In this slight update to the original Wicked Problems talk, I give a few more examples of how we inadvertently create problems for future teams.

1. #PixelUP18 | @LolaOye
Short descriptive heading
1
Wicked problems:
The black holes we’re designing into
our future tech
#PixelUP18 • @LolaOye

2. #PixelUP18 | @LolaOye
Things to look out for
2
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CONVERSATION
You might find it useful to
save these slides for later
(I won’t read them out!)
Search online….things worth
a bit more investigation
Let’s take the discussion
online, I’m interested in
your views

3. #PixelUP18 | @LolaOye
Today, I’ll be talking about…
3
What a wicked problem is
The kinds of wicked problems we’re responsible for
The future problems we will need to address
Tips for tackling wicked problems

4. #PixelUP18 | @LolaOye 4
POVERTY
UNEMPLOYMENT
EDUCATION
CRIME HOUSING

5. #PixelUP18 | @LolaOye
10 Characteristics of complex social issues
5
1. Wicked problems have no definitive formulation. E.g.
Poverty in one place won’t have the same challenges as
poverty in another
2. It's hard, maybe impossible, to measure or claim success
with wicked problems because they bleed into one another.
3. Solutions to wicked problems can be only good or bad, not
true or false.
4. There is no template to follow when tackling a wicked
problem, although history may provide a guide.
5. There is always more than one explanation for a wicked
problem, with the appropriateness of the explanation
depending greatly on the individual perspective of the
designer.
6. Every wicked problem is a symptom of another problem.
7. No mitigation strategy for a wicked problem has a
definitive scientific test because humans invented wicked
problems and science exists to understand natural
phenomena.
8. Offering a "solution" to a wicked problem frequently is a
"one shot" design effort because a significant intervention
changes the design space enough to minimise the ability for
trial and error.
9. Every wicked problem is unique.
10. Designers attempting to address a wicked problem must be
fully responsible for their actions.
Source: Rittel, Horst. "Dilemmas in a General Theory of Planning." Policy
Sciences, 1973: 155-169.
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6. #PixelUP18 | @LolaOye
10 Characteristics of complex social issues
6
1. Wicked problems have no definitive formulation. E.g.
Poverty in one place won’t have the same challenges as
poverty in another
2. It's hard, maybe impossible, to measure or claim success
with wicked problems because they bleed into one another.
3. Solutions to wicked problems can be only good or bad, not
true or false.
4. There is no template to follow when tackling a wicked
problem, although history may provide a guide.
5. There is always more than one explanation for a wicked
problem, with the appropriateness of the explanation
depending greatly on the individual perspective of the
designer.
6. Every wicked problem is a symptom of another problem.
7. No mitigation strategy for a wicked problem has a
definitive scientific test because humans invented wicked
problems and science exists to understand natural
phenomena.
8. Offering a "solution" to a wicked problem frequently is a
"one shot" design effort because a significant intervention
changes the design space enough to minimise the ability for
trial and error.
9. Every wicked problem is unique.
10. Designers attempting to address a wicked problem must be
fully responsible for their actions.
Source: Rittel, Horst. "Dilemmas in a General Theory of Planning." Policy
Sciences, 1973: 155-169.

7. #PixelUP18 | @LolaOye
Today, I’ll be talking about…
7
What a wicked problem is…in our modern digital context?
The kinds of wicked problems we’re responsible for
The future problems we will need to address
Tips for tackling wicked problems

8. #PixelUP18 | @LolaOye 8
Legacy
technology
• Fixing one issue creates
another
• Lack of retained knowledge
• ‘Black-box’ software
• Poor maintenance practice
The Wicked Digital Quartet
Digital/ Technical
literacy
• Decisions made by the least
knowledgeable forums
• Inappropriate use of rhetoric
e.g. transformation, lean,
disruption
• Middle-management
resistance
+ Finance
• Zero-budgetting practices
• Incumbent vs venture
capitalists
• Misunderstanding full cost of
ownership
• Outdated IT Procurement
practice
+
Agile/ Lean
methodology
• Moving faster than ever
• Start now, fix later
• Empowerment of Product
Owners
• Lack of empathy within and
between teams
• Rushing towards new & next
+
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9. #PixelUP18 | @LolaOye
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Q: What are the consistent issues you are facing in your
transformation/ re-skin/ redesign/ re-platform / relaunch….
9

