelled to try a new approach–a slightly warmer approach. I proceeded to call prospects using chamber of commerce business directories and opening up with, “My name is Daniel and I am considering joining the chamber of commerce, so I am reaching out to other chamber members to introduce myself…”. People were incredibly receptive and many an appointment was set, until…
    A man answered the phone and stopped me mid-sentence to let me know he was onto me and that “meddling with the chamber of commerce will wind me up s#%$! creek without a paddle”. He accused me of impersonating a chamber member and continued to berate me with threats of reporting me (to whom, I do not know)–without letting me get in a word edgewise. When he finally rested to gasp a breath, I attempted to explain myself when he screamed at me to “shut up and listen!”. I listened to him call me stupid for about another 2 minutes, and we parted ways…never to speak again. I will cherish our conversation forever.

  17. By David Suri on Jul 30, 2010 | Reply

    I was brand new to Telesales when I was making initial cold calls. The CRM system at the company I was working for had a lot of old names of CEO’s. As I started to make phone call after phone call and received numerous voicemails, I finally decided that I would ask the receptionist to put me on hold when I encountered a CEO that was currently on the phone instead of leaving a voicemail. On my last call of the day the receptionist said that the CEO I asked for was deceased. Without stopping, I said “I’ll wait.” She then followed with a long pause and said “I don’t think I can connect a line to hell.”
    Needless to say, my listening skills improved after that…

  18. By Casey Carlberg on Jul 30, 2010 | Reply

    So I was calling a restaurant today at bout 11:14 am, and i asked for the specific name of the lady i needed to get in touch with.
    I could tell right when she answered the phone seemed pretty busy and not too chatty. So i tried to just be real quick about things and I said Hi (so and so) and i just was giving you a quick follow up call and seeing how you guys were doing now with office supplies and maybe now is a good time at checking out some prices with other vendors.
    Her reply, ” Well this is a restaurant and its lunch time. You’re not too bright are you,” and then proceeded to hang up!

    Although is was pretty harsh, i managed to find it humorous.

  19. By Amber Dunphy on Jul 30, 2010 | Reply

    I recently called one of our contacts with whom we have not spoken with in quite some time and being as I am relatively new at the company, he had not spoken with me before. Also, being as I am new, I was fairly nervous. I had asked him if I could send him one of our new product binders, to which he enthusistically agreed.

    Then, he asked, “Can you send me a recording of your voice along with that binder”.

    I stammered, confused, and paused for a minute waiting for him to elaborate. He then says, “I find your voice intoxicating and if you sent me a recording of your voice I would get immense pleasure from listening to it all day and turning the recorder on and off”.

    What does ANYONE say in that type of situation? Not to mention this was one of my first sales call so I was already nervous and awkward as it was. Needless to say, I ended the conversation as politely and delicately as I could and have never spoken to him since.

    Co-workers in the office now joke and say I have a “stalker”.

  20. By Thomas Appleby on Jul 30, 2010 | Reply

    During a call with a prospective customer, I had just gotten them engaged and as I was describing our solution to their problem, when I felt a few drops of rain hit my face. Being in an office 20 floors up I was a bit confused and slowed down. As little droplets kept hitting me, I started to look around while continuing my technical description. That’s when I realized that my cubicle partner (a frequent prankster) had spilled water (I hope) on his desk and his notepad. He chose to dry it off by waving it at our short cubicle wall so that about half the water was coming over and hitting me in the face.

    Now I’m normally a very calm person, but this took the cake. Out of reflex I jumped out of my chair to take a swing at him, while continuing to talk to the customer. The smile on his face disappeared, but the cable for my headset caught on my chair and started to pull it from my head, so that my swing couldn’t quite reach him. After that initial moment of rag, and standing half bent over at an odd angle trying to keep the conversation going, I was forced to sit back down and try to finish the call. I don’t remember what happened with the customer, but my co-worker no longer works here. Yet, somehow I still get lot’s of e-mails to him from Brittney Spears’ fan-club.

  21. By Chris on Jul 30, 2010 | Reply

    Thankfully this did not happen to me but I was party to it. We’re in the recruiting business and we used to broadcast fax into medical facilities to find potential candidates. It was a smoking hot market at the time, and we got tons of call-ins from this. One call was from a candidate who already knew the rep who sent the fax. She informed him that a co-worker tried to call the number and reached a phone sex line. Yowzers. The rep’s wife (a graphic artist) had created the fax flier and mixed our toll free number with our local number. We sent hundreds of copies of that fax flier out. No telling how much money the company pulled in from people curious about the exact nature of THAT healthcare job.

