I had first created this blog topic very early in 2020, so it was the pre-COVID-19 world. Who would have thought in February that 
Skype, Zoom, GoToMeeting, Microsoft Teams, and Google Hangouts would be the norm over in-person dialogue in June? Not me.
So as we all now join our weekly meetings and client conversations from our couches, there is already a new level of casual conversation natively injected into our everyday business lives. Dogs barking, “I’m hungry” from the kids (or the spouse), and doorbells ringing are commonplace now.
Actually, at the moment I’m writing this, my spouse is on a work call on speaker. The presenter is at her home. There has already been a toddler interruption and presently I am hearing a dog playing with its toy and making the toy squeak for the past few minutes! It’s something we’ve all come to accept in this 2020 business environment.
As I typically do in my blog pieces, I’d like to step back in time. This, to contrast how far — and how quickly — the casual metamorphosis has happened.
FROM SUITS TO KHAKIS TO JEANS
Workplace attire just a few decades ago was typically suits and ties for men, dresses and heels for women. Take a quick glance at Vintage Dancer’s take on 1950 Men’s Business Attire. As time moved forward, there was the occasional “Jeans Friday.” Then business casual allowed men to get by with khakis and polo shirts.
Or maybe a dress shirt with no tie. Women migrated to more comfort, as well. Slacks and more comfortable shoes, sometimes even open-toed shoes!
And over the past decade, this has morphed into jeans and just about any shirt, as long as it wasn’t too revealing or contained profane commentary. The business world, just in terms of acceptable attire, has morphed greatly.
DEAR SIR TO DEAR BILL TO HEY
As this change has happened, the manner of communication has also become more casual. Instead of formal physical memoranda, emails became the norm. And in more recent years, even text messaging is acceptable for many business scenarios where such informal communication was previously unheard of.
So just because one “can” include a wink emoji at the end of a message, does it mean that it’s OK? Surprisingly to those more accustomed to more starchy communication, it could be just fine. But how informal communication can get depends on a few factors: Audience, Familiarity, and Conversation Tone.
KNOW YOUR AUDIENCE
I researched to try to find if any particular person can be credited with the phrase, “Know your audience,” but it seems as if it’s a phrase that just evolved into common usage. And whether being casual is OK or not goes somewhat back to the dress shirt and tie business days.
It can also vary depending on the difference between the communication sender and receiver, plus the title or status of the receiver. 
In the example by more simple terms, it’s unlikely that a new entry-level person would get by emailing the corporate CEO to thank him/her for the new job with a “Thanks for the job, bro. The new office is da bomb” message. People on a peer level tend to communicate more informally as it’s not typically someone who can, well, terminate your employment.
However, familiarity and time can also influence the level of casualty with seniority. If the company president is someone with whom, after time, you’re completely familiar and comfortable with, then more casual conversation can become perfectly fine.
Prior to joining the Shout It Out Design Team, I had been with a company for nearly 20 years, and the average person had been there for 14 years. Everyone knew each other’s spouses, children, hobbies, bodily aches, and personality quirks. Nothing was secret nor sacred, so everything was susceptible to some light-hearted jabbing humor.
TAKE CUES FROM OTHERS
Much like you might choose an appropriate outfit based on what others are wearing, the context of your situation will determine how casual your tone should be.”
Having received a message, there’s often an obvious connotation that can be read into as to how casual a reply can be. “I’m pulling my hair out over this. Can you please rescue me?” can likely get a casual response. “Could I please get the most recent sales statistics with your assessment of how we look in the upcoming quarter?” seems to request a more formal response.
So to the final point, conversation tone is a good cue to determine an appropriate response. Quickly-jotted notes in an email can make a reply without full, formal sentences to be just fine. Texts, being shorter, are on the more informal end of the professional spectrum.
If in doubt, keeping the message professional-but-friendly seems to be today’s norm. Much like you might choose an appropriate outfit based on what others are wearing, the context of your situation will determine how casual your tone should be.
Especially in writing, polysyllabic content seems propitious to be an affront to the receiver — more likely to elicit a negative response. Simpler phrasing for what I just said: Don’t use big words to sound smart.
Good spelling, complete sentences, and a proper tone are more than likely enough to convey a message, to have it received with the intended tone, and to get a response that matches the original communication.
Feeling like it’s a casual conversation with someone you know well and there’s a bit of a joke. Sure, include that winking emoji. “Lol” if it works. Just remember to consider the recipient and the overall content to keep your message on track!
