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Managing	Agile	Projects	Under	Uncertainty	-	
An	Organizational	Perspective	*	
Featuring	Guest	Speaker	Philip	Lew	
Moderated	by	Ying	Ki	Kwong	
	
*	A	webinar	event	on	March	5,	2019	co-sponsored	by	PPLF	and	the	
Board	of	PNSQC.	
@PNSQC	
#PNSQC19
•  Senior	leaders	of	project-based	organizations	
•  Discuss	common	problems	and	solutions	in	project	
portfolio	management	and	project	office	governance	
•  From	a	wide	spectrum	of	commercial	industries,	
government	agencies,	and	not-for-profit	organizations	
•  Contact	Jeff	Oltmann,	jeff@spspro.com	
@philiplew	@pnsqc	
2
PNSQC	
Pacific	Northwest	Software	Quality	Conference	
•  The	oldest	software	quality	conference	in	North	America	
now	in	its	37th	year.	
•  Annual	conference	held	in	Portland,	Oregon	
•  Non-profit	organization	run	by	volunteers.	
•  PNSQC	is	a	hybrid	professional	conference	that	focuses	
on	the	software	quality	practitioner.		
•  Conference	speakers	and	participants	are	people	sharing	
their	own	experiences	in	both	success	and	failure	(not	by	
consultants	nor	vendors).		
•  A	range	of	topics	and	speakers	-	everything	from	
management	methods	and	distributed	teams	to	agile,	
automation,	Devops	and	security.	
3
Our	Speaker	Today	
Philip Lew
PNSQC Board Member, Program
Chair, and Speaker
• CEO, XBOSoft
• Relevant specialties and passions
o Software quality process,
evaluation, measurement and
improvement
o Software quality in use / UX design
o Mobile User Experience and
usability
o Cycling and travel
o He never learned how to read
4
Our Moderator Today
@philiplew	@pnsqc	
5	
Ying Ki Kwong
PNSQC Volunteer and Speaker
PPLF Member
•  Statewide QA Program Manager,
Office of the State CIO, State of Oregon
•  Relevant specialties and passions
o  Quality & risk management
o  Enterprise IT project management
o  Complex systems and complexity
o  Volunteering for local nonprofits
o  Travel
Background	for	Today	
§  At	PNSQC	2018,	Phil	&	Ying	Ki	presented	a	paper	on	
quality	&	risk	management,	from	the	perspective	of	
enterprises	acquiring	systems.	
§  https://www.pnsqc.org/quality-risk-management-challenges-when-
acquiring-enterprise-software-systems/	
§  Various	subjects	were	covered,	with	some	attention	on	
Agile.	
§  Feedback	received	about	the	community’s	need	for	
improved	general	understanding	around	where	Agile	
meets	enterprise	quality	&	risk	management.	
6	
So,	today’s	talk	by	Phil	co-sponsored	by	PPLG	and	PNSQC.
House	Rules	
§  Participants	other	than	the	speakers	are	muted	
§  Questions	via	the	Zoom	control	panel	or	through	
Twitter	@PNSQC	
§  Questions	may	be	asked	throughout	the	webinar	-	
we’ll	try	to	answer	them	at	the	end	
§  You	will	receive	info	on	recording	and	slides	after	
the	webinar	
7	Webinar	Hashtag:	#AgileRisk		
Now	the	featured	speaker...
Software	Quality	and	Risk	
Why	Are	We	Here	Today?	
• All	Companies	are	becoming	Software	
Companies	
• Software	is	becoming	a	significant	part	of	
almost	all	value	chains.		
• Technology	and	business	conditions	make	
consistently	providing	value	difficult	to	
accomplish	without	mitigating	large	amounts	
of	risk.	
@philiplew	@pnsqc	
8
Agenda	(1)	
Agile	
Risks	
Reasons	
for	
failure	
Agile	
process	
Risk	
types	
Uncertainty	
and	
probabilities	
9
Agenda	(2)	
Uncertainty	
and	
probabilities	
Distribution	
How	to	treat	risk	
based	on	probability	
distribution	
Impacts	
Lose	
money	
Lose	
customers	
10
What	Got	Us	Here	
•  Smaller	teams	
•  Faster	iterations	
•  Listening	to	the	user	
•  Continuous	beta	
•  Data	collection	&	analytics	
11	
•  Communication/Collaboration	
•  Full	stack	teams	
•  Retrospectives	
•  Analysis,	adaption	and	
improvement	
1.  Changes	in	technology	(mobile,	cloud)	
2.  Changes	in	business	models	
3.  Many	failures…	
@philiplew	@pnsqc
Agile	and	Risk	
•  Chasing	agility	and	velocity	à	ignore	
risks	inherently	introduced	by	Agile	
•  Mistake	completed	sprints	for	
progress	
•  Velocity	attained	but...	Still	don’t	
deliver	what	is	wanted	and	needed	
(MVP).	
•  Backlog	mismanagement	
•  User	stories	(especially	for	complex	
features)	not	detailed	enough	for	
management	to	ascertain	that	
features-functions	will	meet	
business	needs.	
•  Hard	to	implement,	yet	critical	or	
complex	features	not	implemented	
(stay	delayed	in	backlog)	or	
incorrectly	implemented.	
@philiplew	@pnsqc	
12
13	
One	of	the	Main	Agile	Flavors	:	Scrum	
1	 2	
3	
@philiplew	@pnsqc
Agile	
Problems	
Resistance	
to	Change	
DIstrust	
Requirements	
Churn	
Frozen	
Requirements	
Agile	Doing	–	
Not	Being	
Process	
Inconsistency	
Lack	Test	
Automation	
Retrospectives	
Not	Valuable	
AgileFall	
Lack	Customer-
User	
Understanding	
Agile	Failures	–	Why?	
14	
Let’s	Vote	–	You	get	to	pick	the	top	3	
Maybe	you	have	another	reason?	
@philiplew	@pnsqc
“RISKFUL	THINKING”	
Where	does	it	comes	from?	
@philiplew	@pnsqc	
15
Exercise:	Mapping	Risks	(small	groups)	
	
