Dealing With Dilemmas
When I was a head of school, it was quite common for members of my Board of Trustees, usually at an annual conversation about how things were going, to ask me: “What keeps you up at night?” When I moved into my current role as a leadership coach/thought partner, I found that I too began to use this question quite consistently. What are those nagging thoughts that re-visit us, usually as we try to drop off to sleep, or in those hateful hours when we simply cannot get back to our desired rest.
The quandaries that show up in our minds at these times, and others, are frequently puzzles where all possible solutions offer some kind of downside. In addition, they are issues that simply won’t go away, neither night nor day and in fact, we are driven to find a way forward. The word dilemma comes from the Greek word dilēmma, and the combination of the words di- meaning "twice" and lēmma meaning "premise" seems to scream interminable difficulty! In fact, the word dilemma was originally a technical term in logic that referred to a type of argument where a choice had to be made between two equally unfavorable options.
Being trapped in what might feel sometimes like a vortex of choices is so common in the life of anyone managing an organization. Dealing with dilemmas at work or at home, needs to become second nature, however difficult that may be. How might you face these conundrums and are there failsafe approaches that you can use to alleviate such excruciating moments.
For the last couple of years, in my coaching work, I have partnered with a friend and colleague, Julie Faulstich of Stony Creek Strategy in creating leadership cohorts of senior leaders from independent schools. In these seminars, which we call Finding and Leaning into Your Authentic Authority: A hands-on, active learning cohort for female senior independent school administrators, we use the essential element of the dilemma and a protocol originally developed by National School Reform called the consultancy, to present problems and uncover, in a small group format, the elements of the dilemma. Deconstructing the central issue and articulating it in different, and increasingly refined ways, is one way towards solution. These solutions place you, the struggling leader, as the central actor whose actions will unravel the situation further as you design a plan that takes you forward.
Let’s consider an example. A head of a small school has an academic dean who has been at the school for over 25 years. This dean is pretty good at her job, well-loved by students, faculty and parents alike. She likes to do things her way—and she gets good results: students get in to college, teachers get what they need and she is a supportive, decent colleague. The head of school, however, has been charged with making significant changes and bringing the school more up-to-date with a different schedule for classes, more integration of technology into the classroom and a less confined, academic subject approach to learning. What keeps this head up at night is: can she bring these changes in with the current academic dean remaining in the role? And if she attempts to move the dean on will she incur the anger and frustration of students, teachers and families?
As a mentor working with this head, or in a consultancy group such as our cohort, what kind of probing questions might we ask? Here are a few:
· Is the mandate for this change clear to the whole administration?
· Is the head fully comfortable with the mandate?
· How much of this mandate is about a change of operations rather than a strategic (board level) change?
· Has the academic dean been involved at a meaningful level in buying into and understanding this change?
· What is actually keeping this head up at night; what is she most concerned about: Failing the board? Upsetting the community? Failing the students? Underestimating the academic dean?
These are all questions with no easy answer and they ideally are aimed at the practice or possible next steps of the head herself, rather than anyone else. Most predicaments like these need to come back to our own actions. In speaking more with Julie after one of our recent cohort meetings, she adds: “Often when we wrestle with a problem, it's connecting to something inside ourselves—sometimes a vaguely felt insecurity or fear around our capacity to lead. These are very complicated jobs! And while there is often no single ‘right’ answer, if a leader can name what is going on under the surface for her, that's an opportunity for growth. A trusted group with a little distance on the issue can support a leader in reaching that insight."
Sometimes the difficulty is an ethical one; commonly it involves a human resource matter, as in the example above. Deconstructing it with the help of trusted advisors will usually release some of its mystery and help you to see its true nature. Sometimes you will find that the complex nature of these kinds of problems might provide several do-able directions to follow. By analyzing the components more surgically, your choices become not only more obvious but also may evolve naturally into steps in a multi-stage solution. Such a solution, with stages, can often be the answer to facing complicated situations.
If you have a trusted senior team, or a group of trustees who form a support group of some kind for your work, consider placing them in this consulting group mode—you are not asking them to solve your problem, rather to help you see it more clearly. Next time you wake up tossing and turning with one of these perennial organizational issues, consider how the NSR protocol, or others like it, might be just the ticket to get you back asleep. As is often the case, beginning the work towards the unraveling of a problem, and even moving somewhat closer to what you can do, bit by bit, is half the battle!