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Even the most prominent voices in Sales were crap at Sales once.
Join bestselling Author, Founder and Sales Coach Mark Ackers as he speaks with successful Sales professionals about their early Sales struggles, and how they overcame these challenges to become the people they are today.
Mark Ackers: Listen. It's hard
work making a podcast. I want
to know that it's worthwhile.
Like, subscribe, share, show
me that you enjoy it, and
we'll keep making them. If
not, I've got two orange
chairs for sale. What's coming
up in today's episode? My
Will Aitken: wife asked me,
Are you sure sales is right
for you? I felt like I was
failing, and I felt like it
wasn't doing good, and I felt
like I couldn't get any
better.
Mark Ackers: Today's guest has
made millions laugh while
teaching people how to sell.
Gone viral on Tiktok. He's co
founded sales feed and built a
LinkedIn following of over
65,000 people. Behind the
skits is someone who nearly
gave up on sales completely.
My guest is will akin did you
used to be crap at sales?
Will Aitken: Yes, I was crap
at sales for a very long time,
far longer than I should have
been during the interview
process, I realised I was
horribly under qualified and
not what they were looking
for. I tried to keep the focus
off me as much as possible. I
basically just recited what I
just learned, which wasn't
necessarily the truth. The
whole job of sales is to make
the company money, and if
you're not doing that, then
you are losing the money
Mark Ackers: 100% good
salesperson shouldn't cost
anything.
Will Aitken: I blamed
everything. And I thought, Oh,
it's my territory. It's my
manager. Ironically, after all
this, after dropping the ego,
my ego made me leave that
company. I knew they were they
had the senior candidate
title, but they were being
paid much more aggressive,
both accelerators and a base
salary, and that made me
bitter and hurt. So I went to
my manager and said, Give me
the promotion. I've earned it.
And he didn't. How
Mark Ackers: have you become
so self aware? Because so many
people aren't 2023. Is
Will Aitken: probably the
worst year of my entire life,
because I didn't believe in
what I was doing. I wasn't
learning anymore need for
approval validation. I wanted
to be the best. That wasn't
about being successful, in my
mind at the time, it was about
trying to look the most
successful. If someone
Mark Ackers: listens to this
has realised that they've got
a need for approval or even a
need to be loved. What's
something they can do to start
to overcome that. Think about
what you do with
Hello and welcome to a new
episode of The I used to be
crap at sales Podcast. I'm
Mark Akers, your host, the co
founder and Head of Sales here
at my sales coach today's
guest, born in Milton Keynes,
armed with what he calls a
pointless degree. He's been a
pub bartender, a recruiter, a
SaaS AE, a content creator,
and now he runs his own sales
business. In their bio, they
say they're a salesperson, a
sales trainer, a keynote
speaker, an author and a piss
taker, fluent in English,
memes and sarcasm. They're the
chief vice directing,
president of managing things.
If you've not guessed it, by
now, I'm really excited for
this episode. My guest is will
Aitken will? Hello and welcome
to the
Will Aitken: podcast. Mark.
What an intro mate. Very happy
to be here. Thank you for
inviting me on. It's
Mark Ackers: good to have you.
Will we start the podcast in
the same way every time, which
is a yes, no question, did you
used to be crap at sales?
Will Aitken: I wouldn't have
agreed to come on a podcast
called I used to be crap at
sales if that wasn't the case.
Yes, I was crap at sales for a
very long time, far longer
than I should
Mark Ackers: have been. When
you think about being crap at
sales. Is there a particular
moment that springs to mind
when you really realise that
to be true?
Will Aitken: Yeah, probably,
when my wife asked me, Are you
sure sales is right for you?
You know, like the person who
knows me the most is you sure
you want to be in sales? You
know, because I was in a place
where I was I felt like I was
failing, and I felt like it
wasn't doing good, and I felt
like I couldn't get any
better. And she asked me that
question. I was like, damn,
but do what am I? Should I? I
I don't know,
Mark Ackers: but I figured
out. So take me to that
moment. Where were you when
she asked you that question?
I'd
Will Aitken: been selling
media sponsors, advertising,
that type of thing, for a
couple of years, and the
journey to that point had been
a lot of highs and a lot of
lows as well. Really
inconsistent, right? So we're,
you know, going from feast to
famine each month, no
consistency whatsoever. And
then when my son was born, I
took some time off, as you
should, as a father to help
out. It's a really tough time,
especially when it's your
first kid, you don't know what
the heck you're doing. And I
came back and I just had
nothing, no pipeline. And
following that, there was just
a few months, just in a row,
just zeros or very low numbers
on the leaderboard. And I was
like, I don't know how to make
this work. And that was, I was
having a lot of self doubt,
right? I'm like, Okay, well, I
obviously don't know what I'm
doing. I've been lucky in the
past. You know, that's kind of
how I felt about my past
performance, and those, those
feast I mentioned the high
months. So when we had that
chat, that was, that was where
I was at
Mark Ackers: when she asked
you, What did you say? Like,
how taken back were you by
that question?
Will Aitken: Obviously, it's
within the context of that
conversation, and I was
complaining about, you know,
things not going well, and
being nervous about making
enough money to support a new
family as well, right? I'd ask
myself that question, to be
honest, I hadn't probably said
out loud, like, you know, you
when you when you have that
self doubt, you're like, maybe
I shouldn't do this. Maybe
it's just go and be something
else. I also thought, what
else am I supposed to do? I
haven't got any skills. I
haven't really got any
passionate desires or interest
to do anything else. There was
nothing really that that was
calling to me, or that a lot
of people go I want to be
this, and then end up finding
that they can't make that and
then end up in sales box, and
I just didn't have anything.
So I just got into sales
because I could, right? I
thought to myself, well, I
don't have anything else. I
kind of have. Be good at this,
because otherwise I won't.
I'll be starting again. And as
I said, I was young family, so
I thought starting all over
again in my career wasn't
really an option that point as
well.
Mark Ackers: It's really
interesting. I imagine so many
people listen to this would
have had that moment where
they think, what else am I
meant to do? It's not going
well, but what else am I meant
to do? I really feel the
similarities. I felt that I
remember there was a point
where I was in sales. I fell
into it. Well, fell into it.
It's probably not quite right.
I went into it because I
wanted to earn more money.
Sounds like you're saying the
same wasn't going so well.
What am I meant to do? I
remember that exact thought, I
wish I just had a skill. And I
was thinking, Could I be an
electrician? Could I be a
plumber? Could I be a
carpenter? I wished I had a
skill. And it feels like at
that point, though, you didn't
realise you had a skill,
because you've got one, and
you've got many, actually, and
but you probably didn't
realise at the time that sales
is a skill, and it feels like
you've got on that journey to
realising not only is it a
skill, it's a fundamental
skill that if you can and
look, Master's a very strong
word, but if you can get good
at it, actually, there's a lot
you can achieve. And it feels
like you've had to go on that
journey to a place where you
are today, which is really
what we want to get to in the
podcast, right? That journey
of how you got into sales,
realising it was crap to where
you are today, because so many
people follow your content,
love your content. I'm one of
those people, and so many
people look up to you, and
they think, Ah, it's easy for
this guy. And I know, you
know, that's just not true.
You've gotten a journey, and
that's we're going to share
today. Let's take it right
back when you were growing up,
you were the odd child. What
do you mean by that? A
Will Aitken: lot of people in
sales often are add a HD, that
type of thing sometimes just
correlates with ending up in
sales in the first place. I
find I was never the worst at
school, like in terms of
academics, but I was
definitely the most in trouble
at the time, you know, acting
out, probably looking for some
kind of attention, if I'm
honest, but then also being
the loudest and doing things
somewhat differently to
everyone else. I was known by
a lot of people, not because I
was their friend, but just
because I got noticed for the
right things and the wrong
things, most of the wrong
things, getting in trouble.
Nothing mean or nasty, just
normally, just being very
mischievous, not following the
Mark Ackers: rules. Obviously,
you talk about not being
academic. You went to
university. You call it a
pointless degree, which is not
saying I'm comfortable with
because I think with degrees,
really, it doesn't matter what
it's in. It's showing that you
can self study, learn, hold
yourself accountable, show up.
You can take a project, you
can break it down, you can you
can provide information in a
way. It's digestible like
that. When I look at degrees,
that's what I'm looking for,
and I put far more weight on
what Mark did they get versus
what was it in? But you call
it pointless. What made you
choose that and has it helped
you at all? Do
Will Aitken: you really want
to know? Absolutely, I wanted
to be an engineer when I was,
like, high school age.
Apologies, I've been in
America for so long I can't
remember sick form. I wanted
to be an engineer. I wanted to
be I had a private pilot's
licence that I got when I was
16, so I was really into
planes. I want to go and do
aerospace engineering at
Liverpool, and my backup was,
like, Swansea or something
like that. But the issue was I
really struggled with math and
physics, and I didn't actually
like them that much. And I
don't think I quite realised
it's not about aeroplanes.
