Want to learn how to easily get your first 5,000 subscribers? Download this free eBook to learn how.

"Help! I Have No Conversation Skills - And I'm Awkward When Talking To People"

Back when I was starting college, before moving to school, I spoke to my would-be roommate on the phone…

…And that conversation went so badly that my would-be roommate figured out a way to transfer into a different dorm room.


Fast forward to now, I’m GREAT at starting and holding a conversation.

And I’m not just patting myself on the back. Five minutes with me in any situation and you’ll see that this nerdy, introverted, book reader can break the ice with anyone, keep their attention, and walk away with a new friend or business contact.

What changed?

I’ll explain.

Awkward Conversations 101

What’s the SCARIEST part about an “Awkward Conversation?”

If you’re the awkward one, you’re flushing your chances of success down the toilet. You can kiss things like “making lasting friendships,” “forming valuable business partnerships,” and “persuading prospects to buy” goodbye.

And you won’t even know it happened.


Awkward people are oblivious. Everyone knows it but them.

Now you might think, “I don’t have to worry about this… I’m not awkward…”

But there’s is a spectrum of awkwardness.

On one end, you’re the guy that everyone shuns. The guy people can’t help but laugh about.

And on the other end, you’re the guy everyone wants to talk to, work with, and help. The guy that seemingly has everything drop in his lap.

You likely fall somewhere in the middle, right?

Sometimes you bomb a conversation. Other times you ACE it.

I know the feeling…

…But as I said, a lot has changed for me over the past 10 years.

And it wasn’t an accident…

(Want to be the FIRST to learn more? Hop on this “Early Bird List,” and you’ll be the FIRST to get more information about how to be the most interesting person in the room… even if you’re introverted… even if you think you’re boring…)

For now, I’d like to do something fun…

I’d love for you to join me (and other Social Triggers community members), and share two separate stories in the blog comments.

For the first story, I want you to tell us about a time when you bombed a conversation. What happened?

(Dig deep. If you haven’t bombed one recently, think about that one time you did, and share it. Kind of like I did with my college roommate story).

For the second story, I want you to tell us about a time when you ACED a conversation. What happened? How did it affect your business and life?

Leave a comment below.

Spread the love!

Join OVER 200,000 subscribers


Click here to sign up

Need more? Choose your path below

68 comments Leave a comment

I just feel throughout my life I have always been the reactor in a conversation and never the person that starts conversations and can actively approach and talk to people. I always let people talk to me and that never seems to happen to much. Just want to be able to be more social and not anxious about talking to people. Although I have had many good conversations, those past awkward conversations always come to the forefront and I never can give myself credit.


One time I was talking to a girl who I had confessed feelings to a day before and I asked her a question where I tried to be casual/playful and she gave a simple reply and I pressed and thought she had more to let on, but in my mind I felt shame because I didn’t feel like I was being nice, so I ended up just holding an “um” and telling her I can’t talk and that made things more awkward between us for a period of time.
One time I had a good conversation was with my best friend and we were hanging out and had a conversation about a hypothetical situation and what one should do, and I think a lot of the convoersations good qualities came from my comfortability around him since he was my best friend.


For bombing a conversation, this one actually happened recently at my new workplace. I was upstairs in the breakroom and one of my coworkers came upstairs to go on break, too. He asked me where I went to school and I replied, but the whole conversation felt very one-sided and I kept glancing back at my phone because although I didn’t want to seem antisocial, I could sense the conversation was going terribly and I just wanted it to end, even though I enjoyed talking to him at the same time.

As for acing a conversation, I’m not sure this counts because this was a conversation with a longtime, very close friend of mine. Nonetheless, a very close friend of mine and I went for coffee after not having seen each other in a long time and the conversation just hit the ground running and before we knew it, we had spent over two hours at our local Starbucks just chatting and catching up. I’m very awkward in conversations, but I felt very at ease and relaxed having that conversation. I just wish all my conversations went like that…


My husband and I started going out to dinner with his boss and his wife, nothing literally to talk about very awkward. I ask a question and she goes on and on boring. Oh and she doesn’t and me any. Husband likes to talk about work boring. What to do? In real life I would never hang out with them they are just to into themselves but they are very kind weird.


So ever since I decided to commute to school for my sophmore year, my social life has crumbled. I find myself constantly sitting in my room, not knowing what to do because my old friends are away at school. I dont know anyone really at school and am never there long enough to creat friendships because of the commute and work. This constannt struggle of being at home caused me to loose my conversation skills, to the point where I don’t even know how to talk to my family. Today, I went out with my best friend and he introduced me to some of his friends and I didnt know how to hande it. My main issue is that I havnt had a relationship since junior year in highschool, and im going to be a junior in college soon.. some please help me figure this out.