  22. By Larry Dean on Jul 30, 2010 | Reply

    I was talking to a cudtomer we sell them all there binding combs and I was trying to up sell him to get the backs of there combs imprinted with there name and logo and he reminded me that they were a Brail binder and that was not going to be a big seller for them.

  23. By Kelly Smith on Jul 30, 2010 | Reply

    I recently had to call a customer to check on the status of an order. I had been emailing and calling him for weeks. I finally got a hold of him on his cell phone as he was on the job site.

    He proceeded to tell me that I was relentlus. He then went on to say “Kelly, you should come work for me. Quit your job in Ontario and come here! You can hound people for money, and if they don’t answer you, I will send you to their door to shake it out of them!”

    I couldn’t help but laugh. We got the order shortly after that. It really made my day!

  24. By Karla on Jul 30, 2010 | Reply

    I’ll start off with the fact that when I get a really bad salesperson on the hone, I always turn the conversation around and try selling to them - hilarious!

    I was with my office supply company for a few years when we decided that it would benefit us to have our administrative staff call to thank our active, self-maintenance customers. One particular call I made went something like this: Me - “Good Morning, this is Karla from ABC Supply and I would like to speak with Mary if she’s available?” Them - “No, she’s not available” Me - “When would be a better a better time to reach her?” Them - “When you die” OK, completely taken aback, I literally spluttered into the phone “Excuse ME!” Them - “She passed away last year” Really - they could have informed me in a more professional way, huh? So here’s me, totally riled up and not knowing how to react so I hung up! We didn’t hear from them for 5 years, when they got a new buyer who found one of our old catalogs.

  25. By Stephanie on Jul 30, 2010 | Reply

    I make about a hundred cold calls a day. I wrote down some stunning comments I have heard.
    About The Call:”Didn’t I hang up on you yesterday?”
    Reasons Mr. John X Can Not Come To The Phone: “He died seven years ago.” “I think they shot him and put him in a shallow grave. You are just moments too late.”
    When Children Answer: “My daddy can not come to the phone.(”how old are you?”)Four. How old are you?” (”sixty-six”)…click.
    My Industry: “I think the whole thing needs to be scrapped and revised.” “Isn’t it going to be obsolete?” “That sounds like the mafia.”
    Payment: “I am trying to get it for free.”

  26. By Mike Osterhaudt on Jul 30, 2010 | Reply

    When I first started in telesales, I called someone and instead of leaving my phone number on his voicemail, I left his phone number.. . .
    Then I laughed and said: “that’s your number, don’t call yourself, call me at XXX-XXX-XXXX”
    wouldn’t you know. He called me right back, Laughing all the way.

  27. By John McCarthy on Jul 30, 2010 | Reply

    As most of you, I’m sure, I to have had some funny moments but one does stick out.
    I was selling a software product whcih was fairly complicated and questions had arisen which were beyond my knowledge base so I asked a sales technician to come on the call and do a web presentation. I was the orioginator of the call so I was call leader for about 25 people total including my tech and myself. When we called into the webex we “appeared” to be the only people of the call so the tech and I enjoyed a little time to catch up since he was from a different city and we hadn’t spoken in a while. I am, if I say so my self, a pretty light hearted guy and I love a good joke so when I heard one I remembered. I put the call on hold using my phone mute button and proceeded to tell a string of hillarious jokes some even a little colorful. After 2 or three of these I heard uproarious laughter coming over the phone and, as you can guess, I had missed the mute button so I was on for all to hear. Being a bunch of developers and technicians, my prospects group knew all about the conference calls mute ability within the service and were listening to my “audition” untill they finally could not take it anymore so they took themselves out of mute and let us know. Embarrasing, but they really liked the jokes, I did get the business I was after there and they continued to use our services for upgrades and assitional software going forward.

  28. By Bob Willis on Jul 30, 2010 | Reply

    While working for a national chemical company as a tele-sales representative I had my best encounter to date.

    Our division was the B2B telephone only.Scripting, coaching and constant training made this company a National leader within the chemical industry. Stick to the scrip and you will be OK.

