Leadership: A Winning Approach


Chicago Cubs players celebrating their 2016 World Series win
Chicago Cubs Celebrate their 2016 World Series Win

Back in 2016, the Chicago Cubs finally ended 108 seasons of baseball futility, winning the World Series in seven games over the Cleveland Indians. Throughout that remarkable season, then-manager Joe Maddon inspired a chill clubhouse culture with the laid-back reminder to “Try Not to Suck.” I don’t play baseball but can say with confidence that no other slogan, no catchy philosophy, no trendy leadership fad even begins to approach the wisdom of these words when it comes to managing people.


Try not to suck. What do these four words tell us about leading teams in the challenging, constantly changing environment we find ourselves in today? For that matter, what does “challenging" even mean anymore? For the past 15 months, we’ve seen people’s lives turned upside down by a “challenge" we can’t actually see. We’ve witnessed governments struggling to respond to this challenge. We’ve seen economies go to ruin. We’ve watched as some companies and some jobs were characterized as essential while others were essentially cast aside. We’ve watched families struggle to manage work and school and health – charting a path through unfamiliar, unmarked territory.


So, using the word “challenging" to describe general business complexities might not be a great fit for a while. It doesn’t change the fact, however, that we live and work in extraordinary times. Times that call for an intelligent response. An intelligent, genuine response – not some hot new buzzword-laden technique in managing and leading. These extraordinary times call for a common sense, people-focused response.


Try not to suck.


Look at your team members as individuals. Individuals who have been through more than 15 months of fear, uncertainty, and loss. Everyone has experienced some type of loss over the past months. Perhaps the actual death of a friend or loved one. Perhaps the loss of a job or income. Loss of occasions like kindergarten parties, proms, graduations, weddings. Loss of the routines we know and trust. Loss of time with family and friends we hold dear. We even lost funerals, where we come together to mourn our losses as a family, as a community. Yes, we continue on because that’s what we do. But take the time, with intent, to look at each individual on your team and recognize that their losses are real.


Listen to your colleagues and to your team. Things have changed. For 15 months, people figured out how to make it work from home. How to juggle family and work and school under one roof. Or how to handle the isolation - the loneliness of having no coworkers at hand to talk with about the big things in life – or even the little things. Like few other times in our history, people were confronted daily with the realization that work isn’t everything. The realization that people – family, friends, connections – were so much more important and so much more fragile than they ever knew. It will be difficult to put that realization aside and return to a world where the 9-5 rules each day. So listen. Tune into the change.


Understand. Understand that for some, nothing ever changed. Some workers never had the chance to work from home. They went in every day, no matter what the infection level or the number of cases reported in the news. Now they’re hearing others complain about going back into the office, about dealing with child care issues, about dealing with a commute. The last 15 months, for so many reasons, have led to divisions across jobs, across organizational levels, across industries. Why is one type/size of business more or less valuable, more or less essential than another? Why is one occupation more or less intrinsically valuable, more or less critical than another? Understand the resentment and the frustration that result from what must seem like judgements of worth or importance. Understand the irreparable harm that comes from division. Understand what brings your team and your organization together. Work on healing the divisions through a focus on shared interests and shared goals.


The most important aspect of the Try Not to Suck approach to managing and leading? Be human. Be humble. Put your ego and your own insecurities aside. Years of working with leaders across industries have shown me time and time again that the best leaders have a strong sense of their own worth. They are confident in their abilities. They are able to look beyond their own internal fears and concentrate on the needs and best interests of others. They are introspective enough to recognize a disconnect between their words and their actions – and honest enough to address it. If you are unable or unwilling to separate your fears or insecurities from your duties as a leader, ask for help. Your team deserves that.


One incident in the seventh game of the Series – perhaps the pivotal moment of the series - further highlights the value of leadership self-awareness. During a rain delay late in the game, with the score tied, Joe Maddon eschewed the expected managerial rally speech, deferring instead to respected veteran Jason Heyward. Knowing when to step aside and let others lead is the mark of a truly insightful leader.


Finally? Try. Trying doesn’t mean never failing. The Cubs lost 58 games in that World Series season. They were down 3 games to 1 in the series with Cleveland but came back to tie it 3-3. They lost a comfortable lead in game seven and saw the game go into extra innings. But they persevered. Being an effective manager, being an inspiring leader, is difficult. It takes unflagging attention, constant effort and candid, clear-eyed self-understanding. It takes the courage to swing on a 3-2 count with two outs.


Try not to suck. You can do this.

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