Personal insights from ScrumMaster Ulrika Park and a summary of ideas from other thought leaders in systems development and Agile leadership.

1. 50 Shades of
FAIL
Personal insights and a summary of ideas from inspiring
authors, thought leaders, teachers and co-workers
through years of Systems Development and Agile
Leadership experience.

2. Ulrika Park
ScrumMaster, SmartBear Software
Ulrika.Park@SmartBear.com
@ulrikapark

3. “Success depends upon previous
preparation, and without such
preparation there is sure to be failure.”
- Confucius
Learn how you can succeed in the most common areas of
system fails. Here are 50 of the most common “fails” in software
development and how you can learn from them.

4. System: Failure 1
Systems thinkers say our behaviors are the result of the
surrounding system, that errors made by people are
caused by the system.
But the systems are created by people, and people are the
only ones who can change the system. So, what do you do
to change the system?
Get allies.

5. Fail: IT 2
Governments and businesses continue to throw billions of
dollars into IT black holes.
That’s quite an oxymoron: So many failures in IT projects.
Still, there has been an extra-ordinary development of IT
services the last 50 years.
Do…… Waste money to explore, fail and learn.
Stop….. Wasting money by ignorance

6. Fail: Not Delivering 3
At the moment the most famous IT failure in Sweden is the
“One IT Road Map” project that one bank was working on
for several years. So many people spent so much money
on this project, and in the end they didn’t deliver.
This is the traditional Big Design Up Front (BDUF) concept.
After analysis for too long time, requirements are outdated
at the time for practical work. Now, hopefully, they know
how not to run IT projects.
Do….. Share your failure! Others can learn from you.
Stop….. Big Bang initiatives

7. Fail: Handoff 4
A thorough analysis up front isn’t necessarily all that bad,
and the process of gathering facts, trying out concepts and
analyzing domain can take up a lot of time.
The error often comes in the time for handoff. After doing all
this thinking and analyzing, one-way documentation is
handed off to the project team, which now has to do the
thinking all over again.
Do….. Keep your analysts, architects and designers
through the whole development
Stop….. Handoffs

8. Fail: Courage 5
IT failures can continue for years due to cowardice
managers, silent project managers or sheepish teams.
On a similar note, IT failures can be stopped by
courageous managers, vocal project managers or confident
teams.
Do….. Dare to say “No”
Stop….. Keeping quiet

9. Fail: .com 6
Most of us remember the .com bubble in the late-90s. So
many crazy initiatives, crazy stories, no account for money.
Seemingly simple problems were solved with amazingly
large budgets.
Thank you so much everyone who contributed to the
bubble! Without you we wouldn’t have e-commerce, e-
reading, mobile services, awesome navigations, social
networks and streaming media today.
Do….. Stop thinking, innovate even if you end up losing
Stop…..Trying to innovate without being crazy

10. Fail: Focus 7
Why do all brilliant developers and technical workers put
their time into new Facebook apps instead of, with the help
of technology, working on saving the world from climate
catastrophes, starving children and oppression?
Do….. Focus on human development
Maybe….. Stupid Facebook apps are the reason for the
huge spread of democratic media

11. Fail: Complexity 8
Complexity in systems make systems thinking fail. Not
necessarly bad, just less optimizable. Do you know if your
system is complex or not?
Do…... Amplify and dampen behaviors in complex systems
Stop….. Blaming the system when it’s complexity

12. Fail: Test 9
Some of the most common failures in software
development are:
• No usability testing
• No behavior testing
• No acceptance testing
• No business testing
• No unit testing
• No performance testing
• No security testing
Seeing a theme? Services and products just work better
with tests.
Do….. Test now!
Stop….. Waiting for code or extra time

13. Fail: Curiosity 10
When you stop being curious, you’re as good as dead.
Be curious about your co-workers across the office.
Be curious about your users.
Be curious about customers.
Be curious about your own limits.
Curiosity is evolution.
Do….. Look around you
Stop….. Looking inside yourself

14. Fail: Outside-In Thinking 11
Everyone talks about outside-in thinking, but how many
teams actually apply this idea?
Do you apply?
Do you go outside your tribe to find out?
Do you go outside your office to talk with users?
Do you let the outside world into your office?
Do you admit you don’t know anything about the outside for
every minute you are not there?
Do….. Go See
Stop….. Speculating