    I had just closed a sale with a female client and was going for the “add on”. The chemical I choose to present was an Enzyme based product that digests the source of an odor. The script was clearly written, “Each bottle contains Billions of organisms that will digest the source of the odor…”

    Well you guessed it. Feeling exuberant over the sale I had just made I began my add-on presentation. Not able to pull the script up fast enough I decided to wing it. I carefully thought about what was going to come out of my mouth NEXT while not paying attention to what was actually coming out. I proceeded to tell this woman “each bottle contains Billions of Orgasms…” Opps! I quickly corrected my mistake Organisms and just kept right on going pretending she did not hear and I did not say what I DID just say.

    She continued to laugh as I went for the close. Wondering aloud how she could possibly pass on a billion orgasms, she bought the add on.

    I never did follow up to ensure it was performing as promised. I suppose she is still at work enjoying her bottle and laughing at me.

  29. By Gary Berwald on Jul 30, 2010 | Reply

    I was calling on a potential client who had requested information from our 800 number. The man’s name was obviously Spanish and not one I was familiar with so I asked for him by his first name, Juan. The lady who answered just replied, “I’m sorry, no Juan home.”

  30. By Amy on Jul 30, 2010 | Reply

    I was on hold waiting for the decision maker when out of no where I got the hiccups. I was about to hang up when she picked up the phone. I started my introduction and hiccupped quite frequently, I apologized for the hiccups and told her I could call back. She was going to be leaving for a week and said she was ok since she wasn’t the one trying to sell with the hiccups. I continued into a full presentation of our service hiccupping about every 5 to 10 seconds. She said it was one the funniest sales call she ever had and, yes, I got the business!

  31. By Sabrina V. Pierre on Jul 30, 2010 | Reply

    I graduated with honors immediately post 9/11 with a degree in Financial Management-not good timing to say the least- so I took a job in sales cold calling for a national commercial collection firm. I was very entrenched in my financial jargon and trying to prove my industry and product knowledge to the CFO of a large company during a cold call…I intended to say “as Warren Buffet goes, so goes the market” - but it came out “as Jimmy Buffet goes, so goes the market”…he was silent—I laughed until I cried! To say the least, I didn’t get the sale but I definitely got a good laugh and a great story to talk about on future sales calls to people who actually have a sense of humor!

  32. By Debbi Bressler on Jul 30, 2010 | Reply

    The funniest sales call I’ve ever been involved with took place over ten years ago, but I’ve never forgotten it!

    I oversaw a group of inside sales professionals and had recently started working with a delightful, very religious, straightlaced gentleman named Jon.

    Jon had spoken to a prospect named Janelle earlier in the day and had set up a follow up call for us later that day, so I could answer some technical questions for her. Unfortunately, she didn’t answer the phone and instead we got this voice mail message:

    (With sultry music playing in the background) “Hi, you’ve reached Mistress Divine. I’m tied up with a client right now, but I’m really eager to take care of you when I return. If you just can’t wait, call Mistress Beatrice at xxx-xxxx and she can also service you. And, don’t worry, she’s just as wild as I am!”


    At which point Jon says, “er, Janelle, Miss Divine, this is Jon XXXXX, calling you back like I promised. I hope you didn’t forget that we had an appointment for a three way with my supervisor, Debbi.”


    “oh, oh, no, Janelle. I didn’t mean a three way like a three way. I meant the three of us were going to get on a call and get your questions answered. Oh my. Please, please just…oh gosh, please just don’t even call me back. Oh, my. And please erase this message.”

    At this point, I am literally on the floor with tears streaming down my face, with the phone on mute so my gales of laughter do not pick up on this woman’s voice mail. Poor guy couldn’t face me for over a week!


  33. By Greg Bradshaw on Jul 30, 2010 | Reply

    I used to try to catch people off guard by pretending to answer the phone in an obnoxious way. I always thought it was funny until one day… This is what I did. We would see the caller ID and many times knew who the customer was. When a customer that had maybe an annoying challenge about them I would joke with the other employees with an “I will fix this customer from bothering us again” and then pick up the phone and make some ridiculous comment that would offend anyone. Then I would hit the line and actually answer the phone and say in a smooth calm voice “Good morning Mr. Smith, how can I help you today.” It was hilarious to watch the faces of the staff think I had lost my mind and then even funnier to watch them figure out what I really did.
    One day an employee changed the settings on my phone so it answered upon picking up the reciever instead of hitting the line of the caller. They caught me as I answered the phone and told Mr. Smith he needed to stop bothering us with his annoying calls no one wants to deal with you… When he said “excuse me” I was mortified to hear his voice and quickly tried to explain. I got out of the situation with the customer and he laughed with me (or at me because I was not laughing). The office was out of control. Some were rolling on the floor laughing so hard. It was a very embarrassing moment for me and I never answered the phone that way again.