10. 10#NUX5 @LolaOye
A 100-year old institution that is responsible for ensuring music creators get paid
whenever their work is performed.
Having fallen behind the technology curve, they set an aggressive agenda to
overhaul end-of-life technology and create new web services.
They hire a strategic team, a systems integrator, select a CMS and want everything
to go in the cloud. The digital transformation team consists of 60 people. The first
product MVP is expected to demo to the board in 6-weeks.
CASE STUDY: ABC MUSIC

11. #PixelUP18 | @LolaOye 11
Agile/ Lean
methodology
• Start now, fix later
• Empowerment of Product
Owners
• Lack of empathy within and
between teams
Legacy
technology
• Lack of retained knowledge
• ‘Black-box’ software
• Poor maintenance practice
Digital/ Technical
literacy
• Decisions made by the least
knowledgeable forums
• Inappropriate use of rhetoric
e.g. transformation, lean,
disruption
• Middle-management
resistance
Finance
• Misunderstanding full cost
of ownership
• Outdated IT Procurement
practice
The Wicked Digital Quartet
+ + +

12. #PixelUP18 | @LolaOye
LOOK IT UP
12

13. #PixelUP18 | @LolaOye
Today, I’ll be talking about…
13
What a wicked problem is…in our modern digital context?
The kinds of wicked problems we’re responsible for
The future problems we will need to address
Tips for tackling wicked problems

14. #PixelUP18 | @LolaOye
Wicked problems from the user’s perspective
14
• Slow look-ups & searches - we often consider
these ‘performance’ issues
• Badly loading pages - on slow connections, we
blame it on ‘the network’
• Page disharmony & flat interactions -
because the dev had to do the last bit of design
• Dead-end journeys - because content isn’t
where it is supposed to be

15. #PixelUP18 | @LolaOye
ABC Music: Getting paid for your music at a live concert.
15
OLD*:
1 2 3 4 5 6 7
You, or
someone else
performs your
music
A record is
created as “a
set list”
The performer or their
representative sends a paper
copy to ABC Music
OR
Emails an excel spreadsheet to
ABC Music
ABC Music
transcribes
the set list into
their own
database
ABC Music
updates a
central music
database with
the set list
ABC Music
allocate
appropriate
funds to all
the co-
creators
The co-
creators are all
paid at the
end of the
next quarter
*Some steps have been removed for simplicity

16. #PixelUP18 | @LolaOye
NEW:
ABC Music: Getting paid for your music at a live concert.
16
1 2 3 4 5 5 6
You, or
someone else
performs your
music
A record is
created as “a
set list”
ABC Music
transcribes
the set list into
their own
database
ABC Music
updates a
central music
database with
the set list
ABC Music
allocate
appropriate
funds to all
the co-
creators
The co-
creators are all
paid at the
end of the
next quarter
3 4
The performer
or their
representative
completes a
‘live’ web form
Set list is
automatically
scheduled to update
the central music
database (offline)
The performer or their
representative sends paper copy
to ABC Music
OR
Emails an excel spreadsheet to
ABC Music

17. #PixelUP18 | @LolaOye
NEW:
ABC Music: Getting paid for your music at a live concert.
17
1 2 3 4 5 5 6
You, or
someone else
performs your
music
A record is
created as “a
set list”
ABC Music
transcribes
the set list into
their own
database
ABC Music
updates a
central music
database with
the set list
ABC Music
allocate
appropriate
funds to all
the co-
creators
The co-
creators are all
paid at the
end of the
next quarter
3 4
The performer
or their
representative
completes a
‘live’ web form
Set list is
automatically
scheduled to update
the central music
database (offline)
The performer or their
representative sends paper copy
to ABC Music
OR
Emails an excel spreadsheet to
ABC Music
Future wicked problems:
Created two new databases, did not re-platform
old ones
Song search had a new referencing system
Completely new login system (in addition to
existing one)
Hybrid venue search
!
!
!
!

