On Leading

I’ve been thinking about leadership a lot these days as I’ve watched elected officials and community leaders struggling to meet this moment. The confluence of the pandemic and its economic fallout, racial protests and the action required to dismantle centuries of systemic racism, the collapse of confidence in government, and the stress of so many unknowns about the months to come is a powerful mix of challenges. No leader is super-human, but we do need extraordinary leadership now.

It’s important to note that most people are not leaders. They simply go where they are led—sometimes gratefully, sometimes grumbling every step of the way. Make no mistake, however: the goers and the grumblers cannot lead, no matter what some of them might think. Back-seat drivers can neither see the road nor steer, and they have no stomach for speed or hazardous conditions. Second-guessers were never in the room for the hard stuff, trying to discern a path through complete fog with cliffs on either side. The Monday morning quarterbacks…yeah, they can’t really throw a pass anyone could catch even when they aren’t under pressure. And there is always pressure. This is real life, after all.

So leadership matters. In fact, I think as I consider my lifetime, it has almost never mattered more than it does now. Thus, I think we must consider what we expect from those who lead. You may have your own list, but this is mine: a powerful set of tools I have seen the best leaders in my life use well.

Courage: Leading is not for the faint of heart. Every step into the unknown requires bravery. Courage isn’t hearty, false bravado, though. Some of the most courageous people I know are quiet, steady types who know that putting one foot in front of the other is sometimes the hardest thing to do in complex times. Some say fortune favors the bold, but my experience has taught me it favors the brave…because leading is rarely about leaps. Instead, it is usually about taking steady steps into the unknown and deciding when to reverse or change course. It takes a special brand of bravery to admit the path you championed or chose is no longer the best one. The best leaders I’ve followed were not only brave enough to choose a path among confusion options, but also to say, “We’re going the wrong way” when it was necessary.

Optimism: When you set out for the other side of chaos, and you tell others, “Follow me!” you stake their lives, their hopes, their futures to your own decisions. The thought of what could go wrong can be paralyzing for those who are not inherently optimistic and hopeful. But hope, as one of my colleagues was often fond of reminding us, is not a strategy. Optimism is not blind hope that everything will be ok. Optimism is the belief in our ability to drive for a positive outcome together. It is optimism that yields the confidence to say “we’ll figure it out” and to step forward rather than cowering in the shadows.

Curiosity Mixed with Humility: The best leaders I have ever known were curious people…question askers who listened hard to answers and followed with more questions. They had a deep interest in the talents, knowledge, and skill sets of others—so much that they were constantly asking for help or different perspectives. They saw patterns and possibilities even in the humblest places, could learn something from anybody, never thought their own context so unique and special that they could not find value in the truths and experiences of others. Strong leaders are voracious learners. They devour knowledge and seek new ideas—instead of feeding daily from the same trough that assures continuity and assuages ego. Because they are always learning, they evolve, change their minds, grow. They allow their teams, colleagues, and friends to influence them; and surround themselves with strong people worthy of that impactful role because they value the way that iron sharpens iron. They know they are strong because of the people around them, and this tempers arrogance and keeps pride in the right place. They are ever-mindful that we succeed together more than alone.

Conscience and Vigilance: Leaders don’t sleep well. They toss and turn. They lie awake in the dark hours before morning worrying about how particular decisions may have impacted others, how the course they are setting may result for those who depend upon them, how the random action of any one of their followers may upend everything they have worked for in a moment. They worry about protecting the vulnerable, and they have a moral compass they wrestle with in the midst of chaotic times. Hard decisions stay on their hearts and on their shoulders, so that even when forging ahead, they feel the drag of the wake our actions sometime leave. Strong leaders worry about the what-if’s, the left-behind, the roads not taken, the way the future may diverge from the present. They don’t take long to bask in the comfort of today’s achievement or the status quo, always planning and moving instead to prepare for what lies ahead while others rest a moment. Leaders never forget that people have trusted them to lead. Trust comes with a heavy responsibility. It is both an honor and a burden they can never put down.

Energy for the Tedious Stuff: Some people think leaders do the big stuff and leave the details to others. First lieutenants. Executive assistants. Middle managers. Division heads. Rough drafters. Perhaps that is true of some leaders, but the best I have known are not afraid of weeds, of rolling up sleeves for more than photo ops, of wading through big stacks of information or data or the ugly myriad details of difficult tedious decisions. The best leaders get their hands into the work—not just to show everyone they’re “one of us,” but because they know that leading isn’t the work; the work is the work.

Self-Reflection and Honesty: The best leaders know their own weak spots. They are brutally honest with themselves about failures big and small. They know the person in the mirror well, and they know when that person is being inauthentic. They call themselves out, and they set their own bars high. When sycophantic spin surrounds them, they don’t succumb to its siren song. Instead, they listen for their own voice and speak the truth to themselves even when it isn’t what they want to hear. They don’t need others to be their internet providers or router; they are each their own hot spot. They make time for reflection; it comes as easily as breath. A stumble is not a fall to those who make sense of experience and act on that knowledge. The strongest leaders I’ve ever worked for knew when to say, “We got that wrong. We can do better.” And then we did.

I note that I haven’t listed typical “leadership book” skills: vision, emotional intelligence, communication, team building. I don’t even mention work ethic—although certainly leaders “keep no office hours”. My list of what I hope for in our leaders is short, but—as we have seen all too often—so hard to find. Still, as we look at what this time demands and the complexity of the future we are traveling into together…well, I think we must find leaders with these strengths. We cannot afford to do less.