	
16	
@philiplew	@pnsqc	
People
ProductProcess
Partners
The	Realm	of	Software	Project	Risks	
Personnel	Shortfalls	
Shortfalls	in	
external	
components	&	
services	
Real-time	
performance	
shortfalls	
Straining	Computer	
Science	capabilities	
User	can’t	use	it	
Gold	Plating	
Developing	the	wrong	
features-wrong	thing	
Unrealistic	
schedules	
Unrealistic	budget	
Stream	of	changing	
requirements	
Software	Risk	Management,	B.	Boehm	1989	
People
ProductProcess
17	
Security	holes	
@philiplew	@pnsqc	
Partners
Risk	Types	
Risk	Technology	
Product	
Process	
People	 Context	
Delivery	
Business	
Customers	
@philiplew	@pnsqc	
18
Technology	Risks	
•  Platform	can’t	adapt	to	changing	needs	
•  Too	hard	to	implement,	too	complicated	with	current	
technology	stack	
•  Doesn’t	integrate	well	with	other	3rd	party	tools	
•  Can’t	find	people	who	have	the	right	skills	
•  What	else	in	terms	of	technology	risks?	
	
@philiplew	@pnsqc	
19
Product	Risks	
•  Delivered too late, 1st mover or even 2nd mover
advantage dissipated
•  Doesn’t do what the customer/user wants
•  We missed the mark, it does what we wanted
but…
•  Too slow
•  Harder to do than we thought
•  Can’t deliver sought after/differentiator features/
functions
•  “Move it to the backlog for now…”
•  ______	
@philiplew	@pnsqc	
20
Process	Risks	
•  Too slow
•  Not repeatable
•  Delicate and FrAgile – Easily broken
•  Not adaptable
•  Not consistent
•  Too dependent on a superhero
@philiplew	@pnsqc	
21
TYPICAL	RISK	MGMT	
EVENT	X	PROBABILITY	=	IMPACT	
Seems	that	Everything	is	a	Risk!	Not	
all	risks	are	the	same.	
@philiplew	@pnsqc	
22
Let’s	Talk	About	Probability	
• Most	of	us	subconsciously	assume	a	
normal	distribution	when	it	comes	to	
uncertainty	
• That	is	what	we	are	used	to	when	we	
were	given	grades	in	school,	
remember?	
• But	what	are	the	characteristics	of	a	
normal	distribution?	
@philiplew	@pnsqc
Grades	in	School	
@philiplew	@pnsqc	 24
Fat	and	Narrow	Tails	Make	a	Difference	
•  What	risks	are	fat	
and	narrow	tailed?		
•  With	a	fat	tailed	
risk	you	can	be	
catastrophically	
wrong.	
•  What	would	be	
“Ruin”	when	it	
comes	to	software	
development?	
	
