THE SECRET PURPOSE OF “POINTLESS” SMALL TALK

Small talk is often thought of as trivial or trite, but a lot more is going
on than you might think.
To “Make Small Talk” successfully is to create a state of comfort and
familiarity around new people. Instinctively, we seek to connect on a
primal, emotional level, so that we feel safe in each others hands.
It’s not necessarily the content of what is being said that counts, which
is why many of us miss the point. It’s the feeling of lightness, ease and
playfulness created by the conversation.
Usually this is the first step towards making a deeper connection with
others, and more often than not it’s a necessary one!
If we want more fulfilling relationships we better not get knocked down
at the first hurdle.
Here is a practical guide book to help you become more comfortable
with chit-chat.
If you practice the twelve techniques I have laid out for you, you will
become more confident in yourself and your ability to ‘make small talk’.
Who knows, you might even learn to love it!

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INTRODUCTION
Hi I’m Antony Sammeroff. You probably found me through my YouTube
channel or Be Yourself and Love It! Podcast if you’re reading this eBook,
but in case someone passed it along to you, I’ll briefly introduce myself
in a minute. First let me tell you a little bit about what you’re reading.
This little thing is a practical guide-book. It’s not a philosophical treatise,
or a feel-good psychological tract on “having the right mind-set” to talk
to strangers, get ahead in work, or find a partner. Having a good mind-
set is important for achieving anything, of course, but I believe the best
way to change your mind-set is by trying to do things differently from
how you’ve done them before. That way you can have new experiences
which change the way you see yourself in the world, and alter your
perception of what might be possible for you.
For example, if I were expected to run a half-marathon this weekend I
wouldn’t be too confident. I haven’t actually practised any long-distance
running so my lack of confidence would be completely justified. But
what if I got up at 6:30 AM and went for a run every morning for a few
months? Every day I’d get gradually more capable, and as my ability
increased so would my confidence. Fast forward a few years: I have a
bunch of marathons under my belt, someone gives me a call to ask me
to run a half-marathon for charity this weekend. I figure I can handle it.
You get me? Seeing myself getting better day by day has changed my mindset.
We are often extolled the virtues of being confident in ourselves, but
in my experience, confidence comes from results. Results come from
knowing what you are doing, and knowing what you are doing comes

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from experience. All the really good stuff is learned first-hand. You can’t
get confident just by reading a book. Sorry guys! You need to become
competent first. That’s why this little eBook is all about giving you some
practical tools that you can take out into the real world and experiment
with in real-life conversations without looking like a complete weirdo. If
you practice what I teach, you will gain new artistry in casual conversation,
and that will help you feel more confident in yourself and your ability to
handle social situations. If you’re anything like me, you might start to
feel less anxious and enjoy yourself more around other people.
I suggest you take these twelve tips and make a conscious effort to try
each one of them at least twelve times. If you do that, you will get a
sense of how they work and when each of them might come in handy.
Please don’t just read this and nod your head along thinking, “Yeah,
that totally makes sense!” That will get you nowhere fast. Ok? Practical
Application! Exclamation mark! Exclamation mark! Exclamation mark!
in Bold and Italics, underlined three times, with asterisks on either side. *** ***
I have put this book out to help you become better at expressing yourself.
Now wouldn’t it be awesome if it actually did that for you?
It will, if you choose to be my teammate in helping you. So learn well if
you would excel. I have done my bit, the rest is up to you.
If you consciously practise each tip a dozen times you will internalise
them just enough to be able to apply them without having to think
about it so much. If you keep at it, they will just become a natural part
of how you communicate – part of who you are.
You can read the book once through to get the idea of it, then return to

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the beginning and start again with Tip 1. Find opportunities to use it 12
times, then move on to Tip 2, and so on. If you need to remind yourself
of anything, don’t be afraid to read the relevant parts again and again.
Take your own notes and read them over and over again. This eBook is
short, but what you learn from doing the exercises could fill hundreds
of pages. In fact, you might want to get a journal to keep track of your
progress, write down the results of your experiments, and codify what
you have learned. We will start off with the most fundamental tools and
then get more esoteric as we go on.

A lot of the material here is are adapted excerpts from my forthcoming

book Represent Yourself!
I’m putting these bits out in advance for a few reasons. Firstly, I want
to make you aware that the book is going to exist one day so you can
follow me.
Stay tuned to my YouTube channel and Be Yourself and Love It! podcast
for updates. Secondly, I want to get people who watch my videos signed
up to my mailing list so I can keep them updated if anything big comes
up. If you didn’t get this by signing up to my mailing list, you can do
that here: www.beyourselfandloveit.com/mailinglist. Don’t worry about
spam, I usually only send out one newsletter a month.
The most important reason is that I don’t want this information just
sitting on my laptop when it can be out in the real world helping people.
It will probably be a while before I finish the whole book, so I thought
the best idea would be to spread some love around a bit early to wet

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people’s appetite. This way I’ll also be able to gather some feedback on
what people want to see in the final edition and what they think of my
ideas so far.