  34. By jane on Jul 30, 2010 | Reply

    I am currently a sales manager , selling building suppies to contractors. I started with the company when I was just 19 as a “rookie” telesales representative. This is one of the classic moments in my career that gets laughs from co-workers to this day. It may be considered R rated so I’ll warn the sensitive people ahead of time.

    I was calling on an existing customer in Kentucky ( we’re not in the South but sell across the country) , I was pretty familiar with the contractor but still developing the relationship. The customer was always very polite and normally a true southern gentleman so you will undertsand how taken aback I was , when in a very polite and Southern manner he answered and he said ( or should I say I heard) “You’ll have to excuse me for a moment Jane, I have a piece of ass in my mouth”. He put me on hold for a moment and I was dumbfounded and thought maybe I should call back at a more convenient time. When he got back I asked him to repeat himself and realized , with his Kentucky accent he was saying that he had “ICE” in his mouth…( Say it to yourself in a Southern accent– “Ice” “Ice”, you’ll see what I mean ) LOL. I’m glad I didn’t give him a “piece of my mind” for being crude :-)

  35. By Mike on Jul 30, 2010 | Reply

    I was with my sister when she recieved a phone call from a solicitor pitching cremation services. She burst into tears and shouted into the phone “who is this?” “How can you be so mean?” “My parents died last week in a house fire!” All she heard was (CLICK)

    She is so witty and is a telemarketers worst nightmare.

  36. By Bryan H on Jul 30, 2010 | Reply

    A rookie b2b sales guy goes big!

    A few years back I worked in telecom, a rookie candidate had been on the phones for weeks and could not set an appointment for the life of him. With much training and coaching he still could not get anyone to meet with him. It was my idea to attempt to measure his competence in a real life scenario so I built a calling list for him and replaced a company’s phone number with my cell number 7 or 8 rows down. I stood by awaiting for his anxious call but I chickened out at the last minute and gave the phone to one of my coworkers standing by to witness. Sure enough, my coworker put the new guy through a series of objections but showed signs of interest by eventually saying he was actually looking for a replacement provider and explained that the timing was perfect. The rookie proceeded to battle hard to other objections as the deal was qualified at a value of his entire YEAR of quota. At this point, I was ready for the call to end thinking it was getting out of hand and I had enough information to coach on. However, my coworker at the last minute agreed to a meeting the following week. I was instantly shocked thinking that this wasn’t the way the call was supposed to end. When the call completed I felt perplexed but the next thing I heard across the building was “BOOOO YAAAAAA B***CHES!!!!!”. The rookie loud and fast paced footsteps lead him to my office with a huge grin to tell me how he just landed this huge meeting and it was a hot hot prospect. Inside I was laughing so hard but I kept my composure and told him to keep the momentum up and continue to call. He kept calling, and he set 3 more meetings that day. The next week we fake a call back in to him and canceled the meeting saying that our contracts were still out another year. Although not what he wanted, we knew he had a net positive for the scenario.

    Moral: Physic yourself up to feel confident and successful before you make calls. People hear it in your voice and are attracted to it!

  37. By Dan Berkovitz on Jul 30, 2010 | Reply

    The customer’s name was Jeffery. I love saying a customers name often and in the right places in the conversation. In addition to helping me remember the name and associate it with the product or their situation, customers tend to respond better when I use their name often; it has some type of a good connection quality to doing that.

    I’m talking to him, “Jeffery, you know which watch I really like, it’s the Rolex yellow-gold Day-Date. We can customize the dial with diamonds around the hour markers, and put some more diamonds around the dial. Most customer that are looking for something classy get the diamonds placed on the band too, Jefferey.”

    I kept on using his name as often as possible.

    He responded to the watch because I was making him compelled to learn more about it and about what specific type of watch the other customers liked. I proceeded to get his credit card information.

    Me: “And how do you spell the first and last name on the card?”

    Jeffery: “J-E-R-E-M-Y”

    I was literally stunned. My mind was racing back and forth. Did he just give me the right spelling? Is this his first name and was Jeremy his middle name? Did I hear him wrong? Why didn’t he correct me earlier? What should I do or say?

