4 Types of Challenges Leaders Face

I recently came across a book (Coachbook: A Guide to Organizational Coaching Strategies and Practices) that has some really good content and frameworks for those of us who coach high-level leaders.

First of all, what do I mean by “high-level leaders?” The leadership tide of the last few decades has pushed the notion that everybody is a leader in some ways. I guess that’s true since everybody exercises influence in multiple ways and we all stand to be more intentional about increasing our positive influence. But don’t be mistaken: leaders who occupy positions of great responsibility face different issues than does the leader of a small work team, the leader of the Sunday morning ushers, or the leader of a Boy Scout troop. I sometimes call these “enterprise leaders” because they exercise leadership that affects an entire organization. It’s not that a leader has to be the CEO or CFO or C-whatever-O, the leader could be in a strategic role that matters across the organization.

At issue with high-level leaders is that they face unique challenges related to change and complexity. Often these challenges stem from the scope and size of the organization, as well as the number of direct reports (especially the number of cascading direct reports).

For example, a marketing director I’ve coached for several years has only 3 direct reports. But each of his direct reports has 3 to 5 team members reporting directly to him. And each of those team members is responsible for a team of staff (usually a handful of full-time and part time employees). Do the math and you’ll see that this director is responsible a workforce of over 100 people. All of those people represent a long list of issues and responsibilities that span practically every subject taught in a college: finance, human development, arts, capital management, real estate, psychology, communication, politics, local government, etc.

I’m tired just writing that paragraph! But hopefully the paragraph helps you see that a leader of even a moderately-sized team must deal with an amazing array of issues.  And that’s what I mean by “high-level leadership.” Now, back to Coachbook. One of the things in Coachbook that I found very helpful when coaching high-level leaders is a four-fold framework of the issues faced by leaders. Here are the four types of issues, listed in order of  increasing complexity: puzzles, problems, dilemmas, and mysteries. According to the authors, as a leader’s responsibility increases, he or she will gradually face more high-complexity issues and fewer low-complexity ones.

If you lead (or you coach leaders), you might find these distinctions helpful. Puzzles have answers. “Puzzles are the everyday issues that anyone working in an  organization must face. They are uni-dimensional, in that they can be clearly defined and can readily be quantified or at least measured.”(14) In business, leaders face all sorts of puzzles: a heating unit breaks down, a manufacturing process to be reconfigured, a hiring policy needs to be implemented, etc.

Problems need solutions. “Problems can be differentiated from puzzles because there are multiple  perspectives that can be applied when analyzing a problem, several possible solutions associated with any one problem and multiple criteria that can be applied to the evaluation of the potential effectiveness of any one solution. There are many more cognitive demands being placed on us when we confront problems than when we confront puzzles—given that problems do not have simple or single solutions.”(15) For leaders, problems come in many forms: What marketing strategy is appropriate? How should limited budget resources be applied to staffing?

Dilemmas are complicated and complex. “When certain issues that managers face appear impervious to a definitive solution, it becomes useful to classify them as dilemmas. While dilemmas, like problems, are complicated, they are also complex, in that each of the many elements embedded in the dilemmas is connected to each (or most) of the other elements. We may view the problem from one perspective and take action to alleviate one part of the problem, and we immediately confront another part of the problem, often represented by an opposing stakeholder group…” (16)  Worse still, leaders sometimes face nested dilemmas. Leaders face dilemmas such as what to do with a key salesperson who is making great numbers while also exhibiting troubling and demoralizing behaviors.

Mysteries are the issues we must take to God. “Mysteries operate at a different level than puzzles, problems and dilemmas. Mysteries are too complex to understand and are ultimately unknowable.”(19) Mysteries have no  outcome, no way forward and must be lived with. Mysteries involve not only our organization and those within the organization’s scope and influence, but elements beyond us. For example: How is it that I have my particular set of talents and gifts? Why did a tornado hit our business and not the one a block away? What made the difference in how my children turned out so different from one another?

One key to leadership success is identifying what kind of challenge you are facing.  This is because if you apply a strategy for puzzle-solving when what you’re really facing is a dilemma, you’ll get very bad results.  So use this framework to clarify what kind of issue(s) you’re facing and then take the appropriate steps to dealing with it.


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