Finally, I did promise to say a little about myself for anyone that’s
interested. I’m an author and podcaster. At the beginning of this year
I put out a self-help book called Procrastination Annihilation. You can
download a free PDF of it at www.beyourselfandloveit.com/doit, or buy
it on Amazon Kindle if you prefer. I make a living by coaching and
counselling people all over the world on Skype. I’ve reviewed about
150 theatre productions, but it’s mostly a hobby. This year I put out my
first short book on economics out called Universal Basic Income – For
and Against. I guess I like writing about whatever I am learning about.
I’m a natural codifier, so I like to gather my new understandings and put
them together in an order that is easy for other people to understand so
that maybe other people can get a short cut.
Now, the purpose of a bio in a self-help book is never really to tell you
about me, the author. (What’s so important about me, anyway?) Usually
it’s used as an opportunity to show you that I’ve gone through similar
challenges to those you might be facing at the moment and have made
progress. That makes me relatable, gives me credibility, and gives you
a reason to listen to what I have to say in case I can help you out too.
I’m writing this one from a yoga retreat in India which I’m visiting for
the second time. It’s my third retreat overall. I never came out to India
to “find myself” or in search of enlightenment or anything new-age

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hippie like that (although all respect to those who do). I just came for
very practical reasons. There’s a lot I want to do with my life and I need
to be at my best to do them. Whatever my previous routines were; they
weren’t serving me very well. I’ve improved a lot since then and wrote
my first complete self-help book, Procrastination Annihilation, to share
how I did it. (The feedback was great, so here I go again.)
I was struggling to come up with a bio I was happy with before I left
Scotland. I didn’t really know what to cover since getting good at
casual conversation has helped me in so many ways that it was hard to
decide what to include or which angle to take. I’ve opted to just share
about what I have experienced recently while here. I’ve had a couple
of experiences here which have highlighted the positive change in me
over the last few years so I thought that would do the job.
Last time I was here I made friends on the first night with a girl, lets
call her Ellie. As soon as we met, we got entranced in a deep and
meaningful, personal conversation – a DMC, as a friend used to call
them. We spoke about her past and some of the difficult experiences
she had had in her life, as well as the challenges she was currently
facing that had led her to India. I related and gave some advice which
she nodded along to and took into consideration.
On one hand, Ellie and I connected instantly on quite a powerful level,
but then a few days later we were hanging out by the River Ganges,
laughing and joking merrily, and she turned to me and said, “I had no
idea you were like this when I first met you.”
What happened?

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Ellie and I clicked, so it was pretty easy for us to get on. On the other
hand, she still didn’t get an accurate picture of my full personality when
we met because I was too intense. Some of that is definitely acceptable
on a yoga retreat where everyone is there to work on themselves anyway,
but then what about when you meet someone in a bar, or pub, or club,
or at the reception? What about festivals, work events, and networking
meetings? What about when you meet someone you fancy and get
nervous? You need more channels to communicate on. Most of the
time, you have to build up to those kinds of conversation with people,
otherwise you’ll scare them away!
And another thing – why didn’t Ellie get to see my fun playful side as
well as my deep and meaningful one when we first met? Was I trying
too hard to make a good impression? Was I hiding something away?
Or did I just not know how to bring out those aspects of my personality
around people I had just met?
I’ve always had a part of myself that only seemed to come out around
people I “clicked” with, or on certain nights when I was in a good mood.
I used to wonder why I couldn’t be like that all the time, around anyone.
I mean, wouldn’t it be cool to be able to access the casualness and
fluency you have around people you’re already familiar with, rather than
have to wait around until you’re lucky enough to bump into someone
who is naturally on the same page as you? It would be good to have the
social skills to help you relate to anyone.
This year I seem to have instantly made friends with everyone, and I
did it showing off the same lightness and sense of humour my friends
back home know me for. A bunch of people have told me that I crack
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them up or that they think I’m hilarious! And, I have still shared plenty
of deep and meaningful chats in between classes. I have lost nothing
of my depth and passion, but I have gained more channels to relate to
other people on.
A few nights in, I told the friend I’m travelling with about the change I
saw in myself since I was last here, and how proud I was of myself. The
next day someone asked the address of my website. When I said it was
beyourselfandloveit.com he responded, “I’ve noticed you’re very good
at doing that.”
What I love the most is, there are people here that I know fine well
I would have been intimidated by in years gone by. Maybe because
they are less extroverted, or have different personality types from what
I was used to. I might have thought they were judging me, or would
not like someone as “out there” as I am. Or maybe that they would
think I was weird. Now I understand that some people just need a little
more warming up than others. Being more comfortable within myself
allows me to come across as more relaxed, playful and natural version
of myself – and invites them in and gives them permission to do the
same. Looks like I’m sharing the love! I have watched in awe as these
same people come over and cuddle me, or sit beside me at lunch to
have another laugh… or a DMC.
Case in point, I told one of the girls about my journey, and how I thought
that a couple of years ago the two of us may not have related so well
because I might have insecurely thought she was judging me or wouldn’t
think I was cool. I explained how I’ve come to understand that it’s not
personal, it’s just that some people have different emotional needs than
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others and take a little more time to open up or feel comfortable with
new people. It was a little anxiety provoking being so honest, but she
immediately started nodding her head along to my words with a look
of recognition in her eye. She confided in me that other people in the
past may have judged her as a “cold bitch”, but that she isn’t actually
like that, and that she’s been working on it too. She was touched, like I
was, and said, “It’s nice to be accurately read.”
It seems like the whole world has opened up to me at last!
I hope mastering the art of small talk will help you overcome whatever
blocks you from stepping powerfully into social situations so that you
can shine, and that the world opens up to you too.
Namaste, I suppose it would be most appropriate to say,
from India.

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SUMMARY OF CONTENTS
The Secret Purpose of “Pointless” Small Talk
Introduction
1. Give a Little More
2. Tell Your Stories
3. Treat People Like They’re Fascinating
4. Demonstrate Your Understanding
5. Change the Subject
6. Re-spark Dead Ends
7. Point out the Elephant in the Room
8. Learn How to Take a Compliment
9. Get Ready to Talk About What You Do
10. Avoid “Interview” Questions
11. Dig Deeper
12. Relate Your Answers to Yourself
Conclusion

