Managing Dilemmas
By Geoff Ball and Jerry Talley, Edgewise Consulting
Managing Dilemmas focuses on on-going approaches that maximize the
benefits of both sides of a dilemma while minimizing the drawbacks of
pursuing either side alone.
“A visionary company doesn’t seek to balance between short-term and long-term. It seeks to do very well in the
short term and very well in the long term… it doesn’t simply balance between a tightly held core ideology and
stimulating vigorous change and movement; it does both to an extreme….Rare? Yes. Difficult? Absolutely. But
as F. Scott Fitzgerald pointed out, ‘The test of a first-rate intelligence is the ability to hold two opposed ideas in
the mind at the same time and still retain the ability to function.,’ This is exactly what the visionary companies
are able to do.”
--Built to Last, James C. Collins and Jerry I. Porras.
A dilemma is a pair of apparently contradictory goals both of which are valuable to
the organization. These goals are in tension – moving one goal ‘up’ tends to move
the other goal ‘down.’
Dilemmas and Conflicts
Poorly managed dilemmas lead to conflicts. These conflicts are familiar to most
executives and managers. Audiences respond to their familiarity and acknowledge
the conflict that it causes in their organizations. When poorly managed dilemmas
sound like this:
CEO: How do I take on more staff costs when our biggest sale is about to collapse on
us?
SALES: (To Eng) You know, if you stopped adding features that our
customers don't want, maybe you could get the configuration right in
time? Did you ever think of that?
ENG: Those "extraneous features" are our future. You just sell single
installations. We have to design a next generation product. And that's how
we're going to get tomorrow's customers. Not to mention tomorrow's
engineers.
SALES: (To Eng) I just wish you'd pay a little more attention to today's
customers. They're the ones paying our salaries.
CEO: Well, neither one of you are going to be drawing a salary if we don't sort this
out. I'm tired of having these conversations with you two guys. I'm going to call Bob
back and see if I can buy you two clowns some time. And I want this resolved by the
533569133 2/17/16 5:38 AM Page 1
end of the week.
We believe that some 25-50% of all organizational conflict is caused by
unacknowledged and unmanaged dilemmas. In this role play we hear blaming,
whining, finger pointing, and threats – but no positive acknowledgement of the
ways these goals are connected together – even when the connections are pointed
out by the participants themselves.
Unmanaged dilemmas tend to fuel interpersonal conflicts and heighten
interdepartmental friction. People caught up in dilemmas are likely to pull at each
other, even yell at each other, without being aware that they are caught on the horns
of a dilemma. They feel that some other group in the organization routinely
undermines their best efforts. Yet, their own good efforts often lead to someone
else's setback and pain.
People often experience dilemmas as a forced choice – they must choose one goal or
the other, as if they are polar opposites.
Yet, we believe that maximum
organizational performance is created
when dilemmas are considered a single
focus, rather than separate goals. Since
both sides of a dilemma are valuable and
necessary, we don’t want to sacrifice one
for the other. (What company can
continuously avoid longer-term
investments to secure short-term profits?
Or visa-versa?). This thought is shown in
the graphic to the right. When the
situation is characterized along a line, we
think in polarities and opposites. When we
bend the line, we see the possibility of pursuing both goals by managing the
dilemma.
Managing Dilemmas for Competitive Advantage
Organizational dilemmas are easy to find; yet, successful management of these
dilemmas is rare. Exceptional management of dilemmas leads to significant
competitive advantage and to reduction of unproductive organizational conflict.
The cost of poorly managed dilemmas can be high. For example:
 Time spent arguing with other departments to no useful end.
 Reduced productivity from lowered morale
 Workers feeling unappreciated
533569133 2/17/16 5:38 AM Page 2
 Departments take unilateral action that leads to confusion and rework and
resentment
 Appear disorganized to the customers
 Lost sales and lost referrals
And there is a prize if we do manage dilemmas well:
 Synergy of efforts between departments
 Leapfrog the competition with breakthrough ideas and products
 High customer satisfaction for high quality work done on time
Here are major examples of successful dilemmas thinking.
