What Does Leadership Mean to Me?

By Guest Blogger Ben Eastman, BA, CIP

Say the word “leader” out loud. Close your eyes. What do you see? Some of us see a battle-hardened general; others see a crisp black suit. Some may see a new piece of technology, or a big building with bright letters.

Leadership is one of the biggest challenges to not only our industry, but to the world we live in. What makes a good leader? Is it grace and civility or is it the ability to get the job done and influence people? Does a specific type of personality help or hinder what it takes to become a strong leader? How do we develop leadership skills in our ever-changing, modern world, with all of its different mediums and channels, to effectively announce that we, the next leaders, are ready for the opportunity to take the reins?

Leading people is something some people strive to do and relish when given the opportunity. To others, the thought of having to lead scares them and limits their ability and potential growth in the workplace.

Leaders come in many different sizes, shapes, and forms while serving many different purposes. While there is no finite consensus regarding the common qualities of leaders, I wanted to weigh in with my take on what leadership is to me.

Personal Connections

In my experience, the best leaders are the ones that can effectively connect with the people they manage or are responsible for. For many, leading is how to get the most out of their teams every moment, every quarter, and every year from a measurable perspective. While this may be great for the profitability of a company, the repercussions from applying too much pressure to an individual could have the opposite impact the following years.

Great leaders find ways to empower individuals on their team and consistently challenge them in a positive manner. Empathy is of great importance to all of us in the insurance industry as we are there to respond to people’s needs during their darkest moments. Our leaders have the unique challenge of not only managing the business intricacies, but also must guide us in taking proper care of our clients. Great insurance leaders will know what makes their team click, what makes their pulses jump and what their dreams are.

I’ve been fortunate to have been able to follow fantastic leaders. They always found the appropriate way to push our teams to be better. Most importantly, they knew when we needed a break or a kind word. Finding a connection to the people you’re leading will make them put in that extra effort and “buy-in” faster. From my experience, leadership means nothing without the connection to the people you are intended to lead.


Leading is hard. If it were easy the world would be full of exceptional leaders. All of the great leaders I’ve encountered throughout my life have an increased level of self-awareness resulting in effective delegation of responsibilities and duties to their team. They count on the people they have surrounded themselves with to make the best possible decision. Effective leadership stems from the ability to influence change. This can be accomplished by a leader having developed a strong personal identity. With a strong sense of who they are, these leaders exhibit a level of confidence that empowers their employee/team to rise to the occasion and creates an environment in which all parties are accountable to the overall goal. My favourite leaders are the ones who are so comfortable in their own skin that they are willing to acquiesce some of their power to help you along in your development.

Being able to follow is the first stage to becoming a leader. Being able to develop leaders is what makes truly great ones.

Willingness to Fight

Remember when I asked you to close your eyes earlier? Picture that person again. I always see my leader as the same type of person. Someone who is willing to take a punch, whether in the form of criticism, a failed initiative, or a bad decision, and get up off the floor and do it all again. “Jab, step, jab” is what I see in great leaders. They move, hit, get hit - but at the end of the day they keep moving. They battle for the right way, they stand up for the people they lead, and most importantly, they never give up.

Chris Rock said something that has always resonated with me. “I’d always end up broken down on the highway. When I stood there trying to flag someone down, nobody stopped. But when I pushed my own car, other drivers would get out and push with me.”

Decisions need to be made, a leader will not always make the right decision (I mean, who could?); but I bet it will not stop them from making the next decision. Those are the type of people I want to follow.

Concluding Thoughts

Our industry is changing. It has been for years. What will be pivotal for the next generation of leaders is to learn from those who lead now. Whether through mentorship programs, educational courses offered through the Insurance Institute or other institutions, or in real-life development opportunities. We must always remember that leadership can come in any form.

A title will not create a leader, it may create a structure or system in which authority is granted, but it does not create leaders. Lead by example, through effort, through success and lead from a place that will help you create other leaders, as that is the true example of leadership.


Category : General, Leadership