15. Fail: Comfort Zone 12
Do you fall into the same patterns over and over?
Do you test the same way you’ve always tested?
Do you analyze as you’ve always analyzed?
Document as you’ve always done?
How about your design?
And decision making?
Goals?
Welcome to the comfort zone.
Do….. Find and try a new technique
Stop….. Blindly repeating yourself

16. Fail: Ignorance 13
Nothing to add here.

17. Fail: Discipline 14
With discipline, you succeed. The more disciplined you
are, the more likely you’ll succeed in testing, in design, in
analysis, in leadership, in teamwork, in methods, in Agile.
How do you gain discipline?
Be relentless. Keep coming back to the practice when
you stray from the path.
Do….. Working agreements
Stop….. Follow the crowd

18. Fail: Groupthink 15
This psychological phenomenon has lead to crashed space
crafts, World Wars and, for us, failed IT services and
investments.
Do….. Aggregation of opinions
Stop….. Continuous problem solving within closed groups

19. Fail: Blah, Blah, Blah… 16
Okay, let me be a bit more clear:
Talking without a message.
Writing without clarity.
Setting goals without acting.
Instructions without respect for the reader.
Documentation without purpose, recipients or maintenance.
Do….. Consider the recipient of your message, visualize,
get feedback and act.
Stop….. Writing heavy documents or fancy statements just
to feel good about yourself

20. Fail: Documentation 17
This could be either a lack of documentation or an overflow
of documentation. Neither is helpful, and documentation
needs to be helpful.
Have you tested your documentation lately? If you’re not
sure who to test it with, or don’t know the recipient, then
why did you bother writing it in the first place?
Do…… Get to know the recipient of your documentation.
Find out what she wants. Ask someone else to summarize
the core of your doc.
Stop…… Document by habit and feel good about it

21. Fail: Communication 18
Communication is the second largest cause of all systems
failures.
Many research on project failures points to this.
Do….. Find ways to have real conversations
Stop….. Emailing

22. Fail: Constraints 19
People work most productively under well-thought-out
constraints. Empowerment without some frames and pillars
to hold on to will fail.
Leadership is to find good balance in constraints.
Do….. Decide on broad, clear constraints that allow your
team to think and act
Stop….. Micromanaging or ignoring the need for rules

23. Fail: Trust in People 20
Do you trust your manager? If not, what would make you
trust them? Tell your manager.
Do you trust your co-worker? If not, what would make you
trust them? Tell your co-worker.
Do you trust your team? If not, what would make you trust
them? Tell your team.
Do….. Make an effort to gain trust
Stop….. Believing people around you trust you by default

24. Fail: Trust in Technology 21
Do you trust your software? If not, what would help you
trust it?
More tests?
More information from your users?
Shorter delivery cycles?
Go get it. When you trust your software, your stakeholders
will trust you.
Do….. Whatever it takes to improve trust
Stop….. Waiting for others to do it for you

25. Fail: Business Alignment 22
Failures in IT projects are often a result of failure in
business and IT communication.
What have you done lately to bridge this gap?
Do….. Take the first step. Invite the other side to your party
(or just over to your desk).
Stop….. Blaming the other side

26. Fail: Requirements 23
Failures in requirements are still one of the most common
causes of failure in IT.
Requirements = Communication between business and IT.
Do….. Find ways to have continuous conversations with
the supplier or client.
Stop…… Emailing

27. Fail: Resources 24
People are people. They are not resources. They are not
capital. They are humans.
Do….. Treat people as thinking beings
Stop….. Calling them resources

28. Fail: Opportunities 25
I’m sure we miss business opportunities every day.
Sometimes this is unavoidable, but there’s no excuse for
lack of focus or lack of courage to stop what we’re doing to
go for the opportunity or take risks.
Do….. Dare to stop the line when you see an opportunity
Stop….. Keeping your stakeholders comfortable

29. Fail: Plans 26
Plans are nothing, planning is everything
A plan is just a hypothesis of the future; treat it as a
hypothesis. Test the plan and adjust it with new empirical
data.
Do….. Communicate a plan as what it is – an idea
Stop….. Viewing a plan as fact