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1. GIVE A LITTLE MORE
Most of the media on improving your social skills talks about the
importance of being a good listener and emphasises how much people
love talking about themselves. Listening is an important social skill to
be sure, but a lot of people will feel under pressure if you put them in
the spotlight and expect them to do all the work. It’s perfectly normal
to have to do 60-90% of the talking when you first start speaking to
someone new. As they loosen up and get more chatty you can ease
off the gas and let them do more of the talking. Listen to how talkative
they are (or aren’t). If they’re on a roll, you can step back and let them
do all the legwork. If they’re struggling, you can take up the slack. This
means learning to become more aware of what’s going on around you
and responding accordingly, rather than trying to fit your interaction
into an already existing formula. We call this “social calibration”; and
it’s something you can definitely get better at with practice. In fact, this
whole book is about helping you get better at calibrating your social
interactions with others.
To begin, the easiest way to build familiarity with someone new is to
get used to talking like you are already familiar with them. People who
know each other only occasionally ask direct questions. Most of the
time they just riff off one another, making related statements. They
take turns at saying what they think or feel and contributing to the
discussion in a free flowing manner. That doesn’t mean that it’s never
helpful or appropriate to ask questions. It just means that it’s important
to get good at sharing details of your own volition. Volunteering more
information gives people details that they can hook onto to spark their

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own imagination. It helps them think of something to say themselves.
For example, if I say something like “I’m from Glasgow,” someone might
ask where that is, and I can say it’s in Scotland. Then they might say,
“Oh that’s nice”, but you can already see the conversation tapering
off to nothing and coming to a dead end. On the other hand, if I say,
“I’m from Glasgow, it’s the biggest city in Scotland, but the capital
of Scotland is actually in Edinburgh. Some people say that Edinburgh
looks nicer, but the people in Glasgow are friendlier…” I am giving the
other person much more to work with. They can talk about Scotland,
compare big cities to small cities, or talk about a rivalry between their
city and another one. They can talk about places that look nice or ugly,
or places with people who are friendly, and others where they are nasty.
Overall, the conversation is far less likely to fall into an awkward silence.
A simple trick to get better at doing this is to simply add an extra
comment on to anything you say. Instead of saying, “I also like cooking,”
say, “I also like cooking, but it can be stressful if I have to prepare more
than one dish at a time.” It’s easy to practice! The advantage of this is
that it gives the person more to respond to. In the first instance they
can only say something about cooking or risk changing the subject at
the possibility of making the conversation awkward. In the second case
they can agree, say they experience something differently, mention
another situation that they find stressful or overwhelming because they
have to do more than one thing at a time, or anything else.
Once you have tried adding one extra comment a few times, then try
adding a comment on your comment. “I also like cooking, but it can be
stressful if I have to prepare more than one dish at a time. I’m probably
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better to sticking to one thing at a time in general actually, multitasking
isn’t my strong point.” This is really the makings of a confident speaker.
Now there is some personal material to discuss, such as feelings on
multi-tasking and general human foibles. So, my first tip to help you
become a better conversationalist is to try, at least a dozen times, to
add one or two more details to what you say in a conversation to give it
fuel. Tack something extra on the end of what you just said.
Above all, don’t be hard work. Avoid responding to questions like, “What
have you been up to?” with answers like “Not much,” or “Same as
always”. If someone says, “How’s it going?”, don’t just say, “It’s going
good,” or, “Fine, thanks,” and leave a vacuum. I hate it when I have to
ask people question after question to get anything decent out of them.
Add a detail or two as a conversation starter. Give people something to
work with.

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2. TELL YOUR STORIES
Stories are the real currency of human interaction. We relate to each
other by exchanging tales from our lives. To avoid remaining in the
realms of conceptual chit-chat, use the conversation to tell related stories
from your life. That makes things more personal. The more engaged in
the conversation someone is, the longer the stories you can tell. Early
on only tell short anecdotes. Later on, you can regale people of your
favourite yarns and funniest stories from your life. Practice telling them
to many people until you become good at them. A gripping saga is a
lovely thing to be able to offer, however epic or trivial. It also may give a
deeper insight into who you are and how far you have come.
To give you something more specific to practice, let’s look at an advanced
variation on our last exercise. This time, instead of just tacking on a
comment to a previous statement, what you can do is add on a micro-
anecdote. I coined the term micro-anecdote to capture the idea of
offering just a little detail from your personal experience or a little story
from your own life that exemplifies what you are saying.
A full-length anecdote may demand too much time and attention from
another person right at the beginning of an interaction, or if they are in
the middle of a train of thought. Micro-anecdotes, on the other hand,
can be told quickly in a sentence or two.
Instead of saying, “I also like cooking, but it can be stressful if I have to
prepare more than one dish at a time.” You can say, “I also like cooking,
but if can be stressful if I have to prepare more than one dish at a
time. I used to chase my girlfriend out the kitchen when I was cooking

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because I got so stressed that I’d snap at her if she tried to speak to me!”
You can see how a little anecdote like this can really spice up
conversations by anchoring what you are saying to your personal life in
a totally relatable way. They create more opportunities for connection
by opening avenues of conversation that are far more personal. Of
course, you would have to be able to remember a story or detail that
was relevant to use one. (Unless you’re planning on making them up
as you go along!) If you make a conscious effort to think of micro-
anecdotes and slip them into conversation, then perhaps you will get in
the habit or recalling your cute and funny little stories more often.
It’s good to make a special effort to prepare in the beginning. If anything
funny or quirky happens to you during the day, write it down or save it
on your phone. Get used to doing it. Keep a little note to read before
you go out somewhere where you will have to make conversation (or to
read in the bathroom if you get stuck for things to talk about). These are
the little things that your life is made of, don’t keep them to yourself!
Micro-anecdotes don’t always have to be “interesting” or “useful” or
“funny”! Just the fact that you are sharing a detail from your own life is
compelling and makes an interaction more personal. If you listen in to
people around you talking, you will notice that they often slip little details
in without even thinking about it. It’s just a simple means of rapport-
building. If you put pressure on yourself to always be fascinating then
other people will feel under pressure to perform as well and they won’t
like it as much. By sharing freely and unselfconsciously you give other
people permission to do the same.

