How to Become a Better Leader Through Writing

As a leader, people are often surprised when they discover my big secret: I’m not a natural writer. Yes, I’m the co-founder of Calendar and a keynote speaker. But when it comes to putting pen to paper, I’m not the best. For a long time, I didn’t feel talented or see the benefits of writing for myself, so I avoided it.

As my company grew, however, I started to realize how much my discomfort around writing was holding us back. It’s easy to say, “I’m too busy to write today,” and keep kicking the can of personal and professional reflection down the road. There’s always something that demands immediate attention; sitting down somewhere to reflect and write is never high on the list.

But by not generating thought leadership content, I was depriving myself and my company of a valuable tool. I didn’t need to become Hemingway. I just needed to schedule time to write about my personal growth and the industry trends around me in order to become a better person and leader.

Writing is more than an escape for teenagers with journals or artists who lock themselves away in cabins to focus on their craft. It’s an invaluable tool that helps leaders organize their thoughts and create genuine, human connections with their audiences. In a modern market where personalization, authenticity and shared social values increasingly drive purchase decisions, written content from actual experts bridges the gap between companies and consumers.

Creating content about my own experiences and insights has helped me kill two birds with one stone. Not only am I able to challenge myself to become a better leader, but I’m also able to give my company fuel for an effective content marketing program, providing valuable assets to our team in exchange for a bit of reflection. All leaders, especially those who don’t consider themselves natural writers, should learn from my early mistakes, get out of their own way and start developing content.

Transform thoughts into useful content.

As I mentioned, I’ve never been a particularly talented writer. I didn’t enjoy it or receive much praise for my language skills. That’s not to say I never had good ideas, helpful advice or a valuable perspective to share. Anyone who knows me knows I usually have plenty to say.

Instead of fleshing out my thoughts through writing, however, I either kept them bottled up or shared them with a few people personally when I had the chance. Neither option was a particularly effective or scalable way to share ideas or build connections with others.

Recognizing the need to create more content, both for my own growth in becoming a better leader and for the sake of my company, I began to write. I soon learned that the value I provide comes more from my ideas and experiences than my copy editing skills. So I developed a “brain dump” strategy with my team. Now, I can put all my ideas, insights and experiences on paper without concern for proper style, grammar or structure.

After some trial and error, I discovered what many professional writers already know: Streams of consciousness don’t just gush forth by themselves. They need a bit of prodding and an environment where they can flow. For me, that environment turned out to be on airplanes. Once I realized that travel made my brain dump sessions easier, my team helped me organize my writing around my flight schedule. Flying allows me to get away from the distractions of phone calls, Slack messages and Wi-Fi to reflect on industry trends, current events and my personal development.

When I started writing more, the pieces fell into place naturally. I began to see my role as a leader in a new light. Disjointed thoughts about our industry became coherent connections that helped us design smarter strategies. Above all, my team helped shape the raw material I created into a valuable tool to help our company grow.

How to become a better leader through writing

With so many reasons to write, every leader should make time to do it. Even those who don’t consider themselves natural writers (like me) can create useful, illuminating content with a little time and effort. These strategies will help even the least experienced writers put their ideas to paper, reap the benefits of written content and become better leaders.

1. Find your place.

Just as airplanes became my place to write, every leader needs a place to think. Find somewhere you can set aside the daily stresses of running a company and write without distraction.

Consider how different environments facilitate different types of writing. If I want to write about an industry trend, the plane back from a conference is the perfect spot. If I want to write about something more personal—for instance, my family or my growth as a person—I prefer to write at home, usually in my backyard. Pick an environment conducive to the type of content you want to create, put your phone on silent and let the words come naturally.

2. Throw out the rulebook.

Leaders like to be good at what we do, which can make writing a frustrating experience in the beginning. Those red squiggly lines under misspelled words discourage people with great ideas from writing them down.

Forget everything your English teacher told you, and write whatever you want, however you want to write it. Don’t even think about spelling, formatting, structure or titles—just keep moving forward. If you remember something you wrote earlier that you want to expand on, start writing about that again. You don’t need to go back and edit the document before you get into the flow of writing. Get all the information on the page first, then worry about the details later.

3. Trust yourself as a leader and your team.

None of us can do everything on our own. Handing off personal written content to team members can feel like opening your journal to strangers. But that’s exactly what you need to do to take your content from personal musings to marketing gold.

If you aren’t a great writer, hire people who are. Work with your team; trust them to stay true to your original intent while polishing your work into something reader-friendly. I provide my team with disorganized thoughts from my brain dumps, then rely on their expertise to shape those thoughts into a strong, cohesive piece. Surround yourself with people whose skills complement your own, and you can turn your writing into a powerful tool for your brand.

Writing has no barrier to entry. All you need is a laptop and your thoughts.

This article was published in December 2017 and has been updated. Photo by pikselstock/Shutterstock

John Hall is the co-founder and president of Calendar, a leading calendar app that’s designed to change how we manage and invest our time. He authored the best-selling book Top of Mind and is a must-see keynote speaker, which you can learn more about here.

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