@philiplew	@pnsqc
Why	It’s	Important	to	
Understand	Normal	and	Fat	
•  Traditional	risk	management	strategies	rely	on	
and	assume	a	normal	bell	curve	but	in	reality,	
projects	don't	behave	this	way.		
•  What	things	are	normal	and	what	types	of	
occurrences	are	not	normal	(don’t	conform	to	
normal	distribution)?	
•  Height	of	people	in	the	room	
@philiplew	@pnsqc	
26
Normal	Exercise	–	Entire	Class	
•  Normal	distributions	vary	in	the	neighborhood	of	
its	average,	but	have	very	few	data	points	
beyond	3	standard	deviations	from	that	average.	
•  Do	a	survey	of	the	class	and	calculate	the	
average	height	of	people	in	the	room	for	men,	
and	for	women.		
•  Average	height	of	men	is	5’10”	with	standard	
deviation	of	4”.	
•  3	standard	deviations	-	Chances	of	a	6’10”	man	
are	very	small.	
@philiplew	@pnsqc	
27
Fat	Tail	Exercise	–	Small	
Groups	
•  http://www.boxofficemojo.com/genres/chart/?
id=documentary.htm	
•  Calculate	the	average	and	standard	deviation	for	
these	documentary	movies	revenue.	
•  What	are	the	differences	you	observe	between	
documentary	movies	and	people’s	heights?	
•  How	can	you	apply	this	to	your	work	in	
determining	what	is	a	risk	and	not,	what	risks	to	
pay	attention	to	and	NOT.	
@philiplew	@pnsqc	
28	
average	 	$11,393,365.45		
standard	deviation	 	$17,319,262.05
In	the	End,	We	Want	to	
•  Find	problems	early	
•  Find	big	problems	
•  Avoid	problems	altogether	
•  **Problems	by	nature	have	negative	
consequences	
•  Our	job	is	to	decrease	this	probability	
•  Agile	helps	us	with	this,	but	we	need	to	focus	on	
those	activities	with	the	right	viewpoint	to	gain	
this	insight	
@philiplew	@pnsqc	 29
Why	is	Probability	Important?	
• It	changes	the	whole	conversation	
• “When	can	you	get	this	done?”	
• “Depends	on	how	much	risk	and	
certainty	you	want”	
• What	other	questions	does	your	boss	
ask	that	should	be	answered	with	a	
probability?	
30	@philiplew	@pnsqc
•  Software	is	increasingly	componentized,	
complex	and	distributed	à	hidden	risks.	
•  Development	frameworks	ease	complexity	in	
creating	software,	but	are	limited	in	helping	test	
the	applications.	
•  Organizations	want	to	reduce	maintenance	costs	
while	shortening	project	life	cycles	via	agile	
practices.	Faster	is	not	safer…	
•  Risk	is	not	decreasing,	nor	is	the	risk	of	
catastrophe.	
@philiplew	@pnsqc	
31	
Risks	Are	Not	In	Our	Favor
Why	Do	We	Ignore	or	Forget	
Risks	
1.  Focused	on	velocity	
2.  Focused	on	functionality	
•  Do	the	easy	stuff	first	
3.  Risk	management	is	too	heavy	
4.  Known	or	identified	risks	but	no	action	
Why	do	you	forget	or	ignore	risks?	
@philiplew	@pnsqc	
32
Overconfidence	is	Natural	
•  We	are	naturally	overconfident	(cognitive	bias)	
•  Optimistic	bias	leads	us	to	take	risks	and	underestimate	
