Leading

Writing Catalyzes Clarity

“Writing is hard work. A clear sentence is no accident. Very few sentences come out right the first time, or even the third time.”

Whether it’s a company update, a job description, a customer email, or a vision for the future, the act of writing catalyzes clarity. That’s what makes it so difficult. But if you put the time into writing something well, you’ll understand it better, and so will the people on the receiving end.

Next to hiring, writing is quite possibly the most important thing a leader can do to move the needle in their organization. Writing catalyzes clarity of thought. When done well, it demonstrates a certain mastery of the information being shared. Only when you understand every angle and nuance of a deeply complex topic or project can you share it with others in a way that’s clear and easy to understand.

As a CEO, I spent at least 30% of my time doing some form of creative writing. A few of the most impactful types of writing were:

• Friday notes: messages to the entire company. I wrote 205 of these during my time as a CEO, and they served as a great way to loop the team into what was top of mind.
• Job descriptions: most companies go through the motions, but I find it’s a great way to set your company apart and align with the hiring team on what’s needed from the ideal candidate.
• Company updates: whether it’s a monthly update on a specific initiative, or a review of recent results, writing an update to stakeholders forces you to reflect on the big picture — wins, challenges, and opportunities.
• Self-assessment: as covered in the essay on annual planning written self-reflection is critical to your growth as a leader.

"The act of writing — when you try to explain it to someone else — is where you really are forced to think things through and not be sloppy in your thinking."

One example of writing catalyzing clarity is a TED talk. Sure, it’s a presentation, but don’t think for one second that every word of it wasn’t written and re-written dozens, or even hundreds of times. And yet, at the end of 15 minutes or so, a large group of people can gain a shared understanding of a deeply nuanced, complex, and often technical topic — then act collectively. Ted talks have inspired public policy change, spurred innovation, and even predicted pandemics.

When you write about something, you have to see the big picture — to understand all the context — in order to discern which blades of grass are worth noting. This process of communicating with clarity, developing a shared understanding, and acting collectively creates tremendous leverage in a business.

Good writing can give a company superpowers. Look no further than Jeff Bezos’ 2018 shareholder letter, in which he underscores the importance of writing at Amazon:

Six-Page Narratives

We don’t do PowerPoint (or any other slide-oriented) presentations at Amazon. Instead, we write narratively structured six-page memos. We silently read one at the beginning of each meeting in a kind of “study hall.” Not surprisingly, the quality of these memos varies widely. Some have the clarity of angels singing. They are brilliant and thoughtful and set up the meeting for high-quality discussion. Sometimes they come in at the other end of the spectrum.

In the handstand example, it’s pretty straightforward to recognize high standards. It wouldn’t be difficult to lay out in detail the requirements of a well-executed handstand, and then you’re either doing it or you’re not. The writing example is very different. The difference between a great memo and an average one is much squishier. It would be extremely hard to write down the detailed requirements that make up a great memo. Nevertheless, I find that much of the time, readers react to great memos very similarly. They know it when they see it. The standard is there, and it is real, even if it’s not easily describable.

Here’s what we’ve figured out. Often, when a memo isn’t great, it’s not the writer’s inability to recognize the high standard, but instead a wrong expectation on scope: they mistakenly believe a high-standards, six-page memo can be written in one or two days or even a few hours, when really it might take a week or more! They’re trying to perfect a handstand in just two weeks, and we’re not coaching them right. The great memos are written and re-written, shared with colleagues who are asked to improve the work, set aside for a couple of days, and then edited again with a fresh mind. They simply can’t be done in a day or two. The key point here is that you can improve results through the simple act of teaching scope – that a great memo probably should take a week or more.

When an entire company embraces the craft of writing, it becomes a superpower. Amazon is certainly a great example. Stripe is another company with a strong writing culture, and it’s something I worked hard to foster at Help Scout.

As a leader, if you value excellent writing, hold others accountable to a high bar, and meet/exceed that bar yourself, your company will move faster, make better decisions, and stay in sync as an organization.