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With elections afoot, now is a perfect time to think about what we want from our leaders, not just for Hawaii’s next governor, but all leaders. Senators and representatives do important things but so do leaders who run a small business, steer a nonprofit or coach a soccer team.

There’s an old saying that anyone can captain the ship when it’s in a harbor. Out at sea it’s a different matter.

If I was posting a generic ad for future leaders, here is what it might look like.

I had my own experience as an accidental CEO in a medium-sized enterprise on the mainland when I was recruited away from Hawaii for a few years. Leadership of that sort wasn’t something I sought, but I worked hard and left the place better than I inherited it.

Here is some of what I learned.

Context And ‘Moment’ Matter

All enterprises have lives. They are born, they grow, they expand, and they go through periods of health and illness. They decline, they revitalize, they transform and sometimes they end. Leaders may have many good attributes but they need to “fit” the circumstances and trajectory of what is needed at a moment in time.

Even if the fit seems perfect, great leaders aren’t great all the time. They are human. They have their warts, but good ones rise up to meet the critical issue at the critical moment.

John Burns met his moment when he led Hawaii’s Democratic revolution. John Waihee met his at the ’78 Constitutional Convention. And I know people who shepherded their restaurants, NGOs, or schools through the financial retrenchments of 2008 or fierce Covid-19 storms of 2020.

Now imagine you are an aspiring or reluctant leader and have just learned you are asked to provide direction, stewardship and governance to an enterprise in Hawaii that is at some fork in the road. The job you are taking on is probably messy, underfunded and perpetually controversial with some individual or faction pecking at you.

It may be financially challenging but it’s usually politically complex. You must bring hope but be realistic. You must relate well to others but stand apart. You must navigate change but negotiate stability. You must inspire, plan, persuade, order, influence and cajole. Above all, you have to make decisions.

Research says that top corporate leaders “lead” in five different ways. Some focus on strategy and long-term horizons. Others leave strategy to the heads of units and invest time and energy in hiring, managing or firing them. A third way concentrates on technical expertise, innovation and the continuous improvement of core products or services.

A fourth approach focuses on controls: finances, markets, capital assets, services, sales, personnel. A fifth approach concentrates on rapid change. It shapes turn-arounds, usually in the face of oblivion, but sometimes coupled with larger transformations that upset entrenched people desirous of continuing the status quo.

But these are not the only choices. Some leaders have gifts for inspiration. They bring hope in the midst of pessimism. Others are good at crisis and become commanders in the face of danger.

Some are masterful tacticians and can move important pieces on complex chessboards. Others are unifiers and bring people together. Some excel at downsizing, others at upsizing and growth.

Every leader does some or all of these things, but most are best suited for one approach. They also succeed if there is a good match to the stage of an organization’s life and can compensate for their own weaknesses.

Your work as a leader, therefore, will be filled with paradox, ambiguity and dilemma. Get comfortable with that. Whether you like it not, you will actually be a paradox manager.

Managing Vs. Leading

Every organization, institution, and agency has a story about itself, sometimes more than one. If you are the leader, you are responsible for organizational “sense-making” and the master narrative that is at the heart of all missions. In Hawaii, roots and connections to community are especially important.

You will face constant tugs, pulls and criticisms from people who would do things differently and you will need to be responsive to those that are credible, and some that aren’t. If you can’t stand paradox and ambiguity, if your world is purely without shades of gray, better find another line of work that is less aggravating.

Some thinkers draw bright lines between “management” and “leadership.” I don’t. In reality, leadership and management twine together in a thick braid of things you must pay attention to. On different days different matters require attention, some of them urgent, others ambient. You will have to figure out what has priority.

The word “management” traces its origins to the art of horsemanship and hints at the “braid.” It comes from the Italian word “maneggiare” — “to lead horses.”

Horse whispering, gentling or taming is a special craft. In Colorado, where I was during my CEO odyssey on the mainland, I once spent a long day watching a professional horse “coach” work with a problem animal that kicked and bit all the time.

As he worked, he talked and as he talked, he was persistently clear on one point. You don’t “train” horses. You lead them, and managing them requires confronting hard-wired equine evolutionary dilemmas.