    Me: “Okay. Let me get this right. Have I been saying the wrong name all along?”

    Jeremy: (chuckling slightly) “I thought it was funny how you were trying to build rapport with me and you were getting my name wrong the whole time too. I thought it was funny.”

    In my mind, I’m thinking WTF. I get the rest of his information and get off the phone as fast as I can. I learned to pay more attention to peoples names when they say it.

    * The actual conversation is paraphrased and the guy mentioned the spelling for the last name too but I don’t remember what it was anymore..

    * * If you enjoyed this, vote for me, and check out my website my friends.

  38. By Dan on Jul 31, 2010 | Reply

    I started my telesales career selling internet packages for $10.97. As in those times (not sure if its very different today), we did our best to push the product on a customer as long as he had a computer. Our database couldnt have been worse! We got the remotest of villages to call and sell.

    One such day, I was talking to a man who said he wasnt sure if we had our service in our area. “An objection from a customer means he is interested in your product” - thats what we were taught. I told this rather old gentlaman that we have over 500 connections already installed in this neighbourhood and its from popular feedback that we’ve called him with the promotion. The old gent took offense to this and in a very gruff voice said that its only him and his sister that lives in the area and theres not another soul in atleast about 50 miles. I had to sheepishly apologise and say that Il call him back once I confirm. Jeez - That was a real embarassment and I havent forgotten that in the last 10 years.

  39. By Tim Crockett on Jul 31, 2010 | Reply

    Early in my career I was standing in the reception area of Fulbright & Jaworski, one of the world’s largest law firms when the receptionist took a call from a young woman who asked to please speak with Mr. Fulbright. The receptionist responded that he was deceased. The caller then provided strong evidence that she knew little or nothing about the prospective client she was calling (and likely life on planet earth) by saying, “oh, I’m so sorry to hear that. You must be very upset. When did he pass away?” The receptionist responded, “about 100 years ago.” Does anyone still call AT&T and ask to speak with Alexander Graham Bell?

  40. By Sambit Sengupta on Jul 31, 2010 | Reply

    This happened to me and i found the calller to be lacking in training. Being part of the marketing team of world’s largest semiconductor distributer and no.1 in India- we do get calls a lot. mostly from customers- but occasionally from competition or from weird people who want to either waste our time or want to know /compare prices of different electronic components. one fine day- a lady called franctically and asked for phone number of our Asia president’s hand phone number. though i had no acess to such high profile number- but i wanted to check her problem. She told that she had an appointment with our asia level president in HK day after and she was stuck in bangalore international airport. i asked her what time her next day meeting was- her answer- 3pm.I asked her what time was her flight was- she told me it was at 11 30 pm.I told her that no such flight exsists for Hk at that time and i told her what i thought that she is a fraud. she broke down and explained that she is marketing person in a data collection agency and wants this data.she started sobing and crying–i was laughing all the way. i told that such information is available in lots of social networking sites or directory servicesand asked her to try there.

  41. By Rob Sinclair on Jul 31, 2010 | Reply

    Hi Art,

    I recently started a new freelance project calling CEO´s for a Business Development Summit taking place in Africa,
    I was actually calling “on behalf of” an African Country Government . I have recently moved to France and happened
    to call a major French company.My research had come up blank for the CEO name but I decided to call the only name at the bottom of their web page and ask for the CEO name.
    When I called and in my best French accent asked to be put through to “Melanie Fontaine” - I was asked in a very dry superior voice “Monsieur wishes to speak to the street on which our office is based ?” I carried on regardless and got the name I needed and during that day I must have told 20 prospects the story, I have not laughed so much for a long time….

    Glad to share this with you,

    Kind Regards,


  42. By Patrick Hennessy on Aug 1, 2010 | Reply

    I rang a company and asked to speak with a certain gentleman. The lady on reception informed me that the person was on a call and asked if she could put me on hold.
    The on hold was a talk radio station and the woman speaking on air sounded to my ear almost exactly the same as the person who had answered the phone. The call went like this,

    Reception: Good morning XYZ company

    Me: Could i speak to Mr Smith please.

    Reception : He is on a call could i put you on hold?
    Me: Sure

    Radio/Reception: Do you smoke marijuana?

    I must admit I was taken aback and for a second and thought i was going to be offered some sort of special deal! Then the radio conversation continued and i realised what was going on!