It's about like science and
things that I probably didn't
enjoy as much I wanted to do,
but I had it in my mind. You
pick your A Levels sometimes,
and you kind of feel a bit
stuck in that path at that
point, even if you know you're
not enjoying it or doing well
and you're too young to have
the the self awareness to say,
maybe this isn't what I
actually want to do. I just
said it because it sounded
cool, and I like planes, you
know. So then when my a level
results came back, and I did
have to get some extra
studying and tutoring to even
get to what I got to, but they
were, they're pretty bad
grades. So naturally, the bull
didn't want me to on that
aerospace engineering course.
Swansea gave me an option, a
second option, of doing a
course I wasn't as interested
in. It was called something
like aircraft maintenance
engineering or something like
that. But it was kind of like
it was a trade. You know, it
was more of a trade. It was
like a mix between a degree in
a trade school. And I said,
Well, maybe I don't want to
either of those things, but I
knew I wanted to go to
university. I knew I wanted
the independence, and I had a
bit of pressure for my parents
to do that as well. All my
sisters, my old, two old
sisters, had also gone to
university. And even my dad
said, what you kind of almost
said, it's about not just
going to university and
learning something that you're
going to plan to use about
being independent. It's about
going out there and learning
skills of just learning and
getting better. So then what I
decided, I went through clear
I decided to say, note
Swansea's offer of this second
course I wasn't interested in.
And I went on Google, and I
typed in which university,
because I was 17 years old,
has the best, I shouldn't say
best, the highest girl to boy
ratio. Yeah, 817, year old
boys only have really one
thing on their mind. And I was
thinking, oh, yeah, university
girls. And then I went on a
step further, which course at
the University of the most
girls has the most girls on
it, and that was events
management, because a lot of
people on that course wanted
to be, you know, conference
planners or wedding planners.
That was, like, the thing that
was standing out to them. So a
lot of people wanted to do
that. And I just said, you
know, it's something and it's
it by the coast, and it will
be good fun. So I chose that
and, and that's how. Ended up
at
Mark Ackers: it. I feel like
such an idiot. I picked, I
picked my university based on
what was the furthest away
from home that had a Premier
League football team where I
could get a
Will Aitken: ticket. I'm glad
to know that we've made
decisions based on things that
probably weren't that
important. Yeah, no,
definitely. And how many times
did you get to go see the
footy?
Mark Ackers: Because I
realised back then, you could
get away with buying a child
ticket, and no one checked. So
I was getting tickets for
like, five quid, and walking
up
Will Aitken: to you because I
didn't manage to get pull any
girls, I won't lie. So my plan
didn't work out quite the way
it went. I wanted to
Mark Ackers: Fair enough. So
okay, so that's really
interesting. I've got a little
bit of insight here from you
in school, in university, and
from there, it feels like you
couldn't do what you wanted to
do. You've got this degree,
not really wanting to use it.
And it's it feels like you had
then a bit of time to
yourself, where you worked.
Well, it says on LinkedIn, you
worked in
Will Aitken: a pub. I worked
at that pub while I was at
university. So after I
graduated, I was sat there
thinking, I get a job. And I
did get a job. I went and
worked. I don't know if this
is still on my LinkedIn,
because it was a short stint.
But I worked for Connells, the
estate agent, a call centre of
people who basically would
call anyone else who had their
home listed with, I know,
tailors or wimpies or whoever
it may be, and try and get
them to switch estate agents.
So for three months, I was
just banging the phones on
that. I enjoyed it, and I was
okay at it as well, but it
was, it's, you know, that
classic, very high volume
cold, cooling environment. I
think that's good for people
as well, in an office in lane
buzzard. And then while I was
doing that, I was like, I'm
still young. I still want to
travel. So I went and then did
a ski season in France where I
managed a bar in a hotel and
skied and did the class thing
there. And then I came back
from that the bar that I was
managing. That hotel, like
most, like shallow people,
it's kind of weird. I had a
quota as the bar, so I had to
try and get as many people to
buy from that bar as possible
every single week. So I'd be
throwing pub quizzes, just
doing anything to get people
to go from dinner, where they
got free wine, to come and
spend money in the bar. And I
was actually really good at
that as well. Pub quizzes
would always go down. Well, it
was a chance for me to get to
know everyone in the room,
because every room, because
every week we'd have a new
round of guests staying in the
hotel. And after that, they
paid out a big bonus, because
I absolutely smashed the bar
target and and I used that
money to then go backpacking.
That's where I went across
Asia, did all that stuff, and
landed in Australia, which is
where I had met my partner and
got probably my first real big
boy job, which was when I got
into recruitment.
Mark Ackers: Wow. So first of
all, I'm starting to see where
some of this event management
degree did get used.
Organising pub quizzes is
definitely an event. Play it
down, if you like. But what,
what I think you're you are
doing, though, is you're
learning the fundamental
skills of sales when it comes
to communication with
different types of people.
You'd have met different
people at university,
different people in the pub,
different people at the ski
lawn, learn ski lodge, then
you've gone travelling, and
one of the key things that
sales people can do is adapt
to whoever they're speaking i
In your case, whoever you're
serving. And you'd have been
learning without even
realising it, how you need to
adjust the way in which you
communicate with different
people, which is such a
difficult thing to do. And
you've been at a call centre
in a pub as a university,
you've been travelling, so
you're learning the
fundamentals here. That's
going to set you up for a
strong career. You're right. I
saw you went travelling, went
to Sydney, and obviously, for
reasons, everybody understands
LinkedIn is not 100 accurate.
I've got your first job as
search it local in Sydney. You
mentioned advertising earlier.
You only left two months. I
didn't know that was part of
like work placement on there,
Will Aitken: because from
there, it's all honest. I
think the Connors thing wasn't
really worth putting on there,
because then it would have
been a break as well. But the
Yeah, I got a call centre. And
that was actually where I did,
I did meet my my wife. She was
sat next to me. And that was
if, if I made Connells sound
like a bit of a boil over
environment, that was insane,
like, at least Connells had a
click to dial, you know, this
was like, tapping on the
phone, yellow pages, you know,
this was in, like, 2015 2016,
yeah, and I was just tapping
away, and yeah, the cold hard
target was 300 and the
service, we didn't realise it
at first, because they did a
very good job making sure no
one knew this, like it was
helping people set up a free
page that they could do for
themselves on Google, and then
charging them subscription
price for it. So the product
was kind of scammy as well. So
you just had to just make as
many dollars until you get
someone who was willing to
stay on the phone with you,
and then they would be like,
stood behind you, like, don't
let them go. Don't let them
go. Don't let them hang up.
Because if they hung up,
they'd go online and they
would Google the company see
all these negative reviews. So
you can do this stuff for
free. You can do it yourself.
We can get someone pay someone
like on Fiverr to do it for
you, and they would never, we
would never be able to get
them. So it was either like,
close them on that first call,
or you would never talk to
them again. And that was
really high pressure. And I
remember I was pretty good at
that, but also, like those
kind of I don't want to call a
scam, because they did
actually provide a service of
sorts, but like that naturally
attracts some very intense
people who were okay of all
that, and the environment was
just very toxic sales
environment, right? So one day
a. I was sat next to my wife,
and I said, you want to go get
some she wasn't even, I wasn't
even date her. At that point,
I went. I was like to go grab
some lunch. And she said,
Sure, I don't think I love
working here. She I'd made a
few sales, she'd made none.
And then I was like, Hey,
would you like to go have
dinner? And then we actually
made it start a real
relationship. But once we left
that, I was like, Okay, now I
need a real job, because I
don't want to do that. And we
left on the same day. We just
quit. And we just quit, and we
actually moved in together
very soon after that, very
fast. The reason I even
started working at Connells in
the first place, the reason I
got a sales job the moment in
Australia, was because
everyone always said, you'd be
great at sales. Will you'd be
great at sales and or you'd be
great, you'd be great at
recruitment. Because I find
recruitment, a lot of sellers
who work in tech don't realise
this, I don't think, but it's
very sales adjacent. If you're
working in an agency, you are
going to have to cold call and
fire clients. If you do not
have a process, you will not
place candidates. Is very
quota based as well. So I
started working as a recruiter
at that point, and that was
actually a real job and great
company. And I had an amazing
boss there. God, I remember
him the way he he really
invested in me and his team.
Mark Ackers: So yes, I saw
you. You move from there to
recruitment. And the line that
you used was you were reading
a Reddit article, and it said
you could make bank moving
into recruitment, which made
me laugh. I've not heard that
phrase before, but obviously
you can depict what it means.
But you moved to recruitment,
and you said you were top
performer there. How long
before you become a top
performer? From joining to
become a top performer? How
did that
Will Aitken: take you? So they
had a grad scheme, and I don't
think, I think a lot of people
don't realise this, but
sometimes companies will hire
five people with the not full
knowledge that three of them
will not make it. So they
hired a grad scheme of people
who were like, had the right
attributes, have had no
experience in their field,
with the idea of training them
up because they were trying to
grow as an agency. And how
firing and finding good
recruiters is just as tough as
finding a good salesperson,
oftentimes a good recruiter
will be making enough and be
happy enough that they won't
want to leave a lot of the
time. So they thought that was
a better strategy. And in that
grad group, it was just like
nine day between me and the
other people who joined. I
just showed up, I guess. But
also, I think the biggest
difference actually, was
probably the fact that I was
willing to cold call, because
I just come from what I just
described, like, it didn't
like, I could get clients, and
if I had enough clients, I
could, it meant more
placements, basically, you
know, whereas they were all
struggling to try and fill
these jobs that that they'd
been given, but the ones they
were being given weren't the
best jobs, you know. I mean,
so like, they, they would be
working with another recruiter
in the office who'd be like, I
need you to help me find some
candidates for this role, but
I'd be going out and making
calls to start finding new
roles where there'd be more
urgency and there would
actually be, it'd be a
placeable position, basically.