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3. TREAT PEOPLE LIKE THEY’RE FASCINATING
I don’t mean to sound like captain obvious here, but if you take an
interest in others they are more likely to enjoy talking to you. If you
behave as though they are worth listening to, they are more likely to
shine and step up to meet your expectations, so you might have more
fun too. Treat people like they’re fascinating. They might just pleasantly
surprise you!
People are rarely boring talking about the things they really care about, so
here’s a trick to save yourself from being bored to death by meaningless
small talk. Consider: What might this person be passionate about? If
you don’t know yet see if you can find out. If you want an exercise you
can imagine yourself a private detective searching for what the other
person loves to talk about and give them lots of opportunity to discuss it.
Show interest in the details and get them to expand on what they have
said. Zoom in as though you were on Google Maps, and then zoom
in again. Connect on these points by asking questions that will gain
you an understanding of why they feel that way and then demonstrate
that understanding by showing you get them. Make statements about
your thoughts and feelings on topics that interest them to give them
something to work with and expand upon.
If you can consistently get people to talk about what they are passionate
about they will associate all those great feelings with you and love
speaking to you. And why wouldn’t they? You’re a great conversationalist
who listens well and asks the right questions.
If you are genuinely curious you need never be at a loss for something

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to say. If you are not genuinely curious it’s probably because you are
insecure and seeking validation by talking a lot (I used to do it.) Use the
“fake it till you make it” approach. Act curious until you find the value
of being curious. Then you won’t have to act.

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4. DEMONSTRATE YOUR UNDERSTANDING
Another thing you can get good at doing is stopping to paraphrase
what the other person has said in a sentence to make sure you have
understood them correctly. Once you’ve done that just wait for their
response. Usually either people will say something like, “Yes! Exactly!”
enthusiastically and continue to reveal a deeper layer of their story, or
they will correct you slightly before going on. Don’t worry about getting
it wrong. Even if you don’t get someone exactly right they still usually
feel better understood for your effort. If they have to correct you and
explain what they actually meant it helps them get clear where they’re
at in their own head. Here are some quick examples to give you the idea:

EXAMPLE 1:

Speaker: “I’ve just broken up with Jared. It was hard to do but the
way he was treating me just got too much to take. Every time I tried to
discuss it with him he would just clam up.”
Paraphraser: “Yeah, it sounds like you tried to talk it out but he wouldn’t
be willing to have the conversation.”
Speaker: “I did, I tried! I feel much better now, I’m moving on.”
Paraphraser: “I guess you’ll be looking to the future now.”
Speaker: “That’s right.”
Paraphraser: “I remember when I broke up with my ex… [tells a related
anecdote]”

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As you can see you don’t even have to paraphrase everything the other
person says to give them the sense that they are being understood.
Taking out one main theme can have the same effect and will usually
be enough to get them talking. Once the other person feels adequately
understood to the point they don’t feel they need to expand you can
take the baton and run with a personal anecdote of your own, creating
a sense of relating backwards and forwards. This stops you from falling
into the role of playing therapist for friends and acquaintances which
can leave a sense of imbalance that can leave people feeling awkward
afterwards. When you share too it creates a more even dynamic. Just
make sure the other person is done venting first or it might look like
you’re butting in with your own stuff or hijacking the conversation to
make it all about you. Give and take!
A simple variation on this approach is to simply repeat the last thing
people have said back to them, inviting them to add something more.
“I came in late and the cat had been sick on the carpet!”. “You came
in late and the cat had been sick on the carpet.” “Yeah it was a real
mess… etc.”
You can also simply put names on the emotion underlying what people
are expressing: “That sounds disappointing”, “I bet that was stressful,”
“How frustrating!”, “You must have been furious!” This has a similar
effect. I have noticed since I began practising this many years ago it has
become part of how I regularly speak and I overhear myself automatically
saying things like, “You sound really excited about that!” – people like it.
These are critical skills taught to therapists and coaches, but really they
should be taught to everyone because they are invaluable to fostering

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connection and understanding.
Receive sadness with understanding. Receive enthusiasm with
enthusiasm. The next example relates to receiving positive emotions in
a similar way:

EXAMPLE 2:

Speaker: “I’m really excited! The holiday resort my parents booked for
our trip to Switzerland is right across from a skating rink – I’ll be able
to practice every day!”
Empathiser: “Wow – you really love ice skating!”
Speaker: “Totally! I started when I was a little but I stopped for years
when I was in high school and I only just started getting back into it a
couple of years ago. I usually only get to go every couple weeks.”
Empathiser: “Sounds like you’re excited to get a chance to do more and
really throw yourself into it!”
Speaker: “Yes I am, have you ever been?”
Empathiser: “No, but I have gone skiing. Maybe you can take me some
time and show the ropes – I mean, rink.”
Speaker: “Haha yeah, that would be fun. Maybe when I get back.”

This works so well because there is nothing worse than being enthusiastic
about something only to receive a lukewarm or disinterested response.
It kills our joy of life. This is too typically our experience as kids as well,
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when parents are too distracted to listen. It’s a gift to be able to receive
someone’s else’s excitement and echo it with your own.

For more on how to listen well, type any of these into YouTube to find
my videos on them:
Can Empathy be a Learned Skill? 3 Approaches! (Antony Sammeroff)
Don’t Brightside Me, Bro!
Empathising With Your Kids – Some Approaches

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5. CHANGE THE SUBJECT
I know this might shock you, but if the topic of discussion doesn’t
interest you, you are actually allowed to change the subject. No one
wants to feel like they are boring you. Or to hear you talk monotonously
and unenthusiastically as if it’s a chore.
If there are things that you know you don’t like talking about, such as
work, you should note them down and prepare a specific transition from
those topics into topics or anecdotes that you actually are interested in
talking about. This is not hard to do at all:

EXAMPLE 1:

Question: “Where are you from?”