30. Fail: Estimates 27
How many times have you heard about, or worked off
of, estimates that weren’t accurate?
The latest story I heard: A project that was estimated to
take two months turned out to be a 16-month project, which
actually succeeded in value.
Do….. Continue to update and share estimates during the
project as you gain more information
Stop….. Acting as if initial estimates are the truth

31. Fail: Time 28
“Time is not important, only life is important”
– Mondoshawan, The Fifth Element
When time flies I stop and think, “What is really
important, right now?” Without prioritization I’m for sure
gonna fail.
Do….. What is really important right now
Stop….. Multi-tasking

32. Fail: Creativity 29
When professional people come together to set goals and
a vision for the future, they tend to schedule meetings to
get things structured and completed quickly.
You can’t schedule creativity. What you need is to get out of
the office.
Do….. Go on a boat and have dinner with colleagues
Stop….. Filling your schedule with meetings

33. Fail: Objectives 30
Pia Gideon and other friends have told me, “We usually put
80% of our time in defining vision, goals and targets; 20%
to understand our current situation.”
If you flip this around, true understanding and clear
objectives will appear by themselves.
Do….. Put in a lot of time to map your current situation
Stop….. Putting a lot of time into defining the perfect
objectives

34. Fail: Measures 31
Defining a measure will take your team, product or
organization somewhere.
Lack of measures will lead to a lack of clarity in direction.
Still, you will get what you measure.
Do….. Be careful
Stop….. Counting money. Qualitative measures can take
you further.

35. Fail: Incentives 32
So you want your team to act as a team?
Are they measured as a team or as individuals? Can they state
their incentives to work as a team, to get the slow member on
board, to let go of pride, to help the other team? Are there really
incentives to do any of that?
Do you get any reward for acting as a team? If not – tell an
influencer.
Do….. Reward the effort you want
Stop….. Bullsh*tting about team work if individual performance is
what really counts

36. Fail: Capacity 33
Do you have a grand initiative going on? A cross-
organizational project? Nothing happens?
Did they get the capacity or room to engage? Capacity is
key for action.
Do….. Start with allocating capacity. Then initiate programs
or projects.
Stop….. Starting initiatives without capacity

37. Fail: Supplier-Client relations 34
The supplier wants to cheat you.
The client wants to get everything for free.
These are most common assumptions I have met about
suppliers and clients. Why on earth are you even working
together?
Do….. Find a supplier or client that you actually like and
trust. Make them partners
Stop….. Buying from or selling services to “counterparts”

38. Fail: Envy 35
So much trouble is caused by envy. This is especially true
in large organizations. Envy will kill your position, your
team, your organization and the sources of your success.
Do….. Make an effort to stifle envy when you see it in your
workplace
Stop….. Waiting for someone else to stop it

39. Fail: Silos 36
Does anyone today really believe we can succeed in business
by continuing to work in isolated silos like “finance,” “marketing,”
or “IT”?
Well, it worked once before, so is it really a failure?
Let your customers decide.
Do….. Map and visualize your customers’ journey through the
company
Stop….. Acting as if customer experience ends at your doorstep

40. Fail: Silos in Silos 37
Editors doing editing.
Web department doing website.
Mobile department doing mobile.
Back-end systems group doing back end.
Customer service doing customer dialogue.
All on their own.
Do….. Cross silo teams. Yes, it’s hard and demands a lot of
slack and idle time, but the result will be worth it.
Stop….. Creating even more silos

41. Fail: Matrix Organizations 38
One idea that is popular is to have functional managers
leading groups of people with similar skill sets, then having
cross-functional projects lead by project managers.
This idea sounds very appealing. The problem is, capacity
is never there. Managers try to make deterministic plans of
resource allocation to address this, but these plans
continue to fail.
Do….. Create long-term feature teams, product teams and
process teams instead
Stop….. Wishful thinking of deterministic resource
allocation

42. Fail: Slack 39
To achieve any kind of change, we need to give some
slack. But how are you supposed to create that space of
slack without creating an organization full of slackers?
Do….. Decide a time limit for slack (for example one day,
two hours/week, etc.) and start from there
Stop….. Assuming change will take place without changing
conditions