And while I was doing that as
well, I mean, I was focusing
on hiring salespeople, a lot
of them in the SaaS industry
as well. And that's where I
started. My first exposure to
software, which is which
informed my direction, going
Mark Ackers: there as well,
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And it's interesting, because
you're right. You see
recruiters get exposed to
these jobs all the time, and
they think I could do that
job. But I suppose, just
before we get to that move to
I'm guessing it's hr.com you
went to next when you're with
the other grads. I get it.
You, you've you've made cold
calls before, you've been in
boiler rooms, etc. Equally,
I've seen this happen far too
many times. You hire someone
knowing they know how to cold
call. They've done it before,
they've been that boiler room,
but they get in with a group
of other people that don't do
it, so they just stop. They
just follow the norm and the
pack. And that's really easy
to do. What made you not
follow the pack and think I'm
gonna go outbound here, I'm
gonna go and win new
customers. I appreciate it
might seem obvious now, well,
make money, makes up, but it's
really hard to do that. That's
Will Aitken: a really good
question, actually, because
you're right. It would have
been easy to not do it. I
think I'm really competitive.
A lot of I know I said I'm did
it to make bank, but a lot of
the things that actually
fulfil me. Working in sales is
sometimes just being the best,
not necessarily the best trait
to have, because if you're
constantly comparing yourself
to someone else or measuring
your success against other
people, that's not really a
route to fulfilment. I don't
find but I wanted to be the
best I and I saw that as my
competitive advantage. Have
you always felt that way?
Yeah, I've got. I grew up in a
family of with two older
sisters, we're still competing
today. And even when I started
making really, really good
money selling software, I was
like, I didn't necessarily
need the money, you know? I
mean, like, I didn't have a
plan for it. And even when I
had it, I didn't know what to
do with it, it was still, man,
this feels good. Just feeling
accomplished and being a top
performer. That was almost
like a big, big thing that
kept me going. It was like,
that was it. But the opposite
side of that is that when
things aren't going well and
you value that type of thing,
you can end up in this
opposite end of the spectrum
where you feel self doubt
because you're not doing as
well against other people, or
you're you're underperforming,
and you're not feeling like
you're a winner, you know? I
mean,
Mark Ackers: yeah, attaching
your self worth to your
performance. Went to work. I
think I see a lot of people do
that, and I've been quite
vocal that I've struggled with
that, you know, periods of my
life where you not had the
quarter a month that you want,
and you take it home with you,
and you've shared before we
got on a couple of points in
your career that we're going
to get to just before we do
that. As I say, it feels like
you're an upward trajectory
here. You've got a new job,
you're in recruitment, you're
a top performer. How long did
that take you, though, to get
to the point where you knew
people were tapping your
shoulder at this recruitment
company saying, Will you're
one of the best you could see
you're one of the best. How
long did that actually
Will Aitken: take you when I
was the last grad left, and I
was I was making more
placements than people in
doing it for years, and here's
the thing as well. Like, I
didn't necessarily do it, by
the way. I was told I had a
team lead there. So the
managing director of this firm
was the guy who sit me down.
He felt like therapy would do,
like coaching one on one
sessions. He would recommend
books you should go and read.
It was really helpful stuff.
But I was at a team lead
British guy. Every recruiting
in Australia feels like a
Brit, you know, just seems to
be the thing that everyone
does when they move there, as
a pom, as the Australians like
to call us. And he said, Man,
you never do what I want you
to do. It's like you feel
there's more glory in doing it
your way than just doing it
the the easy or best or most
effective way. Like I'm
building you a bridge, and I'm
telling you, just walk across
it and you're going down the
road, down the stream, jumping
on a rope swing to swing
across so you can go wee Look
at me, and then jumping onto
the other side. That was the
analogy using it that stuck me
for so long. And he was like,
I'm trying to help you, man,
and you keep doing things your
own way, and it works, but you
could be so much better if you
had a process, if you listen
to these things I'm trying to
help you with. I also felt
there's a sense of
responsibility that I think a
lot of people miss when they
go and work for a company, and
it's not something that you
should prioritise over your
own career, your own things.
But I felt, when you're
getting paid a base salary,
you know, you're now costing
that company money, right? And
it wasn't a huge company, it
was probably, I think, office
at the time, of 25 people,
right? And it was privately
owned, so I knew, and I knew
the guy owned it, right? So
there's a sense of
responsibility. I felt that I
had to do make sure that I was
a profitable person to keep
around, right? And that was,
at the start, one of my main
focuses. So although they
wanted to focus on hiring for
tech roles, and that was,
like, their big focus, I
remember the first role I
placed, I just cold called
this company and said, Hey, I
saw you hiring a junior
accountant. I've got someone.
And then I played and they're
like, Well, we're a tech
recruitment agency. Why are
you placing accountants? Is
like, because I wanted to make
a placement, you know. And I
thought any, any placement, is
a good placement. Is a good
placement, and that person
worked out, didn't, they
didn't leave, or anything like
that. And then it became more
focused on the sales side of
things, because
Mark Ackers: that was, that
was interesting to me. It's
fascinating, like, in the
sense of, you've gone out of
the swim lane to make a
placement, to have that
success. The bit that really
interested me, though, was the
way in which you were so aware
of your salary cost the
business needing to repay
that. Do you think most sales
people think
Will Aitken: like that? I
haven't asked, I don't know
content. What do you think I'm
contemplating me too.
Mark Ackers: I tell you why. I
don't know if they do because,
and I know anyone listening to
this will take this in the way
it's intended, to be in sales
and to be good. And people
listening to this podcast are
good at sales because they're
listening to podcasts. They're
trying to get better doing the
work. Exactly they're doing
that. They're doing the work.
We've all got some level of
ego, right? And being aware of
it, it's important. But we've
all got some level of ego.
We've had a level of success.
I think most people see their
base salary is that's why I
get paid, because of how good
I am not. I'm in debt to this
business, and I better repay
that. I don't know. It's an
interesting one that, like you
say, I've never really asked
Will Aitken: people that,
yeah, and I've never really
spoken about it. I don't think
I've ever said this
definitely, definitely on a
podcast. But it's also like,
if you're objective about it,
the whole job of sales is to
make the company money, and if
you're not doing that, then
you are losing the money 100%
good salesperson shouldn't
cost anything. Yeah, exactly.
It should be a no brainer,
yeah, that to pay them a base
and the other commission
they're earning as well. But I
think it's harder when you get
people who
Mark Ackers: don't, oh, 100%
like because they are, they
just a cost on a, on a on the
spreadsheet, you know, and
they're not bringing in and
obviously, it's not just about
covering their cost. It's
multiple
Will Aitken: times that it's,
it's a similar, I don't know
if it's, I don't know if this
is rather just the
conversation. As you can
probably tell Mark, Canadians
don't know this because they
don't know the different
lingual areas in the UK. But
I'm pretty posh. You can
probably you would you
consider me posh sounding
Mark Ackers: when you can't
really detect where someone's
from? Yes, yes.
Will Aitken: Okay, so I went
to boarding school my father
sent me to. I think it's like
the eighth most expensive one
of the country, but it's also
the one that's like, also the
one that's like, all the wrong
goods go. It's not stove, but
it's near that, you know. And
almost my entire life, I felt
guilt for the fact that my dad
sent me to school, really
expensive school, and I went
to, like, the 78th top
university in the entire
country, University of brown.
At least it said, University
of of no shame in Polytechnic.
But at least they had that
right. I was that was my
justification, and I felt
guilty they had spent this
money on me. I'd actually been
the least successful of my my
siblings at that point. My
sister went to Loughborough.
My sister went to, I want to
say she went to University of
Swansea, actually, but I felt
this guilt, and I felt like
that was for a long time until
I got some therapy and.
Realise that this isn't how
you should be thinking about
things. I felt like I had to
be successful to make it, to
make him feel okay about
spending that now I've now had
much more mature conversations
my dad where he's like, Oh,
well, I wanted for you to be
happy, man. You don't owe me
anything. I did that because I
love my kids, you know. And
that's a great conversation to
have, right? In my mind, I had
to be successful. And I think
it's very similar almost to
the fact that when a company
pays you a salary, I feel like
I have to, I owe it to them to
make sure that I am
profitable. And then some on
top of that, you know, I mean
that I think the two mindsets
are in a similar place. Now, a
couple of years back, my dad
was like, will you make twice
as much as me? And I'm like,
holy crap, you're the most
successful person I've ever
known, or in my mind, he
always was. Then I realised
that's not even just it, it's
not just that, it's not just
that's not all success and
happiness, right? That's just
a side tangent of I was
thinking about it when you
asked me that question. That's
like, similar to
Mark Ackers: that. I think a
lot of people can relate to
that. You know, this feeling
indebted to someone that's
given you a great opportunity
and and part of me wondered if
the fact that you knew the
owner of the business that you
were talking about made you
feel a slightly different way.