Consider the dilemma: [Lowered cost /\ Higher quality]* in the context of health
care:
Managing the costs of health care has been problematic, political and frustrating to
all who have attempted it. Yet, in what appears to be a breakthrough – and what
seems to us an example of dilemmas thinking - Merrill Lynch has increased the
quality of health care and lowered costs over the last five years. The Wall Street
Journal article “Doctor Yes: How is Merrill Lynch limiting health costs by expanding
benefits,” May 23, 2000, reported that, “Adjusted for inflation, its health costs have
declined even while benefits have expanded…. Merrill says it saved money by
focusing on the quality of care and early detection.” The full article is fascinating.
Merrill Lynch has done the following:
1. Made a commitment to quality care
2. Allowed doctors to determine treatment
3. Focused on early detection, and
4. Applied risk management strategies and sophisticated tracking software to
health care
It appears to be working.
____________
*Footnote: The symbol ‘/\’ is our way of indicating that both sides (goals) of a
dilemma are equally valuable and essential for our organizations to succeed. It is
also the logical symbol for the conjunction of sets, which reflects our belief that the
only satisfying solution is to find a way to do both, despite the apparent conflict.. –
End Footnote
_____________
Consider the dilemma: [Low cost /\ high employee satisfaction] in the context of
transportation.
At a time when all airlines were offering pretty much the same type of service
Southwest Airlines created a different business plan. They focused on customers
533569133 2/17/16 5:38 AM Page 3
willing to accept less in areas not that important to those customers – no meal
service, no pre-assigned seating,. They limited other complexities by using only
737’s airplanes; by going to second tier airports; and by exercising great care in
selecting, training and indoctrinating their employees in the way Southwest works.
They have been the most consistent positive financial performer in the airline
business, with extremely good on-time records and employees that exhibit initiative
and the extra effort needed to keep costs low and customer satisfaction high. While
we doubt that they explicitly used dilemmas thinking, we do believe that implicitly
they followed its precepts.
Dilemmas thinking allows us to focus on this struggle. People learn that the conflict
is inherent in the goals of the organization, not between the people. We seek to shift
conflict into mutually beneficial dialog and innovative high performance. Fletcher
and Olwyler, Paradoxical Thinking, point out that with a paradoxical (dilemmas)
framework* the conversations between coworkers become much more open, more
productive, and that hidden issues are talked about productively with minimal
blame and maximum insight into ways to manage the dilemmas that confront every
business. We face the dilemma together rather than confronting each other as
persons. This process of thinking together enriches everyone’s understandings of the
linkages between actions across the dilemma.1
Charles Handy, in The Age of Pardox, argues, “We have no chance of managing the
paradoxes (dilemmas) if we are not prepared to give up something, if we are not
willing to bet on the future, and if we cannot find it in ourselves to take a risk on
people. … Most of the dilemmas that we face in this time of confusion are not the
straightforward ones of choosing between right and wrong, where compromise
would , indeed, be weakness, but the much more complicated dilemmas of right and
right. …We want to be good corporate citizens and return a decent profit; we want
to trust our subordinates but we need to know what they are doing.”
Outcomes and their supports
Managing dilemmas seeks to achieve two outcomes:
1. Limiting the damage: This negotiated set of limits, indicators and parameters
constrain the immediate damage caused by excess zeal in pursuing one goal at
the cost of the other goal and by narrow thinking.
2. Managing towards maximal resolutions for the dilemma: We seek specific
actions and behaviors that enable high performance on BOTH sides of the
Three words are often used relatively interchangeably – paradox, dilemmas and
polarities. We have somewhat arbitrarily chosen the word dilemma.
1
533569133 2/17/16 5:38 AM Page 4
dilemma. Since that requires continuing oversight, we focus on 'managing' the
dilemma rather than 'solving' it.
Work on dilemmas must be supported by:
3. Building strong working relationships: These enable people tasked with
different sides of the dilemma to explore jointly both sides of the dilemma for
their mutual benefit. And effective dilemmas management strengthens working
relationships.
