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.

Which One?

Deciding on your dessert at a lovely evening out with friends can be hard. Is it the lemon mousse with white and dark chocolate? The strawberry shortcake? Tarte Tatin? Blackberry or peach sorbet? OK, you might make a choice you regret, or it just may not arrive and look or taste as you expected, but seriously this is not a complex decision: you won’t let anyone down, you can’t really make a bad decision here. Your dessert decision is simply a matter of choice, your choice alone. According to some scientific research, adults make around 35,000 conscious decisions every day, while others estimate that number to be as high as 350,000. Deciding on the initial path to take ,and the nature of the decision, whether it be a simple choice of sweet, or more, is definitely a huge part of our lives as leaders.

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.

An All-Around Good Idea

n efforts to ensure that leaders at all levels receive helpful feedback, supervisors and trustees frequently look to the power of the 360 review. This is a process designed to elicit developmental feedback from a range of sources 360 degrees around the participant, with the goal of delivering honest and authentic data about a leader’s work from multiple perspectives; this approach closely reflects the actual up, down and sideways working relationships that characterize how most employees actually work today.

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.

Welcome Change

Change isn’t easy for some of us; we resist and worry and wonder. While for others it is in their DNA and they cannot wait for the next moment to shift gears. Change, however, typically signifies growth and without growth we run the risk of stagnation. Wherever you are on the REMAIN/ CHANGE spectrum, the fact is that change is constant. Whether you are an easy adopter of change, or whether you tend to avoid change, learning how to predict change, harness change and live a change friendly life, will help you avoid stress and mental anguish and basically make you a better member of your team.

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.

The Liminal Landscape: 2022 Revisited

Summing up the past year in terms of themes, trends, new ideas and developments in the workplace proves not as straightforward in 2022 as we might have expected. In fact, SmarterWisdom believes that any new place at which we have arrived this year isn’t about content at all, but rather about state—state of being, state of understanding, state of wonder! It’s a position that perhaps we would benefit from paying close attention to, even though this moment—or space—is liminal. To be in a liminal space is “to be on the precipice of something new but not quite there yet.” A liminal space can be metaphorical, emotional or physical. And for many people, perhaps understandably, it’s an uncomfortable position.

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.

London Bridge Has Fallen

Somewhere on Twitter this past week, amidst all the tributes posted out of respect upon her death, I read that Her Majesty Queen Elizabeth II was “the first girl boss” (she became Queen at 25 over 70 years ago) and it made me think about what her tenure (she was the world’s longest-serving monarch) might teach us about organizations and leadership. “I cannot lead you into battle,” the Queen said in 1957. “I do not give you laws or administer justice, but I can do something else. I can give you my heart and my devotion to these old islands, and to all the peoples of our brotherhood of nations.”

In fact, it is perhaps easier to think of what kind of leader the Queen was not, rather than align her with a corporate title: not a chief executive officer, a president or a director. Given the length of her service and the ways in which she established the idea of monarchy in peacetime, she seems like more of a founding partner than CEO; and because of her work away from day-to-day operations, she is more like a board chair than senior manager. It is actually quite difficult to find a good analogy for the role of the Queen as a leader, and yet leader she was, as monarch and head of state.

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.

Engage and Make It So!

A standout article in Fast Company in their Leadership Now section (July 11, 2022) especially inspired our deeper thinking about why supporting and engaging Gen Z-ers, in particular, is so important. For leaders and managers to adopt behaviors and create structures to help create the most productive settings for the Zs will clearly be worthwhile. Paying attention to the generational cohorts that exist in your organization might be a good starting point—for example, we know that different ages and life stages often seek different benefits as part of their compensation packages; might that be a good general starting place for your human resource officers?

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.