I think a lot of people will
relate to that. And it's it
comes down to that need for
approval. And that affects so
many salespeople. And, you
know, I appreciate people
listening to this won't see
the facial expression you just
pulled, but you kind of pull
that face where you almost
saying, now that
Will Aitken: Yeah, and this is
something that that I still
work on today. It's need for
approval, validation. And you
can almost hear it when I say,
I say I was the thing I
enjoyed about being a top
salesperson wasn't helping my
clients. It wasn't making
tonnes of money because I
didn't need the money because
we bought a house at a good
time, and our payments aren't
that high, you know, like we
weren't ever struggling. It
was winning, being the best.
And then even now, when you
look at what I do for my work,
there is a lot of that they've
you, if you, if you prioritise
that over anything else, you
can become dependent on
LinkedIn likes and engagement,
you know, I mean, and I've had
to, I've had to rein that in.
I've, I've actually spoken to
professionals about that very
topic. That's why, yeah, need
for approval, chasing
validation, versus just
there's this thing of, do you
want to look successful, or do
you want to be successful? And
being successful is a much
more fulfilling and happy and
whole place to be than trying
to look successful. And when I
say I wanted to be the best,
that wasn't about being
successful, in my mind at the
time, it was about trying to
look the most successful.
Mark Ackers: This is one of
the greatest challenges that
salespeople have, is a need
for approval, and it ties back
in. There's so many threads
that we could tie this back to
right, feeling like you don't
have a skill, feeling like
you've got to earn money to
repay, feeling like you've got
to be the best, feeling like
you've got to go out and win
new customers and and validate
the reasons for being hired
and being better than
everybody else. It all comes
back down to need for
approval. The impact this has,
though, in sales
conversations, and I want to
be really clear, everybody in
the world has got a degree of
need for approval, a degree.
There's a company in Boston
called objective management
group, and they assess
salespeople. They've got the
world's most sophisticated
sales assessment. It's
research proven, it's
scientific, it's validated,
all all those buzzwords, but
it's it's a phenomenal
assessment, and when you
complete it, it benchmarks you
against 2.5 million sales
people and counting. I've
taken one. Everyone in my team
has taken one. We provide them
at my sales coach, not an
intended plug, but since we're
here, the thing that's really
interesting is the need for
approval is the thing. And I
won't be able to do the stats
justice, but I'll be able to
relay them enough that the
point is made that need for
approval is the biggest thing
that separates elite
salespeople to weak
salespeople. And when I say
elite, they found, bear in
mind, 2.5 million people. They
found that only 6% salespeople
are elite, which is, which is
such a small number, but when
they look into the biggest
differences, and this is the
bit, I won't know the exact
maps and percentages, but need
for approval was the biggest
thing that they found that the
elite didn't have it. Okay,
that was my question. The
Elite didn't have it. Because
when you've got a need for
approval, the weaker you are
in sales, the more it becomes
a need to be loved, right?
Need for approval means you
don't want to upset the person
you're speaking to, and when
you don't want to upset them,
it's because you're worried
about what they might say or
feel to what you're about to
say. What that stops you from
doing is asking the tough
questions that get to the
truth really going beyond
surface level pain, and when
you've got that need for
approval, you fear asking
those questions because you're
connected to the outcome, you
don't want to upset them. You
want to be loved, you want to
be liked, you want to be seen
as helpful and successful. You
want to be a servant. You
don't want to be a
consultative seller. And I
think everybody's had a moment
in their career where they
realise I'm just doing what
I'm told. This prospect is
pushing me around. They're
bullying me. They're, they're,
they're getting what they
want. And, you know, I've got
loads of stories, yeah,
exactly, being used, you know?
And it's fascinating. That you
seem to be so in tune that
you've had this need for
approval. I love that you've
openly spoken a couple of
times already just about
having therapy and, you know,
speaking to someone that can
help you work through what is
head trash, but is put in
there to everybody as part of
the way we grow up. So need
for approval is a fascinating
topic, and we're not going too
deep. Everybody listening to
this podcast, it's had that
realisation, or they will go
on to have it as a result.
Listen to this where they've
not asked the prospect the
right questions because
they've been worried about
what they might say and how
they might feel. And the
reality is, when you don't ask
the right questions, you don't
get to the truth, and when you
don't get to the truth, you
can't help
Will Aitken: so Chase lies a
pipeline full of lies,
Mark Ackers: well, lies and
hope and that doesn't sell.
And I would say, Well, let me
ask you, if someone listens to
this has realised that they've
got a need for approval or
even a need to be loved,
what's something they can do
to start to overcome that
sounds like you've you've
gotten a bit of a journey.
Will Aitken: Think about what
you do when no one's watching,
and lose the ego just for a
minute and realise that you
need to focus on what you know
about yourself versus what
other people might think or
know about you. Most people,
when they look inwards, aren't
happy sometimes with what they
truly have been bringing to
the table, what they would
bring to the table if no one
was going to pat them on the
back, if no one was going to
say they liked them or they
did a good job, what would you
do? Then that's what you need
to think about, versus these
approvals that don't really
mean anything. It's a much
more deep topic than that, I
think, but it needs to come
from what would you be without
approval? And are you building
the skill set and the mindset
that would make you proud of
yourself versus anyone else
proud or happy with you or
like,
Mark Ackers: how old you will
you don't mind me asking, I'm
3030, so yeah, you're you're
seven years younger than me.
So this will relate even more
to you, but with the rise that
you have seen, as I say, you'd
have been younger when you got
exposed to it. But the rise of
social media, I feel like the
need for approval rocketed. Oh
my gosh, because everything is
about instant gratification.
Everything is about likes,
shares. This is where I'm
going to stand a little bit on
retweets or hearts, whatever
it is in platforms, right? But
it's that instant
gratification and that need
for approval like you want to,
you want to share what you do,
but if you're in a career of
sales, having that need for
approval is going to really
harm your career and the
trajectory of it. And I think
just even becoming self aware
is the starting point. What a
great segment. Let's start to
move on. Obviously, we're
going to end up to where you
are today will, which is
obviously in a phenomenal
place, but we're not quite
done yet with your with your
journey, because you shared
with me, and I wouldn't have
known this, and I love that
you shared this in advance.
When you were@hr.com you said
you felt like you were
constantly worried about
getting fired. And again,
every salesperson has had that
feeling, right, like they've
had bad cause, bad months, but
you seem to Yo Yo, 230% one
quarter, 11% another quarter.
What was going on?
Will Aitken: Yeah. So after I
finished up that recruitment
agency in Australia, and this
was also like, I felt a lot of
guilt for because they were
sponsoring me to stay in
Australia. So that means they
were spending money and going
for effort to make sure I
could remain now when, when
you're under a certain type of
visa there, you wouldn't be
able to work at a job for more
than six months. And at the
time, I knew that if I told
them I was planning to leave
within the next couple of
years, they would never keep
me employed, because
recruitment sales, it's a
longer pipeline than you know
that normally. And I felt like
if I told them the truth about
that, then they would not want
to keep me around, even if I
was doing well. But I always
my wife, uh, is from Canada,
and she when we met, and I
started doing all this, she
was actually she'd gone
travelling by herself, and she
had left her degree half
finished, so she knew she
wanted to go back and finish.
So we stayed for longer than
we planned to, and I carried
on working at the recruitment
agency. But I had this. I
always knew I was going to
move to North America to help
her with finishing her studies
and go there. And this is
where I was thinking, Okay,
well, from what I know, I'd
really like to get into
software sales, because I've
been hiring these people. I've
been recruiting them. I'd
known about the OTs and I'd
seen Whoa. I mean, recruitment
is great money as well. But
like, I was also thinking, the
part I enjoy a lot about this
isn't working with flaky
candidates. It's also it's
working for clients. It's
talking to them. As I said,
the thing that made me
different in the office was my
ability to cold call and
willingness to do it. So I
thought, if I could get paid
more to just do the selling
part of it, instead of trying
to manage a pipeline for the
candidates as well. That's a
great outcome, right? And it
was quite funny, because when
I, when I finally told them,
they're like, Why didn't you
tell us sooner? That
recruitment agency, they, man,
we would have, we would have
helped you. We've got you on
stuff that you could have
worked close quicker. And
then, man, they've really
helped me out as well. They
gave me a huge bonus when I
left and they said, You they
said, You didn't stop trying
until the day, until your very
last day, like you were always
there. They took me out for
dinner. I'm like, Guys, I've
lied to you and betrayed you,
and I'm leaving you guys,
like, why are you being so
nice? And they're like, Could
you show it up? And I was
like, That felt really, really
nice. So I still talk to the
Managing Director, my team
lead from that company.