  43. By Darrel Beehner on Aug 2, 2010 | Reply

    I began doing lead generation rather late in life. Prior to that I did stints as a logger, miner, sailor and journalist. That collective experience has left me with vast vocabulary that isn’t suitable for the dinner table, let alone any form of telemarketing. But I’m always upbeat on the phone and can usually establish a good rapport with the people I’m calling. So a couple weeks ago I call Frank to discuss network needs. After a short chat, Frank tells me the network is handled at their corporate HQ. I tell Frank thanks and meant to say “I’ll call those folks.” However, while I got the “f” the “k” and “s” correct, the remaining vowel and consonant came out wrong. (Yeah, I dropped the F-bomb.) I immediately realized my mistake and began apologizing profusely. Frank didn’t hear me. He was laughing so hard he began choking. That made me start laughing. After what seemed an eternity, Frank finally composed himself and said “Don’t worry about it. It’s appropriate.” Armed with that knowledge, I opted not to call those, um, folks.

  44. By Dustin on Aug 2, 2010 | Reply

    My first sales job was selling health insurance to members of AARP, Which gives me enough stories to last a life time. This one is my all time favorite. I was on the phone with a client one morning and the only way to describe it is to put the conversation in text.

    Client: Does my health insurnace cover emergency Rooms? or do I have to go to the doctor first?
    Dustin: Yes you can go to the emergency room with out any doctor visit first.
    Client: Ok because I cut my hand and thought I had to go to the Doctor

    Dustin: No next time you can just go to the emergency room.
    Client: Ok because it’s bleeding pretty good
    Dustin: WAIT!! you are bleeding now!!
    Client: Yes this just happened and I didn’t know if I could go to the emergency room.
    Dustin: YES!! hang up and go to the hospital. NOW!!!!

    From that moment on, I never again wondered why when you call your insurance company or Doctor they say if this is an emergency hang up and call 911.

  45. By Ed Woods on Aug 2, 2010 | Reply

    I was working for one of the telecom giants and had limited research tools to find out exactly what business clients were in. I returned a call to one client I had not spoken too yet. I thought they were in the film business. Not movies but film products.

    When I called bac, I could here noise in the backround. Then I heard someone barking commands that were a little un-professional I thought for a business. Then I heard a woman, screaming “yes” and other things. It was so bad I was blushing. I really didn’t hear what the client was saying because of this backround noise. After a bit, I just couldn’t hold back and I said “I hear alot of noise in the backround. Are you busy? Is now a bad time? He said no he was on-set and could talk to me. I said “on-set”? He replied “Yeah we make adult movies and videos”.

    I told him to give me a call when he was off set because the noise was very distracting. He did and I got the sale.

  46. By Karla Olvera on Aug 2, 2010 | Reply

    Years ago I was the “go to” person for all wireless service related things for our Major Account customers.

    One day I received a call from a very upset customer asking why a particular service wasn’t activated as requested. I assured him I would take care of it promptly, but he questioned how soon.

    I attempted to say “I will do it quickly”, but I said: “I WILL DO A QUICKIE”. Immediately I put the phone on mute so me and my co-worker behind me could laugh hard.

    After a long pause I got back on the line, and to my surprise customer was much nicer. :)

  47. By Mark McCarthy on Aug 2, 2010 | Reply

    I was at the time, a Supervisor in an Inbound call center that sold products to small business. David, ( a young high potential sale person) had a hard time (so unstructured was he) building rapport and trust with customers early on in a conversation before he launched into a barrage of cross selling.

    Working hard with him for an hour or so, I encouraged him to ask questions of the caller, so as to get to know them a bit, build some trust etc as he worked through the order entry system. I gave him examples of questions to ask like ” Tell me bit more about how you use this product” or “What prompted your call today?” or “How is business these days there?”

    When time came to take live calls, I was sitting with hime side by side and I could tell he was a little nervous. The call came in (it was an office manager who happened to be female). She called to reorder a product and David began placing the order in the system and and then came dead silence…….

    I nudged him and whispered “Ask her something!” He looked at me wide eyed, jaw slacked and clueless but then took a deep breath, leaned into the microphone and said ” May I ask what you are wearing?”

    “Excuse me!” the office manager screamed. David looked a me and froze. I grabbed the heeadset off his head and felt no other choice but to explain to the woman what just happened including the side by side training I was doing and the stress David must have felt and how sorry I was…

    She had no choice to believe me ( you just can’t make that up) and all ended up well. I finished the order for David and when I hung up, I think we both laughed uncontrollably for the rest of the day.