the	odds	we	face	
•  80%	of	small	businesses	fail	in	the	first	18	months	
according	to	Forbes	
•  Surveys	indicate	that	entrepreneurs	give	themselves	a	
60%	chance	of	success	
•  To	what	extent	will	the	outcome	depend	on	what	you	
do?	–	80%	
@philiplew	@pnsqc	
33
Tendency	to	Only	See	Readily	
‘Available’	or	Latest	Evidence	
•  Social	and	economic	pressures	favor	
overconfidence	
•  We	tend	to	have	an	illusion	of	control	
•  When	we	estimate	a	quantity,	we	rely	on	
information	that	comes	to	mind		
•  We	need	to	allow	for	the	information	that	
does	not	come	to	mind!	
•  We	weight	evidence	of	most	recent	
experiences	more	than	we	should.	
•  We	want	to	believe	and	make	ourselves	right.	
@philiplew	@pnsqc	
34
Premortem	
•  To	overcome	this	overconfident	optimistic	
cognitive	bias,	we	can	use	a	premortem.		
•  Enables	those	who	had	any	concern	about	the	
project	can	freely	mention	the	concerns.	
•  Great	safeguard	against	groupthink.	
•  Give	team	members	‘permission’	to	be	a	
pessimist.	
@philiplew	@pnsqc	
35	
1.  Imagine	that	a	year	has	passed.	
2.  Your	project	has	been	shown	to	be	an	utter	disaster		
3.  Briefly	explain	(write)	why	it	was	a	disaster.
RISK	WITHIN	AN	AGILE	PROCESS	
Let’s	address	risks	within	the	agile	
process.	You’ll	find	that	an	Agile	
approach	inherently	lets	you	identify	and	
manage	risks.	
@philiplew	@pnsqc	
36
Risks	During	Agile	
Exercise	(or	Not):	List	out	risks	that	you	may	encounter;	
what	could	go	wrong	during	each	phase?	
1.  During	the	beginning-planning		&	product	management	
2.  During	the	sprint	
3.  During	the	retrospective	
@philiplew	@pnsqc	
37	
Break	up	in	small	groups	and	list	out	the	risks
Product	Management	(1)	
Risk	 Mitigation	
Delivery	delay	 •  Drive	towards	estimating	accurately.	
•  Align	expectations	and	what	can	and	cannot	be	
delivered	in	planning	meeting.	
•  Reduce/manage	expectations.	
Even	though	the	application	
works,	it	doesn’t	work	as	it	
was	intended	to	do.	
Review	backlog	user	stories	to	ensure	you	
understand	them	fully.		
Scope	creep	 Evaluate	existing	backlog,	new	items,	add/delete	
and	trade	out.	
Personnel	loss	 Ensure	full	stack	team	with	cross	disciplinary	skills	
Forgotten	or	overlooked	risk	 When	developing	the	backlog	explicitly	ask	to	
identify	the	potential	problems.		
@philiplew	@pnsqc	
38
Product	Management	(2)	
Risk	 Mitigation	
Application	hard	
to	maintain	and	
adapt	to	changing	
business	
requirements-	
poor	underlying	
structure	and	
architecture	
In	the	sprint	planning	meeting	cover	more	than	what	is	
immediate	(to	do).	
•  How	will	this	feature	be	implemented	within	our	
existing	architecture?	
•  Are	our	estimates	the	‘quick	and	dirty’	method	
(increasing	debt)	or	can	we	do	it	a	better	way?	
	