Because, you know, a lot of
people would have been, wow,
he lied to us. Get me. Out,
but they just wish me my best
on my move to North America,
and off I went. So then when I
landed North America, my wife
is from a small province
called Prince Edward Island,
where there are about 50,000
people who live there and a
university. And believe it or
not, there's not many tech
companies there. So my goal of
getting into tech wasn't as
realistic it could be.
However, there was a company
that sold to tech companies,
and they were selling media
sponsorships, email campaigns.
They were like this big media
company, essentially for HR
people. So a lot of the
sponsorships you were selling
into were companies like
CareerBuilder, the job ad
sites, indeed, LinkedIn. You
know anyone who has a HR
audience, we were selling
into. So it was close enough,
and I needed a job that it was
along along the way of where I
wanted to get to. It was B to
B. It was somewhat
consultative selling. So
that's where I ended up there.
But it wasn't all sunshine and
rainbows from where I just
come off feeling like I was
top of the world. Even when I
left, they still loved me.
That company was a little bit
different how so I was working
fully remotely, and this was
before 2020 when that wasn't
really the norm, and I wasn't
prepared to. I have focus
issues, be it ADHD or just
avoidance. So when I was in a
room by myself, in my office,
all that cold calling, I told
you I love doing harder to do
when I only had myself to keep
myself accountable, and there
was detachment from all these
people I worked with and knew
it was really, really tough.
So I'd go through these big,
big pushes of motivation, and
then I'd slack off, you know,
and not work as hard as I
should have done. I also, oh
God, the things I was doing,
the skills that I had at that
point, you know, I've read
your book practical
prospecting. Is it problem?
Prospecting? Sorry, I
apologise, you know, my the
messages, the emails that, and
I wasn't really making any
calls, honestly, they were
bad, you know. And so I was
just kind of brute forcing it
by sheer volume. When I had
the motivation, which was rare
or inconsistent. Should I say?
I had a sales leader who very
quickly left after I joined
after she hired me, and then
we replaced him with another
sales leader. But that sales
leader wasn't really the type
to get involved. He just said,
Oh, cool. Keep doing what
you're doing. You know. Just
didn't really have to talk to
me. You'd cancel out one on
one every week pretty much.
And then when we get on we'd
be like, how you doing, mate?
Yeah, good you. Yeah, good
bye. That was it, you know,
got any big deals? Yeah,
that's that, you know, there
was no All right, what are you
struggling with? What do you
want to work on? Because I was
having these big ups and
downs. I was sometimes being
celebrated, but then most time
not or, like, it wasn't even
that much celebration as a
team, because we know no one
knew each other. We were
remote. We used to go to
conferences. Sometimes that
was nice. And I got to walk
the floor and basically try
and sell a bunch of trade show
sponsors. If you've ever been
to a trade show, you know,
there's these people walking
the show. Walking the show
show floor, trying to sell it,
you know that then they're not
there as attendees. They're
just that. So I was, I think
it's called briefcasing. I was
just doing that a lot, and
that was quite good fun, to be
honest. That's probably where
I got the most of my success.
Because you're at an event,
you're there, you got paid to
fly out there, you're going
to, you know, work. You know,
I started making a lot of
excuses for I wasn't doing
well. Rather than being
accountable for the fact that
I wasn't really trying by
showing up in any meaningful
Mark Ackers: way. You shared
that as well. You said you
blamed everything, like your
manager, the territory, the
product, but you didn't blame
yourself at that point. What
is interesting is that there
are, and you can be like a
degree of one of these, but
I've just found there's two
types of people, when you work
with them, if you think about
your finger and your thumb,
when something goes wrong,
goes wrong, you either point
with your thumb inwards, or
you point with your finger
outwards. Sounds like
initially you were pointing
your finger outwards. Oh, big
time. It's my manager. It's my
territory. It's the product.
But then it sounds like you
transition where you point
inwards and tell me that's not
easy for people to do. How did
you go from taking no to
responsibility, no
responsibility to full
responsibility. I'm
Will Aitken: not sure there
was a moment that I can
pinpoint. I just knew that I
hadn't been showing up, and it
was almost like I wanted a
fresh start. You know, I said
I had me showing up here, and
that almost made me go almost
embarrassed I hadn't been
showing up, and I knew I
hadn't been. The thing is, I
was going, okay, my territory
sucks. The CEO's daughter, has
the best territory. No wonder
she's the best rep. She was
really, actually very good at
selling, like, very good. When
I was on a call, I wasn't,
like, writing down what she
was doing. She was doing,
like, deep discovery on media,
which is quite transactional
product. She was really
finding people's problems. She
was disqualifying. She was
challenging people's opinions.
You know, I'd just be like,
Oh, all right, here's a deck.
This is what we offer. Product
one, product two, product
three. These the results we
drive. Would you like to buy?
Sometimes not even ask that
quite let's be probably most
time I would even ask that.
You know, I wasn't thinking
about like, Okay, what am I
showing up with? It was
probably very soon after that
conversation my wife, yeah,
because my son was born in
April of 2020, I went back to
work in in late May. It was,
though, during those months
where I was having some bad
performance, I then just said,
I need to, I need to, I need
to change, and I don't want to
give up on sales just yet. And
I think I'd been reading
about, I knew, I read that it
was possible, and maybe even
the things in my head like,
Oh, it's my territory. It's my
my manager, it's my manager.
Did leave very soon after I
came back from parental leave,
my managers, my territory. I
was like, Oh, I was good to a
new company, but better
product, a better manager and
a better product, a better
manager and a better
territory, you know? I mean,
that was probably my
motivation to that point. I
didn't recognise now I look
back at that company, I'm
like, I could have made bank
if I hadn't known them. What I
know now, that comp plan was
ripe for the abusing like
insane. Money could have been
made there, but at the time, I
didn't, I wasn't honest with
myself about that. I just
assumed they're the problem.
So I'm going to change. And to
get that change, I had to find
a new company.
Mark Ackers: So you said,
again, you're very helpful. In
terms of a few notes
beforehand, you said this was
the point in your career where
you allowed yourself to be
coached. And you actually used
the word finally. I finally
allowed myself to be coached.
Tell me more about that moment
and what changed I was at this
company. I blamed
Will Aitken: everything, and I
thought that was that was
probably the reason why I left
that company. I didn't have
the realisation. Company. I
didn't have the realisation
while I was working there that
I was the problem, yeah, but
then I applied to a new
company, and during that sale,
during the interview process,
I realised I was horribly
under qualified and not what
they were looking for. So
during the first interview
with the manager there, I
tried to keep the focus off me
as much as possible. And this
is actually kind of a tip I've
learned since that's actually
a really good way to run an
interview. I was just asking
just asking him questions
about the role, why the role
was available, what he was
hoping that someone would
achieve in the role, like what
the rest of the team looked
like. And inadvertently, I was
actually doing discovery, but
I don't think I realised it.
And I also said to him, hey,
you know, you mentioned you
got this team and you're
really happy with a team
you've done speak transition
recently, like, what's some
things that the team are
doing, and what resources they
looking at, because I'd love
to see if there's any that I'm
not yet looking at. And he
said, there's two things we
love here that really, really
worked well for us. One is gap
selling, and the second one is
the sound of the sales system,
neither of which I'd even
heard of at the time. And he
said, I'd love to take you to
another interview. You seem
like an interesting dude.
Sounds like you're you know
this, this is aligned with
somewhat of your experience. I
was a little bit worried when
I saw that you were selling
media. I was worried you
weren't being going to be very
consulted, but you're asking a
lot of questions, which is
good, give me hope. And I was
like, Okay, I've kind of faked
my way through this. So then
you told me those two things.
So the first thing I did was I
went and bought gap selling
auto, order your book, and I
booked a second interview of
the other hiring manager in
that case, who would actually
end up being my manager. And
it was a week later, so I took
a sound the sales system.
Course, I paid for it myself
and listened to gap something
like three or four times.
Keenan is an intense guy. I'm
now writing a book with him
myself. He is shouting, but it
really resonated with me. It
all kind of, it was almost
like clocking out because I
was still working in several
companies like, I've not been
doing any of this question
thing, not really been
understanding anyone's
situation before they even get
like, before I start showing
my product, like, I this was
like, a light bulb moment, and
I was hearing this like, Oh my
God, there is so much I could
have already been doing
better. Why did I not listen
to this and go and look out
for this stuff two years ago,
I would have had a great time
and you, but like, it was
actually really exciting to be
learning, right? So then by
the time the second interview
came around, I'd like gotten
consumers resources, so I kind
of knew what they wanted to
hear. So I was so this guy was
like, Can you walk me through
your sales process? And I gave
him like the classic, yeah. So
I go early on, and I basically
just recited what I just
learned, which wasn't
necessarily the truth about
how I actually was running my
sales process at the time like
I told you. I was showing up,
putting a deck up, and just
taking them with it and hoping
they'd buy. So I told him
instead that I was doing a
much more consultative
solution style sale, but
because I had all this new
information in my brain, I was
just kind of telling him what
I just learned, but I thought
it was okay, because I said to
myself, Okay, now I know that
I there's all this new stuff
that I haven't even focused I
will. I'm okay with bending
the truth a little bit. Let's
get this opportunity, because
I know I'll make up for it,
and I will show up if I get
it. And this is the point, I
think, where ego almost
completely dissolved. I
suddenly realised I know
nothing, and if I want to be
successful, I'm going to have
to try and work and get
coached and learn more from
places like what I'd already
learned, gap, selling and
timer, get my manager to help
me. So I was like, Okay, I'm
gonna, I'm gonna probably have
to, like, to get this job. And
I did get the job in the end,
but once I'm in there, I will
not make failure an option. It
can't be. I would do. I would
take every piece of coaching.
