Your emails are annoying.

There are few things that shake my confidence in humanity more than email.

This is not solely the fault of poorly-spelled, grammatically-unsound student emails, but is equally due to the poor email etiquette I see in emails from colleagues and career professionals on a daily basis.

One immensely aggravating example of such misuse occurred this week when the athletics department at my university created an email list that automatically added all faculty and staff members. I found myself not annoyed as much by the email list as by the faculty and staff taking the incorrect steps to be removed from the email. Rather than emailing a designated address with the subject line “Please Unsubscribe” as had been directed, dozens of people, most with graduate degrees, hit “Reply All” to say “Please Unsubscribe.” As a result, for three solid hours hundreds of university employees were receiving unnecessary emails, undoubtedly getting nudged from more important tasks and wasting time on communication that did not pertain to them.

In the midst of this afternoon saga, I could not help but think that Wired’s David Pierce was spot-on when he opined, “The problem isn’t email. It’s our relationship to email that’s broken.”

We email users are dumb.

Knowing that freshly-minted college graduates and seasoned professionals are equally apt to misuse the technology, below are 10 observations/lessons about email usage that may pertain to you and/or to someone whose emails often trigger the desire to throw a stapler through your computer monitor (please forward this to those folks).

(1) Your email address is awful. This one is mostly intended for college juniors/seniors and recent graduates, but I have seen plenty of questionable email addresses from people who have been in careers for decades. Last week I was working with a client who had run his own multi-million dollar business in Washington, D.C. for 20 years. His email was something to the effect of

Make sure your email address is professional and that it is clearly represents your name. For college students, make the change now; don’t wait until you graduate.

(2) You sent an email to the wrong recipient(s). Double-check the email address(es) you are sending. You never know who you may incorrectly send an email to and what ramifications that could bring.

Last week I received an email from an administrator at my university that was not intended for me. I found the mistake to be very unprofessional, especially considering the money this person makes.

Anyone can make this mistake, but it can be very unbecoming.

(3) Not everyone in the office needs to know you are unable to attend tomorrow’s meeting because of laser hair removal. Sorry, I should clarify: I imagined someone sending an email about tomorrow’s meeting to which you sent a Reply All with information about your unwanted arm hair.

If you want to respond to an announcement with a “Congratulations” or an “I’m so sorry” do not send it to everyone on the email, only to the person for whom the response is relevant. The vast majority of Reply All messages I see are just electronically-delivered packages of self-importance. It’s really great you think you are a fantastic person for sending “thoughts and prayers” to Nancy, but let Nancy know that, not the rest of us.

In short, use Reply All on a need-to-know basis. If the person(s) to whom you are sending your email DO NOT need to know, take us off the email. Please!

(4) Your subject line is too long and says nothing of value. Subject lines with ALL CAPS or in all lower-case go to Spam folders. Subject lines that are too long and void of important information are annoying.

Keep your subject line clear and concise (ex. “Question regarding tomorrow’s assignment” or “Information about our 12/5 meeting”) as a courtesy to the person receiving the email. If it’s important they need to know it so they can open, read, and respond. If it is not, they need to know that too so they can attend to the email when they have a free moment or two.

(5) Keurig cup refills are not a priority. Use your email’s priority flag function sparingly. Not everything is a ticking time bomb. If something is in need of immediate attention (and calling on the phone is not an option), a priority flag could be in order. If that is not the case, do not use it.

As for the Keurig cup refills, that was an actual email sent to department faculty and staff.

(6) Your greeting is completely unprofessional. Know your audience. If the person you are emailing is more important than you or your relationship has not evolved into anything close to a friendship, a nice “Hello Ms.” or “Dear Dr.” or “Hi Mr.” are in order. Even if the relationship is more casual, “Hi Maria” or “Dear Dan” are more courteous than “Yo Phil” or “Sup Dawg.”

No matter where you are in your career, be polite with your greeting and respect the person who you are emailing.

(7) Your email is way too long. You may have the greatest idea or plan in the world, but if it takes 10 minutes to read about it in an email, most people are not going to give a shit.

Get to the point, tell the reader what they need to know, what needs to be done, and do not use the platform as a way for you to show off your vocabulary or work ethic If either are deserving of praise, trust that you will be recognized for it at some point.

(8) Your using uncorrect grammars. (FYI: Those mistakes were intentional.) Few things make me immediately think less of someone than poor grammar and punctuation in a professional email. This is not because I think I am smarter than other people (that’s an objective truth), but because it shows me you have not taken an extra 30 seconds to read through your email to make sure you have spelled things correctly, that grammar is on-point, and that punctuation is where it needs to be.

From now on, when you write an email, take an extra minute to read and revise. It’s the least you can do to stop yourself from sounding like a dumbass.

(9) Your email will be forwarded so consider the content. When you are writing an email, consider the content and imagine that whatever you type will be forwarded. This is another way of reminding yourself to leave out the personal stuff, the problematic language, etc. Anything that could come back to haunt you should be kept from email.