    Conversation is not just words.. maybe go back a step.

    Eye contact and smile works very well between men and women. Don’t run away when she locks eyes on you, but don’t look hurt that the eye contact ended. Go back to looking at her – if you are not having a conversation with a women with her eyes before you meet, then you’ve wasted one of the best parts of life. Check her out when her friends are watching her and she’s not looking so her friends tell her she was just checked out. Be relaxed about it. Don’t fear women they can’t hurt you. Keep good hygiene, hair cut and wear newer clothes. Be ambitious with intention to earn money and do something interesting in your life that she will find interesting. Make an effort to be humorous even if you fail a bunch of times. If she doesn’t laugh at your jokes maybe you are not right for each other. If you are going to date, try to find a women who wants the same things as you and can accept each others faults. Otherwise you will argue too much.

    Don’t judge your historical love life with your current one. You can go for one spell to another.


    The way to quit smoking is to be honest about why you smoke, and then desire and be a non-smoker. That sounds really obvious to many but when you have a serious addiction, part of your brain’s concious is overwhelmed by a voice that creates doubt. Attacking that part of your brain, or making up your mind, you can do anything.

    I believe inhibitions and anxiety in social situations stem from the same part of the brain that reinforces addictions. It’s that voice of doubt that resists change. Therefore, convince yourself of your own desire to be someone who is social. Shut down the part of the brain that creates doubt and has historically taken control of you in these situations.

    Being decisive when it makes sense to be decisive is a good quality and keeps the brain functioning normally.


    Real name is neil, dont know why i used a fake name ted hah.

Michael Douglas

In the last two days, I went to out some parties and I was the awkward guy there. I couldn’t make or start a decent conversation with anyone and I got frustrated with myself. I want to try talking about things I don’t normally talk about and I want to make people feel good while having a conversation with me and not uncomfortable. And also I had some interviews that didn’t go well because I sold myself short and basically had trouble talking to him in a way that would make him wish to hire me. I need help.


A time when I bombed a conversation? Too many to count. I’m in college so basically my entire social life is riding on my conversation skills. I was on a date with a guy I was interested and I literally just could not think of a thing to say. And it’s not just with guys. It happens all too much, even with my best friend who is honestly way cooler than me. I’m so terrified of judgment that I can never think of a thing to say that wont sound dumb.

A time when I aced a conversation? I really can’t remember. I am endlessly awkward. I try to pull it off in a quiet/mysterious/too cool to partake in your dumb conversations way, but at heart I really want to meet people and get to know them. The only time I ever really open up is if I’ve had a few drinks

Anyways, next year I’m transferring to a school where apparently everybody is perfect and I’m only average. I want to rush a sorority and be a part of student government but I really think it’s important to learn the art of conversation first.


I’ve found the easiest way to make a conversation less awkward is to move the topic of the conversation to the other person. It makes them feel important and people always like to talk about themselves.


    I followed this advice for years. But it’s left me as being someone who is talked too. I feel unable to talk for more than a few seconds before diverting the attention back to the other person.

    But I don’t want that, I want a two way conversation where both parties are aware. Where both people contribute to the conversation. This requires awareness from both people to ask questions of the other person and their views which I’m good as. But 99% of people seem bad at. They’ll often talk for 10 minutes straight. I could have an opinion on something but there are no natural breaks that allow me to offer my opinion.

    So this tactic I feel just hides the issue. Yes diverting the attention makes it easier but it doesn’t solve the real issue.

Taylor Crow

I think the awkwardness in conversations some times and ‘acing’ as you say other conversations is just the ebb and flow of life. And the people that everyone laughs at are just constricted inside and afraid to experience people or life in a real way. Know what I’m sayin guys?


BOMB: awkward conversations? Me? Yeah I get those all the time. I feel like I been having a maturity gap between a lot of people ever since I left high school. Of course I’m trying to improve my life, but sometimes, during a conversation… I JUST CAN’T RELATE! Or I feel like I don’t trust myself enough to say the next words coming out my mouth. This probably happened many times over the past few months. The words that do come out of my mouth sometime, well shit… hasn’t made me a lot of close friends in the past year that’s for sure. Two cases that I felt were awful:

1. During rush week of trying to join a fraternity, I remember bragging to the brothers how badly I wanted to join their fraternity, and all the stuff I felt that involved. Basically giving deep thoughts to people that I felt were like “Yeah whatever dude.” Conversations were dull and bland. Well maybe not completely dull but they weren’t amazing conversations. Well I’ll give you this… The interview worked out the same. I knew I was definitely trying too hard and I ended up being the VERY few not making it into the fraternity.

2. Another case. I remember my friend saying “Yeah my teacher looks like my sister.”

I answered: “So is she hot?”