Answer: “I’m from Italy...”
Segue: “...But I came here to study my Masters in Biotechnology...”
New Topic: “...I’m interested in the environmental side of it. You can
turn vegetable peelings into carbon fibre rods which can be made into
bicycles or skateboards that are almost completely recycled.”

EXAMPLE 2:

Question: “What do you do?”

Answer: “I’m in a call centre with this company...”
Segue: “...we mostly take incoming calls, it pays the bills, but my

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favourite thing about the work day is coming home!...”
New Topic: “I like to relax with my cats and my boyfriend. One is called
Mixie and the other one is Daisy. They don’t get along too good so
sometimes I have to put one of them out. Usually it’s him – haha!”

These are examples from characters that are clearly tired of talking
about where they are from or what they do. They were clever enough
to prepare to respond to those questions since they come up all the
time. What’s more, they gave answers that were either entertaining or
fed into topics they were more interested in talking about.

You are responsible for your own experience of the world and it’s
your job to work on making it one that is favourable to you. It’s your
responsibility to make your interactions enjoyable, and if you take that
responsibility seriously you can learn how.
First you need to know what you are actually interested in talking about,
so it might benefit you to write down a quick list. If you need to, have
questions prepared as conversation starters. I will suggest some later.
Anything will do, but try some out to see which create good conversations
reliably. Memorize a few.

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6. RE-SPARK DEAD ENDS
If you feel self-conscious in social situations, that’s fine. It just means that
you are operating outside of your comfort zone. If you are aware of that
then you can use it as an opportunity to learn. The more experience you
get moving into the unknown and attempting some of the approaches
we are learning, the more comfortable you will become in your own
skin. Think of these as growing pains. There’s no need to let the inner
turmoil show. Breathe deeply, take your time, and think of something to
contribute. You can pause if you need to, or even stop and say, “Hmmm,
let me think about that one...” You’ll be fine.
You can re-spark a conversation in several ways, for example:
• By asking a question on the previous strand of conversation: “So
you were saying you went rafting. Are you always so adventurous
or was it a one off?”
• By giving more information about yourself with many points the
other person can riff off of: “I can never finish a cup of coffee before
it gets cold. I always start one and then begin doing something on
my laptop and then forget about it. I tried pouring half a cup but I
couldn’t finish that either. Then I tried a quarter, but once I poured
the milk in it was already too cold so I poured in more water and it
ended up being a half. It got cold.”
• Tell a related (or even unrelated) micro-anecdote: “That reminds
me of my birthday party when...”
• Ask what they are doing for the rest of the day or week.

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 • Comment on something that is going on in the environment. “Look
at that bird outside,” “It looks like they’re going up for more snacks,
it’s making me hungry,” “I like the way you’ve done your nails, what
made you choose that colour?”
• Say, “Let me show you something cool,” and have a trick prepared,
or cool picture or funny meme or video to talk about on your phone.
• Tell them a random fact: “Did you know in 2006 someone tried
to sell New Zealand on eBay. The price got up to $3,000 before
eBay shut it down.” It’s better if you can comment on the fact,
e.g. “I bet it wasn’t even the real owner who put it up there,” or, “I
don’t think it’s actually worth that much.” You have to be prepared
to continue the conversation so don’t choose a fact that will likely
lead to another dead end. If you Google up some facts that you
don’t know anything more about and they start asking you for more
details it could get awkward.
Another thing you should do is have four or five pre-prepared
conversation-starter questions memorised. So write some down and
test them for efficacy a few times each. Keep the ones that work.
Remember, if you fail to prepare you prepare to fail!
Finally, you can reignite a conversation by using the technique of
“pointing out the elephant in the room”, which is our next tip.

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7. POINT OUT THE ELEPHANT IN THE ROOM
If things do reach a dead end, or get awkward, you can always point
out the elephant in the room. In the ancient story about the foolishness
of conformity, The Emperor’s New Clothes, no one is willing to mention
that the Emperor is wearing nothing for fear of looking stupid. Everyone
feels uncomfortable about it, but it takes an innocent child to point out
what they are all actually thinking.
We laugh at silly stories of people who let themselves be swayed into
doing things despite their better judgement, in fact, the sitcoms and
teen movies are full of outrageous examples of awkward sympathetic
characters doing just that, partly because their plight is so relatable!
An “elephant in the room” is something that everyone sees but no one
dares to mention for fear of being impolite. Like an awkward feeling, bad
smell, ill-timed comment, accidental breach of etiquette, or anything
really. Sometimes someone says something that could be interpreted
as a sexual comment, and everyone knows, but no one dares laugh in
case they seem rude.
Often if someone “points out the elephant in the room” it breaks the
tension. Here are some examples you might be able to use. In the
future you can think of your own:
• A joke you tell doesn’t land: “Well, that went down like a lead balloon.”
• You forget what you are about to say: “My mind’s just gone blank,
give me a second.”
• You have each forgotten each other’s name: “Sometimes when you

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 meet someone you’re so busy thinking of what to say next that you
don’t really take it in when they say their name. I’m ______.”
• You don’t know how to answer a personal question: “I’ve never
considered that before, give me a moment to think about it.”
• Someone asks you about something expecting you to know more
about it than them but you don’t know the answer: “I don’t know
actually. How could we find out?”
• You all feel a bit nervous: “These gatherings can be a bit weird when you
first meet people and you have to think of something to say.”
• Someone says something that could be taken as a sexual innuendo
and only notices afterwards: “That’s what she said”, “I bet you say
that to all the girls/boys!”, “...said the actress to the Bishop.”
• Someone asks you for details about a random fact you just told
them and you don’t know the answer: “I have no idea, I just Googled
random facts earlier and that is what came up.”