I will commit my heart to
learning this, because at this
point, I have to make it work.
And sure enough, then we got
in, and the two managers I
worked with at the time, and
I'll give them full credit,
Daniel Herbert and Scott
tower, were incredibly
involved. We were doing two a
week call reviews. We were
doing team tape reviews. We
were doing training sessions,
both as a team and one on one.
I'd never had anyone listen to
my calls before. At first, I
was like, oh, that sounds
scary. I'm gonna have someone.
Scary. I'm gonna have someone
listen to my recordings. I'm
terrified of that. Like, now,
now they're gonna know I'm
full of shit. But I then I
realised, oh no, hang on. Will
stop caring what they think
and just look at what they're
saying. So you can use that
stuff to get better. And it
really worked. Like I would
say, even my willingness to
listen to my own calls, that
was probably the biggest thing
that improved my ability to
sell and the work on specific
parts. And I then had a sales
process as well that I stuck
to. And then once I started
doing well, I had this
confidence, not because I was
like, being the best and doing
really well. It's like I
suddenly felt competent all of
a sudden. And for context, the
company I was working at the
time, they had never had a
sales rep hit quota, because
it was a monthly quota, not
once, certainly not 345,
months in a row. And I was
just like, it was, it was
almost easy, you know, and if
they were really great, not
only because I was winning,
but once I was winning, I
stopped caring about that as
well that piece, even though
I'd always been focused on in
the past, and I got better at
disqualifying and asking those
really tough questions, and
although I hadn't read the
book at the time, essentially
challenging my customers on
like that, because also found
that that company, the company
I was working for, still
didn't have a great product.
There was a lot of deals
where, if I had have gone
product first, I would never
have won, because we were
inferior to the biggest
competitor. We were, like the
third or fourth best in that
space, I would say we weren't
a widely adopted solution. The
other competitor had the same
price point on us, and then a
lot more functionality and
integration. And all that type
of stuff. So the only thing I
could control, though, was the
way I showed up and sold and I
found that would still made it
possible to do some serious
numbers
Mark Ackers: there. Hey, sales
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the description. There's loads
to unpack there, but I'm
smiling because I feel like
this is, this is the turning
point, right? And if I break
down what I'm hearing and what
I believe all ties together.
You go for this interview. You
meet some people, impress you.
They name a couple of books.
One bit of advice I'd give to
anybody listening to this
podcast, and this has always
served me well, is every
manager I've ever had has had
a book, a book that they've
read, a book that they've
loved, and whether they want
to admit it or not, maybe they
don't even realise it. It deep
down, kind of dictates how
they feel about sales and
their philosophy. And I can, I
can rattle off some of those
books, right? So one of my
first bosses, her book was
Jeffrey Kitman, the sales
Bible. I remember she gave it
to me, and I took this shitty
old book to two new zero on
holiday with my girlfriend,
and I remember her looking at
me like, What are you reading?
I remember someone at the pool
laughed at me because it was
called the sales Bible. But I
was like, no, no, this. If
this book's important to her,
I need to read it. Soon as I
read it, I understood her a
whole lot better. I then had a
different boss, and it was the
lean startup. I read this book
I didn't enjoy at all, but
understood him a whole lot
more. And then it was
fanatical prospecting. Then it
was, I think it was the
challenges out, right? And and
then it was no what was the
predictable revenue, right?
All these books I'm getting
the time I say wrong, but
every manager I've had has had
a book. If you can find what
that book is and read it, you
understand them a whole lot
better. And you've gone away.
And this is the interesting
bit. You've read gap selling.
I listened to it. I won't lie,
yeah, no, no, don't worry.
It's absolutely fine. You've
Will Aitken: listened so some
people will fight you on that
one over accounts, but I
listened to it like a few
times on two work speed, one
at one beat. Speed took notes
the second time through. You
know? So
Mark Ackers: it's interesting.
I think, look, this comes down
to everyone's got their own
learning styles. I think some
books are totally acceptable
as audio books. There are some
books that I feel like you
need to read because, because
they're really tactical, but
that that's me. Do you remain
like I
Will Aitken: enjoyed reading
your book? I don't think. I
don't even know if you have an
audio book
Mark Ackers: on that one. I
don't know. I feel like the
accent would ruin it. So,
Will Aitken: yeah, word, I'm
sorry, mate, you and Richard,
Yeah, hello there. You know
the northern thing, especially
for American audiences. They
were like, What are they
speaking English
Mark Ackers: Exactly. So, no,
we don't. But again, I would
say that I feel like so
problem prospecting, which you
kindly reference, and then you
very kindly help promote
deconstructing discovery. I
actually passionately believe
that they are better to be
read because of how tactical
they are in the transcripts,
et cetera, that. And I do
think our accents would be
horrendous, but there we are.
But back to my point, you've
gone and read these books, and
I think this is the moment
when you realised, oh, hang
on, this is a skill. This is
something that you can learn
and something you can get
better at. Holy shit. Imagine
if I would have read these
books five years ago, and this
is where you go. Okay, if I
can just get this job, work
with these people, learn these
ways of selling, get get
surrounded by people that have
been where I want to be, got
what I want. If I can get the
coaching that I need, I can
build this career that Do you
know what I've always wanted?
And then here's the kicker,
you need for approvals gone,
because you're now working
with people that are and I
know you're saying the right
way at this point in their
careers ahead of you. They're
smarter than you, they're
ahead of you. They're further
ahead. They've done what you
want to do. Your egos had to
go. You've got a six month old
baby. You've got a family
that's depending on you.
There's no time for egos.
You've realised I'm in this
career. I can't get out of it.
This is a skill I've been
exposed to, this literature,
these books. I've got this
opportunity in front of me. I
actually don't care anymore.
Criticise my calls, because
when you do that, I get better
because you're coachable. And
this feels like just the key
moment where so many things
have come together, but the
best thing of all is you've
realised it's a skill, and
you've dropped your ego, and
you've lost the need for
approval, because you know
this is what's going to send
you down the path that you
want to get to, and where
you're going to do for your
kid what your dad did for you.
And I think this is just a key
moment for you, and I'm really
happy that you had that
moment, because it feels like
without it, where do you think
you'd
Will Aitken: be today? Maybe
trying my best learner trade
by I'm a clumsy man. It
definitely just did change my
life, and I think that also
speaks volumes to the quality
of the managers that I had. I
give them a lot of credit,
well, I don't give them enough
credit. Should I say, Well,
Mark Ackers: you've given them
a shout. I hear, what would
you say if someone's listening
to this and like I say, I
think most people listen to
this podcast that they're
ahead of that part already
because they are actively
seeking sales collateral, but
perhaps they are going for a
rut. They are blaming other
things. They are blaming and
pointing out, and they're
maybe not as open to coaching
and learning that they should
be what advice would you give
to them?
Will Aitken: What can you do?
Like what can you do, both in
actions and in learning right
now, they are always something
in your control. Excuses are
very toxic. I also don't like
people who are saying no
excuses, because I think that
leaves room for a lot of
prejudice as well. But
especially in sales,
accountability is vital, and
knowing that I didn't have for
a long time, it was really
hurting me not having so wake
up. You may have taken a job
that it wasn't everything I
promised, but be accountable
for the fact you accepted that
job. The emails might not be
getting opened. Okay, be
accountable for what can you
do? Can you make calls? No
one's picking up the phone.
Okay? Have you made enough
calls? Have you tried calling
other numbers? There's always
something you can do. You can
do. And if you just say, I am
in decision of this, I'm in
the control of this one, then
you start figuring out the
answers to those and knowing
what you can do, instead of
Mark Ackers: complaining about
what you accountability is
such a key word will and
actually, that's what coaching
provides, being accountable
and and I think this is the
thing that, again, lots of
people will just resonate
with. How many times have you
read something in a book,
watched something on maybe a
video podcast, listened to
something, heard something and
thought, well, great idea, but
then done nothing with it. And
it's because you're not
accountable. And that really
is what a great coach does.
It's where are you today? And
it sounds like this is what
your boss is. Where are you
today? Will I know where you
can get to? Do you want to get
there as well? Because if you
want that, that's great. If
you don't, we can't want more
for you than what you want for
yourself, but we see where you
want to get to. What are the
goals then? Okay? And now,
every time they meet you, it
is about, have you achieved
what you want to achieve? If
you haven't, why not? What are
the reasons? Let's break them
down, and what you're bringing
to the table is, well, I'm
going to point inwards. What
can I control? I can control
showing up. I can control
being coachable. I can control
my work rate. What I need from
you is the guidance, and I
don't know what I don't know.