Who the fuck says that? It only took me 10 minutes later until I realized I said something pretty damn awkward…

ACED: This one girl. You know… I’m just being wild… being “myself,” or at least what I felt was really myself. I’m just talking to a girl about her life back at home you know. Then we go into a conversation about her ex’s, her life, her sports, interests. She definitely showed me friendly affection! It was good while it lasted…

Veronica James

the Bomb!
i was recently in a conversation with three other people. Two of those people was a man and women i had just started working with and it would have been more than helpful to have impressed them with my ‘witty banter’, (the man had also recently shown a very obvious interest in me and loved to flirt with me while texting) however, as is usually the case i was dreadful! i paid attention to the conversation but couldn’t find an ‘in’ to the conversation and even if i could i didn’t have anything to say nor could i think of anything. i can text and carry conversations in the texts to the man but once face to face i have nothing to say. it is beyond awkward when he notices that i can’t hold a conversation with anyone and then when i do i tend to stutter and slur my words. I am a 24 year old women, i don’t drink and i am socially awkward with no close friends. i like this guy and he seems to like me (i don’t know why, i’m chubby and he is good looking!) i blush furiously when i realise how awkward and uncomfortable i am.. so it’s like a flag just in case nobody noticed already. i need help but i don’t know what to say or how to slip away when i realise that i have no idea how to join a conversation that people are having and they obviously expect me to contribute. What do i do? please help!

Maggie Patterson

Bomb – Getting in trouble with my smart mouth. Moving up quickly in a tech PR firm when you look younger than you are and are 5″2 makes for a lot of commentary from male CEOs. More than once I had my mouth engage before I could stop myself purely because while despite my awesome work and results, my age and height are up for discussion? Let’s just say my remarks didn’t always impress my higher ups, lol.

Unless…you end up getting lots of extra business out of a CEO after giving him the “what for” because I was actually older than he was and he liked that I wasn’t taking his crap.

David Hamilton

As someone who helps people with social anxiety and awkwardness, to be more socially confident, I too have been through the ringer on this one.


So many to pick from the past, but one would be in college with this girl I was seeing, it was actually her friend. I was just rude to him when he introduced himself to me, because he was athletic and I was the skinny musician kid. Trying to hold power over him by being rude to a genuinely nice guy.


Luckily there are many to pick from these days, as I network everywhere I go, but one would be with a guy who runs a networking group in Denver, I actually shared very openly about a story of struggle. That opened him up to do the same, and we are now speaking at an event together.

Great topic Derek, thanks for this man. Hits right at home with me and the people I work with, I’m going to repost this to my Facebook community on social anxiety.

Felicity Fields

I recently failed a sales conversation with a client. Realistically, I know I could tackle a different web platform (since it was similar to the one I use), but in reality, I asked too many questions & the client went with a designer who had more experience.

On the other hand, I had a wonderful conversation with a different potential client on the phone today. She was leery of tackling her Facebook page, so I asked her point blank what her issues were, we explored them, and then she said yes to working together.


FAIL: I was at a Christian fun & games night. We had ad-lib teamwork, comedy basically. I was too serious & didn’t know how to lighten up the mood or be funny. I was still learning how to come out of my shell to talk to people, let alone speak up for myself. I was not ready for “entertainer” mode. Crickets sounded as my team looked at me in tense, awkward silence….

SUCCESS: I aced an interview and turned every negative question into a rose bearing thorn bush. They were floored & speechless.


My awkward moments were when I was first learning how to
call leads on the phone. Their were many uummmm (because I was
trying to remember my script)..many pauses (because I forgot what
to say next) Now though I am very smooth and am actually listening
to my prospect excuses.

Dwight Schrute

I am the BOMB king.


Funny, we seem to remember the conversations that were awkward :-). For me it was recently at a holistic wellness workshop. There was a MAJOR name hosting the workshop (a celebrity), whose work I greatly admire, and who inspired me to be on the journey that I am today. On the finally day, after small talk here and there, I summoned up the courage to ask him to do a skype interview with me in the future, once my website is up and running. I was TERRIFIED, but I knew I had to do it… otherwise I might never again get this moment. Needless to say, I started talking about my new wellness business and how he inspired me and spreading the message to the world. I heard myself rambling, and then some weak request for an interview.. OH GOD! Funny thing was that through all my nervousness… he said YES! I couldn’t believe it. My hands were shaking so much that I could hardly write down his email. I know that he saw, but of course was gracious enough to ignore. I was so horrified that I wanted to curl up into a ball. But I guess the silver lining…. At least he said yes πŸ™‚


I am so guilty of being awkward. I just don’t have enough practice speaking about what I do; although, I have gotten better.