4. Creating Shared Mental Maps and Representations: These enable us to see
dilemmas clearly, think about dilemmas powerfullly and manage them through
time. The fact that they are shared greatly facilitates communication. Knowing
generic classes of dilemmas enables us to catalogue strategies for consideration
in a specific situation.
Dilemmas thinking requires the following mindsets:
 Avoiding excesses; we agree not undermine each other.
 Knowing that how we think is as important as the specifics we consider.
 Seeking to truly understand the experience of those "on the other side.”
 Believing that dilemmas thinking can lead to superior performance
Organizational Helps and Hinders
We are helped or hindered in managing dilemmas by interpersonal, structural and
cultural characteristics of our organizations. The following characteristics hinder
managing dilemmas:
HINDERS
How we deal with
Interpersonal attitudes Structural
Cultural
CONFLICT
Push it upstairs
Subordinates are NOT
empowered to address
cross boundary issues
Conflict is handled, if
at all, at higher levels
BOUNDARIES
“Keep off my turf”
Strict organizational
boundaries. A unit can
take action within its
boundaries without
consulting or even
informing others.
Controlled information
GOALS
I pay attention to MY
goals
Management by
objectives
Narrow focus on what
I / my unit is
responsible for
533569133 2/17/16 5:38 AM Page 5
REWARDS
Do what I need to to
get my rewards
Incentives focus on
individual
performance
ROLES &
DUTIES
My way of the
highway
Rules and duties define
the totality of the work
There is one right way.
Keeping order and
maintaining discipline
is paramount
These characteristics severely limit the ability of the organization to manage
dilemmas that transcend organizational boundaries. Yet, they tend to be what we do
‘naturally’ since they have been successfully used in traditional organizations and
are often taught as the cornerstones of good management. Conscious effort will be
needed to revisit and rethink these precepts.
The following characteristics help in managing dilemmas:
HELPS
How we deal with
Interpersonal attitudes Structural
Cultural
CONFLICT
We can work it out
between us at this level
Cross boundary
disputes are addressed
by those involved,
Everyone is expected
to work through
interdepartmental
conflicts.
BOUNDARIES
Welcome. We
appreciate your
interest
Permeable
organizational
boundaries.
Shared information
where that is helpful.
Conversations across
boundaries;
GOALS
Tu goals es mi goals. I
keep in mind the
impacts of my actions
on other’s goals.
Individual, team and
process goals
Goals include mine up
to the organizational
goals
REWARDS
I know that working
with others will be
rewarded
Formal incentives
support working
together.
We truly are a team
and individual
performers both
ROLES &
DUTIES
Open to seeing others
perspectives
I have a balance of
work defined by roles
and duties and space
where I use my
judgment.
533569133 2/17/16 5:38 AM Page 6
While recent books have suggested the importance of developing these helpful
conditions, the more common conditions are those in the hinders table.
Business executives often recognize that they have dilemmas, though they may not
name them. However, too often the recognition leads to “Oh well, that’s just
business.” Or “You just have to choose what you are going to make your priority.”
While some companies do manage dilemmas well, many do not. What we are
proposing is more conscious thought on managing dilemmas.
One excellent resource is Barry Johnson’s work on ‘polarities’. See his website,
http://www.polaritymanagement.com/ One tool he developed about 1975 uses a
Polarity Table to surface the ‘racetrack’ dynamics of dilemmas, and then to press for
approaches that move toward both of the goals contained within the dilemma. He
published a highly rated book Polarity Management: Identifying and Managing
Unsolvable Problems, 1997. One reader stated, “Johnson provides us with a
framework to understand the nature of dilemmas. Easy to read, the simplicity of
Polarity Management belies its explanatory power in handling paradox and in so
doing transforms our view of dealing with difficulties. This book is an important
and satisfying read that does provide the reader with a genuinely new paradigm in
thinking rare in these days of over-hyped publications.” And another, “Johnson
shares great truths needed today. I cannot imagine how this book has remained the
best-kept secret in management and systems thinking.”