And it's like a perfect
marriage between a really
hands on coach that can see
the potential, agrees with you
where you want to get to, and
works with you on a cadence
that's not about the number,
not about KPIs. It's about
actual sales acumen, sales
skills, and you're there,
hungry for it, and so
coachable, which, which is why
you've managed to go on to
have the career that you have
had. But accountability is at
the root of coaching, and if
you're not accountable, it's
very, very hard to achieve
those goals. And for anyone
that's thinking, Well, where
do I start accountability?
Journaling is the place be
accountable to yourself. I
know people that just every
day write down a few things
that they want to achieve, and
at the end of the day, have
they achieved it or not? It
takes a couple of minutes. I
will give a shout out to Steve
Myers, one of the coaches of
my sales coach, who's got his
own bagels. He calls it and I
won't do it justice once I
can't remember it, but it
stands for different things
about what you're looking to
achieve. But journaling is a
great way to start
accountability. Then then a
coach,
Will Aitken: yeah, yeah. No.
It just sounds like you and I
have similar things, similar
things I found to do list
journaling, but also getting
your feelings down there keeps
yourself aware and causes you
to make sure that you don't
get that ego back as well.
Because you gotta, you gotta
be keeping real of yourself.
Mark Ackers: So start to build
this exciting career that you
are and that you've gone on
where you are. Now let's start
with sales feed under Vidyard
now independent. Just give us
the headlines. What is it?
How'd it come about?
Will Aitken: Ironically, after
all this, after dropping the
ego, my ego made me leave that
company, because I went out
drinking with some other
account executives at the
company. We all got talking,
and as I told you, I'd been
the first rep to really even
hit quota yet alone, several
months in a row. And I found
out that I knew they were they
had the senior candidates
title, but they were being
paid much more aggressive,
both accelerators and a base
salary, and that made me
bitter and hurt. So I went to
my manager and said, Give me
the promotion. I've earned it.
And he didn't. So although I
had completely never, wouldn't
even consider leaving, because
I didn't get my instant
gratification from that.
Because even honest, the
things he said to me is, well,
there's no doubt you've earned
it from a sales performance
standpoint, but if you want to
be a senior thing, you've got
to be an example for the team.
And you show up on calls
sometimes and you're immature,
and you show up at cool
sometimes, and you don't
communicate, or think about
the way you'll communicate.
And I heard that, and I was
like, you're just giving me an
excuse because you don't want
to pay me more, versus
actually. And it's funny,
because that was that was
coaching, that was feedback,
but I didn't take it because I
was coming from a place of
emotion. So although I'd
actually shot down the idea of
working video, especially once
I found out that was actually
a marketing job, EO marketing,
no sales for life, when I then
had this, this kind of chip on
my shoulder that I hadn't got
the promotion I wanted. So
when took the interview, and
at this point, this is when
I'd started posting stuff on
LinkedIn, because, as I
mentioned, I moved to a new
city, I didn't really have
that many friends, and. And I
wanted something to do, so I
started making these videos,
just sharing what I was
learning in my day to day
sales, but also making some
skits and things that were
like almost laughing through
the pain of like the deals I
did lose like it. I thought
everyone must feel this, you
know. So I started making
these funny pieces of content
as well. Got on the this, uh,
Tyler sods radar, and he
wanted to bring someone in who
actually understood the sales
owners create content full
time. So when I started
talking to him, and he said,
Yeah, this role will pay this.
And the base salary for the
role was about the same as my
ote. I was over performing, so
it was less, technically than
the motel amount I was
earning. But it was a
marketing position, and it was
full base. So I was thinking
to myself, hang on, I would
get paid this and not have to
deal with, like, the end of
quota anxiety, end of quarter
anxiety, end of month anxiety.
I'm like, hang on a second.
And because I was still home
from ego, I was like, You know
what? I'm open to it. And it
was offering a job that was
basically my hobby at the
time. Was what I was doing for
fun. They wanted me to do that
full time, so I took
Mark Ackers: it, and really,
that's been a big turning
point for you. Well, a week
Will Aitken: later, I then got
promotion, right? But I was
net interviewing, and I was, I
was
Mark Ackers: hooked. Talk to
me a little bit about what it
takes to create funny content.
Where I
Will Aitken: found the most
success is one journaling,
because things happen to us
all day that are hilarious or
other people can relate to.
And when you're in sales,
other sellers could as well,
right? So being aware,
thinking about those, but then
also sometimes just saying the
quiet part out loud. We spoke
earlier about prospects who
give you the run around, and
you just do everything they
say, and then they end up
ghosting you because they got
all the information they need,
and then they got a lower
price point. That's where. Or
they weren't ever really
serious about buying in the
first place, or they were just
using you to get a price to
beat down one of your
competitors. Of these posts I
was speaking to three months
ago, you know, like those
things are things that happen
to every seller, right? Every
seller has felt those so if
you can point that out and say
it, or even make light of it
sometimes, then I think that
makes people nod and go, Oh my
God, that's so true. I think
that's normally where my mind
goes.
Mark Ackers: And has humour
always been your way of sort
of connecting with people?
Yes, when you're creating that
content, what do you do when
you put it out? It flops.
Will Aitken: Learn it didn't
hit. That's okay. What can I
learn from that? I there?
There have been ebbs and
flows. And here's the
challenge again, because
social media that that became
my entire life, it was my work
now, and you cannot control
algorithms and things. What
can you control again? It
comes back to accountability.
But I'm not gonna lie, this
has been a challenge in the
past. What's been like four
years where I've been doing
this so much on growing online
and doing it for myself and
other people? Like, there were
times where, like, I'm like,
I'm realising that. I've had
to realise and I've had to get
out of the idea of chasing
validation. Because what you
said earlier the world today
on social media especially, is
there's instant validation
everywhere you go when you
don't get it or you get too
attached to it, well, when you
don't get it, you're going to
be miserable, and that's not a
good place to attach any level
of your self worth. So look at
what you can if something
flops is not necessarily
because if they didn't do well
as well, it wasn't a great
idea. But like, over time, you
can't do it based on one
thing. Like you have to look
at the broader picture. How we
look at how's that theme or
type of content performing
overall, not just that one
piece. It sound like going,
Oh, that cool flopped. I suck
at cold calling. But no, look
at all the calls. What's the
what's the common themes?
That's when you need to start
looking into what to fix right
similar, similar things that
you can look at
Mark Ackers: there. What I
really love about that,
though, is straight West. It's
learn, like, learn wide and
and actually, what you said
towards the end as well, it
didn't flop, and I was
purposely provocative with the
word flop, but it didn't flop,
it just didn't quite land.
Like, the algorithm didn't
quite like it that day. Maybe,
like, I've got to learn about
when I'm posting it, or the
hook, etc. But here's the
thing, so many people are
still not well, you know, 99%
of people on LinkedIn aren't
posting. But those that do and
do it well, like you are able
to create big brands and
followings and off the back,
but you've got to put yourself
out there. And it's not always
gonna it's not always gonna
work. You've had a job, and
this is when I first really
feel like you come on my sort
of radar, so to speak, was
lavender. When you're head of
social there, tell me what was
the brief when you took that
Will Aitken: role twice the
money for the same job that
that was, that was the main
thing. That was
Mark Ackers: a driver for
taking it. What was the brief?
Will Aitken: Brief? We want
you to do more of what you've
been doing with salespeople,
but for lavender. And I said,
No, I love it here. I have an
amazing manager who I get
along with, who trusts me, who
still is willing to coach and
teach me in the place where I
need it, but for the most
part, fully believes in me and
took a risk on me. And then
they went, Yeah, but you know
how much this pays? And I'm
like, oh. And then I also had
a friend who had literally
just started working there,
Janell and Knuth, and we'd
become very good friends just
from living with him alive,
she'd become like an
evangelist. A challenger, I
think, at the time. And we
were kind of talking about
how, how we make sure that
this growing, these brands
actually drives revenue, and
we would like share ideas,
etc, and they wanted me to do
more of the same thing that I
didn't even say it has to get
better in any way. It's still
already great. That was
Mark Ackers: the proof. What
would you say when you think
about that role growth, head
of social it feels like from
the outside, there must be so
much fun. What's it really
like having that
Will Aitken: role? I didn't
enjoy it. I It wasn't the same
as what I've been doing. And
the reasons why I enjoyed what
I'd been doing were no longer
reasons. And then you've got
different people with
different expectations and
different management and
different opinions as well. I
think there was, at that point
I'd been doing it for long
enough where I knew I was good
at it. You know? And I was
getting a lot of validation,
both from online and
compliments and stuff and
performance and growth than
the brand I had been managing
and my own brand as well. I
thought I was just the best,
already, the best person who
could ever be in that role. So
I had ego, then I also had new
challenges, people who also
had ego, who had opinions, et
cetera. And that was probably
the biggest challenge. And I
stopped learning for sure for
a period of time there. And I
went like 2020 2023. Is
probably the worst year of my
entire life, because I didn't
believe in what I was doing. I
wasn't learning anymore. I had
stopped. I thought I was King
hot shit. And it affected my
life, not just personally,
professionally, but in my
personal life as well. I lost
friends that year, you know,
because I just had this aura
about me that I thought I was
too good, too successful,
making more money than I ever
thought I had, getting all
this external validation
deeply. I'd stopped getting
better. I'd stop learning, and
I wasn't doing
Mark Ackers: work. I actually
believed in it. How have you
become so self aware you do
you strike me as someone
that's just so aware of where
you've gone wrong, the
mistakes that you've made, the
ego that you've had, and
that's obviously not who you
are today. How have you become
so self aware? Because so many
people aren't
Will Aitken: I think it's an
ongoing thing. There are still
things that I've I'm aware of
today that I wasn't aware of
last week, and it's
willingness to be wrong, I
think. And you get kind of
good at it once you've kind of
started seeing patterns in
your past, behaviour, like,
what am I not seeing today
that I will think about in
three years? And also, like,
You're not meant to do it
alone as well. Whether it's a
partner, a boss, a coach, a
therapist, those people are
there to help you get to those
answers as well, and that's
why it's important to work on
yourself, be there for
yourself, who coaches you
today. Mainly, this is
something that I realised
recently that I want and I
miss, because most of the work
I've done on developing myself
has been with more like
counsellors, therapists and
other types of the folks like
that. I became very focused on
being a boss again, but I
still surround myself with
people who I do believe are
smarter than me and can point
out where I'm going wrong, but
I certainly haven't been as
actively coached today as I
would be, and that's why I'm
actually doing some some
things about that as well. I
will say that while writing
this book with Keenan, which
will be the prequel to gap
prospecting, which, as I
mentioned earlier, is a book
that means a lot to me,
because it was a lot to me,
because it was a big turning
point in my career. I've
learned a great deal from deal
with deal from him, and he's
been willing to coach me
essentially while we've gone
through that process together.