5 years ago, while my friend and I were on treadmills at the gym, this guy comes up and gets on the one next to my friend and starts asking her what she does to strike up a conversation. We were both married at the time and totally not interested in the small talk, plus, we were exercising. None the less, the guy proceeds to ask me what I do, and I say, “Oh, I make jewelry.” Then, he asks the most common follow up question I get, “What type?” I responded “uh, just sterling silver stuff,” mostly because I lacked confidence in what I did. My friend corrected me and said, “no, she makes gorgeous fine jewelry in gold and silver.” But my response was enough to make the guy not interested. Considering the location and guests of the gym, he could have very well become a customer of mine had I spoken highly of my own work.

Too often, I am accusatory of the intentions of small-talk, instead of being willing to accept an opportunity to network.

Recently, another fail: I was doing a show and had been featured in the local paper prior to the event. I had been able to write down what I do and submit it to the paper. I feel I’m a strong writer, so my words flow to my fingers before they go to my mouth. A lady came in with her husband, so excited about how I write inspirational poems for each piece of jewelry I hand make. She asked for me to explain to her husband what I do. Simple enough question. I fumbled and stuttered and fell all over my words. He was not impressed. They left without a sale. The quality of my work right in front of them couldn’t salvage my inability to talk about it.

As much as I write about what I do, I thought I would be able to talk about it pretty easily, but they are such different tasks for me. I’m working on becoming a stronger speaker by making videos, and talking to people when I get the chance (work from a home studio).

An ace conversation, occurred last month when I was speaking with the owner of a workshop that offers courses. I was making a proposal to teach the 4 C’s of Diamond Grading (cut, color, clarity and carat weight). It’s a topic I studied professionally over 15 years ago and have been working with ever since; I can talk about it in my sleep. I immediately knew my target audience for the class and we were able to exchange great planning ideas.

The obvious difference is my confidence level in the topics being discussed.

I was actually thinking my fail stories yesterday as I prepped what I would say in my video to win the Social Triggers workshop tickets. How apropos. This made me realize I’m not *always* awkward and what I need to work on.
Thanks, Derek!

Alexis Meads

Love hearing everyone’s stories! 1. I was doing a
presentation recently in front of a high school biz class (90% 17
year old boys) and was talking to them about my business. Part of
my business is based on natural health and I gave them a quiz to
see where there health status is at. One of the questions asked
about their…ahem… bowel movements, I totally forgot to delete
it out of the quiz and the whole class burst out laughing! I didn’t
know how to play that one off and got so embarrassed. 2. Recently,
I had a client going through my Custom Cleanse Program. When I
truly listened to her pains and needs, and responded with
confidence and clarity, I found that it really helps people to feel
supported and heard. She successfully completed my program and was
grateful for my support!

Niight Wind

My two stories are based on having the same conversation but with two different groups. The first was at a crafting party that involved plants and I started talking about how some of them were edible. I didn’t realize the people there were really just there for the wine and the craft was just an excuse. I later heard that they thought I was too passionate about plants and have not been invited back to a “crafting party”. I then had a similar conversation months later with some gardeners at an Ignite after party and they totally loved it and the conversation went on for almost an hour. Guess you have to know your audience:)


This was an interesting article to read because I expected to go into how awkward conversations are good. Because… that’s what I’ve seen in my own life. I’ve had a lot of awkward conversations in my life… but I usually just write them off as me and that person just not clicking. But even a lot of the people that I felt my first conversation with were awkward ended up becoming some of my best friends. I think putting yourself into conversations that could potentially be awkward ends up building a lot more friendships than thinking awkward conversations are bad and should be avoided.


Awkward > Meeting a prospect at their office (referal from a friend), learning they were excited to meet me (and, mind you, I sent an email thanking him ahead of time and confirming what I do) only to find out he wasn’t looking for copywriting but someone local to take over his hosting. Okey dokey, quick damage control, offer to make a connection, and segue into copywriting. This one probably a no go anyway; his desk was kinda on this “stage” and he had a built in table on the guest side that was about 10″ lower than his desktop. That was awkward too:/

Score: On 3.5 hour flight from Philly to Dallas/FW 11 days ago, my seat was unexpectedly separated from my daughter. Her seat companion was a young man her age with a great smile – so be it! I sat down next to this guy who was such a gentleman (he offered to switch seats with my daughter though 10 rows ahead), and we ended up chatting the entire time, finding crazy cool “ain’t it a small world” parallels, and discovering he needed my services for a big, upcoming project. We chatted yesterday and the NDA should arrive in a couple of days. What are the chances? Love it when stars line up:)

Thanks for a great topic, Derek. Have an awesome day!