In what follows we provide responses to that question first in terms of five phases
and secondly in terms of six approaches & eight tools.
Five Phases for Managing Dilemmas
Phase
Outcome
1. Assess the situation from a dilemmas
perspective
Determination that there is a
dilemma to be managed
2. Agree to share responsibility for this
dilemma
Agreement by key parties to
partner in managing the dilemma
3. Understand the dilemma
Deep understanding of the
dynamics and the connections of
the dilemma
4. Find approaches to manage the
dilemma
Specific actions to take and
commitment to take them
5. Create and monitor dilemma
boundary indicators
Indicators and monitoring system
that will show when minimums are
approached or crossed
533569133 2/17/16 5:38 AM Page 7
Approaches to managing dilemmas
1. Search Generic Dilemmas Database for possible solutions
About 15 generic types of dilemmas are sufficient to categorize most of the
specific dilemmas we have found. We are currently searching out strategies for
managing specific dilemmas within each of these classes. By reviewing this
database team members may find suggestions for specific approaches that will
work for them.
2. Create incentives and structures that motivate and enable management of the dilemma by
participants
Instead of creating a planning team to develop strategies, create an action team
with incentives aligned with managing the dilemma. For example, both sales and
engineering are both responsible for both goals. Remove as many of the
‘hinders’ as possible and create the ‘helps.’ Encourage the team to invent
strategies as they work.
3. Challenge the mind through oxymorons and progressive improvement
Make use of the oxymoron approach in Paradoxical Thinking by Fletcher and
Olwyler. Make use of the tools mentioned below in support of the dilemmas
management team.
4. Map the connections between the sides of the dilemma; relax these constraints; transcend
boundaries and make boundaries permeable
Use a variety of the tools below to find and display the connections between the
goals. For example:
1. List activities to maximize each goal WITHOUT regard for the other goal.
Work together to see what could be done to really ‘go for the gold.’ Do this
for each of the goals independent of constraints. This exercise makes it easier
to see connections and constraints.
2. Ask participants specifically where they feel the pain in the other goal when
the first goal is maximized.
3. Map the role play dialog as it reveals connections.
4. Seek ways to get around or modify the connections to enable maximization of
both goals.
5. Identify actions that can be independently taken in the service of one side
without negatively impacting the other side of the dilemma.
533569133 2/17/16 5:38 AM Page 8
6. Creativity exercises focused on maximizing both goals’ maximums
Identify maximal resolutions for both goals. Search directly for these resolutions.
Brainstorm strategies for each and then brainstorm modifications so that the
resolution works for both goals. (Use the rich variety of creativity-enhancing
tools that are known.)
7. Duality meditations
Eastern traditions consistently focus on the duality of things – the most common
symbol of this being that of yin and yang. Approaches and mindsets from those
traditions can be used to enable the searcher to hold both sides of the dilemma in
their mind simultaneously and then let the mind find resolutions intuitively.
Tools that support Managing Dilemmas
 Group process tools: Brainstorming, countering, NLP “Parts Party”, “Go for the
Gold”, work through the TWWB’s - the “That Won’t Work Becauses ..;
 Graphics: graphic wall charts, images, pictures, video
 Maps & Representations: Linkage charts, Fletcher’s pendulum, flow charts,
linkage plots, loop diagrams, Johnson’s Polarity Table mentioned above, process
maps with organizational boundaries drawn in,
 Activities: Model construction, role plays with role reversals,
 Word plays:, Oxymorons, metaphors & analogies, ‘ing’ words, splitting multidefinitional abstract words, jokes & humor,
 Histories & Lessons Learned: Generic Dilemma Database, Pilot Projects,
 Broad strategies: Getting to Yes & Interest based Bargaining; Risk management;
Fuzzy Logic; Triad-based Systems, Process Improvement & Re-engineering.
