Win Over Clients

Win Over
Clients—
Ask Powerful Questions
@theChrisDo
YouTube.com/TheSkoolRocks
TheFuturIsHere.com
facebook.com/BizOfDesign

©2016 Chris Do @theChrisDo #BizOfDesign
Anybody here love their clients?
Maybe a more relevant question is anybody
here have clients that love them?
Let’s change that.

#WinClients

What are you worth?

5
$ XX /hr.

Are you getting: $50, $75, $100 and hour?
Over $100? How about $500? Congrats.
Now, would you be shocked if I told you, I
have clients who are happy to pay me more
than $1000 an hour?
How is that possible? What am I doing
diﬀerently that makes me more valuable?

1x 10x 100x

Why can some designers charge 10 or even
100 times more than another designer?

What makes them
more valuable?

Any ideas? Is it the quality of the work they
do, the experience they have, number of
awards, staﬀ or size of their studio?
What do you think it is?
I’ll tell you why a little later, but here’s a hint:
the answer is in the question.

What would you charge to create
this symbol?

Why can design icons like Michael Bierut or
Paul Rand charge six ﬁgures for a logo?

You could draw this.
You know how to use
illustrator right?
So it’s not a matter of
technical skill.

Amateurs vs.
Experts.

15©2016 Chris Do @theChrisDo #BizOfDesign
Doc, I have a pain
in my eye.

Imagine this—You go to see a doctor. Upon entering the room,
the doctor asks you, “What seems to be the problem?” You tell
him, you are experiencing pain in your eye. He nods, asks a few
more questions.
Then, he writes a prescription. His prognosis? Get a new
wardrobe—your style is all wrong. Your clothes don’t fit you and
frankly, they look cheap.
BTW, he says, “I happen to sell clothes.”
What’s your feeling about this doctor? Offended? Annoyed?
You’d be right in wanting a second opinion.

17
Amateurs
give advice.

Is this a practice you’ve been guilty of as a freelancer or 
business owner? 
 
As creatives on the service side, we tend to not have many
opportunities to be clients. Therefore, we can overlook what it might
feel like when someone talks to us this way.
Getting “unsolicited advice” from someone can be downright
aggravating. The problem is, we don’t like being told what to do,
especially from an uninformed point of view.
Amateurs give advice.

So what do experts do?

20
Experts
diagnose.

Experts ask questions.
Lots of them.
They run tests. They eliminate variables. They look at your history
and behavior.
Only after careful observation and diagnosis do they form a
hypothesis. Then they take measured steps to test and validate.
Asking smart questions is what makes them an expert.

Slow down.
#premature

In design culture our tendency is to move
fast. Get it done. Go go go.
Slow down.

Thales 
624 – 546 BC

Let’s go back a couple thousand years to
Greek philosopher, mathematician, and
astronomer, Thales.
When asked, “What’s the most diﬃcult 
thing in life?”, Thales responded, “To know
yourself.”

Self Actualization
Maslow’s Hierarchy of Needs
Survival
Security
Belonging
Importance
+
-

What the easiest?
Give advice.

Do you know what
makes some people
more valuable?

The answer—

Your value
is determined
by the quality
of the questions
you ask.

So what are good questions to ask?
Good question.

Low vs. High
value questions

Quantitative, fact based questions are
important for getting the job done, but tend
to be lower value questions.

What does it look like?
When is it due?
Who is the target market? 
What is the budget?
+
-

Qualitative questions tend to be higher value.

How did you come up with
this idea?
How do you want people 
to feel?
How will you judge if this is
successful?
+
-

High value questions surface “purpose”.
They tend to cause people to be more
reﬂective. You are helping people, companies
or organizations to know themselves.

Why is this important?
Why do you believe this to
be true?
Why did you start this
company?
+
-

How valuable is this?
The world’s largest management consulting
ﬁrms are paid tens of millions to tell
companies “why they started”.

Steve Jobs
“Think Different” internal meeting. 
Sept. 23, 1997
Watch the video

Ask questions to
surface deeper
meaning.

What can you discover if you ask deeper
questions? You can help align a company
around a shared purpose which serves as a
decisional ﬁlter to govern all decisions.
Here’s an example.

45
From vendor to
advisor to ﬁduciary.

and its people around a shared purpose—
which serves as a decisional ﬁlter to govern
actions, new initiatives, investments, hiring
practices, marketing eﬀorts.

47©2016 Chris Do @theChrisDo #BizOfDesign
Win Clients?

Stop selling.
Start closing.

When you say it, you are selling. No one likes
being sold to. In fact, we instinctively resist
and distrust those that sell to us.
When they say it, you are closing. If you help
a client realize the problem and solution, you
don’t have to convince or persuade.

You could spend the next couple of years
meeting with clients, experiment with
questions and make adjustments as you go.
I’ve done exactly that, and have come to the
realization that there are 3 “golden questions”
you can ask in almost any meeting.
Here they are—

3 Golden
Questions

1.
What are you trying
to accomplish?

2.
What’s getting in the
way of you achieving
this goal?

3.
Why do you believe this
to be the case?

The next part is
the hardest part.

Be 100%
present.

Surrender 
your ego.

Act as if.

Stay in the diagnostic
phase for as long as
possible.

Talk to strangers.

Be an 
interesting person.
Be interested 
in people.

and its people around a shared purpose—
which serves as a decisional ﬁlter to govern
actions.

One ﬁnal story

Meet
Carrie

Carrie is someone I’ve been coaching. I had
a simple exercise for her— find a client that
you don’t want to work with. Maybe, it’s
someone who can’t afford your services or
has a project you’re not really interested in.
Instead of trying to sell your client, try your
best to help them. Serve them without
benefitting yourself in the process.

The very next day, Carrie sent me a text
exchange she had with her client.
The results were pretty incredible. Carrie had
helped her client win a piece of new
business, something which her client hadn’t
been able to do for months!

How was this possible?
Carrie acted in a selﬂess way and was in
service of her client.
How did that make Carrie feel? Well, for the
ﬁrst time in a long time, she felt like an expert,
in control, happy, and…
valuable.

Appendix

Win Without Pitching Manifesto
by Blair Enns 
buy on Amazon
Brand Flip
by Marty Neumeier
buy on Amazon
Zag
by Marty Neumeier
buy on Amazon
Delivering Happiness
by Tony Hsieh
buy on Amazon
Reference:
Start With Why
by Simon Sinek
buy on Amazon
Influence, The Psychology of Persuasion
by Robert B. Cialdini, Ph.D.
buy on Amazon
Value Proposition Design
by Alexander Osterwalder
buy on Amazon
Slide:ology
by Nancy Duarte
buy on Amazon

@theChrisDo
YouTube.com/TheSkoolRocks
Facebook.com/BizOfDesign
#TheFuturIsHere #WinClients

Win Over Clients

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