Missy Cooke

Once I interviewed a daycare for my daughters and didn’t
end up using them. A couple of months later I saw the owner at the
park and her friend started to introduce her to me. I responded
with “We’ve met before. I interviewed at your daycare… obviously
I didn’t choose you.” Ahh! What was I thinking?? I can’t think of a
specific example of rocking a conversation, but I do remember that
usually this happens when I’m relaxed and don’t have an agenda…
meaning, I’m in the conversation just for the sake of good company.
If I can drop any pre-conceived ideas about what I “should say” or
“should do” and just treat the other person like a person, things
always seems to flow naturally.


I’m a noob and am working with a mentor while learning
copwriting. I recently had the idea of targeting resorts (which I’m
not pursuing). I wanted to do research first to see if resorts
would be a viable market. My idea was to call resorts and see if
they would answer my survey questions, which I would e-mail to
them. I called the GM of a hot springs resort and had my own (noob,
remember!) phone script written out. After making my initial pitch,
I closed by mentioning the ultimate purpose of the survey. Me:
“Basically, I want to be able to enter the conversation in your
mind so I can give you exactly what you want.” Her: “I would feel
very, very uncomfortable moving forward with something like this.”
After our conversation, I realized how absolutely creepy “I want to
be able to enter the conversation in your mind” sounded!!! I
couldn’t blame her for being a bit afraid! I was using language
that only an entrepreneur would use…while not realizing that you
do not necessarily use that language when trying to drum up
business….it was a huge fail, and a lesson very well


When I first decided to change careers from teaching to marketing, I went back to B-school for an MBA. I remember the first day of orientation, there was a lot of chest-thumping going and namedropping going on. Being a teacher, I spent most of days talking to kids and went in to a bit of shell shock when it cam to icebreaking with my age peer group. Rather than following suit with everyone else, I decided to try and make a more personal connection with my cohorts (i.e. – likes, hobbies, etc. as opposed to accomplishments, GMAT scores, and such). Major bomb! I think I must have come across as a dork; I would join a table and find myself alone within minutes…OUCH. I wound up spending the rest of orientation sitting at the table of students who barely spoke English [side note: I made an awesome friend here, I guy who was brilliant with Math and really helped me get through some of my tougher courses]

Same semester, it came time to do final presentations. My group was dying on stage. I through out the flash cards and told myself to do my best to keep it simple and entertaining. I was surprised when i heard the first bursts of laughter at one of my jokes. I killed it! My group got an A and the whole class commented on how amazing I was. (I guess my experience as a teacher paid off here). After that, a lot of people requested me to be a part of their groups whenever a presentation was due. Go figure, eh?


    haha, just noticed all of my typos. That’s what i get for rushing while at work. LOL.

Jeff Gibbard

Simply put, I bomb the conversations where I talk too much. I tend to ace the ones where I listen more.

Go figure.

Jessica Oman

Um, I am fully aware of my awkwardness…it usually goes away after one drink. And comes back in full force after two πŸ™‚

I bomb conversations at networking events when I don’t hear what the other person says and I can’t figure out how to ask them to repeat themselves. Oh, there was this one time my half brother (who I’d only met once and not seen for several years) thought it would be funny to pretend to hit on me at a bar because he knew I didn’t recognize him…yeah THAT was awkward.

I don’t have an ace. I wish I did.

Aimee's Simple Living for Busy People

I have always considered myself able to contribute in a kind and heartfelt way into any conversation. But there are definitely awkward ones.

…..but the awkward convo that *instantly* comes to mind regarding my awkwardness has to do with dating/love (of course) When I was headed into my freshman year, I spent the remaining portion of my summer vacation to learn how to windsurf. Every day, I fell more and more head over heels with my windsurfing instructor (he was a senior). Indian summer hit, and I wanted to say something profound to really get him to like me, and all I could eek out was “Jamie, you are such a good windsurfer.”



I felt like Baby in Dirty Dancing when she responds to Johnny’s “what is she doing here” question after meeting him for the first time and respons with the clever: “I carried a watermelon”

For me, I find that my “awkward conversations” occur when I try to hard, and then I am not myself. In fact, it is when I “put an extra effort” into things at all. Not like, I should sit like a bump on a log, but when my speech comes from a place natural confidence and self assured heart centered speech it is never awkward.

    Aimee's Simple Living for Busy People

    …….For my Great Convo: When I fearlessly called back a client who had written me an emotionally charged email about something that had occurred with an event I was involved in planning for her. I listened, didn’t have an agenda, spoke from my heart, suggested some ideas to resolve the situation…..and completely turned the client around and the event was amazing. Total satisfaction for both of us and her guests! She’s now a glowing testimonial for me and my biz, when it was seriously looking like it was about to be the worst experience ever.


Bombed: Had a talk with a man in the sauna which turned really awkward. I was actually wondering if he tried on purpose to annoy me. Well, I can get like a cutting knife in such moments and I guess it is nicely put. Long story short, I realized that he didn’t wanted to annoy me but to impress me. Yet, a man who tries to impress me bores me to death.

