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.

Deliberately Growing Up

Those of you who read our posts regularly know that we at SmarterWisdom are quite obsessed by several general approaches to leadership development. Themes and thoughts about self-awareness, intentional thinking and action, growth mindset and (Marcie’s favorite) letting the structure do the heavy lifting, are just a few that run through our writings, just as they percolate through our thinking. Many of these approaches that we care about help to form the framework of our work with the individuals and teams with whom we spend our time. Many of them even come together and align to create a structure that we can overtly share with people in an explicit form.

Some Leaders Are Born Women

Examples of women, who are at the height of their careers and those on the fast track to getting there, offer support for the notion that indeed other women should be following this path. From Beyoncé to Oprah to Taylor Swift, women entertainers are taking names and taking charge. No longer simply the pretty faces of success, these women are smart business people who followed their insight and their guts as they saw inside their industry and ensured that they reinvented what it could be for themselves. Oprah became a mega-performer and international figure; Beyoncé became a Harvard Business School case study and Taylor Swift has not shied away from taking on the behemoths of the music industry, from Spotify to Live Nation. Each has stuck her neck out to go a different way, straying from the path most taken, and carved out the way that brought her the time, clout and, yes, financial reward, she was seeking. They are each reinventing what it means to be living their own high-powered career by redefining what that is, and by taking on established power as they do so. By seeking to control the narrative and be in control of their actions and approach, their courage and smarts are setting the bar high and at a new level for all.

The Existence of the Soul

Recently with my friend and colleague Julie Faulstich, of Stonycreek Strategy, I led a group of senior women administrators from independent schools in a yearlong seminar called: Female Leadership, Finding your Authentic Authority. We enjoyed deep and wide-ranging conversations; we unraveled dilemmas and we discussed the potential isolation of perhaps being the only one in the role of dean, assistant head, or division head, that is a middle manager and reporting to the head of school. Being in the middle in any kind of organization, is not always easy and the work these middle managers do frequently goes unnoticed—and yet without that work, the organization would suffer. So here’s SmarterWisdom’s tribute to the ones in the middle—to their very existence, and, even more perhaps: to our paying more attention to what they do and how important it is.

No Really, Look Before You Leap

In all situations, organizations devote time and energy to selecting board members for a very good reason: the quality of the outcomes of the board’s efforts will, of course, be greatly influenced by the quality of the individuals it selects. By ensuring that a structure of orientation, on-boarding and time for input and reflection is in place, the potential of each board member chosen can shine. For both the new trustee and the board their mutual effort and forethought might actually mean the fulfillment of the promise that made the match in the first place.

How an enterprise identifies what it needs in its board members may be tightly defined by its rules of governance or by the match between open board assignments and candidates’ areas of competence, but in many smaller, newer or less formal settings, driving forces include less well-documented considerations including its priorities at a given point in time, an individual’s visibility and degree of influence and access, who else is already serving and the preferences of the organization’s chief executive. In some boards, particularly not-for-profits, the ability to contribute financially and help the enterprise raise funds from others is also a key qualification.

Crisis, What Crisis?

During my 20+ years of leadership at independent schools, I definitely faced the full range of crises that might beset small schools. I learned a lot about being both somewhat prepared for these exigent events, and also about being totally unprepared and yet somehow able to invoke the necessary actions and skills to get things on the level again. Initially, and in much of my early experience of these big bumps in the road, I tended to think that crisis was always something like a chemical spill on Route 128 very close to the school. Over the years, however, I learned, and internalized, that a crisis could develop from any event or incident that might adversely affect the mission of the school, if left unattended.

Lessons from Los Alamos

It is by no accident that Christopher Nolan chose to make his latest film, Oppenheimer, about the 1940s and early 1950s, the building and use of the atomic bomb and the life and times of J. Robert Oppenheimer. The book on which Nolan based the movie, American Prometheus by Bird and Sherwin, tells the story not just of the brilliant young scientist, but also of the times in which he lived, the background of the second Red Scare, the undercurrent of anti-Semitism and the way in which one brilliant man was ultimately brought down by the establishment. The parallels for our times are clear. We may not be living with those exact issues, but we are living with the fear of global conflicts, the potential effects of climate change and the fear of failing economies and increased poverty. Watching the movie, and reading the book, inspired me to consider the possibility of lessons for our times, and more specifically, to ponder the perennial and necessary leadership traits illustrated firmly in black-and-white and glorious technicolor.

