May 29, 2022 6 min read

Paradoxes of Leadership and Management

Leading and managing can be stressful and  frustrating because of inherent paradoxes built into the nature of the beast. One common mistake is not differentiating between paradoxes and problems.

What are these common paradoxes and how can we become more effective at navigating them?

Paradoxes are different from problems

A paradox is not a conflict within reality. It is a conflict between reality and your feeling of what reality “ought to be.”

— Richard Feynman

Problem-solving features prominently on almost all resumes, but in leadership it can in fact become a liability.

A common cause of frustration is the inability to differentiate between problems and paradoxes. This is especially true with leaders who come from a specialist or technical background. Their primary orientation is that of problem solving.

Problems by definition exist in a binary state — solved vs unsolved. They tend to have solutions but paradoxes don't. Instead, paradoxes are more on a spectrum of polarities where both opposites exist simultaneously and are not going anywhere — aka cannot be solved away.

The idea is not to avoid paradoxes but rather to engage with them and work within the constraints. Contrast that approach with treating them as an anomaly and getting frustrated by our inability to solve them.

So what are these paradoxes and can you recognize them beforehand? There are some common patterns that they fall under. Many sources of frustration in organizational setups can be traced upstream to one of these patterns.

Common paradoxes in leadership and management

Organizational life is complex. Knowing and recognizing paradoxes is a key skillset for leaders. Let's look at three lists of paradoxes I refer to most often.

In Being the Boss, Linda Hill and Kent Linebeck outline some key ones:

Direct Control vs Indirect Influence
(You are responsible for what others do.)

Work/Deliverables vs People/Meaning
(To focus on the work, you must focus on people doing the work.)

Support vs Judgement
(You must both develop your people and evaluate them.)

Group vs Individual
(You must make your group a cohesive team without losing sight of the individuals on it.)

Team vs Organization
(To manage your group, you must manage the larger context beyond your group.)

Urgent vs Important
(You must focus on today and tomorrow.)

Action vs Reflection
(You must execute and innovate.)

Inflicting pain vs Giving sustenance
(You must sometimes do harm in order to do a greater good.)

Your Team vs Your Organization
(Serving the sometimes conflicting needs of your team and the organization.)

Intimacy vs Distance
(Caring, even close, but focused on the work.)

Clarity/Answers vs Doubt/Questions
(The need to be clear—“here’s how we do what we do”—while remaining flexible in the midst of rapid change.)

Chaos vs Order
(Management and planning require both chaos and order.)

Us vs the Other
(Your personal success now requires that you find satisfaction in the success of those who work for you.)

Another useful list of paradoxes can be found in David Dotlich and Peter Cairo's The Unfinished Leader:

  • Long term (investments) versus short term (profitability)
  • Company versus function
  • Local versus global
  • Stability versus change
  • Hierarchy versus flat structure
  • Diversity versus meritocracy
  • Core growth versus innovation
  • Control versus delegation
  • Honoring people versus demanding performance
  • Work versus family

In his book Managing, Henry Mintzberg highlights how paradox is built into the nature of managerial work. He calls these conundrums of managing, and puts them poetically under the categories of thinking, information, people and action conundrums:

Thinking Conundrums:

  • The Syndrome of Superficiality - How to get in deep when there is so much pressure to get it done?
  • The Predicament of Planning - How to plan, strategize, just plain think, let alone think ahead, in such a hectic job?
  • The Labyrinth of Decomposition - Where to find synthesis in a world so decomposed by analysis?

Information Conundrums:

  • The Quandary of Connecting - How to keep informed when managing by its own nature removes the manager from the very things being managed?
  • The Dilemma of Delegating - How to delegate when so much of the relevant information is personal, oral, and often privileged?
  • The Mysteries of Measuring - How to manage it when you can’t rely on measuring it?

People Conundrums:

  • The Enigma of Order - How to bring order to the work of others when the work of managing is itself so disorderly?
  • The Paradox of Control - How to maintain the necessary state of controlled disorder when one’s own manager is imposing order?
  • The Clutch of Confidence - How to maintain a sufficient level of confidence without crossing over into arrogance?

Action Conundrums:

  • The Ambiguity of Acting - How to act decisively in a complicated, nuanced world?
  • The Riddle of Change - How to manage change when there is the need to maintain continuity?