Empowering: Had another talk with a man in the sauna who had such a strong energy that he made me feel alert. I chose the simple way, I told him so. He wanted to know if I am afraid of him and said that people often tell him that. I told him that I wasn’t afraid, but that I became alert. That his energy is very strong and raw and wild, unusually so for our culture (Switzerland). That he is like an uncut diamond. And that there is nothing wrong with or violent with an uncut diamond, he simply isn’t yet shining in a refined way. He very visible relaxed and breathed more deeply.


Awkward: I have to share this one even though it was a long time ago b/c it still sticks in my mind as a reminder to think before you speak:
I was in jr. high and there was a really, really nice girl who always sat next to me and she was very overweight. I felt sorry for her b/c she was such a good soul but people would ignore her b/c she was heavy.
One day, she came in and gave me a stuffed animal as a present and she said she wanted to give it to me b/c I was always nice to her and helped her a lot. I really was touched and I said to her, “thank you so much. I can’t believe you gave me a present! You are such a sweet rolly polly…..”
AWKWARD. As soon as it came out of my mouth I tried to recover and she turned red and I continued to gush my gratitude but damage done.

I recently went into a sales call with a new physician whom I had never met and as we sat down to talk it started out a little awkward. I could tell she wasn’t in the mood to really listen to a rep. BUT I kept looking for things we had in common and mentioning things in my own life that would be triggers for her life and she realized we had a lot in common. Next thing you know we are talking about kids, life, travel, family, etc but I would slip in information about my products at the same time. She set up a meeting with the entire chain of practices to start purchasing my products. I actually ended up genuinely liking her too and I look forward to working with her again.
I love it when that happens.

Janae Moss

Bomb: (Nice Man): “It’s nice to finally meet you Mrs. Moss.
How long have you owned your building maintenance company?”
(awkward me): “About ten years now. It’s been a crazy journey, but
worth every day!” (Nice Man): “That’s great. Well, I was wondering
how you run all of the accounting and payroll in your business, and
if we could be of any service to you?” ( awkward me): “Oh, well we
used to have it all in-house, but now it’s all out-house…” Great
Convo: (Nice Man): “Hi there! I just wanted to congratulate you on
being nominated and selected as ‘Utah Business Magazine, 30 women
to watch’ this month! How does it feel? (confident me): “It feels
great! I always knew that all of the crazy things I have been
through, would pay off in the end. I am a completely different
person because of my experiences, and I’m ready to share that with
people.” (Nice Man): “Good, because I wanted to ask you to speak to
a few groups of people, and share what you have learned. Would you
be willing to do that?”


My last really stand-out awkward conversation happened when
I unwisely allowed a Mary Kay lady to give me a makeover, ‘for her
portfolio.’ I tried to have a friendly conversation about things we
had in common (living in the Bay Area, the financial industry
meltdown, an interest in organic skin care products) and
everything–EVERYTHING–she said in response was either ignorant,
condescending or just plain wrong. My husband was eavesdropping
from the next room, and he wanted to yell, “Stephanie, STOP! You
don’t need to please people you don’t like!” The makeup job was
horrible, too. In fact, nearly every ‘conversation’ with someone
involved in a multi-level marketing business ends up like
this–full of cliches, lies, and false attempts at connection. MLM
is evil. Good conversation–when a regular client and I had a long
conversation about the vagaries of running and skiing as over-40
parents of young kids. She ended up buying a 10-session package at
the end of it, probably because I’d forgotten I was selling

    Maggie Patterson

    OMG Stephanie – this made me laugh so hard, because MLM is evil in so many ways. I am indeed in direct sales and I fully attribute my success in this business to being the exact opposite of the stereotype. People are always surprised, and it is no wonder when you have someone like this Mary Kay lady on the loose.


In some ways, whether you have a burn or an ace seems random. Is it? Is it contextual? Confidence due to…?

This is a good topic!

I’m going to give another example.

At my current work, when it comes to meetings or simply disagreeing with someone and putting my view forward, I find it can vary in success. I guess meetings are a little different to the one on one conversation scenario, but they are still small groups.

Last week, we had a meeting and I really felt like I had contributed. I spoke – and was heard – and left the day feeling really quite ‘up’.

But sometimes in meetings I either (a) stay quiet or (b) can’t get a word in (or speak but don’t seem to have been heard, even though I don’t whisper).

What was different about last weeks meeting? To the best of my thinking, perhaps because just one or two extroverts were away, which put me (a middle of the road introvert) more to the fore. That’s possibly an explanation. But that’s an external explanation.
Was it me at all? I’d rather it be more to do with me – because then I can do something about it.

Sorry if the small group scenario is slightly off topic!