Leading Yourself

Your personal drive or decision even to care about leading yourself is a key first step of self-knowledge. Is the desire to lead myself within me? Do I want to do this? Leading ourselves is the element of our approach to our work where we think and act explicitly in order to become better at what we do. It explains who we are, where we want to go and why we want to go there. It helps us understand what we might accomplish in our work. Ideally it might also help us control our emotions and behavior, since it brings focus and ideally razor-sharp vision to our work. SmarterWisdom sees its work with emerging leaders as helping them to access this deeper knowledge of their intrinsic motivation. Some leaders however struggle to understand the importance of further analyzing and capitalizing on their drive as part of leading themselves.

But Does It Bring You Joy?

Several years ago Marie Kondo’s approach to helping us clean up our lives took hold. A key part of her “cleaning up” approach (see Konmari.com), was to hold up a household item or article of clothing and ask does it “spark joy.” During the last year or so, in particular, many people have been asking this question about the work they do: are they in a role that they like, one that is satisfying to them. We have seen various responses to these questions, from people working less and placing family and their own well-being first, to the great resignation. Does your job bring you joy? If you could hold up what you do for a living in front of you, following the Marie Kondo approach, would it make you happy? SmarterWisdom thinks that this is a question worth asking and in a way that is constructive and active rather than passive.

Kindness Matters

When I see frequent references to a concept or topic suddenly appearing all over social media or hear a term popping up everywhere in presentations or interviews, I always perk up and register the phenomenon: it makes me want to wonder out loud if there is a need out there somewhere to grapple with this particular issue. Recently, the concept of kindness seems to be the new “it” idea, poking up everywhere I look—from business articles asking the boss to be more compassionate when assigning large projects, to my doctor’s office where I encountered waiting rooms plastered with (mostly handmade) signs and posters urging people to be kind. As I consider what seems to be a rising wave of interest in decency and warmth, I find myself curious about whether or not we just want to talk about it or perhaps act on it?

Inner Wisdom Revisited: Jacinda Ardern's Resignation

In February 2020, SmarterWisdom posted Inner Wisdom Personified: Jacinda Ardern, about New Zealand’s Prime Minister, who was elected in 2017, aged 37. Last week, upon the news of Ardern’s decision not to seek reelection, I thought about the words she used in her resignation speech, that “[she] no longer had enough in the tank to do the job.” I wondered if Ardern’s brand of leadership required more in the tank than that of other leaders; I wondered if she felt she had any choice. In the 2/20 Words of Wisdom post, I argued that Ardern was a true servant leader, not someone seeking personal gain, rather someone leading selflessly in the interests of the country. Since we published that piece, which focused on the massacre in mosques in New Zealand in 2019, Ardern has dealt with the White Island volcanic eruption, and of course the Covid-19 pandemic. She has also experienced a myriad of personal threats, among them many that were seen as ageist and sexist. So while the message from our 2020 post stays the same, we are left with a lot to ponder in connection with Ardern’s decision and the loss to the world of this globally-minded leader.

Trust Your People

It seems there is a whole new movement in the for-profit world related to checking up on employees. As a certain sector of the workforce makes choices about at home, in-office or hybrid work, employers are investing in tracking and other software that monitors workers time-on-task. The concern that because we cannot see them working and therefore how do we know if they are, is driving employers to create a lack of trust, which surely will erode the mutual trust workers need to do their best work.

Time and Its Essence

One of SmarterWisdom’s core approaches to our leadership consulting work is to help leaders prioritize among the myriad of bright shiny things that beckon them each day. Step one is to prioritize, and step two is to stay true to the path you set for yourself.

So how do you prioritize? A good first step is to consider your work in levels, or as the McKinsey article suggests, gears, that is low, medium and high. Examine all the major projects that you are involved in—which takes precedence, what is next, and so on. If you stay focused on less important, mid-level tasks, you are likely to be stuck in medium gear. Yes, you can tootle along getting stuff done, but both you and your vehicle are not turning on the high-power capability that will allow you to move faster and cover more ground—and dive deeper. As a leader in your organization, you want to be in high gear a lot of the time. Think of high gear on the freeway and the large distances covered. Yes, you need to be paying more attention to your driving—but you will get you and your passengers to more places.

