The document outlines 12 significant risks that can affect enterprise software projects, highlighting the importance of recognizing and managing these risks to improve project success. It provides a structured approach to risk management, including identification, analysis, planning responses, documentation, communication, and monitoring. Additionally, the presentation emphasizes that proactive measures can mitigate potential negative impacts of risks such as resource constraints, changing requirements, and organizational changes.

1. 12 Risks to Enterprise
Software Projects
(And What to Do about Them)
Payson Hall, Consulting Project Manager
Catalysis Group, Inc.
payson@catalysisgroup.com
1
Target Audience
Session most useful if you develop:
• Large systems that interact with other
production systems
• Systems that replace existing systems
• Production system (migrations) for new
environments
• (Bonus): Build Public Sector systems
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2. What’s In This For You?
Every large project is unique, BUT...
• Often face similar challenges
• When succumbing to challenges, projects
exhibit common patterns
• Patterns can be mapped to risks
• Addressing these risks improves your
chances of success
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Who Am I?
• Wrote my first computer game 1975
• Professional IT career began 1980
• Software start-up 1982-1986
• BS CS 1986
• Systems Integrator 1986-1991 (PW & IBM)
• Independent IT & PM consultant since 1991
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3. Goal
A facilitated conversation
•
Share patterns of trouble I’ve observed
on large, very large, very very large, very...
•
Enable you to anticipate and avoid
problems; or
•
Better recognize and mitigate them
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Approach
• Frame patterns as risks
• Present risks
• Discuss measures to
• Avoid the risk
• Reduce the impact
• Improve early warning
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4. Agenda
1. Quick risk tutorial
2. For Risk = 1 to 12
Review Risk
Discuss examples
Explore remedies
3. End
4. Q&A - Close
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Risk Tutorial
What is a “Risk”?
• PMBOK
Guide - 4th Edition:
“An uncertain event or condition that, if
it occurs, has a positive or negative effect
on a project’s objectives”
®
• Best definition ever (IMO):
“Uncertainty that matters”
- David Hillson
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5. Describing a Risk
A well-formed risk generally follows one of
two templates:
If <thing that may happen> then
<consequence> might be the result
<Statement of existing situation> may
lead to <consequence>
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Risk Management
1. Identify Risks (Write them up)
2. Analyze Risks (Decide how much you care)
3. Plan Responses (Describe what to do)
4. Document (Risks & your decisions)
5. Communicate (Risks & confirm decisions)
6. Monitor (Keep watching - Repeat 1..5)
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6. Identify Risks
• History with similar projects
• Input from SMEs regarding current project
• Critical Path
• Precious Resources
• Key Milestones
• External Dependencies
• Undocumented/Incorrect Assumptions
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Analyze Risks
Details exceed our time together (see article
for more information), but it is helpful to
think of risk in three dimensions:
• Probability - How likely is this?
• Impact - How bad will it be?
• Difficulty of timely detection - Will we
see this coming or be blind-sided?
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7. Plan Responses
• A pretty list of risks is useless
• Using the list to guide actions is helpful
• Decrease probability
• Decrease impact
• Improve ability to detect
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Document
Leave an audit trail of
• What was identified
• How significant you thought it was
• What you propose doing about it
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8. Communicate
• Keep project sponsors informed
• PM & team recommend, sponsor decides
• Only sponsor can decide a risk is
“acceptable”
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Monitor
Ongoing process of: identifying new risks,
(re-)analyzing identified risks, plan responses,
documenting, communicating, and responding
to risks that occur
Common error:
“Doing risk management” at the start,
then putting results on the shelf - like
“eating once and for all”
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9. Twelve Risks
For Risk = 1 to 12
Your Input
Here
Review Risk
Discuss examples
Explore remedies
End
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Risk 1: Perspective
If team loses perspective on the role and
motives of our systems integration vendor it
can make effective change management more
difficult
18

10. What & Why
19
What to do?
• Reduce Probability
• Reduce Impact
• Reduce Difficulty of Timely Detection
20

11. Risk 2: Conversion
The difficulty & complexity of data
conversion and data cleansing make it
difficult to estimate and could delay the
project
21
What & Why
22

12. What to do?
• Reduce Probability
• Reduce Impact
• Reduce Difficulty of Timely Detection
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Risk 3: Tight Schedule
If the schedule is very aggressive and highly
optimized, this may amplify the consequences
of other risks that occur on schedule,
budget, and scope/quality
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13. What & Why
Task A
Task A
Task C
Assume Task A & B equally likely to finish:
• Early
• On Time
• Late
On Time
Late
Task B
Task B
Early
5/9 = 55%
How likely that Task C starts late?
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What to do?
• Reduce Probability
• Reduce Impact
• Reduce Difficulty of Timely Detection
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14. Risk 4: Org Change
The scope of organizational change required
to implement the system is difficult to
estimate and could jeopardize successful
implementation if not fully addressed
27
What & Why
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15. What to do?
• Reduce Probability
• Reduce Impact
• Reduce Difficulty of Timely Detection
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Risk 5: Interfaces
The scope of existing interfaces may make
implementation complex and require close
coordination and synchronization with
adjacent systems that could
disproportionately impact schedule
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16. What & Why
Before
New
After
New
Magic
Magic
B
C
A
A
Legacy
B
C
Legacy
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What to do?
• Reduce Probability
• Reduce Impact
• Reduce Difficulty of Timely Detection
32