Becoming more effective at navigating paradoxes

Given the universal nature of paradoxes in organizations and management, leaders can adopt four primary strategies to get better at navigating them:

  1. Changing how you view paradox
  2. Understanding and recognizing them
  3. Adjusting for predispositions
  4. Getting better at reflection

1. Changing how you view paradox

Mintzberg makes it plenty clear that paradoxes are not going anywhere and managers have to learn to navigate them instead of trying to wish them away:

These paradoxes and predicaments, labyrinths and riddles, are built into managerial work—they are managing—and there they shall remain. They can be alleviated but never eliminated, reconciled but never resolved. To try and escape them is to fall into the managerial dogma of which we have had more than enough already. Managers have to face them, understand them, reflect on them, play with them.

If you have a fundamentally problem solving orientation, not being able to solve something can be frustrating. Not realizing that these are part of the nature of the beast can lead to endless questioning and frustration.

Approaching paradoxes as conditions of the game rather than obstacles or problems to be removed, can change perspective and increase effectiveness in navigating them.

Many theories of organization emphasize either/or choices. They prescribe either stability and success, or instability and failure. They usually do not recognize paradox as fundamental and, when they do, they prescribe some kind of harmonious, equilibrium or balance between the choices. In this way the paradox is in effect eliminated; its existence is a nuisance that is not fundamental to success.
The way one perceives paradox says much about the way one understands organisational dynamics. The idea that, for success, paradoxes must be resolved, and that the tension they cause must be released or harnessed, is part of the paradigm that equates success with the dynamics of stability, regularity and predictability.

The notion that paradoxes can never be resolved, only lived with and explored, leads to a view of organisational dynamics couched in terms of continuing tension-generating behaviour patterns that are both regular and irregular, both stable and unstable and both predictable and unpredictable, all at the same time, but which lead to creative novelty.

– Ralph Stacey, Chris Mowles in Strategic Management and Organizational Dynamics

How do you define success? Is the absence of contradictions a key requirement? If it is, you might be setting yourself up for failure. In contrast, paradoxes and conflicts can be a rich source of creative ideas and innovation.

2. Understanding and recognizing paradox

As discussed before, understanding the differences between problems and paradoxes, and recognizing them beforehand can prevent a lot of undue frustration.

Revisiting the above lists on a regular basis can be a good way to identify patterns that needlessly hamper our efforts. Experience and time play a factor as well. Over time we naturally get better at identifying and operating within them, provided we have awareness to begin with.

Another benefit of understanding and recognition is avoiding the common mistake of overindexing on one polarity. If you are too focused on exercising control for example, you might end up doing the exact opposite. Recognition also prevents unnecessary frustration which often leads to burnout.

3. Adjusting for predispositions

What paradoxes highlight is that there are polarities in how we approach situations. And all of us out of habits are predisposed towards one polarity more than the other.

There's nothing wrong with this, it's what makes the world interesting. However, being alert to our own predispositions can help uncover angles that we might not have considered. For example, an autocratic style of leadership while universally decried, might be exactly what the situation requires.

4. Getting better at reflection

An effective but often underutilized method to get better at navigating paradoxes is skilled reflection. Except, most leaders don't deem it as a good utilization of their time. Without reflection, you won't have the bandwidth to build your muscle of judgement to figure out what the situation truly requires. You are more likely to act out of common habits and predispositions, which are not always optimal in whatever context you find yourself.

Effective managers figure out how to be reflectively thoughtful in a job that naturally discourages it. In a job that rarely allows managers uninterrupted time on complex issues, reflective managers attend to such issues intermittently and incrementally, giving themselves time to learn as they proceed.

- Henry Mintzberg in Managing

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  1. Being the Boss by Linda Hill and Kent Linebeck.
  2. Managing by Henry Mintzberg.
  3. The Unfinished Leader by David Dotlich and Peter Cairo.
  4. Strategic Management and Organizational Dynamics by Ralph Stacey and Chris Mowles.
Sheril Mathews
I am an executive/leadership coach. Before LS, I worked for 20 years in corporate America in various technical & leadership roles. Have feedback? You can reach me at
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