Is It Worth It To Me?

was talking to my niece recently about her return to work in person. She is a media/communications specialist in higher education, based in the UK. She said that without the ability to work remotely as well as in person, she would go crazy: too many meetings on-site, and no time to get her work done! I was reminded of some of my reading and research about the “new world of work” we are entering, since offices have begun to re-open and many employees are now required to return to work in person. Digging further into my niece’s comment made me think more about the potential value of returning to the office, and how many professionals, like my niece, need to know whether or not it’s worth it to them.

Whisper Words of Wisdom

The Beatles’ 1970 album, Let It Be, hit the record stores when I was a junior in high school in the UK. “The Long and Winding Road” brought tears to my eyes and became my go-to Beatles ballad for a very long time. In his new documentary, “Get Back,” Peter Jackson chronicles the making of this seminal album over a period of days and in doing so, according to a wonderful recent article from The Economist, reveals some reliable and creative thinking about an effective team of four.

Choppy Waters Need Steady Hands

During the past two years, all types of organizations, from small non-profits to corporate giants, have experienced enormous upheaval. Keeping a steady hand on the tiller as you face and adapt to the changes that appear, and paying attention to opportunities, are vital to how you capitalize effectively on setbacks. It is crucial that leaders cultivate the most productive approach on how to deal in-the-moment, and yet maintain the long-term view on how to stay the course.

An Ounce of Prevention...

Research shows us that boards and leaders who have already faced different kinds of crises, perhaps the need to cut programs, or a significant loss of accustomed admissions sources in schools, or a public relations scandal of some kind, or the loss of a senior leader mid-term and so on, are better equipped to face new ones, such as the pandemic. Schools, for example, who put policies and practices in place during the mid-2000s SARS-epidemic crisis, or even just surfaced the key generative questions, were more prepared for the recent challenges related to Covid. Having faced different trials and tests, organizations that incorporate ongoing reflective learning from these experiences, and create replicable, sustainable approaches, will thrive during new challenges and threats.

What Goes Up....

Something I learned early on as a leader was the idea of managing up. I remember my Harvard MBA spouse describing the idea to me after a particularly unproductive series of meetings with my boss at the time. It seemed I could never get my needs met, that she never seemed to notice anything that I did that I felt good about, and that she had a lot of needs of her own that I was unsure about. Fast forward through almost 30 years of leadership, working for one boss sometimes and working for entire boards of directors at others, to today and the work SmarterWisdom does with leaders facing the same issues. How do we collaborate best with our immediate supervisors? The advice my MBA spouse gave to me was to manage up, which meant to considering more where the “boss” or “the board” was coming from and work it. Is this effort really necessary? Does it pay off? How does it integrate into the whole picture of leadership success?

New Leadership Superpower: Super Systems Thinking

Thinking is hard. Planning is hard. Figuring out why what you are thinking and planning isn’t working is harder still. But in a fast-moving world, we are often doing our thinking and planning on the fly. We are taking action even as we are still processing important considerations, and we are regularly trying to remedy problems as they are happening—the proverbial changing-the-aircraft-engine in mid-air dilemma.

There are many reasons why this approach is often unsuccessful. A not unsubstantial cause is the pressure we all feel to be productive quickly. That stress can feel unrelenting and pushes us to want to “solve” or “fix” things fast. Because so few of the issues in our universe are “stand alone,” considering the implications of choices can be a time and energy consuming activity. Doing so involves generating sequences of if/then reasoning, often with many branches along the way. And that exercise produces considerable data which requires precious time for reflection. We’ve even given a pejorative name to how that can appear to others: “analysis paralysis” reflects both our penchant for rhyming terms and our bias toward speed.

Are We Having Fun Yet? (Part One)

Talk about pent-up demand! After 15-plus months of pandemic-mandated behavior---social distancing, mask-wearing, working from home, not eating in restaurants, etc., restrictions are lifting. Everyone is thinking about what will come next. Fantasies of steaming ahead, full throttle, toward a return to “normalcy” are ubiquitous: Cruise lines are vowing to set sail from the US this summer, schools are pledging to reopen for full in-person learning by the fall and workers who have been working from home are waiting to hear from their employers about what’s next for their futures. But what, exactly, will the new normal be?