  48. By Joey Peterson on Aug 2, 2010 | Reply

    After work one evening, I asked my semi retired husband… “So, what did you do today?” “Nothing special” he replied. “Just some yard work and lunch with the guys”. “Well if that’s what you did you better get on the phone and call Discover Card.” “Why” he asked.
    “Because they called to let you know that a new set of golf clubs and bag had been purchased on your credit card this morning.” BUSTED!!!

  49. By liz kusper on Aug 2, 2010 | Reply

    years ago i was calling on a company in a small missouri town.

    When i asked for “john smith”, the receptionist hesitated and asked me to hold on as he will see.

    after a few minutes he came back on the line and said he was not there. I told him i would call again.

    this went on a 2 or 3 more times with no success of reaching my contact.

    finally, last time i called the man who always answered said “John only shops here once in a while! i transposed 2 numbers and got the store he shops at instead of the company he works at, so each time i called he would go looking for him in his store!!

  50. By Dale Spoon on Aug 3, 2010 | Reply

    My most embarrassing would have to be the time I called a buying customer who does spray tanning to tell her about the new firming spray for add on sales, instead of firming spray I said “sperming spray” in my message to her.

  51. By Allison Savage on Aug 3, 2010 | Reply

    I called a customer to let her know lamps were on sale. I asked her how close she was to re-lamping. She said she wasn’t sure – she would have to look at a map!

    How do come back from that one?

  52. By Lynn Lamb on Aug 3, 2010 | Reply

    After having just completed a call with my boyfriend, I immediately got a call from a regular customer, and as I was closing the call I said ok bye, love you.

  53. By Harrison on Aug 3, 2010 | Reply

    I once had an inquiry from a person with the last name of “Fuque”. I called him and asked to speak to Mr. Foo qway. He corrected me and said, “the name is pronounced F*&K. So, I referred to him the way he wanted to me to refer to him. Try doing that with a seriousness of tone!

  54. By Dan Seidman on Aug 4, 2010 | Reply

    While on a sales call at a large NY-based insurance company, the prospect became very defensive. We were pitching a 12 million-dollar outsourcing program and Tony, the buyer, couldn’t seem to pull the trigger and decide whether he would let us work with his company.

    My selling partner and I asked to use a phone to call our headquarters for some direction.

    The administrator let us into the unoccupied, expensively-equipped videoconference room and led us to a speakerphone. While on the call with HQ, our sales manager got heated and his language became less than professional and quite loud.

    He finished by blasting out something to the effect of “Screw Tony, he doesn’t have a clue.”

    So we ended the call with our new marching orders. As we hung up the phone, a pleasant voice came over the loudspeaker in the room letting us know that the entire call had been broadcast over the intercom system within the building.

    Time froze.

    We were numb.

    As we zombied down the hall, Tony turned the corner. He wasn’t aware of the broadcast as he was in a meeting during the call. We exchanged pleasantries and got out of the building as soon as we could. Needless to say, we didn’t get the deal. Tony heard what happened as soon as we left.

    Would it be a surprise that he’s never returned another call?

  55. By Allen Jingst on Aug 4, 2010 | Reply

    At a previous employer we had a new sales rep start. He was just out of training and was pounding out calls to the “crap list”. Another co-worker called me in to her office to listen to a voicemail she recieved.

    Over lunch she recieved a call from our new sales rep on her dummy account set up in our CRM system. He proceded to leave her a 2 minute message droning on about our services. He did not notice on the account in our CRM system that she worked for our company, and even after her voicemail identified her name and the company name he still proceded to leave his message.

    I can understand not knowng her name but it was clear he didn’t care much. Needless to say he did not last long.

  56. By TJ on Aug 4, 2010 | Reply

    The experience I had happen recently was between PG13 and R rated. I was speaking the new Dir of IT and she was telling me how new she was and how she wasn’t sure about projects being on the table. I said something like “oh your probably still getting your feet wet with your new role”. Her response, “No I am pretty wet actually right now”. Because of the immature side of me, I started laughing and had to hit mute. The funny part was she realized what she had said I started laughing as well. the call turned into a good conversation which we both laughed off in the end.

  57. By Ben Fuehrer on Aug 5, 2010 | Reply

    Our company recently relocated to a brand new office building which includes a new phone system. A few days ago, the customer service manager approached me and said, “Be careful when you are dialing out. Someone has called 911 and the cops have been out here on 3 different occasions to check on everything. They are not very happy to say the least.”

