The Failure Revolution is well underway—a celebration of missteps, failures, and errors as pivotal moments of learning and growth. But how is a blunder different from a moment of growth? What types of mistakes are worth the learning, and which costly ones would rather be avoided? In launching over 250 digital products over the past 20 years, Highland is well-versed in the language of failure. We’re taking a moment to reflect on which failures are an intentional part of the process, which ones take us by surprise, and which ones we help organizations avoid. Come join us for some memorable stories of hits and misses. Attendees will learn: • The most common failure patterns in the digital innovation process, with examples from our lived experience. • How to recognize and avoid the most common failure points and patterns. • How to discern learning moments from expected failures, or worse—unexpected failures. • How to move from fearing failure to living failure, and dodging fatal failure.

1. Failing Like a Pro:
Distinguishing Healthy
& Unhealthy Mistakes
19 Nov 2020

2. How we’ve planned this time
● Who is Highland?
● The Art of Failure
● Vision, Translation, & Build Failures
● Stories of Failing Fast & Slow
● How to Fail like a Pro
● Questions?
● Networking/Mingling
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3. Housekeeping notes
● Thereʼs a lot to get through today! Donʼt worry,
youʼll get the slides and recording after.
● Share your questions throughout in the Q&A!
● Stick around after the presentation to video-chat
with attendees & Highlanders!
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4. 4
David Whited
Director, Research & Strategy Practice
Mike Nowak
Product Strategist
Jon Berbaum
President
With you today:

5. 5
Who we are
At Highland, we research, design, and
build digital products and experiences
for mission-driven organizations and
customer-centric companies.
Over 20 years, our team of researchers,
strategists, designers, and developers has
helped organizations launch over 260 digital
products, turning their biggest uncertainties
into opportunities for growth.

6. What we do
Project
Trigger
Contextual
Research
Synthesis
& Strategy
Ideation &
Prototyping
MVP Development,
GTM, & Iteration
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7. The Art
of Failure
Demystifying a grandiose concept
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8. Our biggest lesson has
been moving away from
“Failure happened to us”
and toward “We were
deliberate about failure”.
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9. 9
What does failing along the innovation
journey look like?
Project
Trigger
Contextual
Research
Synthesis
& Strategy
Ideation &
Prototyping
MVP Definition,
GTM, & Iteration
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10. 10
Where do different types of failure begin?
Vision Failures Translation Failures Build Failures
Project
Trigger
Contextual
Research
Synthesis
& Strategy
Ideation &
Prototyping
MVP Definition,
GTM, & Iteration
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11. Vision failures
happen when
we don’t clearly
connect a significant
user need with
organizational goals.
Common Vision Failures:
● Solving for a non-existent need
● Not discerning the deeper problem
● Executive enthusiasm as a proxy for
user understanding
● Lack of attention to business model & system
● Conducting evaluative research in place of
generative research
● Not acting on insights; instead, responding
with more research
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12. 12
Common Translation Failures:
● No plan for iterative design & testing
● Decision-making that ignores user insight
● Design unable to translate validated
desirability into usability
● Unwillingness to commit to an MVP
● Team unfit for task at hand
● Insufficient continuity between the design and
build teams
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Translation failures
happen when we
don’t connect the
team tasked with
creating the solution
to the original
insight and vision.

13. 13
True build failures
are mostly tactical
in nature and are
easily corrected.
Common Build Failures:
● Project plan has no margin for additional
learning
● Unempowered or under-skilled teams
● Lack of discipline
● Ineffective cadence between building and
ongoing vision check-ins
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14. 14
Most ‘build’
failures are the
manifestation of
‘slow failures’
introduced earlier
in the journey.
Earlier failures that manifest during Build:
● Product roadmap by committee
● Feature parity trap
● Sales pipeline dictates roadmap
● Spec-ing out new features without user insights
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15. 15
Getting deliberate instead of losing control
Fast & Slow
Failures
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16. “If we fail fast,
we call it learning.
If we fail slow,
we call it failure.”
— David “The Dude” Hussman
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17. Instead of risking a potentially
terminal wake-up call at the
end of a project, create small
bits of intentional ‘fast failure’
all along the way.
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18. Creating moments of fast failure
Project
Path
Fast Failures
lead to progress
and growth
Fast
Failure
1
Fast
Failure
2
Fast
Failure
3
The Slow Failure
Slow Failures
are difficult to
recover from
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19. Productive and unproductive failures
Vision Failures Translation Failures Build Failures
FAST FAIL:
Designing a product for
people that donʼt exist
SLOW FAIL:
Learning that entrepreneurial
lightning doesnʼt always strike
twice
FAST FAIL:
A Relationship Coaching App
Gets Lost in Translation
SLOW FAIL:
A Product to Facilitate a
Challenging Conversation
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20. 20
Learning that
entrepreneurial
lightning doesn’t
always strike twice
We built one very successful
product for an entrepreneur.
When he had another big
product idea, we didnʼt learn
that the target market wasnʼt
interested in the product until
after we built a costly MVP.
SLOW FAIL: VISION