17. Risk 6: Resources
Resource constraints may make the project
schedule extremely sensitive to staff
downtime and turnover
33
What & Why
34

18. What to do?
• Reduce Probability
• Reduce Impact
• Reduce Difficulty of Timely Detection
35
Risk 7: New Tech
During the project new technologies will
emerge that could positively or negatively
affect project cost or duration and product
quality and functionality
36

19. What & Why
37
What to do?
• Reduce Probability
• Reduce Impact
• Reduce Difficulty of Timely Detection
38

20. Risk 8: Context
During the project the sponsoring
organization may experience changes in
priorities or goals that will result in changes
to the project goals and constraints
39
What & Why
The World
Organization
Project
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21. What to do?
• Reduce Probability
• Reduce Impact
• Reduce Difficulty of Timely Detection
41
Risk 9: Requirements
During the project the requirements may
evolve and require changes to the project
scope, schedule or resources
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22. What & Why
Changed
Original
Requirements Rate of Change 2% per Month?
1000
750
500
1000
980
920
900
880
860
840
820
780
940
800
960
100
120
140
160
180
200
40
Mar
80
220
60
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
250
0
0
Jan
20
Feb
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What to do?
• Reduce Probability
• Reduce Impact
• Reduce Difficulty of Timely Detection
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23. Risk 10: Implementation
The complexity of go-live may be difficult to
estimate and manage and may result in a
need to “un-implement” (back out) the
system one or more times
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What & Why
Production
Development
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24. What to do?
• Reduce Probability
• Reduce Impact
• Reduce Difficulty of Timely Detection
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Risk 11: Pacing
The long duration of the project may result
in the team and the supporting organizations
misperceiving project urgency that could
result in schedule delays
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25. What & Why
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18 Month Project (Month 1)
S
F
Welcome aboard! Looking forward to working with
you all. We will be procuring a new facility for the
project team while we select a product and vendor.
Hope to have the RFP out by the end of next month.
Keep your fingers crossed!
50

26. 18 Month Project (Month 2)
S
F
Great work team! We’ve narrowed facility search to 3
locations & everyone enjoyed the tours. Final selection
this week. Hope to start moving next month. RFP
release delayed two weeks by legal review. We will be
just settling into our new digs when RFP goes out.
Boxes for packing will be distributed next week.
Potluck when RFP released.
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18 Month Project (Month 3)
S
F
Final facility selection complete, but phones and such
won’t be hooked up for another two weeks. Move
date to be determined, but don’t unpack anything you
don’t have to. RFP finally back from legal and should go
out in a week or so. Looking forward to the potluck.
We are a behind schedule, but things should settle
down after the move.
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27. 18 Month Project (Month 4)
S
F
RFP released! Potluck was a hit! Mary promises to
post the recipe for her tuna casserole in the break
room when we get moved. Moving to new facility next
month.
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18 Month Project (Month 5)
S
F
Settling in to our beautiful new facility. Team still
unpacking boxes and setting up furniture. Tech support
promises that the LAN and printers should be set up
next week. More vendor questions than we
anticipated with the RFP, working to get an addendum
out this month so that we can get vendor final
proposals next month.
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28. 18 Month Project (Month 6)
S
F
Legal had a few issues with the addendum, but it should
go out next week. All systems up and running. I think
it’s time for an office warming potluck! There is
definitely light at the end of the tunnel. Thanks for all
your hard work with the addendum and getting the
office settled.
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18 Month Project (Month 7)
S
F
Proposals are due next month. After a brief transition
period, I will be turning project management duties
over to Mary Smith. It has been a pleasure working
with you all and I wish you best of luck on the project.
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29. 18 Month Project (Month 8)
S
F
I want to the thank the team for making me feel so
welcome. Vendor selection is complete and legal is
finalizing a contract so that vendor staff can start
work. We hope the vendor will be on site next
month...
57
18 Month Project (Month 9)
S
F
Legal promises there are just a few more contract
details and then the vendor should be able to start
after the holidays...
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30. What to do?
• Reduce Probability
• Reduce Impact
• Reduce Difficulty of Timely Detection
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Risk 12: Momentum
The organizational commitment to a project
of this magnitude can lead to a sense of
inevitability and momentum that may cloud
judgement regarding whether we could
continue the project in the face of evidence
to the contrary
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31. What & Why
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What to do?
• Reduce Probability
• Reduce Impact
• Reduce Difficulty of Timely Detection
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32. The Last Slide
• Q &A
• Questions Later?
Payson Hall
payson@catalysisgroup.com
Twitter: @paysonhall
Thank you!
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