    Thinking nothing of it, I received an email earlier this week informing me that I had been the one who had been dialing 911!

  58. By Mike McMahon on Aug 6, 2010 | Reply

    Many years ago I was working on the phones selling software to consumers. The company had built in a slot machine to the dialer so that each time you made a sale you got to spin.

    A friend in the cube next to me got a sale and spun with several of us watching. First a cherry came up and then another cherry popped up so I started chanting “cherry, cherry, cherry…” but a bell came up instead and I said “Ohhh crap!” only to hear in my headset “Excuse me?!” I was so shocked that I had gotten a call and they had just heard what they heard that I disconnected and logged off for a quick break. Talk about embarassing. ;-)

  59. By Charles Elliott on Aug 7, 2010 | Reply

    I get a hold of a Purchasing Manager for ABC company during my call outs. After my opening who and why sentence he asks me to hold on a minute.

    Waiting patiently to hear his voice so I can continue, I hear the noise as if an office chair is leaning back slowly. Then an “mmm… that’s nice” with excitement behind it from his end distantly.

    He comes back on the phone and crudely says “Sorry about that, a nice pair of breasts and legs just walked down my isle.” Being flabergasted and embarrased, I laughed nervously and said “Nice, do you have any openings for me?”

    I meant at his company, but being where his mind was he took it another way and hung up on me after “What?”

  60. By Jessica Roberts on Aug 8, 2010 | Reply

    While making phone calls from the East Coast to the West Coast, a patient answered the phone by simply saying, “can’t talk, True Blood is on” and slammed the phone down. Now this was not a matter of them thinking I was a telemarketer as on their caller ID we show up as their physician’s office! I was so stunned with that hang up and laughing it took a few minutes to compose myself to keep going!

  61. By vihang on Aug 10, 2010 | Reply

    i started my sales career working as a sales executive for a credit card company . now i happened to call this guy in texas for a credit card . i started my sales pitch , he interrrupted stating that he was not interested in any charge cards , i tried convincing him by knowing more about his lifestyle .

    then he said that he was on bike and i asked him which bike does he drive . he replied ” i am driving a harely davidson ” , i said great thats my favorite bike , he had a great connection with me and the conversation continued until 15 min . he gave me some advice on bike usage and i asked him a few questions on how he enjoys his drive on his harley .

    the man liked me so much that he immediately asked me to send whatever i was selling without even bothering to listen further to my pitch . my manager who listened to the call was not impressed by sales skills called me up in his room for a session .

    but in my opinion this was the most easiest and wonderful sales or my career , this a a real realtionship sale based on trust .

  62. By edihok on Jul 14, 2011 | Reply

    I’ll start off with the fact that when I get a really bad salesperson on the hone, I always turn the conversation around and try selling to them - hilarious!

  63. By Kellbwm on Sep 23, 2011 | Reply

    Several years ago when my husband and I were first married a magazine company started sending us several different magazines in the mail. I never kept them, just sent the back as they came in. Then they started calling my husband and wanted us to pay for them. We repeatedly explained we did not order the magazines and had sent them back and we were not paying for them. The magazines always came in my husband’s name and I always knew when they were called because they would mangle his name. So one night I had enough of arguing with them. While my husband was sitting on the couch listening I told the salesperson that he was gone. I went on a rant about kicking him out, he no longer lived with me, I didn’t know where he was and I didn’t care. I was yelling at the top of my lungs and slammed the phone down. They never called again and the magazines finally quit coming in the mail. We still laugh about it to this day.

  64. By May on Sep 3, 2012 | Reply

    I had taken a few naughty pictures of myself wearing only heels, stay-up stockings make-up and a smile, and instead of sending them to just my husband, I accidentally sent them to all of my contacts, family, friends, co-workers! I was mortified and avoided everyone for quite some time.

  1. 3 Trackback(s)

  2. Jul 31, 2010: What is Your Funniest or Most Embarrassing Phone Experience? Win a $300 Headset! : Telephone Sales : Selling & Marketing Tips To Increase Sales
  3. Aug 9, 2011: You Can Fool Your Attitude Into Being Positive and Confident | Art Sobczak's Telesales Blog
  4. Aug 11, 2011: You Can Fool Your Attitude Into Being Positive and Confident : Telephone Sales : Selling & Marketing Tips To Increase Sales

You must be logged in to post a comment.