Principles
We believe in the following key principles for managing a dilemma:
1. Make dilemmas visible and felt; name them.
2. Maintain a dilemmas mindset that leads to sharing and visibility across
permeable boundaries
3. Build powerfully collaborative working relationships
4. Construct reward systems and organizational structures that support managing
the dilemmas
533569133 2/17/16 5:38 AM Page 9
5. Avoid unconscious habits that make things worse – escalation of conflict, power
plays rather than working dilemmas through, oscillation of emphasis between
the two goals
6. Learn from past cases and situations; by generic naming of types of dilemmas it
becomes possible to aggregate experience more easily.
7. Avoid turning everything into a dilemma – useful as it is, dilemmas thinking can
be used to avoid making necessary hard choices.
533569133 2/17/16 5:38 AM Page 10
Example
In the following example we continue the travails of Bob Reynolds, CEO, his VP of
Sales (Joe) and VP of Engineering (Mike) introduced in the element, Dilemmas in
our Goals.
Let’s assume for this example that Joe and Mike – instead of following their usual
pattern of complaining to their staffs and anyone else who would listen about each
other – wound up right after Bob’s meeting having lunch with Susan, their director
of HR. Susan, sensing the tension between them, began to explore what had
happened. This time Joe and Mike began to complain about Bob and the untenable
situation they were in.
Fortunately, Susan had just been to a seminar on Dilemmas Thinking. After listening
in some detail to each of them in turn, she described the Dilemmas Thinking
approach to managing this kind of situation.
As a consequence of this conversation Joe and Mike embarked on an effort to apply
Dilemmas Thinking to their situation. In order to keep this element to a reasonable
length we will highlight a few examples of the work that they did.
1. Assess the situation from a dilemmas perspective
They identified specific situations in which their own goals were in tension; where
efforts by one led to pain for the other. They selected one specific situation that
seemed rich enough in detail to provide a lot of insight into their dilemma.
They described the two primary ‘competing’ goals as:
1. We sell the product that brings in revenue that keeps the company going (Sales)
2. We have a quality product that can be delivered on time and in working
condition that continues to sell. (Engineering)
2. Agree to share responsibility for this dilemma
They answered the two key questions affirmatively to ensure they were dealing
with a dilemma:
1. Both goals are essential to company success.
2. The two goals interact in ways that moving toward one goal without
considering the other makes moving toward that other goal more difficult.
And they agreed, for the first time, that they actually could help each other if they
worked together effectively. They would strive for mutual respect, open
communication and trust building across boundaries. Joe and Mike agreed that this
would be achievable over time. There was currently too much bad blood based on
past history to simply announce that the two departments were partners and have it
believed by anyone. So they strategized a series of small confidence building steps –
kind of like they were two warring nations trying to build a peaceful relationship.
533569133 2/17/16 5:38 AM Page 11
One such step was their agreement to publicly agree with Bob that they both needed
to find a way to both meet the market needs and to have products that worked as
sold and on time.
They also agreed with each other on the two essential outcomes of Dilemma
Thinking:
1. Maximal resolutions for both groups
2. Limited damage to the goals of one unit from the actions of another unit;
neither group below its minimums
3. Understand the dilemma
By using the Fletcher oxymoron process, they agreed on a powerful label for the
dilemma that would drive home the interconnections. In Paradoxical Thinking, Jerry
Fletcher lays out in considerable detail the sequence of questions and conceptual
foundation for the use of oxymorons – word combinations that drive the mind to
struggle with the inherent tension.
In this case Joe and Mike chose as their high performance oxymoron, ‘Responsive
products.’ Their nightmare oxymoron was, ‘Unsaleable engineering marvels.’
Joe and Mike worked with their staffs to understand the connections between the
goals. One department would suggest and action and the other department would
articulate where the pain was felt. In this way they were able to make the
connections between the goals explicit. For example, “giving in to clients on time of
delivery” linked to “training is inadequate because the system isn’t operating when
it is supposed to be.” They then sought ways to relax the constraints, and ease the
tension that the connections created.