This relates to both content and tone. Make sure the words you use convey what you really want to say and that the tone that comes from those words matches the tone you want the receiver to perceive.

Lastly, emails do not go away. They form a digital paper trail. Consider this when typing and when in doubt, call the person or meet with them face-to-face.

(10) You need to respond in a timely fashion. If someone emails you and it looks important (i.e. they’ve followed the insight of No. 4), you need to read and respond within 24-48 hours. This does not include the weekends or if you are on vacation, but if you are in the office, you need to respond.

Otherwise, you are just adding to the growing population of dumb email users.

10 simple observations and you are on your way to becoming less annoying to work with.

Nice job.



The Value of Knowing When to Shut Up

For golf caddies to keep their jobs they either need be skilled at the technical stuff (reading greens, giving advice, etc.) or good at recognizing what kind of small talk is wanted during a round, i.e. knowing when to talk and when to shut up.

hinske and hammel

As a lifelong Cubs’ fan, caddying for Eric Hinske and Jason Hammel during the 2016 World Series run was a highlight of my caddying career.

I like to think I have collected sufficient evidence to prove this claim during the last 11 summers I have spent as a golf caddie at some of the best clubs in the country, seeing more caddies fired for bad communication than for bad golf advice. And while I have witnessed plenty of caddies canned for the same shenanigans lampooned in Harold Ramis’s 1980 classic Caddyshack, arriving to work hungover, still drunk, or stoned are often forgiven if you know how to talk.

I am not good at the technical stuff and there is a long list of disappointed golfers who can attest to that. However, I know how and when to talk to members and their guests, often über wealthy and über powerful titans of industry. This ability to assess the communicative potential of these interactions and to act accordingly have led to the development of professional connections and friendships I value greatly. For example, before launching Jay Communication Solutions. I spent 18 holes picking the brain of one of the most successful CEOs in the United States who suggested I go all-in on my idea. Even now I continue to call him up for advice.

In the professional world, knowing when to listen, when to talk, and what to say are invaluable skills not everyone takes the time to develop. As a young professional and/or someone trying to climb the organizational ladder, being able to evaluate what kind of conversation your colleagues and superiors want is even more valuable considering the faster you can understand the power dynamics the less prone you are to put your foot in your mouth.

I know firsthand this can be difficult, especially when people are wrong or rude. When I first started caddying, I was temporarily fired for yelling back at a golfer who screamed “Find that f*cking golf ball, caddie” at me. Apparently, “Find your own f*cking golf ball” was not the most prudent response. Luckily, the member who yelled at me was disliked by most of the membership and club management.

Being able to assess what you can get away with saying and to whom are key, whether that means speaking your mind when someone is wrong or chiming in on a conversation to which you have something to add.

Here are some general rules for communicating with others above you on the power hierarchy (professionally, this means your superiors, but personally, I guess this might help with your in-laws as well):

  1. Listen first, talk second. Observe and evaluate your audience. Collect as much data as possible. Figure out what information they respond to and what approaches they ignore. The more you know about your audience (of one or of many), the more effective your message can be once you ask for a promotion, suggest an operational change, or offer your perspective.
  2. Build rapport before mining for data. It is important to build a relationship prior to asking questions that require candid answers. If some C-suite executive has no idea who you are, asking her about her approach to leadership might be fruitless. Listening and showing respect while waiting for the opportunity to ask such a question will offer more valuable answers. I cringe when I hear a caddie ask someone like Peyton Manning or Jay Bilas a personal question on the driving range; give the relationship some time to establish itself before even considering asking a question that is not anything but superficial or task-related.
  3. Never get too comfortable. Stay on your toes even if it feels like things are going well. I have caught myself getting too comfortable by the seventh or eighth hole and talking too much, turning members off by offering too much information they don’t care about or asking too many questions. Always be mindful of the power dynamics. The people above you on the hierarchy have the freedom to talk when they want; if you want to get to this place, be cognizant of the flow of conversation. Self-awareness is a revered personality trait.
  4. Exit with confidence, respect, and authenticity. Take the opportunity to end a conversation on your own terms, rather than waiting for someone else end it because it’s getting awkward or time is running out. Being aware of when an interaction is drawing near a close is a capacity not everyone has, but if you can highlight this ability, it shows others that you recognize and respect the value of their time. It is also a good way to accentuate confidence and in showing gratitude, you can convey authenticity.

In closing, the abilities to listen to and communicate with others will strengthen over time, which means by the time you have reached a more powerful position, you will have the experience and be able to leverage your fine-tuned conversation skills in more valuable ways.

5 Podcasts Every Entrepreneur or Young Professional Needs to Hear

I am a ravenous consumer of podcasts.

Much of the political and sports commentary I consume comes from podcasts. I have go-to podcasts for entertainment, culture, and news. Even the traditional radio shows that had been appointment listening (This American Life and The Dan Patrick Show) are more valuable to me in their condensed, podcast format with no commercials and the ability to skip ahead.