43. Fail: Sticking to the Rules 40
“We have always done it this way,” shouldn’t be an
argument, explanation or reason for anything.
If everyone took that as an answer no evolution would have
ever happened.
Do….. Question the ones saying that
Stop….. Do as we’ve always done

44. Fail: Be Embarrassed 41
Have you ever been on stage squirming in agony as you
fail to hit that high note or nail the punch line?
We have to make a fool of ourselves sometimes in order to
develop ourselves and our surroundings. That’s how we
change, how we grow.
Do….. Step out of your comfort zone and make yourself
look stupid once in a while
Stop….. Playing cool

45. Fail: Maps 42
Some failures can send you in the wrong direction for a
long time.
Everyone expected an Apple failure after Steve Jobs, was
this a self-fulfilling prophecy?
How much can a single failure, in this case Apple Maps,
damage a brand? I guess we’ll have to wait and see.
Do….. Move on, learn from mistakes and deliver better stuff
next time
Stop….. Releasing too poor quality stuff

46. Fail: Forms 43
How many times have you filled out an extensive
form, pressed the wrong button and lost an hour’s worth of
work?
How many times have you unknowingly been charged for
something after pressing a button on a form?
Nothing makes users as mad as forms.
Do….. Usability test your forms!
Stop….. Believing that users will follow happy path

47. Fail: Design 44
With design you steer actions.
By design you can steer behaviors.
By design you can change behaviors.
By design you can cement behaviors.
Do….. Hire a user experience designer to your team - Now!
Stop….. Deprioritizing design work

48. Fail: Operations 45
When our fancy project is delivered, the real action starts.
At this point, money is often running low and everyone has
moved on to the next project.
For successful business, you have to operate your service
or product.
Do….. Include operation in your design
Stop….. Believing any software release is ever over

49. Fail… To Fail 46
The worst thing you can do when trying to achieve
something great is to never fall. Could you have ever
learned to ride a bike if you weren’t willing to fall first?
You can’t excel without failures.
Many great leaders have a miserable history of failures.
Do….. Strive to fail
Stop….. Hold too tight to the boundary

50. Fail… And Recover 47
Great entrepreneurs often have a miserable history of
failures, and yet they keep coming back with new ideas -
adjusted ideas.
They brush the dust of the shoulders and go back to the
arena.
Do….. Instantly, get back up on your feet
Stop….. Believing it’s not your path

51. Fail: A Necessity 48
How can you succeed if you don’t know what it means to
fail? If you’re on the top without failures in your luggage,
expect something to happen.
Failure is part of life and human development.
Do….. Fail
Stop….. Being arrogant

52. Fail: Fast 49
The sooner you fail, the sooner you recover.
Since your product or service will inevitably fail in someway (by
target, by quality or by design) it’s better to pinpoint the problems
early so you have the chance to refactor, improve and adjust it
based on the new information.
This is the point of short release cycles.
Take a look back at the first versions of Google Docs. How good
were those?
Do….. Get it out!
Stop…... Trying to be perfectly “safe”

53. Fail: Forward 50
We can use failure as a tool, as with any other experience.
Use it as a stepping stone for success.
By knowing failures will happen, we might even be able to
avoid the worst ones.
By standing tall, facing the storm and admitting when we
fail, we will make a new and better delivery for our beloved
customers.
Have you ever been there?

54. Some inspirations and sources
Standish Group – Chaos Report Friends & other thinkers:
Authors: Abraham Lincoln
John C. Maxwell Contra Mestre Boquinha
Tom deMarco Anette Lovas @nettanis
Dan Roam Anders Eklund
Mary & Tom Poppendieck Per Axbom @axbom
W. Edwards Deming Arne Roock @arneroock
Gojko Adzic @gojkoadzic Agile Alliance Board Members
Kimball Fischer Pia Gideon
Dave Snowden @snowded Martin Persson #OutdoorFriday
David J. Anderson @agilemanager Eisenhower
Esther Derby, Diana Larsen
Jeff Patton @jeffpatton TheFunTheory.com
Craig Larman Fifth Element movie
James Surowiecki Stockholm Improvisationsteater
And many, many others… people I worked with, organizations & authors.

55. Find more cool resources on our blog and on
Twitter via @SmartBear