Yesterday I was on the train talking to a fellow traveller for an hour

or so. She had been sipping some red wine out of a flask which she
shared with me. She had encouraged me to speak to her friend on the
phone, whom I teased playfully and flirted with just to amuse the three
of us with my boldness. Afterwards I asked my new friend if she had a
selfie of her with her friend that I could see on her phone. She made a
strange face as though implying that my request was weird, then asked
me to confirm that I really wanted to see one. I responded confidently,

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“I don’t want to see it if it’s weird. I only want to see it if it’s not weird.”
By pointing out the elephant in the room I helped my travel companion
feel comfortable explaining her reaction. She said: “It’s just I’m not
really much of a pictures person, I don’t like pictures of myself. She is
always wanting to take selfies with me, but I’m not into it.” So, it wasn’t
all about me after all!
She took out her phone after explaining and looked for a picture to
show me. This was an excellent example of “pointing out the elephant”
going right.

Be careful though! Sometimes pointing out the elephant in the room

can backfire and make things more awkward. For example, if you point
out that someone else seems a bit nervous, they may be thankful that
you have acknowledged them, or they might just feel even more in the
spotlight and be unhappy about it. Use your own discretion. Be prepared
to add an additional comment to what you have said to reignite the
conversation after you “point out the elephant.”

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8. LEARN HOW TO TAKE A COMPLIMENT
A lot of people can’t seem to take a compliment. They think it’s modesty
but it just makes things awkward. So don’t point out your weaknesses,
say it was nothing, or claim it was all luck – you’re refusing a gift!
If you can’t take a compliment and make things go awkward whenever
you receive one, it’s time to learn. A lot of people turn it around by
giving the other person a complement straight after. That can work
sometimes, but often it will just make people feel like you haven’t really
accepted what they’ve tried to offer you. One thing you can do is just
say, “Thank you,” and make a comment on what they have said. For
example, if someone says, “I love that shirt you are wearing,” you can
respond, “Thank you, it’s my favourite one actually, I got it in Holland
when I was on holiday visiting a friend.” There you go, fixed!
Practice 12 times.

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9. GET READY TO TALK ABOUT WHAT YOU DO
Everyone is going to ask you what you do sooner or later, so you better
get ready to deal with it. It’s amazing how so many of us squirm when
asked this question, and yet we know fine well we’re going to be in it
again and again ahead of time so we really have no excuse not to plan
ahead. Here is how you can start to prepare something interesting
to say about what you do, whether you like it or not. It’s an excellent
exercise, if I do say so myself (and I do.)
First, begin by writing down your job description.
Next, look through this list of questions and think of answers to as many
of them as are applicable to you. Be prepared to pick two answers that
stood out to you or struck you as compelling:
• What is one thing you like about your job/course of study?
• What is one thing you don’t like about your job?
• Is there anything about your character that is perfectly suited to your job?
• Is there something that you think is ironic about you doing your job?
(e.g. Socialist working in a bank, accountant who does stand-up
comedy, vegetarian working in burger joint, not fitting the stereotype
of someone who works in your industry.)
• What would you say are one or two important qualities that you need
to be good at your job?
• What is something interesting about your job that most people might miss?

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• Is there a perception that most people have about your job which is
false? Or is it totally true in a funny way?
• Is there a way that someone you work with totally fits the stereotype
of the job you’re in?
• How well do you fit in, or badly do you not fit in, with the crowd at work?
• When did you know you were going into your profession?
• What did you want to be when you were little and what was the
journey from wanting to do that to doing what you are doing now?
• What job or jobs do you think would suit you better than what you are
doing now and why? Why are you doing what you are doing instead?
• What can you see yourself doing in 10 years and how do you intend
to get from what you are doing now to there?
• Does your job make you happy/fulfilled and why or why not? If not
what would you rather do instead and why would it fulfil you? (If you
have a plan to get there, add that too.)
• Did something happen to inspire you to choose your profession or
did you just kind of fall into it?
• How long do you want or expect to stay in your current position and
what would be the circumstance of you changing position?

Write down your answer to the two questions which most struck you.
(You can do more if you want.)
Take your job description and two details about it and start forming
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them into a short, interesting paragraph about what you do. Get your
phone and record yourself reading your paragraph. Listen back and
correct any wording that sounded more natural written down than
spoken out. What you say should sound natural and buoyant. If you
have only negative things to say about your work that’s fine because
negative things are relatable, but you should tell it in such a way that
makes it funny in a cynical way, or can provoke a groan. Don’t give
people sob stories. Keep practising until you sound natural, confident
and compelling to listen to. Add little details which might spark curiosity
in others and make them want to know more. You can practice several
different versions until you find one you really like. If you’re smart, you’ll
try each of your answers 6-12 times with different people and see
which one comes off best in the real world.

Many people feel self-conscious and sound lifeless talking about their
job. Especially if their job is something that other people might consider
boring, such as working in computing or being a consultant. If you don’t
like your job you can talk about what you’ve learned from it which might
make it a stepping stone to better things in the future. But whatever you
do – Own It!

Take some cues from this hypothetical would-be Casanova:

Girl: “So what do you do?”
Guy: “I’m in IT.”

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Girl: “Oh. That doesn’t sound fun, do you still live in your parent’s
basement?”
Guy: “Attic. Better Wi-Fi up there. Actually, you’d be surprised, it’s really
interesting because you never know what problems will come up and
you get to help people by simplifying things that they find complicated.”
Girl: “Oh, so you like working with those computers then?”
Guy: “Yeah it’s excellent, let me show you something I’m working on
on my phone…” (talks her through a project and explains what is
interesting about it.)

By not accepting a judgement of himself as subordinate, or his profession

as inferior, he paints himself in a good light and leads the interaction
into something that could become more.