18. #PixelUP18 | @LolaOye 18
• “Discovery” activities place too much focus
on end-user pain points and an idealised
future state
• Sprint 0 focuses on getting development
going
• Where do we uncover the current systemic
characteristics?
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CONVERSATION
We enable wicked problems with
Systemic/ Process
failures

19. #PixelUP18 | @LolaOye 19
• If I design it, they have to build it - I don’t
have to check if they can build
• If they don’t build it they messed up, not me
• Have I checked if they could be a part of
my design process?
JOIN THE
CONVERSATION
We enable wicked problems with
Individual failures

20. #PixelUP18 | @LolaOye
Today, I’ll be talking about…
20
What a wicked problem is…in our modern digital context?
The kinds of wicked problems we’re responsible for
The future problems we will need to address
Tips for tackling wicked problems

21. #PixelUP18 | @LolaOye
Digital inequality affects our ability to create
unified multi-device experiences
21
“3.4bn
feature phone users
vs. 1bn smartphone
Various (Unverified)

22. #PixelUP18 | @LolaOye
Quant equals Qual and some people are making
better use of that than others
22
“$1bn
Disney investment in
the Magic Band
wired.com

23. #PixelUP18 | @LolaOye
Desktop, web and mobile are no longer
meaningful design paradigms
23
“3.5tn
Searches per day via
Google Now

24. #PixelUP18 | @LolaOye
Today, I’ll be talking about…
24
What a wicked problem is…in our modern digital context?
The kinds of wicked problems we’re responsible for
The future problems we will need to address
Tips for tackling wicked problems

25. #PixelUP18 | @LolaOye
Idealising for the end user isn’t valuable if you
don’t take as much care to understand the
contextual constraints you have to design
within - even if those issues are not
immediately apparent to the end user.
25
Wicked Tip #1
How it works? Use a prototype (e.g. sketches or interactive) to run
workshops with as many internal stakeholders as possible.
Build your backlog based on blending user needs with the
constraints and opportunities uncovered during these workshops.
Eradicate as many “spikes” as possible!
Product Runway
How it works? Just as you would model a user’s journey, model the
system. Map out the needs one store/component has of another,
where things are stored and identify tactical pain points e.g. old
software, compliance.
This should be ‘human’ readable, it is not a data flow diagram or a
technical diagram. Make it big, use a wall and add to it over time.
System Journey Maps
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26. #PixelUP18 | @LolaOye
As a UX professional, it is no longer an
option to have low technical literacy - start
speaking dev, take time to learn about the big
legacy challenges most organisations face
and be pragmatic.
26
Wicked Tip #2
How it works? Spend the early part of any project sitting with,
talking to and learning from the development/IT teams.
This is not just about uncovering requirements, but also about
building empathy and mutual respect to tackle future problems
together!
Co-Location
How it works? Take a user story, and run your first idea session as a
joint sketch session with development. Make these short 30-45mins
and punchy.
Create a template so you get notes with each sketch, this is usually
the most informative bit, why did they see the solution this way?
This also builds a sense of shared ownership.
Developer + Design Workshops
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27. #PixelUP18 | @LolaOye
There is no blame game available to you.
“They” is replaced by “We”. There is no right
or wrong only good or bad, based on the best
understanding WE can achieve.
27
Wicked Tip #3
How it works? Track the failure points and compromises that are
likely to have the biggest impact. Monitor these through usability
testing, the analytics and user feedback.
For each failure point score:
1 - Low impact on customer
2 - Moderate impact on customer
3 - High impact on customer
Keep track of your debt scores and use it to prioritise!
Customer Experience Debt
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28. #PixelUP18 | @LolaOye
Short descriptive heading
28
“We cannot solve the problems we
have created with the same thinking
we used in creating them.
Albert Einstein

29. Thank you, keep in touch
@LolaOye
www.ownyourexperience.com