4. Find approaches to manage the dilemma
Out of this they came up with a number of action items that could be implemented
to manage the dilemma more effectively. These included:
 Shifting the incentive system so that they both shared in the success of both
departments and both suffered when the other suffered.
 Engineering worked closely with sales in the meeting with clients. Using
modern teleconferencing equipment that could be brought into the client’s office
they were able to get the engineering expertise into the conversation, and it
helped the engineer understand what the sales engineer went through -- and all
with little additional engineering time required.
 Product launches where staged with the most critical unique functionality
coming early in the installation and less critical unique functionality spread out
in time, often over six months.
5. Create and monitor dilemma boundary indicators
533569133 2/17/16 5:38 AM Page 12
As Joe and Mike experienced success in their collaboration they grew more and
more comfortable with the notion of establishing indicators that signaled when
either department’s goals (now really joint goals) were in the yellow or approaching
the red zone.
The indicators for Sales were:
 Red:
 Percent of sales closed as a percent of serious clients falls below x
percent
 Strong negative perception of the company among potential clients.
 Yellow:
 Percent of clients complaining
The indicators for Engineering were:
 Red
 Percent of contracts not fulfilled on time.
 Percent of engineering time focussed on new product development
falls below y percent
 Yellow
 Percent of engineering time spent trouble shooting the installation
in order to get it up and running.
FINAL WORDS
While Joe and Mike are fictional, the situation portrayed is very common. Dilemmas
thinking and management can be a real service to an organization and to the people
working in them.
533569133 2/17/16 5:38 AM Page 13
Exercise
1. Assess your situation from a dilemmas perspective
 Do the exercises in Dilemmas in our Goals.
 Create a high performance oxymoron and a nightmare oxymoron. This results in
naming our dilemmas.
2. Agree to share responsibility for this dilemma
 Identify who would need to be involved in managing the dilemmas
 What would need to happen for that person or persons to agree to engage in
managing this dilemma?
 What working relationships would need to be improved?
3. Understand the dilemma
 Imagine the exercise in which one sided action that leads to pain for the other
side and identify two or three connections that could be relaxed to enable both
goals to be addressed more effectively.
4. Find approaches to manage the dilemma
 Based on the connections or your increased understanding of both dilemmas
invent actions that you could take to manage the dilemma.
5. Create and monitor dilemma boundary indicators
 Establish boundary indicators for both sides of the goal at both the yellow and
the red level.
 What would need to happen for everyone to agree to monitor and honor these
indicators.?
Now sit back and review your train of thought. What new insights or new
perspectives came out of dilemmas thinking. Where did you realize that you had
been attempting to do something like this but couldn’t articulate it well enough to
get a group of partners to do the work?
533569133 2/17/16 5:38 AM Page 14
Resource Books
(This list is from the list on Polarity Management Associates http://www.polaritymanagement.com/)
• Collins, James and Jerry Porras. Built to Last. New York: HarperCollins,
1993
• De Wit, Bob and Ron Meyer. Strategy Synthesis. London: Thompson
Learning, 1999
• Fletcher, Jerry and Kelle Olwyler. Paradoxical Thinking, How to Profit
from Your Contradictions. San Francisco: Berrett-Koehler, 1997
• Hampden-Turner, Charles and Alfons Trompenaars. The Seven Cultures of
Capitalism. New York: Doubleday, 1993
• Hampden-Turner, Charles and Alfons Trompenaars. Building CrossCultural Competence. Chichester: Wiley, 2000
• Hickman, Craig R. Mind of a Manager, Soul of a Leader. New York: John
Wiley & Sons, 1990
• Johnson, Barry. Polarity Management. Amherst: HRD Press, 1992, 1996
• Koestler, Arthur. Janus, A Summing Up. New York: Random House, 1979
• Kotter, John P. A Force for Change. New York: Macmillan, 1990
• Pascale, Richard T. Managing on the Edge. New York: Touchstone, 1990
• Quinn, Robert E. Beyond Rational Management. San Francisco: JosseyBass, 1988
533569133 2/17/16 5:38 AM Page 15