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10. AVOID “INTERVIEW” QUESTIONS
We are all probably familiar with the dreaded “interview” conversation.
It starts with, “What’s your name”, runs through “Where are you from?”,
to, “What do you do?” (the most common and often disliked question of
all), and finally reaches absolutely nowhere at all. At least not anywhere
anyone likes. It’s boring as Hell, and both people can’t help but despise
themselves (if not one another) for not knowing how to do anything
except politely comply with convention, the constraints of the dialogue,
and popular decorum.
Don’t just ask the standard, boring questions like, “What’s your name?”,
“Where are you from?”, “How are you?”, “What do you do?”
These questions can actually be OK for getting to know a little about
someone, but you have probably experienced how uncomfortable and
unnatural it feels when you meet someone and all any one of you can
seem to do is reel off a list of clichéd questions in the hope of generating
a conversation.
Give it at least fifteen minutes before asking a generic question if you
can. Half an hour is better.
Here are some examples of other questions I sometimes use as
conversation starters:
1. IMAGINATIVE QUESTIONS:
“If you could have any superhero power, which one would you
choose?” “Why?” “Would you use your powers for good or for evil?”
etc.

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2. QUESTIONS ABOUT ASPIRATIONS:
“If you could wake up tomorrow in any country, with any job you
wanted, where would you be and what would you be doing?”
3. QUESTIONS ABOUT THEIR TALENTS:
“What is one thing you’re good at that might surprise me?”
4. QUESTIONS ABOUT THEIR PEER GROUP:
“Who is your favourite person in the world?”
5. QUESTIONS ABOUT PREFERENCES:
“Are you a cat person or a dog person?”
“Who do you prefer, Batman, Superman, or Spiderman?”
6. QUESTIONS ABOUT MEDIA THEY LIKE:
“Is there a character from a TV show, film or book you have always
really identified with or just found really compelling?”
7. QUESTIONS ABOUT TRAVEL:
“What is your favourite place you’ve ever been?”
8. QUESTIONS ABOUT HUMAN FOIBLES:
“If people got arrested for bad habits, what would you be put in jail
for?”
9. QUESTIONS THAT NARROW DOWN TO A FEW PREFERENCES:
“What are the three things you would take with you to a deserted
island?”,
“You can only eat five different foods for the rest of your life, what
are they?”, etc.
These are just ideas to spark your own imagination. You can memorise

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three of them and try each of them a handful of times to see which
spark interesting conversations for you and which don’t. Then try
another three. After a while it would be better to start thinking of your
own out-of-the-box questions. Even better if you can learn to think of
them spontaneously. These are just training wheels, you don’t want to
become dependent on them! (Plus I don’t want a million of you going
around using the same conversation starters as me!)

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11. DIG DEEPER
As we have discussed, the question, “What do you do?” is bound to
come up sooner or later. Whenever that happens, a fork opens up in
the road. The well trodden path goes: “Oh that’s interesting, how did
you get into that?”, “Who do you work for?”, “How long have you been
doing that?”, “Do you enjoy it?”, “Where are you based?”; and ends in
a loss of the will to live. The road less travelled goes something more
like this:
• “Have you always wanted to do that since you were little?”, or,
• “Really? that surprises me! I thought you would do something more
like...”, or,
• “What would you say are the three most important qualities that
someone needs to be good at your job?...”
Big difference, right?

These questions demonstrate that you are more interested in the person
you are talking to than the details of their job. Some more examples of
questions that will elicit deeper responses are:
• “Does it make you happy/fulfilled?”
• “Is that something you chose to do or did your parents pressure you
into it?”
• “Did something happen to inspire you to choose it, or did you just
kind of fall into it?”

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• “How long do you want/expect to stay in that job?”
• “Can you picture yourself doing it in 10 years’ time?”

The so-called “predictable” topics do not have to remain boring or

predictable if you can master the art of exploring what a person’s
answer says about them, their lives, and what they value.
Instead of just asking, “Where are you from?”, you can ask, “How does
living here compare to other places you have lived?”, or, “What was
it like adjusting to moving here? I would imagine if I moved to a new
place where they spoke a different language I would feel...”, or “When I
first moved here… [reveal something about your experience of moving
to a new place] ...what was it like for you?”
Instead of asking, “Why did you choose to study that?”, you can
ask, “How do you study? Are you a conscientious student or a real
procrastinator?” The idea is to get people talking about their feelings,
values and experiences rather than factual details so that they relate to
you better. This is the art of digging a little deeper.

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12. RELATE YOUR ANSWERS TO YOURSELF
By the same token, people will likely be more interested in finding out
about your feelings, values and experiences than the details of your
profession or where you grew up. Even if you are good at making your
work sound fascinating, chances are it’s because the way you talk
about it conveys human interest and makes you relatable. If you master
this, you can use even the most banal “interview” questions (“What’s
your name?”, “Where are you from?”, “How are you?”, “What do you
do?”) as an entry point to deeper connection.
Your hobbies, where you’re from, where you live, where your name
came from, what your goals are, and so on. All of these can be used as
a starting point for talking about what they say about you and what they
mean to you. You probably want people to be interested in you rather
than your job, don’t you?
Relate your answers to yourself. Take some time to figure out what
the story is. How does what you do, or where you’re from, or what
you’ve been up to recently, say something meaningful about you? How
can you make it interesting, engaging, and relatable. What is universal
about it? Irony, imperfection, almost-had-it-but-missed, finally-got-it,
companionship, not feeling understood, being misunderstood, feeling
passionate about something, profound time spent alone, having talents
finally acknowledged or appreciated. These are all examples of excellent
universal themes that often underlie simple experiences. I’m sure you
can think of many more.
So, to put this wisdom into practice, one thing you should do is write

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down a list of questions you are likely to be asked on a regular basis,
for example:
• “How are you?”
• “What’s your name?”
• “What have you been up to?”
• “Where are you from?”
• “Where do you live?”
• “Where did you grow up?”
• “What do you do?”
• “How did you get into that?”
• “What are your hobbies?”
• “What is your passion in life?”