21. 21
A Product for
People That
Don’t Exist
A new product we developed
was initially targeted at a
specific type of customer. Early
testing demonstrated that most
of the assumptions the early
product team had about the
target customer were wrong. We
learned we were wrong early
enough to pivot to a new
customer type with a much
higher propensity to purchase.
FAST FAIL: VISION

22. 22
A Relationship
Coaching App Gets
Lost in Translation
The team that took on the
product after early stage
research and prototyping didnʼt
build ongoing user testing into
their plan. There was also no
continuity between the early
design and build teams. Without
user insight, the product drifted
away from research evidence
and into arbitrary strategy
shifts.
SLOW FAIL: TRANSLATION

23. 23
Designing A Product
to Facilitate a
Challenging
Conversation
Our team uncovered a deep
unmet need for parents and their
adult children to have a
conversation about end-of-life
planning and financial legacies.
But bringing them together to
have that conversation proved to
be more challenging than we ever
anticipated. That learning led to a
much longer, but absolutely
crucial, prototyping phase.
FAST FAIL: TRANSLATION

24. 24
How To Fail
Like A Pro
What does it take to practice failing fast?
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25. Discerning between fast & slow in the moment
Or here?
How do
you know if
youʼre here,
Fast
Failure
1
Fast
Failure
2
Fast
Failure
3
The Slow Failure
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26. Failing slowly feels good to start!
Slow failure
feels good!
Fast failure
feels bad!
Fast
Failure
1
Fast
Failure
2
Fast
Failure
3
Slow Failure
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27. You’re failing slowly if:
Vision Failures Translation Failures Build Failures
● Youʼre not using generative
research to establish the
problem worth solving.
● You canʼt state a concise
value proposition.
● Youʼre consistently
referring to statements
as fact that are actually
untested assumptions.
● There is more enthusiasm
than understanding.
● Youʼre not using iterative
design and testing
practices.
● The original vision is
resistant to change.
● There is magical thinking
that fundamental clarity
will emerge during build.
● The strategy and design
team pitches the idea “over
the fence” to developers.
● You start observing
waning discipline around
user insight/feedback.
● Scope creep / feature
parity stands in for a
clear product vision
and value prop.
● The team lacks connection
with the original vision
and opportunity.
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28. Failing like a pro comes
with attitudes and behavior
practiced across individuals,
teams, and leadership,
with support from culture.
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29. 29
FAILING FAST AT A TEAM LEVEL:
● Develop a rhythm of ʻlearning loopsʼ—
intentional space to stop, learn, and adjust
strategy
● What goes in a Learning Loop?
○ A clear time frame
○ Clear learning goals
○ A research methodology and approach
that matches the goals
○ Clear roles and responsibilities for the
team leading the effort
○ Sufficient time to analyze learnings and
make necessary pivots in focus and
strategy

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FAILING FAST AT A LEADERSHIP LEVEL:
● Manage practice of frequent check-ins
● Build confidence in ownership of decision and
open communication
● Consistently act upon learning. Donʼt just sit
within inaction. Record that pivot.
● Demonstrate/model failure. Talk about your
failure as learning

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FAILING FAST WITH A SUPPORTIVE CULTURE:
● A relentless commitment to radiate learning that
challenges assumptions
● Develop your instincts around knowing when to
pivot or stay the course
● Incentivize fast fails… celebrate it!
(Or at least donʼt punish it)

32. Wrapping Up
That’s all for today, folks!
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33. Check out
Highland’s
podcast
series:
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34. Trying to create a digital product? Webinar attendees are
eligible for a free 45-minute consultation from Highland.
Email David with the subject line:
Failing Like A Pro Webinar
Let’s Talk
Want to keep talking?
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35. We’d love to talk more!
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David Whited
Director, Research & Strategy Practice
dwhited@highlandsolutions.com
Mike Nowak
Product Strategist
mnowak@highlandsolutions.com
Jon Berbaum
President
jberbaum@highlandsolutions.com

36. Thank You!
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