The platform also offers an extensive collection of podcasts beneficial for the young professional, audio to be consumed on-the-go that highlights things like the traits of effective leaders, lessons to be learned from start-ups, the successes and failures of revered entrepreneurs, and the best approaches for productive team communication and collaboration.

As we enter the dog days of summer and are forced to endure the season’s bad box office blockbusters, the Bachelor in Paradise drama, and the monotony of marathon baseball games, these five podcasts offer reprieve that will simultaneously give you invaluable insight into building your brand, energizing your start-up, dealing with incompetent leadership, and more.

masters of scale#1 – Masters of Scale

What’s the premise? LinkedIn cofounder and venture capitalist Reid Hoffman interviews entrepreneurs who have grown businesses and non-profits from tiny ventures to revered institutions. Hoffman’s first season has been loaded with big name guests including Nancy Lubin, CEO and Founder of Crisis Text Line, discussing grit and giving, and Airbnb Co-Founder and CEO Brian Chesky talking about the importance of customer relations for start-ups.

What’s the value? Hoffman talks to entrepreneurs not only out to make some dough, but who are constantly thinking about their commitment to the public good. Many interviewees are under 40 and understand failure and the social responsibility that comes with success. Plus, if you are someone launching or growing a small business there is plenty to learn from the conversations about what to do and what to avoid.

Where can you find it? All episodes can be streamed and downloaded via the podcast’s website, as well as on Apple Podcasts, Stitcher, and Google Play Music.

james altucher#2 – The James Altucher Show

What’s the premise? Reid Hoffman wants to know what makes businesses successful; James Altucher’s wants to know what makes people successful. In the same vein as The Tim Ferriss Show, but without the bravado, Altucher has conversations with interesting guests and tries to uncover what decisions and lifestyle choices got them where they are. Highlights from recent episodes include Ryan Deiss, Founder and CEO of DigitalMarketer, talking about the failing promise of college, and designer and podcaster Debbie Millman discussing how to persevere through rejection.

What’s the value? Life lessons. Altucher’s guests explain the little things they have changed or integrated into their lives that made success possible. Things like journaling or meditation are not business decisions, but life decisions anyone can make that prime the pump for creative thinking, idea generation, and productive collaboration.

Where can you find it? All episodes can be streamed and downloaded via the podcast’s website, as well as on Apple Podcasts, and Stitcher.

ForbesUnder30_facebook#3 – Forbes Under 30

What’s the premise? Forbes’s “30 Under 30” list is an annual collection of young innovators and entrepreneurs often making a name for themselves through disruption. However, while the list is 600 deep with some names (ex. Kylie Jenner, Patrick Kane) triggering more cringe than intrigue, the podcast takes the best from the list and host Steve Goldbloom asks questions that get at what makes them tick.

What’s the value? Listeners get to delve deep into the not-yet-jaded minds of the future influencers of culture, politics, and technology. Sometimes what we hear is a little scary; sometimes it’s a breath of fresh air. Perhaps what is most interesting is the juxtaposition between the interviews from Masters of Scale and this podcast: Forbes Under 30 is like listening to conversations with Mark Zuckerberg at 22 when he was a genius, but still an unrefined codejockey (just listen to this interview with inDinero Founder Jessica Mah). There is plenty to learn from millennials trying to make their own mark, especially about how to communicate respectfully and how to become respected.

Where can you find it? All episodes can be streamed and downloaded via Apple Podcasts.

sil podcast#4 – Stanford Innovation Lab

What’s the premise? On this podcast, Stanford professor Dr. Tina Seelig interviews innovators, researchers, and social scientists examining what works and what fails in the realm of organizational management.

What’s the value? Of all the podcasts listed this one is the most entertainingly educational as Seelig and her guests take complex ideas and make them relevant to environments of collaboration and organizations.  For example, how to guide crazy ideas towards productive outcomes or how to preplan a brainstorming session are skills explained on this show that have value for all communication environments.

Where can you find it? All episodes can be streamed and downloaded via the podcast’s website, as well as on Apple Podcasts.

hbr ideacast#5 – HBR IdeaCast

What’s the premise? Few of us have the time to sit down and read an entire issue of the Harvard Business Review, but all of us should be finding the time to listen to IdeaCast, which summarizes the highlights from each issue. This is a must-listen for anyone impacted by communication or leadership as host Sarah Green Carmichael talks with the best researchers on conflict management, collaboration, motivation, and productive team building.

What’s the value? Every HR department should be listening to this podcast; every professor should be assigning it for their classes; and every entrepreneur should be putting what they learn from this podcast to work as they build their personal brand or start-up. The Harvard Business Review is revered for a reason; this podcast is no different.

Where can you find it? All episodes can be streamed and downloaded via the podcast’s website, as well as on Stitcher, and SoundCloud.