Remember, there are questions you are liable to be asked over and
over again, so you’ve got every reason to have good anecdotes ready
regarding each of them. Why not? If you’re going to have to talk about
it anyway you might as well be prepared to sound interesting and
enthusiastic rather than boring and generic.
Write down a simple answer next to each one, and then expand on it.
Once you are done, expand on it again. For example, “I live near Paris,”
is not as good as, “I live in a little town near Paris called X, it’s famous
for Y,” which is not as good as, “I live in a little town near Paris, it’s

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about a half hour drive from Disney Land. I took my son there last year
for the first time and he was thrilled, but we had to wait practically an
hour in the queue for each ride! He seemed perfectly happy though.”
What makes the second better than the first, and the third better than
the second? In the second case more details are given. In the third case
there is a whole range of human emotions expressed which anyone
can relate to and riff off of. Lets compare the first and final answer:

Question: “Where are you from?”

Answer: “I live near Paris.”
Suggested topics: Paris, Near Paris, France, French, Europe, etc.
All these topics are very factual. The other person will have to take on
the role of relating what they say to their own personal experience if the
conversation is to go more from mental chit-chat on facts to something
deeper and more meaningful.

Question: “Where are you from?”

Answer: “I live in a little town near Paris, it’s about a half hour drive
from Disney Land. I took my son there last year for the first time and
he was thrilled, but we had to wait practically an hour in the queue for
each ride! He seemed perfectly happy though.”
Suggested topics: Paris, Near Paris, Little Towns, France, Disney Land,
Holidays, Tourist Attractions, Children, Long Queues, Pet Peeves, etc.

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In this case there are also factual topic suggested, but it would also
be easy to exchange anecdotes or relate to “thrilling” experiences,
frustrating experiences of having to wait, having cheerful kids or being
bored ones. An infinite world of possible conversations to share open up.
As I said before, we are always told to be good listeners, but no one
ever mentions the importance of being able to deliver a few sentences
with reasonable confidence that will make it easy for other people to
respond to us.
I’m sure if you spend some time thinking about it you’ll be able to come
up with stories and interesting responses to these questions as well. If
you are smart you will have a funny anecdote to tell if someone asks
about your name, profession, place of birth, place of residence, and each
of your hobbies. For example, I have a story about my surname, which
is Sammeroff. It sounds Russian and sometimes people ask me about
it. When my great grandparents came to Scotland in 1905 to escape
persecution in their homeland of Ukraine, their name was transcribed
as Summeroff. When my grandfather went to school he was teased
by other children who would say, “Summer off, Winter on, Winter on,
Summer off...” so he decided to change his name to Sammeroff. Later
on he lamented that he couldn’t believe he was so stupid as to only
change one letter when he could have changed it to something neutral
and British sounding like Summers, but I’m glad he didn’t as now I’m
the only Antony Sammeroff in the world!

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CONCLUSION
This is my first attempt at a communication skills “toolbox”. I hope you
liked it. Well, you probably did if you’re reading on this far, let’s face
it, so thanks! Please follow my YouTube channel for more tips to on
becoming better conversationalist, have more fulfilling relationships,
and other awesome stuff yet to come.
Reading back through this little eBook has helped me realise how far
I have come as a communicator and that a lot of what I was missing
as a communicator could be broken down to a weakness in simple
component skills that could be tackled with specific practices one by
one. If someone had given me this little manuscript long ago and I had
actually practised the exercises it probably would have saved me years
of trial and error, so I hope you will practice well and get whatever
results you are looking for. If you become more confident as a speaker,
it will make it easier for you to enjoy being you in social situations.
I’m looking forwards to continuing to learn new things and to share
them. If you have any feedback on the text or would like me to write
about anything in future, please email: [email protected].

COACHING

If you feel like you would benefit from personal coaching in improving
your social skills or romantic life, email: [email protected].

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ACKNOWLEDGEMENTS

Thanks to my happy helping proofreaders, Suzy Berry and Chelsea

Ellen. If you want Chelsea’s help proofreading your book or project
email her at [email protected].
And to Lauren Johnston for doing the design on this eBook. If
you would like her help with design her professional address is:
[email protected].
I also want to thank all the strangers in bars, clubs, festivals, events,
coffee shops, yoga retreats, and sometimes even on the street who
didn’t even know they were my teachers. I owe this book to your tutelage.
Thanks to the people who attended my workshops on improving social
skills for helping me learn how to teach as well.

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SOME ADDITIONAL RESOURCES ON IMPROVING YOUR
COMMUNICATION SKILLS

Authentic Relationships
https://soundcloud.com/beyourselfandloveit/authenticrelationships
Communication Basics that Everyone Should Know
https://www.youtube.com/watch?v=uGTLst6SEcc&t
The Six Reasons Why People Communicate
https://www.youtube.com/watch?v=vxd6xWf06EU
How to Change Someone’s Mind
https://www.wakingtimes.com/2015/02/13/change-someones-
mind
Choose the Right Partner at the Right Time for the Right Reasons
https://soundcloud.com/beyourselfandloveit/petegerlach1
Dealing with Unreasonable People
https://www.youtube.com/watch?v=HWbqPVdSfa4
Dealing with Aggressive and Manipulative People
https://www.youtube.com/watch?v=sE57p4xcZjk
4 Predicates to Authentic Relationships
https://www.youtube.com/watch?v=mtMZ2O58BSU
5 Ways to Start a Conversation with a Stranger
https://www.youtube.com/watch?v=uyUwnGZ9YCo
No More Shouting Matches Ever!
https://www.youtube.com/watch?v=XM98bHgZRvQ

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How to be an Exceptionally Good Friend!
https://www.youtube.com/watch?v=IZEczbrZpWU
How to Solve Relationship Problems
https://www.youtube.com/watch?v=ZW0-0TlEEU8
Many more to be found on my YouTube channel
https://www.youtube.com/user/EnrichYourLife1/videos

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