I had a blind date a couple years back. My friend had set me up with her. She was pretty, but not much of a talker. Furthermore, we had nothing in common. I can’t remember a single thing about her, because no conversation material ever popped up. I kept excusing myself to the bathroom because I really needed to just escape how awkward the time was. I consider myself a decent conversationalist when I have to, but I just bombed that date. I think it lasted 3 hours. I haven’t gone on a blind date since.

I went in for an interview for an auditor position at a small firm that I wanted to work at. I really have no fear of interviews, so I am very relaxed and speak easily (credit to me being a teacher for 2 years). I walked out of the office feeling very confident about my interview. Later, I found out from my recruiter that the employer/owner of the small firm rejected me because he felt I was ambitious, overqualified (I wasn’t) and he’d have to pay me too much. πŸ™

Fun topic, Derek. I can’t wait to meet you when you head to Honolulu. You seem like a very charismatic person.


Ooooh, great question.

I once tried to give a compliment to a friend’s friend about her dress. Essentially, instead of it sounding like I was complimenting her on her unique (and beautiful) style, I came across as if I was telling her she dressed like a weirdo.


I did back track and use some more choice words, though, but in my head I was beating myself up for making a tool of myself in front of someone I didn’t really know that well.

I’ve aced a lot of interviews in my time – at least, I’ve not been turned down for a job. You know, it’s hard to think of a time when I thought, “holy mother of cheese, I am AWESOME at conversing”. Put me on a stage, and I really enjoy it, actually talking one-to-one is harder.


I think I bomb conversations when I feel like the person I’m talking to sucks as a human. You can suck as a human by being extremely self interested, lacking empathy, and being openly critical of one’s environment/other people. We all judge people based on personality and character and we all get unconscious vibes from the energy people carry.

The best conversations happen when I sense that the other person is genuine and open minded. I guess one example of an aced conversation is when I approached Kris Carr to tell her a story about how her work impacted my life. She responded by asking me to write for her, so I did. That was the catalyst that made me start my blog and it also formed a bond between us that I’m super thankful for.

I guess my advice is to not suck as a human, because people can tell where your interests lie (within minutes of meeting you).

    Andrea Saunder

    I think you nailed Derek’s spectrum of awkwardness thing there, Josephine. Those sucksome humans don’t even realise they are bombing πŸ˜‰

    Kinda in contrast, I notice I tend to bomb out if I’m talking to someone I feel is much more successful than me (whatever that means…). I get all intimidated and trip myself up.


      LOL – Thanks, Andrea… yeah. I totally hear you. The vision we have of our own self worth can trip us up completely. It’s really more than a self worth issue, but almost a self centered issue.

      Whenever I feel like I’m comparing myself to someone or feeling unworthy of their time, I tell myself to stop and take myself out of the equation.

      If you have a goal that’s meaningful to you, that you know could improve your life and the lives of others, you have to try to get out of your own way.

      We’re all a work in progress… at least those of us who read blogs like Social Triggers and other self improvement type blogs. We’re also really good at supporting one another and sharing the love. So, know that you’re worthy and be bigger and bolder than you ever thought you could be. And if you don’t suck as a human, you’re already winning! HA xo


When I bombed a conversation: The usual “How are you” “Fine
you?” “Fine … Well I have to go” Every time I meet someone who I
know somehow but I’m not real friends with someon. Always so akward
Aced: Recently I was riding the tram and a girl was wearing a big
backpack and we started to chat it was a 20 minute conversation
without any akward situations. After this I felt happy.

Lori Mofford

This one is easy for me as a Realtor! Telephone sales calls provide a myriad of challenges. Though I’m probably one of the only Realtors I know who doesn’t mind doing it!

There are times when I’m caught off-guard by the timing or language barrier or attitude. These calls can take the wind out of my sails and leave my pitch flat and fruitless.

On the other hand, when I feel prepared (when I intend the outcome), my conversations lead to real relationships and great new clients.

barbara trainin blank

I’ve bombed many job interviews and networking situations. Most recently, I wasn’t able to tell people succinctly (at one of the latter) what I do at my company and lost her interest and possible work. In contrast, years ago I didn’t get a job I wanted cause personnel preferred someone else, but the editor liked me so much he gave me many years of freelanc wruting work.

Andrea Saunder

At my very first networking event, I got into a conversation about sugar versus artificial sweeteners. I pointed to the cakes on the table and flippantly remarked that you were better off eating the cake than drinking a diet soda. After that I was known as the cake-endorsing health coach, which really felt embarrassing and limiting!

