Leadership

Leaders have experienced unprecedented challenges over the past couple of years. Whether you’re an emerging leader or a seasoned business professional, everyone can benefit from mentorship and outside expertise. I’ve often noted the fact that while there are numerous training materials and resources available at the beginning of an entrepreneur or business person’s career, as you find more success and progress in your career, the resources run out.

Without learnings from mentors and peers, each of us is condemned to making and repeating mistakes that others have already overcome, which is illogical. While I can’t be a direct mentor to everyone, I want to share as much of what I’ve learned as possible in the hopes that it helps other leaders. I’ve compiled all of my blogs, articles and more on the subject of leadership in order to help you avoid the mistakes I made and learn from the successes I’ve had.

Now, more than ever, business leaders are looking for support, strategies and tactics for the future. We must vigilantly prepare ourselves and our companies for a variety of outcomes. I’ve led companies through a variety of challenges, from 9/11 to the Great Recession, and now the COVID-19 pandemic. Throughout it all, we experienced new challenges but ultimately grew through them. Risk management plays a vital role in every leader’s career because the law of unintended consequences comes into play more often than not. Balancing risks with gains, and building and leading a team through it all requires a multi-faceted leader with a strong vision.

Leaders need to be prepared for a variety of circumstances in order to effectively lead their companies. They don’t just build—they reinvent. It is up to the executives at companies worldwide to steer their organizations through whatever challenges are presented. Here are some of my tips for leaders that apply to a variety of circumstances:

01

The law of unintended consequences comes into play more often than you think. One concept leaders need to become familiar with is “tail risk”. Tail risk is the chance of loss that occurs due to a rare, unpredictable event. These are extreme or unlikely events, but they always come with a cost. Preparedness is an essential quality of a successful enterprise, and it is necessary to understand the difference between being reactive and being proactive. Proactive leaders always come out ahead.

02

True leadership comes with the ability to fundamentally change your business model as necessary. It’s easy to find a strategy that works and cling to it regardless of what changes occur to the economy or your business. Reinvention starts with your company, you as a leader, and then trickles down into your team (otherwise your team won’t be in line with the new company culture and vision). Your willingness to adapt to the times and change yourself as a leader are imperative to success.

03

Leaders and executives are not machines—you must strike a balance between knowing when to work and knowing when to rest. “Fallow time” is regular down time that is a necessary component of everyday life. For me, fallow time can look like sailing, mountain climbing, or any number of outdoor activities. Having interests outside of the office make for a more dynamic individual, which makes for a better leader. Instead of looking down on those who have hobbies and interests outside of work, recognize that these fallow time activities are an important component of a balanced life. Leaders need to hit the reset button every once in a while in order to approach their company with fresh vision and perspective.

04

It’s time to reevaluate company structure and become less task-oriented and more outcome-focused. When the pandemic hit, leaders scrambled to manage their teams remotely. Many changed company structures and adapted to digital tools like Zoom and Slack to stay connected, but it can be difficult to keep employees engaged throughout the monotonous day to day. If your employees are getting their work done, you don’t need to micro-manage every aspect of their workday. It’s time to move to an outcome-focused model where employees have the freedom and flexibility to work in the way that suits them.

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