Forgotten	or	
overlooked	
•  Interview	those	that	are	not	part	of	the	planning	
exercise.		
•  Identify	the	knowable	risks	when	generating	the	initial	
backlog.		
•  Build	mitigation	for	risks	into	the	definition	of	done.		
•  Generate	stories	for	risks	and	add	them	to	the	backlog.		
•  Specifically	allocate	time	during	planning	to	identify	
emerging	risks.	
@philiplew	@pnsqc	
39
Risk	 Mitigation	
Planning	takes	too	much	time	
and	therefore	doesn’t	get	
done,	or	done	well/
completely.	
•  Ensure	a	clear	prioritization	process	
•  Ensure	that	planning	and	grooming	sessions	
have	clear	output	
Estimation	process	is	not	
clear,	not	standard	and	not	
oriented	toward	improvement	
	
•  Ensure	clear	acceptance	criteria	within	the	user	
story	and	the	definition	of	done.	
Stakeholders	say,	“I	didn’t	
know	that”	or	don’t	officially	
‘approve’.	
•  Develop	guidelines	for	documentation,	tracking	
and	reporting	to	allow	visibility	and	
transparency	of	all	project	aspects	
Delays	due	to	who	decides	as	
the	ultimate	authority	on	a	
feature-or	other	decision	
•  Setup	guidelines	for	agile	decision	making.	
Product	Management	(3)	
@philiplew	@pnsqc	
40
Sprint	(1)	
Risk	 Mitigation	
•  Testing	incomplete,	or	
rushed	at	the	end	
•  Implement	test	driven	development	
•  Include	testing	in	the	definition	of	done	
•  Demonstrations	at	the	end	
of	the	sprint	not	conclusive	
(done	or	not?)	
•  Insufficient	integration,	or	
integration	too	late	
•  Review	stories	to	ensure	acceptance	criteria	are	
clear	
•  Definition	of	done	includes	testing	and	
integration	
•  API	automated	testing	
•  We	deliver	product	and	find	
out	we	have	some	security	
and	performance	issues	
which	require	architectural	
changes.	
•  Worsening	performance	
•  Define	measurements	for	many	viewpoints	on	
improvement,	not	just	velocity.		
•  Periodically	test	non	functional	requirements	as	
part	of	definition	of	done.	
•  Include	performance	criteria	in	definition	of	done	
•  Implement	performance	testing	criteria	and	
scenario	testing	for	most	common	user	scenarios	
@philiplew	@pnsqc	
41
Sprint	(2)	
Risk	 Mitigation	
•  Poor	quality	of	a	
delivered	application.	
Even	though	the	
application	works,	it	
doesn’t	work	as	well	as	
it	should	(i.e.	usability,	
security,	
performance).	
•  Cannot	fulfill	what	it	
was	intended	to	do.	
	
Definition	of	done	includes	some	level	of	
predefined	non-functional	testing,	where	
comparisons	are	done	including:	
•  Code	reviews	
•  Heuristic	and	observational	usability	
testing	before	its	“Done”	and	too	late.	
	
@philiplew	@pnsqc	
42
Risk	 Mitigation-Items	to	Examine	
Risks	forgotten	or	unknown	 •  Gather	risk	data	though	surveys	when	the	program	
stakeholders	are	geographically	diverse.		
•  Interview	customers	or	potential	customers.		
Feature	turned	out	too	
hard	to	implement	or	took	
too	much	time	
Ask	these	questions:	
•  How	was	the	feature	implemented?	Did	we	make	it	
harder	than	we	needed	to?	
•  Did	we	make	any	architecture	decisions	from	before	
that	impeded	this	feature	
•  Is	the	underlying	structure	and	architecture	able	to	
meet	future	needs	
	