My favourite ever interview was the only one I’ve had conducted by a professional recruiter. I remember she was amazing at drawing the best stuff from me, it felt so easy and I was so confident. We did naturally ‘click’. At the end of the interview she even gave me a hug, handed me her card and told me if I ever wanted to try recruitment as a career to give her a call. And I got the job πŸ™‚

    Lori Stalter

    Hey Andrea,

    I’ve had similar conversations with people about how I’d rather see them eat sugar than eat or drink something with artificial sweetener if they’re determined to have something sweet that doesn’t come from natural sources. I feel your pain! After initial shocked reactions, I explain why the artificial stuff is so bad. But I can how someone would intentionally twist what you meant.

      Andrea Saunder

      Hi Lori,
      It’s good to know I’m not the only one that has dropped a sugar faux pas or two πŸ™‚
      On reflection, although it was kinda embarrassing (especially the Twitter comments after the event!), it did get people talking and thinking… it actually led to the guy I was talking to giving up diet soda, then another Twitter follower got on board with that and we had this Twitter support thing going on, which then led to me leading a talk at a local gym. I guess that proves the saying that there is no such thing as bad publicity, although I wouldn’t want to take that risk too often! πŸ˜€


    Great story!

      Andrea Saunder

      Haha thanks, Gil! Which one? πŸ™‚


Time when I bombed a conversation:

As a graphic designer, I have a lot of trouble explaining what I do to my family and to my friends.

This is a typical conversation in my asian family get-together.

My uncle: So what do you do for a living?

Me: I’m a graphic designer

My uncle: oh… so you make logos?

Me: (Really cannot be bothered explaining) uhmm yes…

Time when I aced a conversation:

I met a friend that I haven’t seen for quite a while. We decided to have lunch and as we were talking about his business, he told me that he needed some brand identity done.

One thing led to another, I got the job, he liked my work, I got referred to more clients and I earned a good some of money.

    Derek Halpern

    If you can’t be bothered explaining to people what you do, how can you expect them to understand it? πŸ™‚

      Rahat @WeeklyDesignGrind.com

      Yeah your right, but after repeatedly hearing the same question from the same people, you sort-of get tired of explaining it.

        Kelly Williams

        I would make it an experiment. Figure out different ways of explaining it to them until they get it. Chances are you will use some of the material in future conversations. Your family members cant be the only people who dont understand what you are telling them.

Stephanie B

When attending a Costume Party where I knew basically no one, I commented on a lady’s makeup and how it looked great with her costume. I noticed she snubbed me the rest of the evening. A while later, there was a picture of the host and that same lady posted on twitter in casual everyday non-costume wear- and her makeup was done exactly the same. Whoops.

Once I moved to a new town and didn’t yet have a job. When I started chatting up the tenant of an apartment I was interested in, I realized we were in the same field. Her boss was looking to hire someone, and I gave her my card. She passed it on and I got the interview and the position.

    Derek Halpern

    Why do you think that second conversation went so well. What did you do? What did you say?

      Stephanie B

      I listened to what she said and looked for a way to relate. I can’t remember exactly what I said, but the flow of the convo was smooth and natural and comfortable. I had confidence and was open since I was in a brand new place.


I recently bombed in an interview (was going for a different job within my organisation). I had a bad “fall” on the first question (that I lacked knowledge to answer), but worse than that was that it set me up for a real ‘flat’ mood for the rest of the interview. i.e. I didn’t recover.

I can’t think of a recent ace, so I’ll contrast the above with the interview I had for my current job. I was far more confident (and knowledgable) about the position, and I aced it. I felt comfortable, and when the trickier questions came, I got through it far more smoothly.

Confidence AND a knowledge base = aced conversation?

    Robert Kennedy III

    Confidence is the kicker. I don’t know if you ALWAYS have
    to have the knowledge base. But you should know where to GET the
    knowledge and provide the listener enough value that THEY become
    confident that you can do what you say. I’ve flubbed MANY
    conversations. Probably will flub some more too. But, I’m learning
    to be a straight as I can be, as authentic as I know how and not
    worry about how what I say will be used against me :-).

    Derek Halpern

    How did you respond to the question that you didn’t know the answer to?


      I really fumbled, and (even worse in an interview) admitted that I couldn’t understand it. I did my best to show that I had the skills and experience in similar areas to transfer to this new position, but it just left a flat feeling in the interview (or at least me feeling flat – and my nervousness then showed).

      In full disclosure: yes, I was a little annoyed at the question – as direct experience/knowledge was not required for this position, and I was a little annoyed that this was the first question of the interview. But, life (love, business, and job interviews!) is not always 100% fair! πŸ™‚

        Derek Halpern

        Let’s say you had the chance to answer that question again. How would you respond?


          Perhaps a more confident approach would have been to skip straight to admitting, “look, I don’t actually know the answer to that, but….” (and then do my best to make a couple points about how learning those specific skills won’t be a problem etc). What do you think?

Leave a comment