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leadership lab

CEO and co-founder, FreshBooks

Like many traits, leadership is partially an inherent skill, but it is also something to shape as you progress along your career. To become a successful leader, begin by putting yourself in over your head.

Embrace your malleability

The earlier on you are in your career, the more malleable you are. You are a blank canvas. The activities you involve yourself with today and the challenges you sign yourself up for now will shape your longer-term direction. It may sound painful, but to gain the leadership qualities you desire, what you need to think about is how to involve yourself with a project that completely overwhelms your capacity to get things done.

Companies like McKinsey do this with their employees by placing bright people in situations that encourage them to develop new perspectives and reconsider how they might complete a project. Leaving your comfort zone will tax your perseverance to the point where you are forced to grow and do things differently to succeed.

If you start putting yourself in the deep end and getting over your head today, you'll find the path to growth and leadership begins to illuminate itself.

Jumping into the deep end: An extreme example

The mantra of putting yourself in difficult situations holds true later in your career, as well. A few years after founding my current company, the leadership team and I decided it was time to embrace our own challenge. We started a second company within our company with the goal of developing a product that would challenge our assumptions about the product we currently offered.

We wanted to create a whole new version of our product and launch it without breaking our old product or disrupting the experiences of the millions of customers using the older platform. The task was akin to changing the engine of an airplane while it was still in flight, and the process certainly felt like a life-or-death exercise; we had no clear path to success when we began. The experience made each of us a better leader.

Your surroundings play an important role in your development

When you bet the whole company on an effort as we did, or when you bet your current position on a purposefully difficult project, you will roll the dice. You have a team of people relying on you to complete your project or, in our case, a few hundred people expecting you to lead them through this make-or-break activity. As you embark upon this journey of challenging yourself, remember these two suggestions:

  • First, work on something you really believe in. You’re not looking for a job, you’re looking for a mission. If you’re on a mission, it will be easier to guide yourself through the most difficult moments you encounter. Surround yourself with what you believe really matters.
  • Second, remind people around you that you’re on a mission. You will have people relying on you, and chances are that like most people, you will make part of it up as you go along. It is your job to figure out the project while also supporting others around you so that they are not paralyzed by fear.

Do something you haven't done before

Your ability to keep finding difficult projects for yourself will pave the way for a rewarding career. Try to not only immerse yourself in challenging projects, but try also to surround yourself with people who will challenge you. Look to build a team that doesn't have a fixed mindset, that includes people who are open to new ways of solving problems. Try to open your mind to different ways of accomplishing your goals. Putting yourself in over your head may sound frightening, but doing so is the best way for you to become the leader you'd like to be.

Executives, educators and human resources experts contribute to the ongoing Leadership Lab series. Find more stories at and follow us @Globe_Careers.

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