Scope	creep	 Examine	unplanned	work,	check	estimates	
Personnel	loss	 Review	issues	created	due	to	lack	of	skills	or	people	
Retrospective	(1)	
@philiplew	@pnsqc	
43
Risk	 Mitigation	
Delivered	what	we	could,	
but	did	a	work	around	
•  Examine	existing	architecture	
Too	difficult	to	implement	a	
function,	took	much	longer	
than	we	thought	
•  Walkthrough	design	considerations	on	
periodic	basis	
•  Assess	team	skills	
•  Ensure	clear	definition	of	done	
•  For	tough	features,	increase	collaboration	
regarding	detailed	design	
•  Examine	estimating	errors	
Integration	too	late,	
product	didn’t	work	
together,	just	pieces	
	
•  Define	and	implement	continuous	
integration	process	
•  Integrate	daily	
Retrospective	(2)	
@philiplew	@pnsqc	
44
Risk	 Mitigation	
Lack	of	performance,	load	
and	security	testing	until	the	
end	
Build	in	non-functional	testing	as	a	user	
story	for	periodic	execution,	i.e.	once/
month	
	
•  Didn’t	get	‘Done’	
•  Customer	not	satisfied	
with	the	feature	although	
we	did	what	he	said/in	
the	user	story	
	
•  Review	user	stories	for	ambiguity	and	
completeness	
•  Ambiguous	assumptions	and	
responsibilities		
•  User	stories’	done	criteria	insufficient	
•  User	stories	too	big	
Too	much	stuff	in	the	sprint,	
didn’t	finish,	many	things	
added	in	during	the	sprint	
Define	method	and	logic	to	add/subtract	
from	the	sprint	during	the	sprint	
	
Retrospective	(3)	
@philiplew	@pnsqc	
45
Risk	 Mitigation	
Retrospective	not	
productive	
•  Led	by	an	independent	facilitator,	could	
be	another	team	or	executive	
•  Held	in	a	safe	place	–quiet,	not	
disturbed	
•  Not	a	witch	hunt	–Focus	on	process	
rather	than	people	
•  Plan	the	event	–send	out	notes	on	
potential	problems	to	get	people	
thinking	
•  Have	the	right	people	involved	
•  Record	results	in	open	area,	allocate	
and	monitor	actions	
Retrospective	(4)	
@philiplew	@pnsqc	
46
Retrospective	(5)	
Risk	 Mitigation	
Confusion	of	roles	and	
responsibilities,	
something	is	forgotten	
or	falls	off	the	plate	that	
was	important	
•  Instill	Primary	ownership,	even	with	2	
team-mates	
•  Analyze	items	that	fell	off	previously	to	
determine	estimation	errors	
•  Examine	all	unplanned	work-
Necessary?	
Time	crunch	at	the	end,	
not	enough	time	to	get	
done	
•  Instill	in	daily	standups	-	address	delays	
Can’t	deliver	what	we	
thought,	too	complex	or	
we	didn’t	understand	
well	enough	
•  Daily	standups	address	estimated	
points	for	a	story,	re-assess	and	split	
up	
•  For	increased	story	points,	product	
owner	feedback	required	
@philiplew	@pnsqc	
47
At	the	“End	of	the	Day”	
Risks	 Own	
Agree	
and	
accept	to	
do	
nothing	
Eliminated	
or	
avoided	
Probability	
or	impact	
reduced	
Mitigate	
@philiplew	@pnsqc	
48
Manage	Risk	With	The	End	in	Mind	
Software	Quality	
@philiplew	@pnsqc	
49	
“It’s	not	enough	
to	do	your	best;	
you	must	know	
what	to	do	and	
then	do	your	
best.”	
W.	Edwards	Deming
Join	Us	This	Fall	#PNSQC19	
Submit	an	Abstract	today	at	pnsqc.org	
	
	
www.pnsqc.org	
Today’s	webinar	has	been	recorded	and	will	be	available	via	the	
PNSQC	Youtube	Channel.		
@PNSQC	
#PNSQC19	
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and	
Answers

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