“Good writing is good conversation, only more so.” – Ernest Hemingway

Not too long ago, my buddy John Barrow invited me onto his Facebook Live show to rap on a topic that was getting a lot of attention with his clients. Sales leaders were asking if he had any tips to help improve the writing acumen of his staff. Apparently, the level of writing skills out there in the wild is not pretty, and it was something that I have been noticing as well.

Did you know that bad writing costs America nearly $400 billion every year? It’s a provocative statement, but this article clearly lays out a compelling case that poor writing skills is a soul sucking, economic waste. The recipients and readers of such dreck would agree, as this one quote so neatly sums up, “Poorly written material wastes a lot of my time.”

Most of the blame goes to marketing. The rise of inbound channels and content marketing has produced an endless stream of whitepapers, blog, newsletters, and social media posts in the attempt to makes their respective companies look smarter. The vast majority of this content consists of product centric jargon and  buzzword-laden business speak.

Sales writing is just as awful. Crimes against the English language are being committed daily. Reading the copy I see in most sales emails and proposals leaves me stunned, wondering if the sender ever wrote anything during all their years of schooling. And I am not even the intended audience most times. Just imagine what actual prospects must think. It may not occur to you, but bad writing costs you deals.

This is meant to be a wake up call, not a putdown. Even if you think your writing is decent, it can always be better. No one is telling you this, though. My hope is that these few tips can help you become the type of professional who uses writing skills as a tool to win more meetings, gain credibility, and close deals.

How do you do that? A good starting place is this framework from Harvard Business Review:


  • Plan out what you will say to make your writing more direct and effective
  • Use words sparingly and keep sentences short and to the point
  • Avoid jargon and “fancy” words. Strive for clarity instead.


  • Argue that you simply can’t write. Anyone can become a better writer with practice.
  • Pretend that your first draft is perfect, or even passable. Every document can be improved.
  • Bury your argument. Present your main idea as soon as possible.

There are also many specific rules around spelling and grammar which are easy to confuse. For example, it is common to see errors with subject-verb agreement or the use of certain words like“that” and “which” or “affect” and “effect”. Even basic mistakes like “there” and “their” crop up in my writing (all the more reason to edit your work). Instead of trying to remember all of these rules, use tools like Grammarly to help catch these common gotchas.

The most important lesson that I learned by practicing my writing is to find your unique voice. As Hemingway says, the mark of good writing is that it feels natural, like you are speaking with someone. You do not want to sound like a brochure, or pretend you are some self-important big wig. That leads to the type of content that sounds dead and unemotional. You build influence by being more of the authentic you and injecting personality into your writing.

How do you unlock your inner voice? The only way that happens is if you write more often and make writing a regular practice. Part of that can be journalling, which helps unlock ideas stuck in your head, but by far the most impactful way to become a better writer is putting you work out there in public.

As the NYC tech startup community was taking off, I started a blog to help build up my credibility as an angel investor. I looked to folks like Fred Wilson and Darmesh Shah as inspirations, so I wrote everyday. Not all of it was great. In fact a lot of it seems embarrassing now. However, it succeeded on two fronts by raising my profile with entrepreneurs and improving my writing.

I still write regularly. These LinkedIn posts are one avenue. I also distribute a newsletter for the 15,000 members of the Enterprise Sales Forum and a much smaller one for prospects related to my work at Stack Overflow. When you put your work out there publicly, you think more, edit more, and reflect more on your writing. In the process, you not only become a better writer, you have more clarity and confidence and conviction.

When your writing improves, a magical thing happens. Your writing has the power to open doors across the sales process from prospecting to closing. Rather than the typical lame SDR email template, a well crafted, personal note can be a unique differentiator and call attention to your professional manner. I know for me, some of my biggest deals started from my writing.

Good writing helps you gain respect. It shows you are not just a run-of-the-mill sales rep, but a true business professional who can solve problems. That distinction is critical when you engage C-level executives. Your ability to communicate clearly speaks volumes about your credibility and capability in the eyes of decision makers.

Maybe you are having trouble though making writing a regular habit. Stay committed to the path of self-improvement and learning can be challenging with the distractions around us at work and at home. If you want to make a fundamental change in your performance, make writing a habit-forming practice. Get out the pen and pad and get started on the path toward better writing!