What amazing
Mark Ackers: coach to have,
right?
Will Aitken: And I'd end with
pay him.
Mark Ackers: What can you tell
us about this book that you're
working on? Yes,
Will Aitken: so I always
wanted to write something. I
enjoy writing. I want I know
that feeling that I had when I
first had the click moment.
You know, I thought sales was
a numbers game. I thought I
was just getting lucky. I
didn't realise it was a skill.
I thought there are some
people out there who haven't
had that moment yet, and
that's the type of person I
want to help. And the thing
that helped me was reading a
book that was actually really,
it wasn't just like, do this,
ask this question. In fact,
when you read that book, it
doesn't really spell out what
exactly you should do in
discovery. Just kind of breaks
out the mindset of, like,
effective discovery. I'd argue
your book is much more
prescriptive, right? But like,
the storytelling and it helped
me turn the pages and actually
get it in a way, you know, I
mean, and I thought, okay, how
can I do that for the other
part of sales that I didn't
feel? How can something that
good be possible for earlier
in the process, where I found
myself spending a lot of time
thinking about and talking
about prospecting. So I hit
Keenan and said, you wanna
write book? He said, No, I was
a year and a half ago. And
then hit him up again and
again and again, and I
prospected the shit, living
shit out, and then I probably
did some gap song on him. And
somewhere along the way there
where I asked him some
questions about his business
and what he wanted to do, and
never finally gotten to agree
to agree to it, because I
felt, I felt like I didn't
have all the answers, and I
also didn't feel like I had
the ability to put it in such
a compelling story as the
first time I touched that
book, and now, boy, this thing
is, it's coming along. Nice.
It's so good to read. It's
like, almost like a novel, you
know, that's, that's, I think,
what, well, what I like about
that? And I think there's a
place for both types of book
or content, so in the mix,
you've moved you or something
that helps you do something,
you know, and, yeah, so, yeah,
that's, that's the book. It's
going to be gap prospect, you
coming out this fall, if
everything still goes to plan,
but it's looking like it's
going to definitely happen in
probably September. I was
Mark Ackers: going to say
that's, that's when you know,
you've been Americanized when
you say it's coming out in the
Will Aitken: fall. Oh my God.
I said autumn. I'm sorry.
Mark Ackers: Whenever I hear
fall, I remember being a kid,
being frustrated whenever I
was in the cinema and the
trailer be coming out, as for
when is that? When is this
film coming
Will Aitken: out? The crappy
thing is, I've adopted that
word, but I don't say it the
same as all of them as well,
because they say fall, yeah.
And I say fall. You know, I
think northerners are probably
somewhere in the middle, but
depending on where you're
from, if you're if you're a
man, I think you'd say fall,
yeah, like halfway between. So
Mark Ackers: let's recap a
book with Keenan gap
prospecting the prequel to a
book that fundamentally
changed the structure of your
career. Incredible will, and
this is because you've had an
idea, you've made it happen.
You've used what you've
learned in your career to
prospect someone to make it
happen and and this is why
I've loved about talking to
you, is shits not always gone
the way you want it to go, but
you've always looked at, what
can I do, what can I control?
And you've made it happen. And
I think you're so self aware.
So let's talk about where
you're at now the business.
Well, I. Linkedin.com. Is what
it says on LinkedIn as well as
a great title, but ultimately
it says you're running the
business, coaching, training,
keynotes, content. Tell me
what's what's the mission.
That's something
Will Aitken: that I'm kind of
in the middle of figuring out
right now. A bit more in
depth, I did find that I I've
lost that as a couple of times
over the past year, since
running my business as well,
where, you know, you fall
into, back into old habits,
chasing validation, etc, as
well. The most impactful
thing, and I'm certain you can
relate to this that I've been
able to do since I started my
business is definitely not the
thing that made me the most
money, but it was just the
little part of my page that
said book a one on one
coaching call. Because you
know what that does, that
attracts people who are ready
to learn, who want to work on
themselves, the best types of
people and those conversations
and getting better at
coaching, which is a skill now
that I need to work on being a
better coach, because I've
never done that before as much
until I start offering it, and
then people start booking, and
then I'm just like that. I
need to get better at that
piece that has been the most
fulfilling part of my work by
far, because you get to see
these people, and you take no
credit for it as well. It's
them, but the right people
show up to that, the right
people seek it out, and then
the right people actually go
ahead and do the work. And
when you help them to get
there, they often see the
results. And that is just
feels good, man. So that's
been the most fulfilling
thing. So I'm now figuring out
how I could do more of that
without going broke, because
selling one on one, coaching
by the hour. I mean,
therapists do it, but it's
also not as scalable as I'd
like, so I'm still trying to
figure that part out, but
that's where I'm thinking. I
want to spend thinking, I want
to spend
Mark Ackers: more time.
Gotcha, what is the most
common bit of advice people
ask you for help on
Will Aitken: a lot of job, a
lot of work, like, I want to
get promoted. I want to get I
want to get a job in this but
funnily enough, most people
come to me with when they've
got something new going on.
The best thing about coaching
is when you can help someone
get to the answer themselves.
So sometimes someone comes to
you with what they think is
the problem, like they go, Oh,
this deal or this thing isn't
working, but then you can
almost help them collect that.
So most people come to me one
thing, but it's not really the
true issue. So it's either
like a new initiative or
ongoing prospect, or I've got
this new job and I want to hit
the ground running, but it's
like there's actually
something else there
underneath a lot of the time.
So when someone comes to me
like, there's this deal I
really want to move forward.
I'm like, Okay, let's unpack
that. I can tell you
immediately 10 things you
could try to move this deal
forward, but like, let's walk
back on that a little bit. And
that's when you see people
Mark Ackers: start to get way
better as well. And again,
being a great coach, you're
not connected to the outcome,
because it's them, like you
say, and you don't need the
need for approval, because
they're already coming to you
for the health and guidance.
You can ask those questions to
get to where you need to get
to. But then, like you say,
it's not about telling them,
it's, I love that. I love the
analogy of the movie
Inception. Have you ever seen
it? So sometimes what you need
to do is, is give them the
seeds so they feel like the
idea is actually grown in
their own head. Yes. And
that's that's when an idea
becomes really powerful. I
have genuinely love this chat.
I know anybody that's
listening to it will feel the
same. We've had some amazing
guests be open, honest, but I
think this is one of, if not
the most open, honest and
rawest of conversations that I
think so many people are going
to listen to and have that
either that's me or that light
bulb moment of bloody hell
that is, that is me. I didn't
realise it. People could
obviously find you on
LinkedIn. People can look for
your book that's not out for
pre order right now, I'm
guessing, given that this
Will Aitken: corn, there is a
link, or if you just go to my
newsletter page, I will be
sending out updates and pre
reads of that as
Mark Ackers: well. There we
go. I'd love, well, I'll buy a
copy when that comes out. I'm
looking forward to reading
that, and
Will Aitken: I sent you one
mate. Oh, well, I didn't want
to hint, but if I bought your
first book, but you sent me a
second book for free, so I owe
you now. Okay, well, the first
book was a good read. It was
well worth the money. So thank
you. Thanks very much.
Mark Ackers: Well, yeah, I
just want to end it there and
say thank you so much. That's
kind of what I'm getting to
thank you. And you know,
anytime that you're over in
the UK, let's definitely meet
up. Keep in touch. Well done,
mate. Thank you. You.