Real Talk: Chuck Gillooley


Ever wondered how your required college composition courses will benefit you once you’re in the “real world”? Ever wondered how important reading and writing skills are to engineers, artists, marketing experts, nurses, and entrepreneurs? I’ve started this series, Real Talk, to give professionals in a variety of industries a chance to share why reading and writing are so critical to what they do.

Today we’re profiling Chuck Gillooley, a Bay Area realtor and co-owner of Dwell Realtors, Inc., in San Carlos.  Fun fact: I’ve always been irritated by real estate listings rife with typos and errors (because come on — if you’re trying to sell something that costs hundreds of thousands, possibly millions, of dollars, would it kill you to have someone copy edit?), so several years ago, when my husband and I were ready to buy a house, I vowed, as a matter of principle, to choose an agent who could write. That’s how we found Chuck, who writes the White Oaks Blog about the local real estate market and other issues and developments affecting the community — and shortly thereafter, Chuck helped us buy our home!

Describe your job.

I am a Realtor and co-owner of Dwell Realtors, Inc. in San Carlos. In just two short years of existence, Dwell has become the predominant real estate brokerage serving the residential real estate market in San Carlos, and we are rapidly expanding into adjacent communities. Along with my normal job as a Realtor, which is primarily to help people buy and sell homes, I also wear a variety of hats as a partner in the brokerage. Since I came into real estate from the technology world, I am often chartered with solving the myriad of technical challenges that face any small business owner, from setting up the office wifi, to projecting the company’s image on social media. There’s never a dull day in this business!

What kind of reading and writing do you do on an everyday basis?

If you have ever seen the immense stack of paper that accompanies the sale of a home, then you’ll know that reading is absolutely paramount in the real estate industry. When I am not plowing through a stack of disclosures on a specific property or carefully stepping through a sales contract, I am often researching local market trends and reading articles on the latest laws and regulations that pertain to the industry. From a writing perspective, I tend to be a bit more insane than just about every other Realtor. Nine years ago, I sought to develop a custom platform that would allow me to communicate with the community online with custom content about the real estate market and the interesting events that are happening in San Carlos. At that time, all that was available for Realtors was a stale website template of canned, generic data that looked exactly like every other Realtor’s page. From that project, the White Oaks Blog was born, and it is the single biggest generator of new business for me today. I spend several hours every day creating new content for the site.

What kinds of reading and writing skills are key in your field?

The vast majority of documents that cross my desk are sales contracts and the associated advisories are required for the sale of a home. While this sounds incredibly boring and tedious, reading through contracts and disclosures is probably the single most important task that a Realtor does on a daily basis. That’s because we need to boil this mountain of pertinent information down into the most important factors that will help our clients make an educated real estate decision, while still protecting their best interest in the process. This means that reading comprehension is a absolutely mandatory – every line and paragraph of a sales contract is put in there for a reason, and it’s critical for us to be able to understand the contract and then explain it to our clients in layman’s terms. In this frantic era of technological advances, text and email have become the preferred method of contact for most buyers and sellers, especially the younger professionals. Whether it’s answering client’s questions, keeping them updated on the status of the market, or walking them through the timelines of a home sale, so much of what we do is conveyed in writing. While the convenience factor is obvious, texts and emails provide a perfect trail of communication, which is important since real estate is probably the most litigious industry in the world. Understanding the various tools of communication, and being able to write clearly and concisely is therefore extremely important in the world of real estate. As one attorney once told me, “Before you hit ‘send’ on an email or text, consider it being projected up on the wall of a courtroom in front of a judge and jury. If you’re happy that what you have written will survive that test, then send it!”

Why are these skills important to being successful in your work?

Because I have chosen a blogging platform as the primary method of marketing myself to potential clients and the community as a whole, what I write on my website is the first impression that people will have of me long before I ever meet them (if I ever get to meet them.) It’s not only what I communicate on the website that is important, but it’s how I say it that is equally relevant. For example, I often post charts and graphs with statistics pertaining to the San Carlos real estate market. But anyone can copy and paste graphs, right? The real value that I bring to my readers is explaining what this data actually means, and how it impacts them. It’s about building credibility and familiarity through writing. Look at it another way – back in the ancient days of newspapers, I was a big fan of Herb Caen’s column in the San Francisco Chronicle. I read it every day. Although I never met Herb Caen in person, I felt that I already knew him. That’s because writing is a direct reflection of one’s personality – who you are comes through loud and clear in your writing. And that’s exactly what I strive to accomplish with the content that I write for my website. Nothing makes me happier than when a client says “We chose you as our Realtor because we are avid readers of your site, and we feel like we already know you.” In this ultra-competitive world of real estate, that’s a huge advantage.

What advice do you have for students, particularly college students in first- and second-year writing courses?

I could probably write an entire book just on this question alone. As I mentioned above, writing is about establishing familiarity and credibility with your audience – regardless of whether it’s a job application, or a blog post to thousands. In this technological era, your first contact with someone will likely be in a written format. Consequently, people will formulate their first impression of you by what they read from you, not necessarily how you project yourself in person. If you write dry, uninspiring prose, then people are going to subconsciously draw the conclusion that you’re probably like that in the flesh. (Read Malcolm Gladwell’s book Blink if you want an interesting take on first impressions). There are 5 rules that I will share with you to establish familiarity and credibility with your audience, and for being the very best writer that you can be:

  1. Read, read, read. Read as much as you possibly can. Books, newspapers, internet articles. I was a voracious reader as a kid, and much of my writing style was subconsciously influenced by what I read growing up.
  2. Expand Your Vocabulary. My college English professor taught be the most valuable lesson about reading: Have a dictionary by your side when you read (it’s already embedded in a Kindle!) When you encounter a word that you don’t understand, look it up!! Don’t just gloss over it — the author put it there for a reason. The stronger your vocabulary becomes, the better writer and reader you will be.
  3. Grammar is Everything. Nothing puts your credibility in the hole more quickly than lousy grammar. An email that’s full of typos, incorrect use of verb tenses, and run-on sentences will not convey a very unfavorable image of you.
  4. Proofread. I know we’re all very busy, but take 2 minutes to read what you’ve written before you send it. You’re not only hunting for simple grammatical mistakes, but you must also be cognizant of the tone of your message. One of the drawbacks of written communication is that it’s very easy for the recipient to misinterpret the “tone” of your message. Read your work from the perspective of the recipient and make sure your message is coming across the way you intended.
  5. Make Every Word Count. Just like a musician thinks through every note when writing a song, use the same philosophy with writing.



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