Horses, he said, are built to do different things simultaneously. The back legs are all muscle, strength, and power. They are the engines of the horse-motor. Basically, they push. The front legs steer. They give nimbleness and dexterity. Horses can push hard and turn on a dime.

Being herd animals, they like to stay together but they also have personalities, pecking orders and quirks. Being prey animals, they instinctively don’t like having things on their backs or pulling objects. Being social, they herd up for mutual benefit.

Leading horses, then, like leading humans, means working with multiple impulses at the same time. You want horses to go fast and slow. You want them to be loyal and not devoid of spirit. You want them to obey and you also want them to work for a common effort.

Note the word “and” instead of “or” or “but.” You want horses to be able to do multiple things all at once.

The truth is your appointment as a leader is an honor and a burdensome kuleana.

These turn out to be dilemmas for you and the horse. A dilemma is when you have to choose between two paradoxical and equally attractive or unattractive alternatives.

A nice dilemma is which of two extraordinarily talented individuals you should hire. An unattractive but very real dilemma is when your boss, or your board, or the marketplace says: “You’re in charge — but don’t screw up.”

So managing ambiguity is what you do. It is all about handling paradox rather than the short lists of behaviors and traits so many leadership books suggest.

The truth is your appointment as a leader is an honor and a burdensome kuleana. It requires you to succeed in very specific ways and work within boundaries and tolerances.

Nobody can tell you exactly where the outer edges of your choices are. You have to learn them in your own way and constantly test them against situational realities.

Finally, you will need to be confident and secure in your leadership but if you are smart, you will always know in your heart that it is temporary. Tenacity counts. There will be times when you feel like giving up, but you won’t because you have to get the job done.

In the end, leaders aren’t what they profess, feel, or think. It’s what they do and how they do it. But there always comes a time when you know you have done everything in your power to make things better than you found them, perhaps when the organization or enterprise enters a new stage in its life cycle, or perhaps when your work has stopped being helpful.

That is when you need to pass the torch.

Everyday Paradoxes

Leaders have to confront these paradoxical obligations. They have to balance the upset (and sometimes chaos) that comes with change with the need for reliable constancy. They need to get the wrong people off the bus and the right ones on. They have to judiciously use carrots and sticks and weigh the costs of certain dangers against the benefits of possible opportunities that dangers often create.

Most of all, you have to exercise power. In physics, power is the rate at which energy is used, transferred or transformed to get work done. Authority is a useful form of power but it is not the only one. Power can become abusive if it is disrespectful, especially in Hawaii. It can be acquired when you are trusted. Maya Angelou said, “People will forget what you said, people will forget what you did, but people will never forget how you made them feel.”

In my work on the mainland with a very mission-driven organization, I relied heavily on the passion all 60 of my people had for the work we were doing. They wanted good pay and fair benefits, but they all also wanted to be part of something bigger than themselves. If they didn’t, they didn’t last.

There is a Polynesian proverb I heard from my friend Tusi Papalii Avegalio, a Samoan high chief and a brilliant UH Manoa business professor. He says if you want to teach people how to build a canoe you first need to make them yearn for the sea. That is one of the highest callings of a leader: getting groups together, getting them aligned and getting them productive because they want the enterprise to succeed.

Touchstones

In the face of stark choices and either-or paradoxes, I usually had to do some of both. But leaders also need personal moorings and holdfasts that help guide tough choices and the consequences that ensue. There are three that I want to assess in the current flock of political candidates, no less than those who lead businesses and civic organizations:

• Do they really fit the mission of the enterprise, and can they personify it? What’s the best past evidence?
• Do they have a moral compass and a code of conduct? What’s the best past evidence?
• Can they confront difficulties, engage and consult with others and make tough decisions? What’s the best past evidence?

“All great leaders,” said John Kenneth Galbraith, “have had one characteristic in common: a willingness to confront unequivocally the major anxiety of their people in their time. This, and not much else, is the essence of leadership.”

Leadership in Hawaii is especially hard. We are diverse, intimate and we need new men and women leaders who have the courage to become “great” when the great moment appears. Even if it’s hard.